The A Ring Is A Benzene Ring (e.g., Estriols, Etc.) Patents (Class 552/617)
  • Patent number: 11053274
    Abstract: The present invention relates to a process for the preparation of a compound of formula (I) said process comprising the steps of: a) reacting a compound of formula (II), with an acylating or a silylating agent to produce a compound of formula (III), wherein P1 and P2 are each independently a protecting group selected from R2—Si—R3R4, or R1CO—, wherein R1 is a group selected from C1-6alkyl or C3-6cycloalkyl, each group being optionally substituted by one or more substituents independently selected from fluoro or C1-4alkyl; R2, R3 and R4 are each independently a group selected from C1-6alkyl or phenyl, each group being optionally substituted by one or more substituents independently selected from fluoro or C1-4alkyl; b) reacting the compound of formula (III) in the presence of palladium acetate or a derivative thereof to produce compound of formula (IV); and c) reacting the compound of formula (IV) with a reducing agent to produce compound of formula (I).
    Type: Grant
    Filed: June 1, 2012
    Date of Patent: July 6, 2021
    Assignee: ESTETRA S.P.R.L.
    Inventor: Jean-Claude Pascal
  • Patent number: 9315539
    Abstract: The present invention relates to novel 11-? estradiol ester compounds and their use as locally active estrogens in the treatment of the symptomology of menopause and to treat estrogen sensitive cancers, including breast cancer.
    Type: Grant
    Filed: October 1, 2003
    Date of Patent: April 19, 2016
    Assignee: YALE UNIVERSITY
    Inventor: Richard Hochberg
  • Publication number: 20150105362
    Abstract: A process is provided for the making of estetrol starting from a 3-A-oxy-estra-1,3,5(10),15-tetraen-17-one, wherein A is an C1-C5 alkyl group, preferably a methyl group, or a C7-C12 benzylic group, preferably a benzyl group. This process is particularly suitable to industry.
    Type: Application
    Filed: December 19, 2014
    Publication date: April 16, 2015
    Applicant: Pantarhei Bioscience B.V.
    Inventors: Mark Theodoor Verhaar, Thomas Koch, Erwin Gerardus Jacobus Warmerdam
  • Patent number: 8987484
    Abstract: The present invention relates to a process for the preparation of a compound of formula (I), hydrates or solvates thereof.
    Type: Grant
    Filed: October 5, 2012
    Date of Patent: March 24, 2015
    Assignee: Estetra S.P.R.L.
    Inventor: Jean-Claude Pascal
  • Publication number: 20150018322
    Abstract: Various prodrug compounds having the general structure: Active agent-(acid)-(linker)-SO2NR1R2 are described herein. Compounds having this general structure were shown to be more orally active than the unmodified parent molecule.
    Type: Application
    Filed: July 11, 2014
    Publication date: January 15, 2015
    Inventors: Klaus Nickisch, Bindu Santhamma, Gulzar Ahmed, Frederick Meece, Walter Elger, Ralf Wyrwa, Hareesh Nair
  • Publication number: 20140243539
    Abstract: The present invention relates to a process for the preparation of a compound of formula (I), hydrates or solvates thereof.
    Type: Application
    Filed: October 5, 2012
    Publication date: August 28, 2014
    Applicant: Estetra S.P.R.L.
    Inventor: Jean-Claude Pascal
  • Publication number: 20140235882
    Abstract: The present invention relates to a process for the preparation of estra-1,3,5(10)-trien-3,15?,16?,17?-tetraol (estetrol), via a silyl enol ether derivative 17-B-oxy-3-A-oxy-estra-1,3,5(10),16-tetraene, wherein A is a protecting group and B is —Si(R2)3. The invention further relates to a process for the synthesis of 3-A-oxy-estra-1,3,5(10),15-tetraen-17-one, wherein A is a protecting group, via said silyl enol ether derivative.
