5271 5275.output

* GB785678 (A)

Description: GB785678 (A) ? 1957-10-30

Improvements in or relating to riveting machines

Description of GB785678 (A)

PATENT SPECIFICATION 785,678 Date of Application and filing Complete Specification Jan 19, 1956. No 1 851156. Application made in Switzerland on May 25, 1955. Complete Speciflication Published Oct 30, 1957. Index at Acceptance:-Classes 35, A 1 82 (A: J: K); 83 ( 4), H 4 N, UI(C: F: J K: N), U 2 (A: D: J); and 124, C( 1 A 2: 4 X: 5 A 5: 9 D: 19). International Classification: -023 j H 02 k. CO Ml KPLETE SPECIFICATION Improvements in or relating to Riveting Machines Wle, _d AG A G, a Swiss body corporate of 14, L _giao n, Zuich, Switzerland, do licieby declare 'he invention, for which we pray that a patent may be granted to us, and the method oy which it is to be performed, to be particularly described in and by the following statement: - The invention relates to a riveting machine and aims to provide an improved machine of dtis kind having a higher efficiency and which is easier to operate than known machines and the electric control elements of which are well protected from vibrations inherent in a riveting machine. According to the invention, the riveting machine comprises a riveting tool which can be rotated by a motor and vibrated by an electro magnetic vibrator, and electric control means for varying the amplitude and period of the vibrations of the vibrator, the motor, vibrator and tool being mounted as a unit for sliding movement in a housing relatively to a worktable. An example of the invention is described with reference to the accompanying drawings in which:Fig 1 is a perspective view of a riveting machine according to the invention, Fig 2 is a sectional side

elevation of the machine taken along the lines II-II in Fig 1, Fig 3 is g sectional elevation along the lines III-III in Fig 2 Fig 4 is an enlarged sectional elevation of the electromagnetic vibrator for the riveting tool of the machine, and Fig 5 is a diagram of the electric circuit used with the riveting machine. Referring to the drawings, the riveting machine is supported on a platform 1 and comprises a work table or base la having an upstanding hollow column 2 of substantially cylindrical shape A screw-threaded spindle 3 is rotably mounted within the column 2 and carries a gear 4 at one end. The screw-threaded portion of the spindle 3 engages the internal screw thread of a nut 5 having a pin 6 which projects through a slot lPrice 3 s 6 d l 7 in the wall of -he column 2 and which is attached to a housing 8 The housing 8 has a sleeve which is adapted to slide on the column 50 2 when the spindle 3 is rotated A carriage 9 is slidably mounted within a box shaped portion 80 of the housing 8 and attached to a casing 10 of an electromagnetic vibrator and a casing 11 of an electric motor The unit com 55 prising the components 9, 10 and 11 is rigidly connected by an arm 12 to a nut 13, the internal screw thread of which is engaged by the external screw thread on a hollow spindle 14, which is rotatably mounted in the column 2 60 parallel to the spindle 3 and adapted to be moved longitudinally of the column The hollow spindle 14 is provided with a pair of diametrically opposed slots 15 accommodating a transverse pin 17 which serves as a dog and 65 extends radially outwards from a shaft 16. Between the pin 17 and one end of the hollow spindle 14 a tension spring 118 is connected and the end of the shaft 16 remote from the pin 17 carries a gear 18 70 The two gears 4 and 18 can be rotated by a common pinion 19 attached to the shaft of a hand wheel 20 whereby the two nuts 5 and 13 are moved at equal speeds longitudinally of the column, the screw threads or the spindles 75 3 and 14 having the same helical pitch The hollow spindle 14 can also be moved longitudinally by depressing a pedal 21 against the action of the spring 118, whereby the unit consisting of the components 9, 10, 11, 12 and 13 80 is moved relative to the housing 8 A further spring 22 arranged between the box shaped portion 80 of the housing 8 and the vibrator casing 10 assists the action of the spring 118. Referring in particular to Fig 4, the virba 85 tor casing 10 is substantially cylindrical and is made of ferromagnetic material It contains a concentrically arranged inner cyli Uder 100 of ferromagnetic material and the two cyinders are connected to one another by a base 101 for 90 the cylinder 100 also made of ferromagnetic material Into one end of the cylinder 100 there is threaded a ferromagnetic hollow plug 102 for supporting a bushing 103

