Unsaturation Between The 4- And 5-positions (e.g., 17-alpha-hydroxy Progesterones, Etc.) Patents (Class 552/595)
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Patent number: 11986484Abstract: The present invention relates to certain cortexolone derivatives of formula (I) and the use of the same as antitumor active ingredients for the curative or adjuvant, or neoadjuvant or palliative treatment of precancerous lesions, dysplasias, metaplasias and tumor diseases, including malignant neoplasias and metastasis. The present invention also relates to pharmaceutical compositions comprising cortexolone derivatives of formula (I) as active ingredients and at least one physiologically acceptable excipient, and to the use of the pharmaceutical compositions as antitumor medicinal products.Type: GrantFiled: December 19, 2022Date of Patent: May 21, 2024Assignee: COSMO TECHNOLOGIES LIMITEDInventor: Mara Gerloni
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Patent number: 11883415Abstract: The present disclosure provides high concentration formulations of cortexolone-17?-propionate suitable for treating alopecia.Type: GrantFiled: November 23, 2021Date of Patent: January 30, 2024Assignee: Cassiopea S.P.A.Inventor: Luigi Maria Longo
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Patent number: 11712443Abstract: The present invention relates to certain cortexolone derivatives of formula (I) and the use of the same as antitumor active ingredients for the curative or adjuvant, or neoadjuvant or palliative treatment of precancerous lesions, dysplasias, metaplasias and tumor diseases, including malignant neoplasias and metastasis. The present invention also relates to pharmaceutical compositions comprising cortexolone derivatives of formula (I) as active ingredients and at least one physiologically acceptable excipient, and to the use of the pharmaceutical compositions as antitumor medicinal products.Type: GrantFiled: April 6, 2021Date of Patent: August 1, 2023Assignee: COSMO TECHNOLOGIES LIMITEDInventor: Mara Gerloni
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Patent number: 9433628Abstract: The present invention refers to a new enzymatic process for obtaining 17?-monoesters of cortexolone and/or its 9,11-dehydroderivatives starting from the corresponding 17?,21-diesters which comprises an enzymatic alcoholysis reaction. Furthermore, the present invention refers to new crystalline forms of cortexolone 17?-propionate and 9,11-dehydro-cortexolone 17?-butanoate.Type: GrantFiled: November 7, 2013Date of Patent: September 6, 2016Assignee: Cassiopea SPAInventors: Mauro Ajani, Luigi Moro
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Patent number: 9221870Abstract: The present invention relates to novel crystalline Form II of 17?-acetoxy-21-methoxy-11?-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione, (also known as CDB-4124), processes for the preparation thereof and pharmaceutical compositions comprising it. Form II can be crystallized from different medium such as esters of C1-C4 alcohols and carboxylic acids, ketones, cyclohexane, acetonitrile, dimethylformamide, dimethyl sulfoxide, water and any mixture thereof.Type: GrantFiled: August 5, 2010Date of Patent: December 29, 2015Assignee: Richter Gedeon Nyrt.Inventors: Attila Balázs, János Csörgei, Ádám Demeter, Csaba Sánta
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Patent number: 8785427Abstract: The present invention refers to a new enzymatic process for obtaining 17?-monoesters of cortexolone and/or its 9,11-dehydroderivatives starting from the corresponding 17?,21-diesters which comprises an enzymatic alcoholysis reaction. Furthermore, the present invention refers to new crystalline forms of cortexolone 17?-propionate and 9,11-dehydro-cortexolone 17?-butanoate.Type: GrantFiled: July 24, 2008Date of Patent: July 22, 2014Assignee: Cosmo Dermatos SrlInventors: Ajani Mauro, Moro Luigi
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Publication number: 20140179654Abstract: The present invention refers to a new enzymatic process for obtaining 17?-monoesters of cortexolone and/or its 9,11-dehydroderivatives starting from the corresponding 17?,21-diesters which comprises an enzymatic alcoholysis reaction. Furthermore, the present invention refers to new crystalline forms of cortexolone 17?-propionate and 9,11-dehydro-cortexolone 17?-butanoate.Type: ApplicationFiled: November 7, 2013Publication date: June 26, 2014Applicant: Cosmo SPAInventors: Mauro Ajani, Luigi Moro