    Type: Application
    Filed: July 18, 2012
    Publication date: August 21, 2014
    Inventors: Johannes Jan Platteeuw, Herman Jan Tijmen Coelingh Bennink, Franciscus Wilhelmus Petrus Damen, Michiel Christine Alexander Van Vliet
  • Publication number: 20140107091
    Abstract: The present invention relates to a process for the preparation of a compound of formula (I) comprising the steps of a) reacting a compound of formula (II) with a silylating or an acylating agent to produce compound of formula (III), wherein P1 is a protecting group selected from R2Si—R3R4 or R1CO—, R1 is a group selected from C1-6alkyl or C3-6cycloalkyl, each group being optionally substituted by one or more substituents independently selected from fluoro or C1-4alkyl; R2, R3 and R4 are each independently a group selected from C1-6alkyl or phenyl, each group being optionally substituted by one or more substituents independently selected from fluoro or C1-4alkyl; b) halogenation or sulfinylation of the compound of formula (III) to produce a compound of formula (IV); wherein X is halo, or —O—SO—R5, and R5 is a group selected from C6-10aryl or heteroaryl, each group being optionally substituted by one or more substituents independently selected from chloro or C1-4alkyl; c) dehalogenation or desulfinylation of th
    Type: Application
    Filed: June 1, 2012
    Publication date: April 17, 2014
    Applicant: ESTETRA S.A.
    Inventor: Jean-Claude Pascal
  • Publication number: 20140107358
    Abstract: The present invention relates to a process for the preparation of a compound of formula (I) said process comprising the steps of: a) reacting a compound of formula (II), with an acylating or a silylating agent to produce a compound of formula (III), wherein P1 and P2 are each independently a protecting group selected from R2?Si—R3R4, or R1CO—, wherein R1 is a group selected from C1-6alkyl or C3-6cycloalkyl, each group being optionally substituted by one or more substituents independently selected from fluoro or C1-4alkyl; R2, R3 and R4 are each independently a group selected from C1-6alkyl or phenyl, each group being optionally substituted by one or more substituents independently selected from fluoro or C1-4alkyl; b) reacting the compound of formula (III) in the presence of palladium acetate or a derivative thereof to produce compound of formula (IV); and c) reacting the compound of formula (IV) with a reducing agent to produce compound of formula (I).
    Type: Application
    Filed: June 1, 2012
    Publication date: April 17, 2014
    Applicant: ESTETRA S.A.
    Inventor: Jean-Claude Pascal
  • 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
  • Publication number: 20120172344
    Abstract: Provided is an insulin-producing cell inducer, an enhancer for glucose intake of muscles, and a therapeutic agent for diabetes or diabetes complications, wherein an active ingredient of those provided is an estrogenic compound such as estrogen and estradiol. With the present invention, functions of insulin-producing cells can be recovered since the insulin-producing cells are induced in pancreatic ducts, and blood glucose level can be immediately lowered since glucose in the blood can be effectively taken up by muscles; therefore, diabetes and diabetes complications can be prevented or treated.
    Type: Application
    Filed: July 16, 2010
    Publication date: July 5, 2012
    Applicant: KYUSHU UNIVERSITY, NATIONAL UNIVERSITY CORPORATION
    Inventor: Akari Inada
  • Publication number: 20110312929
    Abstract: The present invention relates to the use of estriol in the preparation of a pharmaceutical formulation for vaginal administration with the capacity to self-limit the absorption of estriol, for the prevention and/or the treatment of urogenital atrophy in women said women having a high probability of suffering from a cardiovascular pathology or suffering or having suffered from a cardiovascular pathology.
    Type: Application
    Filed: August 7, 2009
    Publication date: December 22, 2011
    Applicant: ITALFARMACO, S.A.
    Inventors: Álvaro Acebrón Fernández, Dolores Blanco Lousame, Jaime Moscoso Del Prado, Concepción Nieto Magro
  • Publication number: 20110201585
    Abstract: A method of reducing or inhibiting the risk of infection from sexually transmitted viral infections (STIs), such as HIV and HPV, comprising the topical administration of oestrogenic compounds, analogues or metabolites thereof or oestrogen agonists to a human penis. A method to increase keratinisation of the penile epithelium is also provided. Suitable formulations are also provided.
