Oxygen Bonded Directly At The 16- Or 17-position Of The Cyclopentanohydrophenanthrene Ring System Patents (Class 552/650)
  • Patent number: 9357938
    Abstract: A method of calibrating a motor imagery detection module and a system for motor rehabilitation are provided. The method comprises acquiring Electroencephalography (EEG) data from a subject; selecting classification features from the EEG data; wherein the feature selection comprises modelling an idle state ?n of the subject by M sub-classes ?j, j=1, . . . , M.
    Type: Grant
    Filed: March 31, 2011
    Date of Patent: June 7, 2016
    Assignees: Agency for Science, Technology and Research, Tan Tock Seng Hospital Pte Ltd
    Inventors: Kai Keng Ang, Cuntai Guan, Sui Geok Karen Chua, Chuanchu Wang, Hock Guan Adrian Tan, Kok Soon Phua, Haihong Zhang, Zheng Yang Chin
  • Publication number: 20140315833
    Abstract: A cocrystalline DHEA composition with at least one additional coformer is disclosed for therapeutic formulations. The cocrystalline DHEA/coformer formulation including at least one coformer chosen from the group consisting of glutaric acid, maleic acid, tartaric acid, fructose, and wherein the L-isomer of tartaric acid and the D-isomer of fructose are utilized. The cocrystalline DHEA/coformer formulations include certain excipients as a solubilizer or inhibitor.
    Type: Application
    Filed: April 21, 2014
    Publication date: October 23, 2014
    Inventors: Anders Berkenstam, Edward Kuczynski, Alf S. Andersson, Jan-Ake Gustafsson, Carly Sue Filgueira
  • 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: 8586770
    Abstract: The invention relates to methods to manipulate stem cells in vivo and in vitro to treat, e.g., a condition where cell or tissue repair is needed.
    Type: Grant
    Filed: February 18, 2011
    Date of Patent: November 19, 2013
    Assignee: Harbor Therapeutics, Inc.
    Inventor: James M. Frincke
  • 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
  • Patent number: 8288367
    Abstract: Substituted estratriene compounds of formula (I) useful in therapy, especially in the treatment or inhibition of a steroid hormone dependent disorder requiring the inhibition of a 17?-hydroxysteroid dehydrogenase (17?-HSD) type 1, type 2 and/or type 3 enzyme, as well as their salts, pharmaceutical compositions containing such compounds and processes for preparing such compounds.
    Type: Grant
    Filed: November 29, 2007
    Date of Patent: October 16, 2012
    Assignee: Solvay Pharmaceuticals GmBH
    Inventors: Josef Messinger, Uwe Schoen, Heinrich-Hubert Thole, Bettina Husen, Pasi Koskimies, Mikko Unkila
  • Publication number: 20120214987
    Abstract: The invention relates to processes for preparing 3?-O-linked steroids including 3?-O-linked-androst-5-ene steroids and 3?-O-linked-5a-androstane steroids. In one process a 3?,4?-epoxy androst-5-en-17-one is predominately reduced at the epoxy moiety wherein reduction of the 3?,4? epoxy functional group occurs preferentially at position C4 with retention of configuration at position C3 to provide a 3?-O-linked-androst-5-ene steroid. In another process, conditions are provided for inversion of configuration of a 3?-hydroxy-androst-5-ene steroid by the Mitsunobu reaction to provide a 3?-O-linked-androst-5-ene steroid with reduced amounts of 3?,5?-cycloandrostane side-product impurities.
    Type: Application
    Filed: December 15, 2011
    Publication date: August 23, 2012
    Inventors: Yu Ge, Steven K. White, Yujin Huang
  • Patent number: 8124598
    Abstract: The present invention comprises novel methods for the use of compositions comprising 7-keto DHEA for treating psychiatric conditions. These methods include administering an effective amount of a composition comprising 7-keto DHEA in an acceptable carrier, alone or in combination with other psychiatric drugs, such as analgesic agents, anticonvulsants, anti-anxiety agents, antidepressants, anti-panic agents, antipsychotic agents, bipolar agents, psychostimulants to reduce or ameliorate symptoms of a psychiatric condition. This method may be used alone or as an adjunctive treatment for treating a wide variety of psychiatric conditions such as stress disorders, anxiety disorders and depressive disorders.
