Nitrogen Bonded Directly To The Cyclopentanohydrophenanthrene Ring System Patents (Class 552/515)
  • Publication number: 20140309417
    Abstract: The present invention relates to a process for the preparation of sterol derivatives comprising the reaction of an ?-epoxy compound with an amine in an alcohol comprising 3 to 5 carbon atoms as a solvent.
    Type: Application
    Filed: November 23, 2012
    Publication date: October 16, 2014
    Inventors: Marc Poirot, Michael Paillasse, Philippe De Medina, Sandrine Poirot
  • Publication number: 20140249122
    Abstract: The present invention relates to novel aminosteroid derivatives substituted in position 3 andor 6, and to the use thereof in the context of the treatment of type 2 diabetes and of insulin resistance.
    Type: Application
    Filed: October 16, 2012
    Publication date: September 4, 2014
    Applicants: UNIVERSITE NICE SOPHIA ANTIPOLIS, UNIVERSITE D'AIX-MARSEILLE, INSERM (Institut National de la Sante Et de la Recherche Medicate), CENTRE NATIONAL DE LA RECHERCHE SCIENTIFQUE
    Inventors: Roland Marinus Theodorus Govers, Jean-Michel Brunel
  • Publication number: 20140005156
    Abstract: Sterol derivatives of formula (I) and a method for the production of the compounds, a medicament using one of the compounds and a pharmaceutical composition comprising the medicament.
    Type: Application
    Filed: August 28, 2013
    Publication date: January 2, 2014
    Applicant: INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)
    Inventors: MARC POIROT, PHILIPPE DE MEDINA, SANDRINE POIROT
  • Publication number: 20130266645
    Abstract: The present invention relates to compounds derived from steroids of the general formula (I) wherein L represents a linker and R# represents a steroid residue, the use of compounds of the general formula (I) in medicine and for the prophylaxis and/or the treatment of infectious diseases. Furthermore described are pharmaceutical compositions containing at least one compound of the general formula (I). A further aspect of the invention relates to the synthesis of said compounds of the general formula (I).
    Type: Application
    Filed: October 6, 2011
    Publication date: October 10, 2013
    Applicant: Justus-Liebig-Universitat Giessen
    Inventors: Katja Becker, Reimar Krieg, Bruno Schönecker
  • Patent number: 8536160
    Abstract: Compounds of formula (I) wherein: the groups are as defined in the description, are useful for the preparation of medicaments for the treatment of cardiovascular disorders, in particular heart failure and hypertension. The compounds are inhibitors of the enzymatic activity of the Na+, K+-ATPase. They are useful for the preparation of a medicament for the treatment of a disease caused by the hypertensive effects of endogenous ouabain, such as renal failure progression in autosomal dominant polycystic renal disease (ADPKD), preeclamptic hypertension and proteinuria and renal failure progression in patients with adducin polymorphisms.
    Type: Grant
    Filed: April 11, 2007
    Date of Patent: September 17, 2013
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Alberto Cerri, Giorgio Fedrizzi, Alessandra Benicchio, Giuseppe Bianchi, Patrizia Ferrari, Mauro Gobbini, Rosamaria Micheletti, Marco Pozzi, Piero Enrico Scotti
  • Patent number: 8524694
    Abstract: Sterol derivatives of formula (I) and a method for the production of the compounds, a medicament using one of the compounds and a pharmaceutical composition comprising the medicament.
    Type: Grant
    Filed: April 1, 2011
    Date of Patent: September 3, 2013
    Assignee: Institut National de la Sante et de la Recherche Medicale (INSERM)
    Inventors: Marc Poirot, Philippe De Medina, Sandrine Poirot
  • Publication number: 20130102577
    Abstract: The present invention relates to SHIP inhibitor compounds and methods for using these compounds. In particular, the present invention discloses the following methods: (i) a method of treating graft versus host disease in a subject; (ii) a method of inhibiting a SHIP1 protein in a cell; (iii) a method of selectively inhibiting a SHIP1 protein in a cell; (iv) a method for treating or preventing graft-versus-host disease (GVHD) in a recipient of an organ or tissue transplant; (v) a method of modulating SHIP activity in a cell expressing SHIP1 or SHIP2; (vi) a method of ex vivo or in vitro treatment of transplants; (vii) a method of inhibiting tumor growth and metastasis in a subject; (viii) a method of treating a hematologic malignancy in a subject; (ix) a method of inducing apoptosis of multiple myeloma cells; (x) a method of treating multiple myeloma in a subject; (xi) a method of inhibiting the proliferation of a human breast cancer cell; and (xii) a method of treating breast cancer in a subject.
