The Spiro Hetero Ring Contains -c(=x)-o-, Wherein X Is Chalcogen, As Part Of The Ring (e.g., Spiro-lactones, Etc.) Patents (Class 540/41)
  • Patent number: 8987239
    Abstract: The 15?,16?-methylene-17-hydroxy-19-nor-17-pregna-4-en-3-one-21-carboxylic acid ?-lactone derivatives of the present invention possess progestational efficacy. They have the general chemical formula I, in which Z is selected from the group comprising an oxygen atom, two hydrogen atoms, NOR and NNHSO2R, where R is hydrogen, C1-C10-alkyl, aryl or C7-C20-aralkyl, R4 is hydrogen or halogen, and moreover either: R6a, R6b together form methylene or 1,2-ethanediyl or R6a is hydrogen and R6b is selected from the group comprising hydrogen, C1-C10-alkyl, C2-C10-alkenyl or C2-C10-alkynyl, and R7 is selected from the group comprising hydrogen, C1-C10-alkyl, C3-C6-cycloalkyl, C2-C10-alkenyl or C2-C10-alkynyl, or: R6a is hydrogen and R6b and R7, together, denote a bond, an oxygen or form methylene, R18 represents hydrogen or C1-C3-alkyl and in addition include their solvates, hydrates, stereoisomers and salts.
    Type: Grant
    Filed: January 10, 2013
    Date of Patent: March 24, 2015
    Assignee: Bayer Intellectual Property GbmH
    Inventors: Ulrich Klar, Joachim Kuhnke, Rolf Bohlmann, Jan Hübner, Sven Ring, Thomas Frenzel, Frederik Menges, Steffen Borden, Hans-Peter Muhn, Katja Prelle
  • Patent number: 8937058
    Abstract: The invention relates to 17-hydroxy-19-nor-21-carboxylic acid-steroid ?-lactone derivatives with the chemical formula I, where R4, R6a, R6b, R7, R15, R16a, R16b, R18 and Z have the meanings stated in claim 1, and their solvates, hydrates, stereoisomers and salts. The invention further relates to the use of these derivatives for the production of a medicinal product for oral contraception and for the treatment of pre-, peri- and postmenopausal complaints and medicinal products that contain said derivatives. The derivatives according to the invention have a progestational and in preferred cases additionally an antimineralocorticoid and neutral to slightly androgenic action.
    Type: Grant
    Filed: December 23, 2008
    Date of Patent: January 20, 2015
    Inventors: Ulrich Klar, Joachim Kuhnke, Rolf Bohlmann, Jan Hübner, Sven Ring, Thomas Frenzel, Frederik Menges, Steffen Borden, Hans-Peter Muhn, Katja Prelle
  • Patent number: 8618084
    Abstract: Compositions and methods for inducing the deposition of elastin by administering compositions including a mineralocorticoid, such as, for example, aldosterone and, optionally, a secondary active agent for enhancing or modulating the effect of the mineralocorticoid are described herein.
    Type: Grant
    Filed: June 8, 2009
    Date of Patent: December 31, 2013
    Assignees: Human Matrix Sciences, LLC, The Hospital for Sick Children
    Inventors: Aleksander Hinek, Thomas F. Mitts
  • Patent number: 8524693
    Abstract: The invention relates to processes for obtaining steroids with a spirolactone group in position 17, particularly to industrially obtaining 6?,7?; 15?,16?-dimethylene-3-oxo-17?-pregn-4-ene-21,17-carbolactone, commonly known as Drospirenone, as well as to intermediates useful in said process.
    Type: Grant
    Filed: June 16, 2010
    Date of Patent: September 3, 2013
    Assignee: Crystal Pharma, S.A.
    Inventors: Jesús Miguel Iglesias Retuerto, Luis Gerardo Gutiérrez Fuentes, Antonio Lorente Bonde-Larsen
  • Patent number: 8470774
    Abstract: Compositions and methods for inducing the deposition of elastin in skin by administering compositions including a mineralocorticoid, such as, for example, aldosterone and, optionally, a secondary active agent for enhancing or modulating the effect of the mineralocorticoid are described herein.
