Note: Within nine months of the publication of the mention of the grant of the European patent in the European PatentBulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with theImplementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has beenpaid. (Art. 99(1) European Patent Convention).

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(12) EUROPEAN PATENT SPECIFICATION

(45) Date of publication and mention of the grant of the patent: 06.07.2016 Bulletin 2016/27

(21) Application number: 09831388.5

(22) Date of filing: 10.12.2009

(51) Int Cl.:C07D 239/36 (2006.01) A61K 31/505 (2006.01)

A61P 15/10 (2006.01)

(86) International application number: PCT/CN2009/001418

(87) International publication number: WO 2010/066111 (17.06.2010 Gazette 2010/24)

(54) PHENYL PYRIMIDONE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, PREPARATION METHODS AND USES THEREOF

PHENYLPYRIMIDONVERBINDUNGEN, PHARMAZEUTISCHE ZUSAMMENSETZUNGEN, HERSTELLUNGSVERFAHREN UND ANWENDUNGEN DAVON

COMPOSÉS DE PHÉNYLPYRIMIDONE, COMPOSITIONS PHARMACEUTIQUES, LEURS PROCÉDÉS DE PRÉPARATION ET LEURS UTILISATIONS

(84) Designated Contracting States: AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK SM TR

(30) Priority: 10.12.2008 CN 200810204368

(43) Date of publication of application: 02.11.2011 Bulletin 2011/44

(73) Proprietors: • Topharman Shanghai Co., Ltd.

Shanghai 201209 (CN)• Shanghai Institute of Materia Medica,

Chinese Academy of SciencesShanghai 201203 (CN)

• Topharman Shandong Co., Ltd.Anqiu, Shandong 262123 (CN)

(72) Inventors: • LIU, Zheng

Shanghai 201209 (CN)• LI, Jianfeng

Shanghai 201203 (CN)• YANG, Xiaojun

Shanghai 201209 (CN)• WANG, Zhen

Shanghai 201203 (CN)• ZHANG, Jinfeng

Shanghai 201209 (CN)

• ZHU, YiAnqiuShandong 262123 (CN)

• TIAN, GuanghuiShanghai 201203 (CN)

• JIN, QingShanghai 201209 (CN)

• SHEN, JingkangShanghai 201203 (CN)

• ZHU, WeiliangShanghai 201203 (CN)

• JIANG, HualiangShanghai 201203 (CN)

• SHEN, JingshanShanghai 201203 (CN)

(74) Representative: Grünecker Patent- und Rechtsanwälte PartG mbBLeopoldstraße 480802 München (DE)

(56) References cited: WO-A1-2007/056955 CN-A- 1 746 171GB-A- 1 541 351 US-A- 4 031 093US-A- 5 290 933 US-A- 5 874 440US-A1- 2002 013 464

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EP 2 383 262 B1

• Pinner: "Über Imidoäther des Trimethylencyanids", Chemische Berichte, 1 January 1890 (1890-01-01), pages 2942-2956, XP055198202, Retrieved from the Internet: URL:https://s3.amazonaws.com/objects.readc ube.com/articles/downloaded/wiley/8a0a2cd6 f040e93b45ddf9e60041c87938070fd89407e471dc 398c4703c97bcd.pdf?AWSAccessKeyId=AKIAIJZY FKH6APDFT3HA&Expires=1435276800&Signature= USudzbLo4bSKjBLoKtGLz83oIbE=&response-cont ent-type=application/pdf [retrieved on 2015-06-24]

Remarks: The file contains technical information submitted after the application was filed and not included in this specification

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Description

FIELD OF THE INVENTION

[0001] The present invention relates to a class of phenylpyrimidone compounds, the pharmaceutically acceptablesalts and solvates thereof. The present invention also relates to a pharmaceutical composition comprising the compoundand a process for preparing the compound. The phenylpyrimidone compound according to the present invention caneffectively inhibit type V phosphodiesterase (PDE5), and thus can be used for the treatment of various vascular disorders,such as male erectile dysfunction, and pulmonary hypertension.

BACKGROUND OF THE INVENTION

[0002] Sildenafil (WO94/28902) developed by Pfizer Inc. is an oral PED5 inhibitor for treating male erectile dysfunction.It increases the level of cGMP, an enzyme substrate of type V phosphodiesterase(PDE5), in smooth muscle cells torelax the smooth muscle and induce vasodilatation by inhibiting the type V phosphodiesterase, so as to increase theflow rate of blood in the smooth muscle to induce erection.[0003] From then on, many big pharmas and research teams have developed a lot of PED5 inhibitors with otherdifferent chemical structures. WO98/49166, WO99/54333 and WO 01/87888 disclose another series of pyrazolo[4,3-d]pyrimidin-7-one derivatives; WO2004/096810 discloses a series of 5,7-diaminopyrazolo[4,3-d]pyrimidine compounds;WO2004/108726 discloses a series of dihydropyrrolo[2,3-d]pyrimidiri-4-one compounds; WO2004/101567 discloses aseries of imidazo[1,5-a]-1,3,5-triazin4(3H)-one compounds; WO2006/126081, WO2006/126083, WO2007/020521 andCA02339677 disclose a series of pyridinopyrazinone compounds; WO2005089752 discloses a series of tetracycliccarboline compounds; WO2005/012303 and WO2007/002125 disclose a series of xanthine derivatives; andWO03/020724 discloses a series of polycyclic guanidine xanthine compounds. WO2007/056955 discloses pyrazolopy-rimidinone derivatives. All of these compounds also show strong inhibitory activities of PDE5.[0004] The developing PDE5 inhibitors are also used for pulmonary hypertension, diabeticgrastrointestinal disorder,insulin resistance, hyperlipemia and the like.[0005] Although sildenafil has achieved a good clinical effect, it shows some side effects, such as headache, facialflushing, upset stomach, nasal obstruction, blurred vision, sensitivity to light, bluish vision and the like in clinic, since italso has inhibition on other PDE isoenzymes to the different extent. On the one hand, as the side effects are dose-dependent, there is a need for a PDE5 inhibitor having a stronger activity to descrease the dose and alleviate the sideeffects; on the other hand, since the vision disorders is caused by inhibition of type VI phosphodiesterases(PDE6) existingin retina, it is another object in finding out a new PDE5 inhibitor to increase the selectivity, especially against PDE6.

SUMMARY OF THE INVENTATION

[0006] Thus, one object of the invention is to provide a type of phenylpyrimidone compounds of formula I, the phar-maceutically acceptable salts or solvates thereof.[0007] Another object of the invention is to provide a pharmaceutical composition containing the said phenylpyrimidonecompound of formula I, the pharmaceutically acceptable salts or solvates thereof.[0008] Still another object of the invention is to provide a process for preparing the said phenylpyrimidone compoundof formula I, the pharmaceutically acceptable salts or solvates thereof.[0009] Still another object of the invention is to provide a use of the said phenylpyrimidone compound of formula I, thepharmaceutically acceptable salts or solvates thereof in preparing drugs for treating various vascular disorders, suchas male erectile dysfunction, pulmonary hypertension. The problem of the present invention is solved on the basis ofclaims 1 to 12.[0010] The inventors of the present invention designed and synthesized a type of novel phenylpyrimidone compoundsof formula I, the pharmaceutically acceptable salts or solvates thereof:

EP 2 383 262 B1

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wherein,

R1 and R2 are each independently H, C1-C10 alkyl; C3-C6 alkenyl; C3-C6 cycloalkyl; halogen; CF3; OR5; NHCOR8;aryl; or C1-C4 alkyl optionally substituted with aryl, or OR5;Z is OR3;R3 is C1-C6 alkyl; C3-C6 cycloalkyl; C3-C6 alkenyl; C1-C3 haloalkyl; or C1-C3 alkyl substituted with C1-C3 alkoxy orC3-C6 cycloalkyl;R4 is NO2; CN; SO2NR6R7; NR9R10; COR11; OR12; C2-C4 alkyl optionally substituted with OH, CN, C1-C4 alkoxy,NR6R7, CONR6R7 or CO2R8; C2-C4 alkenyl optionally substituted with CN, CONR6R7 or CO2R8; or R4 is a 5∼7-member heterocyclyl optionally substituted with one or more substituents selected from OH, COOR8, CONH2, C1-C6alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, aryl, Het, and C1-C6 alkyl substituted with halogen or alkoxy or hydroxyl; orR4 is a 5- or 6-member monosaccharide group optionally substituted with one or more substituents selected fromC1-C6 alkyl, trimethylsilyl, benzyl and acetyl;R5 is H; C1-C6 alkyl; C3-C6 alkenyl; C3-C6 cycloalkyl; C1-C4 alkyl optionally substituted with OH, C1-C4 alkoxy orNR6R7; aryl; or Het;R6 and R7 are each independently H, OH, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 alkenyl, C3-C6 cycloalkyl, adamantyl,C3-C8 lactamyl, aryl, Het, or (CH2CH2O)jH wherein j is 1∼3; or R6 and R7 are each independently C1-C6 alkyloptionally substituted with OH, C1-C4 alkoxy, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, NR13R14, aryl,Het or 4∼8-member heterocyclyl; or R6 and R7 are each independently a 4∼8-member heterocyclyl optionally sub-stituted with one or more substituents selected from OH, COOR8, CONH2, COR16, SO2R16, C1-C6 alkyl, C1-C4alkoxy, C3-C6 cycloalkyl, aryl, Het and C1-C6 alkyl substituted with halogen or C1-C4 alkoxy or hydroxyl; or R6 andR7, together with the nitrogen atom to which they are attached, form a 4∼8-member heterocyclyl optionally substitutedwith one or more substituents selected from OH, COOR8, CONH2, COR16, SO2R16, C1-C6 alkyl, (CH2CH2O)jHwherein j is 1∼3, C1-C4 alkoxy, C3-C6 cycloalkyl, aryl, Het, and C1-C6 alkyl substituted with halogen or C1-C4 alkoxyor hydroxyl; or R6 and R7, together with the nitrogen atom to which they are attached, form glucosylamino group,amino-acid residue, amino-acid ester residue or amino-amide residue, which are optionally substituted with one ormore substituents selected from C1-C6alkyl, NR13R14, COR16, benzyl, benzyloxycarbonyl and t-butyloxycarbonyl;R8 is H, C1-C6 alkyl or aryl;R9 is H, C1-C6 alkyl or SO2R16;R10 is H; C1-C6 alkyl; COR15; SO2NR6R7; SO2R16;

a 5- or 6-member monosaccharide group optionally substitued with one or more substituents selected from C1-C6alkyl, trimethylsilyl, benzyl and acetyl; or, R10 is a 5-member heterocyclyl optionally substituted with one or moresubstituents; or, when R9 is H, R10 is an amino-acid residue optionally substituted with one or more substituentsselected from OH, C1-C6 alkyl, C1-C4 alkoxy, COR16, benzyl, benzyloxycarbonyl and t-butyloxycarbonyl;R11 is H; OH; C1-C6 alkyl; aryl; Het; NH(CH2)kNH2, NH(CH2)kNHS02R16, or NH(CH2)kNHCOR16, wherein k is 0∼4;C1-C3 alkyl substitued with halogen, OH or C1-C6 alkoxy; or (CH2)mNR6R7, wherein m is 0∼2; or, R11 is an amino-acid residue or an amino-amide residue optionally substituted with C1-C6 alkyl or C1-C4 alkoxy;R12 is H, COR19, SO2R16, or a 5- or 6-member monosaccharide group optionally substitued with one or moresubstituents selected from C1-C6 alkyl, trimethylsilyl, benzyl and COR16;R13 and R14 are each independently H or C1-C6 alkyl; or, R13 and R14, together with the nitrogen atom to whichthey are attached, form a 4∼8-member heterocyclyl optionally substituted with one or more substituents selectedfrom OH, C1-C6 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, aryl and Het;R15 is H; CF3; C1-C6 alkyl optionally substituted with halogen, OH, C1-C6 alkoxycarbonylamino, NR13R14, NHSO2R16,NHCOR16, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, aryl or Het; (CH2)nCOOR8; (CH2)nCONHR8, where-in n is 0∼6; C2-C4 alkenyl optionally substituted with C1-C6 alkyl, OH, C1-C6 alkoxy or NR13R14; C3-C6 cycloalkyloptionally substituted with C1-C6 alkyl or OH; C3-C6 cycloalkoxy optionally substituted with C1-C6 alkyl or OH; aryl;or Het;R16 is C1-C6 alkyl, aryl or Het;R17 and R18 are each independently H; C1-C6 alkyl optionally substituted with OH, SO3H, SO2NR13R14, SO2R16,PO(OH)2, PO(OR16)2, NR13R14, aryl, Het or 4∼8-member heterocyclyl; C3-C6 cycloalkyl; or aryl optionally substitutedwith OH; or, R17 and R18, together with the nitrogen atom to which they are attached, form a 4∼8-member heterocyclyloptionally substituted with one or more substituents selected from OH, C1-C6 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl,aryl and Het;

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R19 is C1-C6 alkyl, aryl or NHR8;R20 is C1-C3 alkyl;halogen is F, Cl, Br or I;Y is O, S or NR8;

[0011] The said ’aryl’ is phenyl unsubstituted or substituted with one or more substituents selected from halogen,C1-C3 alkyl, C1-C3 alkoxy, CF3, CN and NO2;The said ’5∼7-member heterocyclyl’, ’4∼8-member heterocyclyl’ and ’5-member heterocyclyl’ denote saturated or un-saturated heterocyclyl comprising one or more heteroatoms selected from N, S and O;The said ’Het’ is a 5∼6-member aromatic heterocyclyl comprising 1∼4 heteroatoms selected from N, S and O, the said5∼6-member aromatic heterocyclyl being optionally sutstituted with one or more substituents selected from halogen,C1-C3 alkyl, C1-C3 alkoxy, CF3, CN and NO2.[0012] In a preferred embodiment of the present invention, in formula I:

R1 and R2 are each independently H; C1-C10 alkyl; halogen; CF3; OR5; NHCOR8; aryl; or C1-C4 alkyl optionallysubstituted with aryl, or OR5;Z is OR3;R3 is C1-C6 alkyl or C1-C3 alkyl substituted with C1-C3 alkoxy;R4 is NO2; CN; SO2NR6R7; NR9R10; COR11; OR12; C2-C4 alkyl optionally substituted with OH, C1-C4 alkoxy orNR6R7; or, R4 is a 5- or 6-member heterocyclyl optionally substituted with one or more substituents selected fromOH, COOR8, CONH2, C1-C6 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, aryl, Het and C1-C6 alkyl substituted with OH;or, R4 is a 5- or 6-member monosaccharide group optionally substituted with one or more substituents selected fromC1-C6 alkyl, trimethylsilyl, benzyl and acetyl;R5 is H; C1-C6 alkyl; C1-C4 alkyl optionally substituted with OH, C1-C4 alkoxy or NR6R7; or aryl;R6 and R7 are each independently H, OH, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 alkenyl, C3-C6 cycloalkyl, adamantyl,C3-C8 lactamyl, aryl, Het, or (CH2CH2O)jH wherein j is 1∼3; or R6 and R7 are each independently C1-C6 alkyloptionally substituted with OH, C1-C4 alkoxy, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, NR13R14, aryl,Het or 4∼8-member heterocyclyl; or R6 and R7 are each independently a 4∼8-member heterocyclyl, wherein thesaid 4∼8-member heterocyclyl is furyl, thienyl, thiazolyl, imidazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyrazinyl, mor-pholinyl, thiomorpholinyl, piperidyl, pyrrolidinyl or piperazinyl, and the said 4∼8-member heterocyclyl is optionallysubstituted with one or more substituents selected from OH, COOR8, CONH2, COR16, SO2R16, C1-C6 alkyl, C3-C6cycloalkyl, aryl, Het and C1-C6 alkyl substituted with C1-C4 alkoxy or hydroxy; or R6 and R7, together with the nitrogenatom to which they are attached, form a 4∼8-member heterocyclyl optionally substituted with one or more substituentsselected from OH, COOR8, CONH2, COR16, SO2R16, C1-C6 alkyl, (CH2CH2O)jH wherein j is 1∼3, C3-C6 cycloalkyl,aryl, Het, and C1-C6 alkyl substituted with C1-C4 alkoxy or hydroxyl or aryl; or R6 and R7, together with the nitrogenatom to which they are attached, form glucosylamino group, amino-acid residue, amino-acid ester residue or aminoamide residue, which are optionally substituted with one or more substituents selected from C1-C6 alkyl, NR13R14,COR16, benzyl, benzyloxycarbonyl and t-butyloxycarbonyl;R8 is H, C1-C6 alkyl or aryl;R9 is H, C1-C6 alkyl or SO2R16;R10 is H; C1-C6 alkyl; COR15; SO2R16;

a 5- or 6-member monosaccharide group; or R10 is a 5-member heterocyclyl optionally substituted with one or moresubstituents, wherein the heterocyclyl is dihydroimidazolyl substituted with hydroxyalkyl, or 1,2,4- triazolyl optionallysubstituted with C1-C6 alkyl, aryl or amino group; or when R9 is H, R10 is an amino-acid residue optionally substitutedwith one or more substituents selected from OH, C1-C6 alkyl, C1-C4 alkoxy, COR16, benzyl, benzyloxycarbonyl andt-butyloxycarbonyl;R11 is H; OH; C1-C6 alkyl; aryl; Het; NH(CH2)kNH2, NH(CH2)kNHSO2R , or NH(CH2)kNHCOR16, wherein k is 0∼4;C1-C3 alkyl substitued with halogen, OH or C1-C6 alkoxy; or (CH2)mNR6R7, wherein m is 0∼2; or, R11 is an amino-acid residue or an aminoamide residue optionally substituted with C1-C4 alkoxy;R12 is H, COR19, SO2R16 or a 5-or 6-member monosaccharide group;R13 and R14 are each independently H or C1-C6 alkyl; or, R13 and R14, together with the nitrogen atom to whichthey are attached, form a 4∼8-member heterocyclyl optionally substituted with one or more substituents selectedfrom OH and C1-C6 alkyl;

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R15 is H; CF3; C1-C6 alkyl optionally substituted with halogen, OH, C1-C6 alkoxycarbonylamino, NR13R14, NHSO2R16,NHCOR16, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, aryl or Het; (CH2)nCOOR8, or (CH2)nCONHR8,wherein n is 0∼6; C2-C4 alkenyl optionally substituted with C1-C6 alkyl, OH, C1-C6 alkoxy or NR13R14; C3-C6 cycloalkyloptionally substituted with C1-C6 alkyl or OH; C3-C6 cycloalkoxy optionally substituted with C1-C6 alkyl or OH; aryl;or Het;R16 is C1-C6 alkyl or aryl;R17 and R18 are each independently H; C1-C6 alkyl optionally substituted with OH, SO3H, SO2NR13R14, SO2R16,PO(OH)2, PO(OR16)2, NR13R14, aryl, Het or 4∼8-member heterocyclyl; C3-C6 cycloalkyl; or aryl optionally substitutedwith OH; or, R17 and R18, together with the nitrogen atom to which they are attached, form a 4∼8-member heterocyclyloptionally substituted with one or more substituents selected from OH and C1-C6 alkyl;R19 is C1-C6 alkyl, aryl or NHR8;R20 is C1-C3 alkyl;Halogen is F, Cl, Br or I;Y is O, S or NR8;

[0013] The said ’aryl’ is phenyl unsubstituted or substituted with one or more substituents selected from halogen,C1-C3 alkyl, and C1-C3 alkoxy;The said ’5- or 6-member heterocyclyl’, ’4∼8-member heterocyclyl’, ’5-member heterocyclyl" denote saturated or un-saturated heterocyclyl comprising one or more heteroatoms selected from N, S and O;The said ’Het’ is a 5∼6-member aromatic heterocyclyl comprising 1∼4 heteroatoms selected from N, S and O, the said5∼6-member aromatic heterocyclyl being optionally sutstituted with one or more substituents selected from halogen,C1-C3 alkyl, C1-C3 alkoxy, CF3, CN and NO2.[0014] The said ’amino-acid’ is glycine, alanine, phenylalanine, serine, tryptophane, valine, leucine, isoleucine, t-leucine, tyrosine, lysine, histidine, methionine, arginine, threonine, aspartate, cysteine, proline, glutamic acid, asparagine,glutamine, ornithine or citrulline;The said ’5- or 6-member monosaccharide’ is ribose, deoxyribose, xylose, arabinose, glucose, mannose, galactose orfructose.[0015] In a further embodiment of the present invention, in formula I:

R1 is H, F, Cl, Br, I, -OH, methyl, ethyl, propyl, isopropyl or acetamido;R2 is Br, CF3, OR5, ethyl, propyl, isopropyl, benzylamino, phenyl, benzyl, isobutyl, n-octyl or acetamido;Z is OR3;R3 is ethyl, propyl, n-butyl, n-hexyl or 3-methoxyl propyl;R4 is NO2, SO2NR6R7, NR9R10, COR11, OR12 or glucosyl; or R4 is a 5- or 6-member heterocyclyl, wherein the said5- or 6-member heterocyclyl is thienyl, thiazolyl, 1,2,4-triazolyl, imidazolyl, pyrrolyl, oxadiazolyl, pyrimidinyl, mor-pholinyl, thiomorpholinyl, piperidyl, pyrrolidinyl or piperazinyl, and the said 5- or 6-member heterocyclyl is optionallysubstituted with one or more substituents selected from OH, COOH, CONH2, C1-C6 alkyl, C1-C4 alkoxy, C3-C6cycloalkyl, aryl, Het and C1-C6 alkyl substituted with OH;R5 is H; C1-C4 alkyl optionally substituted with OH, C1-C4 alkoxy or NR6R7; or aryl;R6 and R7 are each independently H, methyl, methoxyl, cyclopropyl, propenyl, isobutyl, t-butyl, adamantyl, cyclohexyl,caprolactamyl, 2-(1-methylpyrrol-2-yl)ethylamino, pyridylmethyl, thienylmethyl,

or C2-C3 alkyl optionally substituted with OH, NR13R14, SO3H, SO2NR13R14 or 5∼6-member heterocyclyl, whereinthe said 5∼6-member heterocyclyl is morpholinyl, thiomorpholinyl, piperidyl, pyrrolidinyl or piperazinyl, and the said5∼6-member heterocyclyl is optionally substituted with one or more substituents selected from OH, COOR8, CONH2,COR16, SO2R16, C1-C6 alkyl and aryl; or R6 and R7, together with the nitrogen atom to which they are attached,form a 5∼6-member heterocyclyl, wherein the said 5∼6-member heterocyclyl is morpholinyl, thiomorpholinyl, piperi-dyl, pyrrolidinyl or piperazinyl, and the said 5∼6-member heterocyclyl is optionally substituted with one or moresubstituents selected from OH, COOR8, CONH2, COR16, SO2R16, C1-C6 alkyl, (CH2CH2O)jH wherein j is 1∼2,dichlorophenyl, benzyl, pyridyl and aryl; or NR6R7 is glucosylamino group, amino-acid residue, amino-acid esterresidue or amino-amide residue, which are optionally substituted with one or more substituents selected fromNR13R14 and acetyl;R8 is H, methyl or ethyl;

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R9 is H, methyl or SO2R16;R10 is H, methyl, COR15, SO2R16,

glucosyl or mannosyl; dihydroimidazolyl substituted with hydroxyethyl; or when R9 is H, R10 is an amino-acid residueoptionally substituted with one or more selected from OH, t-butyloxycarbonyl, and acetyl;R11 is OH, pyrazolyl substituted with isopropyl; aminoamide residue; amino-ester residue; NR6R7; CH2Br orCH2NR6R7;R12 is H, COR19, SO2R16, mannosylorglucosyl;R13 and R14 are each independently H or ethyl; or, R13 and R14, together with the nitrogen atom to which they areattached, form a 5∼6-member heterocyclyl, wherein the said 5∼6-member heterocyclyl is morpholinyl, piperidyl,pyrrolidinyl or piperazinyl, and the said 5∼6-member heterocyclyl is optionally substituted with one or more substit-uents selected from OH and C1-C6 alkyl;R15 is H; methyl; ethyl; cyclohexyl; CF3; (CH2)nCOOR8, or (CH2)nCONH2, wherein, n is 0 or 1; vinyl; propenyl;pyridyl; phenyl substituted with ethoxy; or thiazolyl substituted with isopropyl;R16 is methyl;R17 and R18 are each independently H, ethyl or phenyl; or R17 and R18 together with the nitrogen atom to whichthey are attached, form a 4∼8-member heterocyclyl, wherein the said 4∼8-member heterocyclyl is morpholinyl,piperidyl, pyrrolidinyl or piperazinyl, and the said 4∼8-member heterocyclyl is optionally substituted with one or moresubstituents selected from OH and C1-C6 alkyl; or when Y is NH, R17 and C(Y)N form a dihydroimidazolyl;R19 is methyl or NHC2H5;R20 is methyl;Halogen is F, Cl, Br or I;Y is O, S, NH or NC2H5.

[0016] The said ’aryl’ is phenyl unsubstituted or substituted with one or more substituents selected from halogen,C1-C3 alkyl, and C1-C3 alkoxy;The said ’Het’ is a 5∼6-member aromatic heterocyclyl comprising 1∼4 heteroatoms selected from N, S and O, the said5∼6-member aromatic heterocyclyl being optionally sutstituted with one or more substituents selected from halogen,C1-C3 alkyl, C1-C3 alkoxy, CF3, CN and NO2.[0017] The said ’amino-acid’ is glycine, alanine, phenylalanine, serine, tryptophane, valine, leucine, isoleucine, t-leucine, tyrosine, lysine, histidine, methionine, arginine, threonine, aspartate, cysteine, proline, glutamic acid, asparagine,glutamine, ornithine or citrulline;The said ’5- or 6-member monosaccharide’ is glucose or mannose.[0018] In another further preferred embodiment of the present invention, the phenylpyrimidone compound of formulaI, pharmaceutically acceptable salts or solvates thereof are selected from the following compounds:

6-isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,6-hydroxy-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-acetamido-6-hydroxy-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,6-phenyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-acetamido-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3 H)-one,6-acetamido-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3 H)-one,5 -bromo-6-isopropyl-2- [2-n-propoxyl-5 -(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3 H)-one,6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-chloro-6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-acetamido-6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4( 3H)-one,5-bromo-6-isopropyl-2-[2-n-butoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H )-one5-bromo-6-n-octyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3 H)-on e,5-bromo-6-phenyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3 H)-on e,5-methyl-6-isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4( 3H)-one,5-fluoro-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-o ne,

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5-methyl-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-hydroxy-6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H )-one,5-bromo-6-isopropyl-2-[2-n-hexyloxy-5-(4-methyl-l-piperazinylsulfonyl)phenyl]pyrimid-4( 3H)-one,5-bromo-6-isobutyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3 H)-o ne,5-bromo-6-isopropyl-2-{2-n-propoxyl-5-[N-methyl-N-(2-hydroxyethyl)aminosulfonyl]pheny l}pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-{2-n-propoxyl-5-[N-(2-morpholinoethyl)aminosulfonyl]phenyl}pyri mid-4(3H)-one,5-bromo-6-isopropyl-2-{2-n-propoxyl-5-[N-(3-morpholinopropyl)aminosulfonyl]phenyl}pyr imid-4(3H)-one,5-bromo-6-isopropyl-2-{2-n-propoxyl-5-[N-(N’,N’-diethylamino)ethylaminosulfonyl]phenyl }pyrimid-4(3H)-one,5,6-diethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one, 5,6-diethyl-2-{2-n-pro-poxyl-5-[N-methyl-N-(hydroxyethyl)aminosulfonyl]phenyl}pyrimid-4 (3H)-one,5,6-diethyl-2-{2-n-propoxyl-5-[N-(2-ethylaminoethyl)aminosulfonyl)phenyl}pyrimid-4(3H)-one,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylsulfonylproline,2-(5-nitro-2-n-propoxyphenyl)-5-bromo-6-isopropylpyrimid-4(3H)-one,2-(5-amino-2-n-propoxyphenyl)-5-bromo-6-isopropylpyrimid-4(3H)-one,1 -(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylthi ourea,1-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-3-ethyl-2-methylisothiourea,N-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’, N"-triethylguanidine,N-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-piperidyl-1-formamidine,N-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-pyrrolyl-1-formamidine,2-{2-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]amino-4,5-dihydro-imidazol-1-yl}-ethanol,2-(5-nitro-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one,2-(5-amino-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylthiourea,1-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-3-ethyl-2-methyliso thiourea,N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-piperidyl-1 -formamidine,,N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’,N"-triethyl guanidine,2-{2-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]amino-4,5-dihydr o-imidazol-1-yl}-ethanol,N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-pyrrolyl-1 - formamide,N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-pyrrolyl-1-formami dine,5-bromo-6-isopropyl-2-(2-n-propoxyl-5- mesylamidophenyl)pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5- mesylamidophenyl)pyrimid-4(3H)-one,N-(3-(1,6-dihydro-4-isopropyl-5-bromo-6-oxopyrimidin-2-yl)-4-propoxyphenyl)acetamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)acetamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)propionamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)cyclohexamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)formamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)-1-t-butyloxycarbonyl -4-hydroxy-prolylamide,4-n-propoxyl-3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)benzoic acid,(morpholin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzopheno ne,(piperid-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,(2-aminoformylpyrrol-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)b enzophenone,4-n-propoxyl-3-(1,6-dihydro-4-isopropyl-6-oxopyrimidin-2-yl)benzoic acid,(morpholin-1-yl)(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)be nzophenone,(piperid-1-yl)(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benz ophenone,(4-methyl-piperazin-1-yl)(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-y!)-4-n-pro poxyl)benzophenone,2-(5-(N,N-dimethylamino-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylurea,1-(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-phenylt hiourea,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-guanidine,5-bromo-6-isopropyl-2-(5-(2-bromoacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-(5-(2-morpholinylacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-(5-(2-(4-methyl-piperazin-1-yl)acetyl)-2-n-propoxyphenyl)pyrimid-4 (3H)-one,5,6-diethyl-2-(5-(2-bromoacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,5,6-diethyl-2-(5-(2-(4-methyl-piperazin-1-yl)acetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,5,6-diethyl-2-(5-(2-morpholinylacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-(2-n-propoxyl-5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H -pyran-2-ylamino)phe-

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nyl)pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-(2-n-propoxyl-5-(tetrahydro-3,4-dihydroxy-5-(1,2-dihydroxyethyl)fur -2-ylamino)phenyl)py-rimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(tetrahydro-3,4-dihydroxy-5-(1,2-dihydroxyethyl)fur-2-ylamin o)phenyl)pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H pyran-2-y lamino)phenyl)pyrimid-4(3H)-one,2-(5-hydroxy-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one,(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl) acetate,(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl) ethylaminoformate,5,6-diethyl-2-(2-n-propoxyl-5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-y loxy)phenyl)pyrimid-4(3H)-one,(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl) mesylate,2-(5-(2,5-dimethyl-1H-pyrrol-1-yl)-2-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one,2,2’-(4-n-propoxyl-1,3-phenylene)bis(5,6-diethylpyrimid-4(3H)-one),2-(5-(1,3,4-oxadiazol-2-yl)-2-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one,ethyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)acetate,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-morpholinylethyl)-4-n-propoxybenza mide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N,N-di(2-hydroxyethyl)-4-n-propoxybenza mide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-caprolactam-3-yl)-4-n-propoxybenza mide,(4-(2,3-dichlorophenyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,(3-isopropylpyrazol-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)ben zophenone,N-cyclohexyl-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,N-((pyrid-2-yl)methyl)-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzam ide,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3,3-dimethylbutyrat e,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2,2,2-trifluoro acetamide,ethyl N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformylformate,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)acrylamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-crotonamide,ethyl N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformylacetate,2-ethoxyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)benzamid e,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)nicotinamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-5-isopropylthiazoly 1-2-formamide,t-butyl 3-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformyl)propyl amino formate,4-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)butyra mide ,1-acetyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)pyrrolidiny l-2-formamide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-met hylbutyramide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-phe nylpropionamide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)propio namide,2,6-diacetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)hex anamide,N1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)propanediamide,N1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)oxalamide,N-(aminoformylmethyl)-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenza mide,5,6-diethyl-2-{2-n-propoxyl-5-[(2-(1-methylpyrrol-2-yl)ethyl)aminosulfonyl]phenyl{pyrimid -4(3H)-one,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-(1-methylpyrrol-2-yl)ethyl)-4-n-propo xylbenzamide,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5 -ureapentanoic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5 -aminopentanoic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3 -methylbutyric acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopr opanoic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3 -hydroxypropanoic acid,ethyl 2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropi onate,3-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopr opylsulfonic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminoet hylsulfonic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3 -aminoformylpropanoicacid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3 -indolepropionic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminoac etic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3 ,3-dimethylbutyric acid,

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2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-4 -aminoformylbutyric ac-id,ethyl 2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-me thylvalerate,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylsulfonamido)-6-acetamid ocaproate,5,6-diethyl-2-(2-n-propoxyl-5-(4-hydroxyethyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(3-hydroxypropylaminosulfonyl)phenyl]pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(N-(2-morpholinylethyl)-N-(2-hydroxyethyl)aminosulfonyl)ph enyl)pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(N-methyl-N-(2-(pyrrolidin-l-yl)ethyl)aminosulfonyl)phenyl) pyrimid-4(3(-H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(2-(N,N-diethyl)aminoethylaminosulfonyl)phenyl]pyrimid-4(3 H)-one maleate,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phenylpropan oic acid,methyl N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzoylprolinate,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-(4-hydroxyphen yl)propionate,ethyl 2-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-(1H-indol-3-yl)pr opionate,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-methyl butyrate,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-(1H-imidazol-4-yl)propionate,ethyl 2-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-methylvalerate,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)propionic acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-aminoformyl propionic acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-4-aminoformyl butyric acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-hydroxypropi onic acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-guanidinopen tanoic acid,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phenylpropionatemethyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propionate,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-4-methylvalerate,ethyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propionate,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-(4-methylpiperazin-1-yl)-1-oxopropan -2-yl)-4-n-propoxyben-zamide,N-(1-aminoformylethyl)-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenza mide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl-N-(2-(thien-2-yl)ethyl)benza mide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl-N-((fur-2-yl)methyl)benzami de,N-t-butyl-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-isobutyl-4-n-propoxylbenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-allyl-4-n-propoxylbenzamide,(4-(pyrid-2-yl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl benzophenone,(4-(hydroxyethyloxylethyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophe-none,(4-(hydroxyethyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propo xylbenzophenone,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(3-hydroxypropyl)-4-n-propoxylbenzami de,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-hydroxy-2-propyl)-4-n-propoxybenza mide,N-ethyl-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-hydroxyethyl)-4-n-propoxylb enzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-diethylaminoethyl)-4-n-propoxylbenz amide,3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propyl-1-sulfoni c acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)ethylsulfonic acid,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-hydroxyethyl)-N-methyl-4-n-propoxyl benzamide,(4-benzylpiperazin-1-yl)(3-(4, 5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenz ophenone,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-methyl-N-(2-(pyrrolidin-1-yl)ethyl)-4-n-propoxybenzamide,methyl 5-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido )piperidyl-2-form ate,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-methoxyl-N-methyl-4-n-propoxybenzam ide,5,6-diethyl-2-[2-(3-methoxyln-propoxyl)-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,2-chloro-N-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)acetamide,2-(dimethylamino)-N-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)a cetamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-(4-methylpiperaz in-1-yl)acetamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-morpholinyl)acet amide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-(piperid-1-yl)acet amide,dimethyl (3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylaminoformyl)methylphosp hate,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)isobutyramide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-methylbutyramid e,

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N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-phenylacetamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)benzamide,ethyl 3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylaminoformyl) propionate,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-5-oxopyrrolidinyl-2-formamide,2-acetamido-N-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-4-meth ylpentanamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-acetamido-3-(1H -indol-3-yl)propiona-mide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl) glutaramide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-hyd roxybutyramide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-hyd roxypropionamide,-(2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylaminoformyl)-2-ace tamidoethyl)acetate,5,6-diethyl-2-(5-(ethylamino)-2-n-propoxyphenyl)pyrimid-4(3H)-one,N-ethyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)propionami de,ethyl (N-ethyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformylf ormate,1,3-diethyl-1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)piperidyl-1-formami de,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-4-methylpiperaziny 1-1-formamide,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-propylurea,1-cyclohexyl-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea,1,1-diethyl-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea,1-(2-(diethylamino)ethyl)-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyp henyl)urea maleate,(4-methylpiperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenz ophenone,5-iodo-6-isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl] pyrimid-4(3H )-one,5-chloro-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-((tetrahydro-2,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-3-ylamino)sulfonyl)phe-nyl]pyrimid-4(3H)-one,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-urea pentanoic acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-aminopentan oic acid,3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(tetrahydro-2,4,5-trihydroxy-6-(hydro xymethyl)-2H-pyran-3-yl)-4-n-propoxybenzamide,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)ethylsulfamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-methyl-piperazin-1-ylsulfonylethyl)-4 -n-propoxybenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylethyl)-4-n-pro poxybenzamide,3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propylsulfamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-methyl-piperazin-1-yl sulfonylpropyl)-4-n-propoxybenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylpropyl)-4-n-p ropoxybenzamide,5,6-diethyl-2-(5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yl)-2-n-propox yphenyl)pyrimid-4(3H)-one,5-iodo-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on e,5-bromo-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one, and5-chloro-6-isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3 H)-one.

[0019] In the best embodiment of the present invention, the said phenylpyrimidone compound of formula I, pharma-ceutically acceptable salts or solvates thereof are selected from the following compounds:

5,6-diethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5,6-diethyl-2-{2-n-propoxyl-5-[N-(2-morpholinylethyl)aminosulfonyl)phenyl}pyrimid-4(3H )-one,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylsulfonylproline,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylthiourea,N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’, N"-triethyl guanidine,N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-pyrrolyl-1-formami de,5-bromo-6-isopropyl-2-(2-n-propoxyl-5-mesylamidophenyl)pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-mesylamidophenyl)pyrimid-4(3H)-one,N-(3-(1,6-dihydro-4-isopropyl-5-bromo-6-oxopyrimidin-2-yl)-4-propoxyphenyl)acetamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)acetamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)propionamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)cyclohexamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)-1-t-butyloxycarbonyl -4-hydroxy-prolylamide,

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(morpholin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzopheno ne,(piperid-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,(2-aminoformylpyrrol-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)b enzophenone,(morpholin-1-yl) (3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylurea,5,6-diethyl-2-(5-(2-morpholinylacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,2,2’-(4-n-propoxyl-1,3-phenylenyl)bis(5,6-diethylpyrimid-4(3H)-one),ethyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)acetate,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2,2,2-trifluoroaceta mide,ethyl N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformylacetate,4-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)butyra mide,1-acetyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)pyrrolidiny 1-2-formamide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-phe nylpropionamide,N1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl) oxalamide,5,6-diethyl-2-{2-n-propoxyl-5-[(2-(1-methylpyrrol-2-yl)ethyl)aminosulfonyl]phenyl}pyrimid -4(3H)-one,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-(1-methylpyrrol-2-yl)ethyl)-4-n-propo xylbenzamide,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5 -urea pentanoic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5 -aminopentanoic acid,ethyl 2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropi onate,3-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopr opylsulfonic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminoet hylsulfonic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3 -aminoformylpropanoicacid,5,6-diethyl-2-(2-n-propoxyl-5-(4-hydroxyethyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(N-(2-morpholinylethyl)-N-(2-hydroxyethyl)aminosulfonyl)ph enyl)pyrimid-4(3H)-one,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phenylpropan oic acid,methyl N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzoylprolinate,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-(4-hydroxyphen yl)propionate,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)propanoic acid,2-(3-(4.,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-aminoformyl propanoic acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-guanidinopen tanoic acid,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimi din-2-yl)-4-n-propoxybenzamido)-3-phenylpropanoic acid,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propanoic acid,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-(4-methylpiperazin-1-yl)-1-oxopropan -2-yl)-4-n-propoxyben-zamide,N-(1-aminoformylethyl)-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenza mide,(4-(hydroxyethyoxylethyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4 -n-propoxylbenzophe-none,(4-(hydroxyethyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propo xylbenzophenone,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-hydroxy-2-propyl)-4-n-propoxybenza mide,3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propyl-1-sulfoni c acid,methyl 5-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)piperidinyl-2-format e,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-(4-methylpiperaz in-1-yl)acetamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)benzamide,1-(2-(diethylamino)ethyl)-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyp henyl)urea maleate,(4-methylpiperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenz ophenone,5,6-diethyl-2-(2-n-propoxyl-5-((tetrahydro-2,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran -3-ylamino)sulfonyl)phe-nyl]pyrimid-4(3H)-one,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-urea pentanoic acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-aminopentan oic acid,3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(tetrahydro-2,4,5-trihydroxy-6-(hydro xymethyl)-2H-pyran-3-yl)-4-n-propoxybenzamide,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)ethylsulfamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-methyl-piperazin-1-ylsulfonylethyl)-4 -n-propoxybenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylethyl)-4-n-pro poxybenzamide,3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propylsulfamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-methyl-piperazin-1-ylsulfonylpropyl)-4-n-propoxybenzamide,

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3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylpropyl)-4-n-p ropoxybenzamide, and5,6-diethyl-2-(5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yl)-2-n-propox yphenyl)pyrimid-4(3H)-one.

[0020] In the above definitions, unless indicated specifically, alkyl or alkoxy with 3 or more carbon atoms can be straightor branched.[0021] The compound of formula I can have one or more chiral sites, so it can have stereoisomers, i.e. enantiomers,diastereoisomers or the mixture thereof. If the compound of formula I contains an alkenyl or an alkenylene, it can furtherexist cis(E)-trans(Z) isomerism. Accordingly, the compound of formula I according to the present invention can be asingle isomer or the mixture of various isomers.[0022] The separation of diastereoisomers or cis- and trans-isomers can be achieved by using the common technol-ogies, for example, the fractional crystallization, chromatography or HPLC of the stereoisomeric mixture of the compoundof formula I, the acceptable salts or derivatives of thereof. The compound of formula I can also be prepared from thecorresponding optically pure intermediates; or by the resolution of the corresponding racemoids using a suitable chiralvector, for example, by separating the diastereoisomeric salts generated by reacting the corresponding racemoid witha suitable optically active acid or base through HPLC or fractional crystallization.[0023] The compound of formula I can have tautomers, and the present invention also includes a single tautomer orthe mixture thereof.[0024] The present invention includes the radiolabelled derivatives of the compound of formula I, which are suitablefor bioresearch.[0025] The present invention provides the pharmaceutically acceptable salts of the compound of formula I having analkaline center, for example, a nontoxic acid addition salt formed with an inorganic acid such as hydrochloric acid,hydrobromic acid, hydroiodic acid, sulphuric acid and phosphoric acid, or with an organic carboxylic acid or an organicsulfonic acid. The compound of formula I can also react with a base to produce a pharmaceutically acceptable metalsalts, especially a nontoxic alkali metal salt such as sodium salt and potassium salt. Prefered are methanesulphonateand hydrochlorate.[0026] The present invention includes any prodrug of the compound of formula I.[0027] The present invention also includes the pharmaceutically acceptable solvates of the compound of formula I,such as hydrate (here are the solvates of formula I).[0028] The present invention still includes the pharmaceutically acceptable oxides of the compound of formula I, andpharmaceutically acceptable salts and solvates thereof (here are the salts and solvates of the pharmaceutically accept-able oxide).[0029] The present invention still includes various crystal forms of the compound of formula I and the salts thereof.[0030] The present invention also provides a process for preparing the phenylpyrimidone compound of formula I,pharmaceutically acceptable salts or solvates thereof, wherein the process comprises:

(1) when R4 is OH, SO2NR6R7, COR11, unsubstituted or substituted C2-C4 alkyl, unsubstituted or substituted C2-C4alkenyl, or unsubstituted or substituted 5~7-member heterocyclyl, the compound of formula I can be obtained bycyclization of the compound of formula II with the compound of formula III in the presence of a base, wherein R1,R2, R3, R6, R7, R11 and the said 5~7-member heterocyclyl are defined the same as the above. The reaction iscommonly performed at a temperature within the range of 50 °C to 120 °C. The solvent is preferably selected fromthe group consisting of chloroform, methanol, ethanol, ethylene glycol monomethyl ether, N,N-dimethylformamideand dioxane. The reaction time is with in the range of 0.5-10 h, and the said base is preferably K2CO3 or NaOC2H5;

or,(2) the compound of formula I can be obtained by conversion of the compound of formula Ia, the compound offormula Ie or other compounds of formula I, wherein R1, R2, R3, R5, R6, R7, R8, R9, R10, R12, R15, R16, R17, R18,R19 and R20 are defined the same as the above, wherein the method of preparing the compound of formula Ia refersto the above said Method (1), and the compound of formula Ie (which is a known compound) can be obtained by

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bromination of the compound of formula Ia, wherein,

1) when R4 is SO2NR6R7, the compound of formula Ib can be prepared from the compound of formula Ia throughchlorosulfonating followed by reacting with R6R7NH in the presence of a base, such as pyridine or triethylaminein a suitable organic solvent, such as tetrahydrofuran, or dichlormethane;

or,2) when R4 is NO2, the compound of formula Ic can be prepared by nitrating the compound of formula Ia, whereinthe nitrating reagent can be a mixture of concentrated nitric acid and concentrated sulfuric acid;

or,3) when R4 is NH2, the compound of formula Id can be prepared by reduction of the compound of formula Ic,for example, by using a traditional catalytic hydrogen reduction wherein Raney-Ni or Pd/C is used as the catalyst,or by using reduced iron powder in an acid condition (e.g. concentrated hydrochloric acid is used as the solvent)at a suitable temperature (20-100 °C);

or,4) when R4 is CN, the compound of formula If can be prepared from the compound of formula Ie by nucleophilicsubstitution with a cyanide such as CuCN in a suitable solvent (e.g. N,N-dimethylformamide) at a suitabletemperature (e.g. 70-160 °C);

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or,5) when R4 is COOH, the compound of formula Ig can be prepared from the compound of formula If by hydrolysisin the presence of a base (e.g. 2N NaOH in water);

or,6) when R4 is NR9R10, the compound of formula I can be prepared from the compound of formula Id whereinR4 is NH2, wherein,

1> when R9 and R10 are simultaneouly methyl, the compound of formula I can be prepared through N-methylation by using paraformaldehyde as a methylating agent with formic acid as a solvent at a suitabletemperature (e.g. 80°C);2> when R9 is H and R10 is SO2R16, the compound of formula I can be prepared from the compound offomula Id through sulfonylation in the presence of a base (e.g. pyridine or triethylamine) in a suitable organicsolvent (e.g. tetrahydrofuran, dichloromethane), wherein the sulfonylating agent is preferably a sulfonylhalide (e.g. methylsulfonyl chloride).3> when R9 is H and R10 is COR15, the compound of formula I can be prepared by firstly reacting an organicacid with oxalyl chloride or thionyl chloride to give an acyl chloride in a suitable organic solvent (e.g. tet-rahydrofuran, dichloromethane), followed by reacting the resulting acyl chloride with the compound of fomulaId; or by condensing the compound of fomula Id with an organic acid (e.g.formic acid, cyclohexanecarboxylicacid) in the presence of a coupling agent (e.g. 1,3-dicyclohexylcarbodiimide (DCC) or 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide (EDCI)) and an activator (e.g. 1-hydroxy-benzo-triazole (HOBT));4> when R9 is H, R10 is C(Y)NR17R18, and Y is O or S, the compound of formula I can be prepared by theaddition reaction of the compound of fomula Id with a compound of formula Y=C=NR17R18 in a suitablesolvent (e.g. ethanol) at a suitable temperature (e.g. 50-80°C);5> when R9 is H, R10 is a 5- or 6-member monosaccharide group, the compound of formula I can beprepared by reacting the compound of fomula Id with a unprotected 5- or 6-member monosaccharide inthe presence of a trace amount of an organic acid (e.g. glacial acetic acid) as a catalyst in a suitable solvent(e.g. ethanol, ethylene glycol monomethyl ether, N,N-dimethylformamide, n-butyl alcohol) at a suitabletemperature (e.g. 50-150°C);6> when R9 is H, R10 is

, and Y is NR8, the compound of formula I can be prepared by a nucleophilic substitution of the compoundof fomula Ih with a compound of formula R17NHR18 in a suitable solvent (e.g. ethanol, ethylene glycolmonomethyl ether, N,N-dimethylformamide, n-butyl alcohol) at a suitable temperature (e.g. 50-150°C),wherein the compound of formula Ih can be prepared by the addition reaction of the compound of fomulaIi with iodomethane in a suitable solvent (e.g. methanol, ethanol, tetrahydrofuran) at a suitable temperature(e.g. 40-80°C), and the compound of formula Ii can be prepared by the addition reaction of the compoundof fomula Id with R8SCN in a suitable solvent (e.g. methanol, ethanol, tetrahydrofuran, acetic acid andwater) at a suitable temperature (e.g. 40-80°C);

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7> when R9 is H and R10 is an amino acid residue substituted with acetyl, the compound of formula I canbe prepared by firstly condensing the compound of fomula Id with a N-Boc protected amino acid in anorganic solvent including tetrahydrofuran or dichloromethane in the presence of a coupling agent including1,3-dicyclohexylcarbodiimide or 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and an activator such as1-hydroxy-benzo-triazole to give an intermediate, then deprotecting Boc group in trifluoroacetic acid, andfinally reacting with acetic anhydride in pyridine; or,

7) when R4 is COR11 and R11 is NR6R7, the compound of formula I can be prepared by condensing the compoundof fomula Ig with R6R7NH with a coupling agent being preferably 1,3-dicyclohexylcarbodiimide (DCC) or 1-(3-dimethylamino propyl)-3-ethylcarbodiimide (EDCI); or by transforming the compound of fomula Ig into an cor-responding acyl chloride derivative, followed by reacting with R6R7NH;or,8) when R4 is COR11 and R11 is CH2NR6R7, the compound of formula I can be prepared by condensing thecompound of fomula Ij with R6R7NH in the presence of an organic base, wherein the said organic base ispreferably pyridine or triethylamine; the compound of fomula Ij can be prepared by bromizing the compound offomula Ik, wherein the bromination reagent is preferably bromine or N-bromosuccinimide (NBS); the compoundof fomula Ik can be prepared by reacting the compound of fomula Ia with vinyl n-butyl ether in the presence ofan metal catalyst(e.g. palladium acetate), followed by hydrolysis in a diluted hydrochloric acid; or the compoundof fomula Ij can also be prepared by Friedel-Crafts reaction of the compound of fomula Ia with bromoacetylbromide using excess AlCl3 as Lewis acid, wherein the reaction solvent is preferably dichloromethane;

or,9) when R4 is OR12, the compound of formula I can be prepared from the compound of fomula I1 through atraditional chemosynthesis method, wherein,

1> when R12 is COR19 and R19 is C1-C6 alkyl or aryl, the compound of formula I can be prepared by esterifingthe compound of fomula I1 wherein R4 is OH in a suitable solvent (e.g. tetrahydrofuran, dichloromethane)in the presence of an organic base (e.g. pyridine or triethylamine);2> when R12 is COR19 and R19 is NHR8, the compound of formula I can be prepared by addition reactionof R8NCO with the compound of fomula I1 wherein R4 is OH;3> when R12 is SO2R16, the compound of formula I can be prepared by sulfonylation of the compound offomula I1 wherein R4 is OH in the presence of an organic base (e.g. pyridine or triethylamine) in a suitablesolvent (e.g. tetrahydrofuran, dichloromethane), and the sulfonylating reagent is preferably a sulfonyl halide(e.g. mesyl chloride);4> when R12 is a 5- or 6-member monosaccharide group, the compound of formula In can be prepared byfirstly condensing the compound of fomula I1 with a 5- or 6-member monosaccharide activated with trichlo-roacetonitrile and protected at hydroxyl by a protecting group such as tetraacetyl, under the catalysis ofLewis acid (e.g. boron trifluoride diethyl ether) according to the method of Schmidt et al. (Angew. Chem.,1980, 92, 763-764) to give the compound of formula Im, followed by hydrolysis under an alkaline condition

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to remove the acetyl protective group;

or,

10) when R4 is pyrrolyl, the compound of formula Io can be prepared by condensing 2,5-hexanedione with thecompound of formula Id where R4 is NH2 in the presence of an organic acid, wherein the said organic acid ispreferably acetic acid and typically the reaction solvent is preferably ethanol;

or,11) when R4 is a glycoside, the compound of formula I can be prepared by firstly reacting the compound offormula Ie where R4 is Br with n-BuLi, then reacting with a glucolactone protected by a protective group (e.g.trimethylsilicane), followed by reduction by using a reducing agent (e.g. triethylsilicane).

or,(3) the compound of formula I can also be prepared by converting other compounds of formula I where R1 is adifferent substituent, wherein R2, R3 and R4 are defined the same as the above, wherein,

1) when R1 is halogen, the compound of formula Iq can be prepared by halogenating the compound of formulaIp where R1 is H in the presence of an organic base, wherein the said organic base is preferably pyridine, thehalogenating agent is preferably elementary halogen, e.g. chlorine gas, liquid bromine, and the reaction solventis preferably dichloromethane;

or,2) when R1 is NH2, the compound of formula Is can be prepared by hydrolyzing the compound of formula Irwherein R1 is acetamido under a strong acidic condition, wherein the reaction solvent is preferably concentratedhydrochloric acid, and the reaction temperature is typically 90~110°C.

