Unsaturation Between The 4- And 5-positions (e.g., 17-alpha-hydroxy Progesterones, Etc.) Patents (Class 552/595)
  • Patent number: 11986484
    Abstract: 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: Grant
    Filed: December 19, 2022
    Date of Patent: May 21, 2024
    Assignee: COSMO TECHNOLOGIES LIMITED
    Inventor: Mara Gerloni
  • Patent number: 11883415
    Abstract: The present disclosure provides high concentration formulations of cortexolone-17?-propionate suitable for treating alopecia.
    Type: Grant
    Filed: November 23, 2021
    Date of Patent: January 30, 2024
    Assignee: Cassiopea S.P.A.
    Inventor: Luigi Maria Longo
  • Patent number: 11712443
    Abstract: 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: Grant
    Filed: April 6, 2021
    Date of Patent: August 1, 2023
    Assignee: COSMO TECHNOLOGIES LIMITED
    Inventor: Mara Gerloni
  • Patent number: 9433628
    Abstract: 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: Grant
    Filed: November 7, 2013
    Date of Patent: September 6, 2016
    Assignee: Cassiopea SPA
    Inventors: Mauro Ajani, Luigi Moro
  • Patent number: 9221870
    Abstract: 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: Grant
    Filed: August 5, 2010
    Date of Patent: December 29, 2015
    Assignee: Richter Gedeon Nyrt.
    Inventors: Attila Balázs, János Csörgei, Ádám Demeter, Csaba Sánta
  • Patent number: 8785427
    Abstract: 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: Grant
    Filed: July 24, 2008
    Date of Patent: July 22, 2014
    Assignee: Cosmo Dermatos Srl
    Inventors: Ajani Mauro, Moro Luigi
  • Publication number: 20140179654
    Abstract: 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: Application
    Filed: November 7, 2013
    Publication date: June 26, 2014
    Applicant: Cosmo SPA
    Inventors: Mauro Ajani, Luigi Moro
  • Patent number: 8735381
    Abstract: 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: Grant
    Filed: April 2, 2013
    Date of Patent: May 27, 2014
    Assignee: Repros Therapeutics Inc.
    Inventor: Joseph S. Podolski
  • Patent number: 8569276
    Abstract: 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: Grant
    Filed: February 28, 2005
    Date of Patent: October 29, 2013
    Assignee: The United States of America, as represented by the Secretary, Department of Health and Human Services
    Inventors: Hyun K. Kim, Richard P. Blye, Pemmaraju N. Rao, James W. Cessac, Carmie K. Acosta
  • Publication number: 20130274234
    Abstract: 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: Application
    Filed: September 8, 2011
    Publication date: October 17, 2013
    Applicant: REPROS THERAPEUTICS INC.
    Inventors: Joseph S. Podolski, Ronald D. Wiehle
  • Publication number: 20130196962
    Abstract: 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: Application
    Filed: April 5, 2011
    Publication date: August 1, 2013
    Applicant: VALIDUS BIOPHARMA, INC
    Inventors: John M. McCall, Eric Hoffman, Kanneboyina Nagaraju
  • Patent number: 8426394
    Abstract: 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: Grant
    Filed: April 27, 2009
    Date of Patent: April 23, 2013
    Assignee: Repros Therapeutics Inc.
    Inventor: Joseph S. Podolski
  • Publication number: 20130018027
    Abstract: 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: Application
    Filed: December 23, 2010
    Publication date: January 17, 2013
    Applicant: REPROS THERAPEUTICS INC.
    Inventors: Joseph S. Podolski, Ronald D. Wiehle
  • Publication number: 20120149667
    Abstract: 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: Application
    Filed: August 25, 2010
    Publication date: June 14, 2012
    Applicants: DISPHAR INTERNATIONAL BV, NORDIC PHARMA
    Inventors: Hans Schram, Michael Ikechukwu Ugwoke, Laura Buttafoco
  • Publication number: 20120142655
    Abstract: 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: Application
    Filed: August 5, 2010
    Publication date: June 7, 2012
    Inventors: Attila Balázs, János Csörgei, Ádám Demeter, Csaba Sánta
  • Patent number: 8183402
    Abstract: 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: Grant
    Filed: June 19, 2008
    Date of Patent: May 22, 2012
    Assignee: 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
  • Patent number: 8058266
    Abstract: 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: Grant
    Filed: July 13, 2007
    Date of Patent: November 15, 2011
    Assignee: The University of Georgia Research Foundation, Inc
    Inventors: Dennis Michael Marcus, Chung Kwang Chu
  • Patent number: 8044223
    Abstract: 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: Grant
    Filed: April 1, 2004
    Date of Patent: October 25, 2011
    Assignee: Bridge Organics Co.