The other 785,678 a c' Ui' i 00 carri-s an enternally vre-;a ineaded Aplug 1 > which ike; 7 ise serves to aufpart a buslig 105. E tfeon the plugs 102 and 104 there is arranged a cozl spiing iu 6, a fibiddie portion of;Vnicri is c Onn Scc a by a transverse bridge 107 to a percussion incinoer oi vibrator ro;d l 103, Liici S is noun Lted for scing rmlvement axially of die vibcatior casing -1 u- The rod 108 at one of its cilds carries a cajA 1 G 9 of ferromagnetic na-eral, iich oveillaps the adjacent end of th&e Casn G A cylindrical solenoid -viincng Sp inserted between the cylinders 12 and 10 G viicn e byited ay a cu:rernt inlduces a Ii magnetic fcil in an ar gap 11 G t O ineans of which the cap i G 9 and th vibiator rod 108 a 1 C ur,,-i da' n The lacaine is adapted to operate at 5 J or 10 z cycles per second, at 5 G cycis being ouprated by means of a rectifier, and at 103 cycles by means of condensers. A shaft 111 is rotatably and siidabiy omoilted in a ead casing attached to base 101. A pulley 1121 ixed on the shaft 111 can be i Len h Y a te It 113 froem a pulley 115 on the outp Ut 51 atit o' an electric motor 114 within t Lie tno Lo casing 11. A lpi 1 ' i 6 e erts a force to influence tne S 1 aat 1 11 away fomn the;vidrator rod 108. The sai 111 carries a riveting head or tool 117. WI-en a woiiepicce W Fig 2) is to be ri-v tz Lu it is placed oi a support 23 on the base la and the housinpg 3 is low,ezed by turning the handvhleei 20 until the riveting head 117 is a predetenirinz a distance from the workpiece v V Foot pressure exerted on the pedal 21 suffices to mnove the -vibrator casing 1 G and its associated parts towards nhe;jorlpiece agnst the action of springs 22 and 118 until the riveting head touches the;vorilpecee and then against t 1 e action of the spring 116 until the vibrator rod 103 abuts aggainst the rotating shaft 111 and imparts its vibrations th Lrouagh this shaft to the riveting head 117. The leature thai the riveting head 117 is vi'brated as well as rotated results in improved riveting. Referring to the wiring diagram in Fig 5 %C a feeder circet for the solenoid -tvinding Sp includes a rectificr GR and a variable resistor P 2 for adjusting the current intensity as well as a control switch K governed by a time control ilt T A tdyrathron circuit arrangement is used for the time control un-t T vwhich is controllable by adjustment of a potentiometer P, and having a relay Rlls which is associated with the swvitchn K In order to energize the time control unit TT, two parallel connected double pole switches S and S, are closed The switch S can be operated by hand at H while the switch S, is coupled to the pedal 21 A double pole main switch S, when closed causes a transformer

Ue for the time control unit and the wvinding Sp, and also the motor 114 to be 6 i energised A signal lamp L, indicates whether the main switch S, is closed, and a tabie il,mina, ng lamp L can be switched or, by clesing a switch S,. The machine is prepel 1 for o, zation by 7 C closing the inain stritch S, The period of vibration desirei can be adjusted by r ?uia, ing the potentometer P,,, tle ibrator ou-tzput can be' adjusted bj mneans o the resistor P, When the rotat ig r;;eti mol 11 75 has bzzn oreou- Lt inio c'-Iltact with the workp,_ce X, tihe sr 'a S, can be cles d by coinpletely depressin g th_ pedal 21, so that the -;.nciing Sir is sapl ed ith a t nat-ng current until the relay of torf control unit 8 C o Wens the switch K. In orde that the electric control clements are not influenced by 7 vibrations, thes;y are built into a control cas ng S (Fig jj mounted separatel l Oln Lt platform 1 bs-yond the effec 85 tive ranmge of the vibrator.

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* GB785679 (A)

Description: GB785679 (A) ? 1957-10-30

Jet mill


PATENT SPECIFICATION 1785,679 Date of Application and filing Complete Specification: Aug 13, 1956. I)1 a ge No 24694156. Complete Specification Published: Oct 30, 1957. Index at acceptance:-Class 59, A 7 (D: F: G: M).