    Type: Application
    Filed: April 11, 2011
    Publication date: April 25, 2013
    Applicant: The Research Foundation of the State University of New York
    Inventors: William G. Kerr, John D. Chisholm
  • Patent number: 7947668
    Abstract: Sterol derivatives of formula (I) and a method for the production of the compounds, a medicament using one of the compounds and a pharmaceutical composition comprising the medicament.
    Type: Grant
    Filed: April 18, 2003
    Date of Patent: May 24, 2011
    Assignee: Institut National de la Sante et de la Recherche Medicale
    Inventors: Marc Poirot, Philippe De Medina, Sandrine Poirot
  • Patent number: 7867990
    Abstract: The present invention relates to steroid hormone products, such as oral contraceptive products, including at least one steroid active ingredient mixed with an excipient and having improved dissolution and release rate properties. The invention further relates to methods for making such steroid hormone products, wherein a mixture of the hormone and the excipient is subjected to sufficient mechanical energy to form a powder blend wherein the hormone is stabilized by the excipient in substantially non-crystalline form.
    Type: Grant
    Filed: December 13, 2001
    Date of Patent: January 11, 2011
    Assignee: Ortho-McNeil Pharmaceutical, Inc.
    Inventors: Thomas Schultz, Bradley A. Clark, Angela Falzone
  • Publication number: 20100069627
    Abstract: The invention relates to a diastereoselective method for obtaining a primary amine on a steroid, comprising the reduction of an oxime by lithium in ammonia at a low temperature in an ether/alcohol mixture.
    Type: Application
    Filed: June 12, 2009
    Publication date: March 18, 2010
    Applicant: SANOFI-AVENTIS
    Inventors: Gilles ODDON, Daniel BERNARD, Gerard CAZENAVE, Andre SIMONNET, Joelle BOUSQUET-FRANCES
  • Patent number: 7196074
    Abstract: Methods of using 7?,11?-dimethyl-17?-hydroxyestra-4,14-dien-3-one (III) and 17 esters thereof for various hormonal therapies, oral and parenteral dosage forms comprising these actives, and processes for their preparation.
    Type: Grant
    Filed: October 28, 2002
    Date of Patent: March 27, 2007
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Richard P. Blye, Hyun K. Kim, Pemmaraju Narasimha Rao, Carmie Kirk Acosta
  • Patent number: 7109360
    Abstract: The invention describes new compounds as pharmaceutical active ingredients, which have in vitro a higher affinity to estrogen receptor preparations from rat prostates than to estrogen receptor preparations from rat uteri and in vivo a preferential action on bone rather than the uterus, their production, their therapeutic use and pharmaceutical dispensing forms that contain the new compounds. The new compounds are 16?- and 16?-hydroxy-estra-1,3,5(10)-estratrienes, which carry additional substituents on the steroid skeleton and can have one or more additional double bonds in the B-, C- and/or D-rings.
    Type: Grant
    Filed: February 4, 2000
    Date of Patent: September 19, 2006
    Assignee: Schering AG
    Inventors: Hermann Kuenzer, Rudolf Knauthe, Monika Lessl, Karl-Heinrich Fritzemeier, Christa Hegele-Hartung, Ulf Boemer, Gerd Mueller, Dirk Kosemund
  • Patent number: 7037907
    Abstract: A conjugated prodrug of an estradiol compound conjugated to a biological activity modifying agent.
    Type: Grant
    Filed: October 13, 2000
    Date of Patent: May 2, 2006
    Assignee: The University of Melbourne
    Inventors: Alastair George Stewart, David James McAllister, Maree Patricia Collis, Alan Duncan Robertson
  • Publication number: 20040259849
    Abstract: This invention relates to steroidal compounds having the formula (I), wherein: R1 is O, (H,H), (H,OH), NOH, whereby OH is optionally etherified or esterified; R2 and R3 are independently hydrogen or (C1-4) alkyl and at least one of R2 and R3 is (C1-4) alkyl; R4 is hydrogen, or (C1-15) acyl for use in androgen-related treatments, such as androgen insufficiency and male or female contraception.
