Unsaturation Between The 4- And 5-positions Patents (Class 552/598)
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Patent number: 9206219Abstract: The invention relates to 17-hydroxy-17-pentafluoroethylestra-4,9(10)-diene 11-aryl derivatives of the formula I with progesterone-antagonizing action and to processes for preparation thereof, to use thereof for treatment and/or prophylaxis of disorders and to the use thereof for production of medicaments for treatment and/or prophylaxis of disorders, especially of fibroids of the uterus (myomas, uterine leiomyomas), endometriosis, heavy menstrual bleeds, meningiomas, hormone-dependent breast cancers and complaints associated with the menopause, or for fertility control and emergency contraception.Type: GrantFiled: July 8, 2010Date of Patent: December 8, 2015Assignee: Bayer Intellectual Property GmbHInventors: Ulrich Klar, Wolfgang Schwede, Carsten Möller, Andrea Rotgeri, Wilhelm Bone
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Publication number: 20140296510Abstract: A method as well as new intermediates for preparing Ulipristal acetate (a compound I) and a method for preparing the new intermediates are provided. The intermediate in a constitutional formula IV is conductive to reacting with methyl lithium or methyl Grignard reagent, a protective group is easy to be removed after a reaction, side reactions are few, a mid-term treatment is simple, the reagents used are cheap, costs are low and a yield is high, if a compound in a constitutional formula V is obtained by the reaction of a compound in a constitutional formula III and the intermediate in the constitutional formula IV, the yield of a two-step reaction is 75%, a purity is above 98%. wherein R is defined in the specification.Type: ApplicationFiled: July 12, 2012Publication date: October 2, 2014Applicants: Changzhou Siyao Pharm Co., Ltd., Utopharm (Shanghai) Co., Ltd.Inventors: Junzhi Luo, Yongqiang Sun, Xun Luo, Yimin Yan, Zhaojun Wang, Mingxia Qian, Yongrui Tu
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Publication number: 20140107089Abstract: Disclosed are compounds having the general formula: wherein R1-R4 and X are as defined herein, pharmaceutical compositions including such compounds, and a method of treating a patient involving antagonizing the endogenous progesterone, such as in inducing menses and treating endometriosis, dysmenorrhea, endocrine hormone-dependent tumors, meningiomas, uterine leiomyomas, or uterine fibroids, inhibiting uterine endometrial proliferation, inducing cervical ripening, inducing labor, and in contraception.Type: ApplicationFiled: September 10, 2013Publication date: April 17, 2014Applicant: The United States of America, as represented by the Secretary, Department of Health and Human ServInventors: Hyun K. Kim, Richard P. Blye, Pemmaraju N. Rao, James W. Cessac, Carmie K. Acosta, Anne Marie Simmons
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Publication number: 20130281422Abstract: The present invention relates generally to gynecological diseases and in particular to a method for reducing pain associated with dislocation of basal endometrium.Type: ApplicationFiled: December 23, 2011Publication date: October 24, 2013Applicant: PREGLEM S.A.Inventors: Ernest Loumaye, Elke Bestel, Ian Osterloh
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Publication number: 20120232042Abstract: The invention relates to 17-hydroxy-13-methyl-17-pentafluoroethyl-11-acyloxyalkylenephenyldodecahydrocyclopenta[a]phenanthren-3-one derivatives of the formula I with progesterone-antagonising action and to processes for preparation thereof, to use thereof for treatment and/or prophylaxis of disorders and to the use thereof for production of medicaments for treatment and/or prophylaxis of disorders, especially of fibroids of the uterus (myomas, uterine leiomyomas), endometriosis, heavy menstrual bleeds, meningiomas, hormone-dependent breast cancers and complaints associated with the menopause, or for fertility control and emergency contraception.Type: ApplicationFiled: July 7, 2010Publication date: September 13, 2012Applicant: BAYER PHARMA AKTIENGESELLSCHAFTInventors: Ulrich Klar, Wolfgang Schwede, Carsten Moller, Andrea Rotgeri, Ursula Krenz