International Classif ication:-BO 2 d. COMPLETE SPECIFICATION Jet Mill I, CONRAD MARIUS TROST, a Citizen of the United States of America, residing at 334 Newbold Avenue, Moorestown, New Jersey, United States of America, do hereby declare the invention, for which I pray that a patent may be granted to me, and the method by which it is to be performed, to be particularly described in and by the following statement: - This invention refers to a fluid jet mill for comminuting dry materials and is a development of that disclosed in my Patent Specification No 765,257. In applying the mill of my said Patent Specification to certain uses, particularly to the grinding of coal on board a railway locomotive, it has been found necessary to provide a specific form thereof which is capable of being accommodated within a relatively small space and yet providing substantially undiminished grinding and classifying capacity Accordingly, certain modifications in the structure disclosed in said co-pending application were necessary and it is the purpose of the present invention to provide such modifications. Therefore, a primary object of the invention is to provide a device for grinding dry solid material, particularly bituminous coal, which is sufficiently compact to be capable of being received into a relatively small space. A further object of the invention is to provide a device, as aforesaid, which has a high degree of grinding capacity and which is particularly adaptable to bituminous coal, or similar materials. A further object of the invention is to provide a device, as aforesaid, in which the back pressures arising in the classification zone and also arising in the discharge from the mill may be relatively high with respect to the pressure under which the material is fed into the grinding chamber without materially injuring either the capacity of the mill or its efficiency in classification. A further object of the invention is to prolPrice 3 s 6 d l vide a device, as aforesaid, which can be readily modified to utilise either anvil grinding or jet grinding. A further object of the invention is to pro 50 vide a device, as aforesaid, which will be sturdy and free from high maintenance requirements. A further object of the invention is to provide a device, as aforesaid, which has no 55 moving parts. A further object of the invention is to provide a device, as aforesaid, wherein the classification of ground material will be attained with a high degree of accuracy 60 Other objects and purposes of the invention will be apparent to persons acquainted with apparatus

of this general sort upon a reading of the following disclosure and inspection of the accompanying drawings 65 In the accompanying drawings: Figure 1 is a view of a preferred form of the apparatus shown in central, vertical cross-section. Figure 2 is an enlarged sectional view 70 taken along the line II-II of Figure 1. Figure 3 is a fragmentary, sectional view similar to Figure 1 but showing a modification of the invention. Figure 4 is an enlarged section taken on 75 the line IV-IV of Figure 1: Figure 5 is a horizontal sectional view showing a further modification. Referring now to the drawings in detail, there is shown in Figure 1 an elongated cas 80 ing, or grinding housing, 1, the same being of either cylindrical or rectangular cross-section, having an anvil 2, located at and closing one end thereof and a plug 3 located at the other end of said casing Said anvil 2 is held 85 in position by any convenient means, as the set screw 4 Plug 3 is held in position by any convenient means, as the set screw 6. A conduit 7 terminating in a nozzle 8 extends through the plug 3 from a point exter 90 nally of the apparatus and is operatively associated with a feeding device 5, as a hopper Said conduit 7 may be connected to any convenient source of grinding fluid under pressure, such as either compressed air or steam A block 9 is positioned within the casing 1 intermediate the nozzle 8 and the anvil 2 and is normally somewhat closer to said nozzle An internal venturi passageway 11, having a flared entry end 12, is provided through said block 9 co-axial with the said nozzle 8 and with the casing 1. An off-take conduit 13, of cross section preferably as shown in Figure 4, extends upwardly from the opening 15 in the casing 1 at a point therein intermediate the block 9 and the anvil 2 In the particular embodiment of the invention here shown, said offtake conduit is substantially adjacent the discharge end of said venturi passageway 11 in said block 9, and somewhat spaced from the face of the anvil 2, but this may vary according to the kind of material being handled. A first orienting conduit 14 is placed above said off-take conduit 13 and connected thereto by flanges 17 and 20 in a known manner Said first orienting conduit curves rather sharply, as about 90 degrees, in a direction away from the nozzle and is connected to a second orienting conduit 16 by flanges 18 and 25 Said second orienting conduit curves, as about 90 degrees, in a direction away from the grinding chamber 10 and provides, in combination with the conduit 14, an offset and reverse curve A classifying section 19 is substantially