    Type: Application
    Filed: March 11, 2004
    Publication date: December 23, 2004
    Inventors: J Jaap Van Der Louw, D Dirk Leysen, M.E. Marcel Evert De Gooijer
  • Patent number: 6780854
    Abstract: Novel, orally active androgens are 7&agr;-substituted &Dgr;14-nandrolone derivatives. The compounds satisfy the general formula: wherein R1 is O, (H,H), (H,OR), NOR, with R being hydrogen, (C1-6) alkyl, or (C,1-6) acyl; R2 is selected from the group consisting of (C2-4) alkyl, (C2-4) alkenyl, or (C2-4) alkynyl, each optionally substituted by halogen; or R2 is cyclopropyl, or cyclopropenyl, each optionally substituted by (C1-2) alkyl, or halogen; R3 is hydrogen, (C1-2) alkyl, or ethenyl; R4 is (C1-2) alkyl; R5 is hydrogen, or (C1-15) acyl; and the dotted lines indicate optional bonds.
    Type: Grant
    Filed: October 24, 2002
    Date of Patent: August 24, 2004
    Assignee: Akzo Nobel NV
    Inventors: Hubert Jan Jozef Loozen, Dirk Leysen, Jaap van der Louw
  • Publication number: 20040138186
    Abstract: A compound of the formula 1
    Type: Application
    Filed: July 21, 2003
    Publication date: July 15, 2004
    Applicant: Inflazyme Pharmaceuticals Ltd.
    Inventors: Jeffery R. Raymond, Claudia E. Kasserra, Yaping Shen
  • Publication number: 20040097406
    Abstract: The invention provides compositions comprising formula 1 steroids, e.g., 16&agr;-bromo-3&bgr;-hydroxy-5&agr;-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&agr;-bromo-3&bgr;-hydroxy-5&agr;-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: June 25, 2003
    Publication date: May 20, 2004
    Inventors: Clarence Nathaniel Ahlem, James Martin Frincke, Luis Daniel dos Anjos de Carvalho, William Heggie, Patrick T. Prendergast, Christopher L. Reading, Krupakar Paul Thadikonda, Russell Neil Vernon
  • Publication number: 20040092492
    Abstract: Compounds of general formula I as well as their pharmaceutically compatible salts are described, in which R1 stands for hydrogen, C1- to C6-alkyl, COR4, COOR4, COSR4 or CONHR5, in which R4 is C1- to C6-alkyl or unsubstituted or substituted aryl and in which R5 is hydrogen, C1- to C6-alkyl or unsubstituted or substituted aryl, in which R2 also stands for hydrogen, C1- to C6-alkyl or C1- to C6-acyl, and R3 stands for a CnF2n+1 group, in which n=1, 2 or 3, or a CH2O(CH2)mCnF2n+1 group, in which m=0 or 1 and n=1, 2 or 3. In addition, a process for the production of the compounds with general formula I is indicated. The compounds can be used for the production of pharmaceutical agents.
    Type: Application
    Filed: May 5, 2003
    Publication date: May 13, 2004
    Applicant: Schering AG
    Inventors: Sven Ring, Gerd Schubert, Ingo Tornus, Guenter Kaufmann, Walter Elger, Birgitt Schneider
  • Publication number: 20040087565
    Abstract: This invention describes the new 9&agr;-substituted estratrienes of general formula I 1
    Type: Application
    Filed: June 11, 2003
    Publication date: May 6, 2004
    Applicant: Schering AG
    Inventors: Dirk Kosemund, Gerd Mueller, Alexander Hillisch, Karl-Heinrich Fritzemeier, Peter Muhn
  • 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: 6579864
    Abstract: The invention concerns a 3-methylene steroid derivative having general formula (1) wherein R1 is H or together with R3 forms a &bgr;-epoxide or R1 is absent if there is a 5-10 or 4-5 double bond; R2 is (C1-C5) alkyl or CF3; R3 is &bgr;H, &bgr;CH3 or together with R1 forms a &bgr;-epoxide or R3 is absent if there is a 5-10 double bond; R4 is H, lower alkyl; Y is [H, H], [OH, H], ═O, [OH, lower alkyl], [OH, (C2-C5)alkenyl], [OH, (C2-C5)alkynyl] or (C1-C6) alkylidene, whereby said alkyl, alkenyl, alkynyl and alkylidene is optionally halogenated; ═NOR5, whereby R5 is H, lower alkyl; dotted lines represent an optional double bond, or prodrugs thereof for the treatment of arthritic diseases and/or autoimmune diseases.