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Publication number: 20120184515Abstract: The invention relates to 17-hydroxy-17-pentafluoroethylestra-4,9(10)-diene-11-methyleneoxyalkylenearyl derivative of the formula I with progesterone-antagonising action and to processes for preparation thereof, to use thereof for treatment and/or prophylaxis of disorders and to the use thereof for production of medicaments for treatment and/or prophylaxis of disorders, especially of fibroids of the uterus (myomas, uterine leiomyomas), endometriosis, heavy menstrual bleeds, meningiomas, hormone-dependent breast cancers and complaints associated with the menopause, or for fertility control and emergency contraception.Type: ApplicationFiled: July 7, 2010Publication date: July 19, 2012Applicant: BAYER PHARMA AKTIENGESELLSCHAFTInventors: Ulrich Klar, Wolfgang Schwede, Carsten Möller, Andrea Rotgeri, Wilhelm Bone
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Patent number: 8110691Abstract: A new industrial process for the synthesis of solvate-free 17?-acetoxy-11?-[4-(N,N-dimethyl-amino)-phenyl]-19-norpregna-4,9-diene-3,20-dione [CDB-2914] of formula (I) which is a strong antiprogestogene and antiglucocorticoid agent. The invention also relates to compounds of formula (VII) and (VIII) used as intermediates in the process.Type: GrantFiled: May 18, 2007Date of Patent: February 7, 2012Assignee: Richter Gedeon Nyrt.Inventors: Lajosné Dancsi, György Visky, Zoltán Tuba, János Csörgei, Csaba Molnár, Endréné Magyari
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Publication number: 20100298585Abstract: A method for the synthesis of dienogest from 3-methoxy-estra-1,3,5-trien-17-one includes the steps of a) reacting 3-methoxy-estra-1,3,5-trien-17-one with alcohol in the presence of an acid in an organic solvent to form 3-methoxy-17,17-dialkoxy-estra-1,3,5-triene; b) subjecting the product of step a) to partial reduction by reaction with alkali metal in liquid ammonia; c) treating the product of step b) with mild acid; d) reacting the product of step c) with cyanomethyl lithium; e) treating the product of step d) with oxalic acid; and f) treating the product of step e) with pyridinium tribromide in pyridine to yield dienogest.Type: ApplicationFiled: May 24, 2010Publication date: November 25, 2010Applicant: HEYL CHEMISCH-PHARMAZEUTISCHE FABRIK GMBH & CO. KGInventors: Thomas Döhler, Dirk Walther, Michael Werner
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Publication number: 20090069584Abstract: The present invention provides for a crystalline polymorph of levonorgestrel and processes for making the same.Type: ApplicationFiled: September 5, 2008Publication date: March 12, 2009Applicant: ScinoPharm Taiwan Ltd.Inventors: Yu-Sheng Chang, Shu-Ping Chen
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Publication number: 20090012321Abstract: The present invention relates to a process for preparing 17?-acetoxy-6-methylenepregn-4-ene-3,20-dione (4) as an intermediate, and to processes for preparing medroxyprogesterone acetate (1) (17?-acetoxy-6?-methylpregn-4-ene-3,20-dione) and megestrol acetate (2) (17?-acetoxy-6-methylpregna-4,6-diene-3,20-dione) via this intermediate (4).Type: ApplicationFiled: June 5, 2008Publication date: January 8, 2009Inventors: Klaus ANNEN, Thomas Linz, Karl-Heinz Neff, Rolf Bohlmann, Henry Laurent