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[0031] The present invention also includes the new intermediates during the preparation of the compound of formulaI and the preparation process thereof, for example, the compounds of formulae III, V and Ia, and the preparation processesthereof.

[0032] The compound of formula III can be prepared from the compound of formula IV and lithium bis(trimethylsi-lyl)amide(LiN(Si(CH3)3)2) in tetrahydrofuran(THF), according to the method of Schmidt et al. (Angew. Chem., 1980, 92,763-764).

[0033] The compound of formula III can also be prepared by firstly reacting the compound of formula IV with hydrox-ylamine hydrochloride in a suitable solvent (e.g. a mixture of water and methanol) at a suitable temperature (e.g. 40-80°C)according to the method of Juby et al. (US4031093), to give a compound of formula V, followed by hydrogenation inacetic acid solution at a suitable temperature (e.g. 60°C) under a suitable hydrogen presure (1~5MPa), wherein Pd/Cis used as the catalyst for the reduction.

[0034] The compounds of formulae II and IV are commercially available from Sinopharm Chemical Reagent Co. Ltd,and if unavailable, they can be prepared according to the methods in literatures.[0035] In addition, the present invention also provides a pharmaceutical composition with inhibition activity for PDE5containing a therapeutically effective dose of the compound of formula I, the pharmaceutically acceptable salts or solvatesthereof.[0036] The said pharmaceutical composition comprises a therapeutically effective dose of one or more compounds

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of formula I (or the pharmaceutically acceptable salts thereof, or their pharmaceutically acceptable solvates) and at leastone pharmaceutically acceptable auxiliary. The said pharmaceutically acceptable auxiliary can be selected accordingto the administration route and action mechanism, and is commonly selected from filler, diluent, adhesive, wetting agent,disintegrating agent, lubricant, emulsifier, suspending agent, etc.[0037] The pharmaceutical composition of the present invention can be administered orally, by injection (intravenously,intramuscularly, hypodermically and intracoronary), sublingually, buccally, rectally, urethrally, vaginally, intranasally,inhalationally or by local administration. Prefered are oral administration.[0038] The above composition comprises 0.1%~99.9 wt%, preferably 1%~99 wt% of the compound of formula I, thepharmaceutically acceptable salts or solvates thereof, based on the total weight of the composition.[0039] The present invention also provides a process for preparing the pharmaceutical composition comprising thecompound of formula I, the pharmaceutically acceptable salts or solvates thereof. Typically, the compound of formulaI, the pharmaceutically acceptable salts or solvates thereof are mixed with pharmaceutically acceptable auxiliaries andformulated into a dosage form (formulation) suitable for a certain administration route by a common formulating method.The said formulation includes tablet, capsule, granule, pill, solution, suspension, emulsion, paste, pellicle, cream, aerosol,injection, suppository, preferably tablet and capsule.[0040] The formula of the tablet and capsule can comprise a therapeutically effective dose of one or more compoundsof formula I, the pharmaceutically acceptable salts, or solvates thereof, and one or more usually used auxiliaries, forexample, a filler such as starch, sucrose, lactose, glucose, microcrystalline cellulose, mannose; an adhesive such ascarboxymethylcellulose, gelatin, alginate and polyvinyl pyrrolidone; a wetting agent such as glycerine; a disintegrantsuch as agar, ethylcellulose, sodium carboxymethylstarch, calcium carbonate; a lubricant such as magnesium stearate,talc powder, polyglycol.[0041] The compound according to the present invention is typically administered in an amount of 1~500mg, preferably10~100mg per day, in a single or multiple administration. However, if necessary, the above dose can be suitably deviated.A skilled person in the art can determine the optimum dose according to the professional knowledge and specific situationsincluding the severity of the disease, the individual difference of a patient, the characteristics of a formulation and theadministration route.[0042] Besides, the present invention further provides the compound of formula I, the pharmaceutically acceptablesalts or solvates thereof, or compositions thereof for use in preparing-as a human drug.[0043] The present invention further provides the compound of formula I, the pharmaceutically acceptable salts orsolvates thereof for use in preparing a human drug as a PDE5 inhibitor.[0044] The present invention further provides the compound of formula I, the pharmaceutically acceptable salts orsolvates thereof, or compositions thereof for use in preparing a human drug for treating or preventing male erectiledysfunction, benign prostatic hyperplasia, female sexual dysfunction, premature delivery, menorrhalgia, bladder outletobstruction, incontinence, instable and variant Prinzmetal angina pectoris, hypertension, pulmonary hypertension, con-gestive heart failure, renal failure, atherosclerosis, apoplexy, peripheral vascular diseases, Raynaud’s diseases, inflam-mation diseases, bronchitis, chronicity asthma, allergic asthma, allergic coryza, glaucoma or diseases characterized byenterokinesia dysfunction (e.g. irritable bowel syndrome).[0045] The present invention further provides the compound of formula I, the pharmaceutically acceptable salts orsolvates thereof, or compositions thereof in combination with other drugs for use in treating or preventing diseases suchas male erectile dysfunction, benign prostatic hyperplasia, for example, in combination with a selective 5-hydroxytryp-tamine(5-HTA) reuptake inhibitor for treating prospermia; in combination with an α-acceptor retarder for treating maleerectile dysfunction(ED) combined with benign prostatic hyperplasia (BPH); in combination with an antihypertensivedrug for treating ED combined with hypertension; in combination with propionyl-L-carnitine (Levocarnitine, PLC) fortreating diabetic ED; in combination with testosterone undecanoate for treating the penile erection dysfunction of apatient suffering from ED combined diabetes; in combination with Tianeptine for effectively treating depression combinedwith sexual dysfunction.[0046] The compound of formula I, the pharmaceutically acceptable salts or solvates thereof have an inhibition activityfor PDE5. It is more important that most of these compounds have a stronger inhibition activity for PDE5 than Sildenafil,and have a higher selectivity for PDE6 distributed in retinal. Accordingly, the compounds provided by the present inventioncan be expected to show better clinical safety and effectivity, and thus possess a broad prospect of clinical application.

BEST MODE FOR CARRIYING OUT THE INVENTION

Preparation Examples and Examples

[0047] The following examples will further illustrate the process for preparing the compounds of the present inventionand the intermediates thereof. -1H NMR was completed on a Mercury-400 or Mercury-300 NMR spectrometer(VarianCompany). Common abbreviations are as follow: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; br, broad peak.

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Preparation Example 1

2-n-Propoxy-5-(4-methylpiperazin-1-yl)sulfonylbenzonitrile

[0048]

2-n-propoxybenzonitrile(32.2g, 0.2mol) was slowly added into chlorosulfonic acid(120ml) under ice-bath. The ice bathwas removed, and after stirred for 2h at room temperature, the reaction mixture was added dropwise in brash ice carefullyto generate a lot of precipitate. After filtered, the precipitate was washed with ice water, dissolved in CH2Cl2(300ml),and added dropwise into methylpiperazidine (19.8g, 0.2mol) dissolved in CH2Cl2(250ml) under ice-bath. After the ad-dition, the stirring continued for 30 min. The resulting organic phase was washed with water(33200ml) and saturatedbrine(100ml). After solvent was evaporated to dryness, the residue was recrystallized in ethyl acetate/petroleum etherto afford the title compound(48.5g, total yield of the two steps: 75%). 1H NMR (DMSO-d6) δ: 8.05 (1H, dd), 7.77 (1H, t),7.36 (1H, d), 4.15 (2H, t), 2.87 (4H, t), 2.36 (4H, t), 2.13 (3H, s), 1.79 (2H, m), 0.99 (3H, t).

Preparation example 2

5-Hydroxy-2-n-propoxybenzonitrile

[0049]

[0050] 5-acetyl-2-n-propoxybenzonitrile(20.3g, 0.10mol) was dissolved in glacial acetic acid (100ml), followed by ad-dition of ammonium persulfate(60g, 0.26mol). After sulphuric acid solution(H2SO4 10ml/H2O 14ml) was slowly addeddropwise under ice-water bath, the reaction temperature was raised to 45 °C for 3 h. The reaction mixture was pouredinto ice water to generate precipitates, stirred for 0.5 h, filtered, and dried to give the title compound(13.0g, yield: 73%).1H NMR (CDCl3) δ: 8.00 (1H, d), 7.04 (1H, dd), 6.90 (1H, d), 4.05 (2H, t), 1.78 (2H, m), 1.01 (3H, t).

Preparation example 3

3-Cyano-4-n-propoxybenzoic acid

[0051]

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[0052] NaOH (5.52g, 0.138mol) was dissolved in water (35ml) under ice-bath, followed by slow addition of liquidbromine (3.5ml, 0.068mol) under cooling. After a solution of 5-acetyl-2-n-propoxybenzonitrile(7g, 0.034mol) in diox-ane(35ml) was slowly added dropwise thereto, the reaction continued for 2h. The reaction mixture was adjusted slowlyto a pH of about 2 with a diluted hydrochloric acid to generate a large amount of light yellow solid. After filtered, theresultant solid was washed with ethyl acetate, and filtered to obtain the title compound (6.5g, yield: 92%). 1H NMR(CDCl3) δ: 13.21 (1H, br), 8.18 (1H, d), 8.15 (1H, dd), 7.34 (1H, d), 4.18 (2H, t), 1.79 (2H, m), 1.00 (3H, t).

Preparation example 4

4-n-Propoxy-m-benzene dinitrile

[0053]

[0054] The compound(3g, 14.6mmol) of Preparation example 3 was suspended in dichloromethane(30ml), followedby addition of thionyl chloride(2.12ml, 29.2mmol). After refluxed for 2 hours, the reaction mixture was concentrated todryness to obtain an oil. The oil was dissolved in dried benzene(10ml), and concentrated off the solvent.After thedissolution-concentration was repeated three times,the oil was dissolved in dried dichloromethane(10ml), and then slowlyadded dropwise into a solution of ammonia in methanol(15ml) cooled under ice bath, followed by reacting for 0.5 h. Thereaction mixture was concentrated to dryness, and then dissolved in dichloromethane(20ml). The organic layer waswashed with water(30ml32) and saturated brine(40ml), respectively. The resulting organic phase was dried with anhy-drous Na2SO4 and concentrated under reduced pressure. The obtained solid was recrystallized from petroleumether/ethyl acetate, and refluxed in phosphorus oxychloride(10ml) for 1 h. The cooled reaction mixture was poured intoice water to generate precipitate, stirred for 0.5 h, filtered, washed with clear water, and dried to obtain the title com-pound(2.3g, total yield of two steps: 83%). 1H NMR (CDCl3) δ: 7.85 (1H, d), 7.80 (1H, dd), 7.05 (1H, d), 4.12 (2H, t),1.91 (2H, m), 1.09 (3H, t).

Preparation example 5

3-Cyano-4-n-propoxybenzoylhydrazine

[0055]

[0056] The compound(3g, 14.6mmol) of Preparation example 3 was suspended in dichloromethane(30ml), followedby addition of thionyl chloride(2.12ml, 29.2mmol). The reaction mixture was refluxed for 2 hours, and then concentratedto dryness to obtain an oil. The oil was dissolved in dried benzene(10ml), and concentrated off the solvent. After thedissolution-concentration was repeated three times. The obtained oil was dissolved in dried dichloromethane(10ml),and then slowly added dropwise into a mixed solution of hydrazine hydrate(85%) (15ml) and methanol(15ml) cooledunder ice bath, followed by reacting for 0.5 h. The reaction mixture was concentrated to dryness, and then dissolved indichloromethane(20ml). The resulting organic layer was washed with water(30ml32) and saturated brine(40ml), respec-tively. The resulting organic phase was dried with anhydrous Na2SO4 and concentrated under reduced pressure. Theobtained solid was recrystallized from petroleum ether/ethyl acetate to obtain the title compound(2.3g, yield: 72%). 1HNMR (CDCl3) δ: 7.98 (1H, d), 7.94 (1H, dd), 7.59 (1 H, br), 7.00 (1 H, d), 4.09 (2H, t), 1.90 (2H, m), 1.09 (3H, t).

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Preparation example 6

5-(1,3,4--Qxadiazol-2-ly)-2-n-propoxybenzonitrile

[0057]

[0058] The compound(1.5g, 6.8mmol) of preparation example 5 was added in triethyl orthoformate (10ml), and refluxedfor 2 h. The reaction mixture was concentrated to dryness, and the resultant solid was recrystallized from ethyl ace-tate/petroleum ether to obtain the title compound(1.2 g, yield: 76%). 1H NMR (CDCl3) δ: 8.47 (1H, d), 8.27 (1H, dd), 8.25(1H, s), 7.11 (1H, d), 4.13 (2H, t), 1.91 (2H, m), 1.10 (3H, t).

Preparation example 7

2-n-Propoxy-5-(4-methylpiperazin-1-yl)sulfonylbenzamidine

[0059]

[0060] Under ice-bath, the compound(10g, 31mmol) of Preparation example 1 was added into a THF solution(150ml)containning 20% LiN(Si(CH3)3)2, and t stirred for 18h at room temperature. After 4N HCl was added to adjust to a pHof 2-3, THF and most of water were distilled off and the remainning water phase was washed with EtOAc, adjusted toa pH of 12-13 with 4N NaOH, and extracted with CH2Cl2. the organic phase was washd with saturated saline andconcentrated to dryness to give the title compound as a reddish brown oil, which was directly used in the subsequentstep without purification.

Preparation example 8

5-(1,3,4--Oxadiazol-2-yl)-2-n-propoxybenzamidine

[0061] The title compound was prepared from the compound(0.5g, 2.2mmol) of preparation example 6 as a startingmaterial in the same manner as that of preparation example 7, to give the title compound as a reddish brown oil, whichwas directly used in the subsequent step without purification.

Preparation example 9

N1’,N3’-dihydroxy-4-n-propoxy-isophthalamidine

[0062]

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[0063] The compound(3.0g, 16.0mmol) of preparation example 4 was dissolved in a mixed solution of methanol(50ml)and water(50ml), and potassium carbonate(8.9g, 65.2mmol) and hydroxylamine hydrochloride (4.5g, 65.2mmol) wereadded respectively. The reaction mixture was refluxed overnight, and then concentrated off methanol, and cooled downslowly to separate a white solid. After filtered, the solid was washed with water(30ml33), and dried to give the titlecompound (2.0g, yield: 49%). 1H NMR (CDCl3) δ: 9.45 (2H, br), 7.75 (1H, d), 7.63 (1H, dd), 7.05 (1H, d), 5.73 (2H, s),5.60 (2H, s), 4.01 (2H, t), 1.75 (2H, m), 0.99 (3H, t).

Preparation example 10

4-n-Propoxy-1,3-diamidinobenzene

[0064]

[0065] The compound(2.0g, 7.8mmol) of preparation example 9 was dissolved in glacial acetic acid(100ml), addedwith 10%Pd/C(100mg), an d hydrogenized at 65 °C under a pressure of 3MPa for 8h. The reaction mixture was con-centrated to dryness to give 1g of the title compound as a reddish brown solid, which was directly used in the subsequentstep without purification.

Preparation example 11

5-Hydroxy-2-n-propoxybenzamidine

[0066]

[0067] The title compound was prepared from the compound(2.0g, 7.8mmol) of preparation example 2 in the samemanner as that of preparation examples 9 and 10, and directly used in the subsequent step without purification.

Preparation example 12

3-Guanyl-4-n-propoxybenzoic acid

[0068]

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[0069] The title compound was prepared from the compound(6.1g, 29.8mmol) of preparation example 3 in the samemanner as that of preparation examples 9 and 10, and directly used in the subsequent step without purification.

Preparation example 13

2-Ethoxybenzamidine

[0070]

[0071] The title compound was prepared from 2-ethoxybenzonitrile(20.5g, 127.3mmol) in the same manner as that ofpreparation examples 9 and 10, and directly used in the subsequent step without purification.

Preparation example 14

2-n-Propoxybenzamidine

[0072]

[0073] The title compound was prepared from 2-n-propoxybenzonitrile(20.5g, 127.3mmol) in the same manner as thatof preparation examples 9 and 10, and directly used in the subsequent step without purification.

Preparation example 15

2-n-Butoxybenzamidine

[0074]

[0075] The title compound was prepared from 2-butoxybenzonitrile(2.0g, 11.4mmol) in the same manner as that ofpreparation examples 9 and 10, and directly used in the subsequent step without purification.

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Preparation example 16

2-n-Hexoxybenzamidine

[0076]

[0077] The title compound was prepared from 2-n-hexoxybenzonitrile(2.0g, 9.8mmol) in the same manner as that ofpreparation examples 9 and 10, and directly used in the subsequent step without purification.

Preparation example 17

5-Bromo-2-n-propoxybenzamidine

[0078]

[0079] The title compound was prepared from 5-bromo-2-n-propoxybenzonitrile(5.0g, 22.1mmol) in the same manneras that of preparation examples 9 and 10, and directly used in the subsequent step without purification.

Preparation example 18

2-(2-n-Butoxypropoxyphenyl)-6-isopropylpyrimid-4(3H)-one

[0080]

[0081] The compound(10.0g, 42mmol) of preparation example 14 and K2CO3(11.6g, 84mmol) were mixed and sus-pended in DMF(80ml), and ethyl isobutyrylacetate(7.3g, 46mmol) was added thereto in one portion. The reaction mixturewas stirred for 4h at 100°C under nitrogen protection, and then cooled down and poured into ice water. The generatedsolid was washed with water (1.5L), and dried at 60°C to give a light yellow solid crude, which was recrystallized fromethyl acetate to give the white title compound (8.4g, yield: 73%). 1H NMR (CDCl3) δ: 11.23 (1H, br), 8.51 (1H, dd), 7.48(1H, t), 7.19 (1H, t), 7.03 (1H, d), 6.20 (1H, s), 4.18 (2H, t), 2.82 (1H, m), 1.99 (2H, m), 1.27 (6H, d), 1.13 (3H, t).

Preparation example 19

2-(2-n-Propoxyphenyl)-5-bromo-6-isopropylpyrimid-4(3H)-one

[0082]

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[0083] The compound(3.2g, 12mmol) of preparation example 18 was dissolved in CH2Cl2(150ml), and added withpyridine(1ml), followed by dropwise addition of liquid bromine(1.9g, 12mmol) under ice-bath. After reacting for 10 min,the reaction mixture was washed with 1M Na2S2O3(50ml), 1M HCl(40ml) and saturated saline(50ml) respectively. Theorganic phase was dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. Theresidue was recrystallized from acetonitrile-ethylether to give the title compound (3.9g, yield: 95%). 1H NMR (CDCl3) δ:11.41 (1H, br), 8.53 (1H, d), 7.51 (1H, t), 7.13 (1H, t), 7.04 (1H, d), 4.20 (2H, t), 3.51 (1H, m), 2.00 (2H, m), 1.28 (6H,d), 1.14 (3H, t).

Preparation example 20

2-(2-Ethoxyphenyl)-6-isopropylpyrimid-4(3H)-one

[0084]

[0085] The title compound was prepared with the compound(4.0g, 20mmol, calculated on the base of acetate) ofpreparation example 13 and ethyl isobutyrylacetate(3.3g, 21mmol) as the raw materiala in the same manner as that ofpreparation example 18. Yield: 85%. 1H NMR (CDCl3) δ: 11.22 (1H, br), 8.52 (1H, dd), 7.48 (1H, t), 7.12 (1H, t), 7.03(1H, d), 6.20 (1H, s), 4.29 (2H, t), 2.82 (1H, m), 1.59 (3H, t), 1.27 (6H, d).

Preparation example 21

2-(2-Ethoxyphenyl)-5-bromo-6-isopropylpyrimid-4(3H)-one

[0086]

[0087] The title compound was prepared with the compound of preparation example 20 as a raw material in the samemanner as that of preparation example 19. Yield: 95%. 1H NMR (CDCl3) δ: 8.53 (1H, d), 7.51 (1H, t), 7.13 (1H, t), 7.04(1H, d), 4.32 (2H, q), 3.51 (1H, m), 1.59 (3H, t), 1.27 (6H, d).

Preparation example 22

2-(2-Ethoxyphenyl)-5-chloro-6-isopropylpyrimid-4(3H)-one

[0088]

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[0089] The compound(0.52g, 2mmol) of preparation example 20 was dissolved in CH2Cl2(50ml), and added withpyridine(0.5ml), followed by feeding slowly chlorine gas(1.9g, 12mmol) for 3 minutes under ice-bath. The reaction mixturewas washed with 1M Na2S2O3(20ml), 1M HCl(20ml) and saturated saline(40ml) respectively. The organic phase wasdried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The residue was recrystallizedfrom acetonitrile-ethylether to give the title compound (0.57, yield: 98%).1H NMR (CDCl3) δ: 8.52 (1H, d), 7.50 (1H, t),7.13 (1H, t), 7.04 (1H, d), 4.31 (2H, q), 3.49 (1H, m), 1.59 (3H, t), 1.27 (6H, d).

Preparation example 23

2-(2-Ethoxyphenyl)-5-acetamido-6-isopropylpyrimid-4(3H)-one

[0090]

[0091] The title compound was prepared with the compound(1.2g, 5.0mmol) of preparation example 13 and ethyl 2-acetamidoisobutyrylacetate(1.1g, 5.1mmol) as raw materials in the same manner as that of preparation example 18.Yield: 65%. 1H NMR (CDCl3) δ: 8.52 (1H, d), 7.50 (1H, t), 7.13 (1H, t), 7.04 (1H, d), 4.21 (2H, q), 3.00 (1H, m), 2.01 (3H,s), 1.10 (6H, d), 0.96 (3H, t).

Preparation example 24

2-(2-n-Butoxyphenyl)-5-bromo-6-isopropylpyrimid-4(3H)-one

[0092]

[0093] 2-(2-n-butoxyphenyl)-6-isopropylpyrimid-4(3H)-one was prepared with the compound(1.3g, 5.0mmol) of prep-aration example 15 and ethyl isobutyrylacetate(0.8g, 5.1mmol) as raw materials in the same manner as that of preparationexample 18, and then bromized in the same manner as that of preparation example 19 to give the title compound(totalyield of two steps: 69%). 1H NMR (DMSO-d6) δ: 7.89 (1H, d), 7.85 (1H, dd), 7.39 (1H, d), 4.14 (2H, t), 3.37 (1H, m), 1.71(2H, m), 1.35 (2H, m), 1.23 (3H, t), 1.15 (6H, d), 0.81 (3H, t).

Preparation example 25

2-(2-Ethoxyphenyl)-5-bromo-6-n-octylpyrimid-4(3H)-one

[0094]

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[0095] 2-(2-ethoxyphenyl)-6-n-octylpyrimid-4(3H)-one was prepared with hydrochlorate(1.0g, 5.0mmol) of the com-pound obtained in preparation example 13 and ethyl nonanoylacetate(1.2g, 5.1mmol) as raw materials in the samemanner as that of preparation example 18, and then bromized in the same manner as that of preparation example 19to give the title compound(total yield of two steps: 78%).1H NMR (CDCl3) δ: 11.40 (1H, br), 8.47 (1H, d), 7.50 (1H, t),7.12 (1H, t), 7.03 (1H, d), 4.31 (2H, q), 2.84 (2H, t), 1.76 (2H, m), 1.58 (3H, t), 1.51-1.19 (12H, m), 0.88 (3H, t).

Preparation example 26

2-(2-Ethoxyphenyl)-5-bromo-6-phenylpyrimid-4(3H)-one

[0096]

[0097] 2-(2-ethoxyphenyl)-6-phenylpyrimid-4(3H)-one was prepared with hydrochlorate(1.0g, 5.0mmol) of 2-ethoxy-benzamidine(the compound of preparation example 13) and ethyl benzoylacetate(1.0g, 5.1mmol) as raw materials inthe same manner as that of preparation example 18, and then bromized in the same manner as that of preparationexample 19 to give the title compound(total yield of two steps: 80%). 1H NMR (CDCl3) δ: 8.52 (1H, d), 7.84 (2H, m),7.49 (4H, m), 7.08 (2H, m), 4.35 (2H, q), 1.62 (3H, t).

Preparation example 27

2-(2-n-Propoxyphenyl)-5-methyl-6-isopropylpyrimid-4(3H)-one

[0098]

[0099] The title compound was prepared with the compound(1.2g, 5.0mmol) of preparation example 14 and ethyl 2-methylisobutyrylacetate(0.9g, 5.1mmol) as raw materials in the same manner as that of preparation example 18 (yield:69%). 1H NMR (CDCl3) δ: 8.52 (1H, d), 7.45 (1H, t), 7.11 (1H, t), 7.02 (1H, d), 4.17 (2H, t), 3.17 (1H, m), 2.12 (3H, s),1.99 (2H, m), 1.25 (6H, d), 1.14 (3H, t).

Preparation example 28

2-(2-n-Propoxyphenyl)-5-fluoro-6-ethylpyrimid-4(3H)-one

[0100]

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[0101] The title compound was prepared with the compound(1.2g, 5.0mmol) of preparation example 14 and ethyl 2-fluoropropionylacetate(0.8g, 5.1mmol) as raw materials in the same manner as that of preparation example 18 (yield:62%). 1H NMR (CDCl3) δ: 11.16 (1H, br), 8.45 (1H, d), 7.48 (1H, t), 7.12 (1H, t), 7.04 (1H, d), 4.19 (2H, t), 2.73 (2H, q),2.00 (2H, m), 1.30 (3H, t), 1.13 (3H, t).

Preparation example 29

2-(2-n-Propoxyphenyl)-5-methyl-6-ethylpyrimid-4(3H)-one

[0102]

[0103] The title compound was prepared with the compound(1.2g, 5.0mmol) of preparation example 14 and ethyl 2-methylpropionylacetate(0.8g, 5.1mmol) as raw materials in the same manner as that of preparation example 18 (yield:65%). 1H NMR (CDCl3) δ: 11.16 (1H, br), 8.46 (1H, d), 7.46 (1H, t), 7.11 (1H, t), 7.02 (1H, d), 4.16 (2H, t), 2.68 (2H, q),2.11 (3H, s), 1.98 (2H, m), 1.27 (3H, t), 1.13 (3H, t).

Preparation example 30

2-(2-Ethoxyphenyl)-5-hydroxy-6-isopropylpyrimid-4(3H)-one

[0104]

[0105] The compound(1.6g, 5mmol) of preparation example 23 was suspended in concentrated hydrochloric ac-id(15ml), and refluxed for 1h. The reaction mixture was concentrated under reduced pressure to a small volume, andadjusted to a pH of 8~9 with concentrated ammonia to generate precipitate. The precipitate was distilled water (30ml32),and dried to give 1.3g of a deacetyl compound, 2-(2-ethoxyphenyl)-5-amino-6-isopropylpyrimid-4(3H)-one. The aboveresulted compound was dissolved in ethanol(15ml) and cooled under ice-bath, followed by addition of 38% HBF4(5ml).Isoamyl nitrite (0.6g, 6mmol) was slowly added dropwise there, and incubated for 2h. Ethylether was added thereintoto generate precipitate. The filtered precipitate was added in batch into a refluxing 1N H2SO4, reacted for half an hour,and extracted with ethyl acetate(20ml32). The organic phase was washed with water(30ml32), 10%NaHCO3(20ml)and saturated saline(40ml) respectively, dried with anhydrous Na2SO4, and concentrated under reduced pressure. andthe residue was separated by column chromatography to give 150mg of the title compound(yield: 11%). 1H NMR (CDCl3)δ: 11.36 (1H, br), 8.46 (1H, d), 7.52 (1H, t), 7.14 (1H, t), 7.06 (1H, d), 6.42 (1H, s), 4.32 (2H, q), 3.75 (1H, s), 1.61 (3H,t), 1.54 (6H, s).

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Preparation example 31

2-(2-n-Hexoxylphenyl)-6-isopropylpyrimid-4(3H)-one

[0106]

[0107] The title compound was prepared with the compound(1.4g, 5.0mmol) of preparation example 16 and ethylisobutyrylacetate(0.8g, 5.1mmol) as raw materials in the same manner as that of preparation example 18 (yield: 54%).1H NMR (CDCl3) δ: 11.20 (1H, br), 8.52 (1H, d), 7.48 (1H, t), 7.12 (1H, t), 7.04 (1H, d), 6.29 (1H, s), 4.20 (2H, t), 2.81(1H, m), 1.98 (2H, m), 1.58-1.30 (6H, m), 1.27 (6H, d), 0.90 (3H, t).

Preparation example 32

2-(2-Ethoxyphenyl)-6-isopropylpyrimid-4(3H)-one

[0108]

[0109] The title compound was prepared with hydrochlorate(1.0g, 5.0mmol) of 2-ethoxybenzamidine(the compoundof preparation example 13) and ethyl isovalerylacetate(0.9g, 5.1mmol) as raw materials in the same manner as that ofpreparation example 18 (yield: 82%). 1H NMR (CDCl3) δ: 11.24 (1H, br), 8.48 (1H, d), 7.49 (1H, t), 7.12 (1H, t), 7.03(1H, d), 6.16 (1H, s), 4.29 (2H, q), 2.45 (2H, d), 2.18 (1H, m), 1.59 (3H, t), 0.96 (6H, d).

Preparation example 33

2-(2-n-Propoxyphenyl)-5,6-diethylpyrimid-4(3 H)-one

[0110]

[0111] The title compound was prepared with the compound(4.0g, 20mmol) of preparation example 14and methyl 2-ethyl-3-oxopentanoate (3.6g, 21mmol) as raw materials in the same manner as that of preparation example 18 (yield:78%). 1H NMR (CDCl3) δ: 11.18 (1H, br), 8.46 (1H, dd), 7.44 (1H, t), 7.09 (1H, t), 7.01 (1H, d), 4.15 (2H, t), 2.66 (2H,q), 2.58 (2H, q), 1.98 (2H, m), 1.29 (3H, t), 1.14 (3H, t).

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Preparation example 34

2-(5-Bromo-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one

[0112]

[0113] The title compound was prepared with the compound(5.9g, 20mmol) of preparation example 17 and methyl 2-ethyl-3-oxopentanoate (3.6g, 21mmol) as raw materials in the same manner as that of preparation example 18 (yield:63%). 1H NMR (CDCl3) δ: 7.96 (1H, d), 7.89 (1H, dd), 7.44 (1H, d), 4.13 (2H, t), 2.58 (2H, q), 2.46 (2H, q), 1.76 (2H, m),1.18 (3H, t), 1.05 (3H, t), 0.96 (3H, t).

Preparation example 35

2-(5-Bromo-2-n-propoxyphenyl)-6-isopropylpyrimid-4(3H)-one

[0114]

[0115] The title compound was prepared with the compound(4.0g, 20mmol) of preparation example 17 and ethylisobutyrylacetate(3.3g, 21mmol) as raw materials in the same manner as that of preparation example 18 (yield: 93%).1H NMR (CDCl3) δ: 11.12 (1H, br), 8.60 (1H, d), 7.54 (1H, dd), 6.93 (1H, d), 6.22 (1H, s), 4.15 (2H, t), 2.82 (1H, m), 1.98(2H, m), 1.27 (6H, d), 1.12 (3H, t).

Preparation example 36

2-(2-(3-Methoxyn-propoxy)phenyl)-5,6-diethylpyrimid-4(3H)-one

[0116]

[0117] The title compound was prepared with hydrochlorate(1.22g, 5.0mmol) of 2-(3-methoxy-n-propoxy)benzamidineand ethyl 2-ethylpropionylacetate(0.8g, 5.1mmol) as raw materials in the same manner as that of preparation example18 (yield: 73%). 1H NMR (CDCl3) δ: 11.08 (1H, br), 8.46 (1H, dd), 7.44 (1H, t), 7.09 (1H, t), 7.01 (1H, d), 4.25 (2H, t),3.65 (2H, t), 3.42 (3H, s), 2.66 (2H, q), 2.59 (2H, q), 2.22 (2H, m), 1.27 (3H, t), 1.15 (3H, t).

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Example 1

6-Isopropyl-2-[2-n-propoxy-5-(4-methyl-piperazin-1-yl-sulfonyl)phenyl]pyrimid-4(3H)-one

[0118]

[0119] Ethyl isobutyrylacetate(0.5g, 3.2mmol) and the compound(1.2g, 3.2mmol) of preparation example 7 were addedinto DMF(10ml), followed by addition of K2CO3 (0.9g, 6.4mmol). The reaction mixture was heatedto 90 °C for 3h. Thecooled reaction mixture was poured into ice water, and extracted with CH2Cl2(3320ml). The organic phase was washedwith saturated brine, dried with anhydrous Na2SO4, and concentrated. The residue was passed through a neutral aluminacolumn to give 0.7g of the title compound(yield: 50%). 1H NMR (DMSO-d6) δ: 7.89 (1H, d), 7.84 (1H, dd), 7.38 (1H, d),6.15 (1H, s), 4.12 (2H, t), 2.90 (4H, t), 2.75 (1H, m), 2.36 (4H, t), 2.14 (3H, s), 1.74 (2H, m), 1.35 (3H, t), 1.18 (6H, d).

Examples 2~8

[0120] The compounds of Examples 2~8 were prepared by reacting the compound of preparation example 7 with ethylcyanoacetate, diethyl malonate, diethyl acetamidomalonate, ethyl benzoylacetate, ethyl propionylacetate, ethyl aceta-midopropionylacetate, ethyl acetamidocyanoacetate respectively in the same manner as that of preparation example 1.

Example structural formula Nomenclature and data of 1H-NMR(δ )

2 (Reference)

6-amino-2-[2-n-propoxy-5-(4-methyl-1-piperazinylsulf onyl)phenyl]pyrimid-4(3 H)-one (DMSO-d6) δ : 7.90 (1H, d), 7.81 (1H, dd), 7.38 (1H, d), 6.56 (2H, br), 5.00 (1H, s), 4.12 (2H, t), 2.87 (4H, t), 2.36 (4H, t), 2.14 (3H, s), 1.75 (2H, m), 0.97 (3H, t)

3

6-hydroxy-2-[2-n-propoxy-5-(4-methyl-1-piperazinylsu lfonyl)phenyl]pyrimid-4(3H)-one (DMSO-d6) δ: 8.09 (1H, d), 7.76 (1H, dd), 7.36 (1H, d), 6.56 (1H, s), 4.52 (1H, br), 4.15 (2H, t), 2.87 (4H, t), 2.36 (4H, t), 2.13 (3H, s), 1.79 (2H, m), 1.01 (3H, t)

4

5-acetamido-6-hydroxy-2-[2-n-propoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one (DMSO-d6) δ : 7.94 (1H, d), 7.84 (1H, dd), 7.40 (1H, d), 6.56 (1H, s), 4.52 (1H, br), 4.14 (2H, t), 2.88 (4H, t), 2.36 (4H, t), 2.14 (3H, s), 1.99 (3H, s), 1.76 (2H, m), 0.97 (3H, t)

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Example 9

6-Acetamido-2-[2-n-propoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one

[0121]

[0122] The compound(0.20g, 0.5mmol) of Example 2 was suspended in acetic anhydride(5ml), and stirred at 100 °C

(continued)

Example structural formula Nomenclature and data of 1H-NMR(δ )

5

6-phenyl-2-[2-n-propoxy-5-(4-methyl-1-piperazinylsulf onyl)phenyl]pyrimid-4(3H)-one (DMSO-d6) δ : 8.09 (2H, m), 8.01 (1H, d), 7.87 (1H, dd), 7.50 (3H, m), 7.43 (1H, d), 6.91 (1H, s), 4.15 (2H, t), 2.92 (4H, t), 2.37 (4H, t), 2.14 (3H, s), 1.76 (2H, m), 0.95 (3H, t)

6

6-ethyl-2-[2-n-propoxy-5-(4-methyl-1-piperazinylsulfo nyl)phenyl]pyrimid-4(3H)-one (DMSO-d6) δ: 7.89 (1H, d), 7.84 (1H, dd), 7.39 (1H, d), 4.15 (2H, t), 2.89 (4H, t), 2.45 (2H, q), 2.36 (4H, t), 2.16 (3H, s), 1.75 (2H, m), 1.13 (3H, t), 0.96 (3H, t)

7

5-acetamido-6-ethyl-2-[2-n-propoxy-5-(4-methyl-1-pip erazinylsulfonyl)phenyl]pyrimid-4(3H)-one (DMSO-d6) δ : 12.48 (1H, br), 9.22 (1H, br), 7.88 (1H, d), 7.84 (1H, dd), 7.39 (1H, d), 4.13 (2H, t), 2.91 (4H, t), 2.43 (2H, q), 2.40 (4H, t), 2.16 (3H, s), 2.02 (3H, s), 1.76 (2H, m), 1.13 (3H, t), 0.96 (3H, t)

8 (Reference)

5-acetamido-6-amino-2-[2-n-propoxy-5-(4-methyl-1-pi perazinylsulfonyl)phenyl]pyrimid-4(3H)-one (DMSO-d6) δ : 11.57 (2H, s), 8.69 (1H, br), 7.90 (1H, d), 7.83 (1H, dd), 7.39 (1H, d), 6.35 (2H, s), 4.13 (2H, t), 2.87 (4H, t), 2.36 (4H, t), 2.14 (3H, s), 1.96 (3H, s), 1.77 (2H, m), 0.97 (3H, t)

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for 1h. The cooled reaction mixture was poured into ice water to generate a white solid. Afterfiltered, the solid waswashed with clear water(3310ml), and dried at 60°C to give 0.12g of the title compound(yield: 53%). 1H NMR (DMSO-d6) δ: 12.16 (1H, br), 10.54 (1H, br), 7.92 (1H, d), 7.84 (1H, dd), 7.40 (1H, d), 6.89 (1H, s), 4.12 (2H, t), 2.88 (4H, t), 2.36(4H, t), 2.14 (3H, s), 2.08 (3H, s), 1.74 (2H, m), 0.95 (3H, t).

Example 10

5-Bromo-6-isopropyl-2-[2-n-propoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4( 3H)-one

[0123]

[0124] The compound(0.35g, 1.0mmol) of preparation example 19 was slowly added into chlorosulfonic acid(5ml)under ice-bath, and then the ice-bath was removed. After stirred at room temperature for 2h, the reaction mixture wascharily added dropwise into brash ice to generate a faint yellow precipitate. After filtered, the solid was washed with icewater, dissolved in CH2Cl2(50ml), and added dropwise into CH2Cl2(30ml) containing N-methylpiperazine(0.11g,1.1mmol) and triethylamine(1ml) under ice-bath, followed by stirring for 30min. The organic phase was washed withwater(3320ml) and saturated saline(20ml), and evaporated off solvent to dryness. The residue was recrystalized fromethyl acetate/petroleum ether to give the title compound(0.41g, total yield of two steps: 80%). 1H NMR (DMSO-d6) δ:7.91 (1H, d), 7.85 (1H, dd), 7.39 (1H, d), 4.13 (2H, t), 2.90 (4H, t), 2.75 (1H, m), 2.36 (4H, t), 2.14 (3H, s), 1.74 (2H, m),1.35 (3H, t), 1.18 (6H, d).

Examples 11~21

[0125] The compounds of preparation examples 20~30 were reacted sequentially with chlorosulfonic acid and N-methylpiperazine in the same manner as that of preparation example 10 to prepare the compounds of Examples 11~21.

Example structural formula Nomenclature and data of 1H-NMR(δ )

11

6-isopropyl-2-[2-ethoxy-5-(4-methyl-1-piperazinylsulfon yl)phenyl]pyrimid-4(3H)-one (DMSO-d6) δ : 7.89 (1H, d), 7.84 (1H, dd), 7.38 (1H, d), 6.15 (1H, s), 4.22 (2H, q), 2.90 (4H, t), 2.75 (1H, m), 2.36 (4H, t), 2.14 (3H, s), 1.35 (3H, t), 1.18 (6H, d)

12

5-bromo-6-isopropyl-2-[2-ethoxy-5-(4-methyl-1-piperazi nylsulfonyl)phenyl]pyrimid-4(3H)-one (DMSO-d6) δ : 7.91 (1H, d), 7.85 (1H, dd), 7.39 (1H, d), 4.21 (2H, q), 3.36 (1H, m), 2.90 (4H, t), 2.37 (4H, t), 2.14 (3H, s), 1.35 (3H, t), 1.17 (6H, d)

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(continued)

Example structural formula Nomenclature and data of 1H-NMR(δ )

13

5-chloro-6-isopropyl-2-[2-ethoxy-5-(4-methyl-1-piperazi nylsulfonyl)phenyl]pyrimid-4(3H)-one 1H NMR (DMSO-d6) δ : 7.91 (1H, d), 7.84 (1H, dd), 7.39 (1H, d), 4.21 (2H, q), 3.36 (1H, m), 2.90 (4H, t), 2.37 (4H, t), 2.14 (3H, s), 1.34 (3H, t), 1.17 (6H, d).