    Inventor: Verlan H. VanRheenen
  • Publication number: 20110237811
    Abstract: 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: Application
    Filed: June 8, 2011
    Publication date: September 29, 2011
    Inventor: Pravin M. Patel
  • Publication number: 20110092472
    Abstract: 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: Application
    Filed: July 24, 2008
    Publication date: April 21, 2011
    Applicant: COSMO SPA
    Inventors: Mauro Ajani, Luigi Moro
  • Publication number: 20100273759
    Abstract: Described herein are compounds which exhibit progesterone antagonistic effects and methods of treating cancer using such compounds.
    Type: Application
    Filed: March 29, 2010
    Publication date: October 28, 2010
    Inventors: Klaus Nickisch, James Cessac, Kesavaram Narkunan, Baishakhi Das
  • Patent number: 7759330
    Abstract: 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: Grant
    Filed: August 7, 2006
    Date of Patent: July 20, 2010
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Hyun K. Kim, Richard P. Blye, Pemmaraju N. Rao, James W. Cessac, Carmie K. Acosta
  • Patent number: 7749987
    Abstract: 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: Grant
    Filed: January 3, 2007
    Date of Patent: July 6, 2010
    Assignee: Laboratorie Theramek
    Inventors: Jacques Paris, Jean-Louis Thomas, Michel Lanquetin, Anny Lanquetin, legal representative, Jean-Philippe Lanquetin, legal representative
  • Publication number: 20100041906
    Abstract: 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: Application
    Filed: January 26, 2007
    Publication date: February 18, 2010
    Inventors: Huibert Albertus Van Boxtel, Servatius Hubertus Johannes Wilhelmus Leenen, Matheus Lambertus Spapens
  • Patent number: 7495115
    Abstract: 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: Grant
    Filed: July 14, 2003
    Date of Patent: February 24, 2009
    Assignee: Bionature E.A., Ltd.
    Inventor: Elias Castanas
  • Patent number: 7087591
    Abstract: 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: Grant
    Filed: February 23, 2005
    Date of Patent: August 8, 2006
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Hyun K. Kim, Richard P. Blye, Pemmaraju N. Rao, James W. Cessac, Carmie K. Acosta
  • Patent number: 6900193
    Abstract: 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: Grant
    Filed: March 17, 2000
    Date of Patent: May 31, 2005
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Hyun K. Kim, Richard P. Blye, Pemmaraju N. Rao, James W. Cessac, Carmie K. Acosta, Anne Marie Simmons
  • Patent number: 6861415
    Abstract: 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: Grant
    Filed: April 30, 1997
    Date of Patent: March 1, 2005
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Hyun K. Kim, Richard P. Blye, Pemmaraju N. Rao, James W. Cessac, Carmie K. Acosta
  • Patent number: 6768014
    Abstract: 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: Grant
    Filed: June 27, 2002
    Date of Patent: July 27, 2004
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Hyun Koo Kim, Pemmaraju N. Rao, James W. Cessac, Anne Marie Simmons
  • Patent number: 6365582
    Abstract: 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: Grant
    Filed: August 22, 2000
    Date of Patent: April 2, 2002
    Assignee: Jenapharm GmbH & Co. KG
    Inventors: Gerd Schubert, Sven Ring, Guenther Kaufmann, Walter Elger, Birgit Schneider
  • Publication number: 20020025951
    Abstract: A compound having the general formula: 1
    Type: Application
    Filed: May 24, 1999
    Publication date: February 28, 2002
    Inventors: HYUN K. KIM, RICHARD P. BLYE, PEMMARAJU N. RAO, JAMES W. CESSAC, CARMIE K. ACOSTA
  • Patent number: 6037339
    Abstract: A C-11 substituted steroid and a method of use of a C-11 substituted steroid to treat osteoporosis.
    Type: Grant
    Filed: January 16, 1998
    Date of Patent: March 14, 2000
    Assignee: Akzo Nobel N.V.