    Type: Application
    Filed: May 9, 2008
    Publication date: August 18, 2011
    Inventors: Roger Short, Andrew Pask
  • Publication number: 20090163458
    Abstract: The present disclosure relates generally to methods and compositions for treating symptoms of Parkinson's disease and/or other movement disorders. More particularly, the present disclosure describes a method for treating symptoms of Parkinson's disease and related disorders by administering a composition comprising one or more of the following active agents; estradiol, estriol, testosterone, and 19-nortestosterone. In addition, the compositions of the present invention can be used for enhancing or optimizing the effectiveness of neural stimulation in treating the symptoms of movement disorders such as Parkinson's disease.
    Type: Application
    Filed: November 6, 2008
    Publication date: June 25, 2009
    Inventor: Ellis L Kline
  • Patent number: 7507725
    Abstract: The invention relates to compounds which, acting as a prodrug and/or support, enable an active agent to be taken up by the erythrocytes and/or an active agent to bind to the erythrocytes. The uptake of these compounds by and/or the binding thereof to the erythrocytes is made possible by a group of formula —SO2NR1R2, wherein R1 and R2, independently of each other, mean a hydrogen atom, an acyl group, an alkyl group, a cycloalkyl group, an aryl group, a cyano group or a hydroxy group. The inventive prodrugs enable active agents such as endogenic substances, natural substances and synthetic substances with therapeutically useful properties which have a high “first path” effect, to be administered orally effectively or significantly improve the oral activity thereof.
    Type: Grant
    Filed: May 8, 2001
    Date of Patent: March 24, 2009
    Assignee: Schering AG
    Inventors: Walter Elger, Alexander Hillisch, Annemarie Hedden, Sigfrid Schwarz, Klaus Schollkopf
  • Publication number: 20080281112
    Abstract: A diamine includes a structure of formula (I), wherein X and Y are independently a divalence group selected from the group consisting of: —O—, —(C?O)—O—, —O—(C?O)—, —(C?O)—NH—, and —NH—(C?O)—; and R has a structure of formula (II): wherein R1, R2, R3, R4, R5, m, and n are as defined in Claim 1. A polyamic acid is prepared by reacting a diamine reactant including the aforesaid diamine of formula (I) with a tetracarboxylic dianhydride reactant. A liquid crystal orienting film contains a polyimide converted from the aforesaid polyamic acid.
    Type: Application
    Filed: May 9, 2007
    Publication date: November 13, 2008
    Inventors: Chuan-Ter Yan, Chih-Hsiung Huang, Chao-Ching Huang, Chin-Wang Kao, Tin-Hun Hung
  • Patent number: 7378404
    Abstract: This invention describes the new 8?-substituted estratrienes of general formula I in which R2, R3, R6, R6?, R7, R7?, R9, R11, R11?, R12, R14, R15, R15?, R16, R16?, R17 and R17? have the meanings that are indicated in the description, and R8 means a straight-chain or branched-chain, optionally partially or completely halogenated alkyl or alkenyl radical with up to 5 carbon atoms, an ethinyl- or prop-1-inyl radical, as pharmaceutical active ingredients that have in vitro a higher affinity to estrogen receptor preparations of rat prostates than to estrogen receptor preparations of rat uteri and in vivo preferably a preferential action on bone rather than the uterus and/or a pronounced action with respect to stimulation of the expression of 5HT2a-receptors and 5HT2a-transporters, their production, their therapeutic use and pharmaceutical dispensing forms that contain the new compounds.
    Type: Grant
    Filed: April 12, 2001
    Date of Patent: May 27, 2008
    Assignee: Schering Aktiengesellschaft
    Inventors: Olaf Peters, Alexander Hillisch, Ina Thieme, Walter Elger, Christa Hegele-Hartung, Uwe Kollenkirchen, Karl-Heinrich Fritzemeier, Vladimir Patchev
  • Patent number: 6894038
    Abstract: The invention relates to the use of esters of estriol, for example, an estriol 3,17-dipropionate or an estriol 3,17-dihexanoate, for the treatment of autoimmune diseases, such as multiple sclerosis (MS).