14

5-acetamido-6-isopropyl-2-[2-ethoxy-5-(4-methyl-1-pipe razinylsulfonyl)phenyl]pyrimid-4(3H)-one (DMSO-d6) δ : 7.89 (1H, d), 7.84 (1H, dd), 7.40 (1H, d), 4.20 (2H, q), 3.00 (1H, m), 2.91 (4H, t), 2.34 (4H, t), 2.14 (3H, s), 2.01 (3H, s), 1.10 (6H, d), 0.96 (3H, t)

15

5-bromo-6-isopropyl-2-[2-n-butoxyl-5-(4-methyl-1-piper azinylsulfonyl)phenyl]pyrimid-4(3H)-one (DMSO-d6) δ: 7.89 (1H, d), 7.85 (1H, dd), 7.39 (1H, d), 4.14 (2H, t), 3.37 (1H, m), 2.90 (4H, t), 2.37 (4H, t), 2.14 (3H, s), 1.71 (2H, m), 1.35 (2H, m), 1.23 (3H, t), 1.15 (6H, d), 0.81 (3H, t)

16

5-bromo-6-n-octyl-2-[2-ethoxy-5-(4-methyl-1-piperaziny lsulfonyl)phenyl]pyrimid-4(3H)-one (DMSO-d6) δ : 7.89 (1H, d), 7.85 (1H, dd), 7.39 (1H, d), 4.14 (2H, q), 2.90 (4H, t), 2.37 (4H, t), 2.14 (3H, s), 1.71 (2H, m), 1.58 (3H, t), 1.51-1.19 (12H, m), 0.88 (3H, t)

17

5-bromo-6-phenyl-2-[2-ethoxy-5-(4-methyl-1-piperazinyl sulfonyl)phenyl]pyrimid-4(3H)-one (DMSO-d6) δ : 7.93 (1H, d), 7.86 (1H, dd), 7.72 (2H, m), 7.50 (3H, m), 7.40 (1H, d), 4.24 (2H, q), 2.90 (4H, t), 2.38 (4H, t), 2.15 (3H, s), 1.38 (3H, t)

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Reference Example 22

5-Amino-6-isopropyl-2-[2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H) -one

[0126]

(continued)

Example structural formula Nomenclature and data of 1H-NMR(δ )

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5-methyl-6-isopropyl-2-[2-n-propoxy-5-(4-methyl-1-pipe razinylsulfonyl)phenyl]pyrimid-4(3H)-one (DMSO-d6) δ : 7.91 (1H, d), 7.84 (1H, dd), 7.40 (1H, d), 4.13 (2H, t), 3.13 (1H, m), 2.94 (4H, t), 2.27 (4H, t), 2.68 (2H, q), 2.11 (3H, s), 1.91 (3H, s), 1.75 (2H, m), 1.14 (6H, d), 0.96 (3H, t)

19

5-fluoro-6-ethyl-2-[2-n-propoxy-5-(4-methyl-1-piperazin ylsulfonyl)phenyl]pyrimid-4(3H)-one (CDCl3) δ: 8.80 (1H, d), 7.86 (1H, dd), 7.16 (1H, d), 4.26 (2H, t), 3.09 (4H, t), 2.74 (4H, m), 2.51 (4H, t), 2.28 (3H, s), 2.03 (2H, m), 1.28 (3H, t), 1.15 (3H, t)

20

5-methyl-6-ethyl-2-[2-n-propoxy-5-(4-methyl-1-piperazi nylsulfonyl)phenyl]pyrimid-4(3H)-one (CDCl3) δ : 10.93 (1H, br), 8.85 (1H, d), 7.84 (1H, dd), 7.13 (1H, d), 4.24 (2H, t), 3.09 (4H, t), 2.68 (2H, q), 2.51 (4H, t), 2.28 (3H, s), 2.12 (3H, s), 2.03 (2H, m), 1.26 (3H, t), 1.16 (3H, t)

21

5-hydroxy-6-isopropyl-2-[2-ethoxy-5-(4-methyl-1-pipera zinylsulfonyl)phenyl]pyrimid-4(3H)-one (CDCl3) δ: 11.36 (1H, br), 8.46 (1H, d), 7.52 (1H, t), 7.14 (1H, t), 7.06 (1H, d), 6.42 (1H, s), 4.32 (2H, q), 3.75 (1H, s), 3.09 (4H, t), 2.51 (4H, t), 2.28 (3H, s), 1.61 (3H, t), 1.54 (6H, s)

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[0127] The compound(60mg, 0.13mmol) of Example 14 was suspended in concentrated hydrochloric acid(3ml), andrefluxed for 1h. The reaction mixture was concentrated under reduced pressure to a small volume, and adjusted to apH of 8~9 with concentrated ammonia to generate precipitate. The obtained precipitate was washed with distilled wa-ter(3ml) and dried to give the title compound(50mg, yield: 91%). 1H NMR (DMSO-d6) δ: 7.90 (1H, d), 7.75 (1H, dd), 7.33(1H, d), 4.91 (2H, s), 4.21 (2H, q), 3.09 (1H, m), 2.89 (4H, t), 2.36 (4H, t), 2.13 (3H, s), 1.37 (3H, t), 1.13 (6H, d).

Example 23

[0128]

[0129] 2-(2-n-hexoxylphenyl)-5-bromo-6-isopropylpyrimid-4(3H)-one was prepared from the compound of Preparationexample 31 as a raw material in the same manner as the bromization of preparation example 19, and then chlorosulfonatedand reacted with N-methylpiperazine in the same manner as that of example 10 to give the title compound(total yield oftwo steps: 85%). 1H NMR (DMSO-d6) δ: 7.90 (1H, d), 7.85 (1H, dd), 7.39 (1H, d), 4.14 (2H, t), 3.37 (1H, m), 2.90 (4H,t), 2.37 (4H, t), 2.14 (3H, s), 1.70 (2H, m), 1.18-1.40 (8H, m), 1.15 (6H, d), 0.81 (3H, t).

Example 24

5-Bromo-6-isobutyl-2-[2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one

[0130]

[0131] The title compound was prepared from the compound of preparation example 32 as a raw material in the samemanner as that of example 23 (total yield: 88%). 1H NMR (DMSO-d6) δ: 7.87 (1H, d), 7.83 (1H, dd), 7.38 (1H, d), 4.21(2H, q), 2.91 (4H, t), 2.65 (2H, d), 2.44 (4H, t), 2.20 (3H, s), 2.17 (1H, m), 1.33 (3H, t), 0.95 (6H, d).

Examples 25~28

[0132] In the same manner as that of example 10, the compound of preparation example 19 was first chlorosulfonatedand then reacted with N-methylethanolamine, 2-(morpholin-1-yl)ethylamine, 3-(morpholin-1-yl)propylamine and N,N-diethylethylendiamine respectively to give the compounds of examples 25~28.

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Examples 29~32

[0133] In the same manner as that of example 10, the compound of preparation example 33 was first chlorosulfona-tedand then reacted with N-methylpiperazine, N-methylethanolamine, 2-morpholinylethylamine and L-proline respec-tively to give the compounds of examples 29~32.

Example structural formula Nomenclature and data of 1H-NMR(δ)

25

5-bromo-6-isopropyl-2-{2-n-propoxy-5-[N-methyl-N-(2-hydroxyethyl)aminosulfonyl]phenyl}pyrimid-4(3H)-one (DMSO-d6) δ: 7.96 (1H, d), 7.89 (1H, dd), 7.37 (1H, d), 4.80 (1H, t), 4.11 (2H, t), 3.52 (2H, q), 3.36 (1H, m), 3.01 (2H, t), 2.73 (3H, s), 1.74 (2H, m), 1.17 (6H, d), 0.94 (3H, t)

26

5-bromo-6-isopropyl-2-{2-n-propoxy-5-[N-(2-morpholinylethyl)aminosulfonyl]phenyl}pyrimid-4(3H)-one (DMSO-d6) δ : 8.02 (1H, d), 7.92 (1H, dd), 7.60 (1H, t), 7.36 (1H, d), 4.10 (2H, t), 3.48 (4H, t), 3.38 (1H, m), 2.88 (2H, t), 2.30 (2H, t), 2.25 (4H, t), 1.74 (2H, m), 1.18 (6H, d), 0.95 (3H, t)

27

5-bromo-6-isopropyl-2-{2-n-propoxy-5-[N-(3-morpholinylpropyl)aminosulfonyl]phenyl}pyrimid-4(3H) -one (DMSO-d6) δ : 8.00 (1H, d), 7.90 (1H, dd), 7.64 (1H, t), 7.36 (1H, d), 4.10 (2H, t), 3.36 (5H, m), 2.79 (2H, t), 2.21 (6H, m), 1.75 (2H, m), 1.52 (2H, m), 1.18 (6H, d), 0.95 (3H, t)

28

5-bromo-6-isopropyl-2-{2-n-propoxy-5-[N-(N’,N’-diethy lamino)ethylaminosulfonyl]phenyl}pyrimid-4(3H)-one (CD3OD) δ: 8.34 (1H, d), 7.99 (1H, dd), 7.34 (1H, d), 4.19 (2H, t), 3.55 (1H, m), 2.99 (2H, t), 2.55-2.66 (6H, m), 1.88 (2H, m), 1.26 (6H, d), 1.00-1.10 (9H, m)

Example structural formula Nomenclature and data of 1H-NMR(δ )

29

5,6-diethyl-2-[2-n-propoxy-5-(4-methyl-1-piperazinylsulf onyl)phenyl]pyrimid-4(3H)-one (CDCl3) δ : 7.96 (1H, d), 7.89 (1H, dd), 7.44 (1H, d), 4.13 (2H, t), 3.09 (4H, t), 2.74 (4H, m), 2.58 (2H, q), 2.46 (2H, q), 2.28 (3H, s), 1.76 (2H, m), 1.18 (3H, t), 1.05 (3H, t), 0.96 (3H, t)

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Example 33

2-(5-Nitro-2-n-propoxyphenyl)-5-bromo-6-isopropylpyrimid-4(3H)-one

[0134]

[0135] The compound(14.0g, 40mmol) of preparation example19 was dissolved in concentrated sulfuric acid(100ml)under ice-bath, and slowly added with a 65-68% concetrated nitric acid(100ml). After stirred at room temperature for 3h,the reaction mixture was slowly added dropwise into ice water to generate a lightyellow precipitate. After filtered, thesolid was washed with clear water(33200ml) and dried at 60°C to give the title compound (14.2g, yield: 90%). 1H NMR(CDCl3) δ: 11.20 (1H, br), 9.36 (1H, d), 8.39 (1H, dd), 7.04 (1H, d), 4.32 (2H, t), 3.56 (1H, m), 2.04 (2H, m), 1.30 (6H,d), 1.16 (3H, t).

Example 34

2-(5-Amino-2-n-propoxyphenyl)-5-bromo-6-isopropylpyrimid-4(3H)-one

[0136]

(continued)

Example structural formula Nomenclature and data of 1H-NMR(δ )

30

5,6-diethyl-2-{2-n-propoxy-5-[N-methyl-N-(hydroxyethy l)aminosulfonyl]phenyl}pyrimid-4(3H)-one (CDCl3) δ : 8.86 (1H, d), 7.90 (1H, dd), 7.14 (1H, d), 4.24 (2H, t), 3.80 (2H, t), 3.23 (2H, t), 2.89 (3H, s), 2.69 (2H, q), 2.59 (2H, q), 2.01 (2H, m), 1.28 (3H, t), 1.15 (3H, t), 1.14 (3H, t)

31

5,6-diethyl-2-{2-n-propoxy-5-[N-(2-morpholinylethyl)am inosulfonyl)phenyl}pyrimid-4(3H)-one (CDCl3) δ : 8.95 (1H, d), 7.97 (1H, dd), 7.13 (1H, d), 4.24 (2H, t), 3.65 (4H, t), 3.06 (2H, t), 2.67 (2H, q), 2.59 (2H, q), 2.49 (2H, t), 2.36 (4H, t), 2.03 (2H, m), 1.28 (3H, t), 1.16(3H,t), 1.14 (3H, t)

32

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propxyphenylsulfonylproline (CDCl3) δ: 8.67 (1H, d), 7.99 (1H, dd), 7.07 (1 H, d), 4.08 (3H, m), 3.48 (1H, m), 3.12 (1H, m), 2.40-2.86 (6H, m), 1.86 (4H, m), 1.20 (3H, t), 1.10 (3H, t), 1.04 (3H, t)

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[0137] The compound(4.0g, 10mmol) of Example 33 was suspended in concentrated hydrochloric acid and heated tobe refluxed. Reduced iron powder(1.7g, 30mmol) was added into the reaction mixture in batch, and stirred for 1h. Thehot reaction mixture was filtered and cooled to room temperature to generate a yellowish precipitate. After filtered, thesolid was dried at 60°C to give the hydrochlorate of the title compound(3.0g, yield: 82%). 1H NMR (DMSO-d6) δ: 12.55(1H, br), 10.18 (2H, br), 7.72 (1H, d), 7.50 (1H, dd), 7.27 (1H, d), 4.04 (2H, t), 3.39 (1H, m), 1.73 (2H, m), 1.17 (6H, d),0.95 (3H, t).

Example 35

1-(3-(4-Isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylt hiourea

[0138]

[0139] The compound(4.0g, 10mmol) of example 34 was suspended in ethanol(10ml), and added with ethyl isothio-cyanate(0.9g, 1.1mmol) and triethylamine(1mL). After refluxed for 3h, the reaction mixture was concentrated to dryness.The resultant solid was washed with distilled water and recrystallized from ethyl acetate-petroleum ether to give the titlecompound(3.4g, yield: 74%). 1H NMR (DMSO-d6) δ: 12.38 (1H, br), 9.41 (1H, br), 7.74 (1H, d), 7.54 (1H, dd), 7.15 (1H,d), 4.04 (2H, t), 3.46 (2H, m), 3.37 (1H, m), 1.75 (2H, m), 1.18 (6H, d), 1.11 (3H, t), 0.97 (3H, t).

Example 36

1-[3-(4-Isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethyl-2-methylisothiourea

[0140]

[0141] The compound(2.7g, 6mmol) of example 35 was suspended in methanol(20ml), and added with iodometh-ane(1.0g, 7mmol). After refluxed for 3h, the reaction mixture was concentrated to dryness. The resultant solid wasrecrystallized from ethylether to obtain the title compound(2.4g, yield: 85%). 1H NMR (DMSO-d6) δ: 7.16 (1H, d), 6.99(1H, dd), 6.87 (1H, d), 4.00 (2H, t), 3.37 (1H, m), 2.94 (2H, q), 2.56 (3H, s), 1.74 (2H, m), 1.18 (6H, d), 1.11 (3H, t), 0.98(3H, t).

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Example 37

N-[3-(4-Isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’,N"-t riethylguanidine

[0142]

[0143] The compound(150mg, 0.28mmol) of example36 was added into 20ml of ethanol, added with diethyl-amine(84mg, 0.8mmol), and stirred at 70 °C for 15h. The cooled reaction mixture was concentrated under reducedpressure. The resultant pasty solid was washed with 4ml of ethyl acetate and dissolved with CH2Cl2(100ml), and thenwashed with water(30ml32), 10% NaOH(20ml) and saturated saline (40ml) respectively. The organic phase was driedwith anhydrous Na2SO4 and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-methanol to obtain a white solid(75mg, yield: 56%). 1H NMR (DMSO-d6) δ: 7.14 (1H, d), 6.98 (1H, dd), 6.85 (1H, d),3.94 (2H, t), 3.37 (1H, m), 3.21 (4H, q), 2.93 (2H, q), 1.69 (2H, m), 1.14 (6H, d), 1.05 (6H, t), 1.00 (3H, t), 0.94 (3H, t).

Examples 38∼40

[0144] The compounds of examples 38∼40 were prepared by reacting the compound of example 36 with piperidine,pyrrolidine and diethanolamine respectively in the same manner as that of example 37.

Example structural formula Nomenclature and data of 1H-NMR(δ )

38

N-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-piperidyl-1-formamid ine (DMSO-d6) δ : 7.39 (1H, d), 7.01 (1H, dd), 6.87 (1H, d), 4.00 (2H, t), 3.37 (1H, m), 3.06 (4H, br), 2.97 (2H, q), 1.76 (2H, m), 1.47 (6H, br), 1.18 (6H, d), 1.03 (3H, t), 1.01 (3H, t)

39

N-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-pyrrolyl-1-formamidi ne (CDCl3) δ : 7.98 (1H, d), 7.20 (1H, dd), 6.97 (1H, d), 4.45 (2H, t), 4.14 (2H, t), 3.44 (4H, m), 3.31 (2H, q), 1.93 (6H, m), 1.27 (6H, d), 1.18 (3H, t), 1.12 (3H, t)

40

2-{2-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidi n-2-yl)-4-n-propoxyphenyl]amino-4,5-dihydro-imidazol-1-yl}-ethanol (CDCl3) δ : 8.25 (1H, d), 7.20 (1H, dd), 6.91 (1H, d), 4.45 (2H, t), 4.13 (2H, t), 3.92 (2H, t), 3.70 (2H, t), 3.56 (2H, t), 3.49 (1H, m), 1.95 (2H, m), 1.27 (6H, d), 1.11 (3H, t)

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Example 41

2-(5-Nitro-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one

[0145]

[0146] The title compound was prepared from the compound of preparation example 33 as a raw material in the samemanner as that of example 33. Yield: 89%. 1H NMR (CDCl3) δ: 9.29 (1H, d), 8.35 (1H, dd), 7.14 (1H, d), 4.30 (2H, t),2.73 (2H, q), 2.60 (2H, q), 2.02 (2H, m), 1.32 (3H, t), 1.15 (6H, t).

Example 42

2-(5-Amino-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one

[0147]

[0148] The compound(16.5g, 50mmol) of example 41 was dissolved in methanol, added with 0.4g 10%Pd/C, andhydrogenized at the normal temperature and pressure. When hydrogen was not absorbed by the reaction mixture anymore, the reaction was quenched and Pd/C was filtered off. The filtrate was concentrated to a small volume, and fedwith HCl gas to generate a white solid. The obtained solid was filtered and dried to give the hydrochlorate of the titlecompound(16.4g. yield: 97%). 1H NMR 1H NMR (CDCl3) δ: 7.68 (1H, d), 7.43 (1H, dd), 7.24 (1H, d), 4.04 (2H, t), 2.57(2H, q), 2.46 (2H, q), 1.75 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.96 (3H, t).

Example 43

1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylthiourea

[0149]

[0150] The title compound was prepared from the compound of example 42 in the same manner as that of example

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35. Yield: 83%. 1H NMR (DMSO-d6) δ: 11.79 (1H, br), 9.40 (1H, br), 7.73 (1H, d), 7.52 (1H, dd), 7.13 (1H, d), 4.05 (2H,t), 3.46 (2H, q), 2.56 (2H, q), 2.45 (2H, q), 1.76 (2H, m), 1.18 (3H, t), 1.10 (3H, t), 1.04 (3H, t), 0.98 (3H, t).

Example 44

1-[3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-3-ethyl-2-methyl isothiourea

[0151]

[0152] The title compound was prepared from the compound of example 43 in the same manner as that of example36. Yield: 87%. 1H NMR (DMSO-d6) δ: 7.78 (1H, d), 7.56 (1H, dd), 7.13 (1H, d), 4.07 (2H, t), 3.46 (2H, q), 2.67 (3H, s),2.56 (2H, q), 2.45 (2H, q), 1.76 (2H, m), 1.18 (3H, t), 1.11 (3H, t), 1.04 (3H, t), 0.97 (3H, t).

Examples 45∼47

[0153] The compounds of example 45∼47 were prepared by reacting the compound of example 44 with piperidine,diethylamine and diethanolamine respectivley, in the same manner as that of example 37.

Example structural formula Nomenclature and data of 1H-NMR(δ )

45

N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-piperidyl-1-formamidine (DMSO-d6) δ: 7.38 (1H, d), 7.01 (1H, dd), 6.86 (1H, d), 4.01 (2H, t), 3.06 (4H, br), 2.97 (2H, q), 2.56 (2H, q), 2.45 (2H, q), 1.76 (2H, m), 1.47 (6H, br), 1.18 (3H, t), 1.03 (3H, t), 1.01 (3H, t), 0.99 (3H, t)

46

N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’,N"-triethylguanidine (DMSO-d6) δ : 11.84 (1H, br), 9.43 (1H, s), 7.53 (1 H, dd), 7.24 (1H, d), 4.06 (2H, t), 3.37 (4H, q), 3.12 (2H, q), 2.56 (2H, q), 2.46 (2H, q), 1.76 (2H, m), 1.18 (3H, t), 1.13 (6H, t), 1.11 (3H, t), 1.04 (3H, t), 0.98 (3H, t)

47

2-{2-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]amino-4,5-dihydro-imidazol-1-yl}-etha nol (DMSO-d6) δ : 7.41 (1H, d), 7.06 (1H, dd), 6.99 (1H, d), 4.86 (1H, br), 4.31 (2H, t), 4.00 (2H, t), 3.60 (4H, t), 3.40 (2H, t), 2.55 (2H, q), 2.45 (2H, q), 1.73 (2H, m), 1.18 (3H, t), 1.03 (3H, t), 0.97 (3H, t)

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Examples 48 and 49

[0154] The compound(0.40g, 1.0mmol) of Example 44 was added in 20ml of ethanol, added with pyrrolidine(0.28g,4mmol), and stirred at 70 °C for 15h. The cooled reaction mixture was concentrated under reduced pressure, dissovledin CH2Cl2(100ml), washed with water(30ml32), 10%NaOH(20ml) and saturated saline(40ml) respectively. The organicphase was dried with anhydrous Na2SO4, and concentrated under reduced pressure. The residue was passed througha silica gel column using ethyl acetate-methanol as an eluant, to give 150mg of the compound of Example 48 and 85mgof the compound of Example 49.

Example 50

5-Bromo-6-isopropyl-2-(2-n-propoxy-5-mesylamidophenyl)pyrimid-4(3H)-one

[0155]

[0156] The compound(0.37g, 1mmol) of Example34 was dissolved in dichloromethane(20ml), and added with triethyl-amine(1ml), followed by slow addition of mesyl chloride(81mL, 1mmol) under ice water bath. After stirred for 0.5h, thereaction mixture was washed with water (10ml), 1N HCl(5ml), saturated sodium bicarbonate solution(10ml), saturatedsaline resepectively. The organic phase was dried with anhydrous Na2SO4 and concentrated under reduced pressureto obtain an oil, which was passed through a silica gel column using ethyl acetate-petroleum ether as a eluent, to givethe title compound( 160mg, yield: 36%). 1H NMR (DMSO-d6) δ: 7.63 (1H, d), 7.37 (1H, dd), 7.18 (1H, d), 6.15 (1H, s),4.02 (2H, t), 3.38 (1H, m), 2.95 (3H, s), 1.74 (2H, m), 1.18 (6H, d), 0.95 (3H, t).

Example structural formula Nomenclature and data of 1H-NMR(δ )

48

N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-pyrrolyl-1-formamidine (DMSO-d6) δ : 7.30 (1H, d), 7.02 (1H, dd), 6.89 (1H, d), 4.01 (2H, t), 3.22 (4H, m), 2.99 (2H, q), 2.55 (2H, q), 2.45 (2H, q), 1.76 (6H, m), 1.18 (3H, t), 1.03 (3H, t), 1.00 (6H, t)

49

N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-pyrrolyl-1-formamide (DMSO-d6) δ : 11.77 (1H, br), 8.17 (1H, br), 7.87 (1H, d), 7.65 (1H, dd), 7.06 (1H, d), 4.01 (2H, t), 3.31 (4H, m), 2.56 (2H, q), 2.46 (2H, q), 1.84 (4H, m), 1.74 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.97 (3H, t)

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Example 51

5,6-Diethyl-2-(2-n-propoxy-5-mesylamidophenyl)pyrimid-4(3H)-one

[0157]

[0158] The title compound was prepared by reacting the compound of Example 42 with mesyl chloride in the samemanner as that of Example 50. 1H NMR (CDCl3) δ: 8.28 (1H, d), 7.50 (1H, dd), 7.11 (1H, br), 7.02 (1H, d), 4.15 (2H, t),3.00 (3H, s), 2.66 (2H, q), 2.58 (2H, q), 1.97 (2H, m), 1.28 (3H, t), 1.14 (3H, t), 1.12 (3H, t).

Examples 52∼54

[0159] The compound of example 52 was prepared by reacting the compound of Example 34 with acetyl chloride, andthe compounds of examples 53 and 54 were prepared by reacting the compound of Example 42 with acetyl chlorideand propionyl chloride, in the same manner as that of Example 50.

Example structural formula nomenclature and data of 1H-NMR(δ )

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N-(3-(1,6-dihydro-4-isopropyl-5-bromo-6-oxopyrimidin-2-yl)-4-propoxyphenyl)acetamide (CDCl3) δ : 8.34 (1H, d), 7.99 (1H, dd), 7.44 (1H, br), 7.01 (1H, d), 4.45 (2H, t), 4.17 (2H, t), 3.50 (1H, m), 2.22 (3H, s), 1.97 (2H, m), 1.26 (6H, d), 1.12 (3H, t)

53

N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-pr opoxyphenyl)acetamide (CDCl3) δ : 8.24 (1H, d), 7.99 (1H, dd), 7.47 (1H, br), 6.99 (1H, d), 4.13 (2H, t), 2.65 (2H, q), 2.58 (2H, q), 2.19 (3H, s), 1.96 (2H, m), 1.28 (3H, t), 1.14 (3H, t), 1.12 (3H, t)

54

N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-pr opoxyphenyl)propionamide (CDCl3) δ: 8.22 (1 H, d), 8.04 (1 H, dd), 7.45 (1 H, br), 6.98 (1H, d), 4.13 (2H, t), 2.65 (2H, q), 2.58 (2H, q), 2.41 (2H, q), 1.96 (2H, m), 1.28 (3H, t), 1.26 (3H, t), 1.14 (3H, t), 1.12 (3H, t)

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Example 55

N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)cyclohexamide

[0160]

[0161] Cyclohexylformic acid(100mg, 0.78mmol) was dissolved in dichloromethane(20ml), added with EDCI (130mg,0.78mmol), and stirred for 0.5h. 1-hydroxy-benzo-triazole(HOBT)(100mg, 0.78mmol) was added thereinto and stirredfor 12h, followed by addition of the compound(235mg, 0.78mmol) of example 42. After stirred at room temperature for2h, the reaction mixture was washed with water(10ml) and saturated saline. The organic phase was dried with anhydrousNa2SO4 and concentrated under reduced pressure to give an oil, which was then passed through a silica gel column togive the title compound(250mg, yield: 78%). 1H NMR (CDCl3) δ: 8.21 (1H, d), 8.08 (1H, dd), 7.55 (1H, br), 6.98 (1H, d),4.13 (2H, t), 2.66 (2H, q), 2.58 (2H, q), 2.50-1.60 (13H, m), 1.28 (3H, t), 1.14 (3H, t), 1.12 (3H, t).

Examples 56 and 57

[0162] The compounds of examples 56 and 57 were prepared by condensing the compound of example 42 with formicacid and N-Boc-4-hydroxypraline respectively in the same manner as that of Example 55.

Example 58

4-n-Propoxy-3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)benzoic acid

[0163]

Example structural formula nomenclature and data of 1H-NMR(δ )

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N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-pr opoxyphenyl)formamide (CDCl3) δ : 8.24 (1H, d), 7.98 (1H, dd), 7.51 (1H, br), 6.97 (1H, d), 4.13 (2H, t), 2.66 (2H, q), 2.58 (2H, q), 2.00 (2H, m), 1.29 (3H, t), 1.16 (3H, t), 1.13 (3H, t).

57

N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-pr opoxyphenyl)-1-t-butyloxycarbonyl-4-hydroxy-prolylamide (CDCl3) δ: 8.26 (1H, d), 8.00 (1H, dd), 7.50 (1H, br), 6.99 (1H, d), 4.14 (2H, t), 2.67 (2H, q), 2.59 (2H, q), 2.19 (3H, br), 1.97 (2H, m), 1.29 (3H, t), 1.15 (3H, t), 1.13 (3H, t)

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[0164] The compound(1.0g, 2.74mmol) of preparation example 34 was dissolved in DMF(12ml), added with CuCN(0.28g, 3.1mmol) and pyridine (1.2ml), and refluxed for 24h. The reaction mixture was cooled down to the room tem-perature, added with a saturated Na2S2O3 aqueous solution(20ml), and extracted with ethyl acetate(15ml33). Theorganic phase was concentrated to dryness. The resultant solid was dissloved in a mixed solution of 2N NaOH aqueoussolution(10ml) and methanol (10ml) amd refluxed for 4h. After the reaction finished, most of methanol and water wereevaporated off. The residue was extracted with CH2Cl2(15ml33), and the water layer was adjusted to a pH of 6∼7 withconcentrated hydrochloric acid. The resultant white solid was filtered and dried to obtain the title compound(0.25g, yield:28%).

Example 59

(Morpholin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxy)benzophen one

[0165]

[0166] The compound(100mg, 0.3mmol) of example 58 was dissolved in dichloromethane(20ml), added with ED-CI(50mg, 0.3mmol), and stirred for 0.5h. HOBT (41mg, 0.3mmol) was added thereinto and stirred for 12h. Then mor-pholine(27mg, 0.3mmol) was added thereinto, and the stirring continued at room temperature for 2h. The reaction mixturewas washed with water(10ml), saturated sodium bicarbonate solution(10ml) and saturated saline respecitively. Theorganic phase was dried with anhydrous Na2SO4 and concentrated under reduced pressure to obtain an oil, which waspassed through a silica gel column to give the title compound(60mg, yield: 50%). 1H NMR (CDCl3) δ: 8.57 (1H, d), 7.59(1H, dd), 7.08 (1H, d), 4.20 (2H, t), 3.74 (8H, br), 2.67 (2H, q), 2.59 (2H, q), 2.00 (2H, m), 1.29 (3H, t), 1.14 (6H, t).

Examples 60 and 61

[0167] The compounds of examples 60 and 61 were prepared by condensing the compound of example 58 withpiperidine and L-prolylamide respectively, in the same manner as that of example 59.

Example structural formula nomenclature and data of 1H-NMR(δ )

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(piperid-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin -2-yl)-4-n-propoxy)benzophenone (CDCl3) δ : 8.56 (1H, d), 7.56 (1H, dd), 7.05 (1H, d), 4.20 (2H, t), 3.56 (4H, br), 2.67 (2H, q), 2.59 (2H, q), 2.00 (2H, m), 1.69 (6H, br), 1.29 (3H, t), 1.14 (6H, t)

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Example 62

4-n-Propoxy-3-(1,6-dihydro-4-isopropyl-6-oxopyrimidin-2-yl)benzoic acid

[0168]

[0169] The compound(4.0g, 14mmol) of preparation example 12 and K2CO3 (7.7g, 56mmol) were mixed and sus-pended in DMF(30ml), and then added with ethyl isobutyrylacetate(2.7g, 17mmol) in one batch. The reaction mixturewas stirred overnight at 100°C under nitrogen protection, cooled, poured into ice water, and adjusted to a pH of 4∼5 byaddition of glacial acetic acid to give a yellowish solid crude. After filtered, the solid was washed with water (250mL) anddried at 60°C. The crude was recrystallized from ethyl acetate to give the white title compound(3.4g, yield: 77%). 1HNMR (CD3OD) δ: 8.57 (1H, d), 8.19 (1H, dd), 7.26 (1H, d), 6.25 (1H, s), 4.20 (2H, t), 2.86 (1H, m), 1.89 (2H, m), 1.29(6H, d), 1.06 (3H, t).

Example 63

(Morpholin-1-yl)(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxy)b enzophenone

[0170]

[0171] (morpholin-1-yl) (3-(4-isopropyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxy)benzophenone was first pre-pared from the compound of example 62 as a raw material in the same manner as that of example 59, and then brominizedin the same manner as that of preparation example 19 to prepare the title compound(yield: 30%). 1H NMR (CDCl3) δ:8.60 (1H, d), 7.65 (1H, dd), 7.11 (1H, d), 4.24 (2H, t), 3.75 (8H, br), 3.51 (1H, m), 2.01 (2H, m), 1.26 (6H, d), 1.14 (3H, t).

(continued)

Example structural formula nomenclature and data of 1H-NMR(δ )

61

(2-aminoformylpyrrol-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxy)benzophenone (CDCl3) δ : 8.69 (1H, d), 7.70 (1H, dd), 7.06 (1H, d), 6.96 (1H, br), 5.56 (1H, br), 4.79 (1H, t), 4.20 (2H, t), 3.62 (2H, t), 2.66 (2H, q), 2.58 (2H, q), 2.00 (2H, m), 2.19-1.79 (6H, m), 1.27 (3H, t), 1.14 (6H, t)

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Examples 64 and 65

[0172] The compounds of examples 64 and 65 were prepared by condensing the compound of example 62 withpiperidine and N-methylpiperazine respectively and then bromizing in the same manner as that of example 63.

Example 66

2-(5-(N,N- dimethylamino-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one

[0173]

[0174] The compound(100mg, 0.3mmol) of example 42 was suspended in water(10ml), added with paraformaldehyde(20mg, 0.66mmol) and formic acid(0.1ml) orderly, and heated to refluxr and stirred for 2h. The reaction mixture wasconcentrated to dryness, and dissolved in dichloromethane(20ml), and washed orderly with water(10ml), 1N HCl(5ml),saturated sodium bicarbonate solution (10ml), saturated saline. The organic phase was dried with anhydrous Na2SO4and concentrated under reduced pressure to give an oil, which was passed through a silica gel column using ethylacetate-petroleum ether as a eluant, to obtain the title compound(100mg, yield: 91%). 1H NMR (CDCl3) δ: 11.33 (1H,br), 7.92 (1H, d), 7.57 (1H, dd), 6.93 (1H, d), 4.08 (2H, t), 2.95 (6H, s), 2.67 (2H, q), 2.58 (2H, q), 1.94 (2H, m), 1.29 (3H,t), 1.14 (3H, t), 1.11 (3H, t).

Example 67

1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea

[0175]

Example structural formula nomenclature and data of 1H-NMR(δ )

64

(piperid-1-yl)(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxo pyrimidin-2-yl)-4-n-propoxy)benzophenone (CDCl3) δ: 8.60 (1H, d), 7.63 (1H, dd), 7.08 (1H, d), 4.24 (2H, t), 3.67 (4H, br), 3.51 (1H, m), 2.00 (2H, m), 1.68 (6H, br), 1.26 (6H, d), 1.14 (3H, t)

65

(4-methyl-piperazin-1-yl)(3-(4-isopropyl-5-bromo-1,6-di hydro-6-oxopyrimidin-2-yl)-4-n-propoxy)benzophenone (CDCl3) δ : 8.59 (1H, d), 7.62 (1H, dd), 7.06 (1H, d), 4.20 (2H, t), 3.51 (1H, m), 2.89 (4H, t), 2.36 (4H, t), 2.13 (3H, s), 1.98 (2H, m), 1.26 (6H, d), 1.13 (3H, t)

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[0176] The compound(200mg, 0.6mmol) of example 42 was suspended in a mixed solution of water(5 ml) and aceticacid(5ml), added with potassium cyanate(81mg, 1 mmol), and heated to reflux and stirred for 2h. The cooled reactionmixture was poured into water to generate a white solid, which was washed with water (10ml33) and dried to give thetitle compound(210mg, yield: 91%). 1H NMR (DMSO-d6) δ: 11.76 (1H, br), 8.56 (1H, br), 7.76 (1H, d), 7.59 (1H, dd),7.06 (1H, d), 5.78 (1H, br), 4.00 (2H, t), 2.56 (2H, q), 2.46 (2H, q), 1.74 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.97 (3H, t).

Example 68

1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylurea

[0177]

[0178] The title compound was prepared by reacting the compound of example 42 with ethyl isocyanate in the samemanner as that of example 35. Yield: 90%. 1H NMR (DMSO-d6) δ: 11.76 (1H, br), 8.46 (1H, br), 7.77 (1H, d), 7.57 (1H,dd), 7.06 (1H, d), 6.01 (1H, t), 4.00 (2H, t), 3.09 (2H, m), 2.56 (2H, q), 2.45 (2H, q), 1.73 (2H, m), 1.19 (3H, t), 1.03 (6H,t), 0.97 (3H, t).

Example 69

1-(3-(4-Isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-phenyl thiourea

[0179]

[0180] The title compound was prepared by reacting the compound of example 34 with phenyl isosulfocyanate in thesame manner as that of example 35. Yield: 89%. 1H NMR (DMSO-d6) δ: 12.38 (1H, br), 9.79 (1H, br), 7.84 (1H, d), 7.65(1H, dd), 7.53-7.07 (6H, m), 4.06 (2H, t), 3.37 (1H, m), 1.75 (2H, m), 1.17 (6H, d), 0.97 (3H, t).

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Example 70

1-(3-(4,5-Diethyl- 1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-guanidine

[0181]

[0182] The compound(140mg, 0.41mmol) of example 42 was suspended in a mixed solution of water(2.5ml) and aceticacid(2.5ml), added with S-methylisothiourea(64mg, 0.45mmol), and heated to reflux under stirring for 10h. The reactionmixture was concentrated to dryness, dissolved in dichloromethane(20ml), and washed orderly with 1N NaOH(5ml),water(10ml) and saturated saline. The organic phase was dried with anhydrous Na2SO4 and concentrated under reducedpressure to give an oil, which was passed through a silica gel column using ethyl acetate-petroleum ether as an eluantto obtain the title compound(35mg, yield: 25%). 1H NMR (CDCl3) δ: 8.26 (1H, d), 8.00 (1H, dd), 7.50 (1H, br), 6.99 (1H,d), 4.14 (2H, t), 2.67 (2H, q), 2.59 (2H, q), 1.97 (2H, m), 1.29 (3H, t), 1.15 (3H, t), 1.13 (3H, t).

Example 71

5-Bromo-6-isopropyl-2-(5-(2-bromoacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one

[0183]

[0184] The compound(2.5g, 7.1mmol) of preparation example 35 was dissolved in DMF(50ml), added with vinyl n-butyl ether(4.7ml), 1,4-bis(diphenylphosphine)butane(0.47g, 1.1mmol), Pd(OAc)2(0.14g, 0.62mmol) andtriethylamine( 1.2ml), followed by stirring at 100°C for 36h. The reaction mixture was cooled to the room teperature,added with water(40ml), and extracted with CH2Cl2(30ml33). The organic phase was concentrated to dryness, addedwith a mixed solution of 10% hydrochloric acid(30ml) and THF(30ml) followed by stirring at room temperature for 4h.THF was evaporated off and the reaction mixture was cooled down to room temperature, adjusted to a pH of 6∼7 with2N NaOH, and extracted with CH2Cl2(20ml33). The organic phase was washed with saturated saline (20ml33), driedwith anhydrous Na2SO4, and concentrated under reduced pressure to give an oil. The oil was dissolved in 25 ml ofglacial acetic acid, added dropwise with liquid bromine(0.5ml) at room temperature, stirred at 30°C for 3h, and addedwith 30 ml of water, followed by extraction with ethyl acetate(30ml33). The organic layer was washed with saturatedsaline(20ml33), dried with anhydrous Na2SO4, and concentrated under reduced pressure. and the residue was passedthrough a silica gel column using ethyl acetate-petroleum ether as a eluant to give the title compound(0.61g, total yield:18%). 1H NMR (CDCl3) δ: 11.20 (1H, br), 9.21 (1H, d), 8.17 (1H, dd), 7.15 (1H, d), 4.45 (2H, s), 4.30 (2H, t), 3.52 (1H,m), 2.03 (2H, m), 1.30 (6H, d), 1.16 (3H, t).

Example 72

5-Bromo-6-isopropyl-2-(5-(2-morpholinylacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one

[0185]

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[0186] The compound(150mg, 0.32mmol) of example 71 was dissolved in dichloromethane(20ml), added with triethyl-amine(0.5ml) and morpholine (40mg, 0.46mmol), followed by stirring for 12h. The reaction mixture was washed orderlywith water(10ml) and saturated saline. The organic phase was dried with anhydrous Na2SO4, and concentrated underreduced pressure to give an oil, which was passed through a silica gel column to obtain the title compound(60mg, yield:39%). 1H NMR (CDCl3) δ: 11.20 (1H, br), 9.21 (1H, d), 8.17 (1H, dd), 7.15 (1H, d), 4.30 (2H, t), 3.75-3.64 (10H, br), 3.52(1H, m), 2.03 (2H, m), 1.30 (6H, d), 1.16 (3H, t).

Example 73

5-Bromo-6-isopropyl-2-(5-(2-(4-methyl-piperazin-1-yl)acetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one

[0187]

[0188] The title compound was prepared by reacting the compound of example71 with N-methyl piperazine, in thesame manner as that of example 72. 1H NMR (CDCl3) δ: 9.23 (1H, d), 8.19 (1H, dd), 7.10 (1H, d), 4.28 (2H, t), 3.77 (2H,s), 3.53 (1H, m), 2.66 (4H, t), 2.52 (4H, t), 2.31 (3H, s), 2.02 (2H, m), 1.29 (6H, d), 1.15 (3H, t).

Example 74

5,6-Diethyl-2-(5-(2-bromoacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one

[0189]

[0190] The title compound was prepared from the compound of preparation example 34 in the same manner as thatof example71. 1H NMR (CDCl3) δ: 11.20 (1H, br), 8.60 (1H, d), 7.59 (1H, dd), 7.10 (1H, d), 4.45 (2H, s), 4.20 (2H, t),2.65 (2H, q), 2.58 (2H, q), 2.03 (2H, m), 1.28 (3H, t), 1.14(6H,t).

Examples 75 and 76

[0191] The compounds of examples 75 and 76 were prepared by reacting the compound of example 74 with N-methylpiperazine and morpholine respectively in the same manner as that of example 72.

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Example 77

5-Bromo-6-isopropyl-2-(2-n-propoxy-5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2 H-pyran-2-ylamino)phenyl)py-rimid-4(3H)-one

[0192]

[0193] The compound of example 34 (200mg, 0.55mmol) was dissolved in n-butanol(10ml), and added with glucose(200mg, 1mmol) and one drop of glacial acetic acid. The reaction mixture was heated under nitrogen protection to refluxfor 12h. The cooled reaction mixture was concentrated to dryness, and added with dichloromethane. The organic layerwas washed with saturated saline(20ml33), dried with anhydrous Na2SO4, and concentrated under reduced pressure.The residue was passed through a silica gel column to give the title compound(60mg, yield: 21%). 1H NMR (DMSO-d6)δ: 7.47 (1H, d), 7.21 (1H, dd), 7.09 (1H, d), 4.31 (1H, d), 4.01 (3H, t), 3.63 (1H, d), 3.46 (1H, d), 3.09-3.29 (4H, m), 2.57(2H, q), 2.46 (2H, q), 1.72 (2H, m), 1.18 (6H, d), 0.95 (3H, t).

Example 78

5-Bromo-6-isopropyl-2-(2-n-propoxy-5-(tetrahydro-3,4-dihydroxy-5-(1,2-dihydroxyethyl) fur-2-ylamino)phenyl)pyrimid-4(3H)-one

[0194]

Example structural formula nomenclature and data of 1H-NMR(δ)

75

5,6-diethyl-2-(5-(2-(4-methyl-piperazin-1-yl)acetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one (CDCl3) δ : 11.08 (1H, br), 8.58 (1H, d), 7.57 (1H, dd), 7.06 (1H, d), 4.20 (2H, t), 3.77 (2H, s), 2.97 (4H, t), 2.65 (2H, q), 2.58 (2H, q), 2.46 (4H, t), 2.33 (3H, s), 2.00 (2H, m), 1.28 (3H, t), 1.14 (6H, t)

76

5,6-diethyl-2-(5-(2-morpholinylacetyl)-2-n-propoxyphen yl)pyrimid-4(3 H)-one (CDCl3) δ : 11.08 (1H, br), 8.58 (1H, d), 7.57 (1H, dd), 7.06 (1H, d), 4.20 (2H, t), 3.78 (2H, s), 3.67 (4H, t), 3.48 (4H, t), 2.65 (2H, q), 2.58 (2H, q), 2.00 (2H, m), 1.28 (3H, t), 1.14(3H, t), 1.12 (3H, t)

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[0195] The title compound was prepared by reacting the compound of example 34 with mannose in the same manneras that of example 77. 1H NMR (DMSO-d6) δ: 7.47 (1H, d), 7.21 (1H, dd), 7.09 (1H, d), 4.75 (1H, d), 4.01 (2H, t), 3.78-3.37(7H, m), 2.57 (2H, q), 2.46 (2H, q), 1.72 (2H, m), 1.18 (6H, d), 0.95 (3H, t).

Examples 79 and 80

[0196] The compounds of examples 79 and 80 were prepared by reacting the compound of example 42 with mannoseand glucose in the same manner as that of example 77.

Example 81

2-(5-Hydroxy-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one

[0197]

[0198] The title compound was prepared by reacting methyl 2-ethyl-3-oxovalerate with the compound of preparationexample 11 in the same manner as that of example 1. 1H NMR (CDCl3) δ: 7.98 (1H, d), 7.00 (1H, dd), 6.88 (1H, d), 4.06

Example structural formula nomenclature and data of 1H-NMR(δ )

79

5,6-diethyl-2-(2-n-propoxy-5-(tetrahydro-3,4-dihydroxy-5-(1,2-dihydroxyethyl)fur-2-ylamino)phenyl)pyrimid-4(3 H)-one (DMSO-d6) δ : 7.48 (1H, d), 7.20 (1H, dd), 7.10 (1H, d), 4.77 (1H, d), 4.01 (2H, t), 3.78-3.37 (6H, m), 2.57 (2H, q), 2.46 (2H, q), 1.74 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

80

5,6-diethyl-2-(2-n-propoxy-5-(tetrahydro-3,4,5-trihydrox y-6-(hydroxymethyl)-2H-pyran-2-ylamino)phenyl)pyrimi d-4(3H)-one (DMSO-d6) δ : 7.48 (1H, d), 7.20 (1H, dd), 7.10 (1H, d), 4.31 (1H, d), 4.01 (3H, t), 3.63 (1H, d), 3.46 (1H, d), 3.09-3.29 (4H, m), 2.57 (2H, q), 2.46 (2H, q), 1.72 (2H, m), 1.18 (3H, t), 1.03 (3H, t), 0.96 (3H, t)

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(2H, t), 2.65 (2H, q), 2.59 (2H, q), 1.92 (2H, m), 1.26 (3H, t), 1.15 (3H, t), 1.08 (3H, t).

Example 82

(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl) acetate

[0199]

[0200] The compound of example 82 was prepared by reacting the compound of example 81 with acetyl chloride inthe same manner as that of example 50. 1H NMR (CDCl3) δ: 8.20 (1H, d), 7.20 (1H, dd), 7.02 (1H, d), 4.17 (2H, t), 2.67(2H, q), 2.59 (2H, q), 2.33 (3H, s), 1.99 (2H, m), 1.29 (3H, t), 1.15 (6H, t).

Example 83

3 -(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl ethylaminoformate

[0201]

[0202] The title compound was prepared by reacting the compound of example 81 with ethyl isocyanate in the samemanner as that of example 35. 1H NMR (CDCl3) δ: 8.20 (1H, d), 7.25 (1H, dd), 6.99 (1H, d), 5.06 (1H, br), 4.14 (2H, t),3.32 (2H, m), 2.66 (2H, q), 2.58 (2H, q), 1.98 (2H, m), 1.28 (3H, t), 1.22 (3H, t), 1.14 (3H, t), 1.13 (3H, t).

Example 84

5,6-Diethyl-2-(2-n-propoxy-5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yloxy)phenyl)pyrimid-4(3H)-one

[0203]

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[0204] The compound(500mg, 1.6mmol) of example 81 was dissolved in dichloromethane(20ml), and added withborontrifluorideetherate(2ml) and 2,3,4,6-tetra-o-acetyl-α-d-glucopyranose trichloroacetylimide ester(800mg,1.6mmol)(the preparation thereof refers to Upreti, M. et al. Tetrahedron, 2000, 56, 6577.), followed by stirring at roomtemperature for 12h. The reaction mixture was concentrated to dryness to give an oil. The oil was dissolved in a mixedsolution of methanol(10ml) and water(10ml), and added with potassium carbonate(900mg, 6.5mmol), followed by re-fluxing for 2h. The reaction mixture was concentrated to dryness, and the residue was passed through a silica gel columnto obtain the title compound(155mg, total yield of two steps: 20%. 1H NMR (DMSO-d6) δ: 7.48 (1H, d), 7.20 (1H, dd),7.10 (1H, d), 4.75 (1H, d), 4.01 (2H, t), 3.69-3.48 (2H, m), 3.33-3.14 (4H, m), 2.57 (2H, q), 2.46 (2H, q), 1.72 (2H, m),1.18 (3H, t), 1.03 (3H, t), 0.96 (3H, t).

Example 85

3 -(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl mesylate

[0205]

[0206] The title compound was prepared by reacting the compound of example 81 with mesyl chloride in the samemanner as that of example 50. 1H NMR (CDCl3) δ: 8.39 (1H, d), 7.43 (1H, dd), 7.06 (1H, d), 4.18 (2H, t), 3.20 (3H, s),2.68 (2H, q), 2.58 (2H, q), 2.00 (2H, m), 1.28 (3H, t), 1.14 (6H, t).

Example 86

2-(5-(2,5-Dimethyl-1H-pyrrol-1-yl)-2-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one

[0207]

[0208] The compound(200mg, 0.66mmol) of example 42 and 2,5-hexanedione(76mg, 0.66mmol) were dissolved inethanol(10ml) and added with glacial acetic acid(0.1ml), followed by refluxing for 12h. The reaction mixture was con-centrated to dryness, dissolved in CH2Cl2(10ml), and washed with saturated NaHCO3(10ml) and saturated saline(10ml),dried and concentrated. The residue was passed through a silica gel column to give the title compound(110mg, yield:44%). 1H NMR (CDCl3) δ: 11.20 (1H, br), 8.42 (1H, d), 7.30 (1H, dd), 7.10 (1H, d), 5.93 (2H, s), 4.23 (2H, t), 2.63 (2H,q), 2.59 (2H, q), 2.06 (6H, s), 2.04 (2H, m), 1.24 (3H, t), 1.18 (3H, t), 1.15 (3H, t).