    Type: Grant
    Filed: May 29, 2002
    Date of Patent: June 17, 2003
    Assignee: Akzo Nobel NV
    Inventors: Ralf Plate, Wilhelmina Maria Bagchus
  • Publication number: 20030087887
    Abstract: Compounds of the general formula I 1
    Type: Application
    Filed: March 21, 2002
    Publication date: May 8, 2003
    Inventor: Tore Duvold
  • Publication number: 20030087886
    Abstract: Novel, orally active androgens are 7&agr;-substituted &Dgr;14-nandrolone derivatives.
    Type: Application
    Filed: October 24, 2002
    Publication date: May 8, 2003
    Inventors: Hubert Jan Jozef Loozen, Dirk Leysen, Jaap van der Louw
  • Patent number: 6518262
    Abstract: The invention relates to 22R-hydroxycholesta-8,14-diene derivatives having general formula (I) wherein R1 is OR, OS03H or ═NOR; with R being H, (C1-6)alkyl or (C1-6)acyl; each of R2 and R3 is independently hydrogen or (C1-6)alkyl; R4 is hydrogen, (C1-6)alkyl or (C1-6)acyl; R5 is hydrogen; or R5 designates, together with R6, an additional bond between the carbon atoms at which R5 and R6 are placed; R6 is hydrogen, hydroxy or halogen; or R6 designates, together with R5, an additional bond between the carbon atoms at which R6 and R5 are placed; each of R7 and R8 is independently hydrogen or (C1-4)alkyl, optionally substituted with OH, (C1-4)alkoxy, or halogen; or a pharmaceutically acceptable salt thereof. The compounds of the invention have meiosis inhibiting activity and can be used for the control of fertility.
    Type: Grant
    Filed: August 22, 2001
    Date of Patent: February 11, 2003
    Assignee: Akzo Nobel N.V.
    Inventors: D. Leysen, J. van der Louw, R. G. J. M. Hanssen, Anja Wiersma
  • Publication number: 20020193357
    Abstract: A compound of formula (I): 1
    Type: Application
    Filed: May 2, 2002
    Publication date: December 19, 2002
    Inventors: Ching Song, Shutsung Liao
  • Publication number: 20020173669
    Abstract: The present invention relates to steroid hormone products, such as oral contraceptive products, including at least one steroid active ingredient mixed with an excipient and having improved dissolution and release rate properties. The invention further relates to methods for making such steroid hormone products, wherein a mixture of the hormone and the excipient is subjected to sufficient mechanical energy to form a powder blend wherein the hormone is stabilized by the excipient in substantially non-crystalline form.
    Type: Application
    Filed: December 13, 2001
    Publication date: November 21, 2002
    Inventors: Thomas Schultz, Bradley A. Clark, Angela Falzone
  • Publication number: 20020142998
    Abstract: This invention is directed to compounds that provide for sustained systemic concentrations of therapeutic or prophylactic agents following administration to animals. This invention is also directed to pharmaceutical compositions including and methods using such compounds.
    Type: Application
    Filed: October 9, 2001
    Publication date: October 3, 2002
    Inventors: Kenneth C. Cundy, Mark A. Gallop
  • Publication number: 20020091278
    Abstract: A series of novel steroid derivatives are described. The steroid derivatives are antibacterial agents. The steroid derivatives also act to sensitize bacteria to other antibiotics including erythromycin and novobiocin.