    Inventors: Hubert Jan Jozef Loozen, Lodewijk Pieter Cornelis Schot, Jane Margretha Lena van der Werf-Pieters
  • Patent number: 5723638
    Abstract: 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: Grant
    Filed: June 26, 1995
    Date of Patent: March 3, 1998
    Assignee: Roussel Uclaf
    Inventors: Robert Lett, Oleg Melnyk
  • Patent number: 5710144
    Abstract: A C-11 substituted steroid and a method of use of a C-11 substituted steroid to treat osteoporosis.
    Type: Grant
    Filed: January 29, 1997
    Date of Patent: January 20, 1998
    Assignee: Akzo Nobel N.V.
    Inventors: Hubert Jan Jozef Loozen, Lodewijk Pieter Cornelis Schot, Jane Margretha Lena van der Werf-Pieters
  • Patent number: 5710293
    Abstract: 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: Grant
    Filed: October 13, 1995
    Date of Patent: January 20, 1998
    Assignee: The Population Council, Center for Biomedical Research
    Inventor: Fang Li
  • Patent number: 5616742
    Abstract: 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: Grant
    Filed: May 22, 1995
    Date of Patent: April 1, 1997
    Assignee: Schering Corporation
    Inventors: Xiaoyong Fu, Tiruvettipuram K. Thiruvengadam, Chou-Hong Tann, Cesar Colon
  • Patent number: 5608093
    Abstract: 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: Grant
    Filed: August 25, 1994
    Date of Patent: March 4, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ulrich Stache, Hans-Georg Alpermann, Walter D urckheimer, Manfred Bohn
  • Patent number: 5567830
    Abstract: 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: Grant
    Filed: February 14, 1994
    Date of Patent: October 22, 1996
    Assignee: Cocensys, Inc.
    Inventor: Ravindra B. Upasani
  • Patent number: 5502222
    Abstract: 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: Grant
    Filed: June 1, 1994
    Date of Patent: March 26, 1996
    Assignee: Schering Corporation
    Inventors: Xiaoyong Fu, Tiruvettipuram K. Thiruvengadam, Chou-Hong Tann, Junning Lee, Cesar Colon
  • Patent number: 5446036
    Abstract: 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: Grant
    Filed: November 2, 1993
    Date of Patent: August 29, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: Stefan Scholz, Eckhard Ottow, Guenter Neef, Walter Elger, Sybille Beier, Krzysztof Chwalisz
  • Patent number: 5412091
    Abstract: 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: Grant
    Filed: July 1, 1993
    Date of Patent: May 2, 1995
    Assignee: Roussel Uclaf
    Inventors: Jean Boivin, Christine Chauvet, Samir Zard
  • Patent number: 5352808
    Abstract: 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: Grant
    Filed: November 5, 1992
    Date of Patent: October 4, 1994
    Assignee: Roussel Uclaf
    Inventors: Jean Buendia, Michel Vivat
  • Patent number: 4956482
    Abstract: 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: Grant
    Filed: March 20, 1989
    Date of Patent: September 11, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Hofmeister, Klaus Annen, Henry Laurent, Rudolf Wiechert
  • Patent number: 4948533
    Abstract: 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: Grant
    Filed: February 16, 1989
    Date of Patent: August 14, 1990
    Assignee: The Upjohn Company
    Inventors: John M. Braughler, Edward D. Hall, Wendell Wierenga, John M. McCall
  • Patent number: 4933332
    Abstract: 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: Grant
    Filed: September 30, 1988
    Date of Patent: June 12, 1990
    Inventors: 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
  • Patent number: 4929395
    Abstract: 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: Grant
    Filed: November 14, 1986
    Date of Patent: May 29, 1990
    Assignee: The Upjohn Company
    Inventors: Verlan H. VanRheenen, Joel E. Huber
  • Patent number: 4921638
    Abstract: 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: Grant
    Filed: October 3, 1988
    Date of Patent: May 1, 1990
    Assignee: The Upjohn Company
    Inventors: Douglas A. Livingston, Bruce A. Pearlman, Scott Denmark, Joel E. Huber
  • Patent number: 4920216
    Abstract: 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: Grant
    Filed: May 28, 1987
    Date of Patent: April 24, 1990
    Assignee: The Trustees of Columbia in the City of New York
    Inventors: Ronald Breslow, Michael Brandl, Alan D. Adams, Jurgen Hunger
  • Patent number: 4913852
    Abstract: 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: Grant
    Filed: February 24, 1988
    Date of Patent: April 3, 1990
    Inventors: Catherine Milioni, Constantin Efthyimiopoulos, Bernard Koch, Louis Jung, Jean Jung