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Patent number: 8735381Abstract: The present invention relates to methods of administering compositions comprising a progesterone receptor antagonist for use in treating estrogen-dependent conditions. The invention is also directed to methods for treating pain associated with endometriosis. The compositions may be administered to females with endometriosis as well as to females undergoing estrogen and/or selective estrogen receptor modulator (SERM) therapy. In certain embodiments, the invention provides a method for suppressing endometrial proliferation.Type: GrantFiled: April 2, 2013Date of Patent: May 27, 2014Assignee: Repros Therapeutics Inc.Inventor: Joseph S. Podolski
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Patent number: 8569276Abstract: The present invention relates, inter alia, to compounds having the general formula: in which R1, R2, R3, R4 and X are as defined by the present specification. In addition to providing the compounds of Formula I, the present invention provides methods wherein the compounds of Formula I are advantageously used, inter alia, to antagonize endogenous progesterone; to induce menses; to treat endometriosis; to treat dysmenorrhea; to treat endocrine hormone-dependent tumors; to treat meningiomas; to treat uterine leiomyomas; to treat uterine fibroids; to inhibit uterine endometrial proliferation; to induce cervical ripening; to induce labor; and for contraception.Type: GrantFiled: February 28, 2005Date of Patent: October 29, 2013Assignee: The United States of America, as represented by the Secretary, 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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Publication number: 20130274234Abstract: The subject matter of the instant invention is pertinent to the field of treatment of hormone-dependent conditions. New compounds and methods for treating these conditions are disclosed. Embodiments of the instant invention disclose methods for treating endometriosis, dysmenorrhea, breast cancer, uterine fibroids and endometrial hyperproliferation.Type: ApplicationFiled: September 8, 2011Publication date: October 17, 2013Applicant: REPROS THERAPEUTICS INC.Inventors: Joseph S. Podolski, Ronald D. Wiehle
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Publication number: 20130196962Abstract: The present invention relates to compounds and methods which may be useful as treatments of neuromuscular diseases such as muscular dystrophy, and as inhibitors of NF-?B for the treatment or prevention of muscular wasting disease, including muscular dystrophy.Type: ApplicationFiled: April 5, 2011Publication date: August 1, 2013Applicant: VALIDUS BIOPHARMA, INCInventors: John M. McCall, Eric Hoffman, Kanneboyina Nagaraju
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Patent number: 8426394Abstract: The present invention relates to methods of administering compositions comprising a progesterone receptor antagonist for use in treating estrogen-dependent conditions. The invention is also directed to methods for treating pain associated with endometriosis. The compositions may be administered to females with endometriosis as well as to females undergoing estrogen and/or selective estrogen receptor modulator (SERM) therapy. In certain embodiments, the invention provides a method for suppressing endometrial proliferation.Type: GrantFiled: April 27, 2009Date of Patent: April 23, 2013Assignee: Repros Therapeutics Inc.Inventor: Joseph S. Podolski
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Publication number: 20130018027Abstract: The subject matter of the instant invention is pertinent to the field of treatment of hormone-dependent conditions. New compounds and methods for treating these conditions are disclosed. Embodiments of the instant invention disclose methods for treating endometriosis, dysmenorrhea, breast cancer, uterine fibroids and endometrial hyperproliferation.Type: ApplicationFiled: December 23, 2010Publication date: January 17, 2013Applicant: REPROS THERAPEUTICS INC.Inventors: Joseph S. Podolski, Ronald D. Wiehle