semi-circular and is connected to the second orienting conduit 16 by the flanges 21 and 22 Said classifying conduit 19 may be of a variety of cross-sectional shapes, including circular, elliptical and trapezoidal, as set forth in detail in my aforesaid Patent Specification, but is preferably circular or elliptical Said classifying conduit has a discharge opening 23 which communicates through a discharge conduit 26, having an entry throat 24, with any desired point of use or storage of the material withdrawn from the classifying conduit. A return conduit 27, of substantially circular cross-section, is connected at one end to the classifying conduit 19 by the flanges 28 and 29 The other end of said return conduit 27 is connected to the casing 1 and communicates with the interior of the chamber 32 through a return opening 31, located between the plug 3 and the block 9 The return conduit 27 may be straight, as shown. In Figure 3 there is shown a modification of the device in which the anvil 2 is replaced by a plug 36 through which extends a conduit and nozzle assemblage 37 which is placed in opposing, co-axial, relationship with the nozzle 8 In all other respects this apparatus is the same as that described in connection with Figures 1, 2 and 4. In Figure 5 there is illustrated a further modification in which an anvil 41 is placed within the grinding chamber 10 substantially under the off-take conduit whose opening 15 is indicated by broken lines in said Figure 5 70 Fluid conducting conduits 42 and 43, for delivering high velocity jets, are added to the structure of Figure 3 and each of these jets, together with the main grinding and feeding conduit 7, direct streams of grinding fluid 75 against the sides of the anvil 41 Partially comminuted material to be ground may be fed through any or all of the conduits 37, 42 and 43 in addition to the feeding thereof through the conduit 7 or, in instances where 80 the material is of maximum grinding diffilculty, it may be fed into the device only through either or both of the conduits 7 and 37, and the auxiliary jets will function to drive material circulating through the grind 85 ing chamber 10 against the several faces of the anvil 41 Other parts of the device shown in Figure 5 are the same as those shown in connection with Figures 1, 2 and 4, and are numbered correspondingly Likewise, the 90 device discharges through a discharge opening 15 and through classification means the same as shown in Figure 1 and returned material re-enters the device for further grinding through the return opening 31 95 OPERATION. A mixture of partially comminuted material, as bituminous coal, with a grinding fluid, as steam or air, is introduced into the device from the conduit 7 through the nozzle 100 8 It passes through the venturi passageway 11 and is driven at a high velocity against the face of the

anvil 2 The material is largely shattered and that which is sufficiently fine to be carried by the fluid stream passes out 105 of the grinding chamber 10 through the opening 15 into the first orienting conduit 14 The reverse turn in the conduits 14 and 16 provides an initial classifying action in that the coarser material will partially sepa 110 rate in each turn from the finer material and thus will tend to gather on the radially outermost wall of the classifying section 19 somewhat more quickly than is possible in previously known devices Thus, the use of the 115 reversely curved conduit enables the classifying chamber to be materially smaller than in those cases where the curve is all in one direction As the material moves through the classifying chamber 19, the coarser por 120 tion thereof continues to gather at the radially outermost wall so that by the time a given portion thereof reaches the zone adjacent the outlet opening 23, only the finer materials within a predetermined classifica 125 tion size range are adjacent the radially inner wall of the classification chamber Inasmuch as the return conduit 27 is of somewhat smaller cross-sectional area than that of the classification chamber 19, that portion of the 130 785,679 thereof If desired, further supplies of solid material may be introduced through one or more of the conduits 37, 42 and 43 Alternatively, the material may be introduced only through conduits 37, 42 and 43 and jet 8 left 70 free to carry only the return load from return conduit 27 This will be somewhat more efficient in those cases where there is a high volume of recirculating material. Such multiple introduction of material may 75 be used in a wide number of cases and will be particularly useful in those instances where the material shatters relatively easily but it is not possible for any one jet to carry as high a load of material as the classifying 80 chamber can handle. in all three forms of the mill here shown, the grinding chamber is kept relatively short so that the material introduced thereinto through the nozzle 8 strikes either the anvil 85 or the opposing jet with a maximum of force. Thus, it is possible to utilise a relatively low energy input with a maximum of efficiency and the effectiveness of the grinding does not seriously suffer The reverse bend in the con 90 duit leading to the classification chamber effects certain preliminary classification so that the total conduit length from the opening 15 to the opening 31 may be kept at a minimum This effects further savings in 95 energy and space requirements, without permitting classification effectiveness to be materially diminished Thus, the objects and purposes above set forth have been accomplished 100 While certain specific embodiments of the invention have been set forth in detail for illustrative purposes,

it will be recognised by those skilled in the art that various other modifications may be made without depar 105 ture from the principles of the invention, and hence the appended claims are to be interpreted as including such variations excepting as such claims may by their own terms expressly limit otherwise 110 Having regard to the provisions of Section 9 of the Patents Act attention is directed to the claims of Patent No 765,257.