    Type: Application
    Filed: August 15, 2001
    Publication date: July 11, 2002
    Inventors: Paul B. Savage, Chunhong Li
  • Patent number: 6413951
    Abstract: The invention relates to 20&xgr;-fluoropregna-4,17(20)-dien-3-on-21-oic acid ethyl ester, 20&xgr;-fluoro-3&bgr;-hydroxypregna-5,17(20)-dien-21-oic acid ethyl ester, 20&xgr;-fluoro-21-hydroxypregna-4,17 (20)-dien-3-one, 20&xgr;-fluoropregna-5,17(20)-dien-3&bgr;,21-diol and related compounds and to compositions incorporating these compounds, as well as the inhibition of C17,20 lyase, 5&agr;-reductase and C17-hydroxylase, and to the use of these compounds in the treatment of androgen and estrogen mediated or dependent disorders, including benign prostatic hyperplasia, prostate cancer, breast cancer and DHT-mediated disorders such as acne and hirsutism. Treatment of disorders related to the over synthesis of cortisol, for example, Cushing's Syndrome are also included. The treatment of androgen-dependent disorders also includes a combination therapy with known androgen-receptor antagonists, such as flutamide.
    Type: Grant
    Filed: June 21, 2001
    Date of Patent: July 2, 2002
    Assignee: Aventis Pharmaceuticals, Inc.
    Inventors: Norton P. Peet, Philip M. Weintraub, Joseph P. Burkhart, Cynthia A. Gates
  • Publication number: 20020082433
    Abstract: Compositions and methods for treating mammalian disease characterized by undesirable angiogenesis by administering derivatives of 2-methoxyestradiol of the general formula: 1
    Type: Application
    Filed: August 24, 2001
    Publication date: June 27, 2002
    Inventors: Gregory E. Agoston, Jamshed H. Shah, Kimberly A. Hunsucker, Victor S. Pribluda, Theresa M. LaVallee, Shawn J. Green, Christopher J. Herbstritt, Xiaoguo H. Zhan, Anthony M. Treston
  • Publication number: 20020082221
    Abstract: Novel nitric-oxide releasing lipid molecules are provided which comprise a lipid molecule selected from (a) phosphoglycerides, (b) lipids having a sphingosine base as a backbone, (c) monoacylglyerols, (d) diacylglycerols, (e) glycosylacylglycerols, and (f) sterol compounds of the formula: 1
    Type: Application
    Filed: December 21, 2000
    Publication date: June 27, 2002
    Applicant: Scimed Life Systems, Inc.
    Inventors: Robert A. Herrmann, Wendy Naimark
  • Publication number: 20020065257
    Abstract: The invention is directed to a novel class of steroids which exhibit potent antiprogestational activity.
    Type: Application
    Filed: July 2, 2001
    Publication date: May 30, 2002
    Applicant: RESEARCH TRIANGLE INSTITUTE
    Inventors: C. Edgar Cook, John A. Kepler, Gary S. Bartley, Rupa S. Shetty
  • Publication number: 20020019548
    Abstract: The invention related to 20&xgr;-fluoropregna-4,17(20)-dien-3-on-21-oic acid ethyl ester, 20&xgr;-fluoro-3&bgr;-hydroxypregna-4,17(20)-dien-21-oic acid ethyl ester, 20&xgr;-fluoro-21-hydroxypregna-4,17(20)-dien-3-one, 20&xgr;-fluoropregna-4,17(20)-dien-3&bgr;,21-diol and related compounds and to compositions incorporating these compounds, as well as the inhibition of C17,20 lyase, 5&agr;-reductase and C17-hydroxylase, and to the use of these compounds in the treatment of androgen and estrogen mediated or dependent disorders, including benign prostatic hyperplasia, prostate cancer, breast cancer and DHT-mediated disorders such as acne and hirsutism. Treatment of disorders related to the over synthesis of cortisol, for example, Cushing's Syndrome are also included. The treatment of androgen-dependent disorders also includes a combination therapy with known androgen-receptor antagonists, such as flutamide.