    Type: Grant
    Filed: September 7, 2007
    Date of Patent: February 28, 2012
    Inventors: Sharon Sageman, Richard P. Brown
  • Publication number: 20100331268
    Abstract: Described herein are nitrated lipids and methods of making and using the nitrated lipids.
    Type: Application
    Filed: June 9, 2010
    Publication date: December 30, 2010
    Applicants: THE UAB RESEARCH FOUNDATION, State of Oregon Acting By and Through the Board of Education on behalf of the University of Oregon
    Inventors: Bruce A. Freeman, Francisco Schopfer, Valerie O'Donnell, Paul Baker, Yuqing E. Chen, Bruce Branchaud
  • Publication number: 20100317639
    Abstract: A monoester of a family of steroids with a C16-C24 fatty acid for use as a medicament is disclosed. Particularly the monoester of 5?-androstan-3?,17?-diol with a C16-C24 fatty acid is disclosed, such as preferably linoleic acid in all its isomeric forms. The medicament is capable to reduce the accumulation of cholesterol esters, reducing the ACAT enzyme (acyl-coenzyme A: cholesterol acetyltransferase) effect so that monoesters are used for the manufacture of a medicament for treating adrenoleucodistrophy, Alzheimer's disease and arteriosclerosis.
    Type: Application
    Filed: December 12, 2006
    Publication date: December 16, 2010
    Inventor: Anna Petroni
  • Publication number: 20100099141
    Abstract: The present invention relates to a method for preparing 2-alkoxy and 2-aryloxyestrogen compounds, and the intermediate compounds prepared during the use of this method, which intermediate compounds are useful intermediates in the preparation of certain physiologically active compounds.
    Type: Application
    Filed: October 16, 2008
    Publication date: April 22, 2010
    Inventors: Paolo Lombardi, Franco Buzzetti
  • Patent number: 7667056
    Abstract: The present invention relates to a new process of synthesis and to some new intermediates for the preparation of steroids with progestogen activity, more particularly, for the preparation of Desogestrel of formula (I). Said process is characterized by the regioselective reduction of the compound of formula (II) to give the intermediate of formula (III).
    Type: Grant
    Filed: July 31, 2003
    Date of Patent: February 23, 2010
    Assignee: Poli Industria Chimica S.p.A.
    Inventors: Paride Grisenti, Fabio Pecora, Elisa Verza, Massimo Leoni, Laura Bossi
  • Publication number: 20090291929
    Abstract: The invention provides for compounds having formula (1) wherein; R1 is O, (H,H), (H,OH), or NOR, with R being hydrogen, (C1-6) alkyl or (C1-6) acyl; R2 is hydrogen, methyl, ethyl, or ethenyl; R3 is hydrogen, methyl, ethyl, ethenyl, fluoro, or chloro; R4 is methyl, or ethyl; R5 is hydrogen, methyl, or ethyl; R6 is hydrogen, methyl, ethyl, (C1-3) alkenyl, or (C1-3) alkynyl; R7 is hydrogen or (C1-15) acyl; and at least one of R5 or R6 is hydrogen; or a pharmaceutically acceptable salt thereof, for use as medicine for a treatment to increase androgen levels, for androgen supplementation, for testosterone replacement and for benign prostate hypertrophy and in a method of male contraception, preferably as sole means to achieve both progestagenic sterilitant effect and androgen supplementation.
    Type: Application
    Filed: June 16, 2006
    Publication date: November 26, 2009
    Applicant: N.V. ORGANON
    Inventors: Jaap Van Der Louw, Dirk Leysen, Marcel Evert De Gooijer, Joseph Maria Gerardus Barbara Cals
  • Publication number: 20090176752
    Abstract: The instant invention provides potent antiandrogen compounds, such as 3?-acetoxyandrost-1,5-diene-17-ethylene ketal and 3?-hydroxyandrost-1,5-diene-17-ethylene ketal, and methods for their use in the prevention and treatment of biological conditions mediated by androgen receptors. Thus, for example, compounds of the invention are useful in the prevention and treatment of prostrate cancer. Furthermore, it has been discovered that compounds of the invention are useful in the prevention and treatment of androgen-independent cancers such as androgen-independent prostrate cancer. Finally, inventive compounds may be used to treat antiandrogen induced withdrawal syndrome.