* GB785680 (A)

Description: GB785680 (A) ? 1957-10-30

Improvements in and relating to self-centering or aligning rollers


COMPLETE SPECIFiCATION Improvements in and relating to Self-Centering or Aligning Rollers We, UNITED STATES STEEL CORPORATION, a Corporation organized and existing under the laws of the State of New Jersey, United Stashes of America, doing business at 525, William Penn Place, Pittsburgh 3O, State of Pennsylvania, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: This invention relates to self-centering or aligning rollers for aligning travelling strip material with respect to a predetermined path of travel normal to the rollers. Essentially the type of apparatus with which the present invention is concerned, in its fullest embodiment, involves at least one roller of the selfcentering

or aligning type, such roller extending generally transversely to the intended path of travel of the strip and having two roller sections one on each side of its transverse center, the two sections being adapted to rotate in unison at the same peripheral speed when rotated by external driving means or by frictional contact with the travelling strip and being so adapted and arranged that they (the roller sections), when acting against the travelling strip surface engaged by he roller sections, produce a reactive force acting inwardly toward the center of ke roller whereby the strip is centered or ,liJned with respect to the desired path of travel Examples of such rollers and their manner of operation are described in the specifications of our prior United Kingdom patents 709.908 709,959, 713,557, 717,671, 719.088, 725,762, 730,594, 735,561 and 735,574 and for convenience in the ensuing statement of invention and in Claim 1, the et pression "of the type hereinbefore defined" is used to designate self-centering and aligning rollers of that general type. The present invention consists in a selfcentering or aligning roller of the type hereinbefore defined adapted for aligning or centering a travelling strip of a predetermined width, in which each section of the roller comprises a cylindrical portion adjacent the transverse center, a first conical portion adjacent said cylindrical portion having a decreasing diameter away from the cylindrical portion, and a second conical portion adjacent said first conical portion having an increasing diameter away from said first conical portion, the maximum diameter of said second conical portion being approximately the same as the diameter of the cylindrical portion, the distance between the junctions of the first and second conical portions on opposite sides of the transverse center being no greater than the width of the strip to be handled. In order that it may be clearly understood and readily carried into effect, the invention will now be described, by way of example, with reference to the accompanying drawings, in which: Figure 1 is a schematic plan view of an endless belt arrangement utilizing the present invention; Figure 2 is a side elevation of the arrangemelt shown in Figure 1, and Figure 3 is a view taken on the line III- III of Figure 2. Referring now to the drawings, the travelling strip is here represented by a belt (13) which passes around the self-centering or aligning roller 4 and the rollers 5, 6 and 7. The self-centering or aligning roller 4 is in this particular instance mounted on a rigid U-shaped yoke 8 which is pivotally mounted about a knife-edged pivot 9 at the bottom of each side arm of the yoke and a crosspiece 10

interconnects the yoke arms near their bottom ends. From the center of the crosspiece 10 there extends an arm 11. Bolts 12 and 13 are attached to the base 14 of the apparatus, the bolt 12 passes through aligned holes on the crosspiece 10 and arm 11 and the bolt 13 extends upwardly through a hole in the free end of the arm 11. A spring 15 surrounds the bolt 13 and is confined between the upper part of the arm 11 and the nut 16 so that the arm 11 is biased downwardly at all times to tension the belt (*. The holes for the bolt 12 are slightly larger than the bolt to permit a sight tilting of the yoke. if desired a counterweight can be substituted for the spring 15. The roller 4 is a self-centering roller of the general type disclosed iii our prior British specification 717,671 but it has a specific contour. This roller may be of the type shown in our prior British specifications 709,908 or 735,561 both of which are of the general type hereinbefore defined. Each half of the roller 4 has a cylindrical section 17 adjacent the transverse center of the roller, a conical section 18 adjacent thereto which decreases in diameter away from the cylindrical portion and a conical section 19 adjacent the bearings 20 which increases in diameter away from its adjacent reversely tapered conical section 18. The width of the belt (B) is preferably slightly greater than the distance between the smaller diameter outer ends of the conical sections 18. The diameter of the cylindrical sections 17 is approximately equal to the maximum diameters of the outer conical sections 19, that is to say, it may be exactly equal to, slightly greater or less in diameter than said sections. The amount of taper of the conical sections is greatly exaggerated in the drawings for the purpose of illustration and in most instances the difference in radius is only a matter of a few thousandths of an inch. In the arrangement shown the rollers 5 and 7 are cylindrical rollers of the narrowbodied type so called because the actual strip engaging surface is essentially narrower than the length of the rollers and the width of the strip. The roller 6 may be either a roller of the narrow-bodied type or a full bodied cylindrical roller having the strip supporting surface extending the full length of the roller and somewhat greater than the width of the strip. The strip is subjected to treatment in the container 21 and any convenient means may be provided for driving the strip;, for example, ally one of the rollers may be driven or the strip itself may be driven by contact with an external roller bearing on the surface of the strip. The arrangement particularly described and illustrated is particularly suited for flex ible belts and the exact point of contact of the belt