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Publication number: 20080207931Abstract: Provided is a method for selective extraction of steroid compounds using entrapped ?-cyclodextrin polymers. Particularly, steroid hormones can be effectively selected from a biological sample by selectively extracting steroid compounds using entrapped ?-cyclodextrin polymers, prepared by adding epichlorohydrin to ?-cyclodextrin to prepare a polymer in a gel state, entrapping the polymer and pulverizing the products without using an additional device required in conventional solid-phase extraction.Type: ApplicationFiled: November 29, 2007Publication date: August 28, 2008Inventors: Man Ho Choi, Dong Hyun Kim, Bong Chul Chung, Ju-Yeon Moon
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Patent number: 7087591Abstract: A compound having the general formula: in which: R1 is a member selected from the group consisting of —OCH3, —SCH3, —N(CH3)2, —NHCH3, —CHO, —COCH3 and —CHOHCH3; R2 is a member selected from the group consisting of halogen, alkyl, acyl, hydroxy, alkoxy, acyloxy, alkyl carbonate, cypionyloxy, S-alkyl and S-acyl; R3 is a member selected from the group consisting of alkyl, hydroxy, alkoxy and acyloxy; R4 is a member selected from the group consisting of hydrogen and alkyl; and X is a member selected from the group consisting of ?O and ?N—OR5, wherein R5 is a member selected from the group consisting of hydrogen and alkyl.Type: GrantFiled: February 23, 2005Date of Patent: August 8, 2006Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Hyun K. Kim, Richard P. Blye, Pemmaraju N. Rao, James W. Cessac, Carmie K. Acosta
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Patent number: 6900193Abstract: The present invention relates, inter alia, to compounds having the general formula: in which: R1 is a member selected from the group consisting of —OCH3, —SCH3, —N(CH3)2, —NHCH3, —NC4H8, —NC5H10, —NC4H8O, —CHO, —CH(OH)CH3, —C(O)CH3, —O(CH2)2N(CH3)2, and —O(CH2)2NC5H10; R2 is a member selected from the group consisting of hydrogen, halogen, alkyl, acyl, hydroxy, alkoxy (e.g., methoxy, ethoxy, vinyloxy, ethynyloxy, cyclopropyloxy, etc.), acyloxy (e.g., acetoxy, glycinate, etc.), alkylcarbonate, cypionyloxy, S-alkyl, —SCN, S-acyl and —OC(O)R6, wherein R6 is a functional group including, but not limited to, alkyl (e.g., methyl, ethyl, etc.), alkoxy ester (e.g., —CH2OCH3) and alkoxy (—OCH3); R3 is a member selected from the group consisting of alkyl, hydroxy, alkoxy and acyloxy; R4 is a member selected from the group consisting of hydrogen and alkyl; and X is a member selected from the group consisting of ?O and ?N—OR5, wherein R5 is a member selected from the group consisting of hydrogen and alkyl.Type: GrantFiled: March 17, 2000Date of Patent: May 31, 2005Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Hyun K. Kim, Richard P. Blye, Pemmaraju N. Rao, James W. Cessac, Carmie K. Acosta, Anne Marie Simmons
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Patent number: 6861415Abstract: A compound having the general formula: in which: R1 is a member selected from the group consisting of —OCH3, —SCH3, —N(CH3)2, —NHCH3, —CHO, —COCH3 and —CHOHCH3; R2 is a member selected from the group consisting of halogen, alkyl, acyl, hydroxy, alkoxy, acyloxy, alkyl carbonate, cypionyloxy, S-alkyl and S-acyl; R3 is a member selected from the group consisting of alkyl, hydroxy, alkoxy and acyloxy; R4 is a member selected from the group consisting of hydrogen and alkyl; and X is a member selected from the group consisting of ?O and ?N—OR5, wherein R5 is a member selected from the group consisting of hydrogen and alkyl.Type: GrantFiled: April 30, 1997Date of Patent: March 1, 2005Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Hyun K. Kim, Richard P. Blye, Pemmaraju N. Rao, James W. Cessac, Carmie K. Acosta