Example 87

2,2’-(4-n-Propoxy-1,3-phenylene)bis(5,6-diethylpyrimid-4(3H)-one)

[0209]

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[0210] The title compound was prepared by reacting the compound of example 10 with methyl 2-ethyl-3-oxovaleratein the same manner as that of example 1. 1H NMR (CDCl3) δ: 9.08 (1H, d), 8.34 (1H, dd), 7.08 (1H, d), 4.19 (2H, t),2.74-2.48 (8H, m), 1.97 (2H, m), 1.30 (3H, t), 1.27 (3H, t), 1.15 (3H, t), 1.13 (3H, t), 1.07 (3H, t).

Example 88

2-(5-(1,3,4-Oxadiazol-2-yl)-2-propoxyphenyl)-5,6-diethylpyrimid-4(3 H)-one

[0211]

[0212] The title compound was prepared by reacting the compound of example 8 with methyl 2-ethyl-3-oxovaleratein the same manner as that of example 1. 1H NMR (CDCl3) δ: 8.69 (1H, d), 8.51 (1H, dd), 7.05 (1H, d), 4.14 (2H, t), 2.69(4H, m), 1.92 (2H, m), 1.31 (3H, t), 1.21 (3H, t), 1.12 (3H, t).

Example 89

Ethyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)acetate

[0213]

[0214] The compound(250mg, 0.76mmol) of example 58 was suspended in dichloromethane(20ml), and added withthionyl chloride (2ml), followed by refluxing for 2h to clear the reaction mixture. The reaction mixture was concentratedoff thionyl chloride, and added with dichloromethane. Under ice-bath, the reaction mixture was added dropwise into adichloromethane solution(20ml) containning ethyl 2-aminoacetate(80mg, 0.727mmol) and triethylamine(0.2ml,1.454mmol), followed by stirring for 0.5h. The reaction mixture was then washed with water(20ml) and saturated sa-line(20ml) respectively. The organic layer was dried with anhydrous sodium sulfate, and concentrated. The residue waspassed through a silica gel column to give the white title compound(100mg, yield: 33%). 1H NMR (CDCl3) δ: 11.01 (1H,

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br), 8.87 (1H, d), 8.00 (1H, dd), 7.08 (1H, d), 6.87 (1H, br), 4.27 (2H, q), 4.25 (2H, t), 4.21 (2H, t), 2.69 (2H, q), 2.59 (2H,q), 2.00 (2H, m), 1.32 (3H, t), 1.30 (3H, t), 1.15 (6H, t).

Examples 90∼97

[0215] Tn the same manner as that of example 89, the compound of example 58 was first reacted with thionyl chlorideto obtain a product, which was then reacted with N-aminoethylmorpholine, diethanolamine, 3-aminocyclocaprolactam,1-(2,3-dichlorophenyl)piperazine, 3-isopropylpyrazole, cyclohexylamine, 2-aminomethylpyridine and methyl 3,3-dimeth-ylbutyrate respectively to give the title compounds of examples 90∼97,.

Example structural formula nomenclature and data of 1H-NMR(δ)

90

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-m orpholinylethyl)-4-n-propoxybenzamide (CDCl3) δ : 11.07 (1H, br), 8.82 (1H, d), 8.05 (1H, dd), 7.10 (1H, d), 7.03 (1H, br), 4.22 (2H, t), 3.77 (2H, t), 3.59 (2H, m), 2.68 (2H, q), 2.65 (2H, t), 2.58 (2H, q), 2.56 (4H, t), 2.01 (2H, m), 1.31 (3H, t), 1.15 (6H, t)

91

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N,N-di( 2-hydroxyethyl)-4-n-propoxybenzamide (CDCl3) δ : 8.60 (1H, d), 7.70 (1H, dd), 7.04 (1H, d), 7.03 (1H, br), 4.18 (2H, t), 4.05-3.40 (8H, m), 2.66 (2H, q), 2.58 (2H, q), 1.99 (2H, m), 1.28 (3H, t), 1.14 (3H, t), 1.13 (3H, t)

92

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-ca prolactam-3-yl)-4-n-propoxybenzamide (CDCl3) δ : 11.10 (1H, br), 8.94 (1H, d), 7.98 (1H, dd), 7.73 (1H, br), 7.10 (1H, d), 6.20 (1H, br), 4.74 (1H, t), 4.24 (2H, t), 3.35 (2H, m), 2.72 (2H, q), 2.62 (2H, q), 2.27 (1H, d), 2.14-1.40 (7H, m), 1.34 (3H, t), 1.17 (6H, t)

93

(4-(2,3-dichlorophenyl)piperazin-1-yl)(3-(4,5-diethyl-1,6 -dihydro-6-oxopyrimidin-2-yl)-4-n-propoxy)benzopheno ne (CDCl3) δ: 11.10 (1H, br), 8.65 (1H, d), 7.64 (1H, dd), 7.24 (1H, dd), 7.21 (1H, q), 7.11 (1H, d), 6.97 (1H, dd), 4.24 (2H, t), 3.99 (2H, br), 3.75 (2H, br), 3.11 (4H, br), 2.69 (2H, q), 2.62 (2H, q), 2.04 (2H, m), 1.32 (3H, t), 1.18 (3H, t), 1.17 (3H, t)

94

(3-isopropylpyrazol-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-o xopyrimidin-2-yl)-4-n-propoxy)benzophenone (CDCl3 ) δ: 11.06 (1H, br), 9.52 (1H, d), 8.40 (1H, dd), 8.38 (1H, d), 7.16 (1H, d), 6.42 (1H, d), 4.29 (2H, t), 3.08 (1H, m), 2.68 (2H, q), 2.62 (2H, q), 2.06 (2H, m), 1.35 (3H, t), 1.33 (3H, t), 1.30 (3H, t), 1.19 (3H, t), 1.18 (3H, t)

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Examples 98∼105

[0216] The compound of example 42 was reacted with trifluoroacetyl chloride, ethyl oxalyl monochloride, acrolyl chlo-ride, crotonyl choride, ethyl malonyl chloride, 2-ethoxybenzoyl chloride, nicotinoyl chloride, 5-isopropylthiazoleformylchloride respectively to give the title compounds of examples 98∼105, in the same manner as that of example 50.

(continued)

Example structural formula nomenclature and data of 1H-NMR(δ)

95

N-cyclohexyl-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin -2-yl)-4-n-propoxybenzamide (CDCl3) δ: 10.98 (1H, br), 8.75 (1H, d), 7.95 (1H, dd), 7.05 (1H, d), 6.13 (1H, br), 4.19 (2H, t), 3.99 (1H, m), 2.69 (2H, q), 2.60 (2H, q), 2.05 (2H, m), 2.01 (2H, m), 1.83-1.62 (4H, m), 1.44 (2H, m), 1.31 (5H, m), 1.16 (3H, t), 1.15 (3H, t)

96

N-((pyrid-2-yl)methyl)-3-(4,5-diethyl-1,6-dihydro-6-oxo pyrimidin-2-yl)-4-n-propoxybenzamide (CDCl3) δ : 8.56 (1H, d), 8.21 (1H, d), 7.98 (1H, dd), 7.69 (1H, t), 7.50 (1H, br), 7.35 (1H, d), 7.22 (1H, t), 7.04 (1H, d), 4.77 (2H, d), 4.04 (2H, t), 2.90 (2H, q), 2.85 (2H, q), 1.80 (2H, m), 1.37 (3H, t), 1.27 (3H, t), 1.02 (3H, t)

97

methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)-3,3-dimethylbutyrate (CDCl3) δ: 11.03 (1H, br), 8.90 (1H, d), 7.96 (1H, dd), 7.09 (1H, d), 6.74 (1H, br), 4.69 (1H, d), 4.22 (2H, t), 3.76 (3H, s), 2.70 (2H, q), 2.59 (2H, q), 2.01 (2H, m), 1.32 (3H, t), 1.15 (6H, t), 1.07 (9H, s)

Example structural formula nomenclature and data of 1H-NMR(δ )

98

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2,2,2-trifluoroacetamide (CDCl3) δ: 8.43 (1H, d), 8.23 (1H, br), 7.99 (1H, dd), 7.06 (1H, d), 4.18 (2H, t), 2.67 (2H, q), 2.59 (2H, q), 1.98 (2H, m), 1.29 (3H, t), 1.14 (6H, t)

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(continued)

Example structural formula nomenclature and data of 1H-NMR(δ )

99

ethyl N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformylformate (CDCl3) δ : 8.47 (1 H, d), 8.08 (1H, dd), 7.06 (1H, d), 4.44 (2H, q), 4.18 (2H, t), 2.68 (2H, q), 2.60 (2H, q), 2.00 (2H, m), 1.45 (3H, t), 1.31 (3H, t), 1.15 (6H, t)

100

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)acrylamide (CDCl3) δ: 8.30 (1H, d), 8.11 (1H, dd), 7.79 (1H, br), 6.99 (1H, d), 6.45 (1H, d), 6.29 (1H, dd), 5.77 (1H, d), 4.13 (2H, t), 2.64 (2H, q), 2.58 (2H, q), 1.95 (2H, m), 1.27 (3H, t), 1.14 (3H, t), 1.12 (3H, t)

101

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-crotonamide (CDCl3) δ : 8.22 (1H, d), 8.00 (1H, dd), 7.47 (1H, br), 7.01 (1H, m), 6.99 (1H, d), 5.97 (1H, d), 4.13 (2H, t), 2.65 (2H, q), 2.58 (2H, q), 1.96 (2H, m), 1.92 (3H, t), 1.28 (3H, t), 1.15 (3H, t), 1.13 (3H, t)

102

ethyl N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformylacetate (CDCl3) δ : 9.25 (1H, br), 8.36 (1H, d), 7.95 (1H, dd), 7.00 (1H, d), 4.28 (2H, q), 4.15 (2H, t), 3.49 (2H, s), 2.68 (2H, q), 2.59 (2H, q), 1.98 (2H, m), 1.34 (3H, t), 1.30 (3H, t), 1.15 (3H, t), 1.14 (3H, t)

103

2-ethoxy-N-(3-(4, 5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)benzamide (CDCl3) δ: 11.25 (1H, br), 10.28 (1H, br), 8.35 (1H, dd), 8.32 (1H, d), 8.30 (1H, dd), 7.49 (1H, t), 7.13 (1H, t), 7.05 (1H, d), 7.02 (1H, d), 4.31 (2H, q), 4.18 (2H, t), 2.67 (2H, q), 2.60 (2H, q), 1.99 (2H, m), 1.71 (3H, t), 1.31 (3H, t), 1.15 (6H, t)

104

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)nicotinamide (CDCl3) δ : 9.17 (1H, br), 8.78 (1H, d), 8.40 (2H, d), 8.27 (1H, d), 8.11 (1H, dd), 7.45 (1H, dd), 7.04 (1H, d), 4.15 (2H, t), 3.49 (2H, s), 2.63 (2H, q), 2.58 (2H, q), 1.97 (2H, m), 1.14 (3H, t), 1.13 (3H, t)

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Example 106

t-Butyl 3-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl) aminoformyl)propylaminoformate

[0217]

[0218] N-Boc-4-aminobutyric acid(203mg, 1mmol) was dissolved in dichloromethane(50ml), and added with EDCI(180mg, 1mmol) and HOBT (135mg, 1mmol), followed by stirring at room temperature for 12h. The compound of example42(300mg, 1mmol) was added thereinto and the stirring continued at room temperature for 6h. The reaction mixturewas washed with water(50ml) and saturated saline (50ml) respectively. The organic layer was dried with anhydroussodium sulfate, and concentrated. and the residue was passed through a silica gel column to give the white title compound(200mg. yield: 41 %). 1H NMR (CDCl3) δ: 9.00 (1H, br), 8.39 (1H, d), 8.09 (1H, dd), 6.99 (1H, d), 4.83 (1H, t), 4.14 (2H,t), 3.27 (2H, m), 2.65 (2H, q), 2.59 (2H, q), 2.41 (2H, t), 1.97 (2H, m), 1.89 (2H, m), 1.48 (9H, s), 1.29 (3H, t), 1.14 (3H,t), 1.13 (3H, t).

Example 107

4-Acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)butyr amide

[0219]

[0220] The compound(200mg, 0.412mmol) of example 106 was dissolved in dichloromethane(30ml) and added withtrifluoroacetic acid(2ml), followed by stirring at room temperature for 0.5h. The reaction mixture was directly concentratedto dryness. The resultant oil was dissolved in dichloromethane(30ml) and added with triethylamine(1ml). Under ice-waterboth, acetyl chloride(33mg, 0.42 mmol) was added dropwise thereinto.0.5h later, TLC showed that the reaction wascomplete. The reaction mixture was washed with water(50ml) and saturated saline(50ml). The organic layer was driedwith anhydrous sodium sulfate, and concentrated. and the residue was passed through a silica gel column to give the

(continued)

Example structural formula nomenclature and data of 1H-NMR(δ )

105

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-5-isopropylthiazolyl-2-formamide (DMSO-d6) δ : 11.85 (1H, br), 10.60 (1H, br), 8.24 (1H, d), 7.94 (1H, dd), 7.68 (1H, s), 7.19 (1H, d), 4.05 (2H, t), 3.16 (1H, m), 2.58 (2H, q), 2.47 (2H, q), 1.76 (2H, m), 1.33 (6H, d), 1.21 (3H, t), 1.05 (3H, t), 0.98 (3H, t)

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white title compound(50mg, yield: 28%). 1H NMR (CDCl3) δ: 8.79 (1H, br), 8.51 (1H, d), 7.93 (1H, dd), 6.99 (1H, d), 6.05(1H, br), 4.15 (2H, t), 3.40 (2H, t), 2.68 (2H, q), 2.60 (2H, q), 2.44 (2H, t), 2.03 (3H, s), 1.97 (2H, m), 1.94 (2H, m), 1.32(3H, t), 1.16 (3H, t), 1.14 (3H, t).

Examples 108∼112

[0221] According to the same manner as those of example 106 and example 107, the compound of example 42 wasreacted with N-Boc-proline, N-Boc-valine, N-Boc-phenylalanine, N-Boc-lactamine and N-Boc-lysine respectively, andthen removed the Boc-protecting group and acetylated to obtain the compounds of examples 108∼112.

Example structural formula nomenclature and data of 1H-NMR(δ )

108

1-acetyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2 -yl)-4-n-propoxyphenyl)pyrrolidinyl-2-formamide (CDCl3) δ : 9.61 (1H, br), 8.35 (1H, d), 7.83 (1H, dd), 6.94 (1H, d), 4.78 (1H, d), 4.12 (2H, t), 3.60 (1H, m), 3.46 (1H, m), 2.67 (2H, q), 2.58 (2H, q), 2.16 (3H, s), 2.07 (2H, m), 1.95 (2H, m), 1.85 (2H, m), 1.30 (3H, t), 1.14 (3H, t), 1.12 (3H, t)

109

2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimid in-2-yl)-4-n-propoxyphenyl)-3-methylbutyramide (CDCl3) δ : 11.19 (1H, br), 8.91 (1H, br), 8.36 (1H, d), 7.94 (1H, dd), 6.98 (1H, d), 6.44 (1H, br), 4.53 (1H, d), 4.14 (2H, t), 2.66 (2H, q), 2.59 (2H, q), 2.20 (1H, m), 2.12 (3H, s), 1.98 (2H, m), 1.29 (3H, t), 1.16 (3H, t), 1.14 (3H, t), 1.06 (3H, d), 1.04 (3H, d)

110

2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimid in-2-yl)-4-n-propoxyphenyl)-3-phenylpropionamide (CDCl3) δ: 11.18 (1H, br), 8.14 (1H, d), 7.77 (1H, dd), 7.42-7.36 (5H, m), 6.95 (1H, d), 6.46 (1H, d), 4.88 (1H, q), 4.13 (2H, t), 3.17 (2H, m), 2.66 (2H, q), 2.60 (2H, q), 2.05 (3H, s), 1.97 (2H, m), 1.30 (3H, t), 1.16 (3H, t), 1.13 (3H, t)

111

2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimid in-2-yl)-4-n-propoxyphenyl)propionamide (CDCl3) δ : 8.99 (1H, br), 8.36 (1H, d), 7.88 (1H, dd), 6.94 (1H, d), 6.49 (1H, d), 4.77 (1H, m), 4.11 (2H, t), 2.64 (2H, q), 2.57 (2H, q), 2.08 (3H, s), 1.95 (2H, m), 1.49 (3H, d), 1.27 (3H, t), 1.13 (3H, t), 1.11 (3H, t)

112

2,6-diacetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyri midin-2-yl)-4-n-propoxyphenyl)hexanamide (DMSO-d6) δ: 11.79 (1H, br), 10.07 (1H, br), 8.11 (1H, d), 8.02 (1H, d), 7.79 (1H, t), 7.75 (1H, dd), 7.13 (1H, d), 4.33 (1H, m), 4.02 (2H, t), 3.00 (2H, q), 2.57 (2H, q), 2.46 (2H, q), 1.86 (3H, s), 1.76 (3H, s), 1.74 (2H, m), 1.20 (3H, t), 1.04 (3H, t), 0.97 (3H, t)

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Example113

N1-(3-(4,5-diethyl-l,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)propanediamide

[0222]

[0223] The compound of Example 102(100mg) was sealed in a 25ml tube , added with a saturated solution(15ml) ofammonia in ethanol(15ml), and heated to 120 °C to react for 12h. The reaction mixture was concentrated to dryness,and the residue was recrystallized from ethyl acetate to give the white title compound(60mg, yield: 64%). 1H NMR(CDCl3) δ: 9.57 (1H, br), 8.38 (1H, d), 7.87 (1H, dd), 7.02 (1H, br), 6.96 (1H, d), 5.93 (1H, br), 4.12 (2H, t), 3.44 (2H, s),2.64 (2H, q), 2.57 (2H, q), 1.95 (2H, m), 1.27 (3H, t), 1.14 (3H, t), 1.11 (3H, t).

Examples 114∼115

[0224] The compounds of examples 114∼115 were prepared by respectively reacting the compounds of examples 99and 89 with the saturated solution of ammonia in ethanol in the same manner as that of example 113.

Example 116

5,6-Diethyl-2-{2-n-propoxy-5-[(2-(1-methylpyrrol-2-yl)ethyl)aminosulfonyl]phenyl}pyrimi d-4(3H)-one

[0225]

Example structural formula nomenclature and data of 1H-NMR(δ)

114

N1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)oxalamide (DMSO-d6) δ: 11.81 (1H, br), 10.67 (1H, br), 8.30 (1H, d), 7.96 (1H, br), 7.87 (1H, dd), 7.16 (1H, d), 4.04 (2H, t), 2.56 (2H, q), 2.46 (2H, q), 1.75 (2H, m), 1.20 (3H, t), 1.04 (3H, t), 0.97 (3H, t)

115

N-(aminoformylmethyl)-3-(4,5-diethyl-1,6-dihydro-6-ox opyrimidin-2-yl)-4-n-propoxybenzamide (DMSO-d6) δ: 12.00 (1 H, br), 8.66 (1H, t), 8.17 (1H, d), 8.01 (1H, dd), 7.38 (1H, br), 7.23 (1H, d), 7.02 (1H, br), 4.09 (2H, t), 3.80 (2H, d), 2.58 (2H, q), 2.47 (2H, q), 1.75 (2H, m), 1.20 (3H, t), 1.04 (3H, t), 0.97 (3H, t)

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[0226] According to the same manner as that of example 10, the compound of preparation example 33 was firstchlorosulfonated, and then reacted with 2-(1-methylpyrrol-2- yl)ethylamine to give the compound of example 116. 1HNMR (DMSO-d6) δ: 12.04 (1H, br), 8.02 (1H, d), 7.87 (1H, dd), 7.60 (1H, br), 7.35 (1H, d), 4.11 (2H, t), 2.88 (1H, m),2.75 (2H, m), 2.57 (2H, q), 2.47 (2H, q), 2.12 (3H, s), 2.00 (2H, m), 1.85-1.62 (4H, m), 1.55 (2H, m), 1.29 (2H, m), 1.19(3H, t), 1.04 (3H, t), 0.96 (3H, t).

Example 117

3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-(1-methylpyrrol-2-yl)ethyl)-4-n-pro poxybenzamide

[0227]

[0228] According to the same manner as that of example 89, the compound of example 58 was reacted with 2-(1-methylpyrrol-2-yl)ethylamine to give the compound of example 117. 1H NMR (DMSO-d6) δ: 12.01 (1H, br), 8.50 (1H, t),8.12 (1H, d), 7.96 (1H, dd), 7.22 (1H, d), 4.08 (2H, t), 3.28 (2H, m), 2.98 (1H, m), 2.58 (2H, q), 2.47 (2H, q), 2.25 (3H,s), 2.13 (2H, m), 1.90 (2H, m), 1.75 (2H, m), 1.64 (2H, m), 1.45 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.96 (3H, t).

Examples 118∼136

[0229] According to the same manner as that of example 10, the compound of preparation example 33 was firstchlorosulfonated, and then reacted with citrulline, ornithine, valine, lactamine, serine, ethyl lactamate, homotaurine,taurine, asparamide, tryptophan, glycocine, t-leucine, glutamine, ethyl isoleucinate, methyl 6-acetyllysinate, hydrox-yethylpiperazine, 1-propanolamine, N-hydroxyethyl-2-(morpholin-1-yl)ethylamine, N-methyl-2-(pyrrolidin-1-yl)ethyl-amine respectively, to obtain the compounds of examples 118∼136.

Example structural formula nomenclature and data of 1H-NMR(δ)

118

2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5-ureavaleric acid (DMSO-d6) δ: 8.04 (1H, d), 7.86 (1H, dd), 7.31 (1H, d), 4.10 (2H, t), 3.63 (1H, m), 2.83 (2H, m), 2.56 (2H, q), 2.44 (2H, q), 1.75 (2H, m), 1.50 (2H, m), 1.29 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

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Example structural formula nomenclature and data of 1H-NMR(δ)

119

2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5-aminovaleric acid (DMSO-d6) δ: 8.04 (1H, d), 7.86 (1H, dd), 7.31 (1H, d), 4.10 (2H, t), 3.63 (1H, m), 2.83 (2H, m), 2.56 (2H, q), 2.44 (2H, q), 1.75 (2H, m), 1.50 (2H, m), 1.38 (2H, m), 1.16 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

120

2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-methylbutyric acid (DMSO-d6) δ: 8.08 (1H, d), 7.87 (1H, dd), 7.32 (1H, d), 4.11 (2H, t), 3.50 (1H, d), 2.58 (2H, q), 2.47 (2H, q), 1.95 (1H, m), 1.77 (2H, m), 1.20 (3H, t), 1.05 (3H, t), 0.98 (3H, t), 0.83 (3H, d), 0.80 (3H, d)

121

2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropionic acid (DMSO-d6) δ : 8.06 (1H, d), 7.88 (1H, dd), 7.33 (1H, d), 4.11 (2H, t), 3.75 (1H, q), 2.57 (2H, q), 2.46 (2H, q), 1.76 (2H, m), 1.18 (3H, d), 1.15 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

122

2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-hydroxypropionic acid (DMSO-d6) δ: 8.09 (1H, d), 7.89 (1H, dd), 7.32 (1H, d), 4.10 (2H, t), 3.74 (1H, t), 3.44 (2H, d), 2.58 (2H, q), 2.46 (2H, q), 1.76 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

123

ethyl 2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropionate (CDCl3) δ : 11.01 (1H, br), 8.84 (1H, d), 7.97 (1H, dd), 7.07 (1H, d), 6.86 (1H, d), 4.78 (1H, m), 4.25 (2H, q), 4.20 (2H, t), 2.68 (2H, q), 2.59 (2H, q), 2.00 (2H, m), 1.54 (3H, d), 1.31 (3H, t), 1.30 (3H, t), 1.14 (6H, t)

124

3-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropylsulfonic acid (DMSO-d6) δ: 8.08 (1H, d), 7.96 (1H, dd), 7.42 (1H, d), 4.12 (2H, t), 2.90 (2H, t), 2.68 (2H, q), 2.57 (2H, q), 2.35 (2H, t), 1.73 (2H, m), 1.58 (2H, m), 1.21 (3H, t), 1.07 (3H, t), 0.93 (3H, t)

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Example structural formula nomenclature and data of 1H-NMR(δ)

125

2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminoethylsulfonic acid (DMSO-d6) δ: 8.09 (1H, d), 7.97 (1H, dd), 7.45 (1H, d), 4.13 (2H, t), 2.98 (2H, t), 2.68 (2H, t), 2.65 (2H, q), 2.54 (2H, q), 1.74 (2H, m), 1.20 (3H, t), 1.06 (3H, t), 0.93 (3H, t)

126

2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-aminoformylpropioni c acid (DMSO-d6) δ : 8.05 (1H, d), 7.87 (1H, dd), 7.31 (1H, d), 4.09 (3H, m), 2.57 (2H, q), 2.46 (2H, q), 2.29 (2H, d), 1.75 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

127

2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-indylpropionic acid (DMSO-d6) δ: 8.00 (1H, d), 7.56 (1H, dd), 7.31 (1H, d), 7.24 (1H, d), 7.05 (1H, d), 7.00 (1H, s), 6.96 (1H, d), 6.85 (1H, t), 4.08 (2H, t), 3.91 (1H, dd), 3.05 (1H, dd), 2.83 (1H, dd), 2.57 (2H, q), 2.47 (2H, q), 1.79 (2H, m), 1.18 (3H, t), 1.06 (3H, t), 1.00 (3H, t)

128

2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminoacetic acid (DMSO-d6) δ: 8.04 (1H, d), 7.89 (1H, dd), 7.33 (1H, d), 4.10 (2H, t), 3.56 (2H, s), 2.57 (2H, q), 2.46 (2H, q), 1.76 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

129

2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3,3-dimethylbutyric acid (DMSO-d6) δ : 8.08 (1H, d), 7.85 (1H, dd), 7.31 (1H, d), 4.10 (3H, m), 2.58 (2H, q), 2.46 (2H, q), 1.76 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.97 (3H, t), 0.86 (9H, s)

130

2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-4-aminoformylbutyric acid (DMSO-d6) δ : 8.18 (1H, d), 8.07 (1H, d), 7.85 (1H, dd), 7.31 (1H, d), 4.10 (2H, t), 3.70 (1H, d), 2.57 (2H, q), 2.46 (2H, q), 2.06 (2H, t), 1.93-1.57 (4H, m), 1.19 (3H, t), 1.04 (3H, t), 0.97 (3H, t)

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Example structural formula nomenclature and data of 1H-NMR(δ)

131

ethyl 2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-methylvalerate (CDCl3) δ: 10.99 (1H, br), 8.89 (1H, d), 7.90 (1H, dd), 7.09 (1H, d), 5.31 (1H, d), 4.21 (2H, t), 3.99-3.78 (3H, m), 2.66 (2H, q), 2.57 (2H, q), 2.00 (2H, m), 1.79 (1H, m), 1.42 (1H, m), 1.28 (3H, t), 1.17 (1H, m), 1.13 (6H, t), 1.05 (3H, t), 0.91 (3H, d), 0.86 (3H, t)

132

methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxyphenylsulfonamido)-6-acetamidocaproate (DMSO-d6) δ: 12.03 (1H, br), 8.20 (1H, d), 8.02 (1H, d), 7.86 (1H, dd), 7.58 (1H, t), 7.34 (1H, d), 4.11 (3H, m), 3.60 (3H, s), 2.70 (2H, m), 2.57 (2H, q), 2.46 (2H, q), 1.83 (3H, s), 1.76 (2H, m), 1.56 (2H, m), 1.36 (2H, m), 1.26 (2H, m), 1.18 (3H, t), 1.04 (3H, t), 0.97 (3H, t)

133

5,6-diethyl-2-(2-n-propoxy-5-(4-hydroxyethyl-1-piperazi nylsulfonyl)phenyl]pyrimid-4(3H)-one (CDCl3) δ: 10.97 (1H, br), 8.86 (1H, d), 7.83 (1H, dd), 7.15 (1H, d), 4.25 (2H, t), 3.57 (2H, t), 3.08 (4H, t), 2.72-2.50 (10H, m), 2.36 (1H, br), 2.03 (2H, m), 1.27 (3H, t), 1.16 (3H, t), 1.13 (3H, t)

134

5,6-diethyl-2-(2-n-propoxy-5-(3-hydroxypropylamino sulfonyl)phenyl]pyrimid-4(3H)-one (CDCl3) δ : 10.93 (1H, br), 8.86 (1H, d), 7.97 (1H, dd), 7.12 (1H, d), 5.26 (1H, t), 4.23 (2H, t), 3.72 (2H, t), 3.16 (2H, q), 2.67 (2H, q), 2.59 (2H, q), 2.02 (2H, m), 1.70 (2H, m), 1.28 (3H, t), 1.15 (6H, t)

135

5,6-diethyl-2-(2-n-propoxy-5-(N-(2-morpholinylethyl)-N -(2-hydroxyethyl)aminosulfonyl)phenyl)pyrimid-4(3H)-o ne (DMSO-d6) δ: 12.09 (1 H, br), 8.00 (1H, d), 7.92 (1H, dd), 7.33 (1H, d), 5.00 (1H, br), 4.11 (2H, t), 3.52 (6H, t), 3.25 (2H, t), 3.16 (2H, t), 2.57 (2H, q), 2.47 (2H, q), 2.45 (2H, t), 2.36 (4H, t), 1.75 (2H, m), 1.18 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

136

5,6-diethyl-2-(2-n-propoxy-5-(N-methyl-N-(2-(pyrrolidin -1-yl)ethyl)aminosulfonyl)phenyl)pyrimid-4(3H)-one (CDCl3) δ: 8.90 (1H, d), 7.89 (1H, dd), 7.14 (1H, d), 4.25 (2H, t), 3.23 (2H, t), 2.85 (3H, s), 2.74 (2H, t), 2.67 (2H, q), 2.60 (6H, m), 2.03 (2H, m), 1.79 (4H, m), 1.28 (3H, t), 1.17 (3H, t), 1.15 (3H, t)

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Example137

5,6-Diethyl-2-(2-n-propoxy-5-(2-(N,N-diethyl)aminoethylaminosulfonyl)phenyl]pyrimid-4( 3H)-one maleate

[0230]

[0231] The compound(0.35g, 1.0mmol) of preparation example 33 was slowly added into chlorosulfonic acid(5ml)under ice-bath. The ice-bath was removed, and the reaction mixture was stirred at room temperature for 2h, and thencarefully added dropwise into brash ice to generate a yellowish precipitate, and filtered. The resultant solid was washedwith ice water, dissolved in CH2Cl2(50ml), and added dropwise into a CH2Cl2 solution(30ml) containing N,N-diethyleth-ylendiamine(0.13g, 1.1mmol) and triethylamine(1ml) under ice-bath. After addition, the stirring continued for 30min. Theorganic phase was washed with water(3320ml) and saturated saline(20ml), and distilled off solvent to give an oil. Theoil was dissolved in anhydrous ethanol(5ml), added with maleic acid (0.13g, 1.1mmol), and heated to 50 °C to stir for15min. The reaction mixture was stirred for 2h under ice-bath, filtered and dried to give the title compound(0.45g, totalyield of two steps: 77.6%). 1H NMR(DMSO-d6) δ: 8.05 (1H, d), 7.92 (1H, dd), 7.38 (1H, d), 6.04 (2H, s), 4.12 (2H, t),3.18-3.02 (8H, m), 2.57 (2H, q), 2.46 (2H, q), 1.76 (2H, m), 1.18 (3H, t), 1.16 (3H, t), 1.04 (3H, t), 0.96 (3H, t).

Examples 138~153

[0232] According to the same manner as that of example 89, the compound of example 58 was first reacted withthionyl chloride, and the resultant products were reacted with phenylalanine, methyl prolinate, methyl tyrosinate, ethyltryptophanate, methyl valinate, methyl histidinate, ethyl isoleucinate, lactamine, asparamide, glutamine, serine, arginine,methyl phenylalaninate, methyl lactaminate, methyl leucinate, ethyl lactaminate respectively to obtain the compoundsof examples 138~153.

Example structural formula nomenclature and data of 1H-NMR(δ )

138

2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phenylpropionic acid (DMSO-d6) δ : 8.09 (1H, d), 7.89 (1H, dd), 7.32-7.08 (6H, m), 4.48 (1H, m), 4.05 (2H, t), 3.21 (1H, dd), 3.04 (1H, dd), 2.57 (2H, q), 2.45 (2H, q), 1.73 (2H, m), 1.18 (3H, t), 1.03 (3H, t), 0.95 (3H, t)

139

methyl N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzoylprolinate (CDCl3) δ : 8.76 (1H, d), 7.76 (1H, dd), 7.05 (1H, d), 4.68 (1H, t), 4.20 (2H, t), 3.78 (3H, s), 3.68 (2H, m), 2.67 (2H, q), 2.58 (2H, q), 2.33 (1H, m), 2.01 (5H, m), 1.28 (3H, t), 1.14 (6H, t)

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Example structural formula nomenclature and data of 1H-NMR(δ )

140

methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)-3-(4-hydroxyphenyl)propionate (CDCl3) δ: 11.04 (1H, br), 8.77 (1H, d), 7.89 (1H, dd), 7.06 (1H, d), 7.00 (2H, dd), 6.76 (2H, dd), 5.03 (1H, m), 4.18 (2H, t), 3.78 (3H, s), 3.18 (2H, d), 2.68 (2H, q), 2.59 (2H, q), 1.97 (2H, m), 1.30 (3H, t), 1.14 (3H, t), 1.12 (3H, t)

141

ethyl 2-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-pr opoxybenzamido)-3-(1H-indol-3-yl)propionate (CDCl3) δ: 10.97 (1H, br), 8.82 (1H, d), 8.22 (1H, br), 7.82 (1H, dd), 7.57 (1H, d), 7.35 (1H, d), 7.15 (1H, t), 7.08 (1H, s), 7.05 (1H, t), 7.01 (1H, d), 6.81 (1H, br), 5.10 (1H, m), 4.17 (2H, t), 3.46 (2H, d), 2.68 (2H, q), 2.59 (2H, q), 1.97 (2H, m), 1.28 (3H, t), 1.24 (3H, t), 1.16 (3H, t), 1.12 (3H, t)

142

methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)-3-methylbutyrate (CDCl3) δ: 11.02 (1H, br), 8.91 (1H, d), 7.98 (1H, dd), 7.09 (1H, d), 6.78 (1H, br), 4.76 (1H, dd), 4.22 (2H, t), 3.78 (3H, s), 2.71 (2H, q), 2.60 (2H, q), 2.30 (1H, m), 2.01 (2H, m), 1.32 (3H, t), 1.15 (6H, t), 1.03 (3H, d), 1.02 (3H, d)

143

methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)-3-(1H-imidazol-4-yl)propionate (CDCl3) δ : 8.94 (1H, d), 8.26 (1H, br), 8.03 (1H, dd), 7.62 (1H, s), 7.06 (1H, dd), 6.87 (1H, s), 4.98 (1H, m), 4.19 (2H, t), 3.71 (3H, s), 3.23 (2H, dd), 2.68 (2H, q), 2.58 (2H, q), 1.98 (2H, m), 1.31 (3H, t), 1.14 (3H, t), 1.13 (3 H, t)

144

ethyl 2-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-pr opoxybenzamido)-3-methylvalerate (CDCl3) δ : 11.02 (1H, br), 8.89 (1H, d), 7.97 (1H, dd), 7.08 (1H, d), 6.77 (1H, br), 4.79 (1H, dd), 4.23 (4H, m), 2.70 (2H, q), 2.59 (2H, q), 2.00 (3H, m), 1.56 (2H, m), 1.31 (6H, t), 1.15 (6H, t), 0.99 (3H, d), 0.98 (3H, t)

145

2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)propionic acid (DMSO-d6) δ: 8.67 (1H, d), 8.18 (1H, d), 8.04 (1H, dd), 7.24 (1H, d), 4.41 (1H, m), 4.09 (2H, t), 2.59 (2H, q), 2.47 (2H, q), 1.75 (2H, m), 1.39 (3H, d), 1.19 (3H, t), 1.05 (3H, t), 0.96 (3H, t)

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(continued)

Example structural formula nomenclature and data of 1H-NMR(δ )

146

2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)-3-aminoformylpropionic acid (DMSO-d6) δ : 8.13 (1H, d), 7.97 (1H, dd), 7.05 (1H, d), 4.71 (1H, m), 4.09 (2H, t), 2.66 (2H, m), 2.58 (2H, q), 2.47 (2H, q), 1.75 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

147

2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)-4-aminoformylbutyric acid (DMSO-d6) δ: 8.18 (1H, d), 8.02 (1H, dd), 7.24 (1H, d), 4.34 (1H, m), 4.09 (2H, t), 2.58 (2H, q), 2.47 (2H, q), 2.21 (2H, t), 2.00 (2H, m), 1.75 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

148

2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)-3-hydroxypropionic acid (DMSO-d6) δ : 8.18 (1H, d), 8.03 (1H, dd), 7.24 (1H, d), 4.43 (1H, m), 4.09 (2H, t), 3.77 (2H, d), 2.58 (2H, q), 2.47 (2H, q), 1.75 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

149

2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)-5-guanidylvaleric acid (DMSO-d6) δ : 8.09 (1H, d), 7.92 (1H, dd), 6.97 (1H, d), 4.19 (1H, m), 3.96 (2H, t), 3.04 (2H, m), 2.56 (2H, q), 2.44 (2H, q), 1.82 (2H, m), 1.67 (2H, m), 1.51 (2H, m), 1.17 (3H, t), 1.03 (3H, t), 0.91 (3H, t)

150

methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)-3-phenylpropionate (DMSO-d6) δ: 12.01 (1H, br), 8.84 (1H, d), 8.11 (1H, d), 7.94 (1H, dd), 7.24 (6H, m), 4.64 (1H, m), 4.08 (2H, t), 3.64 (3H, s), 3.16 (1H, dd), 3.08 (1H, dd), 2.58 (2H, q), 2.47 (2H, q), 1.74 (2H, m), 1.20 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

151

methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)propionate (CDCl3) δ: 11.00 (1H, br), 8.87 (1H, d), 7.99 (1H, dd), 7.08 (1H, d), 6.83 (1H, br), 4.80 (1H, m), 4.22 (2H, t), 3.81 (3H, s), 2.70 (2H, q), 2.59 (2H, q), 2.01 (2H, m), 1.55 (3H, d), 1.31 (3H, t), 1.15(6H, t)

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Examples 154~155

[0233] The compounds of examples 154~155 were prepared by reacting the compound of example 151 with N-methylpiperazine and saturated solution of ammonia in ethanol respectively in the same manner as that of example 113.

Examples 156~175

[0234] According to the same manner as that of Example 89, the compound of example 58 was first reacted withthionyl chloride, and the resultant products were reacted with ammonia water, 2-thienylethylamine, furfurylamine, t-butylamine, isobutylamine, allylamine, 1-(2-pyridyl)piperazine, hydroxylethoxyethylpiperazine, hydroxyethylpiperazine,1-propanolamine, 2-propanolamine, N-ethylethanolamine, N,N-diethylethylendiamine, homotaurine, taurine, N-methyl-ethanolamine, N-benzylpiperazine, N-methyl-2-(pyrrolidin-1-yl)ethylamine, methyl 5-aminopiperidine-2-carboxylate andN,O-dimethylhydroxylamine respectively, to obtain the compounds of examples 156~175.

(continued)

Example structural formula nomenclature and data of 1H-NMR(δ )

152

methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)-4-methylvalerate (CDCl3) δ: 8.91 (1H, d), 8.00 (1H, dd), 7.09 (1H, d), 4.85 (1H, m), 4.22 (2H, t), 3.77 (3H, s), 2.73 (2H, q), 2.60 (2H, q), 2.01 (2H, m), 1.77 (3H, m), 1.32 (3H, t), 1.16 (3H, t), 1.15 (3H, t), 1.00 (3H, d), 0.99 (3H, d)

153

ethyl 2-(3-(4,5-diethylmethyl -1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamid o)propionate (DMSO-d6) δ : 12.05 (1H, br), 8.76 (1H, d), 8.17 (1H, d), 8.02 (1H, dd), 7.24 (1H, d), 4.44 (1H, m), 4.09 (4H, m), 2.57 (2H, q), 2.47 (2H, q), 1.75 (2H, m), 1.39 (3H, d), 1.18 (6H, t), 1.04 (3H, t), 0.96 (3H, t)

Example structural formula nomenclature and data of 1H-NMR(δ)

154

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-(4-methylpiperazin-1-yl)-1-oxopropan-2-yl)-4-n-propoxybe nzamide (DMSO-d6) δ : 11.00 (1H, d), 8.87 (1H, d), 7.95 (1H, dd), 7.41 (1H, d), 7.05 (1H, d), 5.08 (1H, m), 4.20 (2H, t), 3.63 (4H, m), 2.68 (2H, q), 2.58 (2H, q), 2.43 (4H, m), 2.31 (3H, s), 1.99 (2H, m), 1.44 (3H, d), 1.30 (3H, t), 1.14 (3H, t)

155

N-(1-aminoformylethyl)-3-(4,5-diethyl-1,6-dihydro-6-ox opyrimidin-2-yl)-4-n-propoxybenzamide (CDCl3) δ : 11.03 (1H, br), 8.74 (1H, d), 7.91 (1H, dd), 7.02 (1H, d), 6.54 (1H, br), 5.81 (1H, br), 4.73 (1H, m), 4.16 (2H, t), 2.66 (2H, q), 2.58 (2H, q), 1.97 (2H, m), 1.54 (3H, d), 1.28 (3H, t), 1.14 (3H, t), 1.12 (3H, t)

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Example structural formula nomenclature and data of 1H-NMR(δ )

156

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-pro poxybenzamide (CDCl3) δ: 8.85 (1H, d), 8.05 (1H, dd), 7.09 (1H, d), 4.21 (2H, t), 2.70 (2H, q), 2.59 (2H, q), 2.00 (2H, m), 1.30 (3H, t), 1.15 (3H, t), 1.14 (3H, t)

157

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-pro poxy-N-(2-(thien-2-yl)ethyl)benzamide (CDCl3) δ: 11.03 (1H, br), 8.76 (1H, d), 7.97 (1H, dd), 7.18 (1H, d), 7.07 (1H, dd), 6.97 (1H, t), 6.90 (1H, d), 4.20 (2H, t), 3.75 (2H, t), 3.17 (2H, t), 2.68 (2H, q), 2.59 (2H, q), 1.99 (2H, m), 1.30 (3H, t), 1.15 (3H, t), 1.14 (3H, t)

158

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-pro poxy-N-((fur-2-yl)methyl)benzamide (CDCl3) δ : 11.00 (1H, br), 8.81 (1H, d), 8.00 (1H, dd), 7.38 (1H, d), 7.07 (1H, d), 6.64 (1H, br), 6.33 (2H, m), 4.66 (2H, d), 4.20 (2H, t), 2.68 (2H, q), 2.58 (2H, q), 1.99 (2H, m), 1.29 (3H, t), 1.15 (3H, t), 1.14 (3H, t)

159

N-t-butyl-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl )-4-n-propoxybenzamide (CDCl3) δ : 11.04 (1H, br), 8.76 (1H, d), 7.94 (1H, dd), 7.06 (1H, d), 4.20 (2H, t), 4.15 (2H, q), 2.75 (2H, t), 2.71 (2H, q), 2.59 (2H, q), 2.00 (2H, m), 1.49 (9H, s), 1.31 (3H, t), 1.16 (3H, t), 1.15 (3H, t)

160

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-isobu tyl-4-n-propoxybenzamide (CDCl3) δ : 11.03 (1H, br), 8.80 (1H, d), 7.98 (1H, dd), 7.07 (1H, d), 6.38 (1H, br), 4.20 (2H, t), 3.31 (2H, t), 2.69 (2H, q), 2.59 (2H, q), 1.97 (3H, m), 1.30 (3H, t), 1.15 (3H, t), 1.14 (3H, t), 1.00 (6H, d)

161

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-allyl-4-n-propoxybenzamide (CDCl3) δ : 11.02 (1H, br), 8.81 (1H, d), 8.00 (1H, dd), 7.08 (1H, d), 6.41 (1H, br), 5.97 (1H, m), 5.24 (2H, dd), 4.21 (2H, t), 4.12 (2H, t), 2.69 (2H, q), 2.59 (2H, q), 2.00 (2H, m), 1.30 (3H, t), 1.15 (6H, t)

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(continued)

Example structural formula nomenclature and data of 1H-NMR(δ )

162

(4-(pyrid-2-yl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzophenone (CDCl3) δ : 11.08 (1H, br), 8.62 (1H, d), 8.20 (1H, dd), 7.61 (1H, dd), 7.53 (1H, t), 7.08 (1H, d), 6.69 (1H, t), 6.67 (1H, d), 4.22 (2H, t), 3.77 (4H, t), 3.63 (4H, t), 2.65 (2H, q), 2.58 (2H, q), 2.01 (2H, m), 1.27 (3H, t), 1.16 (3H, t), 1.14 (3H, t)

163

(4-(hydroxylethoxyethyl)piperazin-1-yl)(3-(4,5-diethyl-1, 6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzopheno ne (CDCl3) δ: 11.08 (1H, br), 8.58 (1H, d), 7.56 (1H, dd), 7.05 (1H, d), 4.20 (2H, t), 3.90-3.50 (10H, m), 2.70-2.55 (10H, m), 2.00 (2H, m), 1.27 (3H, t), 1.14 (3H, t), 1.13 (3H, t)

164

(4-(hydroxylethyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihy dro-6-oxopyrimidin-2-yl)-4-n-propoxybenzophenone (CDCl3) δ : 11.06 (1H, br), 8.59 (1H, d), 7.58 (1H, dd), 7.07 (1H, d), 4.20 (2H, t), 3.80 (4H, t), 3.66 (2H, t), 2.70-2.55 (10H, m), 2.01 (2H, m), 1.28 (3H, t), 1.15 (6H, t)

165

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(3-hy droxylpropyl)-4-n-propoxybenzamide (CDCl3) δ : 10.94 (1H, br), 8.76 (1H, d), 7.97 (1H, dd), 7.01 (1H, d), 4.15 (2H, t), 3.76 (2H, t), 3.66 (2H, t), 3.33 (1H, br), 2.65 (2H, q), 2.57 (2H, q), 1.96 (2H, m), 1.84 (2H, m), 1.28 (3H, t), 1.14 (3H, t), 1.12 (3H, t)

166

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-hy droxyprop-2-yl)-4-n-propoxybenzamide (CDCl3) δ : 8.75 (1H, d), 7.94 (1H, dd), 6.97 (1H, d), 4.28 (1H, m), 4.10 (2H, t), 3.84 (1H, dd), 3.69 (1H, dd), 2.66 (2H, q), 2.57 (2H, q), 1.92 (2H, m), 1.33 (3H, d), 1.28 (3H, t), 1.16 (3H, t), 1.10 (3H, t)

167

N-ethyl-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-hydroxyethyl)-4-n-propoxybenzamide (CDCl3) δ: 11.14 (1H, br), 8.62 (1H, d), 7.61 (1H, dd), 7.07 (1H, d), 4.20 (2H, t), 3.90 (2H, t), 3.71 (2H, t), 3.42 (2H, q), 2.66 (2H, q), 2.58 (2H, q), 2.00 (2H, m), 1.27 (3H, t), 1.26 (3H, t), 1.15 (3H, t), 1.14 (3H, t)

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(continued)

Example structural formula nomenclature and data of 1H-NMR(δ )

168

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-die thylaminoethyl)-4-n-propoxybenzamide (CDCl3) δ : 11.08 (1H, br), 8.84 (1H, d), 8.04 (1H, dd), 7.09 (1H, d), 4.22 (2H, t), 3.49 (2H, m), 2.71-2.53 (10H, m), 2.01 (2H, m), 1.29 (3H, t), 1.15 (6H, t), 1.07 (6H, t)

169

3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)propyl-1-sulfonic acid (DMSO-d6) δ : 8.22 (1H, d), 8.13 (1H, dd), 7.33 (1H, d), 4.11 (2H, t), 3.32 (2H, t), 2.68 (2H, q), 2.57 (4H, m), 1.83 (2H, m), 1.73 (2H, m), 1.22 (3H, t), 1.08 (3H, t), 0.93 (3H, t)

170

2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)ethylsulfonic acid (DMSO-d6) δ: 8.17 (1H, d), 8.06 (1H, dd), 7.35 (1H, d), 4.11 (2H, t), 3.53 (2H, t), 2.68 (4H, m), 2.58 (2H, q), 1.73 (2H, m), 1.22 (3H, t), 1.08 (3H, t), 0.93 (3H, t)

171

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-hy droxyethyl)-N-methyl-4-n-propoxybenzamide (CDCl3) δ: 11.08 (1H, br), 8.60 (1H, d), 7.62 (1H, dd), 7.05 (1H, d), 4.19 (2H, t), 3.91 (2H, t), 3.74 (2H, t), 3.12 (3H, s), 2.66 (2H, q), 2.58 (2H, q), 2.00 (2H, m), 1.27 (3H, t), 1.14 (6H, t)

172

(4-benzylpiperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-ox opyrimidin-2-yl)-4-n-propoxybenzophenone (CDCl3) δ : 11.08 (1H, br), 8.58 (1H, d), 7.57 (1H, dd), 7.31 (5H, m), 7.05 (1H, d), 4.19 (2H, t), 3.78 (4H, br), 3.55 (2H, s), 2.66 (2H, q), 2.58 (2H, q), 2.50 (4H, br), 2.00 (2H, m), 1.29 (3H, t), 1.14 (6H, t)

173

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-meth yl-N-(2-(pyrrolidin-1-yl)ethyl)-4-n-propoxybenzamide (DMSO-d6) δ: 7.84 (1H, d), 7.79 (1H, dd), 7.26 (1H, d), 4.09 (2H, t), 3.79 (2H, t), 3.49 (2H, t), 3.41 (2H, t), 3.06 (2H, t), 3.02 (3H, s), 2.63 (2H, q), 2.54 (2H, q), 1.99 (2H, m), 1.88 (2H, m), 1.74 (2H, m), 1.19 (3H, t), 1.05 (3H, t), 0.95 (3H, t)

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Example 176

5,6-Diethyl-2-[2-(3-methoxy-n-propoxy)-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimi d-4(3H)-one

[0235]

[0236] According to the same manner as that of example 10, the compound of preparation example 36 was firstchlorosulfonated, and then reacted with N-methylpiperazine to obtain the title compound. 1H NMR (CDCl3) δ: 11.08 (1H,br), 8.78 (1H, d), 7.83 (1H, dd), 7.14 (1H, d), 4.38 (2H, t), 3.65 (2H, t), 3.40 (3H, s), 3.10 (4H, t), 2.66 (2H, q), 2.59 (2H,q), 2.53 (4H, t), 2.30 (3H, s), 2.22 (2H, m), 1.27 (3H, t), 1.15 (3H, t).