    Type: Grant
    Filed: February 27, 2003
    Date of Patent: May 17, 2005
    Assignee: Schering Aktiengesellschaft
    Inventors: Walter Elger, Sybille Beier, Harald Von Keyserlingk, Frank Dahlke
  • Publication number: 20040198670
    Abstract: The present invention relates to novel estrogenic compounds. The present invention also relates to methods of treating estrogen deprivation in a subject comprising administering novel estrogenic compounds. Additionally, the present invention relates to methods of synthesizing novel estrogenic compounds.
    Type: Application
    Filed: April 4, 2003
    Publication date: October 7, 2004
    Inventors: Edward N. Hill, Thomas W. Leonard, Robert R. Whittle
  • Patent number: 6670347
    Abstract: This invention relates to new 19-nor-17&agr;-pregna-1,3,5(10)-trien-17&bgr;-ols with a 21,16&agr;-lactone ring of formula II, process for their production and pharmaceutical preparations that contain these compounds as well as 17&agr;-cyanomethylated estra-1,3,5(10)-trienes, which produce intermediate products on the way to the 19-nor-17&agr;-pregna-1,3,5(10)-trien-17&bgr;-ols. The 19-nor-17&agr;-pregna-1,3,5(10)-trien-17&bgr;-ols produce novel selective estrogens, which contrast to standard estrogens, such as estradiol, show a preference for one of the two known estrogen receptors, estrogen receptor alpha.
    Type: Grant
    Filed: September 27, 2001
    Date of Patent: December 30, 2003
    Assignee: Schering AG
    Inventors: Gerd Müller, Uwe Kollenkirchen, Dirk Kosemund, Karl-Heinrich Fritzemeier, Walter Elger
  • Publication number: 20030134834
    Abstract: This invention describes the new 17&agr;-fluoroalkyl steroids of general formula I 1
    Type: Application
    Filed: November 27, 2002
    Publication date: July 17, 2003
    Applicant: Schering AG
    Inventors: Wolfgang Schwede, Arwed Cleve, Ulrich Klar, Gunter Neef, Kristof Chwalisz, Martin Schneider, Ulrike Fuhrmann, Holger Heb-Stumpp
  • Patent number: 6271220
    Abstract: The application discloses methods of treating mammalian diseases characterized by undesirable angiogenesis by administering compounds including those having the general formulae wherein A is a fused tropone having a general formula: wherein X is selected from the group consisting of hydrogen, hydroxy, carboxy, halogen, nitro, C1 to C12 alkenyl, C1 to C12 alkyl, C1 to C12 alkoxy, SR, NR2, OSO3−, OSO2NR2, HNSO3−, NHSO2NR2, SSO3−, SSO2NR2, wherein R is hydrogen or a C1 to C6 alkyl and the 17-ester and keto derivatives thereof, in a dosage sufficient to inhibit cell mitosis. The application discloses novel compounds used in the method of the invention.
    Type: Grant
    Filed: September 3, 1999
    Date of Patent: August 7, 2001
    Assignee: Allergan Sales, Inc.
    Inventors: Michael E. Garst, Timothy L. MacDonald
  • 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: 5798348
    Abstract: The pharmaceutical and/or cosmetic compositions for treatment of obesity and/or overweight contain an effective amount of a fatty-acid monoester of an estrogen and a fatty acid wherein the estrogen is estrone, diethylstilbestrol, estriol, estradiol or ethinyl estradiol and the fatty acid is oleic, linoleic, linolenic, stearic, palmitic, palmitoleic or arachidonic acids. The fatty-acid monoesters mimic the function of estrone monooleate, as a signal that informs the brain of the size of fat tissue mass. In preferred pharmaceutical and/or cosmetic compositions for intravenous injection the monoester is incorporated in a lipidic suspension, prepared from lipoproteins or from liposome components, such as soy oil and egg phospholipids. When administered to rats with a 15% of total adipose tissue, they produce weight reduction of about 10%, by a new and unexpected mechanism. They are useful for the treatment of obesity and/or overweight in mammals, with the advantages of high efficacy and low toxicity.
    Type: Grant
    Filed: October 30, 1996
    Date of Patent: August 25, 1998
    Assignee: Laboratorios S.A.L.V.A.T., S.A.