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Patent number: 6514956Abstract: The present invention concerns with steroid compounds of formula (I) wherein R1 is cyclohexyl or cycloheptyl, R2 is hydrogen or C1-C6 alkyl, R3 is hydrogen, C1-C6 alkyl or methylol, R4 is hydrogen or hydroxymethylene and a pharmaceutically acceptable salt thereof. The invention also concerns with a method for preparation of the compounds, pharmaceutical compositions containing the compounds as its active component and use of the compounds and the pharmaceutical compositions in preparing medicines for treating diseases, e.g. those associated with progestin dependence.Type: GrantFiled: August 1, 2001Date of Patent: February 4, 2003Assignees: Shanghai Zhongxi Pharmaceutical Co., Ltd., Xianju Pharmaceutical Co., Ltd.Inventors: Lianzhi Chen, Lin Zuo, Mingwai Wang, Zhengyu Ye, Wenliung Chen
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Patent number: 6503895Abstract: This invention describes the new 17&agr;fluoroalkyl steroids of general formula I as well as their physiologically compatible salts with bases. The new compounds have an extraordinary strong antigestagenic action and are suitable for the production of pharmaceutical preparations.Type: GrantFiled: October 18, 2001Date of Patent: January 7, 2003Assignee: Schering AktiengesellschaftInventors: Wolfgang Schwede, Arwed Cleve, Ulrich Klar, Gunter Neef, Kristof Chwalisz, Martin Schneider, Ulrike Fuhrmann, Holger Heb-Stumpp
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Publication number: 20020025951Abstract: A compound having the general formula: 1Type: ApplicationFiled: May 24, 1999Publication date: February 28, 2002Inventors: HYUN K. KIM, RICHARD P. BLYE, PEMMARAJU N. RAO, JAMES W. CESSAC, CARMIE K. ACOSTA
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Patent number: 6316432Abstract: This invention describes the new 17&agr;-fluoroalkyl steroids of general formula I as well as their physiologically compatible salts with acids, and for —CO2R9 radicals with R9 meaning hydrogen as well as their physiologically compatible salts with bases. The new compounds have an extraordinarily strong antigestagenic action and are suitable for the production of pharmaceutical preparations.Type: GrantFiled: March 1, 2000Date of Patent: November 13, 2001Assignee: Schering AktiengesellschaftInventors: Wolfgang Schwede, Arwed Cleve, Ulrich Klar, Gunter Neef, Kristof Chwalisz, Martin Schneider, Ulrike Fuhrmann, Holger Heb-Stumpp
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Patent number: 6037339Abstract: A C-11 substituted steroid and a method of use of a C-11 substituted steroid to treat osteoporosis.Type: GrantFiled: January 16, 1998Date of Patent: March 14, 2000Assignee: Akzo Nobel N.V.Inventors: Hubert Jan Jozef Loozen, Lodewijk Pieter Cornelis Schot, Jane Margretha Lena van der Werf-Pieters
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Patent number: 5929262Abstract: Methods for the preparation of the 19-norprogesterone of formula I ##STR1## and its intermediates, in crystalline and amorphous forms are disclosed. The process is performed by (1) protecting the hydroxyl group of a compound of formula II ##STR2## (2) reacting the protected compound with an alkali or alkaline earth metal anion radical, (3) hydrolyzing the resulting compound, (4) ketalizing the carbonyl groups, (5) epoxidizing the compound, (6) opening the epoxide ring and introducing an N,N,dimethylamino-phenyl functional group into the axial position of C.sub.11, (7) deketalizing and dehydrating the resulting compound, and (8) acetylating to provide 17.alpha.-acetoxy-11.beta.-(4-N,N-dimethylaminophenyl)-19-norpregna-4,9-di ene-3,20-dione (I).Type: GrantFiled: March 30, 1995Date of Patent: July 27, 1999Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Hyun K. Kim, Pemmaraju Narasinha Rao, James E. Burdett, Jr., Carmie K. Acosta