Example 177

2-Chloro-N-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)acetamide

[0237]

[0238] The compound(0.74g, 2mmol) of example 34 was dissolved in dichloromethane(20ml), added with triethyl-

(continued)

Example structural formula nomenclature and data of 1H-NMR(δ )

174

methyl 5-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)piperidine-2-formate (DMSO-d6) δ : 8.16 (1H, d), 8.11 (1H, d), 7.97 (1H, dd), 7.20 (1H, d), 4.07 (2H, t), 3.78 (1H, br), 3.63 (3H, s), 3.22 (1H, m), 3.05 (1H, m), 2.57 (2H, q), 2.46 (2H, q), 2.40 (2H, m), 1.94 (2H, m), 1.73 (2H, m), 1.47 (2H, m), 1.18 (3H, t), 1.03 (3H, t), 0.95 (3H, t)

175

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-meth oxy-N-methyl-4-n-propoxybenzamide (CDCl3) δ : 11.08 (1H, br), 8.91 (1H, d), 7.87 (1H, dd), 7.05 (1H, d), 4.21 (2H, t), 3.62 (3H, s), 3.38 (3H, s), 2.66 (2H, q), 2.59 (2H, q), 2.01 (2H, m), 1.28 (3H, t), 1.15 (3H, t), 1.14 (3H, t)

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amine(2ml), followed by slow addition of chloroacetyl chloride(0.23g, 2.05mmol) under ice water bath. After stirred for0.5h, the reaction mixture was washed with water (10ml), 1N HCl(5ml), saturated sodium bicarbonate solution(10ml)and saturated saline respectively. The organic phase was dried with anhydrous Na2SO4 and concentrated. The resultantoil was recrystallized from ethyl acetate-petroleum ether to give the title compound(0.71g, yield: 94%). 1H NMR (CDCl3)δ: 11.16 (1H, br), 9.09 (1H, br), 8.27 (1H, d), 8.00 (1H, dd), 7.01 (1H, d), 4.15 (2H, t), 3.18 (2H, s), 2.68 (2H, q), 2.58(2H, q), 1.97 (2H, m), 1.31 (3H, t), 1.15 (3H, t), 1.13 (3H, t).

Example 178

2-(Dimethylamino)-N-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl )acetamide

[0239]

[0240] The compound(0.38g, 1mmol) of example 177 was suspended in a 33% dimethylamine solution(20ml), sealedinto a tube, and heated to 60°C to stir for 10h. The reaction mixture was concentrated to dryness, washed with waterand dried. The resultant solid was recrystalllized from ethyl acetate to obtain the title compound(0.36g, yield: 93.2%).1H NMR (DMSO-d6) δ: 11.81 (1H, br), 9.82 (1H, br), 8.03 (1H, d), 7.78 (1H, dd), 7.12 (1H, d), 4.02 (2H, t), 3.09 (2H, s),2.57 (2H, q), 2.46 (2H, q), 2.29 (6H, s), 1.74 (2H, m), 1.20 (3H, t), 1.04 (3H, t), 0.97 (3H, t).

Examples 179~182

[0241] The title compounds were prepared by reacting the compound of example 77 with N-methylpiperazine, mor-pholine, piperidine and trimethyl phosphite respectively in the same manner as that of example 178.

Example structural formula nomenclature and data of 1H-NMR(δ)

179

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-(4-methylpiperazin-1-yl)acetamide (CDCl3) δ : 11.17 (1H, br), 9.10 (1H, br), 8.27 (1H, d), 7.99 (1H, dd), 7.00 (1H, d), 4.15 (2H, t), 3.16 (2H, s), 2.80-2.50 (12H, m), 2.36 (3H, s), 1.97 (2H, m), 1.31 (3H, t), 1.14 (3H, t), 1.13 (3H, t)

180

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-morpholinyl)acetamide (CDCl3) δ : 11.16 (1H, br), 9.09 (1H, br), 8.27 (1H, d), 8.00 (1H, dd), 7.01 (1H, d), 4.15 (2H, t), 3.81 (4H, t), 3.18 (2H, s), 2.68 (2H, q), 2.66 (4H, t), 2.58 (2H, q), 1.97 (2H, m), 1.31 (3H, t), 1.15 (3H, t), 1.13 (3H, t)

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Examples 183~188

[0242] The compounds of examples 183~188 were prepared by reacting the compound of example 42 with isobutyrylchloride, isovaleryl chloride, phenylacetyl chloride, benzoyl chloride and ethyl succinyl chloride and pyroglutamyl chloriderespectively in the same manner as that of example 50.

(continued)

Example structural formula nomenclature and data of 1H-NMR(δ)

181

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-(piperid-1-yl)acetamide (CDCl3) δ : 11.17 (1H, br), 9.27 (1H, br), 8.28 (1H, d), 7.99 (1H, dd), 7.01 (1H, d), 4.15 (2H, t), 3.10 (2H, s), 2.68 (2H, q), 2.59 (2H, q), 2.56 (4H, t), 1.97 (2H, m), 1.66 (4H, m), 1.50 (2H, m), 1.31 (3H, t), 1.15 (3H, t), 1.13 (3H, t)

182

dimethyl (3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-pro poxyphenylaminoformyl)methylphosphate (CDCl3) δ : 11.10 (1H, br), 8.87 (1H, br), 8.34 (1H, d), 7.87 (1H, dd), 6.93 (1H, d), 4.11 (2H, t), 3.85 (6H, d), 3.07 (2H, d), 2.65 (2H, q), 2.58 (2H, q), 1.96 (2H, m), 1.27 (3H, t), 1.14 (3H, t), 1.12 (3H, t)

Example structural formula nomenclature and data of 1H-NMR(δ )

183

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)isobutyramide (CDCl3) δ : 8.21 (1H, d), 8.09 (1H, dd), 7.33 (1H, br), 6.99 (1H, d), 4.14 (2H, t), 2.66 (2H, q), 2.58 (2H, q), 2.53 (1H, q), 1.97 (2H, m), 1.29 (3H, t), 1.27 (6H, d), 1.15 (3H, t), 1.13 (3H, t)

184

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-methylbutyramide (CDCl3) δ: 8.22 (1H, d), 8.07 (1H, dd), 7.39 (1H, br), 6.99 (1 H, d), 4.13 (2H, t), 2.66 (2H, q), 2.58 (2H, q), 2.23 (2H, d), 2.20 (1H, m), 1.96 (2H, m), 1.28 (3H, t), 1.14 (3H, t), 1.12 (3H, t), 1.02 (6H, d)

185

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-phenylacetamide (CDCl3) δ : 8.11 (1H, d), 7.93 (1H, dd), 7.37 (5H, m), 6.96 (1H, d), 4.11 (2H, t), 3.75 (2H, s), 2.64 (2H, q), 2.57 (2H, q), 1.95 (2H, m), 1.26 (3H, t), 1.13 (3H, t), 1.11 (3H, t)

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Examples 189~193

[0243] According to the same manner as those of example 106 and example 107, the compound of example 42 wasreacted with N-Boc-leucine, N-Boc-tryptophan, N-Boc-glutamine, N-Boc-threonine and N-Boc-serine respecitvly, andthen removed the Boc-protecting group and acetylated to obtain the compounds of examples 189~193.

(continued)

Example structural formula nomenclature and data of 1H-NMR(δ )

186

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)benzamide (CDCl3) δ : 8.37 (1H, d), 8.11 (1H, dd), 8.04 (1H, br), 7.91 (2H, d), 7.52 (3H, m), 7.05 (1H, d), 4.17 (2H, t), 2.67 (2H, q), 2.58 (2H, q), 1.98 (2H, m), 1.29 (3H, t), 1.15 (3H, t), 1.14 (3H, t)

187

ethyl 3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxyphenylaminoformyl)propionate (CDCl3) δ: 8.26 (1H, d), 7.99 (1H, dd), 7.66 (1H, br), 6.98 (1H, d), 4.18 (2H, t), 4.15 (2H, q), 2.75 (2H, t), 2.66 (4H, m), 2.58 (2H, q), 1.96 (2H, m), 1.30 (3H, t), 1.27 (3H, t), 1.15 (3H, t), 1.12 (3H, t)

188

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-5-oxopyrrolidine-2-formamide (DMSO-d6) δ: 10.13 (1H, br), 8.02 (1H, d), 7.97 (1H, dd), 7.15 (1H, d), 4.16 (1H, dd), 4.03 (2H, t), 2.56 (2H, q), 2.46 (2H, q), 2.39-1.92 (4H, m), 1.75 (2H, m), 1.19 (3H, t), 1.03 (3H, t), 0.97 (3H, t),

Example structural formula nomenclature and data of 1H-NMR(δ)

189

2-acetamido-N-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidi n-2-yl)-4-n-propoxyphenyl)-4-methylvaleramide (CDCl3) δ : 8.99 (1H, br), 8.34 (1H, d), 7.91 (1H, dd), 6.94 (1H, d), 6.39 (1H, br), 4.70 (1H, m), 4.11 (2H, t), 2.75 (2H, t), 2.65 (2H, q), 2.58 (2H, q), 2.07 (3H, s), 1.95 (2H, m), 1.82-1.56 (3H, m), 1.27 (3H, t), 1.14 (3H, t), 1.11 (3H, t), 0.94 (6H, d)

190

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-acetamido-3-(1H-indol-3-yl)propiona mide (DMSO-d6) δ: 10.17 (1H, br), 8.02 (1H, d), 7.74 (1H, dd), 7.64 (1H, d), 7.31 (1H, d), 7.16 (1H, s), 7.13 (1H, d), 7.05 (1H, t), 6.97 (1H, t), 4.67 (1H, dd), 4.02 (2H, t), 3.15 (1H, dd), 2.98 (1H, dd), 2.57 (2H, q), 2.46 (2H, q), 1.81 (3H, s), 1.74 (2H, m), 1.20 (3H, t), 1.04 (3H, t), 0.97 (3H, t)

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Example 194

2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylaminoformyl)-2-ace tamidoethyl acetate

[0244]

[0245] At room temperature, the compound(0.21g, 0.5mmol) of example 193 was dissolved in dichloromethane(10ml),and added with pyridine(40mg, 0.5mmol) and acetic anhydride(51mg, 0.5mmol). 0.5h later, TLC showed that the reactionwas complete. The reaction mixture was washed with 1N hydrochloric acid(2ml), water(10ml) and saturated saline(10ml)respectively. The organic layer was dried with anhydrous sodium sulfate, and concentrated. The residue was passedthrough a silica gel column to give the white title compound(175mg, yield: 74%). 1H NMR (CDCl3) δ: 9.49 (1H, br), 8.33(1H, d), 7.89 (1H, dd), 6.97 (1H, d), 6.92 (1H, d), 5.11 (1H, m), 4.51 (1H, dd), 4.39 (1H, dd), 4.08 (2H, t), 2.60 (2H, q),2.55 (2H, q), 2.12 (3H, s), 2.06 (3H, s), 1.92 (2H, m), 1.23 (3H, t), 1.12 (3H, t), 1.09 (3H, t)

Example 195

5,6-Diethyl-2-(5-(ethylamino)-2-n-propoxyphenyl)pyrimid-4(3H)-one

[0246]

(continued)

Example structural formula nomenclature and data of 1H-NMR(δ)

191

2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimid in-2-yl)-4-n-propoxyphenyl)glutaramide (DMSO-d6) δ: 8.05 (1H, d), 7.76 (1H, dd), 7.13 (1H, d), 4.32 (1H, m), 4.02 (2H, t), 2.56 (2H, q), 2.45 (2H, q), 2.13 (2H, m), 1.91 (2H, m), 1.87 (3H, s), 1.74 (2H, m), 1.19 (3H, t), 1.03 (3H, t), 0.96 (3H, t)

192

2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimid in-2-yl)-4-n-propoxyphenyl)-3-hydroxybutyramide (DMSO-d6) δ: 9.95 (1H, br), 8.02 (1H, d), 7.75 (1H, dd), 7.14 (1H, d), 4.30 (1H, d), 4.02 (3H, m), 2.57 (2H, q), 2.46 (2H, q), 1.92 (3H, s), 1.74 (2H, m), 1.19 (3H, t), 1.08 (3H, d), 1.03 (3H, t), 0.96 (3H, t)

193

2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimid in-2-yl)-4-n-propoxyphenyl)-3-hydroxypropionamide (DMSO-d6) δ : 10.05 (1H, br), 8.07 (1H, d), 8.06 (1H, d), 7.76 (1H, dd), 7.13 (1H, d), 4.42 (1H, m), 4.03 (2H, t), 3.61 (2H, d), 2.56 (2H, q), 2.45 (2H, q), 1.74 (2H, m), 1.19 (3H, t), 1.03 (3H, t), 0.97 (3H, t)

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[0247] The compound(2.2g, 7.3mmol) of example 42 was dissolved in 50ml of 80 % acetonitrile acqueous solution,and added with 0.14g of 5% Pd/C and 5g of ammonium formate,followed by stirring at room temperature for 20h undernitrogen atmosphere. The reaction mixture was filtered off Pd/C and distilled off the solvent. The residue was dissolvedin CH2Cl2(50ml), washed with water(50ml) and saturated saline(50ml), dried with anhydrous Na2SO4, and concentratedto dryness to give a white solid crude, which was passed through a silica gel column (eluant: 10% petroleumether-ethylacetate) to afford the title compound(1.9g, yield: 79%). 1H NMR (CDCl3) δ: 8.38 (1H, d), 7.33 (1H, dd), 7.04 (1H, d),4.19 (2H, t), 4.04 (2H, q), 2.66 (2H, q), 2.59 (2H, q), 2.01 (2H, m), 1.28 (3H, t), 1.19 (3H, t), 1.15 (3H, t), 1.06 (3H, t).

Examples 196~197

[0248] The compounds of examples 196 and 197 were prepared by reacting the compound of example 195 withpropionyl chloride and ethyl oxalyl monochloride respectively in the same manner as that of example 50.

Examples 198

1,3-Diethyl-1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea

[0249]

Example structural formula nomenclature and data of 1H-NMR(δ )

196

N-ethyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)propionamide (DMSO-d6) δ : 11.94 (1H, br), 7.55 (1H, d), 7.40 (1H, dd), 7.21 (1H, d), 4.06 (2H, t), 3.61 (2H, q), 2.55 (2H, q), 2.45 (2H, q), 1.96 (2H, q), 1.75 (2H, m), 1.17 (3H, t), 1.03 (3H, t), 0.99 (3H, t), 0.97 (3H, t), 0.90 (3H, t)

197

ethyl (N-ethyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2 -yl)-4-n-propoxyphenyl)aminoformylformate (CDCl3) δ: 8.38 (1H, d), 7.33 (1H, dd), 7.04 (1H, d), 4.19 (2H, t), 4.04 (2H, q), 3.84 (2H, q), 2.66 (2H, q), 2.59 (2H, q), 2.01 (2H, m), 1.28 (3H, t), 1.19 (3H, t), 1.15 (3H, t), 1.14 (3H, t), 1.06 (3H, t)

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[0250] The compound(0.33g, 1mmol) of example 195 was dissolved in ethanol(10ml), and added with ethyl isocy-anate(0.8g, 1.1mmol). After refluxed for 1h, the reaction mixture was concentrated to dryness. The resultant solid wasrecrystallized from ethyl acetate-petroleum ether to obtain the title compound(0.32g, yield: 80%). 1H NMR (DMSO-d6)δ: 11.81 (1H, br), 7.58 (1H, d), 7.30 (1H, dd), 7.19 (1H, d), 5.65 (1H, t), 4.07 (2H, t), 3.55 (2H, q), 3.00 (2H, m), 2.56 (2H,q), 2.46 (2H, q), 1.77 (2H, m), 1.18 (3H, t), 1.04 (3H, t), 0.99 (3H, t), 0.98 (3H, t), 0.95 (3H, t).

Example 199

N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)piperidine-1-form amide

[0251]

[0252] The compound(1g, 3.3mmol) of example 42 was dissolved in dichloromethane(10ml), and added with N,N’-carbonyldiimidazole(589mg, 3.63mmol), followed by stirring at room temperature for 2h. A precipitate was generated,and TLC showed that the reaction was complete. The reaction mixture was filtered, and the resultant white solid(1g)was added into piperidine(10ml), and heated to 80°C to stir for 5h. TLC showed that the reaction was complete. Thereaction mixture was cooled down to room temperature, and added with dichloromethane. The organic layer was washedwith water and saturated saline, dried with anhydrous sodium sulfate and concentrated to give an oily crude, which waspassed through a column to obtain the title compound(300mg, yield: 22%). 1H NMR (CDCl3) δ: 8.08 (1H, d), 7.80 (1H,dd), 6.98 (1H, d), 6.49 (1H, br), 4.12 (2H, t), 3.46 (4H, t), 2.66 (2H, q), 2.58 (2H, q), 1.96 (2H, m), 1.64 (6H, m), 1.29(3H, t), 1.14 (3H, t), 1.12 (3H, t).

Examples 200~203

[0253] According to the same manner as that of example 199, the compound of example 42 was first reacted withN,N’- carbonyldiimidazole to give an intermediate, which was then reacted with N-methylpiperazine, n-propylamine,cyclohexylamine and diethylamine respectively to provide the compounds of examples 200~203.

Example structural formula nomenclature and data of 1H-NMR(δ )

200

N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-4-methylpiperazine-1-formamide (DMSO-d6) δ : 11.76 (1H, br), 8.55 (1H, br), 7.83 (1H, d), 7.60 (1H, dd), 7.07 (1H, d), 4.01 (2H, t), 3.43 (4H, t), 2.56 (2H, q), 2.46 (2H, q), 2.32 (4H, t), 2.20 (3H, s), 1.74 (2H, m), 1.19 (3H, t), 1.03 (3H, t), 0.97 (3H, t)

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Example 204

1-(2-(Diethylamino)ethyl)-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxy phenyl)urea maleate

[0254]

[0255] The compound(1g, 3.3mmol) of example 42 was dissolved in dichloromethane(10ml), and added with N,N’-carbonyldiimidazole(589mg, 3.63mmol), followed by stirring at room temperature for 2h to generate a solid. TLC showedthat the reaction was complete. The reaction mixture was filtered, the resultant white solid(1g) was added into N,N’-diethylethylenediamine(10ml), and heated to 80°C to stir for 5h. TLC showed that the reaction was complete. The reactionmixture was cooled down to the room temperature, and added with dichlormethane. The organic layer was washed withwater and saturated saline, dried with anhydrous sodium sulfate and concentrated to give an oily crude, which waspassed through a column to obtain the title compound(300mg) in alkaline form. The compound was dissolved in ace-tone(3ml), added with maleic acid(79mg, 0.677mmol), and stirred for 10h to generate a solid, which was filtered anddried to obtain the title compound(300mg, yield: 16%). 1H NMR (DMSO-d6) δ: 7.84 (1H, d), 7.56 (1H, dd), 7.09 (1H, d),6.04 (2H, s), 4.01 (2H, t), 3.42 (2H, t), 3.17 (6H, m), 2.56 (2H, q), 2.45 (2H, q), 1.74 (2H, m), 1.20 (6H, t), 1.18 (3H, t),1.03 (3H, t), 0.97 (3H, t).

(continued)

Example structural formula nomenclature and data of 1H-NMR(δ )

201

1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxyphenyl)-3-propylurea (DMSO-d6) δ : 11.71 (1H, br), 8.42 (1H, br), 7.79 (1H, d), 7.57 (1H, dd), 7.06 (1H, d), 6.03 (1H, t), 4.01 (2H, t), 3.03 (2H, t), 2.57 (2H, q), 2.46 (2H, q), 1.74 (2H, m), 1.43 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.97 (3H, t), 0.87 (3H, t)

202

1-cyclohexyl-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimid in-2-yl)-4-n-propoxyphenyl)urea (DMSO-d6) δ : 8.33 (1H, br), 7.77 (1H, d), 7.54 (1H, dd), 7.06 (1H, d), 5.96 (1H, d), 4.00 (2H, t), 3.44 (1H, m), 2.56 (2H, q), 2.45 (2H, q), 1.84-1.24 (12H, m), 1.19 (3H, t), 1.03 (3H, t), 0.96 (3H, t)

203

1,1-diethyl-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin -2-yl)-4-n-propoxyphenyl)urea (CDCl3) δ: 8.13 (1H, d), 7.93 (1H, dd), 6.99 (1H, d), 6.42 (1H, br), 4.14 (2H, t), 3.40 (4H, q), 2.69 (2H, q), 2.58 (2H, q), 1.97 (2H, m), 1.30 (3H, t), 1.24 (6H, t), 1.15 (3H, t), 1.13 (3H, t)

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Example 205

(4-Methylpiperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyben zophenone

[0256]

[0257] According to the same manner as that of example 89, the compound of example 58 was first reacted withthionyl chloride, and the resultant product was reacted with N-methylpiperazine to give the title compound. 1H NMR(CDCl3) δ: 11.08 (1H, br), 8.58 (1H, d), 7.57 (1H, dd), 7.06 (1H, d), 4.19 (2H, t), 3.68 (4H, br), 2.65 (2H, q), 2.58 (2H, q),2.45 (4H, br), 2.33 (3H, s), 2.00 (2H, m), 1.28 (3H, t), 1.14 (6H, t).

Example 206

5-Iodo-6-isopropyl-2-[2-n-propoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3 H)-one

[0258]

[0259] The compound(1.69g, 3.9mmol) of example 1 was added into methanol(15ml), and added with silver ni-trate(0.66g, 3.9mol), and then with I2 grain(0.98g, 3.9mmol) under stirring. The reaction mixture was stirred at roomtemperature for 0.5h, and TLC showed that the reaction was complete. The reaction mixture was filtered, and the filtratewas concentrated. The concentrate was washed with water, extracted with dichloromethane. The organic layer waswashed with saturated saline, dried with anhydrous sodium sulfate, and concentrated. The residue was recrystallizedfrom ethyl acetate to give a yellowish solid(1.52g, yield: 70%). 1H NMR (CDCl3) δ: 8.90 (1H, d), 7.89 (1H, dd), 7.16 (1H,d), 4.27 (2H, t), 3.46 (1H, m), 3.08 (4H, t), 2.49 (4H, t), 2.27 (3H, s), 2.03 (2H, m), 1.25 (6H, d), 1.16 (3H, t).

Example 207

5-Chloro-6-ethyl-2-[2-n-propoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one

[0260]

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[0261] The compound(0.42g, Immol) of example 6 was dissolved in CH2Cl2 (20ml), added with pyridine(0.3ml), andfed with chlorine gas for about 2min under ice-bath. The reaction mixture was washed with 1M Na2S2O3(20ml), 1MHCl(20ml) and saturated saline(40ml) respectively. The organic phase was dried with anhydrous sodium sulfate, andconcentrated to dryness under reduced pressure. The residue was recrystallized from acetonitrile-ethylether to give thetitle compound (0.41g, yield: 90%). 1H NMR (CDCl3) δ: 11.25 (1H, br), 8.85 (1H, d), 7.87 (1H, dd), 7.16 (1H, d), 4.27(2H, t), 3.08 (4H, t), 2.85 (2H, q), 2.49 (4H, t), 2.27 (3H, s), 2.03 (2H, m), 1.29 (3H, t), 1.15 (3H, t).

Example 208

5,6-Diethyl-2-(2-n-propoxy-5-((tetrahydro-2,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-3 -ylamino)sulfonyl)phenyl]py-rimid-4(3H)-one

[0262]

[0263] According to the same manner as that of example 10, the compound of preparation example 33 was firstchlorosulfonated, and then reacted with aminoglucose to give the compound of example 208. 1HNMR (CDCl3) 11.02(1H, s), 8.52 (1H, s), 7.96 (1H, d), 7.12 (1H, d), 4.06 (2H, t), 3.52~3.84 (5H, m), 3.35 (1H, m), 3.15 (1H, m), 2.52 (2H,q), 2.49 (2H, q), 1.80 (2H, m), 1.24 (3H, t), 1.06 (3H, t), 0.84 (3H, t).

Example 209

[0264] According to the same manner as that of example 89, the compound of example 58 was first reacted withthionyl chloride, and the resultant product was reacted with citrulline, ornithine and aminosugar respectively to obtainthe compounds of examples 209-211.

Example structural formula nomenclature and data of 1H-NMR(δ)

209

2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)-5-ureavaleric acid (DMSO-d6) δ : 8.19 (1H, d), 8.04 (1H, dd), 7.23 (1H, d), 4.34 (1H, m), 4.08 (2H, t), 2.97 (2H, m), 2.56 (2H, q), 2.44 (2H, q), 1.75 (4H, m), 1.45 (2H, m), 1.18 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

210

2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-aminovaleric acid (DMSO-d6) δ: 8.14 (1H, d), 7.97 (1H, dd), 7.20 (1H, d), 4.07 (2H, t), 3.59 (1H, m), 3.28 (2H, t), 2.56 (2H, q), 2.46 (2H, q), 1.84 (2H, m), 1.74 (2H, m), 1.63 (2H, m), 1.17 (3H, t), 1.03 (3H, t), 0.95 (3H, t)

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Example 212~214

[0265] According to the same manner as that of example 89, the compound of example 170 was first reacted withthionyl chloride, and the resultant product was reacted with ammonia, N-methylpiperazine and diethylamine respectivelyto obtain the compounds of examples 212-214.

Example 215~217

[0266] According to the same manner as that of example 89, the compound of example 169 was first reacted withthionyl chloride, and the resultant product was reacted with ammonia, N-methylpiperazine and diethylamine respectivelyto obtain the compounds of examples 215-217.

(continued)

Example structural formula nomenclature and data of 1H-NMR(δ)

211

3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(te trahydro-2,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-3 -yl)-4-n-propoxybenzamide (DMSO-d6) δ : 8.20 (1H, d), 8.05 (1H, m), 7.22 (1H, d), 4.08 (1H, t), 3.6~3.8 (5H, m), 3.50 (1H, dd), 3.19 (1H, t), 2.58 (2H, q), 2.47 (2H, q), 1.68 (2H, m), 1.19 (3H, t), 1.05 (3H, t), 0.95 (3H, t)

Example structural formula nomenclature and data of 1H-NMR(δ)

212

2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)ethylsulphonamide (DMSO-d6) δ : 8.13 (1H, d), 7.96 (1H, dd), 7.24 (1H, d), 4.08 (2H, t), 3.64 (2H, t), 3.24 (2H, t), 2.57 (2H, q), 2.46 (2H, q), 1.74 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

213

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-me thyl-1-piperazinylsulfonylethyl)-4-n-propoxybenzamide (CDCl3) δ: 11.00 (1H, br), 8.84 (1H, d), 7.94 (1H, dd), 7.18 (1H, t), 7.05 (1H, d), 4.19 (2H, t), 3.97 (2H, q), 3.32 (4H, t), 3.19 (2H, t), 2.66 (2H, q), 2.57 (2H, q), 2.48 (4H, t), 2.31 (3H, s), 1.98 (2H, m), 1.29 (3H, t), 1.13 (6H, t)

214

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylethyl)-4-n-propoxybenzamide (CDCl3) δ : 8.86 (1H, d), 7.95 (1H, dd), 7.05 (1H, d), 4.19 (2H, t), 3.94 (2H, m), 3.31 (4H, q), 3.19 (2H, t), 2.66 (2H, q), 2.57 (2H, q), 1.98 (2H, m), 1.29 (3H, t), 1.21 (6H, t), 1.13 (6H, t)

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Example 218

5,6-Diethyl-2-(5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yl)-2-n-propo xyphenyl)pyrimid-4(3H)-one

[0267]

[0268] The compound(728mg, 2mmol) of preparation example 34 was dissolved in tetrahydrofuran(4mL), and addedslowly with a 1.6mol/L n-BuLi solution(2.8mL, 4.4mmol) in n-hexane at -78 °C, the dropping speed being controlled tokeep the temperature below -70°C. 40min later, gluconolactone protected by trimethylsilicane and dissolved in 4mL oftoluene was slowly added dropwise into the reaction system. The reaction temperature was kept below -70°C for 1hand then raised to -40°C to stir for 30min. A methanol solution(4mL) of methanesulfonic acid(0.38mL, 6.0mmol) wasslowly added dropwise into the reaction system. After the addition, the reaction mixture was slowly raised to roomtemperature and stirred for 8h, added with saturated sodium bicarbonate to adjust to a PH of 8, and extracted with ethylacetate. The organic phase was washed with saturated saline , dried with anhydrous sodium sulfate, and concentratedto dryness to give a yellow oil, which was passed through a silica gel column(petroleum ether:ethyl acetate=1:4) to obtainan intermediate(380mg). The intermediate (380mg, 0.8mmol) was dissolved in 5mL of acetonitrile, and added withtriethylsilicane(0.4mL, 2.3mml) and boron trifluoride diethyl ether(0.1mL, 1.6mmol) under ice-bath, followed by stirringunder ice-bath for 40min. The stirring continued at room temperature for another 3h, and TLC showed that the reactionwas complete. The reaction mixture was adjusted to a PH of 7 with saturated sodium bicarbonate solution, and extractedwith ethyl acetate. The organic phase was washed with saturated saline, dried with anhydrous sodium sulfate, andconcentrated to dryness. The residue was recrystallized from ethyl acetate-ethanol to obtain the title compound(300mg,yield: 34%). 1H NMR (CDCl3) 8.60 (1H , s), 7.72 (1H, s), 7.53 (1H, d), 7.02 (1H, d), 4.03 (2H, t), 3.85 (3H, m), 3.66 (2H,m), 3.55 (1H, m), 3.23 (1H, d), 2.74 (2H, q), 2.58 (2H, q), 1.54 (2H, m), 1.24 (3H, t), 1.10 (3H, t), 1.05 (3H, t).

Example structural formula nomenclature and data of 1H-NMR(δ)

215

3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-p ropoxybenzamido)propylsulphonamide (DMSO-d6) δ : 12.02 (1H, br), 8.58 (1H, t), 8.13 (1H, d), 7.98 (1H, dd), 7.23 (1H, d), 6.79 (2H, s), 4.07 (2H, t), 3.36 (2H, m), 3.01 (2H, t), 2.58 (2H, q), 2.47 (2H, q), 1.93 (2H, m), 1.74 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.96 (3H, t)

216

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-me thyl-1-piperazinylsulfonylpropyl)-4-n-propoxybenzamide (CDCl3) δ: 10.97 (1H, br), 8.80 (1H, d), 7.97 (1H, dd), 7.05 (1H, d), 6.90 (1H, t), 4.18 (2H, t), 3.65 (2H, q), 3.30 (4H, t), 3.03 (2H, t), 2.67 (2H, q), 2.58 (2H, q), 2.48 (4H, t), 2.32 (3H, s), 2.20 (2H, m), 1.98 (2H, m), 1.27 (3H, t), 1.15 (3H, t), 1.14 (3H, t)

217

3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylpropyl)-4-n-propoxybenzamide (CDCl3) δ: 10.93 (1H, br), 8.78 (1H, d), 7.92 (1H, dd), 7.16 (1H, t), 6.99 (1H, d), 4.13 (2H, t), 3.62 (2H, q), 3.28 (4H, q), 3.04 (2H, t), 2.64 (2H, q), 2.56 (2H, q), 2.16 (2H, m), 1.93 (2H, m), 1.27 (3H, t), 1.18 (6H, t), 1.13 (3H, t), 1.10 (3H, t)

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Example 219

5-lodo-6-ethyl-2-(2-n-propoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-o ne

[0269]

[0270] The compound of example 219 was prepared by reacting the compound of example 6 with I2 in the samemanner as that of example 206. 1H NMR (CDCl3) 11.12 (1H, br), 8.88 (1H , d), 7.88 (1H, dd), 7.16 (1H, d), 4.27 (2H, t),3.10 (4H, t), 2.92 (2H, q), 2.52 (4H, t), 2.30 (3H, s), 2.03 (2H, m), 1.28 (3H, t), 1.16 (3H, t).

Example 220

5-Bromo-6-ethyl-2-[2-n-propoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one

[0271]

[0272] The compound of example 220 was prepared by reacting the compound of example 6 with liquid bromine inthe same manner as that of preparation example 19. 1H NMR (CDCl3) 11.20 (1H, br), 8.86 (1H, d), 7.88 (1H, dd), 7.16(1H, d), 4.27 (2H, t), 3.09 (4H, t), 2.88 (2H, q), 2.50 (4H, t), 2.28 (3H, s), 2.03 (2H, m), 1.29 (3H, t), 1.15 (3H, t).

Example 221

5-Chloro-6-isopropyl-2-[2-n-propoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4( 3H)-one

[0273]

[0274] The compound of example 221 was prepared by reacting the compound of example 1 with chlorine gas in thesame manner as that of example 207. 1H NMR (CDCl3) 8.86 (1H , d), 7.88 (1H, dd), 7.16 (1H, d), 4.27 (2H, t), 3.49 (1H,m), 3.09 (4H, t), 2.50 (4H, t), 2.27 (3H, s), 2.03 (2H, m), 1.26 (6H, d), 1.16 (3H, t).

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Example 222 Capsule

[0275]

[0276] The said phenylpyrimidone compound and the adjuvants, i.e. starch, lactose and microcrystalline cellulose,were screened with a 80 mesh sieve, weighed according to the formula, granulated into suitable granules with a 16mesh sieve using a 10% ethanol solution of polyvinyl pyrrolidone as the adhesive, dried at 65°C, sized with a 14 meshsieve, and added with magnesium stearate to mix uniformly. Then, the content of the granules was measured, and theloading amount was calculated. A suitable amount of granules were put into the capsules, thereby to obtain the finalproduct.

Example 223 Tablet (wet granulation)

[0277]

[0278] The said phenylpyrimidone compound, microcrystalline cellulose, lactose and sodium carboxymethyl starchwere screened with a 80 mesh sieve, mixed uniformly, prepared into a damp mass with a 8% starch paste, granulatedwith a 16 mesh sieve, dried,sized with a 14 mesh sieve, and added with magnesium stearate to mix uniformly. Then,the content of the granules was measured, and the weigh of the tablet was calculated. Tabletting was performed toobtain the final product.

Example 224 Tablet (powder compression)

[0279]

[0280] The saided phenyl pyrimidone compound, microcrystalline cellulose, anhydrous lactose, polyvinylpyrrolidone

Formulaphenylpyrimidone compound(Example 46) 20.0gstarch 80.0glactose 60.0gmicrocrystalline cellulose 35.0g

10% ethanol solution of polyvinyl pyrrolidone suitable amountmagnesium stearate 0.5g

total 1000 capsules

Formula

phenylpyrimidone compound(Example 50) 20.0glactose 120.0gmicrocrystalline cellulose 40.0g8% starch paste suitable amountsodium carboxymethyl starch 10.0gmagnesium stearate 1.0 g

total 1000 tablets

Formulaphenylpyrimidone compound(Example53) 20.0gmicrocrystalline cellulose 30.0ganhydrous lactose 45.0gpolyvinylpyrrolidone 3.0g

silica gel 0.2gmagnesium stearate 0.5g

total 1000 tablets

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and silica gel were mixed uniformly in a mixer, and then added with magnesium stearate to mix uniformly. Tablettingwas performed to obtain the final product.

Measurement of Compounds’ Activity

Results of enzyme inhibition activity test

[0281] The enzyme used for the enzyme inhibition activity test was obtained by suitably treating various tissues andseparating the enzyme with FPLC, according to a method similar as those reported in the literatures (Thrombosis Res.1991, 62, 31 and J. Biol. Chem. 1997, 272, 2714). More specifically, PDE5 and PDE3 were obtained from human bloodplatelet, and PDE6 was separated from bovine retina. Upon enzyme was separated out, the enzyme inhibition activitytest would be carred out immediately. The said enzyme inhibition activity test was performed by directly detecting thescintillation proximity of AMP/GMP using TRKQ7100 and TRKQ7090 kits, which was generally as follows. In the presenceof different concentrations of inhibitor and a small amount of substrate, 10ml of buffer (50mM Tris/HCl PH 7.5, 8.3mMMgCl2, 1.7mM EGTA) was added, and then water was added to a final volume of 100ml. The reaction was initiated witha fixed amount of enzyme, incubated at 30°C for 30min, and then quenched with 50ml of yttrium silicate beads comprisingzinc sulphate. After shaken for 20min, the reaction mixture was put in dark and settled for 30min, and then readed ona BECKMAN LS6500 MULTI-PURPOSE SCINTILLATION COUNTER. Finally, the 50% inhibitory ratio (IC50) for enzymeof the compound according to the present invention was calculated based on the readings.

Results of PDE5 inhibition activity test

[0282] According to the above-mentioned method, the inhibition activity for human blood platelet PDE5 of some com-pounds of formula I according to the present invention was measured, and the results are shown in the following teble:

Measured compound PDE5 IC50 (nM) Measured compound PDE5 IC50 (nM)

Sildenafil 3.94 Example 29 4.52

Example 31 1.36 Example 32 2.02

Example 43 3.72 Example 46 1.09

Example 49 1.86 Example 50 1.24

Example 51 1.23 Example 52 1.46

Example 53 0.57 Example 54 1.21

Example 55 0.92 Example 57 1.19

Example 59 0.57 Example 60 2.04

Example 61 1.93 Example 63 1.24

Example 67 1.61 Example 68 0.53

Example 76 1.99 Example 87 3.29

Example 89 1.98 Example 98 2.77

Example 102 4.61 Example 107 0.92

Example 108 0.54 Example 110 2.85

Example 114 0.83 Example 116 0.93

Example 117 0.66 Example 118 0.76

Example 119 6.31 Example 123 0.49

Example 124 0.13 Example 125 0.19

Example 126 1.79 Example 133 1.13

Example 135 1.01 Example 138 0.47

Example 139 0.61 Example 140 0.57

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[0283] According to the inhibition activity (IC50) for PDE5 of the compounds in the above table, it can be seen that thecompounds of formula I according to the present invention have a PDE 5 inhibition activity. It is more important that mostof the compounds in the above table show a stronger PDE5 inhibition activity than Sildenafil, and thus have a smalleroral dose than Sildenafil and a reduced probability of causing side effects.

Results of PDE6 inhibition activity test

[0284] Taking into account that the compounds according to the present invention can have the inhibition activity forPDE6 distributed in retina to cause visual disorder, the present inventors measured the inhibition activity for PDE6 inbovine retina of some compounds of formula I according to the present invention, and the results are shown in thefollowing table:

(continued)

Measured compound PDE5 IC50 (nM) Measured compound PDE5 IC50 (nM)

Example 145 0.47 Example 146 0.93

Example 149 1.80 Example 150 0.52

Example 151 0.54 Example 154 0.40

Example 155 0.54 Example 163 7.92

Example 164 0.46 Example 166 0.33

Example 169 0.11 Example 174 0.45

Example 179 0.23 Example 186 0.34

Example 204 0.88 Example 205 1.93

Example 208 3.69 Example 209 0.64

Example 210 6.23 Example 211 0.90

Example 212 0.79 Example 213 2.80

Example 214 1.80 Example 215 0.88

Example 216 0.83 Example 217 2.12

Example 218 8.63

Measured compound PDE6 IC50 (nM) PDE5 IC50 (nM) PDE6 IC50 / PDE5 IC50

Sildenafil 40.2 3.94 10.2

Example 29 130 4.52 28.8

Example 31 52.8 1.36 38.8

Example 32 40.6 2.02 20.1

Example 43 42.8 3.72 11.5

Example 46 642 1.09 589.0

Example 49 619.6 1.86 10.5

Example 50 114 1.24 91.9

Example 51 34.8 1.23 28.3

Example 52 52.6 1.46 36.0

Example 53 36.8 0.57 66.2

Example 54 13.2 1.21 10.9

Example 55 20.1 0.93 21.8

Example 57 8.19 1.19 6.9

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(continued)

Measured compound PDE6 IC50 (nM) PDE5 IC50 (nM) PDE6 IC50 / PDE5 IC50

Example 59 7.88 0.57 13.7

Example 60 8.19 2.04 4.0

Example 61 29.1 1.93 15.1

Example 63 33.4 1.24 26.9

Example 67 26.9 1.61 16.7

Example 68 16.4 0.53 31.0

Example 76 25.2 1.99 12.7

Example 89 11.7 1.98 5.88

Example 98 10.4 2.77 3.77

Example 102 24.6 4.61 5.33

Example 107 6.42 0.92 22.64

Example 108 5.73 0.54 6.99

Example 110 22.2 2.85 7.80

Example 114 18.7 0.83 10.53

Example 116 22.9 0.93 24.5

Example 117 10.4 0.66 15.6

Example 123 13.3 0.49 27.3

Example 124 3.76 0.13 28.6

Example 125 2.71 0.19 14.6

Example 126 54.9 1.79 30.7

Example 133 20.9 1.31 15.9

Example 135 9.66 1.01 9.6

Example 138 5.42 0.47 11.4

Example 139 7.82 0.61 12.8

Example 140 4.25 0.57 7.5

Example 145 24.2 0.47 51.5

Example 146 6.64 0.93 7.2

Example 150 2.78 0.52 5.3

Example 154 37.9 0.40 94.6

Example 163 48.6 7.92 6.1

Example 164 31.8 0.46 68.7

Example 166 5.15 0.33 15.6

Example 169 10.4 0.11 91.3

Example 174 13.7 0.45 30.3

Example 179 22.2 0.23 96

Example 186 7.4 0.34 21.4

Example 204 54.5 0.88 61.9

Example 205 17.2 1.93 8.9

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[0285] The selectivity for PDE6 and PDE5 of the compounds according to the present invention was determined asthe ratio of IC50 PDE6/IC50 PDE5 in the present invention. It can be seen from the above results that the compounds offormula I according to the present invention have an excellent PDE5 selectivity, especially, most of the compoudsobtained in the examples have a higher selectivity than Sildenafil. Accordingly, the compounds according to the presentapplication have a reduced possibility of causing visual disorder, compared with Sildenafil.

Claims

1. A compound of formula I, pharmaceutically acceptable salts or solvates thereof:

wherein,

R1 and R2 are each independently H; C1-C10 alkyl; C3-C6 alkenyl; C3-C6 cycloalkyl; halogen; CF3; OR5; NHCOR8;aryl; or C1-C4 alkyl optionally substituted with aryl or OR5; Z is OR3;R3 is C1-C6 alkyl; C3-C6 cycloalkyl; C3-C6 alkenyl; C1-C3 haloalkyl; or C1-C3 alkyl substituted with C1-C3alkoxyor C3-C6 cycloalkyl;R4 is NO2; CN; SO2NR6R7; NR9R10; COR11; OR12; C2-C4 alkyl optionally substituted with OH, CN, C1-C4 alkoxy,NR6R7, CONR6R7 or CO2R8; C2-C4 alkenyl optionally substituted with CN, CONR6R7 or CO2R8; or R4 is a 5~7-member heterocyclyl optionally substituted with one or more substituents selected from OH, COOR8, CONH2,C1-C6 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, aryl, Het, and C1-C6 alkyl substituted with halogen or alkoxy orhydroxyl; or R4 is a 5- or 6-member monosaccharide group optionally substituted with one or more substituentsselected from C1-C6 alkyl, trimethylsilyl, benzyl and acetyl;R5 is H; C1-C6 alkyl; C3-C6 alkenyl; C3-C6 cycloalkyl; C1-C4 alkyl optionally substituted with OH, C1-C4 alkoxyor NR6R7; aryl; or Het;R6 and R7 are each independently H, OH, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 alkenyl, C3-C6 cycloalkyl, adamantyl,C3-C8 lactamyl, aryl, Het, or (CH2CH2O)jH wherein j is 1~3; or R6 and R7 are each independently C1-C6 alkyloptionally substituted with OH, C1-C4 alkoxy, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, NR13R14,aryl, Het or 4~8-member heterocyclyl; or R6 and R7 are each independently a 4~8-member heterocyclyl optionallysubstituted with one or more substituents selected from OH, COOR8, CONH2, COR16, SO2R16, C1-C6 alkyl,C1-C4 alkoxy, C3-C6 cycloalkyl, aryl, Het and C1-C6 alkyl substituted with halogen or C1-C4 alkoxy or hydroxyl;or R6 and R7, together with the nitrogen atom to which they are attached, form a 4~8-member heterocyclyloptionally substituted with one or more substituents selected from OH, COOR8, CONH2, COR16, SO2R16, C1-C6alkyl, (CH2CH2O)jH wherein j is 1~3, C1-C4 alkoxy, C3-C6cycloalkyl, aryl, Het, and C1-C6 alkyl substituted withhalogen or C1-C4 alkoxy or hydroxyl or aryl; or R6 and R7, together with the nitrogen atom to which they areattached, form glucosylamino group, amino-acid residue, amino-acid ester residue or aminoamide residue,which are optionally substituted with one or more substituents selected from C1-C6 alkyl, NR13R14, COR16,benzyl, benzyloxycarbonyl and t-butyloxycarbonyl;R8 is H, C1-C6 alkyl or aryl;R9 is H, C1-C6 alkyl or SO2R16;R10 is H; C1-C6 alkyl; COR15; SO2NR6R7; SO2R16;

a 5- or 6-member monosaccharide group optionally substituted with one or more substituents selected fromC1-C6 alkyl, trimethylsilyl, benzyl and acetyl; or, R10 is a 5-member heterocyclyl optionally substituted with oneor more substituents; or, when R9 is H, R10 is an amino-acid residue optionally substituted with one or more

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substituents selected from OH, C1-C6 alkyl, C1-C4 alkoxy, COR16, benzyl, benzyloxycarbonyl and t-butyloxy-carbonyl;R11 is H; OH; C1-C6 alkyl; aryl; Het; NH(CH2)kNH2, NH(CH2)kNHSO2R16, or NH(CH2)kNHCOR16, wherein k is0~4; C1-C3 alkyl substituted with halogen, OH or C1-C6 alkoxy; or (CH2)mNR6R7, wherein m is 0~2; or, R11 isan amino-acid residue or an aminoamide residue optionally substituted with C1-C6 alkyl or C1-C4 alkoxy;R12 is H, COR19, SO2R16, or a 5- or 6-member monosaccharide group optionally substituted with one or moresubstituents selected from C1-C6 alkyl, trimethylsilyl, benzyl and COR16;R13 and R14 are each independently H or C1-C6 alkyl; or, R13 and R14, together with the nitrogen atom to whichthey are attached, form a 4~8-member heterocyclyl optionally substituted with one or more substituents selectedfrom OH, C1-C6 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, aryl and Het;R15 is H; CF3; C1-C6 alkyl optionally substituted with halogen, OH, C1-C6 alkoxycarbonylamino, NR13R14,NHSO2R16, NHCOR16 SO3H, SO2NR13R14, SO2R16 PO(OH)2, PO(OR16)2, aryl or Het; (CH2)nCOOR8, or(CH2)nCONHR8, wherein n is 0~6; C2-C4 alkenyl optionally substituted with C1-C6 alkyl, OH, C1-C6 alkoxy orNR13R14; C3-C6 cycloalkyl optionally substituted with C1-C6 alkyl, or OH; C3-C6 cycloalkoxy optionally substitutedwith C1-C6 alkyl or OH; aryl; or Het;R16 is C1-C6 alkyl, aryl or Het;R17 and R18 are each independently H; C1-C6 alkyl optionally substituted with OH, SO3H, SO2NR13R14, SO2R16,PO(OH)2, PO(OR16)2, NR13R14, aryl, Het or 4~8-member heterocyclyl; C3-C6 cycloalkyl; or aryl optionally sub-stituted with OH; or, R17 and R18, together with the nitrogen atom to which they are attached, form a 4~8-member heterocyclyl optionally substituted with one or more substituents selected from OH, C1-C6 alkyl, C1-C4alkoxy, C3-C6 cycloalkyl, aryl and Het;R19 is C1-C6 alkyl, aryl or NHR8;R20 is C1-C3 alkyl;halogen is F, Cl, Br or I;Y is O, S or NR8;the said ’aryl’ is phenyl unsubstituted or substituted with one or more substituents selected from halogen, C1-C3alkyl, C1-C3 alkoxy, CF3, CN and NO2;the said ’5~7-ember heterocyclyl’, ’4~8-member heterocyclyl’ and ’5-member heterocyclyl’ denote saturated orunsaturated heterocyclyl comprising one or more heteroatoms selected from N, S and O;the said ’Het’ is a 5~6-member aromatic heterocyclyl comprising 1~4 heteroatoms selected from N, S and O,the said 5~6-member aromatic heterocyclyl being optionally sutstituted with one or more substituents selectedfrom halogen, C1-C3 alkyl, C1-C3 alkoxy, CF3, CN and NO2.