    Type: Application
    Filed: March 17, 2009
    Publication date: July 9, 2009
    Applicant: Hollis-Eden Pharmaceuticals, Inc.
    Inventors: Henry A. Lardy, Ashok Marwah, Padma Marwah
  • Publication number: 20090082323
    Abstract: The present application describes deuterium-enriched fulvestrant, pharmaceutically acceptable salt forms thereof, and methods of treating using the same.
    Type: Application
    Filed: August 22, 2008
    Publication date: March 26, 2009
    Applicant: Protia, LLC
    Inventor: Anthony W. Czarnik
  • Publication number: 20080200440
    Abstract: The present invention relates to progesterone receptor antagonists of general formula I: in which R1 can be a hydrogen atom and R2 a hydroxyl group or R1 and R2 together can be an oxo group.
    Type: Application
    Filed: November 15, 2007
    Publication date: August 21, 2008
    Inventors: Ulrike Fuhrmann, Anja Schmidt, Arwed Cleve, Orlin Petrov, Gunnar Garke, Stefan Pruehs, Margarete Brudny-Kloeppel, Antje Rottmann, Rainer Hasselmann, Marcus Schultze-Mosgau, Carsten Moeller
  • Publication number: 20080176824
    Abstract: The invention provides compositions comprising formula 1 steroids, e.g., 16?-bromo-3?-hydroxy-5?-androstan-17-one hemihydrate and one or more excipients, typically wherein the composition comprises less than about 3% water. The compositions are useful to make improved pharmaceutical formulations. The invention also provides methods of intermittent dosing of steroid compounds such as analogs of 16?-bromo-3?-hydroxy-5?-androstan-17-one and compositions useful in such dosing regimens. The invention further provides compositions and methods to inhibit pathogen (viral) replication, ameliorate symptoms associated with immune dysregulation and to modulate immune responses in a subject using certain steroids and steroid analogs. The invention also provides methods to make and use these immunomodulatory compositions and formulations.
    Type: Application
    Filed: October 23, 2006
    Publication date: July 24, 2008
    Inventors: James M. Frincke, Christopher L. Reading, Clarence N. Ahlem
  • Patent number: 6881728
    Abstract: Androgenic steroids having a (14?,17?-)-17-(hydroxymetheyl) configuration, useful for the preparation of male contraceptives and pharmaceutical formulations for the treatment of androgen insufficiency.
    Type: Grant
    Filed: March 2, 2000
    Date of Patent: April 19, 2005
    Assignee: Akzo Nobel N.V.
    Inventors: Hubert Jan Jozef Loozen, Dirk D. Leysen, Jaap van der Louw
  • Patent number: 6596885
    Abstract: Novel compounds having a formula selected from the group consisting of wherein the substituents are defined as in the specification which are intermediates for the production of vinyl compounds having a remarkable anti-estrogenic and anti-proliferative activity.
    Type: Grant
    Filed: June 26, 2001
    Date of Patent: July 22, 2003
    Assignee: Aventis Pharma S.A.
    Inventors: Andre Claussner, Francois Nique, Jean-Georges Teutsch, Patrick Van de Velde
  • Patent number: 6498153
    Abstract: An extended release composition comprising a first composition comprising growth promoters and a second composition comprising growth promoters and a biodegradable polymer is described. A method of increasing weight gain in food animals utilizing the composition, a pharmaceutical dosage form containing the composition and a method of preparing the pharmaceutical dosage form are also described, as are pellets of the composition for implantation in food animals.
    Type: Grant
    Filed: March 22, 1999
    Date of Patent: December 24, 2002
    Assignees: Akzo Nobel N.V., Southern BioSystems
    Inventors: Susan Mancini Cady, Claude Macar, John W. Gibson
  • Patent number: 6369047
    Abstract: An androgenic steroid compound of the formula: wherein: X Y, Z, R1, R2, R3, R5 and R6 are as defined herein.