on the roller 4 depends upon the tensicn applied vay the spring 15. However, it will be seen thas the belt does not contact the center of the roller and there is therefore no danger of the belt being nlarLed by the separation of tile center of the roller sections. What side claim is: 1. A self-centering or aligning roller of the type hereinbefore defined adapted for aligning or centring a travelling strip of a predetermined width, in which each section of the roller comprises a cylindrical portion adjacent the transverse center, a first conical portion adjacent said cylindrical portion having a decreasing diameter away from the cylindrical portion, and a second conical portion adjacent said first conical portion having an increasing diameter away from said first conical portion. the maximum diameter of said second conical portion being approximately the same as the diameter of the cylindrical portion, the distance between the junctions of the first and second conical portions on opposite sides of the transverse center being no greater than the width of the strip to be handled. 2. An assembly of self-centering rollers for centering or aligning a moving strip with respect to a predetermined path of travel normal to the rollers, such assembly comprising a self-centering or aligning roller according to Claim 1, and a second roller having a strip supporting surface of less width than the predetermined width of the strip. 3. An assembly of self-centering rollers for centering or aligning a moving strip with respect to a predetermined path of travel normal to the rollers, said assembly comprising a self-centering or aligning roller according to Claim 1, and tiro rollers of the narrow-bodied type, one engaging the strip before and the other after engagement with said aligning roller. 4. An assembly according to Claim 2 or Claim 3 wherein the arrangement and disposition of the rollers is sudi that i!l its travel the strip engages a substantial arc of the periphery of at least one of the rollers. 5. A self-centering or aligning roller substantially as described with reference to the accompanying drawings. 6. An assembly substantially as described with reference to the accompanying dra -. in.rs.

* GB785681 (A)

Description: GB785681 (A) ? 1957-11-06

Steroid compounds

Description of GB785681 (A) Translate this text into Tooltip

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The EPO does not accept any responsibility for the accuracy of data and information originating from other authorities than the EPO; in particular, the EPO does not guarantee that they are complete, up-to-date or fit for specific purposes.

PATENT SPECCIFICATION- |gpi Date of Application and filing Complete Specification: Sept 16, 1953. No 25642/53. Application made in United States of America on Sept 17, 1952. Complete Specification Published; Nov 6, 1957. Index at acceptance: -Class 2 ( 3), U 4 (A 1: A 2: BI: C 3: C 5). International Classification:-CO 7 c. COMPLETE SPECIFICATION Steroid Compounds We, MERCK & CO INC, a corporation duly organised and existing under the laws of the State of New Jersey, United States of America, of Raliway, New Jersey, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: - This invention is concerned with novel cyclopentanopolyhydro phenanthrene compounds and processes for preparing them. In brief, this invention provides novel etienoylpyruvic acid compounds having the formula: CO 2 CO Cf CO co FORML/b / in which the 3-position is occupied either by a divalent group convertible to keto by acid hydrolysis or by a pair of univalent groups together convertible to a single keto group by acid hydrolysis; and novel etienoylpyruvic acid compounds having the formula: FORMULA 9 in which the 3-position is occupied by a univalent group which is convertible to keto by acid hydrolysis. Examples of bivalent groups which may occupy the 3-position in the compounds of lPrice 3 s 6 d l Formula I are cyclic ketal groups, e g