2. The compound of formula I, the pharmaceutically acceptable salts or solvates thereof according to claim 1, wherein,R1 and R2 are each independently H; C1-C10 alkyl; halogen; CF3; OR5; NHCOR8; aryl; or C1-C4 alkyl optionallysubstituted with aryl or OR5;Z is OR3;R3 is C1-C6 alkyl or C1-C3 alkyl substituted with C1-C3 alkoxy;R4 is NO2; CN; SO2NR6R7; NR9R10; COR11; OR12; C2-C4 alkyl optionally substituted with OH, C1-C4 alkoxy orNR6R7; or, R4 is a 5- or 6-member heterocyclyl optionally substituted with one or more substituents selected fromOH, COOR8, CONH2, C1-C6 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, aryl, Het and C1-C6 alkyl substituted with OH;or, R4 is a 5- or 6-member monosaccharide group optionally substituted with one or more substituents selected fromC1-C6 alkyl, trimethylsilyl, benzyl and acetyl;R5 is H; C1-C6 alkyl; C1-C4 alkyl optionally substituted with OH, C1-C4 alkoxy or NR6R7; or aryl;R6 and R7 are each independently H, OH, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 alkenyl, C3-C6 cycloalkyl, adamantyl,C3-C8 lactamyl, aryl, Het, or (CH2CH2O)jH wherein j is 1~3; or R6 and R7 are each independently C1-C6 alkyloptionally substituted with OH, C1-C4 alkoxy, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, NR13R14, aryl,Het or 4~8-member heterocyclyl; or R6 and R7 are each independently a 4~8-member heterocyclyl, wherein thesaid 4~8-member heterocyclyl is furyl, thienyl, thiazolyl, imidazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyrazinyl, mor-pholinyl, thiomorpholinyl, piperidyl, pyrrolidinyl or piperazinyl, and the said 4~8-member heterocyclyl is optionallysubstituted with one or more substituents selected from OH, COOR8, CONH2, COR16, SO2R16, C1-C6 alkyl, C3-C6cycloalkyl, aryl, Het and C1-C6 alkyl substituted with C1-C4 alkoxy or hydroxyl; or R6 and R7, together with thenitrogen atom to which they are attached, form a 4~8-member heterocyclyl optionally substituted with one or moresubstituents selected from OH, COOR8, CONH2, COR16, SO2R16, C1-C6 alkyl, (CH2CH2O)jH wherein j is 1~3, C3-C6cycloalkyl, aryl, Het, and C1-C6 alkyl substituted with C1-C4 alkoxy or hydroxyl or aryl; or R6 and R7, together withthe nitrogen atom to which they are attached, form glucosylamino group, amino-acid residue, amino-acid esterresidue or aminoamide residue, which are optionally substituted with one or more substituents selected from C1-C6alkyl, NR13R14, COR16, benzyl, benzyloxycarbonyl and t-butyloxycarbonyl;

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R8 is H, C1-C6 alkyl or aryl;R9 is H, C1-C6 alkyl or SO2R16;R10 is H; C1-C6 alkyl; COR15; SO2R16;

a 5- or 6-member monosaccharide group; or R10 is dihydroimidazolyl substituted with hydroxyalkyl, or 1,2,4-triazolyloptionally substituted with C1-C6 alkyl, aryl or amino group; or when R9 is H, R10 is an amino-acid residue optionallysubstituted with one or more substituents selected from OH, C1-C6 alkyl, C1-C4 alkoxy, COR16, benzyl, benzyloxy-carbonyl and t-butyloxycarbonyl;R11 is H; OH; C1-C6, alkyl; aryl; Het; NH(CH2)kNH2, NH(CH2)kNHSO2R16, or NH(CH2)kNHCOR16, wherein k is 0~4;C1-C3 alkyl substituted with halogen, OH or C1-C6 alkoxy; or (CH2)mNR6R7, wherein m is 0~2; or, R11 is an amino-acid residue or an aminoamide residue, which are optionally substituted with C1-C4 alkoxy;R12 is H, COR19, SO2R16 or a 5-or 6-member monosaccharide group;R13 and R14 are each independently H or C1-C6 alkyl; or, R13 and R14, together with the nitrogen atom to whichthey are attached, form a 4~8-member heterocyclyl optionally substituted with one or more substituents selectedfrom OH and C1-C6 alkyl;R15 is H; CF3; C1-C6 alkyl optionally substituted with halogen, OH, C1-C6 alkoxycarbonylamino, NR13R14, NHSO2R16,NHCOR16, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, aryl or Het; (CH2)nCOOR8, or (CH2)nCONHR3,wherein n is 0~6; C2-C4 alkenyl optionally substituted with C1-C6 alkyl, OH, C1-C6 alkoxy or NR13R14; C3-C6 cycloalkyloptionally substituted with C1-C6 alkyl or OH; C3-C6 cycloalkoxy optionally substituted with C1-C6 alkyl or OH; aryl;or Het;R16 is C1-C6 alkyl or aryl;R17 and R18 are each independently H; C1-C6 alkyl optionally substituted with OH, SO3H, SO2NR13R14, SO2R16,PO(OH)2, PO(OR16)2, NR13R14, aryl, Het or 4~8-member heterocyclyl; C3-C6 cycloalkyl; or aryl optionally substitutedwith OH; or, R17 and R18, together with the nitrogen atom to which they are attached, form a 4~8-member heterocyclyloptionally substituted with one or more substituents selected from OH and C1-C6 alkyl;R19 is C1-C6 alkyl, aryl or NHR8;R20 is C1-C3 alkyl;halogen is F, Cl, Br or I;Y is O, S or NR8;the said ’aryl’ is phenyl unsubstituted or substituted with one or more substituents selected from halogen, C1-C3alkyl, and C1-C3 alkoxy;the said ’5- or 6-member heterocyclyl’, ’4~8-member heterocyclyl’, ’5-member heterocyclyl" denote saturated orunsaturated heterocyclyl comprising one or more heteroatoms selected from N, S and O;the said ‘Het’ is a 5~6-member aromatic heterocyclyl comprising 1~4 heteroatoms selected from N, S and O, thesaid 5~6-member aromatic heterocyclyl being optionally sutstituted with one or more substituents selected fromhalogen, C1-C3 alkyl, C1-C3 alkoxy, CF3, CN and NO2;the said ’amino-acid’ is glycine, alanine, phenylalanine, serine, tryptophane, valine, leucine, isoleucine, t-leucine,tyrosine, lysine, histidine, methionine, arginine, threonine, aspartate, cysteine, proline, glutamic acid, asparagine,glutamine, ornithine or citrulline;the said ’5- or 6-member monosaccharide’ is ribose, deoxyribose, xylose, arabinose, glucose, mannose, galactoseor fructose.

3. A compound of formula I, the pharmaceutically acceptable salts or solvates thereof,

wherein,

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R1 is H, F, Cl, Br, I, OH, methyl, ethyl, propyl, isopropyl or acetamido;R2 is Br, CF3, OR5, ethyl, propyl, isopropyl, benzylamino, phenyl, benzyl, isobutyl, n-octyl or acetamido;Z is OR3;R3 is ethyl, propyl, n-butyl, n-hexyl or 3-methoxylpropyl;R4 is NO2, SO2NR6R7, NR9R10, COR11, OR12 or glucosyl; or R4 is a 5- or 6-member heterocyclyl, wherein thesaid 5- or 6-member heterocyclyl is thienyl, thiazolyl, 1,2,4-triazolyl, imidazolyl, pyrrolyl, oxadiazolyl, pyrimidinyl,morpholinyl, thiomorpholinyl, piperidyl, pyrrolidinyl or piperazinyl, and the said 5- or 6-member heterocyclyl isoptionally substituted with one or more substituents selected from OH, COOH, CONH2, C1-C6 alkyl, C1-C4alkoxy, C3-C6 cycloalkyl, aryl, Het and C1-C6 alkyl substituted with OH;R5 is H; C1-C4 alkyl optionally substituted with OH, C1-C4 alkoxy or NR6R7; or aryl;R6 and R7 are each independently H, methyl, methoxyl, cyclopropyl, propenyl, isobutyl, t-butyl, adamantyl,cyclohexyl, caprolactamyl, 2-(1-methylpyrrol-2-yl)ethylamino, pyridylmethyl, thienylmethyl,

or C2-C3 alkyl optionally substituted with OH, NR13R14, SO3H, SO2NR13R14 or 5~6-member heterocyclyl, where-in the said 5~6-member heterocyclyl is morpholinyl, thiomorpholinyl, piperidyl, pyrrolidinyl or piperazinyl, andthe said 5~6-member heterocyclyl is optionally substituted with one or more substituents selected from OH,COOR8, CONH2, COR16, SO2R16, C1-C6 alkyl and aryl; or R6 and R7, together with the nitrogen atom to whichthey are attached, form a 5~6-member heterocyclyl, wherein the said 5~6-member heterocyclyl is morpholinyl,thiomorpholinyl, piperidyl, pyrrolidinyl or piperazinyl, and the said 5~6-member heterocyclyl is optionally sub-stituted with one or more substituents selected from OH, COOR", CONH2, COR16, SO2R16, C1-C6 alkyl,(CH2CH2O)jH wherein j is 1~2, dichlorophenyl, benzyl, pyridyl and aryl; or NR6R7 is glucosylamino group, amino-acid residue, amino-acid ester residue or amino-amide residue, which are optionally substituted with one ormore substituents selected from NR13R14 and acetyl;R8 is H, methyl or ethyl;R9 is H, methyl or SO2R16;R10 is H, methyl, COR15, SO2R16,

glucosyl or mannosyl; dihydroimidazolyl substituted with hydroxyethyl; or when R9 is H, R10 is an amino-acidresidue optionally substituted with one or more selected from OH, t-butyloxycarbonyl, and acetyl;R11 is OH; pyrazolyl substituted with isopropyl; aminoamide residue; amino-ester residue; NR6R7; CH2Br orCH2NR6R7;R12 is H, COR19, SO2R16, mannosyl or glucosyl;R13 and R14 are each independently H or ethyl; or, R13 and R14, together with the nitrogen atom to which theyare attached, form a 5~6-member heterocyclyl, wherein the said 5~6-member heterocyclyl is morpholinyl, pip-eridyl, pyrrolidinyl or piperazinyl, and the said 5~6-member heterocyclyl is optionally substituted with one ormore substituents selected from OH and C1-C6 alkyl;R15 is H; methyl; ethyl; cyclohexyl; CF3; (CH2)nCOOR8, or (CH2)nCONH2, wherein, n is 0 or 1; vinyl; propenyl;pyridyl; phenyl substituted with ethoxy; or thiazolyl substituted with isopropyl;R16 is methyl;R17 and R18 are each independently H, ethyl or phenyl; or R17 and R18, together with the nitrogen atom to whichthey are attached, form a 4~8-member heterocyclyl, wherein the said 4~8-member heterocyclyl is morpholinyl,piperidyl, pyrrolidinyl or piperazinyl, and the said 4~8-member heterocyclyl is optionally substituted with one ormore substituents selected from OH and C1-C6 alkyl; or when Y is NH, R17 and C(Y)N form a dihydroimidazolyl;R19 is methyl or NHC2H5;R20 is methyl;halogen is F, Cl, Br or I;Y is O, S, NH or NC2H5;the said ’aryl’ is phenyl unsubstituted or substituted with one or more substituents selected from halogen, C1-C3

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alkyl, and C1-C3 alkoxy;the said ’Het’ is a 5~6-member aromatic heterocyclyl comprising 1~4 heteroatoms selected from N, S and O,the said 5~6-member aromatic heterocyclyl being optionally sutstituted with one or more substituents selectedfrom halogen, C1-C3 alkyl, C1-C3 alkoxy, CF3, CN and NO2;the said ’amino-acid’ is glycine, alanine, phenylalanine, serine, tryptophane, valine, leucine, isoleucine, t-leucine,tyrosine, lysine, histidine, methionine, arginine, threonine, aspartate, cysteine, proline, glutamic acid, asparag-ine, glutamine, ornithine or citrulline;the said ’5- or 6-member monosaccharide’ is glucose or mannose.

4. The compound of formula I, the pharmaceutically acceptable salts or solvates thereof according to claim 1, wherein,the said phenylpyrimidone compound is selected from:

6-isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,6-acetamido-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-chloro-6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-acetamido-6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-[2-n-butoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-bromo-6-n-octyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)- one,5-bromo-6-phenyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)- one,5-methyl-6-isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-fluoro-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one, 5-methyl-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-hydroxy-6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-[2-n-hexyloxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-bromo-6-isobutyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-{2-n-propoxyl-5-[N-methyl-N-(2-hydroxyethyl)aminosulfonyl]phenyl}pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-{2-n-propoxyl-5-[N-(2-morpholinoethyl)aminosulfonyl]phenyl}pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-{2-n-propoxyl-5-[N-(3-morpholinopropyl)aminosulfonyl]phenyl}pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-{2-n-propoxyl-5-[N-(N’,N’-diethylamino)ethylaminosulfonyl]phenyl}pyrimid-4(3H)-one,5,6-diethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5,6-diethyl-2-{2-n-propoxyl-5-[N-methyl-N-(hydroxyethyl)aminosulfonyl]phenyl}pyrimid-4(3H)-one,5,6-diethyl-2-{2-n-propoxyl-5-[N-(2-ethylaminoethyl)aminosulfonyl)phenyl}pyrimid-4(3H)-one,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylsulfonylproline,2-(5-nitro-2-n-propoxyphenyl)-5-bromo-6-isopropylpyrimid-4(3H)-one,2-(5-amino-2-n-propoxyphenyl)-5-bromo-6-isopropylpyrimid-4(3H)-one,1-(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylthiourea,1-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-3-ethyl-2-methylisothiourea,N-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’,N"-triethylguanidine,N-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-piperidyl-1-formami-dine,N-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-pyrrolyl-1-formami-dine,2-{2-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]amino-4,5-dihydro-imida-zol-1-yl}-ethanol,2-(5-nitro-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one,2-(5-amino-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylthiourea,1-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-3-ethyl-2-methylisothiourea,N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-piperidyl-1-formamidine,N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’,N"-triethylguanidine,2-{2-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]amino-4,5-dihydro-imidazol-1-yl}-eth-anol,N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-pyrrolyl-1-formamide,N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-pyrrolyl-1-formamidine,

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5-bromo-6-isopropyl-2-(2-n-propoxyl-5-mesylamidophenyl)pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-mesylamidophenyl)pyrimid-4(3H)-one,N-(3-(1,6-dihydro-4-isopropyl-5-bromo-6-oxopyrimidin-2-yl)-4-propoxyphenyl)acetamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)acetamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)propionamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)cyclohexamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)formamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)-1-t-butyloxycarbonyl-4-hydroxy-prolyla-mide,4-n-propoxyl-3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)benzoic acid,(morpholin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,(piperid-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,(2-aminoformylpyrrol-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,4-n-propoxyl-3-(1,6-dihydro-4-isopropyl-6-oxopyrimidin-2-yl)benzoic acid,(morpholin-1-yl)(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,(piperid-1-yl)(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,(4-methyl-piperazin-1-yl)(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophe-none,2-(5-(N,N-dimethylamino-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylurea,1-(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-phenylthiourea,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-guanidine,5-bromo-6-isopropyl-2-(5-(2-bromoacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-(5-(2-morpholinylacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-(5-(2-(4-methyl-piperazin-1-yl)acetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,5,6-diethyl-2-(5-(2-bromoacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,5,6-diethyl-2-(5-(2-(4-methyl-piperazin-1-yl)acetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,5,6-diethyl-2-(5-(2-morpholinylacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-(2-n-propoxyl-5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-ylami-no)phenyl)pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-(2-n-propoxyl-5-(tetrahydro-3,4-dihydroxy-5-(1,2-dihydroxyethyl)fur-2-ylamino)phe-nyl)pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(tetrahydro-3,4-dihydroxy-5-(1,2-dihydroxyethyl)fur-2-ylamino)phenyl)pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-ylamino)phenyl)py-rimid-4(3H)-one,2-(5-hydroxy-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one,(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl) acetate,(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl) ethylaminoformate,5,6-diethyl-2-(2-n-propoxyl-5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yloxy)phenyl)pyrim-id-4(3H)-one,(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl) mesylate,2-(5-(2,5-dimethyl-1H-pyrrol-1-yl)-2-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one,2,2’-(4-n-propoxyl-1,3-phenylene)bis(5,6-diethylpyrimid-4(3H)-one),2-(5-(1,3,4-oxadiazol-2-yl)-2-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-one,ethyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)acetate,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-morpholinylethyl)-4-n-propoxybenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N,N-di(2-hydroxyethyl)-4-n-propoxybenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-caprolactam-3-yl)-4-n-propoxybenzamide,(4-(2,3-dichlorophenyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophe-none,(3-isopropylpyrazol-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,N-cyclohexyl-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,N-((pyrid-2-yl)methyl)-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3,3-dimethylbutyrate,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2,2,2-trifluoroacetamide,ethyl N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformylformate,

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N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)acrylamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-crotonamide,ethyl N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformylacetate,2-ethoxyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)benzamide,N-(3-(4,5-diethyf-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)nicotinamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-5-isopropylthiazolyl-2-formamide,t-butyl 3-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformyl)propylaminofor-mate,4-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)butyramide ,1-acetyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)pyrrolidinyl-2-formamide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-methylbutyramide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-phenylpropionamide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)propionamide,2,6-diacetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)hexanamide,N1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)propanediamide,N1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)oxalamide,N-(aminoformylmethyl)-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,5,6-diethyl-2-{2-n-propoxyl-5-[(2-(1-methylpyrrol-2-yl)ethyl)aminosulfonyl]phenyl}pyrimid-4(3H)-one,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-(1-methylpyrrol-2-yl)ethyl)-4-n-propoxylbenzamide,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5-ureapentanoic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5-aminopentanoic ac-id,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-methylbutyric acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropanoic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-hydroxypropanoicacid,ethyl 2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropionate,3-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropylsulfonic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminoethylsulfonic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-aminoformylpropa-noic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-indolepropionic ac-id,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminoacetic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3,3-dimethylbutyricacid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-4-aminoformylbutyricacid,ethyl 2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-methylvaler-ate,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylsulfonamido)-6-acetamidoc-aproate,5,6-diethyl-2-(2-n-propoxyl-5-(4-hydroxyethyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(3-hydroxypropylaminosulfonyl)phenyl]pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(N-(2-morpholinylethyl)-N-(2-hydroxyethyl)aminosulfonyl)phenyl)pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(N-methyl-N-(2-(pyrrolidin-1-yl)ethyl)aminosulfonyl)phenyl)pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(2-(N,N-diethyl)aminoethylaminosulfonyl)phenyl]pyrimid-4(3H)-one maleate,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phenylpropanoic acid,methyl N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzoylprolinate,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-(4-hydroxyphenyl)propi-onate,ethyl 2-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-(1H-indol-3-yl)propionate,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-methylbutyrate,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-(1H-imidazol-4-yl)propi-onate,ethyl 2-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-methylvalerate,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)propionic acid,

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2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-aminoformylpropionic acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-4-aminoformylbutyric acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-hydroxypropionic acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-guanidinopentanoic acid,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phenylpropionate,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propionate,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-4-methylvalerate,ethyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido) propionate,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-(4-methylpiperazin-1-yl)-1-oxopropan-2-yl)-4-n-propoxy-benzamide,N-(1-aminoformylethyl)-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl-N-(2-(thien-2-yl)ethyl)benzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl-N-((fur-2-yl)methyl)benzamide,N-t-butyl-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-isobutyl-4-n-propoxylbenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-allyl-4-n-propoxylbenzamide,(4-(pyrid-2-yl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophenone,(4-(hydroxyethyloxylethyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzo-phenone,(4-(hydroxyethyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophenone,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(3-hydroxypropyl)-4-n-propoxylbenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-hydroxy-2-propyl)-4-n-propoxybenzamide,N-ethyl-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-hydroxyethyl)-4-n-propoxylbenzamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-diethylaminoethyl)-4-n-propoxylbenzamide,3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propyl-1-sulfonic acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)ethylsulfonic acid,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-hydroxyethyl)-N-methyl-4-n-propoxylbenzamide,(4-benzylpiperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophenone,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-methyl-N-(2-(pyrrolidin-1-yl)ethyl)-4-n-propoxybenzamide,methyl 5-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)piperidyl-2-formate,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-methoxyl-N-methyl-4-n-propoxybenzamide,5,6-diethyl-2-[2-(3-methoxyln-propoxyl)-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,2-chloro-N-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)acetamide,2-(dimethylamino)-N-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)acetamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-(4-methylpiperazin-1-yl)acetamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-morpholinyl)acetamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-(piperid-1-yl)acetamide,dimethyl (3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylaminoformyl)methylphosphate,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)isobutyramide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-methylbutyramide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-phenylacetamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)benzamide,ethyl 3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylaminoformyl) propionate,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-5-oxopyrrolidinyl-2-formamide,2-acetamido-N-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-4-methylpentanamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-acetamido-3-(1H-indol-3-yl)propiona-mide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)glutaramide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-hydroxybutyramide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-hydroxypropionamide,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylaminoformyl)-2-acetamidoethyl acetate,5,6-diethyl-2-(5-(ethylamino)-2-n-propoxyphenyl)pyrimid-4(3H)-one,N-ethyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)propionamide,ethyl (N-ethyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformylformate,1, 3-diethyl-1-(3-(4, 5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)piperidyl-1-formamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-4-methylpiperazinyl-1-formamide,

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1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-propylurea,1-cyclohexyl-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea,1,1-diethyl-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea,1-(2-(diethylamino)ethyl)-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea maleate,(4-methylpiperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophenone,5-iodo-6-isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-chloro-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-((tetrahydro-2,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-3-ylamino)sulfo-nyl)phenyl]pyrimid-4(3H)-one,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-ureapentanoic acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-aminopentanoic acid,3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(tetrahydro-2,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-3-yl)-4-n-propoxybenzamide,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)ethylsulfamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-methyl-piperazin-1-ylsulfonylethyl)-4-n-propoxybenza-mide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylethyl)-4-n-propoxybenzamide,3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propylsulfamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-methyl-piperazin-1-ylsulfonylpropyl)-4-n-propoxybenza-mide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylpropyl)-4-n-propoxybenzamide,5,6-diethyl-2-(5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,5-iodo-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5-bromo-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one, and5-chloro-6-isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one.

5. The compound of formula I, the pharmaceutically acceptable salts or solvates thereof according to any one of claims1∼3, wherein, the said phenylpyrimidone compound is selected from:

5,6-diethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one, 5,6-diethyl-2-{2-n-pro-poxyl-5-[N-(2-morpholinylethyl)aminosulfonyl)phenyl}pyrimid-4(3H)-one,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylsulfonylproline,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylthiourea,N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’,N"-triethyl guanidine,N-[3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-pyrrolyl-1-formamide,5-bromo-6-isopropyl-2-(2-n-propoxyl-5-mesylamidophenyl)pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-mesylamidophenyl)pyrimid-4(3H)-one,N-(3-(1,6-dihydro-4-isopropyl-5-bromo-6-oxopyrimidin-2-yl)-4-propoxyphenyl)acetamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)acetamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)propionamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)cyclohexamide,N-(3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)-1-t-butyloxycarbonyl-4-hydroxy-prolyla-mide,(morpholin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,(piperid-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,(2-aminoformylpyrrol-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,(morpholin-1-yl)(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenone,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea,1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylurea,5;6-diethyl-2-(5-(2-morpholinylacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one,2,2’-(4-n-propoxyl-1,3-phenylenyl)bis(5,6-diethylpyrimid-4(3H)-one),ethyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)acetate,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2,2,2-trifluoroacetamide,ethyl N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformylacetate,4-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)butyramide,1-acetyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)pyrrolidinyl-2-formamide,2-acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-phenylpropionamide,

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N1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)oxalamide,5,6-diethyl-2-{2-n-propoxyl-5-[(2-(1-methylpyrrol-2-yl)ethyl)aminosulfonyl]phenyl}pyrimid-4(3H)-one,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-(1-methylpyrrol-2-yl)ethyl)-4-n-propoxylbenzamide,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5-ureapentanoic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5-aminopentanoic ac-id,ethyl 2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amiriopropionate,3-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropylsulfonic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminoethylsulfonic acid,2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-aminoformylpropa-noic acid,5,6-diethyl-2-(2-n-propoxyl-5-(4-hydroxyethyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one,5,6-diethyl-2-(2-n-propoxyl-5-(N-(2-morpholinylethyl)-N-(2-hydroxyethyl)aminosulfonyl)phenyl)pyrimid-4(3H)-one,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phenylpropanoic acid,methyl N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzoylprolinate,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-(4-hydroxyphenyl)propi-onate,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)propanoic acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-aminoformylpropanoic acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-guanidinopentanoic acid,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phenylpropanoic acid,methyl 2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propanoic acid,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-(4-methylpiperazin-1-yl)-1-oxopropan-2-yl)-4-n-propoxy-benzamide,N-(1-aminoformylethyl)-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,(4-(hydroxyethyoxylethyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzo-phenone,(4-(hydroxyethyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophenone,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-hydroxy-2-propyl)-4-n-propoxybenzamide,3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propyl-1-sulfonic acid,methyl 5-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)piperidinyl-2-formate,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-(4-methylpiperazin-1-yl)acetamide,N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)benzamide,1-(2-(diethylamino)ethyl)-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)urea maleate,(4-methylpiperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophenone,5,6-diethyl-2-(2-n-propoxyl-5-((tetrahydro-2,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran -3-ylamino)sulfo-nyl)phenyl]pyrimid-4(3H)-one,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-ureapentanoic acid,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-aminopentanoic acid,3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(tetrahydro-2,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-3-yl)-4-n-propoxybenzamide,2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)ethylsulfamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-methyl-piperazin-1-ylsulfonylethyl)-4-n-propoxybenza-mide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylethyl)-4-n-propoxybenzamide,3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propylsulfamide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-methyl-piperazin-1-ylsulfonylpropyl)-4-n-propoxybenza-mide,3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylpropyl)-4-n-propoxybenzamide,and5,6-diethyl-2-(5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yl)-2-n-propoxyphenyl)pyrimid-4(3H)-one.

6. A process of preparing the compound of formula I, pharmaceutically acceptable salts or solvates thereof accordingto claim 1, wherein, the process is any one of the following methods:

(1) when R4 is OH, SO2NR6R7, COR11, unsubstituted or substituted C2-C4 alkyl, unsubstituted or substituted

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C2-C4 alkenyl, or, unsubstituted or substituted 5~7-member heterocyclyl, the compound of formula I is preparedby cyclizing the compound of formula II with the compound of formula III in the presence of a base, wherein R1,R2, R3, R6, R7, R11 and the said 5~7-member heterocyclyl are defined the same as those in claim 1;

or,(2) the compound of formula I is prepared from the compound of formula la, the compound of formula le or othercompounds of formula I, wherein R1, R2, R3, R5, R6, R7, R8, R9, R10 R12 , R15 , R16, R17, R18, R19 and R20 aredefined the same as those in claim 1; wherein,

1) when R4 is SO2NR6R7, the compound of formula lb is prepared from the compound of formula la throughchlorosulfonating followed by reacting with R6R7NH in the presence of a base;

or,2) when R4 is NO2, the compound of formula Ic is prepared by nitrating the compound of formula Ia;

or,3) when R4 is NH2, the compound of formula Id is prepared by reducing the compound of formula Ic

or,4) when R4 is CN, the compound of formula If is prepared from the compound of formula Ie by nucleophilicsubstitution with cyanide;

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or,5) when R4 is COOH, the compound of formula Ig is prepared from the compound of formula If by hydrolysis;

or,6) when R4 is NR9R10, the compound of formula I is prepared from the compound of formula Id whereinR4 is NH2, wherein,

1> when R9 and R10 are simultaneouly methyl, the compound of formula I is prepared through N-methylation by using a methylating agent;2> when R9 is H and R10 is SO2R16, the compound of formula I is prepared from the compound offomula Id through sulfonylation in the presence of a base;3> when R9 is H and R10 is COR15, the compound of formula I is prepared by reacting the compoundof fomula Id with an acyl chloride derivative of an organic acid, which is obtained by reacting the organicacid with oxalyl chloride or thionyl chloride; or by condensing the compound of fomula Id with an organicacid;4> when R9 is H, R10 is C(Y)NR17R18, and Y is O or S, the compound of formula I is prepared by theaddition reaction of the compound of fomula Id with the compound of formula Y=C=NR17R18;5> when R9 is H, R10 is a 5- or 6-member monosaccharide group, the compound of formula I is preparedby reacting the compound of fomula Id with a 5- or 6-member monosaccharide having no protectinggroup in the presence of a trace amount of an organic acid as a catalyst;

6> when R9 is H, R10 is and Y is NR8, the compound of formula I is prepared by

nucleophilic substitution from the compound of fomula Ih with a compound of formula R17NHR18,wherein the compound of formula Ih is prepared by the addition reaction of the compound of fomula Iiwith iodomethane, and the compound of formula Ii is prepared by the addition reaction of the compoundof fomula Id with R8SCN;

7> when R9 is H and R10 is an amino-acid residue substituted with acetyl, condensing the compoundof fomula Id with a N-Boc protected amino-acid in the presence of a coupling agent and an activatorto give an intermediate, followed by deprotecting Boc group in trifluoroacetic acid, and finally reacting

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with acetic anhydride in pyridine to give the compound of formula I;

or,7) when R4 is COR11 and R11 is NR6R7, the compound of formula I is prepared by condensing the compoundof fomula Ig with R6R7NH; or by transforming the compound of fomula Ig into an corresponding acyl chloridederivative, followed by reacting with R6R7NH;or,8) when R4 is COR11 and R11 is CH2NR6R7, the compound of formula I is prepared by condensing thecompound of fomula Ij with R6R7NH, wherein the compound of fomula Ij is prepared by bromizing thecompound of fomula Ik, and the compound of fomula Ik is prepared by reacting the compound of fomulaIa with vinyl n-butyl ether in the presence of an metal catalyst, followed by hydrolysis; or the compound offomula Ij can also be prepared by Friedel-Crafts reaction of the compound of fomula Ia with bromoacetylbromide;

or,9) when R4 is OR12, the compound of formula I is prepared from the compound of fomula II, wherein,

1> when R12 is COR19 and R19 is C1-C6 alkyl or aryl, the compound of formula I is prepared by esterifingthe compound of fomula II wherein R4 is OH;2> when R12 is COR19 and R19 is NHR8, the compound of formula I is prepared by addition reactionof R8NCO with the compound of fomula II wherein R4 is OH;3> when R12 is SO2R16, the compound of formula I is prepared by sulfonylation of the compound offomula II wherein R4 is OH;4> when R12 is a 5- or 6-member monosaccharide group, the compound of formula In is prepared byfirstly condensing the compound of fomula II with a hydroxyl-protected 5- or 6-member monosaccharideactivated with trichloroacetonitrile to give the compound of formula Im, followed by hydrolysis anddeprotection;

or,

10) when R4 is pyrrolyl, the compound of formula Io is prepared by condensing 2,5-hexanedione with thecompound of formula Id where R4 is NH2;

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or,11) when R4 is a glycoside, the compound of formula I is prepared by firstly reacting the compound offormula Ie where R4 is Br with n-BuLi, then reacting with a protected glucolactone, followed by reducing byusing a reducing agent; or,

(3) the compound of formula I is prepared by converting other compounds of formula I where R1 is a differentsubstituent, wherein R2, R3 and R4 are defined the same as claim 1; wherein,

1) when R1 is a halogen, the compound of formula Iq is prepared by halogenating the compound of formulaIp where R1 is H in the presence of an organic base;

or,2) when R1 is NH2, the compound of formula Is is prepared by hydrolyzing the compound of formula Irwherein R1 is acetamido

7. A process for preparing the intermediate in the process according to claim 6 having the formula below

wherein, Z is OR3, and R3 and R4 are defined the same as those in claim 6,wherein the process comprise the following steps:

the compound of formula III is prepared by reacting the compound of formula IV with lithium bis(trimethylsi-lyl)amide in tetrahydrofuran;

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or;the compound of formula III is prepared by firstly reacting the compound of formula IV with hydroxylaminehydrochloride to give the compound of formula V, followed by hydrogenation;

8. A pharmaceutical composition comprising of an therapeutically effective dose of one or more selected from thegroup consisting of the compounds of formula I, the pharmaceutically acceptable salts and solvates thereof accordingto any one of claims 1∼5, and one or more pharmaceutically acceptable auxiliaries.

9. The pharmaceutical composition according to claim 8, wherein, the dose of the said compound of formula I, thepharmaceutically acceptable salts or solvates thereof is 1∼500mg per day.

10. A compound of formula I, pharmaceutically acceptable salts or solvates thereof according to any one of claims 1∼5for use in preparing a human drug.

11. A compound of formula I, pharmaceutically acceptable salts or solvates thereof according to any one of claims 1∼5for use in preparing a human drug for treating or preventing male erectile dysfunction, benign prostatic hyperplasia,female sexual dysfunction, premature delivery, menorrhalgia, bladder outlet obstruction, incontinence, instable andvariant Prinzmetal angina pectoris, hypertension, pulmonary hypertension, congestive heart failure, renal failure,atherosclerosis, apoplexy, peripheral vascular disease, Raynaud’s diseases, inflammation diseases, bronchitis,chronicity asthma, allergic asthma, allergic coryza, glaucoma or diseases characterized by enterocinesia dysfunc-tion.

12. The compound of formula I, the pharmaceutically acceptable salts or solvates thereof for use according to claim 11,wherein, the said compound of formula I, the pharmaceutically acceptable salts or solvates thereof are further usedin combination with a selective 5-HT reuptake inhibitor, an α-receptor blockade, an antihypertensive drug, propionyl-L-carnitine, testosterone undecanoate or Tianeptine.

Patentansprüche

1. Verbindung der Formel I, pharmazeutisch verträgliche Salze oder Solvate davon

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Wobei:

R1 und R2 sind jeweils unabhängig H; C1-C10 Alkyl; C3-C6 Alkenyl; C3-C6 Cycloalkyl; Halogen; CF3; OR5;NHCOR8; Aryl oder C1-C4 Alkyl optional substituiert mit Aryl oder OR5; Z ist OR3;R3 ist C1-C6 Alkyl; C3-C6 Cycloalkyl; C3-C6 Alkenyl; C1-C3 Haloalkyl oder C1-C3 Alkyl substituiert mit C1-C3Alkoxy oder C3-C6Cycloalkyl;R4 ist NO2; CN; SO2NR6R7; NR9R10. COR11; OR12; C2-C4 Alkyl optional substituiert mit OH, CN, C1-C4 Alkoxy,NR6R7, CONR6R7 oder CO2R8; C2-C4 Alkenyl optional substituiert mit CN, CONR6R7 oder CO2R8; oder R4 istein 5~7-gliedriges Heterocyclyl optional substituiert mit einem oder mehreren Substituenten ausgewählt ausOH, COOR8, CONH2, C1-C6 Alkyl, C1-C4 Alkoxy, C3-C6 Cycloalkyl, Aryl, Het und C1-C6 Alkyl substituiert mitHalogen oder Alkoxy oder Hydroxyl; oder R4 ist eine 5- oder 6-gliedrige Monosaccharidgruppe optional substi-tuiert mit einem oder mehreren Substituenten ausgewählt aus C1-C6 Alkyl, Trimethylsilyl, Benzyl und Acetyl;R5 ist H; C1-C6 Alkyl; C3-C6 Alkenyl; C3-C6 Cycloalkyl; C1-C4 Alkyl optional substituiert mit OH, C1-C4 Alkoxyoder NR6R7; Aryl oder Het;R6 und R7 sind jeweils unabhängig H, OH, C1-C6 Alkyl, C1-C6 Alkoxy, C3-C6 Alkenyl, C3-C6 Cycloalkyl, Ada-mantyl, C3-C8 Lactamyl, Aryl, Het oder (CH2CH2O)jH wobei j 1~3 ist; oder R6 und R7 sind jeweils unabhängigC1-C6 Alkyl optional substituiert mit OH, C1-C4 Alkoxy, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2,NR13R14, Aryl, Het oder 4~8-gliedrigem Heterocyclyl; oder R6 und R7 sind jeweils unabhängig ein 4~8-gliedrigesHeterocyclyl optional substituiert mit einem oder mehreren Substituenten ausgewählt aus OH, COOR8, CONH2,COR16, SO2R16, C1-C6 Alkyl, C1-C4 Alkoxy, C3-C6 Cycloalkyl, Aryl, Het und C1-C6 Alkyl substituiert mit Halogenoder C1-C4 Alkoxy oder Hydroxyl; oder R6 und R7, zusammen mit dem Stickstoffatom, an das sie gebundensind, bilden ein 4~8-gliedriges Heterocyclyl optional substituiert mit einem oder mehreren Substituenten aus-gewählt aus OH, COOR8, CONH2, COR16, SO2R16, C1-C6 Alkyl, (CH2CH2O)jH wobei j 1∼3 ist, C1-C4 Alkoxy,C3-C6 Cycloalkyl, Aryl, Het und C1-C6 Alkyl substituiert mit Halogen oder C1-C4 Alkoxy oder Hydroxyl oder Aryl;oder R6 und R7, zusammen mit dem Stickstoffatom, an das sie gebunden sind, bilden eine Glucosylaminogruppe,Aminosäurerest, Aminosäureesterrest oder Aminoamidrest, welche optional substituiert sind mit einem odermehreren Substituenten ausgewählt aus C1-C6 Alkyl, NR13R14, COR16, Benzyl, Benzyloxycarbonyl und t-Bu-tyloxycarbonyl;R8 ist H, C1-C6 Alkyl oder Aryl;R9 ist H, C1-C6 Alkyl oder SO2R16;R10 ist H; C1-C6 Alkyl; COR15; SO2NR6R7; SO2R16;

eine 5- oder 6-gliedrige Monosaccharidgruppe optional substituiert mit einem oder mehreren Substituentenausgewählt aus C1-C6 Alkyl, Trimethylsilyl, Benzyl und Acetyl; oder R10 ist ein 5-gliedriges Heterocyclyl optionalsubstituiert mit einem oder mehreren Substituenten; oder wenn R9 H ist, ist R10 ein Aminosäurerest optionalsubstituiert mit einem oder mehreren Substituenten ausgewählt aus OH, C1-C6 Alkyl, C1-C4 Alkoxy, COR16,Benzyl, Benzyloxycarbonyl und t-Butyloxycarbonyl;R11 ist H; OH; C1-C6 Alkyl; Aryl; Het; NH(CH2)kNH2, NH(CH2)kNHSO2R16, oder NH(CH2)kNHCOR16, wobei k0~4 ist; C1-C3Alkyl substituiert mit Halogen, OH oder C1-C6 Alkoxy; oder (CH2)mNR6R7, wobei m 0~2 ist; oderR11 ist ein Aminosäurerest oder ein Aminoamidrest optional substituiert mit C1-C6 Alkyl oder C1-C4 Alkoxy;R12 ist H, COR19, SO2R16, oder eine 5- oder 6-gliedrige Monosaccharidgruppe optional substituiert mit einemoder mehreren Substituenten ausgewählt aus C1-C6 Alkyl, Trimethylsilyl, Benzyl und COR16;R13 und R14 sind jeweils unabhängig H oder C1-C6 Alkyl; oder R13 und R14, zusammen mit dem Stickstoffatom,an das sie gebunden sind, bilden ein 4~8-gliedriges Heterocyclyl optional substituiert mit einem oder mehrerenSubstituenten ausgewählt aus OH, C1-C6 Alkyl, C1-C4 Alkoxy, C3-C6 Cycloalkyl, Aryl und Het;

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R15 ist H; CF3; C1-C6 Alkyl optional substituiert mit Halogen, OH, C1-C6 Alkoxycarbonylamino, NR13R14,NHSO2R16, NHCOR16, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, Aryl oder Het; (CH2)nCOOR8 oder(CH2)nCONHR8, wobei n 0∼6 ist; C2-C4 Alkenyl optional substituiert mit C1-C6 Alkyl, OH, C1-C6 Alkoxy oderNR13R14; C3-C6 Cycloalkyl optional substituiert mit C1-C6 Alkyl oder OH; C3-C6 Cycloalkoxy optional substituiertmit C1-C6 Alkyl oder OH; Aryl oder Het;R16 ist C1-C6Alkyl, Aryl oder Het;R17 und R18 sind jeweils unabhängig H; C1-C6 Alkyl optional substituiert mit OH, SO3H, SO2NR13R14, SO2R16,PO(OH)2, PO(OR16)2, NR13R14, Aryl, Het oder einem 4~8-gliedrigen Heterocyclyl; C3-C6 Cycloalkyl oder Aryloptional substituiert mit OH; oder R17 und R18, zusammen mit dem Stickstoffatom, an das sie gebunden sind,bilden ein 4~8-gliedriges Heterocyclyl optional substituiert mit einem oder mehreren Substituenten ausgewähltaus OH, C1-C6 Alkyl, C1-C4 Alkoxy, C3-C6 Cycloalkyl, Aryl und Het;R19 ist C1-C6 Alkyl, Aryl oder NHR8;R20 ist C1-C3 Alkyl;Halogen ist F, Cl, Br oder I;Y ist O, S oder NR8;das genannte "Aryl" ist Phenyl, unsubstituiert oder substituiert mit einem oder mehreren Substituenten ausge-wählt aus Halogen, C1-C3Alkyl, C1-C3Alkoxy, CF3, CN und NO2;die genannten "5~7-gliedriges Heterocyclyl", "4~8-gliedriges Heterocyclyl" und "5-gliedriges Heterocyclyl" be-zeichnen gesättigtes oder ungesättigtes Heterocyclyl, umfassend ein oder mehrere Heteroatome ausgewähltaus N, S und O;das genannte "Het" ist ein 5~6-gliedriges aromatisches Heterocyclyl umfassend 1~4 Heteroatome ausgewähltaus N, S und O, das genannte 5~6-gliedrige aromatische Heterocyclyl ist optional substituiert mit einem odermehreren Substituenten ausgewählt aus Halogen, C1-C3 Alkyl, C1-C3Alkoxy, CF3, CN und NO2.