    Type: Grant
    Filed: February 27, 2012
    Date of Patent: June 25, 2013
    Assignees: Human Matrix Sciences, LLC, The Hospital for Sick Children
    Inventors: Aleksander Hinek, Thomas F. Mitts
  • Patent number: 8445469
    Abstract: A 18-Methyl-19-nor-17-pregn-4-ene-21,17-carbolactone of general formula I in which Z, R4, R6, R7 are as defined below with the proviso that the compound is not 18-Methyl-15?,16?-methylene-3-oxo-19-nor-17-pregn-4-ene-21,17-carbolactone.
    Type: Grant
    Filed: December 30, 2005
    Date of Patent: May 21, 2013
    Assignee: Bayer Intellectual Property GmbH
    Inventors: Rolf Bohlmann, Dieter Bittler, Hermann Kuenzer, Peter Esperling, Hans-Peter Muhn, Karl-Heinrich Fritzemeier, Ulrike Fuhrmann, Katja Prelle, Steffen Borden
  • Patent number: 8148327
    Abstract: Compositions and methods for inducing the deposition of elastin in skin by administering compositions including a mineralocorticoid, such as, for example, aldosterone and, optionally, a secondary active agent for enhancing or modulating the effect of the mineralocorticoid are described herein.
    Type: Grant
    Filed: June 6, 2008
    Date of Patent: April 3, 2012
    Assignees: Human Matrix Sciences, LLC, The Hospital for Sick Children
    Inventors: Thomas Mitts, Aleksander Hinek
  • Publication number: 20110021472
    Abstract: The invention relates to 17-hydroxy-19-nor-21-carboxylic acid-steroid ?-lactone derivatives with the chemical formula I, where R4, R6a, R6b, R7, R15, R16a, R16b, R18 and Z have the meanings stated in claim 1, and their solvates, hydrates, stereoisomers and salts. The invention further relates to the use of these derivatives for the production of a medicinal product for oral contraception and for the treatment of pre-, peri- and postmenopausal complaints and medicinal products that contain said derivatives. The derivatives according to the invention have a progestational and in preferred cases additionally an antimineralocorticoid and neutral to slightly androgenic action.
    Type: Application
    Filed: December 23, 2008
    Publication date: January 27, 2011
    Inventors: Ulrich Klar, Jooachim Kuhnke, Rolf Bohlmann, Jan Huebner, Sven Ring, Thomas Frenzel, Frederik Menges, Steffen Borden, Hans Peter Muhn, Katja Prelle
  • Patent number: 7846917
    Abstract: The present invention describes the novel 18-methyl-19-norandrost-4-ene 17,17-spiro ethers of the general formula I in which Z is an oxygen atom, two hydrogen atoms, a group ?NOR or ?NNHSO2R, where R is a hydrogen atom or a straight- or branched-chain alkyl group having 1 to 4 or 3 to 4 carbon atoms, R4 is a hydrogen atom, a halogen atom or a trifluoromethyl group, and R6 and/or R7 may have ? or ? configuration, and R6 and R7 are independently of one another a hydrogen atom or a straight- or branched-chain alkyl group having 1 to 4 or 3 to 4 carbon atoms or a straight- or branched-chain alkenyl group having 2 to 4 or 3 to 4 carbon atoms or a saturated cycloalkyl group having 3 to 5 carbon atoms or together are a methylene group or a double bond. The novel compounds have progestational and antimineralocorticoid activity.
    Type: Grant
    Filed: June 28, 2007
    Date of Patent: December 7, 2010
    Assignee: Bayer Schering Pharma AG
    Inventors: Rolf Bohlmann, Joachim Kuhnke, Jan Huebner, Norbert Gallus, Frederik Menges, Steffen Borden, Hans-Peter Muhn, Katja Prelle
  • Publication number: 20100222571
    Abstract: A process for the preparation of Drospirenone (I) according to the scheme (A) wherein the substituent R is defined in the description. The process improves the product yield and purity by reducing the formation of undesired side-products and is particularly convenient for industrial-scale manufacturing.
    Type: Application
    Filed: July 21, 2008
    Publication date: September 2, 2010
    Applicant: NEWCHEM S.P.A.