ethylenedioxy, ethylene dithioketal, and ethylene hemi 30 thioketal; pairs of univalent groups which may occupy the 3-position in the compounds of Formula I include non-cyclic ketals such as dimethyl ketal; single univalent groups which may occupy the 3-position in the compounds 35 of Formula II include enol ethers such as ethyl enol ether The preferred group is the ethylenedioxy group, which gives a compound of Formula II in which the 3-position has a " substituent 40 In the subsequent description for convenience and to avoid repetition, reference will be made to the 3-ethylenaedioxy etienoylpyruvic acid compounds, and to the 3-ethylenedioxy 20-keto-pregnenes from which they are pre 45 pared It is to be understood, however, that the reactions described for such compounds apply also to the analogous compounds in which the 3-position of the molecule is substituted in any of the ways mentioned 50 above in connection with the definition of Formulae I and II, so that the compounds in question may have one or two nuclear double bonds, depending on how the 3-position is substituted, i e when the 3-substituent is a ketal 55 or cyclic ketal, the compound will be a AW-ene and when it is an enol ether, the compound will be a A 3 A 5-daene. The function of this 3-substituent is to protect the 3-keto, group from reactions such as 60 oxidation and addition, and the manner of its introduction forms part of the invention claimed in our copending Application No. 29358/55 (Serial No 763,208). The novel compounds of the invention are 65 useful as starting materials in the process described and claimed in the specification of cur copending Application No 9553/56 (Serial No 785,683), the compound forming the subject of that application being treated to form 70 derivatives of 1 l-dehydrocorticosterone by processes described and claimed in the speci785681 fication of our copending Application No. 9554/56 (Serial No 785,684). In accordance with the present invention, derivatives of 11-keto progesterone in which the 3-keto substituent is blocked or protected by a suitable radical convertible to keto by acid hydrolysis can be converted to derivatives of etienoylpyruvic acid having the Formulh I and II hereinbefore by reacting the 11-keto progesterone derivative with an oxalic acid diester in the presence of a strong alkali The said derivatives of 11-keto progesterone form part of the invention claimed in the specification of our copending application No 7716/56 I(Serial No 777,691) and methods for their preparation are described and claimed in the specifications of our copending applications Nos 7716/56 and 9552/56 (Serial Nos. 777,691 and 777,693). Thus, for example, 3-ethylenedioxy-11-keto progesterone, may be

reacted with an oxalic acid diester in the presence of a strong alkali in a suitable inert medium to obtain 3-ethylsnedioxy-11-keto etienoylpyruvic acid The d or dl-form of 3-tthylenedioxy-11-keto progesteroane may be used In carrying out this reaction, it is usually preferred to use an oxalic acid diester of a lower alkanol, such as dimethyl oxalate or diethyl oxalate, since these esters are readily and conveniently obtained. Preferred strong alkalis are alkali metal alkoxides such as sodium methoxide and potassium ethoxide although other strong alkalis, such as sodamide, sodium hydride, and sodium triphenylmethyl, are also suitable Inert organic solvents, such as benzene, toluene, xylene and petroleum hydrocarbons are satisfactory for use as solvent mediums in carrying out this reaction Thus the preparation of A4 o 3-ethylenedioxy-11-keto-etienoylpyruvic acid is most conveniently effected by reacting the 3-ethylenedioxy derivative of l 1-keto progesterone with dimerhyl oxalate in the presence of sodium methoxide in a benzene medium. The resulting mixture is permitted to stand at room temperature for about 10-20 hours in order to complete the formation of the desired etienoylpyruvic acid compound Upon completion of the reaction, the mixture is cautiously acidified and the pyruvic acid compound can, be readily recovered by extraction with a water-immiscible solvent such as ether and evaporation of the solvent extracts. The following example illustrates methods of carrying out the process of the invention. EXAMPLE. A 5-3-Ethylenedioxy-11-Keto-Etienoylpyruvic Acid. A mixture of 1 3 g of dry sodium methoxide, 3 0 g of dimethyl oxalate and 2 50 g. of the 3-ethylenedioxy derivative of d-11-keto progesterone was dissolved in 20 cc of dry benzene The solution was permitted to stand at room temperature for 20 hours, poured into ite waters and carefully acidified with dilute sulphuric acid and excess sodium dihydrogen phosphate The liberated organic product was dissolved in ether, and the ethereal layer extracted with 55 cc of aqueous IN potassium hydroxide After standing at room temperature for one hour, the alkaline extract was cooled and acidified as before The liberated acid was extracted twice with ether, the ethereal solution washed and concentrated to dryness inz vacuo Crystallization of the residue from ether yielded d-:1-3-ethylenedioxy-11keto-etienoylpyruvic acid, dec 180-182 ' C. The above procedure was repeated using as starting material dl-S -3-ethylenedioxy-11,20diketo-pregnene obtained by total synthesis. The product, dl-L\-3-ethiylenedicxy-11-ketoetienoylpyruvic acid, was

crystallized from ether (m p 174-7 C dec).


* GB785682 (A)