    Type: Application
    Filed: June 21, 2001
    Publication date: February 14, 2002
    Inventors: Norton P. Peet, Philip M. Weintraub, Joseph P. Burkhart, Cynthia A. Gates
  • Publication number: 20020002294
    Abstract: Compositions and methods for treating mammalian disease characterized by undesirable angiogenesis by administering derivatives of 2-methoxyestradiol of the general formula: 1
    Type: Application
    Filed: July 5, 2001
    Publication date: January 3, 2002
    Inventors: Robert J. D' Amato, Ravi K. Varma, Rudiger G. Haugwitz, Mark Cushman
  • Patent number: 6262282
    Abstract: The invention relates to 17&bgr;-allyloxy(thio)alkyl-androstane derivatives having general formula (I) wherein R1 is (H, OR), (H, OSO3H) or NOR; with R being H, (C1-6)alkyl or (C1-6)acyl; each of R2 and R3 is independently hydrogen or (C1-6)alkyl; n is 0, 1 or 2; X is O, S, S(O) or S(O)2; each of R4 and R5 is independently hydrogen or (C1-4)alkyl; each of R6, R7 and R8 is independently hydrogen, phenyl, halogen or (C1-4)alkyl, optionally substituted by hydroxy, (C1-4) alkoxy or halogen; or R7 and R8 together with the carbon atom to which they are bound form a (C3-6)cycloalkane ring; or R6 and R7 together with the carbon atoms to which they are bound form a (C5-6) cycloalkene ring; and wherein the dotted lines indicate a &Dgr;7 or a &Dgr;8 double bond, or a pair of conjugated double bonds selected from &Dgr;7,14, &Dgr;8,14 and &Dgr;6,8(14); or a pharmaceutically acceptable salt thereof. The compounds of the invention have meiosis activating activity and can be used for the control of fertility.
    Type: Grant
    Filed: December 3, 1999
    Date of Patent: July 17, 2001
    Assignee: Akzo Nobel N.V.
    Inventors: Johannes Antonius Joseph Leemhuis, Jaap van der Louw, Marinus Bernard Groen
  • Patent number: 6262042
    Abstract: The invention is directed to a novel class of steroids which exhibit potent antiprogestational activity.
    Type: Grant
    Filed: May 29, 1998
    Date of Patent: July 17, 2001
    Assignee: Research Triangle Institute
    Inventors: C. Edgar Cook, John A. Kepler, Gary S. Bartley
  • Patent number: 6251887
    Abstract: The invention relates to 17&bgr;-aryl(arylmethyl)oxy(thio)alkyl-androstane derivatives having general formula (I), wherein R1 is (H,OR), (H,OSO3H) or NOR; with R being H, (C1-6)alkyl or (C1-6)acyl; each of R2 and R3 is independently hydrogen or (C1-6)alyl; n is 0, 1, or 2; X is O, S, S(O) or S(O)2; m is 0 or 1; each of R4, R5 and R6 is independently hydrogen, hydroxy, (C1-4)alkoxy, halogen, NR7R8 or (C1-4)alkyl, optionally substituted by hydroxy, alkoxy, halogen or oxo; each of R7 and R8 is independently hydrogen or (C1-4)alkyl, and wherein the dotted lines indicate a &Dgr;7 or a &Dgr;8 double bond, or a pair of conjugated double bonds selected from &Dgr;7,14, &Dgr;8,14 and &Dgr;6,8(14); or a pharmaceutically acceptable salt thereof. The compounds of the invention have meiosis regulating activity and can be used for the control of fertility.
    Type: Grant
    Filed: June 16, 2000
    Date of Patent: June 26, 2001
    Assignee: Akzo Nobel N.V.
    Inventors: Christian Heijmans, Jaap van der Louw
  • Patent number: 6180803
    Abstract: The invention relates to compounds of the formula: in which R1, R2, R3, R4, R5, R6, n and X are as defined in the specification, and to pharmaceutical compositions containing them. These compounds are excellent progestogens which are devoid of residual androgenic activity.
    Type: Grant
    Filed: November 5, 1998
    Date of Patent: January 30, 2001
    Assignee: Laboratoire Theramex
    Inventors: Alain Piasco, Jean Lafay, R{acute over (e)}mi Delansorne, Jacques Paris, Jean-Claude Pascal
  • 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: 5990328
    Abstract: The present invention provides 4-nitro-.DELTA..sup.4 -3-ketosteroids, their use as steroid C.sub.17-20 lyase and 5.alpha.-reductase inhibitors and to a novel process for preparing a compound of the formula: ##STR1## comprising sequentially: a) reacting a starting compound of the formula ##STR2## with an effective amount of a strong base at an elevated or suitable temperature for a time sufficient to create the corresponding thermodynamic dienolate, followed by addition of a neutral nitrating agent to produce the 4-nitrosteroid; and then;b) reacting the 4-nitrosteroid with a suitable reducing agent.