    Inventors: Erika Andriolo, Mauro Montorsi, Stefano Rancan, Edoardo Mariani, Marco Bandini, Michele Contento, Achille Umani-Ronchi
  • Publication number: 20080234478
    Abstract: A process for the preparation and purification of Eplerenone is described wherein hydroxylated impurities are removed using a novel derivatization procedure.
    Type: Application
    Filed: March 26, 2007
    Publication date: September 25, 2008
    Inventors: Bhaskar Reddy Guntoori, Svetoslav S. Bratovanov, Mohamed Ibrahim Zaki, Elena Bejan, Stephen E. Horne
  • Patent number: 7417140
    Abstract: The present invention involves intermediates, including a 7?-substituted steroid (II), and processes which are used to prepare eplerenone, a useful pharmaceutical agent.
    Type: Grant
    Filed: December 21, 2006
    Date of Patent: August 26, 2008
    Assignee: Pfizer Inc.
    Inventors: Bruce Allen Pearlman, Amphlett Greg Padilla, Jeffrey L. Havens, Sonja S. MacKey, Haifeng Wu
  • Patent number: 7414127
    Abstract: The present invention involves intermediates, including a 7?-substituted steroid (II), and processes which are used to prepare eplerenone, a useful pharmaceutical agent.
    Type: Grant
    Filed: December 21, 2006
    Date of Patent: August 19, 2008
    Assignee: Pfizer Inc.
    Inventors: Bruce Allen Pearlman, Amphlett Greg Padilla, Jeffrey L. Havens, Sonja S. Mackey, Haifeng Wu
  • Patent number: 7411062
    Abstract: The present invention involves intermediates, including a 7?-substituted steroid (II), and processes which are used to prepare eplerenone, a useful pharmaceutical agent.
    Type: Grant
    Filed: December 21, 2006
    Date of Patent: August 12, 2008
    Assignee: Pfizer Inc.
    Inventors: Bruce Allen Pearlman, Amphlett Greg Padilla, Jeffrey L. Havens, Sonja S. Mackey, Haifeng Wu
  • Patent number: 7112670
    Abstract: The present invention involves a novel crystal form of 17?-hydroxy-7?-(5?-methyl-2?-furyl)-pregna-4,9(11)-dien-3-one-21-carboxylic acid, ?-lactone, having the formula which is an intermediate useful in preparation of an important pharmaceutical, eplerenone.
    Type: Grant
    Filed: September 19, 2003
    Date of Patent: September 26, 2006
    Assignee: Pharmacia Corporation
    Inventors: Bruce Allen Pearlman, Frederick J. Antosz
  • Patent number: 6953851
    Abstract: Multiple novel reaction schemes, novel process steps and novel intermediates are provided for the synthesis of epoxymexrenone and other compounds of Formula I wherein: —A—A—, —B—B—, R1, R3, R8 and R9 are as defined in the specification.
    Type: Grant
    Filed: September 26, 2003
    Date of Patent: October 11, 2005
    Assignee: G.D. Searle & Company
    Inventors: John S. Ng, Ping T. Wang, Julio A. Baez, Chin Liu, Dennis K. Anderson, Jon P. Lawson, Bernhard Erb, Joseph Wieczorek, Gennaro Mucciariello, Fortunato Vanzanella, Sastry A. Kunda, Leo J. Letendre, Mark J. Pozzo, Yuen-Lung L. Sing, Edward E. Yonan
  • Publication number: 20040220158
    Abstract: The present invention provides 5-androsten-3&bgr;-ol steroid intermediates and processes for their preparation.