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Publication number: 20120149667Abstract: A stable and/or synergistic pharmaceutical composition including: a) predinisolone metasulfobenzoate (PMSB) or its acceptable salts, preferably prednisolone metasulfobenzoate sodium and b) 5-ASA, derivatives or pharmaceutically acceptable salts thereof, which is suitable for rectal administration.Type: ApplicationFiled: August 25, 2010Publication date: June 14, 2012Applicants: DISPHAR INTERNATIONAL BV, NORDIC PHARMAInventors: Hans Schram, Michael Ikechukwu Ugwoke, Laura Buttafoco
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Publication number: 20120142655Abstract: The present invention relates to novel crystalline Form II of 17?-acetoxy-21-methoxy-11?-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione, (also known as CDB-4124), processes for the preparation thereof and pharmaceutical compositions comprising it. Form II can be crystallized from different medium such as esters of C1-C4 alcohols and carboxylic acids, ketones, cyclohexane, acetonitrile, dimethylformamide, dimethyl sulfoxide, water and any mixture thereof.Type: ApplicationFiled: August 5, 2010Publication date: June 7, 2012Inventors: Attila Balázs, János Csörgei, Ádám Demeter, Csaba Sánta
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Patent number: 8183402Abstract: The present invention relates to a process for the synthesis of the 17-acetoxy-11?-[4-(dimethylamino)-phenyl]-21-methoxy-19-norpregna-4,9-dien-3,20-dione of formula (I): from 3,3-[1,2-etandiyl-bis(oxy)]-oestr-5(10),9(11)-dien-17-one of formula (II):Type: GrantFiled: June 19, 2008Date of Patent: May 22, 2012Assignee: Richter Gedeon Nyrt.Inventors: József Bódi, György Visky, János Széles, Sándor Mahó, Csaba Sánta, János Csörgei, Zoltán Tuba, László Terdy, Csaba Molnár, Antal Aranyi, Zoltán Horváth, Gábor Balogh
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Patent number: 8058266Abstract: The present invention describes linking a therapeutic agent to a compound which is known to be naturally concentrated in a tissue affected by, or that is causing, a disease, to create a prodrug for treatment of the disease. Embodiments of the present invention include a new class of carotenoid-linked drugs to treat such blinding retinal disease such as age-related macular degeneration, retinoblastoma, and diabetic macular edema. For example, the present invention comprises a method for the treatment of a disorder of the eye comprising linking a therapeutic agent to a xanthophyll carotenoid to create a prodrug, and administering a therapeutically effective amount of the prodrug to an individual in need of treatment. Provided are prodrugs for treatment of retinoblastoma, cystoid macular edema (CME), exudative age-related macular degeneration (AMD), diabetic retinopathy, diabetic macular edema, or inflammatory disorders.Type: GrantFiled: July 13, 2007Date of Patent: November 15, 2011Assignee: The University of Georgia Research Foundation, IncInventors: Dennis Michael Marcus, Chung Kwang Chu
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Patent number: 8044223Abstract: The present invention are two crystalline salts, 17?-acetoxy-21-methoxy-11?-(4-,N,N-dimethylaminophenyl)-19 norpregna-4,9-diene-3,20-dione hydrochloride and 17?-acetoxy-21-methoxy-11?-(4-,N,N-dimethylaminophenyl)-19 norpregna-4,9-diene-3,20-dione hydrobromide, of the corresponding free base which is an amorphous solid.Type: GrantFiled: April 1, 2004Date of Patent: October 25, 2011Assignee: Bridge Organics Co.Inventor: Verlan H. VanRheenen
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Publication number: 20110237811Abstract: Stabilized, 17-substituted hydrocortisone containing compositions and methods of manufacture are disclosed. Isomerization of the hydrocortisone component of topical steroid compositions is markedly reduced by including an omega-6 acid component in the form of a free acid or as a compound such as an ester. Specifically disclosed are methods for preventing the isomerization of hydrocortisone 17-butyrate into hydrocortisone 21-butyrate through the use of safflower oil.Type: ApplicationFiled: June 8, 2011Publication date: September 29, 2011Inventor: Pravin M. Patel