    Type: Grant
    Filed: February 24, 1999
    Date of Patent: November 23, 1999
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Philip M. Weintraub, Michael R. Angelastro, Cynthia A. Gates, Gary Alan Flynn, Timothy Thomas Curran, Chi-Hsin Richard King
  • Patent number: 5965550
    Abstract: The invention discloses 3-ketosteroids of the following formula used to inhibit steroid C.sub.17-20 lyase: ##STR1## wherein R is OH, C.sub.1 -C.sub.6 alkanoyl, C.sub.1 -C.sub.6 alkanoyloxy, C.sub.1 -C.sub.4 alkanol, COCH.sub.2 OH, CO.sub.2 H, CONR.sub.7 R.sub.8, cyclopropyloxy, cyclopropylamino, acetylthioalkane, 2,2-dimethyldioxolan4-yl, 1,2-dihydroxyethyl and C.sub.1-4 alkylthiol;R.sub.1 is hydrogen, hydroxy or C.sub.1-6 alkyl;R and R.sub.1 together may indicate .dbd.O, that is an oxygen double bonded to the 17 carbon;R.sub.2, R.sub.3, and R.sub.4 are each independently hydrogen or C.sub.1 -C.sub.6 alkyl;R.sub.5 and R.sub.6 are each independently hydrogen or OH;R.sub.5 and R.sub.6 together may indicate .dbd.O, that is an oxygen double bonded to the 11 carbon;R.sub.7 is hydrogen or C.sub.1 -C.sub.8 alkyl;R.sub.8 is C.sub.1 -C.sub.8 alkyl; andwith the proviso that, when R is OH, then R.sub.1 is hydrogen; andwith the proviso that, when R.sub.5 is OH, then R.sub.6 is hydrogen.
    Type: Grant
    Filed: January 22, 1998
    Date of Patent: October 12, 1999
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Philip M. Weintraub, Michael R. Angelastro, Cynthia A. Gates, Timothy Thomas Curran, Gary Alan Flynn, Chi-Hsin Richard King
  • Patent number: 5952319
    Abstract: An androgenic steroid compound of the formula: ##STR1## wherein: X, Y, Z, R.sup.1, R.sup.2, R.sup.3, R.sup.5 and R.sup.6 are as defined herein.
    Type: Grant
    Filed: November 26, 1997
    Date of Patent: September 14, 1999
    Assignee: Research Triangle Institute
    Inventors: C. Edgar Cook, John A. Kepler, Yue-Wei Lee, Mansukh C. Wani
  • Patent number: 5922703
    Abstract: Urethane-containing amino steroids having the general chemical formula: ##STR1## wherein a, b, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.14 and Z are as defined in the specification. Also disclosed are pharmaceutical composition and the use of the compounds/composition in the treatment of congestive heart failure.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: July 13, 1999
    Assignee: The Procter & Gamble Company
    Inventors: Chia-Nien Yu, Gilles Yves Genain, Rachel Boujo
  • Patent number: 5902888
    Abstract: Disclosed are 6.alpha.-derivatized estriol compounds which, when conjugated to a protein, are useful in the in vivo preparation of antibodies specific to estriol. When labeled with a detectable label, the estriol derivatives are useful as haptens in a competitive immunoassay for estriol which demonstrate superior sensitivity with respect to estriol specific antibodies.
    Type: Grant
    Filed: November 14, 1997
    Date of Patent: May 11, 1999
    Assignee: Bayer Corporation
    Inventors: James V. Freeman, Gary M. Johnson
  • 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: 5750744
    Abstract: The present invention provides 4-nitro-.DELTA..sup.4 -3-ketosteroids, their use as steroid C.sub.17-20 lyase and 5.alpha.-reductase inhibitors and to a novel process for preparing a compound of the formula: ##STR1## comprising sequentially: a) reacting a starting compound of the formula ##STR2## with an effective amount of a strong base at an elevated or suitable temperature for a time sufficient to create the corresponding thermodynamic dienolate, followed by addition of a neutral nitrating agent to produce the 4-nitro-steroid; and then;b) reacting the 4-nitrosteroid with a suitable reducing agent.