    Type: Application
    Filed: June 1, 2004
    Publication date: November 4, 2004
    Inventors: Michael J. White, Peter Guillaume Marie Wuts, Doris Beck
  • Publication number: 20040127702
    Abstract: The present invention involves a novel crystal form of 17&bgr;-hydroxy-7&agr;-(5′-methyl-2′-furyl)-pregna-4,9(11)-dien-3-one-21-carboxylic acid, &ggr;-lactone, having the formula 1
    Type: Application
    Filed: September 19, 2003
    Publication date: July 1, 2004
    Inventors: Bruce Allen Pearlman, Frederick J. Antosz
  • Publication number: 20040097475
    Abstract: This invention relates to processes for the preparation of novel 7-carboxy substituted steroid compounds of Formula I, 1
    Type: Application
    Filed: March 21, 2003
    Publication date: May 20, 2004
    Inventor: Peter Guillaume Marie Wuts
  • Publication number: 20040087562
    Abstract: This invention relates to processes for the preparation of 7-carboxy substituted steroid compounds of Formula I, 1
    Type: Application
    Filed: March 21, 2003
    Publication date: May 6, 2004
    Inventor: Peter Guillaume Marie Wuts
  • Publication number: 20040034215
    Abstract: The present invention provides 5-androsten-3&bgr;-ol steroid intermediates and processes for their preparation.
    Type: Application
    Filed: March 21, 2003
    Publication date: February 19, 2004
    Inventors: Michael J. White, Peter Guillaume Marie Wuts, Doris Beck
  • Patent number: 6630587
    Abstract: Novel 9&agr;-hydroxy steroid compounds, including compounds of Formula IX wherein —A—A—, —B—B—, R1, R3, R8 and R9 are as defined in the specification.
    Type: Grant
    Filed: August 7, 2001
    Date of Patent: October 7, 2003
    Assignee: G. D. Searle & Company
    Inventors: John S. Ng, Ping T. Wang, Julio A. Baez, Chin Liu, Dennis K. Anderson, Jon P. Lawson, Bernhard Erb, Joseph Wieczorek, Gennaro Mucciariello, Fortunato Vanzanella, Sastry A. Kunda, Leo J. Letendre, Mark J. Pozzo, Yuen-Lung L. Sing, Edward E. Yonan
  • Patent number: 6610844
    Abstract: Multiple novel reaction schemes, novel process steps and novel intermediates are provided for the synthesis of epoxymexrenone and other compounds of Formula I wherein —A—A— represents the group —CHR4—CHR5— or —CR4═CR5—; R3, R4 and R5 are independently selected from the group consisting of hydrogen, halo, hydroxy, lower alkyl, lower alkoxy, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, cyano and aryloxy; R1 represents an alpha-oriented lower alkoxycarbonyl or hydroxyalkyl radical; —B—B— represents the group —CHR6—CHR7— or an alpha- or beta-oriented group: where R6 and R7 are independently selected from the group consisting of hydrogen, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy; and R8 and R9 are independently selected from the group consisting of hydrogen, hydroxy, halo, lower alkoxy, acyl, hydroxyalkyl
    Type: Grant
    Filed: March 29, 2002
    Date of Patent: August 26, 2003
    Assignee: G.D. Searle & Company
    Inventors: John S. Ng, Chin Liu, Dennis K. Anderson, Jon P. Lawson, Joseph Wieczorek, Sastry A. Kunda, Leo J. Letendre, Mark J. Pozzo, Yuen-Lung L. Sing, Ping T. Wang, Edward E. Yonan, Richard M. Weier, Thomas R. Kowar, Julio A. Baez, Bernhard Erb
  • Patent number: 6586591
    Abstract: A process for the formation of compounds of Formula VI: comprising hydrolyzing a compound corresponding to Formula VII: wherein —A—A—, —B—B—, R3, R8 and R9 are as defined in the specification.
    Type: Grant
    Filed: August 31, 2001
    Date of Patent: July 1, 2003
    Assignee: G.D. Searle & Co.