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Publication number: 20110092472Abstract: The present invention refers to a new enzymatic process for obtaining 17?-monoesters of cortexolone and/or its 9,11-dehydroderivatives starting from the corresponding 17?,21-diesters which comprises an enzymatic alcoholysis reaction. Furthermore, the present invention refers to new crystalline forms of cortexolone 17?-propionate and 9,11-dehydro-cortexolone 17?-butanoate.Type: ApplicationFiled: July 24, 2008Publication date: April 21, 2011Applicant: COSMO SPAInventors: Mauro Ajani, Luigi Moro
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Publication number: 20100273759Abstract: Described herein are compounds which exhibit progesterone antagonistic effects and methods of treating cancer using such compounds.Type: ApplicationFiled: March 29, 2010Publication date: October 28, 2010Inventors: Klaus Nickisch, James Cessac, Kesavaram Narkunan, Baishakhi Das
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Patent number: 7759330Abstract: 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: August 7, 2006Date of Patent: July 20, 2010Assignee: 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: 7749987Abstract: A method of achieving contraception in a woman which comprises administering orally to said woman an estroprogestative composition comprising nomegestrol acetate and an estrogen is provided.Type: GrantFiled: January 3, 2007Date of Patent: July 6, 2010Assignee: Laboratorie TheramekInventors: Jacques Paris, Jean-Louis Thomas, Michel Lanquetin, Anny Lanquetin, legal representative, Jean-Philippe Lanquetin, legal representative
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Publication number: 20100041906Abstract: The present invention concerns a method for the controlled precipitation of organic compounds giving crystals with a very small average size and a very narrow size distribution.Type: ApplicationFiled: January 26, 2007Publication date: February 18, 2010Inventors: Huibert Albertus Van Boxtel, Servatius Hubertus Johannes Wilhelmus Leenen, Matheus Lambertus Spapens
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Patent number: 7495115Abstract: Conjugates comprising one or more steroids conjugated with one or more mammalian proteins are disclosed. The conjugates are useful for diagnosis or treatment of solid cancer and haematological malignancies. Further the conjugates exhibits a synergistic action together with a cytoskeleton acting drug such as Taxol®, which enable the treatment of cancers that otherwise would be non responsive to Taxol®.Type: GrantFiled: July 14, 2003Date of Patent: February 24, 2009Assignee: Bionature E.A., Ltd.Inventor: Elias Castanas
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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: 6768014Abstract: A compound having general formula (I) 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: June 27, 2002Date of Patent: July 27, 2004Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Hyun Koo Kim, Pemmaraju N. Rao, James W. Cessac, Anne Marie Simmons
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Patent number: 6365582Abstract: Thiol esters of S-substituted 11&bgr;-benzaldoxime-estra-4,9-dien-carboxylic acids of the formula I their pharmaceutically acceptable salts, a method for their synthesis and pharmaceutical preparations containing these compounds are described. These compounds bind to progesterone receptors and have distinctly reduced anti-glucocorticoid action.Type: GrantFiled: August 22, 2000Date of Patent: April 2, 2002Assignee: Jenapharm GmbH & Co. KGInventors: Gerd Schubert, Sven Ring, Guenther Kaufmann, Walter Elger, Birgit Schneider