2. Verbindung der Formel I, pharmazeutisch verträgliche Salze oder Solvate davon nach Anspruch 1, wobei:

R1 und R2 sind jeweils unabhängig H; C1-C10 Alkyl; Halogen; CF3; OR5; NHCOR8; Aryl oder C1-C4 Alkyl optionalsubstituiert mit Aryl oder OR5;Z ist OR3;R3 ist C1-C6 Alkyl oder C1-C3 Alkyl substituiert mit C1-C3 Alkoxy;R4 ist NO2; CN; SO2NR6R7; NR9R10; COR11; OR12; C2-C4 Alkyl optional substituiert mit OH, C1-C4 Alkoxy oderNR6R7; oder R4 ist ein 5- oder 6-gliedriges Heterocyclyl optional substituiert mit einem oder mehreren Substi-tuenten ausgewählt aus OH, COOR8, CONH2, C1-C6 Alkyl, C1-C4 Alkoxy, C3-C6 Cycloalkyl, Aryl, Het und C1-C6Alkyl substituiert mit OH; oder R4 ist eine 5-oder 6-gliedrige Monosaccharidgruppe optional substituiert miteinem oder mehreren Substituenten ausgewählt aus C1-C6 Alkyl, Trimethylsilyl, Benzyl und Acetyl;R5 ist H; C1-C6 Alkyl; C1-C4 Alkyl optional substituiert mit OH, C1-C4 Alkoxy oder NR6R7; oder Aryl;R6 und R7 sind jeweils unabhängig H, OH, C1-C6 Alkyl, C1-C6 Alkoxy, C3-C6 Alkenyl, C3-C6 Cycloalkyl, Ada-mantyl, C3-C8 Lactamyl, Aryl, Het oder (CH2CH2O)jH wobei j 1~3 ist; oder R6 und R7 sind jeweils unabhängigC1-C6 Alkyl optional substituiert mit OH, C1-C4 Alkoxy, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2,NR13R14, Aryl, Het oder einem 4~8-gliedrigen Heterocyclyl; oder R6 und R7 sind jeweils unabhängig ein 4~8-gliedriges Heterocyclyl, wobei das genannte 4~8-gliedrige Heterocyclyl Furyl, Thienyl, Thiazolyl, Imidazolyl,Pyrazolyl, Pyridyl, Pyrimidinyl, Pyrazinyl, Morpholinyl, Thiomorpholinyl, Piperidyl, Pyrrolidinyl oder Piperazinylist, und das genannte 4~8-gliedrige Heterocyclyl ist optional substituiert mit einem oder mehreren Substituentenausgewählt aus OH, COOR8, CONH2, COR16, SO2R16, C1-C6 Alkyl, C3-C6 Cycloalkyl, Aryl, Het und C1-C6Alkyl substituiert mit C1-C4 Alkoxy oder Hydroxyl; oder R6 und R7, zusammen mit dem Stickstoffatom, an dassie gebunden sind, bilden ein 4~8-gliedriges Heterocyclyl optional substituiert mit einem oder mehreren Sub-stituenten ausgewählt aus OH, COOR8, CONH2, COR16, SO2R16, C1-C6 Alkyl, (CH2CH2O)jH wobei j 1∼3 ist,C3-C6 Cycloalkyl, Aryl, Het und C1-C6 Alkyl substituiert mit C1-C4 Alkoxy oder Hydroxyl oder Aryl; oder R6 undR7, zusammen mit dem Stickstoffatom, an das sie gebunden sind, bilden eine Glucosylaminogruppe, Amino-säurerest, Aminosäureesterrest oder Aminoamidrest, welche optional substituiert sind mit einem oder mehrerenSubstituenten ausgewählt aus C1-C6 Alkyl, NR13R14, COR16, Benzyl, Benzyloxycarbonyl und t-Butyloxycarbo-nyl;R8 ist H, C1-C6 Alkyl oder Aryl;R9 ist H, C1-C6Alkyl oder SO2R16;R10 ist H; C1-C6 Alkyl; COR15; SO2R16;

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eine 5- oder 6-gliedrige Monosaccharidgruppe; oder R10 ist Dihydroimidazolyl substituiert mit Hydroxyalkyl,oder 1,2,4-Triazolyl optional substituiert mit C1-C6 Alkyl, Aryl oder einer Aminogruppe; oder wenn R9 H ist, istR10 ein Aminosäurerest optional substituiert mit einem oder mehreren Substituenten ausgewählt aus OH, C1-C6Alkyl, C1-C4 Alkoxy, COR16, Benzyl, Benzyloxycarbonyl und t-Butyloxycarbonyl;R11 ist H; OH; C1-C6 Alkyl; Aryl; Het; NH(CH2)kNH2, NH(CH2)kNHSO2R16 oder NH(CH2)kNHCOR16, wobei k0~4 ist; C1-C3 Alkyl substituiert mit Halogen, OH oder C1-C6 Alkoxy; oder (CH2)mNR6R7, wobei m 0~2 ist; oderR11 ist ein Aminosäurerest oder Aminoamidrest, welche optional substituiert sind mit C1-C4 Alkoxy;R12 ist H, COR19, SO2R16 oder eine 5-oder 6-gliedrige Monosaccharidgruppe;R13 und R14 sind jeweils unabhängig H oder C1-C6 Alkyl; oder R13 und R14, zusammen mit dem Stickstoffatom,an das sie gebunden sind, bilden ein 4~8-gliedriges Heterocyclyl optional substituiert mit einem oder mehrerenSubstituenten ausgewählt aus OH und C1-C6Alkyl;R15 ist H; CF3; C1-C6 Alkyl optional substituiert mit Halogen, OH, C1-C6 Alkoxycarbonylamino, NR13R14,NHSO2R16, NHCOR16, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, Aryl oder Het; (CH2)nCOOR8 oder(CH2)nCONHR8, wobei n 0∼6 ist; C2-C4 Alkenyl optional substituiert mit C1-C6 Alkyl, OH, C1-C6 Alkoxy oderNR13R14; C3-C6 Cycloalkyl optional substituiert mit C1-C6 Alkyl oder OH; C3-C6 Cycloalkoxy optional substituiertmit C1-C6 Alkyl oder OH; Aryl oder Het;R16 ist C1-C6Alkyl oder Aryl;R17 und R18 sind jeweils unabhängig H; C1-C6 Alkyl optional substituiert mit OH, SO3H, SO2NR13R14, SO2R16,PO(OH)2, PO(OR16)2, NR13R14, Aryl, Het oder einem 4~8-gliedrigen Heterocyclyl; C3-C6 Cycloalkyl; oder Aryloptional substituiert mit OH; oder R17 und R18, zusammen mit dem Stickstoffatom, an das sie gebunden sind,bilden ein 4~8-gliedriges Heterocyclyl optional substituiert mit einem oder mehreren Substituenten ausgewähltaus OH und C1-C6Alkyl;R19 ist C1-C6Alkyl, Aryl oder NHR8;R20 ist C1-C3Alkyl;Halogen ist F, Cl, Br oder I;Y ist O, S oder NR8;das genannte "Aryl" ist Phenyl, unsubstituiert oder substituiert mit einem oder mehreren Substituenten ausge-wählt aus Halogen, C1-C3 Alkyl und C1-C3 Alkoxy;die genannten "5- oder 6-gliedriges Heterocyclyl", "4~8-gliedriges Heterocyclyl" und "5-gliedriges Heterocyclyl"bezeichnen gesättigtes oder ungesättigtes Heterocyclyl, umfassend ein oder mehrere Heteroatome ausgewähltaus N, S und O;das genannte "Het" ist ein 5~6-gliedriges aromatisches Heterocyclyl umfassend 1~4 Heteroatome ausgewähltaus N, S und O, das genannte 5~6-gliedrige aromatische Heterocyclyl ist optional substituiert mit einem odermehreren Substituenten ausgewählt aus Halogen, C1-C3 Alkyl, C1-C3Alkoxy, CF3, CN und NO2.die genannte "Aminosäure" ist Glycin, Alanin, Phenylalanin, Serin, Tryptophan, Valin, Leucin, Isoleucin, t-Leucin,Tyrosin, Lysin, Histidin, Methionin, Arginin, Threonin, Aspartat, Cystein, Prolin, Glutaminsäure, Asparagin, Glu-tamin, Ornithin oder Citrullin;das genannte "5- oder 6-gliedrige Monosaccharid" ist Ribose, Deoxyribose, Xylose, Arabinose, Glucose, Man-nose, Galactose oder Fructose.

3. Verbindung der Formel I, pharmazeutisch verträgliche Salze oder Solvate davon

wobei

R1 ist H, F, Cl, Br, I, OH, Methyl, Ethyl, Propyl, Isopropyl oder Acetamido;

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R2 ist Br, CF3, OR5, Ethyl, Propyl, Isopropyl, Benzylamino, Phenyl, Benzyl, Isobutyl, n-Octyl oder Acetamido;Z ist OR3;R3 ist Ethyl, Propyl, n-Butyl, n-Hexyl oder 3-Methoxylpropyl;R4 ist NO2, SO2NR6R7, NR9R10, COR11, OR12 oder Glucosyl; oder R4 ist ein 5- oder 6-gliedriges Heterocyclyl,wobei das genannte 5- oder 6-gliedrige Heterocyclyl Thienyl, Thiazolyl, 1,2,4-Triazolyl, Imidazolyl, Pyrrolyl,Oxadiazolyl, Pyrimidinyl, Morpholinyl, Thiomorpholinyl, Piperidyl, Pyrrolidinyl oder Piperazinyl ist, und das ge-nannte 5- oder 6-gliedrige Heterocyclyl ist optional substituiert mit einem oder mehreren Substituenten ausge-wählt aus OH, COOH, CONH2, C1-C6 Alkyl, C1-C4 Alkoxy, C3-C6 Cycloalkyl, Aryl, Het und C1-C6 Alkyl substituiertmit OH;R5 ist H; C1-C4Alkyl optional substituiert mit OH, C1-C4Alkoxy oder NR6R7; oder Aryl;R6 und R7 sind jeweils unabhängig H, Methyl, Methoxyl, Cyclopropyl, Propenyl, Isobutyl, t-Butyl, Adamantyl,Cyclohexyl, Caprolactamyl, 2-(1-Methylpyrrol-2-yl)ethylamino, Pyridylmethyl, Thienylmethyl,

oder C2-C3 Alkyl optional substituiert mit OH, NR13R14, SO3H, SO2NR13R14 oder 5~6-gliedriges Heterocyclyl,wobei das genannte 5~6-gliedrige Heterocyclyl Morpholinyl, Thiomorpholinyl, Piperidyl, Pyrrolidinyl oder Pipe-razinyl ist, und das genannte 5~6-gliedrige Heterocyclyl ist optional substituiert mit einem oder mehreren Sub-stituenten ausgewählt aus OH, COOR8, CONH2, COR16, SO2R16, C1-C6 Alkyl und Aryl; oder R6 und R7, zu-sammen mit dem Stickstoffatom, an das sie gebunden sind, bilden ein 5~6-gliedriges Heterocyclyl, wobei dasgenannte 5~6-gliedrige Heterocyclyl Morpholinyl, Thiomorpholinyl, Piperidyl, Pyrrolidinyl oder Piperazinyl ist,und das genannte 5~6-gliedrige Heterocyclyl ist optional substituiert mit einem oder mehreren Substituentenausgewählt aus OH, COOR8, CONH2, COR16, SO2R16, C1-C6 Alkyl, (CH2CH2O)jH wobei j 1~2 ist, Dichlorphenyl,Benzyl, Pyridyl und Aryl; oder NR6R7 ist eine Glucosylaminogruppe, Aminosäurerest, Aminosäureesterrest oderAminoamidrest, welche optional substituiert sind mit einem oder mehreren Substituenten ausgewählt ausNR13R14 und Acetyl;R8 ist H, Methyl oder Ethyl;R9 ist H, Methyl oder SO2R16;R10 ist H, Methyl, COR15, SO2R16,

Glucosyl oder Mannosyl; Dihydroimidazolyl substituiert mit Hydroxyethyl; oder wenn R9 H ist, ist R10 ein Ami-nosäurerest optional substituiert mit einem oder mehreren ausgewählt aus OH, t-Butyloxycarbonyl und Acetyl;R11 ist OH; Pyrazolyl substituiert mit Isopropyl; Aminosäurerest; Aminoesterrest; NR6R7; CH2Br oder CH2NR6R7;R12 ist H, COR19, SO2R16, Mannosyl oder Glucosyl;R13 und R14 sind jeweils unabhängig H oder Ethyl; oder R13 und R14, zusammen mit dem Stickstoffatom, andas sie gebunden sind, bilden ein 5~6-gliedriges Heterocyclyl, wobei das genannte 5~6-gliedrige HeterocyclylMorpholinyl, Piperidyl, Pyrrolidinyl oder Piperazinyl ist, und das genannte 5~6-gliedrige Heterocyclyl ist optionalsubstituiert mit einem oder mehreren Substituenten ausgewählt aus OH und C1-C6 Alkyl;R15 ist H; Methyl; Ethyl; Cyclohexyl; CF3; (CH2)nCOOR8 oder (CH2)nCONH2, wobei n 0 oder 1 ist; Vinyl; Propenyl;Pyridyl; Phenyl substituiert mit Ethoxy; oder Thiazolyl substituiert mit Isopropyl;R16 ist Methyl;R17 und R18 sind jeweils unabhängig H, Ethyl oder Phenyl; oder R17 und R18, zusammen mit dem Stickstoffatom,an das sie gebunden sind, bilden ein 4~8-gliedriges Heterocyclyl, wobei das genannte 4~8-gliedrige HeterocyclylMorpholinyl, Piperidyl, Pyrrolidinyl oder Piperazinyl ist, und das genannte 4~8-gliedrige Heterocyclyl ist optionalsubstituiert mit einem oder mehreren Substituenten ausgewählt aus OH und C1-C6 Alkyl; oder wenn Y NH ist,bilden R17 und C(Y)N ein Dihydroimidazolyl;R19 ist Methyl oder NHC2H5;R20 ist Methyl;Halogen ist F, Cl, Br oder I;Y ist O, S, NH oder NC2H5;

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das genannte "Aryl" ist Phenyl, unsubstituiert oder substituiert mit einem oder mehreren Substituenten ausge-wählt aus Halogen, C1-C3Alkyl und C1-C3Alkoxy;das genannte "Het" ist ein 5~6-gliedriges aromatisches Heterocyclyl umfassend 1~4 Heteroatome ausgewähltaus N, S und O, das genannte 5~6-gliedrige aromatische Heterocyclyl ist optional substituiert mit einem odermehreren Substituenten ausgewählt aus Halogen, C1-C3 Alkyl, C1-C3Alkoxy, CF3, CN und NO2.die genannte "Aminosäure" ist Glycin, Alanin, Phenylalanin, Serin, Tryptophan, Valin, Leucin, Isoleucin, t-Leucin,Tyrosin, Lysin, Histidin, Methionin, Arginin, Threonin, Aspartat, Cystein, Prolin, Glutaminsäure, Asparagin, Glu-tamin, Ornithin oder Citrullin;das genannte "5- oder 6-gliedrige Monosaccharid" ist Glucose oder Mannose.

4. Verbindung der Formel I, pharmazeutisch verträgliche Salze oder Solvate davon nach Anspruch 1, wobei die ge-nannte Phenylpyrimidonverbindung ausgewählt ist aus:

6-Isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,6-Ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,6-Acetamido-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Brom-6-isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,6-Isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Brom-6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Chlor-6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Acetamido-6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Brom-6-isopropyl-2-[2-n-butoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Brom-6-n-octyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Brom-6-phenyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Methyl-6-isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Fluor-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Methyl-6-ethyl-2-(2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Hydroxy-6-isopropyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Brom-6-isopropyl-2-[2-n-hexyloxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Brom-6-isobutyl-2-[2-ethoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Brom-6-isopropyl-2-{2-n-propoxyl-5-[N-methyl-N-(2-hydroxyethyl)aminosulfonyl]phenyl}pyrimid-4(3H)-on,5-Brom-6-isopropyl-2-{2-n-propoxyl-5-[N-(2-morpholinoethyl)aminosulfonyl]phenyl}pyrimid-4(3H)-on,5-Brom-6-isopropyl-2-{2-n-propoxyl-5-[N-(3-morpholinopropyl)aminosulfonyl]phenyl}pyrimid-4(3H)-on,5-Brom-6-isopropyl-2-{2-n-propoxyl-5-[N-(N’,N’-diethylamino)ethylaminosulfonyl]phenyl}pyrimid-4(3H)-on,5,6-Diethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5,6-Diethyl-2-{2-n-propoxyl-5-[N-methyl-N-(hydroxyethyl)aminosulfonyl]phenyl}pyrimid-4(3H)-on,5,6-Diethyl-2-{2-n-propoxyl-5-[N-(2-ethylaminoethyl)aminosulfonyl)phenyl}pyrimid-4(3H)-on,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylsulfonylprolin,2-(5-Nitro-2-n-propoxyphenyl)-5-brom-6-isopropylpyrimid-4(3H)-on,2-(5-Amino-2-n-propoxyphenyl)-5-brom-6-isopropylpyrimid-4(3H)-on,1-(3-(4-Isopropyl-5-brom-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylthioharnstoff,1-[3-(4-Isopropyl-5-brom-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-3-ethyl-2-methylisothioharn-stoff,N-[3-(4-Isopropyl-5-brom-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’,N"-triethylguanidin,N-[3-(4-Isopropyl-5-brom-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-piperidyl-1-formami-din,N-[3-(4-Isopropyl-5-brom-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-pyrrolyl-1-formamidin,2-{2-[3-(4-Isopropyl-5-brom-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]amino-4,5-dihydro-imidazol-1-yl}-ethanol,2-(5-Nitro-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-on,2-(5-Amino-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-on,1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylthioharnstoff,1-[3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-3-ethyl-2-methylisothioharnstoff,N-[3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-piperidyl-1-formamidin,N-[3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’,N"-triethylguanidin,2-{2-[3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]amino-4,5-dihydro-imidazol-1-yl}-ethanol,N-[3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’-ethyl-pyrrolyl-1-formamid,

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N-[3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-pyrrolyl-1-formamidin,5-Brom-6-isopropyl-2-(2-n-propoxyl-5- mesylamidophenyl)pyrimid-4(3H)-on,5,6-Diethyl-2-(2-n-propoxyl-5-mesylamidophenyl)pyrimid-4(3H)-on,N-(3-(1,6-Dihydro-4-isopropyl-5-brom-6-oxopyrimidin-2-yl)-4-propoxyphenyl)acetamid,N-(3-(1,6-Dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)acetamid,N-(3-(1,6-Dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)propionamid,N-(3-(1,6-Dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)cyclohexamid,N-(3-(1,6-Dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)formamid,N-(3-(1,6-Dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)-1-t-butyloxycarbonyl-4-hydroxy-prolyla-mid,4-n-Propoxyl-3-(1,6-dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)benzoesäure,(Morpholin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenon,(Piperid-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenon,(2-Aminoformylpyrrol-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenon,4-n-Propoxyl-3-(1,6-dihydro-4-isopropyl-6-oxopyrimidin-2-yl)benzoesäure,(Morpholin-1-yl)(3-(4-isopropyl-5-brom-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenon,(Piperid-1-yl)(3-(4-isopropyl-5-brom-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenon,(4-Methyl-piperazin-1-yl)(3-(4-isopropyl-5-brom-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenon,2-(5-(N,N-Dimethylamino-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-on,1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)harnstoff,1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylharnstoff,1-(3-(4-Isopropyl-5-brom-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-phenylthioharnstoff,1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-guanidin,5-Brom-6-isopropyl-2-(5-(2-bromacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-on,5-Brom-6-isopropyl-2-(5-(2-morpholinylacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-on,5-Brom-6-isopropyl-2-(5-(2-(4-methyl-piperazin-1-yl)acetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-on,5,6-Diethyl-2-(5-(2-bromacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-on,5,6-Diethyl-2-(5-(2-(4-methyl-piperazin-1-yl)acetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-on,5,6-Diethyl-2-(5-(2-morpholinylacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-on,5-Brom-6-isopropyl-2-(2-n-propoxyl-5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-ylami-no)phenyl)pyrimid-4(3H)-on,5-Brom-6-isopropyl-2-(2-n-propoxyl-5-(tetrahydro-3,4-dihydroxy-5-(1,2-dihydroxyethyl)fur-2-ylamino)phe-nyl)pyrimid-4(3H)-on,5,6-Diethyl-2-(2-n-propoxyl-5-(tetrahydro-3,4-dihydroxy-5-(1,2-dihydroxyethyl)fur-2-ylamino)phenyl)pyrimid-4(3H)-on,5,6-Diethyl-2-(2-n-propoxyl-5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-ylamino)phenyl)pyri-mid-4(3H)-on,2-(5-Hydroxy-2-n-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-on,(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)acetat,(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)ethylaminoformiat,5,6-Diethyl-2-(2-n-propoxyl-5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yloxy)phenyl)pyri-mid-4(3H)-on,(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)mesylat,2-(5-(2,5-Dimethyl-1H-pyrrol-1-yl)-2-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-on,2,2’-(4-n-Propoxyl-1,3-phenylen)bis(5,6-diethylpyrimid-4(3H)-on),2-(5-(1,3,4-Oxadiazol-2-yl)-2-propoxyphenyl)-5,6-diethylpyrimid-4(3H)-on,Ethyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)acetat,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-morpholinylethyl)-4-n-propoxybenzamid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N,N-di(2-hydroxyethyl)-4-n-propoxybenzamid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-caprolactam-3-yl)-4-n-propoxybenzamid,(4-(2,3-Dichlorphenyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophe-non,(3-Isopropylpyrazol-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenon,N-Cyclohexyl-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamid,N-((Pyrid-2-yl)methyl)-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamid,Methyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3,3-dimethylbutyrat,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2,2,2-trifluoracetamid,Ethyl-N-(3-(4, 5-d iethyl-1, 6-d ihydro-6-oxopyri m id in-2-yl)-4-n-propoxyphenyl)aminoformylformiat,

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N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)acrylamid,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-crotonamid,Ethyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformylacetat,2-Ethoxyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)benzamid,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)nicotinamid,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-5-isopropylthiazolyl-2-formamid,t-Butyl-3-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformyl)propylaminofor-miat,4-Acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)butyramid,1-Acety)-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)pyrrolidinyl-2-formamid,2-Acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-methylbutyramid,2-Acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-phenylpropionamid,2-Acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)propionamid,2,6-Diacetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)hexanamid,N1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)propandiamid,N1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)oxalamid,N-(Aminoformylmethyl)-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamid,5,6-Diethyl-2-{2-n-propoxyl-5-[(2-(1-methylpyrrol-2-yl)ethyl)aminosulfonyl]phenyl}pyrimid-4(3H)-on,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-(1-methylpyrrol-2-yl)ethyl)-4-n-propoxylbenzamid,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5-harnstoffpentan-säure,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5-aminopentansäure,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-methylbutansäure,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropansäure,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-hydroxypropansäu-re,Ethyl-2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropionat,3-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropylsulfonsäure,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminoethylsulfonsäure,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-aminoformylpro-pansäure,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-indolpropionsäure,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminoessigsäure,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3,3-dimethylbutan-säure,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-4-aminoformylbutan-säure,Ethyl-2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-methylvale-rat,Methyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylsulfonamido)-6-acetamidocapro-at,5,6-Diethyl-2-(2-n-propoxyl-5-(4-hydroxyethyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5,6-Diethyl-2-(2-n-propoxyl-5-(3-hydroxypropylaminosulfonyl)phenyl]pyrimid-4(3H)-on,5,6-Diethyl-2-(2-n-propoxyl-5-(N-(2-morpholinylethyl)-N-(2-hydroxyethyl)aminosulfonyl)phenyl)pyrimid-4(3H)-on,5,6-Diethyl-2-(2-n-propoxyl-5-(N-methyl-N-(2-(pyrrolidin-1-yl)ethyl)aminosulfonyl)phenyl)pyrimid-4(3H)-on,5,6-Diethyl-2-(2-n-propoxyl-5-(2-(N,N-diethyl)aminoethylaminosulfonyl)phenyl]pyrimid-4(3H)-onmaleat,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phenylpropansäure,Methyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzoylprolinat,Methyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-(4-hydroxyphenyl)propio-nat,Ethyl-2-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-(1H-indol-3-yl)propionat,Methyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-methylbutyrat,Methyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-(1H-imidazol-4-yl)propio-nat,Ethyl-2-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-methylvalerat,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)propionsäure,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-aminoformylpropionsäure,

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2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-4-aminoformylbutansäure,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-hydroxypropionsäure,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-guanidinopentansäure,Methyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phenylpropionat,Methyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propionat,Methyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-4-methylvalerat,Ethyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propionat,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-(4-methylpiperazin-1-yl)-1-oxopropan-2-yl)-4-n-propoxy-benzamid,N-(1-Aminoformylethyl)-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl-N-(2-(thien-2-yl)ethyl)benzamid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl-N-((fur-2-yl)methyl)benzamid,N-t-Butyl-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-isobutyl-4-n-propoxylbenzamid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-allyl-4-n-propoxylbenzamid,(4-(Pyrid-2-yl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophenon,(4-(Hydroxyethyloxylethyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzo-phenon,(4-(Hydroxyethyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophenon,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(3-hydroxypropyl)-4-n-propoxylbenzamid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-hydroxy-2-propyl)-4-n-propoxybenzamid,N-Ethyl-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-hydroxyethyl)-4-n-propoxylbenzamid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-diethylaminoethyl)-4-n-propoxylbenzamid,3-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propyl-1-sulfonsäure,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)ethylsulfonsäure,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-hydroxyethyl)-N-methyl-4-n-propoxylbenzamid,(4-Benzylpiperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophenon,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-methyl-N-(2-(pyrrolidin-1-yl)ethyl)-4-n-propoxybenzamid,Methyl-5-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)piperidyl-2-formiat,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-methoxyl-N-methyl-4-n-propoxybenzamid,5,6-Diethyl-2-[2-(3-methoxyln-propoxyl)-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,2-Chlor-N-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)acetamid,2-(Dimethylamino)-N-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)acetamid,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-(4-methylpiperazin-1-yl)acetamid,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-morpholinyl)acetamid,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-(piperid-1-yl)acetamid,Dimethyl-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylaminoformyl)methylphosphat,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)isobutyramid,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-methylbutyramid,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-phenylacetamid,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)benzamid,Ethyl-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylaminoformyl)propionat,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-5-oxopyrrolidinyl-2-formamid,2-Acetamido-N-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-4-methylpentanamid,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-acetamido-3-(1H-indol-3-yl)propion-amid,2-Acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)glutaramid,2-Acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-hydroxybutyramid,2-Acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-hydroxypropionamid,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylaminoformyl)-2-acetamidoethylacetat,5,6-Diethyl-2-(5-(ethylamino)-2-n-propoxyphenyl)pyrimid-4(3H)-on,N-Ethyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)propionamid,Ethyl-(N-ethyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformylformiat,1,3-Diethyl-1-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)harnstoff,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)piperidyl-1-formamid,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-4-methylpiperazinyl-1-formamid,1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-propylharnstoff,

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1-Cyclohexyl-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)harnstoff,1,1-Diethyl-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)harnstoff,1-(2-(Diethylamino)ethyl)-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)harnstoffmale-at,(4-Methylpiperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophenon,5-Iod-6-isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Chlor-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5,6-Diethyl-2-(2-n-propoxyl-5-((tetrahydro-2,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-3-ylamino)sulfo-nyl)phenyl]pyrimid-4(3H)-on,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-harnstoffpentansäure,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-aminopentansäure,3-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(tetrahydro-2,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-3-yl)-4-n-propoxybenzamid,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)ethylsulfamid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-methyl-piperazin-1-ylsulfonylethyl)-4-n-propoxybenza-mid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylethyl)-4-n-propoxybenzamid,3-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propylsulfamid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-methyl-piperazin-1-ylsulfonylpropyl)-4-n-propoxybenza-mid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylpropyl)-4-n-propoxybenzamid,5,6-Diethyl-2-(5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yl)-2-n-propoxyphenyl)pyrimid-4(3H)-on,5-lod-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5-Brom-6-ethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on, und5-Chlor-6-isopropyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on.

5. Verbindung der Formel I, pharmazeutisch verträgliche Salze oder Solvate davon nach einem der Ansprüche 1~3,wobei die genannte Phenylpyrimidonverbindung ausgewählt ist aus:

5,6-Diethyl-2-[2-n-propoxyl-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5,6-Diethyl-2-{2-n-propoxyl-5-[N-(2-morpholinylethyl)aminosulfonyl)phenyl}pyrimid-4(3H)-on,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenylsulfonylprolin,1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylthioharnstoff,N-[3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-N’,N"-triethylguanidin,N-[3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl]-pyrrolyl-1-formamid,5-Brom-6-isopropyl-2-(2-n-propoxyl-5-mesylamidophenyl)pyrimid-4(3H)-on,5,6-Diethyl-2-(2-n-propoxyl-5-mesylamidophenyl)pyrimid-4(3H)-on,N-(3-(1,6-Dihydro-4-isopropyl-5-brom-6-oxopyrimidin-2-yl)-4-propoxyphenyl)acetamid,N-(3-(1,6-Dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)acetamid,N-(3-(1,6-Dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)propionamid,N-(3-(1,6-Dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)cyclohexamid,N-(3-(1,6-Dihydro-4,5-diethyl-6-oxopyrimidin-2-yl)-4-propoxyphenyl)-1-t-butyloxycarbonyl-4-hydroxy-prolyla-mid,(Morpholin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenon,(Piperid-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenon,(2-Aminoformylpyrrol-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenon,(Morpholin-1-yl)(3-(4-isopropyl-5-brom-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophenon,1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)harnstoff,1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-ethylharnstoff,5,6-Diethyl-2-(5-(2-morpholinylacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-on,2,2’-(4-n-Propoxyl-1,3-phenylenyl)bis(5,6-diethylpyrimid-4(3H)-on),Ethyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)acetat,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2,2,2-trifluoracetamid,Ethyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)aminoformylacetat,4-Acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)butyramid,1-Acetyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)pyrrolidinyl-2-formamid,2-Acetamido-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-3-phenylpropionamid,

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N1-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)oxalamid,5,6-Diethyl-2-{2-n-propoxyl-5-[(2-(1-methylpyrrol-2-yl)ethyl)aminosulfonyl]phenyl}pyrimid-4(3H)-on,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-(1-methylpyrrol-2-yl)ethyl)-4-n-propoxylbenzamid,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5-harnstoffpentan-säure,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-5-aminopentansäure,Ethyl-2-(N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropionat,3-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminopropylsulfonsäure,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)aminoethylsulfonsäure,2-(N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)sulfonyl)amino-3-aminoformylpro-pansäure,5,6-Diethyl-2-(2-n-propoxyl-5-(4-hydroxyethyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-on,5,6-Diethyl-2-(2-n-propoxyl-5-(N-(2-morpholinylethyl)-N-(2-hydroxyethyl)aminosulfonyl)phenyl)pyrimid-4(3H)-on,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phenylpropansäure,Methyl-N-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzoylprolinat,Methyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-(4-hydroxyphenyl)propio-nat,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)propansäure,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-aminoformylpropansäure,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-guanidinopentansäure,Methyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phenylpropansäure,Methyl-2-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propansäure,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-(4-methylpiperazin-1-yl)-1-oxopropan-2-yl)-4-n-propoxy-benzamid,N-(1-Aminoformylethyl)-3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamid,(4-(Hydroxyethyoxylethyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzo-phenon,(4-(Hydroxyethyl)piperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophenon,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-hydroxy-2-propyl)-4-n-propoxybenzamid,3-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propyl-1-sulfonic acid,Methyl-5-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)piperidinyl-2-formiat,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)-2-(4-methylpiperazin-1-yl)acetamid,N-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)benzamid,1-(2-(Diethylamino)ethyl)-3-(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphenyl)harnstoffmale-at,(4-Methylpiperazin-1-yl)(3-(4,5-diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophenon,5,6-Diethyl-2-(2-n-propoxyl-5-((tetrahydro-2,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-3-ylamino)sulfo-nyl)phenyl]pyrimid-4(3H)-on,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-harnstoffpentansäure,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-aminopentansäure,3-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(tetrahydro-2,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-3-yl)-4-n-propoxybenzamid,2-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)ethylsulfamid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-methyl-piperazin-1-ylsulfonylethyl)-4-n-propoxybenza-mid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylethyl)-4-n-propoxybenzamid,3-(3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propylsulfamid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-methyl-piperazin-1-ylsulfonylpropyl)-4-n-propoxybenza-mid,3-(4,5-Diethyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diethylaminosulfonylpropyl)-4-n-propoxybenzamid und5,6-Diethyl-2-(5-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yl)-2-n-propoxyphenyl)pyrimid-4(3H)-on.

6. Verfahren zum Herstellen der Verbindung nach Formel I, pharmazeutisch verträgliche Salze oder Solvate davonnach Anspruch 1, wobei das Verfahren eine der folgenden Methoden ist:

(1) wenn R4 OH, SO2NR6R7, COR11, unsubstituiertes oder substituiertes C2-C4 Alkyl, unsubstituiertes oder

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substituiertes C2-C4 Alkenyl oder unsubstituiertes oder substituiertes 5~7-gliedriges Heterocyclyl ist, wird dieVerbindung der Formel I durch Cyclisieren der Verbindung der Formel II mit der Verbindung der Formel III inGegenwart einer Base hergestellt, wobei R1, R2, R3, R6, R7, R11 und das genannte 5~7-gliedrige Heterocyclylgleich definiert sind wie diese in Anspruch 1;

oder(2) die Verbindung der Formel I wird hergestellt aus der Verbindung der Formel la, der Verbindung der Formelle oder anderen Verbindungen der Formel I, wobei R1, R2, R3, R5, R6, R7, R8, R9, R10, R12, R15, R16, R17, R18,R19 und R20 gleich definiert sind wie diese in Anspruch 1; wobei:

1) wenn R4 SO2NR6R7 ist, die Verbindung der Formel Ib hergestellt wird aus der Verbindung der Formella durch Chlorsulfonierung gefolgt von Umsetzen mit R6R7NH in Gegenwart einer Base;

oder2) wenn R4 N02 ist, die Verbindung der Formel Ic hergestellt wird durch Nitrieren der Verbindung der FormelIa;

oder3) wenn R4 NH2 ist, die Verbindung der Formel Id hergestellt wird durch Reduzieren der Verbindung derFormel Ic

oder

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4) wenn R4 CN ist, die Verbindung der Formel If hergestellt wird aus der Verbindung der Formel le durchnucleophile Substitution mit Cyanid;

oder5) wenn R4 COOH ist, die Verbindung der Formel Ig hergestellt wird aus der Verbindung der Formel Ifdurch Hydrolyse;

oder6) wenn R4 NR9R10 ist, die Verbindung der Formel I hergestellt wird aus der Verbindung der Formel Idwobei R4 NH2 ist, wobei:

1> wenn R9 und R10 gleichzeitig Methyl sind, wird die Verbindung der Formel I durch N-Methylierungunter Verwenden eines Methylierungsmittels hergestellt;2> wenn R9 H ist und R10 SO2R16 ist, wird die Verbindung der Formel I hergestellt aus der Verbindungder Formel Id durch Sulfonylierung in Gegenwart einer Base;3> wenn R9 H ist und R10 COR15 ist, wird die Verbindung der Formel I hergestellt durch Umsetzen derVerbindung der Formel Id mit einem Acylchloridderivat einer organischen Säure, welches erhalten wirddurch Umsetzen der organischen Säure mit Oxalylchlorid oder Thionylchlorid; oder durch Kondensierender Verbindung der Formel Id mit einer organischen Säure;4> wenn R9 H ist, R10 C(Y)NR17R18 ist und Y O oder S ist, wird die Verbindung der Formel I hergestelltdurch die Additionsreaktion der Verbindung der Formel Id mit der Verbindung der Formel Y=C=NR17R18;5> wenn R9 H ist, R10 eine 5- oder 6-gliedrige Monosaccharidgruppe ist, wird die Verbindung derFormel I hergestellt durch Umsetzen der Verbindung der Formel Id mit einem 5- oder 6-gliedrigenMonosaccharid ohne Schutzgruppe in Gegenwart von Spuren einer organischen Säure als Katalysator;

6> wenn R9 H ist, R10 ist und Y NR8 ist, wird die Verbindung der Formel I hergestellt

durch nucleophile Substitution aus der Verbindung der Formel Ih mit einer Verbindung der FormelR17NHR18, wobei die Verbindung der Formel Ih hergestellt wird durch die Additionsreaktion der Ver-bindung der Formel Ii mit lodmethan, und die Verbindung der Formel Ii hergestellt wird durch dieAdditionsreaktion der Verbindung der Formel Id mit R8SCN;

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7> wenn R9 H ist und R10 ein Aminosäurerest, substituiert mit Acetyl, ist, Kondensieren der Verbindungder Formel Id mit einer N-Boc geschützten Aminosäure in Gegenwart eines Kupplungsmittels undeinem Aktivator, um ein Intermediat zu ergeben, gefolgt von Entschützen der Boc Gruppe in Trifluor-essigsäure und schließlich Umsetzen mit Essigsäureanhydrid in Pyridin, um die Verbindung der FormelI zu ergeben;

oder7) wenn R4 COR11 ist und R11 NR6R7 ist, wird die Verbindung der Formel I hergestellt durch Kondensierender Verbindung der Formel Ig mit R6R7NH; oder durch Umwandeln der Verbindung der Formel Ig in einkorrespondierendes Acylchloridderivat, gefolgt von Umsetzen mit R6R7NH;oder8) wenn R4 COR11 ist und R11 CH2NR6R7 ist, wird die Verbindung der Formel I hergestellt durch Konden-sieren der Verbindung der Formel Ij mit R6R7NH, wobei die Verbindung der Formel Ij hergestellt wird durchBromieren der Verbindung der Formel Ik, und die Verbindung der Formel Ik hergestellt wird durch Umsetzender Verbindung der Formel Ia mit Vinyl-n-butylether in Gegenwart eines Metallkatalysators, gefolgt vonHydrolyse; oder die Verbindung der Formel Ij auch hergestellt werden kann durch Friedel-Crafts Reaktionder Verbindung der Formel Ia mit Bromacetylbromid;

oder9) wenn R4 OR12 ist, wird die Verbindung der Formel I hergestellt aus der Verbindung der Formel II, wobei:

1> wenn R12 COR19 ist und R19 C1-C6 Alkyl oder Aryl ist, wird die Verbindung der Formel I hergestelltdurch Verestern der Verbindung der Formel II, wobei R4 OH ist;2> wenn R12 COR19 ist und R19 NHR8 ist, wird die Verbindung der Formel I hergestellt durch Additi-onsreaktion von R8NCO mit der Verbindung der Formel II, wobei R4 OH ist;3> wenn R12 SO2R16 ist, wird die Verbindung der Formel I hergestellt durch Sulfonylierung der Ver-bindung der Formel II, wobei R4 OH ist;4> wenn R12 eine 5- oder 6-gliedrige Monosaccharidgruppe ist, wird die Verbindung der Formel Inhergestellt durch zunächst Kondensieren der Verbindung der Formel II mit einem Hydroxyl-geschützten5- oder 6-gliedrigen Monosaccharid aktiviert mit Trichloracetonitril, um die Verbindung der Formel Imzu ergeben, gefolgt von Hydrolyse und Entschützung;

oder

10) wenn R4 Pyrrolyl ist, wird die Verbindung der Formel Io hergestellt durch Kondensieren von 2,5-He-xandion mit der Verbindung der Formel Id, wobei R4 NH2 ist;

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oder,11) wenn R4 ein Glycosid ist, wird die Verbindung der Formel I hergestellt durch zunächst Umsetzen derVerbindung der Formel Ie, wobei R4 Br ist, mit n-BuLi, dann Umsetzen mit einem geschützten Glucolacton,gefolgt von Reduzieren unter Verwenden eines Reduzierungsmittels;

oder(3) die Verbindung der Formel I wird hergestellt durch Umwandeln von anderen Verbindungen der Forme Iwobei R1 ein unterschiedlicher Substituent ist, wobei R2, R3 und R4 gleich definiert sind wie diese in Anspruch1; wobei:

1) wenn R1 ein Halogen ist, wird die Verbindung der Formel Iq hergestellt durch Halogenieren der Verbindungder Formel Ip, wobei R1 H ist, in Gegenwart einer organischen Base;

oder2) wenn R1 NH2 ist, wird die Verbindung der Formel Is hergestellt durch Hydrolysieren der Verbindung derFormel Ir, wobei R1 Acetamido ist

7. Verfahren zum Herstellen des Intermediats im Verfahren nach Anspruch 6 mit der folgenden Formel

wobei: Z ist OR3 und R3 und R4 sind gleich definiert wie diese in Anspruch 6,wobei das Verfahren folgende Schritte umfasst:

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die Verbindung der Formel III wird hergestellt durch Umsetzen der Verbindung der Formel IV mit Lithiumbis(tri-methylsilyl)amid in Tetrahydrofuran;

oder;die Verbindung der Formel III wird hergestellt durch zunächst Umsetzen der Verbindung der Formel IV mitHydroxylaminhydrochlorid, um die Verbindung der Formel V zu ergeben, gefolgt durch Hydrierung;

8. Pharmazeutische Zusammensetzung, umfassend eine therapeutisch wirksame Dosis von einem oder mehrerenausgewählt aus der Gruppe bestehend aus den Verbindungen der Formel I, den pharmazeutisch verträglichenSalzen oder Solvaten davon nach einem der Ansprüche 1 bis 5 und einem oder mehreren pharmazeutisch verträg-lichen Hilfsmitteln.

9. Pharmazeutische Zusammensetzung nach Anspruch 8, wobei die Dosis der genannten Verbindung der Formel I,der pharmazeutisch verträglichen Salze oder Solvate davon 1 bis 500 mg pro Tag beträgt.

10. Verbindung der Formel I, pharmazeutisch verträgliche Salze oder Solvate davon nach einem der Ansprüche 1 bis5 zur Verwendung im Herstellen eines Medikaments für Menschen.

11. Verbindung der Formel I, pharmazeutisch verträgliche Salze oder Solvate davon nach einem der Ansprüche 1 bis5 zur Verwendung im Herstellen eines Medikaments für Menschen zum Behandeln oder Verhindern von männlichererektiler Dysfunktion, benigner Prostatahyperplasie, weiblicher sexueller Dysfunktion, Frühgeburt, Menorrhagie,Blasenauslassobstruktion, Inkontinenz, instabiler und Variant Prinzmetal Angina pectoris, Hypertonie, pulmonalerHypertonie, Herzinsuffizienz, Nierenversagen, Arteriosklerose, Apoplexie, peripherer arterieller Verschlusskrank-heit, Raynaud-Erkrankungen, Entzündungskrankheiten, Bronchitis, chronischem Asthma, allergischem Asthma,allergischem Schnupfen, Glaukom oder Krankheiten, die durch peristaltische Dysfunktion gekennzeichnet sind.

12. Verbindung der Formel I, pharmazeutisch verträgliche Salze oder Solvate davon zur Verwendung nach Anspruch11, wobei die genannte Verbindung der Formel I, die pharmazeutisch verträglichen Salze oder Solvate davon fernerverwendet werden in Kombination mit einem selektiven 5-HT Wiederaufnahmehemmer, einem α-Rezeptor Blockie-rer, einem antihypertensiven Medikament, Propionyl-L-carnitin, Testosteronundecanoat oder Tianeptin.

Revendications

1. Composé de formule I, sels ou solvates pharmaceutiquement acceptables de celui-ci :

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où

R1 et R2 représentent chacun indépendamment H ; un alkyle en C1 à C10 ; un alcényle en C3 à C6 ; un cycloalkyleen C3 à C6 ; un halogène ; CF3 ; OR5 ; NHCOR8; un aryle ; ou un alkyle en C1 à C4 éventuellement substituépar un aryle ou OR5 ; Z représente OR3 ;R3 représente un alkyle en C1 à C6 ; un cycloalkyle en C3 à C6 ; un alcényle en C3 à C6 ; un haloalkyle en C1à C3 ; ou un alkyle en C1 à C3 substitué par un alcoxy en C1 à C3 ou un cycloalkyle en C3 à C6 ;R4 représente NO2 ; CN ; SO2NR6R7 ; NR9R10; COR11; OR12 ; un alkyle en C2 à C4 éventuellement substituépar OH, CN, un alcoxy en C1 à C4, NR6R7, CONR6R7 ou CO2R8 ; un alcényle en C2 à C4 éventuellementsubstitué par CN, CONR6R7 ou CO2R8 ; ou R4 représente un hétéréocyclyle de 5 à 7 chaînons éventuellementsubstitué par un ou plusieurs substituants choisis parmi OH, COOR8, CONH2, un alkyle en C1 à C6, un alcoxyen C1 à C4, un cycloalkyle en C3 à C6, un aryle, Het et un alkyle en C1 à C6 substitué par un halogène ou unalcoxy ou un hydroxyle ; ou R4 est un groupe monosaccharide à 5 ou 6 chaînons éventuellement substitué parun ou plusieurs substituants choisis parmi un alkyle en C1 à C6, un triméthylsilyle, un benzyle et un acétyle ;R5 représente H ; un alkyle en C1 à C6 ; un alcényle en C3 à C6 ; un cycloalkyle en C3 à C6 ; un alkyle en C1 àC4 éventuellement substitué par OH, un alcoxy en C1 à C4 ou NR6R7 ; un aryle ; ou Het ;R6 et R7 représentent chacun indépendamment H, OH, un alkyle en C1 à C6, un alcoxy en C1 à C6, un alcényleen C3 à C6, un cycloalkyle en C3 à C6, un adamantyle, un lactamyle en C3 à C8, un aryle, Het ou (CH2CH2O)jHoù j vaut de 1 à 3 ; ou R6 et R7 représentent chacun indépendamment un alkyle en C1 à C6 éventuellementsubstitué par OH, un alcoxy en C1 à C4, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, NR13R14, unaryle, Het ou un hétérocyclyle de 4 à 8 chaînons ; ou bien R6 et R7 représentent chacun indépendamment unhétérocyclyle de 4 à 8 chaînons éventuellement substitué par un plusieurs substituants choisis parmi OH,COOR8, CONH2, COR16, SO2R16, un alkyle en C1 à C6, un alcoxy en C1 à C4, un cycloalkyle en C3 à C6, unaryle, Het et un alkyle en C1 à C6 substitué par un halogène ou un alcoxy en C1 à C4 ou un hydroxyle ; ou R6

et R7 forment ensemble, avec l’atome d’azote auquel ils sont fixés, un hétérocyclyle de 4 à 8 chaînons éven-tuellement substitué par un ou plusieurs substituants choisis parmi OH, COOR8, CONH2, COR16, SO2R16, unalkyle en C1 à C6, (CH2CH2O)jH où j vaut de 1 à 3, un alcoxy en C1 à C4, un cycloalkyle en C3 à C6, un aryle,Het et un alkyle en C1 à C6 substitué par un halogène ou un alcoxy en C1 à C4 ou un hydroxyle ou un aryle ;ou R6 et R7 forment ensemble, avec l’atome d’azote auquel ils sont fixés, un groupe glucosylamino, un résiduacide aminé, un résidu ester d’acide aminé ou un résidu amide aminé, lesquels sont éventuellement substituéspar un ou plusieurs substituants choisis parmi un alkyle en C1 à C6, NR13R14, COR16, un benzyle, un benzy-loxycarbonyle et un t-butyloxycarbonyle ;R8 représente H, un alkyle en C1 à C6 ou un aryle ;R9 représente H, un alkyle en C1 à C6 ou SO2R16 ;R10 représente H ; un alkyle en C1 à C6; COR15 ; SO2NR6R7 ; SO2R16 ;

un groupe monosaccharide à 5 ou 6 chaînons éventuellement substitué par un ou plusieurs substituants choisisparmi un alkyle en C1 à C6, un triméthylsilyle, un benzyle et un acétyle ; ou R10 représente un hétérocyclyle à5 chaînons éventuellement substitué par un ou plusieurs substituants ; ou bien, lorsque R9 représente H, R10

représente un résidu acide aminé éventuellement substitué par un ou plusieurs substituants choisis parmi OH,un alkyle en C1 à C6, un alcoxy en C1 à C4, COR16, un benzyle, un benzyloxycarbonyle et un t-butyloxycarbonyle ;R11 représente H ; OH ; un alkyle en C1 à C6 ; un aryle ; Het ; NH(CH2)kNH2, NH(CH2)kNHSO2R16 ouNH(CH2)kNHCOR16, où k vaut de 0 à 4 ; un alkyle en C1 à C3 éventuellement substitué par un halogène, OHou un alcoxy en C1 à C6 ; ou (CH2)mNR6R7, où m vaut de 0 à 2 ; ou R11 est un résidu acide aminé ou un résiduamide aminé éventuellement substitué par un alkyle en C1 à C6 ou un alcoxy en C1 à C4 ;

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R12 représente H, COR19, SO2R16 ou un groupe monosaccharide à 5 ou 6 chaînons éventuellement substituépar un ou plusieurs substituants choisis parmi un alkyle en C1 à C6, un triméthylsilyle, un benzyle et COR16 ;R13 et R14 représentent chacun indépendamment H ou un alkyle en C1 à C6 ; ou bien R13 et R14 formentensemble, avec l’atome d’azote auquel ils sont fixés, un hétérocyclyle de 4 à 8 chaînons éventuellement substituépar un ou plusieurs substituants choisis parmi OH, un alkyle en C1 à C6, un alcoxy en C1 à C4, un cycloalkyleen C3 à C6, un aryle et Het ;R15 représente H ; CF3 ; un alkyle en C1 à C6 éventuellement substitué par un halogène, OH, un alcoxycarbo-nylamino en C1 à C6, NR13R14, NHSO2R16, NHCOR16, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2,un aryle ou Het ; (CH2)nCOOR8, ou (CH2)nCONHR8, où n vaut de 0 à 6 ; un alcényle en C2 à C4 éventuellementsubstitué par un alkyle en C1 à C6, OH, un alcoxy en C1 à C6 ou NR13R14 ; un cycloalkyle en C3 à C6 éven-tuellement substitué par un alkyle en C1 à C6 ou OH ; un cycloalcoxy éventuellement substitué par un alkyleen C1 à C6 ou OH ; un aryle ; ou Het ;R16 représente un alkyle en C1 à C6, un aryle ou Het ;R11 et R18 représentent chacun indépendamment H ; un alkyle en C1 à C6 éventuellement substitué par OH,SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, NR13R14, un aryle, Het ou un hétérocyclyle de 4 à 8chaînons ; un cycloalkyle en C3 à C6 ; ou un aryle éventuellement substitué par OH ; ou bien R17 et R18 formentensemble, avec l’atome d’azote auquel ils sont fixés, un hétérocyclyle de 4 à 8 chaînons éventuellement substituépar un ou plusieurs substituants choisis parmi OH, un alkyle en C1 à C6, un alcoxy en C1 à C4, un cycloalkyleen C3 à C6, un aryle et Het ;R19 représente un alkyle en C1 à C6, un aryle ou NHR8 ;R20 représente un alkyle en C1 à C3 ;l’halogène est F, Cl, Br ou I ;Y représente O, S ou NR8 ;ledit « aryle » est un phényle non substitué ou substitué par un ou plusieurs substituants choisis parmi unhalogène, un alkyle en C1 à C3, un alcoxy en C1 à C3, CF3, CN et NO2 ;lesdits « hétérocyclyle de 5 à 7 chaînons », « hétérocyclyle de 4 à 8 chaînons » et « hétérocyclyle à 5 chaînons »représentent un hétérocyclyle saturé ou insaturé comprenant un ou plusieurs hétéroatomes choisis parmi N,S et O ;ledit « Het » est un hétérocyclyle aromatique de 5 à 6 chaînons comprenant de 1 à 4 hétéroatomes choisisparmi N, S et O, ledit hétérocyclyle aromatique de 5 à 6 chaînons étant éventuellement substitué par un ouplusieurs substituants choisis parmi un halogène, un alkyle en C1 à C3, un alcoxy en C1 à C3, CF3, CN et NO2.