    Inventors: John S. Ng, Ping T. Wang, Julio A. Baez, Chin Liu, Dennis K. Anderson, Jon P. Lawson, Bernhard Erb, Joseph Wieczorek, Gennaro Mucciariello, Fortunato Vanzanella, Sastry A. Kunda, Leo J. Letendre, Mark J. Pozzo, Yuen-Lung L. Sing, Edward E. Yonan
  • Publication number: 20030100541
    Abstract: Multiple novel reaction schemes, novel process steps and novel intermediates are provided for the synthesis of epoxymexrenone and other compounds of Formula I 1
    Type: Application
    Filed: August 7, 2001
    Publication date: May 29, 2003
    Inventors: John S. Ng, Ping T. Wang, Julio A. Baez, Chin Liu, Dennis K. Anderson, Jon P. Lawson, Bernhard Erb, Joseph Wieczorek, Gennaro Mucciariello, Fortunato Vanzanella, Sastry A. Kunda, Leo J. Letendre, Mark J. Pozzo, Yuen-Lung L. Sing, Edward E. Yonan
  • Patent number: 6541463
    Abstract: Novel methods of medical treatment and/or inhibition of development of diseases are disclosed for diseases that are sensitive to androgenic or estrogenic activity. The treatments utilize inhibitors of type 5 and/or type 3 17&bgr;-hydroxysteroid dehydrogenase. Novel inhibitors of type 5 17&bgr;-hydroxysteroid dehydrogenase are also disclosed, as are novel inhibitors of type 3 17&bgr;-hydroxysteroid dehydrogenase.
    Type: Grant
    Filed: March 10, 1999
    Date of Patent: April 1, 2003
    Assignee: Endorecherche, Inc.
    Inventors: Fernand Labrie, Alain Belanger, Sylvain Gauthier, Van Luu-The, Yves Merand, Donald Poirier, Louis Provencher, Shankar M. Singh
  • Publication number: 20020045746
    Abstract: A novel crystalline form (Form L) of the aldosterone receptor antagonist drug eplerenone is provided having relatively high physical stability at normal temperatures of storage and use. Pharmaceutical compositions are also provided comprising Form L eplerenone, optionally accompanied by one or more other solid state forms of eplerenone, in a total unit dosage amount of eplerenone of about 10 to about 1000 mg, and further comprising one or more pharmaceutically acceptable excipients. Processes are provided for preparing Form L eplerenone and for preparing compositions comprising Form L eplerenone. A method for prophylaxis and/or treatment of an aldosterone-mediated condition or disorder is also provided, comprising administering to a subject a therapeutically effective amount of eplerenone, wherein at least a fraction of the eplerenone present is Form L eplerenone.
    Type: Application
    Filed: December 7, 2000
    Publication date: April 18, 2002
    Inventors: Kathleen P. Barton, Thomas B. Borchardt, Marlon V. Carlos, Subhash Desai, Leonard J. Ferro, Henry T. Gaud, Scott S. Ganser, Clay R. Little, Partha S. Mudipalli, Mark A. Pietz, Daniel R. Pilipauskas, Yuen-Lung L. Sing, Glenn L. Stahl, Joseph J. Wieczorek, Chris Y. Yan
  • Publication number: 20020042507
    Abstract: Multiple novel reaction schemes, novel process steps and novel intermediates are provided for the synthesis of epoxymexrenone and other compounds of Formula I 1
    Type: Application
    Filed: August 31, 2001
    Publication date: April 11, 2002
    Inventors: John S. Ng, Ping T. Wang, Julio A. Baez, Chin Liu, Dennis K. Anderson, Jon P. Lawson, Bernhard Erb, Joseph Wieczorek, Gennaro Mucciariello, Fortunato Vanzanella, Sastry A. Kunda, Leo J. Letendre, Mark J. Pozzo, Yuen-Lung L. Sing, Edward E. Yonan
  • Publication number: 20020038021
    Abstract: A novel crystalline form (Form H) of the aldosterone receptor antagonist drug eplerenone is provided having a relatively rapid dissolution rate in aqueous media. Also provided are novel solvated crystalline forms of eplerenone that, when desolvated, can yield Form H eplerenone. Also provided is amorphous eplerenone. Pharmaceutical compositions are provided comprising Form H eplerenone, optionally accompanied by one or more other solid state forms of eplerenone, in a total unit dosage amount of eplerenone of about 10 to about 1000 mg, and further comprising one or more pharmaceutically acceptable excipients. Processes are provided for preparing Form H eplerenone and for preparing compositions comprising Form H eplerenone. A method for prophylaxis and/or treatment of an aldosterone-mediated condition or disorder is also provided, comprising administering to a subject a therapeutically effective amount of eplerenone, wherein at least a fraction of the eplerenone present is Form H eplerenone.