    Type: Grant
    Filed: June 9, 1999
    Date of Patent: April 9, 2002
    Assignee: Research Triangle Institute
    Inventors: C. Edgar Cook, John A. Kepler, Yue-Wei Lee, Mansukh C. Wani
  • Publication number: 20020002156
    Abstract: An androgenic steroid compound of the formula: 1
    Type: Application
    Filed: June 9, 1999
    Publication date: January 3, 2002
    Inventors: C. EDGAR COOK, JOHN A. KEPLER, YUE-WEI LEE, MANSUKH C. WANI
  • Patent number: 6090957
    Abstract: The present invention provides new process of preparing neuromuscular blocking agents. The process include preparing neuromuscular blocking agents using the compounds of formula I: ##STR1## wherein R.sub.1 is=O and X is halo; and formula II: ##STR2## wherein R, and X are as defined above.
    Type: Grant
    Filed: October 1, 1998
    Date of Patent: July 18, 2000
    Assignee: Poli Industria Chimica S.p.A.
    Inventors: Ambrogio Magni, Paride Grisenti
  • Patent number: 6080735
    Abstract: This invention is relating to new estra-1,3,5(10)-trien-sulfamates carrying at the 3-position an R--SO.sub.2 --O--group, with R being an R.sup.1 R.sup.2 N--group in which R.sup.1 and R.sup.2, independently of each other, represent a hydrogen atom, an alkyl residue with 1-5 C atoms or, together with the N atom, a polymethylene-imino residue with 4-6 C atoms or a morpholino residue.The compounds, according to this invention, are suitable for hormonal contraception and climacteric hormone replacement therapy (HRT) as well as for treatment of gynecological and andrological diseases. Hence, only low hepatic estrogenicity is exhibited by the compounds according to this invention.Also described are processes for preparation of the compounds according to this invention and for preparation of pharmaceutical compositions.
    Type: Grant
    Filed: February 2, 1998
    Date of Patent: June 27, 2000
    Assignee: Jenapharm GmbH & Co. KG
    Inventors: Sigfrid Schwarz, Walter Elger, Hans-Joachim Siemann, deceased, by Margit Lucas, heir, by Frank Siemann, heir, Gudrun Reddersen, Birgitt Schneider
  • Patent number: 6046186
    Abstract: Novel compounds useful as inhibitors of estrone sulfatase are provided. The compounds have the structural formula (I) wherein r1 is an optional double bond, R.sup.1 and R.sup.2 are selected from the group consisting of hydrogen and lower alky, or together form a cyclic substituent (II) ##STR1## wherein Q is NH, O or CH.sub.2, and the other various substituents are as defined herein. Pharmaceutical compositions and methods for using the compounds of formula (I) to treat estrogen-dependent disorders are provided as well.
    Type: Grant
    Filed: December 24, 1997
    Date of Patent: April 4, 2000
    Assignee: SRI International
    Inventors: Masato Tanabe, Richard H. Peters, Wan-Ru Chao, Kazuhiko Shigeno
  • Patent number: 5986115
    Abstract: This invention describes new, substituted 7.alpha.-(.xi.-aminoalkyl)-estratrienes of general formula I ##STR1## in which side chain SK is a radical of partial formula ##STR2## as well as their physiologically compatible addition salts with organic and inorganic acids.The new compounds represent compounds with very strong antiestrogenic action.The compounds according to the invention are, on the one hand, pure antiestrogens, or, on the other hand, antiestrogens with estrogenic partial action. Based on this spectrum of action, the new compounds are highly suitable for the production of pharmaceutical agents for tumor therapy and hormone replacement treatment.
    Type: Grant
    Filed: January 28, 1999
    Date of Patent: November 16, 1999
    Assignee: Schering AG
    Inventors: Rolf Bohlmann, Dieter Bittler, Josef Heindl, Nikolaus Heinrich, Helmut Hofmeister, Hermann Kunzer, Gerhard Sauer, Christa Hegele-Hartung, Rosemarie Lichtner, Yukishige Nishino, Karsten Parczyk, Martin Schneider
  • Patent number: 5892069
    Abstract: The application discloses methods of treating mammalian diseases characterized by abnormal cell mitosis by administering estradiol derivatives including those comprising colchicine or combretastatin A-4 structural motifs of the general formulae found below in a dosage sufficient to inhibit cell mitosis. The application discloses novel compounds used in the methods.