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Patent number: 5723455Abstract: Novel antiandrogenic agents are provided. An exemplary group of compounds has the structural formula (I) ##STR1## wherein R.sup.1 through R.sup.10, a and b are as defined herein. Pharmaceutical compositions and methods for using the compounds of formula (I) to treat androgen-related clinical conditions are provided, as are methods and compositions for using the compounds as contraceptive agents.Type: GrantFiled: March 11, 1997Date of Patent: March 3, 1998Assignee: SRI InternationalInventors: Masato Tanabe, Wan-Ru Chao, Wesley K. M. Chong, David F. Crowe
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Patent number: 5710144Abstract: A C-11 substituted steroid and a method of use of a C-11 substituted steroid to treat osteoporosis.Type: GrantFiled: January 29, 1997Date of Patent: January 20, 1998Assignee: Akzo Nobel N.V.Inventors: Hubert Jan Jozef Loozen, Lodewijk Pieter Cornelis Schot, Jane Margretha Lena van der Werf-Pieters
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Patent number: 5446036Abstract: There are provided 13-alkyl-11beta-phenyl-gonanes of formula I ##STR1## wherein Z is an oxygen atom or N--OH;R.sup.2 is alpha- or beta-position methyl or ethyl;R.sup.1 is selected from heteroaryl radicals, cycloalkyl radicals, cycloalkenyl radicals, aryl radicals, alkenyl radicals, and alkyl radicals where R.sup.2 is in the alpha-position and an ethyl radical where R.sup.2 is in the beta-position; andR.sup.3 and R.sup.4 are selected from one of two different groups of substituent pairs, the group from which the selection is made being determined by the position of R.sup.2.Type: GrantFiled: November 2, 1993Date of Patent: August 29, 1995Assignee: Schering AktiengesellschaftInventors: Stefan Scholz, Eckhard Ottow, Guenter Neef, Walter Elger, Sybille Beier, Krzysztof Chwalisz
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Patent number: 5426102Abstract: Novel compounds of the general formula I ##STR1## and the pharmacologically tolerable addition salts thereof with acids are described, in which eitherIa) R.sup.11 represents a hydrogen atom in the .beta.-configuration and each of R.sup.12 and R.sup.13 represents a hydrogen atom, orIb) R.sup.11 represents a hydrogen atom in the .beta.-configuration and R.sup.12 and R.sup.13 together represent a second bond, orIc) R.sup.11 and R.sup.12 together represent a second bond and R.sup.13 represents a hydrogen atom, orId) R.sup.11 represents a hydrogen atom in the .alpha.-configuration and R.sup.12 and R.sup.13 together represent a second bond,and in Ia), Ib), Ic) or Id)X represents an oxygen atom, the hydroxyimino grouping >N.about.OH or two hydrogen atoms,R.sup.1 represents a hydrogen atom or a methyl group,R.sup.2 represents a hydroxy group, a C.sub.1 -C.sub.10 -alkoxy group or a C.sub.1 -C.sub.10 -acyloxy group, andR.sup.3 and R.sup.Type: GrantFiled: June 22, 1993Date of Patent: June 20, 1995Assignee: Schering AktiengesellschaftInventors: Wolfgang Schwede, Eckhard Ottow, Gunter Neef, Arwed Cleve, Krzysztof Chwalisz, Horst Michna
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Patent number: 5352808Abstract: A process for the preparation of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms optionally substituted by halogen or a nitrogen or oxygen function and alkenyl and alkynyl of 2 to 4 carbon atoms, R.sub.2 is alkyl of 1 to 4 carbon atoms and the A, B, C and D rings are optionally substituted by at least one member of the group consisting of optionally protected --OH or .dbd.0, halogen, alkyl and alkoxy of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms comprising reacting a compound of the formula ##STR2## wherein R.sub.1 and R.sub.2 and the A, B, C and D rings are defined as above with an oxidizing agent in the presence of water and an at least partially water-miscible solvent to obtain a compound of the formula ##STR3## wherein R.sub.1 and R.sub.Type: GrantFiled: November 5, 1992Date of Patent: October 4, 1994Assignee: Roussel UclafInventors: Jean Buendia, Michel Vivat