    Inventor: Maria Alemany
  • Patent number: 5705495
    Abstract: The invention relates to new sulfamate derivatives of 1,3,5(10)-estratriene derivatives of the general formula I ##STR1## wherein the 3-sulfamate moiety is acylated, sulfonated or amidosulfonated. Furthermore, methods for the production of the compound and pharmaceutical preparations containing this compound are described. The compounds according to the invention have an estrogenic effect.
    Type: Grant
    Filed: October 18, 1996
    Date of Patent: January 6, 1998
    Assignee: Jenapharm GmbH & Co. KG.
    Inventors: Sigfrid Schwarz, Walter Elger, Gudrun Reddersen, Birgitt Schneider, Ina Thieme, Margit Richter
  • Patent number: 5529993
    Abstract: A 14.alpha.,17.alpha.-bridged estratriene of formula I ##STR1## wherein (a) OR.sup.3 is in .alpha.-positionR.sup.1, R.sup.2 and R.sup.3, each independently are (i) hydrogen, (ii) ##STR2## in which R.sup.4 is an organic radical with up to 11 carbon atoms or (iii) --(CH.sub.2).sub.n COOH wherein n=1-4, or (iv) R.sup.1 is a benzyl, C.sub.1 -C.sub.8 alkyl or C.sub.3 -C.sub.5 cycloalkyl, or(b) OR.sup.3 is in .beta.-positionR.sup.1, R.sup.2 and R.sup.3, each independently are (i) hydrogen, (ii) an acyl group with 1 to 12 carbon atoms or (iii) R.sup.1 is C.sub.1 -C.sub.8 alkyl, and in both (a) and (b) A--B is an etheno or ethano bridge.
    Type: Grant
    Filed: November 29, 1990
    Date of Patent: June 25, 1996
    Assignee: Schering Aktiengesellschaft
    Inventors: Gerald Kirsch, Gunter Neef, Henry Laurent, Rudolf Wiechert, James Bull, Peter Esperling, Walter Elger, Sybille Beier
  • Patent number: 5438049
    Abstract: A method for the treatment of inflammation, its signs and symptoms, in a mammal which comprises the administration of an anti-inflammatory effective amount of 16-epiestriol without glycogenic related adverse side-effects.
    Type: Grant
    Filed: August 12, 1993
    Date of Patent: August 1, 1995
    Inventors: Neal S. Latman, Virmal Kishore, Brent C. Bruot, Harold H. Flanders
  • Patent number: 5354745
    Abstract: An estradiol derivative-chlorambucil conjugate of the formula (I): ##STR1## wherein R.sup.1 is alkyl or alkoxyl of 1 to 4 carbon atoms; R.sup.2 is acyl, dansyl, or alkyl; R.sup.3, R.sup.4, and R.sup.5 independently are H, oxo, OH, or acyloxy; m is an integer of 1 to 3; and n is an integer of 0 to 3; provided that when n is 0, all of R.sup.3, R.sup.4, and R.sup.5 are not H at the same time, and at least one of R.sup.3, R.sup.4, and R.sup.5 is a group other than H and OH; and further, when n is 2 or 3, the groups R.sup.1 are the same or different; a process for preparing the same, and a pharmaceutical composition containing the conjugate are described.
    Type: Grant
    Filed: June 3, 1993
    Date of Patent: October 11, 1994
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Fumio Tamura, Tsuyoshi Saito, Satoshi Mitsuhashi, Tadahiro Matsudaira, Kiro Asano
  • Patent number: 5252729
    Abstract: The present invention is directed toward a process for extracting compounds from plant material, comprisinga) contacting hydrolyzed plant material with a supercritical fluid and optionally with a co-solvent and p1 b) recovering the compound from the supercritical fluid.In another embodiment, the present invention is directed toward a process for removing a compound from plant material, comprising contacting the plant material with an acid, a supercritical fluid and a co-solvent, and recovering the compound from the supercritical fluid. The sterols, diosgenin and sarsapogenin, are efficiently extracted from barbasco root and Yucca seed, respectively.
    Type: Grant
    Filed: October 23, 1991
    Date of Patent: October 12, 1993
    Assignee: Schering Corporation
    Inventors: Michelle A. De Crosta, Peter Kabasakalian, Frederick J. F. Honold, Sr.