    Type: Grant
    Filed: April 25, 1997
    Date of Patent: April 6, 1999
    Assignee: The Children's Medical Center Corporation
    Inventors: Robert John D'Amato, Moses Judah Folkman
  • 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: 5804576
    Abstract: Steroids of the formula: ##STR1## useful as cancer preventive agents, anti-obesity agents, anti-hyperglycemic agents, anti-aging agents, and anti-hypercholesterolemic agents and anti-auto-immune agents.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: September 8, 1998
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Arthur G. Schwartz, John R. Williams, Magid Abou-Gharbia, Ann R. Swern, Marvin Louis Lewbart
  • Patent number: 5723455
    Abstract: Novel antiandrogenic agents are provided. An exemplary group of compounds has the structural formula (I) ##STR1## wherein R.sup.1 through R.sup.10, a and b are as defined herein. Pharmaceutical compositions and methods for using the compounds of formula (I) to treat androgen-related clinical conditions are provided, as are methods and compositions for using the compounds as contraceptive agents.
    Type: Grant
    Filed: March 11, 1997
    Date of Patent: March 3, 1998
    Assignee: SRI International
    Inventors: Masato Tanabe, Wan-Ru Chao, Wesley K. M. Chong, David F. Crowe
  • Patent number: 5714481
    Abstract: Steroids of the formula: ##STR1## useful as cancer preventive agents, anti-obesity agents, anti-hyperglycemic agents, anti-aging agents, and anti-hypercholesterolemic agents and anti-auto-immune agents.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: February 3, 1998
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Arthur G. Schwartz, John R. Williams, Magid Abou-Gharbia, Daniel Swern, deceased, Marvin Louis Lewbart
  • Patent number: 5700793
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 23, 1997
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Arthur G. Schwartz, Marvin Louis Lewbart
  • Patent number: 5597701
    Abstract: A process and appropriate device are disclosed for determining the androstenone content of adipose tissues in clearly shorter times. The disclosed process has the following steps: (a) liquefying an adipose tissue sample by heating up to a predetermined temperature in the 45.degree. to 60.degree. C.
    Type: Grant
    Filed: March 7, 1995
    Date of Patent: January 28, 1997
    Assignee: Riedel-De Haen Aktiengesellschaft
    Inventors: Rolf P. Claus, Martin Dehnhard
  • 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: 5272140
    Abstract: The invention relates to 11-aryl steroid derivatives, having the structure ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as described in the specificationand to processes for their preparation and to pharmaceuticals comprising these compounds.These compounds exhibit a strong anti-progestinic activity and a weak or non-existent anti-glucocorticoid activity.
    Type: Grant
    Filed: February 27, 1990
    Date of Patent: December 21, 1993
    Assignee: Akzo N.V.
    Inventor: Hubert J. J. Loozen
  • Patent number: 5252565
    Abstract: The present invention is directed to a group of compounds which are haloethyl substituted steroidal enzyme inhibitors. These compounds are useful as aromatase, 19-hydroxylase, and aldosterone biosynthesis inhibitors and they are prepared from the corresponding epoxide.
    Type: Grant
    Filed: September 6, 1991
    Date of Patent: October 12, 1993
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Norton P. Peet, Joseph P. Burkhart, J. O'Neal Johnston
  • Patent number: 5208263
    Abstract: Disclosed are novel classes of anti-androgen including dihydrophenanthrene derivatives, their method of synthesis and their use in treating disorders associated with excessive androgenic activities.
    Type: Grant
    Filed: September 27, 1989
    Date of Patent: May 4, 1993
    Assignee: Arch Development Corporation
    Inventors: Shutsung Liao, John Pataki, Ronald G. Harvey
  • Patent number: 5182381
    Abstract: Novel 3-keto-19-nor-.DELTA..sup.4,9 -steroids of the formula ##STR1## and their non-toxic, pharmaceutically acceptable acid addition salts possessing a remarkable antiglucocorticoidal activity.