    Type: Application
    Filed: December 7, 2000
    Publication date: March 28, 2002
    Inventors: Kathleen P. Barton, Thomas B. Borchardt, Marlon V. Carlos, Subhash Desai, Leonard J. Ferro, Henry T. Gaud, Scott S. Ganser, Clay R. Little, Partha S. Mudipalli, Mark A. Pietz, Daniel R. Pilipauskas, Yuen-Lung L. Sing, Glenn L. Stahl, Joseph J. Wieczorek, Chris Y. Yan
  • Publication number: 20020016455
    Abstract: Multiple novel reaction schemes, novel process steps and novel intermediates are provided for the synthesis of epoxymexrenone and other compounds of Formula I 1
    Type: Application
    Filed: April 3, 2001
    Publication date: February 7, 2002
    Inventors: John S. Ng, Ping T. Wang, Julio A. Baez, Chin Liu, Dennis K. Anderson, Jon P. Lawson, Bernhard Erb, Joseph Wieczorek, Gennaro Mucciariello, Fortunato Vanzanella, Sastry A. Kunda, Leo J. Letendre, Mark J. Pozzo, Yuen-Lung L. Sing, Edward E. Yonan
  • Patent number: 6331622
    Abstract: A process for the formation of an epoxy compound comprising contacting a substrate compound having an olefinic double bond with a peroxide compound in the presence of a peroxide activator, said peroxide activator corresponding to the formula: where Ro is a substituent having an electron withdrawing strength not less than that of monochloromethyl.
    Type: Grant
    Filed: February 8, 1999
    Date of Patent: December 18, 2001
    Assignee: G.D. Searle & Co.
    Inventors: John S. Ng, Ping T. Wang, Julio A. Baez, Chin Liu, Dennis K. Anderson, Jon P. Lawson, Bernhard Erb, Joseph Wieczorek, Gennaro Mucciariello, Fortunato Vanzanella, Sastry A. Kunda, Leo J. Letendre, Mark J. Pozzo, Yuen-Lung L. Sing, Edward E. Yonan
  • Patent number: 6180780
    Abstract: Multiple reaction schemes, process steps and intermediates are provided for the synthesis of epoxymexrenone, useful as a diuretic, and other compounds of Formula I wherein the variables are as defined by the specification.
    Type: Grant
    Filed: February 9, 1999
    Date of Patent: January 30, 2001
    Assignee: G.D. Searle & Co.
    Inventors: John S. Ng, Ping T. Wang, Julio A. Baez, Chin Liu, Dennis K. Anderson, Jon P. Lawson, Bernhard Erb, Joseph Wieczorek, Gennaro Mucciariello, Fortunato Vanzanella, Sastry A. Kunda, Leo J. Letendre, Mark J. Pozzo, Yuen-Lung L. Sing, Edward E. Yonan
  • Patent number: 6177416
    Abstract: 3-Oxyiminopregnane-21-carbolactones of formula I, wherein R is as defined by the specification, their production and use as pharmaceutical agents are described.
    Type: Grant
    Filed: October 5, 1999
    Date of Patent: January 23, 2001
    Assignee: Schering Aktiengesellschaft
    Inventors: Henry Laurent, Ralph Lipp, Peter Esperling, Johannes-Wilhelm Tack
  • Patent number: 5981744
    Abstract: Multiple reaction schemes, process steps and intermediates are provided for the synthesis of epoxymexrenone, useful as a diuretic, and other 9,11-epoxy-steroids.
    Type: Grant
    Filed: December 11, 1996
    Date of Patent: November 9, 1999
    Assignee: G. D. Searle and Co.
    Inventors: John S. Ng, Ping T. Wang, Julio A. Baez, Chin Liu, Dennis K. Anderson, Jon P. Lawson, Bernhard Erb, Joseph Wieczorek, Sastry A. Kunda, Leo J. Letendre, Mark J. Pozzo, Yuen-Lung L. Sing, Edward E. Yonan
  • Patent number: 5843933
    Abstract: Compounds of formula I ##STR1## wherein X, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meanings indicated in the description, are described, as well as processes for their production, pharmaceutical preparations containing these compounds as well as their use for treatment of diseases. The compounds have antigestagenic, antiglucocorticoid, antimineralocorticoid and antiandrogenic properties.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: December 1, 1998
    Assignee: Schering Aktiengesellschaft
    Inventors: Arwed Cleve, Cornelius Scheidges, Gunter Neef, Eckhard Ottow, Walter Elger, Sybille Beier
  • Patent number: 5426179
    Abstract: Steroid compounds active on the cardiovascular system of formula ##STR1## wherein X, n, R, R.sub.1 and R.sub.2 have the meanings mentioned in the description are described.