Description: GB785682 (A) ? 1957-11-06

Steroid compounds

Description of GB785682 (A) Translate this text into Tooltip

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PATENT SPECIFICATION 785 682 Date of Application and filing Complete Specification: Sept 21, 1953. No 25992153. Application made in United States of America on Sept 20, 1952. Complete Specification Published: Nov 6, 1957. Index at acceptance:-Class 2 ( 3), U 31 U 4 (A 1; A 2; B 1; C 4; CX). International Classification:-CO 7 c, COMPLETE SPECIFICATION Steroid Compounds; We, MERCK & CO INC, a corporation duly organised and existing under the laws of the Stare of New Jersey, United States of America, of Rahway, New Jersey, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be

particularly described in and by the following statement:- This invention is concerned with novel cyclopentanopolyhydrophenanthene compounds and processes for preparing them. In brief, this invention provides novel 20-cyano-pregneneus compounds having the formula: and II R represents an acyloxy group. Examples of bivalent groups which may occupy the 3-position in the compounds of Formula I are cyclic ketal groups, e g ethylenedioxy, ethylene dithioketal, and ethylene hemithiolketal; pairs of univalent groups which may occupy the 3-position in the compounds of Formula I include non-cyclic ketals such as dimethyl ketal; single univalent groups which may occupy the 3-position in the consp'ounids of Formula II include enel ethers such as ethyl enol ether The preferred groupi is the ethylenedioxy group, which gives a compound of Formula II in which the 3-position has a 3 6 Formula I in which the 3-position is occupied either by a bivalent group, convertible to keto by acid hydrolysis or by a pair of univalent groups together convertible to a single keto groups by acid hydrolysis; and novel 20-cyano-pregnene compounds having the formula Formula II in which the 3-position is occupied by a univalent group' which is convertible to' keto by acid hydrolysis In the foregoing Formulx I C,, O substituent. C#2 -0 o In the subsequent description, for convenience and to, avoid repetition, reference will be made to, the As-3-ethylenedioxy-1 l-keto20-cyano-20-hydroxy-21-acetoxy pregnene and 45 to the A'-3-ethylenedioxy-11,20-diketo-21acetoxy-pregnene from which it is prepared. It is to' be understood, however, that the reactions described for such compounds apply also, to the analogous compounds in which 50 there is a different 21-acyloxy group' and/or in which the 3-position of the molecule is substituted in any of the ways mentioned above in connection with, the definition of Formulas I and II, so that the compounds in 55 question may have one or two' nuclear double bonds, depending on how the 3-position is substituted, i e when the 3-substituent is a ketal or cyclic ketal, the compound will be a 5-ene and when it is an enol ether, the Gcon 60 pound will be a A"' -diene. The function of this 3-substituent is to protect the 3-keto, group from, reactions such as oxidation and addition, and the manner of its introductionb forms part of the invention 65 claimed in our copending Application No 29358/55 (Serial No 763,208). The novel compounds of the invention are useful as starting materials in the process described and claimed in the specification of our copending Application No 9817/56 (Serial No 785,685) the compound forming the subject of that application being treated to form

cortisone esters by processes described and claimed in the specification of our copending Application No 9818/56 (Serial No. 785,686). The novel 3-ethylenedioxy compounds are prepared from steroid compounds of formula CO, C Al in which R represents an acyloxy substituent. In this process, A'-3-ethylenedioxy-11,20diketc-21-acetoxypregnene is converted to AW 3 -ethylenedioxy 11 -keto 20-cyano 20hydroxy-21-acetoxypregnene, by bringing a solution of the starting material into intimate contact with hydrogen cyanide Solvents for the starting material which are inert to the action of hydrogen cyanide, such as hydrocarbons, halogenated hydrocarbons and ethers, are suitable media for carrying out this reaction Generally, it is found that it is desirable to add a small amount of an organic base such as triethylamine to the reaction mixture to, obtain maximum yields, although the reaction can also be carried out without the addition of the organic base. The following example illustrates a method of carrying out the invention. EXAMPLE. Preparation of A'-3-Ethylenedioxy-11-keto-20hydroxy-20-cyano-21-acetoxypregnene A solution of 380 mg of A'-3-ethylenedioxy-11,20-diketo-21-acetoxypregnene in 3 cc. of ethylene dichloride was treated with 0 3 cc. of liquid hydrogen cyanide and 0 05 cc of triethylamine After ten niinutes, 3 0 cc of absolute ether was added The partially crystalline mixture was treated with an additional 3 0 cc of ether after 1 hour At the end of three hours, the product A'-3-ethylenedioxy 11 -keto 20 -hydroxy 20 -cyano 21acetoxypregnene, was filtered Recrystallization from chloroform-ether gave the pure cyanhydrin, mnp 220-224 C (dec). When the racemic mixture, dl-A'1-3-ethylenedioxy 11,20 -diketo 21 -acetoxypregnene, was reacted in the manner described above, d I-A 5-3-ethylenedioxy 11 -keto 20 -hydroxy20-cyano-21-acetoxypregnenel, mp 220-225 C (dec) was obtained. which form part of the subject of our copending Application No 9554/56 (Serial No 15 785,684) by a process which can be represented chemically as follows:

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