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Patent number: 5273971Abstract: There are provided 13-alkyl-11beta-phenyl-gonanes of formula I ##STR1## wherein Z is an oxygen atom or N--OH;R.sup.2 is alpha- or beta-position methyl or ethyl;R.sup.1 is selected from heteroaryl radicals, cycloalkyl radicals, cycloalkenyl radicals, aryl radicals, alkenyl radicals, and alkyl radicals where R.sup.2 is in the alpha-position and an ethyl radical where R.sup.2 is in the beta-position; andR.sup.3 and R.sup.4 are selected from one of two different groups of substituent pairs, the group from which the selection is made being determined by the position of R.sup.2.Type: GrantFiled: July 3, 1989Date of Patent: December 28, 1993Assignee: Schering AktiengesellschaftInventors: Stefan Scholz, Eckhard Ottow, Guenter Neef, Walter Elger, Sybille Beier, Krzysztof Chwalisz
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Patent number: 5272140Abstract: The invention relates to 11-aryl steroid derivatives, having the structure ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as described in the specificationand to processes for their preparation and to pharmaceuticals comprising these compounds.These compounds exhibit a strong anti-progestinic activity and a weak or non-existent anti-glucocorticoid activity.Type: GrantFiled: February 27, 1990Date of Patent: December 21, 1993Assignee: Akzo N.V.Inventor: Hubert J. J. Loozen
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Patent number: 5149696Abstract: Novel 19-nor-steroids of the formula ##STR1## wherein the A and B rings have a structure selected from the group consisting of ##STR2## having hormonal properties and their preparation and intermediates.Type: GrantFiled: February 23, 1990Date of Patent: September 22, 1992Assignee: Roussel UclafInventors: Andre Claussner, Lucien Nedelec, Daniel Philibert, Patrick Van De Velde
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Patent number: 5132440Abstract: A process for the production of progresterone derivatives of general formula I ##STR1## in which symbolizes a single bond or a double bond,X represents a hydrogen atom, a fluorine atom or a methyl group andV means a methylene group, an ethylene group, an ethylidene group or a vinylidene group, is described.Type: GrantFiled: July 15, 1991Date of Patent: July 21, 1992Assignee: Schering AktiengesellschaftInventors: Helmut Hauser, Hans D. Berndt
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Patent number: 5026693Abstract: Novel esters of 9.alpha.-fluoro- and chloro-corticosteroids of the formula ##STR1## wherein Y is chlorine or OR.sub.1, R.sub.1 and R.sub.2 represent an acyl group of 2-6 carbon atoms or a benzoyl group and where R.sub.1 and R.sub.2 can be the same or different in the same molecule, R.sub.3 is methyl or fluorine in either the .alpha.- or .beta.- orientation, X is chlorine or fluorine, and the C.sub.1 C.sub.2 bond can be saturated or not, especially those compounds of the formula ##STR2## wherein Y and R.sub.2 have the significance given above, are prepared by reacting the respective 9.beta.,11.beta.-epoxy compounds with hydrogen fluoride or chloride.Type: GrantFiled: May 21, 1990Date of Patent: June 25, 1991Assignee: Hovione Inter Ltd.Inventors: Ivan Villax, William Heggie, Philip R. Page