    Type: Grant
    Filed: February 12, 1992
    Date of Patent: June 20, 1995
    Assignee: Zambon Group S.p.A.
    Inventors: Giorgio Bertolini, Cesare Casagrande, Stefania Montanari, Gabriele Norcini, Francesco Santangelo
  • Patent number: 5426102
    Abstract: 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: Grant
    Filed: June 22, 1993
    Date of Patent: June 20, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: Wolfgang Schwede, Eckhard Ottow, Gunter Neef, Arwed Cleve, Krzysztof Chwalisz, Horst Michna
  • Patent number: 5273971
    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: July 3, 1989
    Date of Patent: December 28, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Stefan Scholz, Eckhard Ottow, Guenter Neef, Walter Elger, Sybille Beier, Krzysztof Chwalisz
  • Patent number: 5244886
    Abstract: New 11.beta.-phenyl-14.beta.H-steroids of general formula (I), where Z is an oxygen atom or the hydroxyimino-grouping N.about.OH, and M and N are either jointly a second compound or L is a hydrogen atom and M is an .alpha.-permanent hydroxy group and either A and B together are a second compound and D is a hydrogen atom, where R.sup.1 is a five or six-part heteroalkyl residue or a cycloalkyl, cycloalkenyl or aryl residue or A is a hydrogen atom and B and D together are a methylene bridge, where R.sup.1 besides the aforementioned residues may be a possibly substituted hydrocarbon residue with up to 10 C atoms, a possibly substituted amino group, a hydroxy or C.sub.1-8 alkoxy, mercapto or thioalkyl group, R.sup.2 is a methyl or ethyl residue, and R.sup.3 /R.sup.4 represents the usual combination of substituents on the C17 atom in steroid chemistry, having antigestagenic and other properties.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: September 14, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Stefan Scholz, Gunter Neef, Eckhard Ottow, Walter Elger, Sybille Beier, Krzysztof Chwalisz
  • Patent number: 5001119
    Abstract: Compounds of the formula: ##STR1## are useful as anti-cancer, anti-obesity, anti-diabetic, anti-coronary agents, anti-aging agents, anti-hypolipidemic agents and anti-autoimmune agents.
    Type: Grant
    Filed: November 25, 1987
    Date of Patent: March 19, 1991
    Inventors: Arthur G. Schwartz, Marvin L. Lewbart
  • Patent number: 4987128
    Abstract: 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: Grant
    Filed: February 24, 1987
    Date of Patent: January 22, 1991
    Assignee: Roussel Uclaf
    Inventors: Lucien Nedelec, Francois Nique, Anne-Marie Moura
  • Patent number: 4978657
    Abstract: Novel 19-nor-steroids of the formula ##STR1## wherein R.sub.1 is an organic group of 1 to 18 carbon atoms optionally containing at leat one heteroatom with the atom immediately adjacent the 11-carbon atom being carbon, R.sub.2 is a hydrocarbon of 1 to 8 carbon atoms, X is the remainder of a pentagonal or hexagonal ring optionally substituted and optionally containing one unsaturated bond, the A and B rings are selected from the group consisting of ##STR2## R' and R" are individually selected from the group consisting of hydrogen, --CN and alkyl of 1 to 4 carbon atoms, R.sub.x is selected from the group consisting of hydrogen and OR.sub.e, R.sub.e is selected from the group consisting of hydrogen, optionally substituted alkyl of 1 to 6 carbon atoms and acyl, R.sub.a may be in the E or Z positions as indicated by the wavy line and is selected from the group consisting of ##STR3## and acyloxy, R.sub.a ' and R.sub.