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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: 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: 5723638Abstract: The invention is drawn to a process for the preparation of a steroid of the formula ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1 to 4 carbon atoms, R.sub.2 is alkyl of 1 to 4 carbon atoms and theo A, B, C, and D ring system has at least one double bond and is optionally substituted by at least one optionally protected hydroxy, optionally protected keto, halogen, alkyl and alkoxy of 1 to 4 carbon atoms, and alkenyl and alkynyl of 2 to 4 carbon atoms by reacting the corresponding 17-ketosteroid with a compound of the formula ##STR2## and then by reacting the resulting compound with an aryl sulfenyl halide. The intermediate produced then undergoes rearrangement followed by epimerization with a strong base to obtain a mixture of the corresponding sulfoxide diastereoisomers which is reacted with a thiophilic compound. The intermediate produced undergoes acid hydrolysis to provide the compound of formula I.Type: GrantFiled: June 26, 1995Date of Patent: March 3, 1998Assignee: Roussel UclafInventors: Robert Lett, Oleg Melnyk
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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: 5710293Abstract: The present invention relates to a method of using a perchloric acid catalyzed reaction to make acyl derivatives of norprogesterone compounds and, in particular, 16-methylene-17.alpha.-hydroxy-19-norpregn-4-ene-3,20-dione.Type: GrantFiled: October 13, 1995Date of Patent: January 20, 1998Assignee: The Population Council, Center for Biomedical ResearchInventor: Fang Li
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Patent number: 5616742Abstract: Described is a process for the regioselective dehydration of 11-hydroxy steroids using PCl.sub.5, PCl.sub.3, POCl.sub.3 or either SO.sub.2 Cl.sub.2 and imidazole, or PPh.sub.3 and CCl.sub.4. The disclosed process selectively forms .DELTA..sup.9,11 steroids from either 11-.alpha.- or 11-.beta.-hydroxy steroids, and can also be used for the one-step conversion of 11,21-dihydroxy steroids to 21-chloro-.DELTA..sup.9,11 steroids.Also disclosed are processes for the regioselective conversion of 11-.beta.-chloro steroids to .DELTA..sup.9,11 steroids, and for regioselectively converting an 11,17,21-trihydroxy streoid to a 21-chloro-11,17-dihydroxy steroid.Type: GrantFiled: May 22, 1995Date of Patent: April 1, 1997Assignee: Schering CorporationInventors: Xiaoyong Fu, Tiruvettipuram K. Thiruvengadam, Chou-Hong Tann, Cesar Colon
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Patent number: 5608093Abstract: Corticoid 17-alkyl carbonate 21-carboxylic and carbonic esters of the formula I ##STR1## are described in which A is CHOH and CHCl, CH.sub.2, C.dbd.O or 9(11) double bond; Y is H, F or Cl; Z is H, F or CH.sub.3 ; R(1) is aryl or hetaryl; n and m are zero or 1; R(2) is alkyl or --(CH.sub.2).sub.2 --OCH.sub.3 ; R(3) is H or methyl. They are obtained by reacting a compound of the formula II, ##STR2## in which R(5) is OH, with an activated carboxylic acid of the formula III,R(6)--CO--(O).sub.n --(X)--R(1) III.The compounds I have a very strong local and topical antiinflammatory action and exhibit a very good ratio of local to systemic antiinflammatory effects, which ratio is often markedly superior to that of analogous corticoid 17-alkyl carbonate 21-esters which do not carry any aryl or heteraryl group in the 21-ester radical.Type: GrantFiled: August 25, 1994Date of Patent: March 4, 1997Assignee: Hoechst AktiengesellschaftInventors: Ulrich Stache, Hans-Georg Alpermann, Walter D urckheimer, Manfred Bohn
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Patent number: 5567830Abstract: A method for the preparation of an acetylenic alcohol by reaction of 1,2-dibromoethylene with an alkyl, aryl an heteroaryl lithium in an inert solvent, followed by reaction with a carbonyl-containing compound to give an acetylenic alcohol is disclosed.Type: GrantFiled: February 14, 1994Date of Patent: October 22, 1996Assignee: Cocensys, Inc.Inventor: Ravindra B. Upasani
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Patent number: 5502222Abstract: Described is a process for the regioselective dehydration of 11-hydroxy steroids using PCl.sub.5, PCl.sub.3, POCl.sub.3 or either SO.sub. Cl.sub.2 and imidazole, or PPh.sub.3 and CCl.sub.4. The disclosed process selectively forms .increment..sup.9,11 steroids from either 11-.alpha.- or 11-.beta.-hydroxy steroids, and can also be used for the one-step conversion of 11,21-dihydroxy steroids to 21-chloro-.increment..sup.9,11 steroids.Type: GrantFiled: June 1, 1994Date of Patent: March 26, 1996Assignee: Schering CorporationInventors: Xiaoyong Fu, Tiruvettipuram K. Thiruvengadam, Chou-Hong Tann, Junning Lee, Cesar Colon