    Type: Grant
    Filed: September 10, 1991
    Date of Patent: January 26, 1993
    Assignee: Roussel Ulcaf
    Inventors: Daniel Philibert, Jean G. Teutsch, Germain Costerousse, Roger Deraedt
  • Patent number: 5157031
    Type: Grant
    Filed: March 21, 1989
    Date of Patent: October 20, 1992
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Arthur G. Schwartz, Marvin L. Lewbart
  • Patent number: 5140106
    Abstract: A process for the production of 3-deoxy-4-ene steroids of the general formula I ##STR1## is described, in which R.sub.1, R.sub.2 and R.sub.3 mean a hydrogen atom or a methyl group,R.sub.4 represents a lower alkyl group, a phenyl group or a free, esterified or etherified hydroxy group,R.sub.5 symbolizes a hydrogen atom, a vinyl group or the grouping --C.tbd.CR.sub.6 with R.sub.6 meaning a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms or a halogen atom,X represents a methylene group, a fluoromethylene group, an ethylidene group or a vinylidene group,Y and U represent a methylene group or an ethylidene group andZ symbolizes a methylene group, an ethylidene group, a vinylidene group, a chloromethylene group or a hydroxymethylene group and in which the bonds represent three single bonds or one double bond and two single bonds or a conjugated double bond.
    Type: Grant
    Filed: January 17, 1991
    Date of Patent: August 18, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Ekkehard Winterfeldt, Ulf Tilstamm, Helmut Hofmeister, Henry Laurent
  • Patent number: 5116830
    Abstract: This invention relates to a stereoisomerically pure .DELTA..sup.2 compound of the formula (I): ##STR1## wherein: R.sup.1 is hydrogen or --(C.dbd.O)--R.sup.2, wherein:R.sup.2 is an organic substituent selected from the group consisting of alkyls, alkenyls, alkynyls, cycloalkyls, cycloalkylalkylenes, haloalkyls, aryls, haloaryls and arylalkylenes, and their product by the process of:(a) reacting the 17.beta.-hydroxy group of 17.beta.-hydroxy-5.alpha.-estr-1-en-3-one with dihydropyran to produce the 3-keto-17.beta.-ether;(b) reducing the 3-keto-17.beta.-ether product of step (a) with lithium in ammonia;(c) reacting the product of step (b) with dialkyl chlorophosphate to produce the 3-substituted phosphate;(d) reducing the product of step (c) with lithium and ammonia to produce the .DELTA..sup.2 -protected-17.beta.-ether product;(e) hydrolysis of the produce of step (d) to product the .DELTA..sup.2 -17.beta.-hydroxy compound;(f) oxidizing the 17.beta.
    Type: Grant
    Filed: June 2, 1986
    Date of Patent: May 26, 1992
    Assignee: SRI International
    Inventors: Masato Tanabe, David F. Crowe, Richard H. Peters, John G. Johansson
  • Patent number: 5086047
    Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl, alkylthio and haloalkyl of 1 to 6 carbon atoms, alkenyl and alkynyl of 2 to 6 carbon atoms, optionally substituted arylthio of 6 to 10 carbon atoms, aryl of 6 to 12 carbon atoms, acyl of an organic carboxylic acid of 1 to 12 carbon atoms, --CN, cycloalkyl of 3 to 6 carbon atoms and --(CH.sub.2).sub.m --Re, m is an integer from 1 to 3, Re is --OH or --SH or --Salk, Alk is alkyl of 1 to 6 carbon atoms, X is selected from the group consisting of oxygen, N--O--R.sub.1, ##STR2## or =X is H.sub.2 or ##STR3## R.sub.A and R.sub.B are individually selected from the group consisting of hydrogen, halogen and alkyl of 1 to 6 carbon atoms, R.sub.1 is hydrogen or alkyl of 1 to 6 carbon, R' is hydrogen or acyl, the wavy lines indicate --or -position, Y is selected from the group consisting of oxygen, NOR, ##STR4## or =Y is ##STR5## H.sub.