    Type: Grant
    Filed: February 11, 1997
    Date of Patent: May 12, 1998
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Philip M. Weintraub, Cynthia A. Gates, Michael R. Angelastro, Gary Alan Flynn, Chi-Hsin Richard King, Timothy Thomas Curran
  • Patent number: 5646316
    Abstract: The present invention relates to a bile acid derivative, which comprises a bile acid derivatized at the carboxyl group with a hydroxamic acid or hydroxamate ester. The carboxyl group in the bile acid compound can also be derivatized with an amino acid or oligopeptide, whose C-terminus is derivatized with a hydroxamic acid or a hydroxamate ester. The present invention also relates to a method of use of a bile acid or a bile acid derivative to inhibit a metalloproteinase enzyme, comprising contacting a metalloproteinase with an effective amount of a bile acid or bile acid derivative. In another embodiment, the present invention further relates to a method of use of a bile acid or bile acid derivative to therapeutically treat a disease, which is ameliorated by inhibiting a metalloproteinase enzyme. In this method, a therapeutically effective amount of a bile acid, a bile acid derivative or physiologically acceptable salts thereof, is administered to a human or other mammal.
    Type: Grant
    Filed: April 25, 1995
    Date of Patent: July 8, 1997
    Assignee: OsteoArthritis Sciences, Inc.
    Inventors: Alan R. Jacobson, Douglas G. Gabler, Jozef Oleksyszyn
  • Patent number: 5502044
    Abstract: The present invention relates to a compound of formula (I) ##STR1## wherein (x) and (y) are single or double bonds; A is a ##STR2## R and R.sup.3 are hydrogen or acyl; R.sup.1 is hydrogen or fluorine;and wherein:when (y) is a single bond, R.sup.2 is hydrogen, fluorine methyl, trifluoromethyl;when (y) is a double bond, R.sup.2 is methylene provided that when one of (x) or (y) is a double bond the other is a single bond and at least one of R.sub.1 and R.sub.2 is fluorine or trifluoromethyl or a pharmaceutically acceptable salt thereof. The compounds of formula (I) are useful as aromatase inhibitors.
    Type: Grant
    Filed: February 14, 1994
    Date of Patent: March 26, 1996
    Assignee: Farmitalia Carlo Erba S.r.l.
    Inventors: Franco Buzzetti, Antonio Longo, Enrico Di Salle
  • Patent number: 5486511
    Abstract: This invention is directed to 4-amino-17.beta.-(cyclopropyloxy)androst-4-en-3-one, 4-amino-17.beta.-(cyclopropylylamino)androst-4-en-3-one and related compounds, a process for their synthesis, a pharmaceutical composition having C.sub.17-20 lyase and 5.alpha.-reductase inhibitory activity, the use of the present compounds as C.sub.17-20 lyase and 5.alpha.-reductase inhibitors and also to a method for using such compounds in the treatment of androgen and/or estrogen dependent disorders, including bengin prostatic hyperplasia, breast cancer and prostatic cancer. The 4-amino compounds are prepared by the reaction of the appropriate 4,5-epoxide with sodium azide in an inert solvent in the presence of a catalytic amount of strong acid under appropriate reaction conditions. Alternatively, the 4-amino compounds are prepared by first nitration and then reduction of the appropriate steroid under appropriate reaction conditions.
    Type: Grant
    Filed: May 2, 1994
    Date of Patent: January 23, 1996
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Philip M. Weintraub, Cynthia A. Gates, Michael R. Angelastro, Timothy T. Curran, J. O'Neal Johnston
  • Patent number: 5486603
    Abstract: The present invention relates to an oligonucleotide or analog thereof conjugated to a molecule comprising a structure, which structure (a) is of substantially fixed conformation; (b) contains, is directly attached to, or is attached to a carbon atom that is directly attached to, an first amine; and (c) contains, is directly attached to, or is attached to an atom that is directly attached to a phosphate, a second amine, or a cationic sulfur. In a preferred embodiment, the structure consists of at least a nonaromatic cyclic portion or substituted derivative thereof. In a specific embodiment, the structure is a nonaromatic cyclic compound. In another embodiment, the molecule is a steroid. In yet another particular aspect, the structure is an aromatic compound. In another embodiment, the structure can bind to a nucleic acid sequence in a nonintercalative manner.
    Type: Grant
    Filed: June 22, 1992
    Date of Patent: January 23, 1996
    Assignee: Gilead Sciences, Inc.
    Inventor: Chris A. Buhr