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Patent number: 4987128Abstract: Novel 10.beta.-alkynyl-steroids of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, optionally substituted alkyl and alkoxy of 1 to 8 carbon atoms, optionally substituted alkenyl and alkynyl of 2 to 8 carbon atoms, optionally substituted aryl and aralkyl, optionally esterified carboxy, dialkylamino with alkyl of 1 to 6 carbon atoms, halogen and trialkylsilyl of 1 to 7 alkyl carbon atoms, R.sub.6 and R.sub.7 taken together with the carbon atoms to which they are attached form cyclopropyl or R.sub.6 is hydrogen and R.sub.7 is R.sub.1, R.sub.1 is selected from the group consisting of hydrogen, optionally substituted alkyl of 1 to 6 carbon atoms, optionally substituted alkenyl and alkynyl of 2 to 6 carbon atoms and acetylthio, R.sub.Type: GrantFiled: February 24, 1987Date of Patent: January 22, 1991Assignee: Roussel UclafInventors: Lucien Nedelec, Francois Nique, Anne-Marie Moura
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Patent number: 4956482Abstract: Known pregnane derivatives are prepared by esterification of know androstane derivatives to give new esters of Formula III ##STR1## wherein in each case symbolizes a single bond or a double bond,n is 1 or 2,R.sub.1 is hydrogen or methyl,R.sub.2 is hydrogen or formyl, andR.sub.3 is chlorine, hydroxy or an alkanoyloxy group of up to 6 carbon atoms,and reaction of the latter with Ag(I) and formic acid.Type: GrantFiled: March 20, 1989Date of Patent: September 11, 1990Assignee: Schering AktiengesellschaftInventors: Helmut Hofmeister, Klaus Annen, Henry Laurent, Rudolf Wiechert
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Patent number: 4954490Abstract: A 11.beta.-aryl-19-norprogesterone steroid of the formula: ##STR1## wherein (i) R.sup.1 is H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, OH, OC(O)CH.sub.3, or OC(O)R.sup.5, wherein R.sup.5 is C.sub.2-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl or aryl, R.sub.2 is H, R.sup.3 is H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkynyl, R.sup.4 is H, CH.sub.3, F or Cl, R.sup.6 is H, (CH.sub.3).sub.2 N, CH.sub.3 O, CH.sub.3 CO, CH.sub.3 S, CH.sub.3 SO, CH.sub.3 SO.sub.2, and X is O or NOCH.sub.3 ; or(ii) R.sup.1 and R.sup.2 taken together are a carbon-carbon bond and R.sup.3, R.sup.4, R.sup.6 and X are as defined above; or(iii) R.sup.1 and R.sup.3 taken together are --CH.sub.2 -- or --N.dbd.N--CH.sub.2 --, R.sup.2 is H and R.sup.4, R.sup.6 and X are as defined above; or(iv) R.sup.2 and R.sup.3 taken together are .dbd.CH.sub.2 and R.sup.1, R.sup.4, R.sup.6 and X are as defined above.Type: GrantFiled: June 23, 1988Date of Patent: September 4, 1990Assignee: Research Triangle InstituteInventors: C. Edgar Cook, Mansukh C. Wani, Y.-W Lee, Jerry R. Reel, Douglas Rector
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Patent number: 4921638Abstract: The invention is the compound 17.beta.-cyano-9.alpha., 17.alpha.-dihydroxyandrost-4-en-3-one (I) which is particularly useful as an intermediate in the production of the 17.alpha.-halo silyl ethers (II).Type: GrantFiled: October 3, 1988Date of Patent: May 1, 1990Assignee: The Upjohn CompanyInventors: Douglas A. Livingston, Bruce A. Pearlman, Scott Denmark, Joel E. Huber
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Patent number: 4913852Abstract: Compounds obtained from the associative synthesis of sulfur-containing or sulfur-free amino acids with derivatives of .DELTA.-4-pregnene-3,20-dione or with derivatives of .DELTA.-1,4-pregnadiene-3,20-dione of the general formulas (I), (II) and (III), having glucocorticoidal and anti-inflammatory properties have been prepared and tested. Pharmaceutical compositions, medicaments containing them as well as their applications are claimed, particularly in the cutaneous and ophthalmic fields.Type: GrantFiled: February 24, 1988Date of Patent: April 3, 1990Inventors: Catherine Milioni, Constantin Efthyimiopoulos, Bernard Koch, Louis Jung, Jean Jung