    Type: Grant
    Filed: December 24, 1990
    Date of Patent: February 4, 1992
    Assignee: Roussel Uclaf, Department des Brevets
    Inventors: Jean-Francois Gourvest, Dominique Lesuisse
  • Patent number: 5064822
    Abstract: Novel 3-keto-19-nor-.DELTA..sup.4,9 -steroids of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of naphthyl, phenylphenyl, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms optionally containing additional unsaturations, phenoxy, furyl, cycloalkyl of 3 to 6 carbon atoms, thienyl optionally substituted with at least one member of the group consisting of halogen and alkyl and haloalkyl of 1 to 6 carbon atoms and phenyl optionally substituted with at least one member of the group consisting of --OH, halogen, --CF.sub.3, alkyl and alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, phenoxy and alkylthio of 1 to 6 carbon atoms optionally oxidized to the sulfoxide or sulfone, R.sub.2 is selected from the group consisting of methyl and ethyl, R.sub.
    Type: Grant
    Filed: November 16, 1989
    Date of Patent: November 12, 1991
    Assignee: Roussel Uclaf
    Inventors: Daniel Philibert, Jean G. Teutsch, Germain Costerousse, Roger Deraedt
  • Patent number: 5026693
    Abstract: Novel esters of 9.alpha.-fluoro- and chloro-corticosteroids of the formula ##STR1## wherein Y is chlorine or OR.sub.1, R.sub.1 and R.sub.2 represent an acyl group of 2-6 carbon atoms or a benzoyl group and where R.sub.1 and R.sub.2 can be the same or different in the same molecule, R.sub.3 is methyl or fluorine in either the .alpha.- or .beta.- orientation, X is chlorine or fluorine, and the C.sub.1 C.sub.2 bond can be saturated or not, especially those compounds of the formula ##STR2## wherein Y and R.sub.2 have the significance given above, are prepared by reacting the respective 9.beta.,11.beta.-epoxy compounds with hydrogen fluoride or chloride.
    Type: Grant
    Filed: May 21, 1990
    Date of Patent: June 25, 1991
    Assignee: Hovione Inter Ltd.
    Inventors: Ivan Villax, William Heggie, Philip R. Page
  • 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: 4945064
    Abstract: Estrane and androstane derivatives of formula I ##STR1## wherein X is bromine, iodine, triphenyltin or trialkyltin of 1 to 6 carbon atoms per alkyl radical,Y represents two hydrogen atoms or methylene,Z represents two hydrogen atoms, oxo or alkylenedioxy of 2 to 6 carbon atoms andV is ethylene, vinylene, 1,3-propylene or cyclopropylene,R.sub.1 is hydrogen or a hydrocarbon radical of up to 8 hydrocarbon atoms, optionally interrupted by an oxa group or substituted by an oxo group,R.sub.2 is methyl or ethyl,R.sub.3 and R.sub.4 represent a carbon-carbon bond or R.sub.3 is hydrogen and R.sub.4 is hydrogen or methyl,.DELTA.symbolizes a 4(5)-double bond if Z signifies two hydrogen atoms or an oxo group; or a 5(6)-double bond or, for the estrane derivatives of formula I, also a 5(10)-double bond, if Z is alkylenedioxy,are pharmacologically effective substances or intermediates for preparation thereof.
    Type: Grant
    Filed: January 19, 1988
    Date of Patent: July 31, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Hofmeister, Henry Laurent, Paul E. Schulze, Klaus Annen, Rudolf Wiechert, Kunhard Pollow, Bernhard Manz, Hans-Joerg Grill
  • Patent number: RE39592
    Abstract: An extended release composition comprising a first composition comprising growth promoters and a second composition comprising growth promoters and a biodegradable polymer is described. A method of increasing weight gain in food animals utilizing the composition, a pharmaceutical dosage form containing the composition and a method of preparing the pharmaceutical dosage form are also described, as are pellets of the composition for implantation in food animals.
    Type: Grant
    Filed: December 22, 2004
    Date of Patent: April 24, 2007
    Assignee: Intervet Inc.
    Inventors: Susan Mancini Cady, Claude Macar, John W. Gibson