2. Composé de formule I, sels ou solvates pharmaceutiquement acceptables de celui-ci selon la revendication 1, oùR1 et R2 représentent chacun indépendamment H ; un alkyle en C1 à C10 ; un halogène ; CF3 ; OR5 ; NHCOR8 ;un aryle ; ou un alkyle en C1 à C4 éventuellement substitué par un aryle ou OR5 ;Z représente OR3 ;R3 représente un alkyle en C1 à C6 ou un alkyle en C1 à C3 éventuellement substitué par un alcoxy en C1 à C3 ;R4 représente NO2 ; CN ; SO2NR6R7 ; NR9R10; COR11 ; OR12; un alkyle en C2 à C4 éventuellement substitué parOH, un alcoxy en C1 à C4 ou NR6R7 ; ou R4 est un hétéréocyclyle à 5 ou 6 chaînons éventuellement substitué parun ou plusieurs substituants choisis parmi OH, COOR8, CONH2, un alkyle en C1 à C6, un alcoxy en C1 à C4, uncycloalkyle en C3 à C6, un aryle, Het et un alkyle en C1 à C6 substitué par OH ; ou R4 est un groupe monosaccharideà 5 ou 6 chaînons éventuellement substitué par un ou plusieurs substituants choisis parmi un alkyle en C1 à C6, untriméthylsilyle, un benzyle et un acétyle ;R5 représente H ; un alkyle en C1 à C6 ; un alkyle en C1 à C4 éventuellement substitué par OH, un alcoxy en C1 àC4 ou NR6R7 ; ou un aryle ;R6 et R7 représentent chacun indépendamment H, OH, un alkyle en C1 à C6, un alcoxy en C1 à C6, un alcényle enC3 à C6, un cycloalkyle en C3 à C6, un adamantyle, un lactamyle en C3 à C8, un aryle, Het ou (CH2CH2O)jH où jvaut de 1 à 3 ; ou R6 et R7 représentent chacun indépendamment un alkyle en C1 à C6 éventuellement substituépar OH, un alcoxy en C1 à C4, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, NR13R14, un aryle, Het ou unhétérocyclyle de 4 à 8 chaînons ; ou bien R6 et R7 représentent chacun indépendamment un hétérocyclyle de 4 à8 chaînons, ledit hétérocyclyle de 4 à 8 chaînons étant un furyle, thiényle, thiazolyle, imidazolyle, pyrazolyle, pyridyle,pyrimidinyle, pyrazinyle, morpholinyle, thiomorpholinyle, pipéridyle, pyrrolidinyle ou pipérazinyle, et ledit hétérocy-clyle de 4 à 8 chaînons étant éventuellement substitué par un plusieurs substituants choisis parmi OH, COOR8,CONH2, COR16, SO2R16, un alkyle en C1 à C6, un cycloalkyle en C3 à C6, un aryle, Het et un alkyle en C1 à C6substitué par un alcoxy en C1 à C4 ou un hydroxyle ; ou R6 et R7 forment ensemble, avec l’atome d’azote auquelils sont fixés, un hétérocyclyle de 4 à 8 chaînons éventuellement substitué par un ou plusieurs substituants choisisparmi OH, COOR8, CONH2, COR16, SO2R16, un alkyle en C1 à C6, (CH2CH2O)jH où j vaut de 1 à 3, un cycloalkyleen C3 à C6, un aryle, Het et un alkyle en C1 à C6 substitué par un alcoxy en C1 à C4 ou un hydroxyle ou un aryle ;

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ou R6 et R7 forment ensemble, avec l’atome d’azote auquel ils sont fixés, un groupe glucosylamino, un résidu acideaminé, un résidu ester d’acide aminé ou un résidu amide aminé, lesquels sont éventuellement substitués par unou plusieurs substituants choisis parmi un alkyle en C1 à C6, NR13R14, COR16, un benzyle, un benzyloxycarbonyleet un t-butyloxycarbonyle ;R8 représente H, un alkyle en C1 à C6 ou un aryle ;R9 représente H, un alkyle en C1 à C6 ou SO2R16 ;R10 représente H ; un alkyle en C1 à C6 ; COR15 ; SO2R16 ;

un groupe monosaccharide à 5 ou 6 chaînons ; ou R10 est un dihydroimidazolyle substitué par un hydroxyalkyle,ou un 1,2,4-triazolyle éventuellement substitué par un alkyle en C1 à C6, un aryle ou un groupe amino ; ou bien,lorsque R9 représente H, R10 représente un résidu acide aminé éventuellement substitué par un ou plusieurssubstituants choisis parmi OH, un alkyle en C1 à C6, un alcoxy en C1 à C4, COR16, un benzyle, un benzyloxycarbonyleet un t-butyloxycarbonyle ;R11 représente H ; OH ; un alkyle en C1 à C6 ; un aryle ; Het ; NH(CH2)kNH2, NH(CH2)kNHSO2R16 ouNH(CH2)kNHCOR16, où k vaut de 0 à 4 ; un alkyle en C1 à C3 substitué par un halogène, OH ou un alcoxy en C1à C6 ; ou (CH2)mNR6R7, où m vaut de 0 à 2 ; ou R11 est un résidu acide aminé ou un résidu amide aminé éventuel-lement substitué par un alcoxy en C1 à C4 ;R12 représente H, COR19, SO2R16 ou un groupe monosaccharide à 5 ou 6 chaînons ;R13 et R14 représentent chacun indépendamment H ou un alkyle en C1 à C6 ; ou bien R13 et R14 forment ensemble,avec l’atome d’azote auquel ils sont fixés, un hétérocyclyle de 4 à 8 chaînons éventuellement substitué par un ouplusieurs substituants choisis parmi OH et un alkyle en C1 à C6 ;R15 représente H ; CF3 ; un alkyle en C1 à C6 éventuellement substitué par un halogène, OH, un alcoxycarbonylaminoen C1 à C6, NR13R14, NHSO2R16, NHCOR16, SO3H, SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, un aryle ou Hét ;(CH2)nCOOR8, ou (CH2)nCONHR8, où n vaut de 0 à 6 ; un alcényle en C2 à C4 éventuellement substitué par unalkyle en C1 à C6, OH, un alcoxy en C1 à C6 ou NR13R14 ; un cycloalkyle en C3 à C6 éventuellement substitué parun alkyle en C1 à C6 ou OH ; un cycloalkyle en C3 à C6 éventuellement substitué par un alkyle en C1 à C6 ou OH ;un aryle ; ou Het ;R16 représente un alkyle en C1 à C6 ou un aryle ;R17 et R18 représentent chacun indépendamment H ; un alkyle en C1 à C6 éventuellement substitué par OH, SO3H,SO2NR13R14, SO2R16, PO(OH)2, PO(OR16)2, NR13R14, un aryle, Het ou un hétérocyclyle de 4 à 8 chaînons ; uncycloalkyle en C3 à C6 ; ou un aryle éventuellement substitué par OH ; ou bien R17 et R18 forment ensemble, avecl’atome d’azote auquel ils sont fixés, un hétérocyclyle de 4 à 8 chaînons éventuellement substitué par un ou plusieurssubstituants choisis parmi OH et un alkyle en C1 à C6 ;R19 représente un alkyle en C1 à C6, un aryle ou NHR8 ;R20 représente un alkyle en C1 à C3 ;l’halogène est F, CI, Br ou I ;Y représente O, S ou NR8 ;ledit « aryle » est un phényle non substitué ou substitué par un ou plusieurs substituants choisis parmi un halogène,un alkyle en C1 à C3 et un alcoxy en C1 à C3 ;lesdits « hétérocyclyle à 5 ou 6 chaînons », « hétérocyclyle de 4 à 8 chaînons » et « hétérocyclyle à 5 chaînons »représentent un hétérocyclyle saturé ou insaturé comprenant un ou plusieurs hétéroatomes choisis parmi N, S et O ;ledit « Het » est un hétérocyclyle aromatique à 5 ou 6 chaînons comprenant de 1 à 4 hétéroatomes choisis parmiN, S et O, ledit hétérocyclyle aromatique à 5 ou 6 chaînons étant éventuellement substitué par un ou plusieurssubstituants choisis parmi un halogène, un alkyle en C1 à C3, un alcoxy en C1 à C3, CF3, CN et NO2.ledit « acide aminé » est la glycine, alanine, phénylalanine, sérine, tryptophane, valine, leucine, isoleucine, t-leucine,tyrosine, lysine, histidine, méthionine, arginine, thréonine, aspartate, cystéine, proline, acide glutamique, asparagine,glutamine, ornithine ou citrulline ;ledit « monosaccharide à 5 ou 6 chaînons » est le ribose, désoxyribose, xylose, arabinose, glucose, mannose,galactose ou fructose.

3. Composé de formule I, sels ou solvates pharmaceutiquement acceptables de celui-ci :

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où

R1 représente H, F, CI, Br, I, OH, un méthyle, éthyle, propyle, isopropyle ou acétamido ;R2 représente Br, CF3, OR5, un éthyle, propyle, isopropyle, benzylamino, phényle, isobutyle, n-octyle ouacétamido ;Z représente OR3 ;R3 représente un éthyle, propyle, n-butyle, n-hexyle ou 3-méthoxypropyle ;R4 représente NO2, SO2NR6R7, NR9R10, COR11, OR12 ou un glucosyle ; ou R4 est un hétérocyclyle à 5 ou 6chaînons, ledit hétérocyclyle à 5 ou 6 chaînons étant un thiényle, thiazolyle, 1,2,4-triazolyle, imidazolyle, pyr-rolyle, oxadiazolyle, pyrimidinyle, morpholinyle, thiomorpholinyle, pipéridyle, pyrrolidinyle ou pipérazinyle, etledit hétérocyclyle à 5 ou 6 chaînons étant éventuellement substitué par un plusieurs substituants choisis parmiOH, COOH, CONH2, un alkyle en C1 à C6, un alcoxy en C1 à C4, un cycloalkyle en C3 à C6, un aryle, Het etun alkyle en C1 à C6 substitué par OH ;R5 représente H ; un alkyle en C1 à C4 éventuellement substitué par OH, un alcoxy en C1 à C4 ou NR6R7 ; ouun aryle ;R6 et R7 représentent chacun indépendamment H, un méthyle, méthoxyle, cyclopropyle, propényle, isobutyle,t-butyle, adamantyle, cyclohexyle, caprolactamyle, 2-(1-méthylpyrrol-2-yl)éthylamino, pyridylméthyle, thiényl-méthyle,

ou un alkyle en C2 à C3 éventuellement substitué par OH, NR13R14, SO3H, SO2NR13R14 ou un hétérocyclylede 5 à 6 chaînons, ledit hétérocyclyle de 5 à 6 chaînons étant un morpholinyle, thiomorpholinyle, pipéridyle,pyrrolidinyle ou pipérazinyle, et ledit hétérocyclyle de 5 à 6 chaînons étant éventuellement substitué par unplusieurs substituants choisis parmi OH, COOR8, CONH2, COR16, SO2R16, un alkyle en C1 à C6 et un aryle ;ou bien R6 et R7 forment ensemble, avec l’atome d’azote auquel ils sont fixés, un hétérocyclyle de 5 à 6 chaînons,ledit hétérocyclyle de 5 à 6 chaînons étant un morpholinyle, thiomor-pholinyle, pipéridyle, pyrrolidinyle ou pipé-razinyle, et ledit hétérocyclyle de 5 à 6 chaînons étant éventuellement substitué par un plusieurs substituantschoisis parmi OH, COOR8, CONH2, COR16, SO2R16, un alkyle en C1 à C6, (CH2CH2O)jH où j vaut de 1 à 2,un dichlorophényle, un benzyle, un pyridyle et un aryle ; ou bien NR6R7 est un groupe glucosylamino, un résiduacide aminé, un résidu ester d’acide aminé ou un résidu amide aminé, lesquels sont éventuellement substituéspar un ou plusieurs substituants choisis parmi NR13R14 et un acétyle ;R8 représente H, un méthyle ou un éthyle ;R9 représente H, un méthyle ou SO2R16 ;R10 représente H, un méthyle, COR15, SO2R16 ;

un glucosyle ou un mannosyle ; un dihydroimidazolyle substitué par un hydroxyéthyle ; ou bien, lorsque R9

représente H, R10 représente un résidu acide aminé éventuellement substitué par un ou plusieurs substituantschoisis parmi OH, un t-butyloxycarbonyle et un acétyle ;R11 représente OH ; un pyrazolyle substitué par un isopropyle ; un résidu acide aminé ; un résidu ester aminé ;

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NR6R7 ; CH2Br ou CH2NR6R7 ;R12 représente H, COR19, SO2R16, un mannosyle ou un glucosyle ;R13 et R14 représentent chacun indépendamment H ou un éthyle ; ou bien R13 et R14 forment ensemble, avecl’atome d’azote auquel ils sont fixés, un hétérocyclyle de 5 à 6 chaînons, ledit hétérocyclyle de 5 à 6 chaînonsétant un morpholinyle, pipéridyle, pyrrolidinyle ou pipérazinyle, et ledit hétérocyclyle de 5 à 6 chaînons étantéventuellement substitué par un plusieurs substituants choisis parmi OH et un alkyle en C1 à C6 ;R15 représente H ; un méthyle ; un éthyle ; un cyclohexyle ; CF3 ; (CH2)nCOOR8 ou (CH2)nCONH2 où n vaut0 ou 1 ; un vinyle ; un propényle ; un pyridyle ; un phényle substitué par un éthoxy ; ou un thiazolyle substituépar un isopropyle ;R16 représente un méthyle ;R17 et R18 représentent chacun indépendamment H, un éthyle ou un phényle ; ou bien R17 et R18 formentensemble, avec l’atome d’azote auquel ils sont fixés, un hétérocyclyle de 4 à 8 chaînons, ledit hétérocyclyle de4 à 8 chaînons étant un morpholinyle, pipéridyle, pyrrolidinyle ou pipérazinyle, et ledit hétérocyclyle de 4 à 8chaînons étant éventuellement substitué par un ou plusieurs substituants choisis parmi OH et un alkyle en C1à C6 ; ou bien lorsque Y représente NH, R17 et C(Y)N forment un dihydroimidazolyle ;R19 représente un méthyle ou NHC2H5 ;R20 représente un méthyle ;l’halogène est F, CI, Br ou I ;Y représente O, S, NH ou NC2H5;ledit « aryle » est un phényle non substitué ou substitué par un ou plusieurs substituants choisis parmi unhalogène, un alkyle en C1 à C3 et un alcoxy en C1 à C3 ;ledit « Het » est un hétérocyclyle aromatique de 5 à 6 chaînons comprenant de 1 à 4 hétéroatomes choisisparmi N, S et O, ledit hétérocyclyle aromatique de 5 à 6 chaînons étant éventuellement substitué par un ouplusieurs substituants choisis parmi un halogène, un alkyle en C1 à C3, un alcoxy en C1 à C3, CF3, CN et NO2 ;ledit « acide aminé » est la glycine, alanine, phénylalanine, sérine, tryptophane, valine, leucine, isoleucine, t-leucine, tyrosine, lysine, histidine, méthionine, arginine, thréonine, aspartate, cystéine, proline, acide glutamique,asparagine, glutamine, ornithine ou citrulline ;ledit « monosaccharide à 5 ou 6 chaînons » étant le glucose ou le mannose.

4. Composé de formule I, sels ou solvates pharmaceutiquement acceptables de celui-ci selon la revendication 1, leditcomposé phénylpyrimidone étant choisi parmi :

6-isopropyl-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,6-éthyl-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,6-acétamido-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,6-isopropyl-2-[2-éthoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-[2-éthoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-chloro-6-isopropyl-2-[2-éthoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-acétamido-6-isopropyl-2-[2-éthoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-[2-n-butoxy-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-bromo-6-n-octyl-2-[2-éthoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-bromo-6-phényl-2-[2-éthoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-méthyl-6-isopropyl-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-fluoro-6-éthyl-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-méthyl-6-éthyl-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-hydroxy-6-isopropyl-2-[2-éthoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-[2-n-hexyloxy-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-bromo-6-isobutyl-2-[2-éthoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-{2-n-propoxyl-5-[N-méthyl-N-(2-hydroxyéthyl)aminosulfonyl]phényl}pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-{2-n-propoxyl-5-[N-(2-morpholinoéthyl)aminosulfonyl]phényl}pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-{2-n-propoxyl-5-[N-(3-morpholinopropyl)aminosulfonyl]phényl}pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-{2-n-propoxyl-5-[N-(N’,N’-diéthylamino)éthylaminosulfonyl]phényl}pyrimid-4(3H)-one,5,6-diéthyl-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5,6-diéthyl-2-{2-n-propoxyl-5-[N-méthyl-N-(hydroxyéthyl)aminosulfonyl]phényl}pyrimid-4(3H)-one,5,6-diéthyl-2-{2-n-propoxyl-5-[N-(2-éthylaminoéthyl)aminosulfonyl]phényl}pyrimid-4(3H)-one,N-(3-(4,5-diéthy)-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphénylsulfonylproline,2-(5-nitro-2-n-propoxyphényl)-5-bromo-6-isopropylpyrimid-4(3H)-one,

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2-(5-amino-2-n-propoxyphényl)-5-bromo-6-isopropylpyrimid-4(3H)-one,1-(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-3-éthylthiourée,1-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl]-3-éthyl-2-méthylisothiourée,N-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl]-N’,N"-triéthylguanidine,N-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl]-N’-éthyl-pipéridyl-1-formami-dine,N-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl]-N’-éthyl-pyrrolyl-1-formamidi-ne,2-{2-[3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl]amino-4,5-dihydroimidazol-1-yl}éthanol,2-(5-nitro-2-n-propoxyphényl)-5,6-diéthylpyrimid-4-(3H)-one,2-(5-amino-2-n-propoxyphényl)-5,6-diéthylpyrimid-4-(3H)-one,1-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-3-éthylthiourée,1-[3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl]-3-éthyl-2-méthylisothiourée,N-[3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl]-N’-éthylpipéridyl-1-formamidine,N-[3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl]-N’,N"-triéthylguanidine,2-{2-[3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl]amino-4,5-dihydroimidazol-1-yl}étha-nol,N-[3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl]-N’-éthyl-pyrrolyl-1-formamide,N-[3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl]-pyrrolyl-1-formamidine,5-bromo-6-isopropyl-2-(2-n-propoxyl-5-mésylamidophényl)pyrimid-4-(3H)-one,5,6-diéthyl-2-(2-n-propoxyl-5-mésylamidophényl)pyrimid-4-(3H)-one,N-(3-(1,6-dihydro-4-isopropyl-5-bromo-6-oxopyrimidin-2-yl)-4-propoxyphényl)acétamide,N-(3-(1,6-dihydro-4,5-diéthyl-6-oxopyrimidin-2-yl)-4-propoxyphényl)acétamide,N-(3-(1,6-dihydro-4,5-diéthyl-6-oxopyrimidin-2-yl)-4-propoxyphényl)propionamide,N-(3-(1,6-dihydro-4,5-diéthyl-6-oxopyrimidin-2-yl)-4-propoxyphényl)cyclohexamide,N-(3-(1,6-dihydro-4,5-diéthyl-6-oxopyrimidin-2-yl)-4-propoxyphényl)formamide,N-(3-(1,6-dihydro-4,5-diéthyl-6-oxopyrimidin-2-yl)-4-propoxyphényl)-1-t-butyloxycarbonyl-4-hydroxyprolylami-de,acide 4-n-propoxyl-3-(1,6-dihydro-4,5-diéthyl-6-oxopyrimidin-2-yl)benzoïque,(morpholin-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophénone,(pipérid-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophénone,(2-aminoformylpyrrol-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophénone,acide 4-n-propoxyl-3-(1,6-dihydro-4-isopropyl-6-oxopyrimidin-2-yl)benzoïque,(morpholin-1-yl)(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophénone,(pipérid-1-yl)(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophénone,(4-méthylpipérazin-1-yl)(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophéno-ne,2-(5-(N,N-diméthylamino-2-n-propoxyphényl)-5,6-diéthylpyrimid-4(3H)-one,1-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)urée,1-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-3-éthylurée,1-(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-3-phénylthiourée,1-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)guanidine, 5-bromo-6-isopropyl-2-(5-(2-bromoacétyl)-2-n-propoxyphényl)pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-(5-(2-morpholinylacétyl)-2-n-propoxyphényl)pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-(5-(2-(4-méthylpipérazin-1-yl)acétyl)-2-n-propoxyphényl)pyrimid-4(3H)-one,5,6-diéthyl-2-(5-(2-bromoacétyl)-2-n-propoxyphényl)pyrimid-4(3H)-one,5,6-diéthyl-2-(5-(2-(4-méthylpipérazin-1-yl)acétyl)-2-n-propoxyphényl)pyrimid-4(3H)-one,5,6-diéthyl-2-(5-(2-morpholinylacétyl)-2-n-propoxyphényl)pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-(2-n-propoxyl-5-(tétrahydro-3,4,5-trihydroxy-6-(hydroxyméthyl)-2H-pyran-2-ylami-no)phényl)pyrimid-4(3H)-one,5-bromo-6-isopropyl-2-(2-n-propoxyl-5-(tétrahydro-3,4-dihydroxy-5-(1,2-dihydroxyéthyl)fur-2-ylamino)phé-nyl)pyrimid-4(3H)-one,5,6-diéthyl-2-(2-n-propoxyl-5-(tétrahydro-3,4-dihydroxy-5-(1,2-dihydroxyéthyl)fur-2-ylamino)phényl)pyrimid-4(3H)-one,5,6-diéthyl-2-(2-n-propoxyl-5-(tétrahydro-3,4,5-trihydroxy-6-(hydroxyméthyl)-2H-pyran-2-ylamino)phényl)pyri-mid-4(3H)-one,2-(5-hydroxy-2-n-propoxyphényl)-5,6-diéthylpyrimid-4(3H)-one,

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acétate de 3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényle,éthylaminoformiate de 3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényle,5,6-diéthyl-2-(2-n-propoxyl-5-(tétrahydro-3,4,5-trihydroxy-6-(hydroxyméthyl)-2H-pyran-2-yloxy)phényl)pyri-mid-4(3H)-one,mésylate de 3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényle,2-(5-(2,5-diméthyl-1H-pyrrol-1-yl)-2-propoxyphényl)-5,6-diéthylpyrimid-4(3H)-one,2,2’-(4-n-propoxyl-1,3-phénylène)bis(5,6-diéthylpyrimid-4(3H)-one),2-(5-(1,3,4-oxadiazol-2-yl)-2-propoxyphényl)-5,6-diéthylpyrimid-4(3H)-one,2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)acétate d’éthyle,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-morpholinyléthyl)-4-n-propoxybenzamide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N,N-di(2-hydroxyéthyl)-4-n-propoxybenzamide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-caprolactam-3-yl)-4-n-propoxybenzamide,(4-(2,3-dichlorophényl)pipérazin-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophé-none,(3-isopropylpyrazol-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophénone,N-cyclohexyl-3-(4, 5-d iéthyl-1,6-d ihyd ro-6-oxopyrimid in-2-yl)-4-n-propoxybenzamide,N-((pyrid-2-yl)méthyl)-3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,2-(3-(4,5-diéthy)-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3,3-diméthylbutyrate de méthyle,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-2,2,2-trifluoroacétamide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)aminoformylformiate d’éthyle,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)acrylamide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-2-crotonamide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)aminoformylacétate d’éthyle,2-éthoxyl-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)benzamide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)nicotinamide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-5-isopropylthiazolyl-2-formamide,3-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)aminoformyl)propylaminoformiate det-butyle,4-acétamido-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)butyramide,1-acétyl-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)pyrrolidinyl-2-formamide,2-acétamido-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-3-méthylbutyramide,2-acétamido-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-3-phénylpropionamide,2-acétamido-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)propionamide,2,6-diacétamido-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)hexanamide,N1-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)propanediamide,N1-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)oxalamide,N-(aminoformylméthyl)-3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,5,6-diéthyl-2-{2-n-propoxyl-5-[2-(1-méthylpyrrol-2-yl)éthyl)aminosulfonyl]phényl}pyrimid-4(3H)-one,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-(1-méthylpyrrol-2-yl)éthyl)-4-n-propoxylbenzamide,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)amino-5-uréepenta-noïque,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)amino-5-aminopenta-noïque,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)amino-3-méthylbutyri-que,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)aminopropanoïque,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)amino-3-hydroxy-propanoïque,2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)aminopropionate d’éthyle,acide 3-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)aminopropylsulfoni-que,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)aminoéthylsulfonique,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)amino-3-aminoformyl-propanoïque,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)amino-3-indolepropio-nique,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)aminoacétique,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)amino-3,3-diméthylbu-

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tyrique,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)amino-4-aminoformyl-butyrique,2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)sulfonyl)amino-3-méthylvalérated’éthyle,2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphénylsulfonamido)-6-acétamidocaproate deméthyle,5,6-diéthyl-2-(2-n-propoxyl-5-(4-hydroxyéthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5,6-diéthyl-2-(2-n-propoxyl-5-(3-hydroxypropylaminosulfonyl)phényl]pyrimid-4(3H)-one,5,6-diéthyl-2-(2-n-propoxyl-5-(N-(2-morpholinyléthyl)-N-(2-hydroxyéthyl)aminosulfonyl)phényl)pyrimid-4(3H)-one,5,6-diéthyl-2-(2-n-propoxyl-5-(N-méthyl-N-(2-(pyrrolidin-1-yl)éthyl)laminosulfonyl)phényl)pyrimid-4(3H)-one,5,6-diéthyl-2-(2-n-propoxyl-5-(2-(N,N-diéthyl)aminoéthylaminosulfonyl)phényl] pyrimid-4(3H)-one maléate,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phénylpropanoïque,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzoylprolinate de méthyle,2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-(4-hydroxyphényl)propionate deméthyle,2-3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-(1 H-indol-3-yl)propionate d’éthy-le,2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-méthylbutyrate de méthyle,2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-(1 H-imidazol-4-yl)propionate deméthyle,2-3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-méthylvalérate d’éthyle,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propionique,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-aminoformylpropionique,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-4-aminoformylbutyrique,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-hydroxypropionique,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-guanidinopentanoïque,2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phényl propionate de méthyle,2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido) propionate de méthyle,2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-4-méthylvalérate de méthyle,2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido) propionate d’éthyle,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-(4-méthylpipérazin-1-yl)-1-oxopropan-2-yl)-4-n-propoxy-benzamide,N-(1-aminoformyléthyl)-3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl-N-(2-(thién-2-yl)éthyl)benzamide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl-N-((fur-2-yl)méthyl)benzamide,N-t-butyl-3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-isobutyl-4-n-propoxylbenzamide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-allyl-4-n-propoxylbenzamide,(4-(pyrid-2-yl)pipérazin-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophénone,(4-(hydroxyéthyloxyéthyl)pipérazin-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylben-zophénone,(4-(hydroxyéthyl)pipérazin-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophénone,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(3-hydroxypropyl)-4-n-propoxylbenzamide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-hydroxy-2-propyl)-4-n-propoxybenzamide,N-éthyl-3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-hydroxyéthyl)-4-n-propoxylbenzamide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-diéthylaminoéthyl)-4-n-propoxylbenzamide,acide 3-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propyl-1-sulfonique,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)éthylsulfonique,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-hydroxyéthyl)-N-méthyl-4-n-propoxylbenzamide,(4-benzylpipérazin-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophénone,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-méthyl-N-(2-(pyrrolidin-1-yl)éthyl)-4-n-propoxybenzamide,5-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido) pipéridyl-2-formiate de méthyle,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-méthoxyl-N-méthyl-4-n-propoxybenzamide,5,6-diéthyl-2-[2-(3-méthoxyln-propoxyl)-5-(4-méthyl-1-pipérazinylsulfonyl) phényl]pyrimid-4(3H)-one,2-chloro-N-3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)acétamide,

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2-(diméthylamino)-N-3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)acétamide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-2-(4-méthylpipérazin-1-yl)acétamide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-2-morpholinyl)acétamide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-2-(pipérid-1-yl)acétamide,(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphénylaminoformyl) méthylphosphate de diméthy-le,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl) isobutyramide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-3-méthylbutyramide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-2-phénylacétamide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)benzamide,3-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphénylaminoformyl) propionate d’éthyle,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-5-oxopyrrolidinyl-2-formamide,2-acétamido-N-3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-4-méthylpentanamide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-2-acétamido-3-(1H-indol-3-yl)propiona-mide,2-acétamido-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)glutaramide,2-acétamido-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-3-hydroxybutyramide,2-acétamido-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-3-hydroxypropionamide,acétate de 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphénylaminoformyl)-2-acétamidoé-thyle,5,6-diéthyl-2-(5-(éthylamino)-2-n-propoxyphényl)pyrimid-4(3H)-one,N-éthyl-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)propionamide,(N-éthyl-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)aminoformylformiate d’éthyle,1,3-diéthyl-1-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)urée,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl) pipéridyl-1-formamide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-4-méthylpipérazinyl-1-formamide,1-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-3-propylurée,1-cyclohexyl-3-(3-(4, 5-d iéthyl-1,6-d ihyd ro-6-oxopyrim id in-2-yl)-4-n-propoxyphényl)urée,1,1-diéthyl-3-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)urée,1-(2-(diéthylamino)éthyl)-3-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)urée maléate,(4-méthylpipérazin-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophénone,5-iodo-6-isopropyl-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl) phényl]pyrimid-4(3H)-one,5-chloro-6-éthyl-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,5,6-diéthyl-2-(2-n-propoxyl-5-((tétrahydro-2,4,5-trihydroxy-6-(hydroxyméthyl)-2H-pyran-3-ylamino)sulfo-nyl)phényl]pyrimid-4(3H)-one,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-uréepentanoïque,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-aminopentanoïque,3-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(tétrahydro-2,4,5-trihydroxy-6-(hydroxyméthyl)-2H-pyran-3-yl)-4-n-propoxybenzamide,2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido) éthylsulfamide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-méthyl-pipérazin-1-yl sulfonyléthyl)-4-n-propoxybenzami-de,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diéthylaminosulfonyléthyl)-4-n-propoxybenzamide,3-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido) propylsulfamide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-méthyl-pipérazin-1-yl sulfonylpropyl)-4-n-propoxybenza-mide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diéthylaminosulfonypropyl)-4-n-propoxybenzamide,5,6-diéthyl-2-(5-(tétrahydro-3,4,5-trihydroxy-6-(hydroxyméthyl)-2H-pyran-2-yl)-2-n-propoxyphényl)pyrimid-4(3H)-one,5-iodo-6-éthyl-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl] pyrimid-4(3H)-one,5-bromo-6-éthyl-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,et5-chloro-6-isopropyl-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl] pyrimid-4(3H)-one.

5. Composé de formule I, sels ou solvates pharmaceutiquement acceptables de celui-ci selon l’une quelconque desrevendications 1 à 3, ledit composé phénylpyrimidone étant choisi parmi :

5,6-diéthyl-2-[2-n-propoxyl-5-(4-méthyl-1-pipérazinylsulfonyl)phényl]pyrimid-4(3H)-one,

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5,6-diéthyl-2-(2-n-propoxyl-5-[N-(2-morpholinyléthyl)aminosulfonyl)phényl} pyrimid-4(3H)-one,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl sulfonylproline,1-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-3-éthylthiourée,N-[3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl]-N’,N"-triéthylguanidine,N-[3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl]-pyrrolyl-1-formamide,5-bromo-6-isopropyl-2-(2-n-propoxyl-5-mésylamidophényl)pyrimid-4(3H)-one, 5,6-diéthyl-2-(2-n-propoxyl-5-mésylamidophényl)pyrimid-4(3H)-one,N-(3-(1,6-dihydro-4-isopropyl-5-bromo-6-oxopyrimidin-2-yl)-4-propoxyphényl)acétamide ,N-(3-(1,6-dihydro-4,5-diéthyl-6-oxopyrimidin-2-yl)-4-propoxyphényl)acétamide,N-(3-(1,6-dihydro-4,5-diéthyl-6-oxopyrimidin-2-yl)-4-propoxyphényl)propionamide,N-(3-(1,6-dihydro-4,5-diéthyl-6-oxopyrimidin-2-yl)-4-propoxyphényl) cyclohexamide,N-(3-(1,6-dihydro-4,5-diéthyl-6-oxopyrimidin-2-yl)-4-propoxyphényl)-1-t-butyloxycarbonyl-4-hydroxyprolyami-de,(morpholin-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl) benzophénone,(pipérid-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl) benzophénone,(2-aminoformylpyrrol-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophénone,(morpholin-1-yl)(3-(4-isopropyl-5-bromo-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyl)benzophénone,1-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)urée,1-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-3-éthylurée,5,6-diéthyl-2-(5-(2-morpholinylacétyl)-2-n-propoxyphényl)pyrimid-4(3H)-one, 2,2’-(4-n-propoxyl-1,3-phénylé-nyl)bis(5,6-diéthylpyrimid-4(3H)-one),2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)acétate d’éthyle,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-2,2,2-trifluoroacétamide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl) aminoformylacétate d’éthyle,4-acétamido-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)butyramide,1-acétyl-N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl) pyr-rolidinyl-2-formamide,2-acétam ido-N-(3-(4, 5-d iéthyl-1,6-d ihyd ro-6-oxopyrimid in-2-yl)-4-n-propoxyphényl)-3-phénylpropionamide,N1-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)oxalamide,5,6-diéthyl-2-{2-n-propoxyl-5-[(2-(1-méthylpyrrol-2-yl)éthyl)aminosulfonyl] phényl}pyrimid-4(3H)-one,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(2-(1-méthylpyrrol-2-yl)éthyl)-4-n-propoxylbenzamide,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl) sulfonyl)amino-5-uréepenta-noïque,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl) sulfonyl)amino-5-aminopenta-noïque,2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl) sulfonyl)aminopropionate d’éthyle,acide 3-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl) sulfonyl)aminopropylsulfoni-que,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl) sulfonyl)aminoéthylsulfonique,acide 2-(N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl) sulfonyl)amino-3-aminoformyl-propanoïque,5,6-diéthyl-2-(2-n-propoxyl-5-(4-hydroxyéthyl-1-pipérazinylsulfonyl)phényl] pyrimid-4(3H)-one,5,6-diéthyl-2-(2-n-propoxyl-5-(N-(2-morpholinyléthyl)-N-(2-hydroxyéthyl) aminosulfonyl)phényl)pyrimid-4(3H)-one,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phénylpropanoïque,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzoylprolinate de méthyle,2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido)-3-(4-hydroxyphényl)propionate deméthyle,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzamido) propanoïque,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-aminoformylpropanoïque,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-guanidinopentanoïque,acide méthyle 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-3-phénylpropanoï-que,acide méthyle 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)propanoïque,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-(4-méthylpipérazin-1-yl)-1-oxopropan-2-yl)-4-n-propoxy-benzamide,N-(1-aminoformyléthyl)-3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamide,(4-(hydroxyéthyoxyléthyl)pipérazin-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylben-zophénone,

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(4-(hydroxyéthyl)pipérazin-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophénone,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(1-hydroxy-2-propyl)-4-n-propoxybenzamide,acide 3-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido) propyl-1-sulfonique,5-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido) pipéridinyl-2-formiate de méthyle,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)-2-(4-méthylpipérazin-1-yl)acétamide,N-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphényl)benzamide,maléate de 1-(2-(diéthylamino)éthyl)-3-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxyphé-nyl)urée,(4-méthylpipéraziny-1-yl)(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxylbenzophénone,5,6-diéthyl-2-(2-n-propoxyl-5-((tétrahydro-2,4,5-trihydroxy-6-(hydroxyméthyl)-2H-pyran-3-ylamino)sulfo-nyl)phényl]pyrimid-4(3H)-one,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-uréepentanoïque,acide 2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido)-5-aminopentanoïque,3-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(tétrahydro-2,4,5-trihydroxy-6-(hydroxyméthyl)-2H-pyran-3-yl)-4-n-propoxybenzamide,2-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido) éthylsulfamide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-méthyl-pipérazin-1-yl sulfonyléthyl)-4-n-propoxybenzami-de,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N,N-diéthylaminosulfonyléthyl)-4-n-propoxybenzamide,3-(3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-4-n-propoxybenzamido) propylsulfamide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(4-méthyl-pipérazin-1-yl sulfonylpropyl)-4-n-propoxybenza-mide,3-(4,5-diéthyl-1,6-dihydro-6-oxopyrimidin-2-yl)-N-(N, N-diéthylaminosulfonylpropyl)-4-n-propoxybenzamide et5,6-diéthyl-2-(5-(tétrahydro-3,4,5-trihydroxy-6-(hydroxyméthyl)-2H-pyran-2-yl)-2-n-propoxyphényl)pyrimid-4(3H)-one.

6. Procédé de préparation du composé de formule I, sels ou solvates pharmaceutiquement acceptables de celui-ciconformément à la revendication 1, le procédé étant l’une des méthodes suivantes :

(1) lorsque R4 représente OH, SO2NR6R7, COR11, un alkyle en C2 à C4 substitué ou non substitué, un alcényleen C2 à C4 substitué ou non substitué, ou un hétérocyclyle de 5 à 7 chaînons substitué ou non substitué, lecomposé de formule I est préparé en cyclisant le composé de formule II avec le composé de formule III enprésence d’une base, R1, R2, R3, R6, R7, R11 et ledit hétérocyclyle de 5 à7 chaînons étant tels que définis dans la revendication 1 ;

ou,(2) le composé de formule I est préparé à partir du composé de formule la, du composé de formule le ou d’autrescomposés de formule I, R1, R2, R3, R5, R6, R7, R8, R9, R10, R12, R15, R16, R17, R18, R19 et R20 étant tels quedéfinis dans la revendication 1 ; où

1) lorsque R4 représente SO2NR6R7, le composé de formule Ib est préparé à partir du composé de formuleIa par chlorosulfonation puis par une réaction avec R6R7NH en présence d’une base ;

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ou,2) lorsque R4 représente NO2, le composé de formule Ic est préparé en nitrant le composé de formule la ;

ou,3) lorsque R4 représente NH2, le composé de formule Id est préparé en réduisant le composé de formule Ic

ou,4) lorsque R4 représente CN, le composé de formule If est préparé à partir du composé de formule le parsubstitution nucléophile avec du cyanure ;

ou,5) lorsque R4 représente COOH, le composé de formule Ig est préparé à partir du composé de formule Ifpar hydrolyse ;

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ou,6) lorsque R4 représente NR9R10, le composé de formule I est préparé à partir du composé de formule Iddans lequel R4 représente NH2, où

1> lorsque R9 et R10 représentent simultanément un méthyle, le composé de formule I est préparé parN-méthylation en utilisant un agent de méthylation ;2> lorsque R9 représente H et R10 représente SO2R16, le composé de formule I est préparé à partirdu composé de formule Id par sulfonylation en présence d’une base ;3> lorsque R9 représente H et R10 représente COR15, le composé de formule I est préparé en faisantréagir le composé de formule Id avec un dérivé chlorure d’acyle d’un acide organique, qui est obtenuen faisant réagir l’acide organique avec du chlorure d’oxalyle ou du chlorure de thionyle ; ou en con-densant le composé de formule Id avec un acide organique ;4> lorsque R9 représente H, R10 représente C(Y)NR17R18 et Y est O ou S, le composé de formule Iest préparé par une réaction d’addition du composé de formule Id avec le composé de formuleY=C=NR17R18;5> lorsque R9 représente H, R10 représente un groupe monosaccharide à 5 ou 6 chaînons, le composéde formule I est préparé en faisant réagir le composé de formule Id avec un monosaccharide à 5 ou 6chaînons dépourvu de groupe protecteur en présence d’une quantité trace d’un acide organique entant que catalyseur ;6> lorsque R9 représente H, R10 représente

et Y représente NR8, le composé de formule I est préparé par substitution nucléophile du composé deformule Ih avec un composé de formule R17NHR18, le composé de formule Ih étant préparé par réactiond’addition du composé de formule Ii avec du iodométhane, et le composé de formule Ii étant préparépar la réaction d’addition du composé de formule Id avec R8SCN ;

7> lorsque R9 représente H et R10 représente un résidu acide aminé substitué par un acétyle, conden-sation du composé de formule Id avec un acide aminé protégé par N-Boc en présence d’un agent decouplage et d’un activateur pour donner un intermédiaire, suivie par la déprotection du groupe Bocdans l’acide trifluoroacétique, et pour finir réaction avec de l’anhydride acétique dans de la pyridinepour donner le composé de formule I ;

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ou,7) lorsque R4 représente COR11 et R11 représente NR6R7, le composé de formule I est préparé en con-densant le composé de formule Ig avec R6R7NH; ou en transformant le composé de formule Ig en un dérivéchlorure d’acyle correspondant, puis en le faisant réagir avec R6R7NH ;ou,8) lorsque R4 représente COR11 et R11 représente CH2NR6R7, le composé de formule I est préparé encondensant le composé de formule Ij avec R6R7NH, le composé de formule Ij étant préparé en bromant lecomposé de formule Ik, et le composé de fomule Ik étant préparé en faisant réagir le composé de formulela avec un éther de vinyle et de n-butyle en présence d’un catalyseur métallique, puis en effectuant unehydrolyse ; ou le composé de formule Ij peut également être préparé en soumettant le composé la à uneréaction de Friedel-Crafts avec du bromure de bromoacétyle ;

ou,9) lorsque R4 représente OR12, le composé de formule I est préparé à partir du composé de formule II, où

1> lorsque R12 représente COR19 et R19 représente un aryle ou un alkyle en C1 à C6, le composé deformule I est préparé en estérifiant le composé de formule Il dans laquelle R4 représente OH ;2> lorsque R12 représente COR19 et R19 représente NHR8, le composé de formule I est préparé parréaction d’addition de R8NCO avec le composé de formule II dans laquelle R4 représente OH ;3> lorsque R12 représente SO2R16, le composé de formule I est préparé par sulfonylation du composéde formule II dans laquelle R4 représente OH ;4> lorsque R12 représente un groupe monosaccharide à 5 ou 6 chaînons, le composé de formule Inest préparé en condensant premièrement le composé de formule II avec un monosaccharide à 5 ou 6chaînons protégé par de l’hydroxyle activé par le trichloroacétonitrile pour produire le composé deformule Im, puis en effectuant une hydrolyse et une déprotection ;

ou,

10) lorsque R4 représente un pyrrolyle, le composé de formule Io est préparé en condensant de la 2,5-hexanedione avec le composé de formule Id, dans laquelle R4 représente NH2 ;

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ou,11) lorsque R4 représente un glycoside, le composé de formule I est préparé en faisant d’abord réagir lecomposé de formule le, dans laquelle R4 représente Br, avec n-BuLi, puis en faisant réagir avec un gluco-lactone protégé, puis en effectuant une réduction au moyen d’un agent réducteur ;

ou,(3) le composé de formule I est préparé en convertissant d’autres composés de formule I dans laquelle R1 estun substituant différent, R2, R3 et R4 étant tels que définis dans la revendication 1 ; où

1) lorsque R1 représente un halogène, le composé de formule Iq est préparé en halogénant le composéde formule Ip dans laquelle R1 représente H en présence d’une base organique ;

ou,2) lorsque R1 représente NH2, le composé de formule Is est préparé en hydrolysant le composé de formuleIr dans laquelle R1 représente un acétamido ;

7. Procédé de préparation de l’intermédiaire dans le procédé selon la revendication 6 ayant la formule ci-dessous

dans laquelle Z représente OR3, R3 et R4 étant tels que définis dans la revendication 6,

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le procédé comprenant les étapes suivantes :

le composé de formule III est préparé en faisant réagir le composé de formule IV avec du lithium bis(triméthyl-silyl)amide dans du tétrahydrofurane ;

ou,le composé de formule III est préparé en faisant premièrement réagir le composé de formule IV avec de l’hy-drochlorure d’hydroxylamine pour produire le composé de formule V, puis en effectuant une hydrogénation ;

8. Composition pharmaceutique comprenant une dose efficace sur le plan thérapeutique d’un ou plusieurs composéschoisis dans le groupe constitué des composés de formule I, des sels et solvates pharmaceutiquement acceptablesde ceux-ci selon l’une quelconque des revendications 1 à 5, et un ou plusieurs auxiliaires pharmaceutiquementacceptables.

9. Composition pharmaceutique selon la revendication 8, la dose dudit composé de formule I, sels ou solvates phar-maceutiquement acceptables de celui-ci allant de 1 à 500 mg par jour.

10. Utilisation d’un composé de formule I, sels ou solvates pharmaceutiquement acceptables de celui-ci selon l’unequelconque des revendications 1 à 5 pour préparer un médicament destiné à l’homme.

11. Utilisation d’un composé de formule I, sels ou solvates pharmaceutiquement acceptables de celui-ci selon l’unequelconque des revendications 1 à 5 pour préparer un médicament destiné à traiter ou prévenir la dysfonctionérectile masculine, l’hyperplasie bénigne de la prostate, les troubles sexuels chez la femme, l’accouchement pré-maturé, la ménorragie, l’obstruction du col de la vessie, l’incontinence, l’angor de Prinzmetal instable et variable,l’hypertension, l’hypertension pulmonaire, l’insuffisance cardiaque congestive, l’insuffisance rénale, l’athéroscléro-se, l’apoplexie, une maladie vasculaire périphérique, les maladies de Raynaud, des maladies inflammatoires, labronchite, l’asthme chronique, l’asthme allergique, la rhinite allergique, le glaucome ou des maladies caractériséespar un trouble de l’entérocinésie.

12. Composé de formule I, ses sels ou solvates pharmaceutiquement acceptables de celui-ci destinés à être utilisésconformément à la revendication 11, ledit composé de formule I, ses sels ou solvates pharmaceutiquement accep-tables étant utilisés en association avec un inhibiteur de la recapture de 5-HT, un bloquant du récepteur alpha, unmédicament antihypertensif, de la propionyl-L-carnitine, du undécanoate de testostérone ou de la Tianeptine.

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REFERENCES CITED IN THE DESCRIPTION

This list of references cited by the applicant is for the reader’s convenience only. It does not form part of the Europeanpatent document. Even though great care has been taken in compiling the references, errors or omissions cannot beexcluded and the EPO disclaims all liability in this regard.

Patent documents cited in the description

• WO 9428902 A [0002]• WO 9849166 A [0003]• WO 9954333 A [0003]• WO 0187888 A [0003]• WO 2004096810 A [0003]• WO 2004108726 A [0003]• WO 2004101567 A [0003]• WO 2006126081 A [0003]• WO 2006126083 A [0003]

• WO 2007020521 A [0003]• CA 02339677 [0003]• WO 2005089752 A [0003]• WO 2005012303 A [0003]• WO 2007002125 A [0003]• WO 03020724 A [0003]• WO 2007056955 A [0003]• US 4031093 A [0033]

Non-patent literature cited in the description

• SCHMIDT et al. Angew. Chem., 1980, vol. 92,763-764 [0030] [0032]

• UPRETI, M. et al. Tetrahedron, 2000, vol. 56, 6577[0204]

• Thrombosis Res., 1991, vol. 62, 31 [0281]• J. Biol. Chem., 1997, vol. 272, 2714 [0281]