    Type: Grant
    Filed: December 17, 1985
    Date of Patent: December 18, 1990
    Assignee: Roussel Uclaf
    Inventors: Jean-Georges Teutsch, Vesperto Torelli, Roger Deraedt, Daniel Philibert, Germain Costerousse
  • Patent number: 4912097
    Abstract: Novel 11.beta.-alkynylphenyl-19-nor-steroids of the formula ##STR1## wherein R.sub.1 is alkynyl of 2 to 8 carbon atoms optionally substituted with at least one member of the group consisting of --OH halogen, trialkylsilyl of 1 to 6 alkyl carbon atoms, alkoxy and alkylthio of 1 to 6 carbon atoms and dialkylamino of 1 to 6 alkyl carbon atoms having remarkably antiprogestomimetic and antiglucocorticoidal activity.
    Type: Grant
    Filed: April 30, 1987
    Date of Patent: March 27, 1990
    Assignee: Roussel Uclaf
    Inventors: Jean-Georges Teutsch, Michel Klich, Daniel Philibert
  • Patent number: 4904462
    Abstract: Novel, multiple-tritiated steroid-20,17-spirolactones of general Formula I ##STR1## wherein --A--B-- is --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH-- or ##STR2## and --C--D-- is ##STR3## R is hydrogen or tritium and n is 0 or 1,are usable as tracer materials for the detection of mineralocorticoid receptors.
    Type: Grant
    Filed: April 12, 1985
    Date of Patent: February 27, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Paul-Eberhard Schulze, Klaus Nickisch, Henry Laurent, Kunhard Pollow
  • Patent number: 4891365
    Abstract: 17-Substituted estradienes and estratrienes of Formula I ##STR1## wherein ##STR2## R is alkyl, alkenyl or cycloalkyl of up to 5 carbon atoms if ##STR3## R is hydrogen, alkyl, alkenyl or cycloalkyl of up to 5 carbon atoms if ##STR4## is a CC-single or CC-double bond, exhibit, an aldosterone-antagonistic activity and a strong gestagen potency.
    Type: Grant
    Filed: July 2, 1987
    Date of Patent: January 2, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Rudolf Wiechert, Sybille Beier, Walter Elger, Klaus Annen, Klaus Nickisch, Henry Laurent
  • Patent number: 4808710
    Abstract: A novel class of steroids having pregnancy-terminating and/or pregnancy-preventing activity and a very low antiglucocorticoid activity have been found. The compounds have the general formula: ##STR1## wherein R.sub.1 and R.sub.2 each separately represent H or a (1-4 C) hydrocarbon radical or together represent a (2-6 C) hydrocarbon radical, R.sub.3 represents H or a (1-4 C) hydrocarbon radical, optionally having an OH substituent, R.sub.4 represents OH or an ester or ether group, or together with R.sub.3 represents O or a heterocyclic ring system containing O, and wherein the broken line indicates an optionally present double bond between the carbon atoms at positions 9 and 10 of the steroid skeleton.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: February 28, 1989
    Assignee: Akzo N.V.
    Inventors: Hendrik P. de Jongh, Martinus J. van den Heuvel
  • Patent number: 4614616
    Abstract: A process for preparing a 3.beta.,7.beta.-dihydroxy-.DELTA..sup.5 -steroid of the formula ##STR1## wherein Q is ##STR2## and R.sub.1 is hydrogen, trimethylacetyl, tert-butyldimethylsilyl, dimethyl-2-(3-methylbutyl)silyl or tribenzylsilyl, comprises fermenting a 3.beta.-hydroxy-.DELTA..sup.5 -steroid of the formula ##STR3## wherein Q is as defined above, andR.sub.2 is hydrogen or alkanoyl of 2-6 carbon atoms, with a culture of Botryodiplodia malorum to obtain the corresponding 3.beta.,7.beta.-dihydroxy-.DELTA..sup.5 -steroid; and, optionally, reacting the resultant product with trimethylacetic anhydride, tert-butyldimethylsilyl chloride, dimethyl-2-(3-methylbutyl)silyl chloride, or tribenzylsilyl chloride.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: September 30, 1986
    Assignee: Schering Aktiengesellschaft
    Inventors: Karl Petzoldt, Rudolf Wiechert, Henry Laurent, Klaus Nickisch, Dieter Bittler