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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: 5412091Abstract: A compound of the formula ##STR1## in which ##STR2## is either a 3-keto-.DELTA.4-system or a 3-keto -.DELTA.1,4-system or a 3-OR.sub.4 - .DELTA.5-system in which R.sub.4 is hydrogen or a protector group of hydroxy, R is methyl --CH.sub.2 OH or --CH.sub.2 OR', in which R' is a protector group of hydroxy, R.sub.1 and R'.sub.1 are individually selected from the group consisting of methyl, a branched alkyl not possessing hydrogen in the .beta. position of 5 to 8 carbon atoms, aryl of up to 10 carbon atoms, heteroaryl of up to 10 carbon atoms and at least one heteroatom chosen from nitrogen, sulfur and oxygen and benzyl, n and m, are individually numbers 0 or 1, R.sub.2 and R.sub.3 are hydrogen or R.sub.2 is fluorine and R.sub.3 is formyloxy or acetyloxy and the dotted lines in position 9(11) indicate the optional presence of a second bond which is useful for the preparation of compounds of formula A.Type: GrantFiled: July 1, 1993Date of Patent: May 2, 1995Assignee: Roussel UclafInventors: Jean Boivin, Christine Chauvet, Samir Zard
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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: 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: 4948533Abstract: The present invention relates to 21-(3-carboxy-1-oxopropoxy) -17.alpha.-hydroxy-11.alpha.-(3,3-dimethyl-1-oxobutoxy)pregna-1,4-diene-3, 20 dione and pharmaceutically acceptable salts thereof which are useful steroid prodrugs.Type: GrantFiled: February 16, 1989Date of Patent: August 14, 1990Assignee: The Upjohn CompanyInventors: John M. Braughler, Edward D. Hall, Wendell Wierenga, John M. McCall
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Patent number: 4933332Abstract: 11-Desoxy-17.alpha.-hydroxycorticosterone derivatives of the general formula: ##STR1## wherein R is --OC(CH.sub.2).sub.n C.sub.6 H.sub.4 N(CH.sub.2 CH.sub.2 Cl).sub.2, n=1,3.Type: GrantFiled: September 30, 1988Date of Patent: June 12, 1990Inventors: Kira N. Kurdjumova, Elizaveta N. Shkodinskaya, Ljudmila P. Sushinina, Valentina P. Yaguzhinskaya, Nina D. Lagova, Zoya P. Sofiina, Irina M. Valueva, Petr V. Lopatin, Margarita A. Krasnova, Anatoly B. Syrkin, Ljudmila M. Mikhailova
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Patent number: 4929395Abstract: C.sub.16 -unsaturated corticoids are readily transformed to the corresponding 16.alpha.-methyl-17.alpha.-hydroxy corticoids by use of a .DELTA..sup.17 (.sup.20)-20-silyl ether.Type: GrantFiled: November 14, 1986Date of Patent: May 29, 1990Assignee: The Upjohn CompanyInventors: Verlan H. VanRheenen, Joel E. Huber
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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: 4920216Abstract: This invention concerns a method of substituting a chlorine atom for a predetermined hydrogen atom located within an organic compound which comprises contacting the organic compound containing the predetermined hydrogen atom with an esterifying agent comprising a pyridine ring or a substituted or fused ring derivative of a pyridine ring so as to produce an ester and treating the ester with a chlorinating agent so as to substitute the chlorine atom for the predetermined hydrogen atom. The ester comprises the pyridine ring or the substituted or fused ring derivative of the pyridine ring so positioned within the ester with respect to the predetermined hydrogen atom that a chlorine atom attached to the nitrogen atom of the pyridine ring or substituted or fused ring derivative of the pyridine ring reacts with the predetermined hydrogen atom.Type: GrantFiled: May 28, 1987Date of Patent: April 24, 1990Assignee: The Trustees of Columbia in the City of New YorkInventors: Ronald Breslow, Michael Brandl, Alan D. Adams, Jurgen Hunger
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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