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WO2002009706A1 - Agoniste d'activite hormonale stimulant un follicule - Google Patents

Agoniste d'activite hormonale stimulant un follicule Download PDF

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Publication number
WO2002009706A1
WO2002009706A1 PCT/US2001/023395 US0123395W WO0209706A1 WO 2002009706 A1 WO2002009706 A1 WO 2002009706A1 US 0123395 W US0123395 W US 0123395W WO 0209706 A1 WO0209706 A1 WO 0209706A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
group
alkyl
mmol
member selected
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2001/023395
Other languages
English (en)
Inventor
Randall A. Scheuerman
Stephen D. Yanofsky
Christopher P. Holmes
Derek Maclean
Beatrice Ruhland
Ronald W. Barrett
Jay E. Wrobel
Wenling Kao
Ariamala Gopalsamy
Fuk-Wah Sum
Baihua Hu
John F. Rogers
James W. Jetter
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SmithKline Beecham Corp
Affymax Researh Institute Inc
Original Assignee
SmithKline Beecham Corp
Affymax Researh Institute Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by SmithKline Beecham Corp, Affymax Researh Institute Inc filed Critical SmithKline Beecham Corp
Priority to EP01955958A priority Critical patent/EP1307193A1/fr
Priority to CA002425889A priority patent/CA2425889A1/fr
Priority to AU2001278006A priority patent/AU2001278006A1/en
Priority to JP2002515259A priority patent/JP2004505051A/ja
Publication of WO2002009706A1 publication Critical patent/WO2002009706A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/14—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • Y 3 is a member selected from the group consisting of O and NR 6 R 7 ;
  • aryl is used herein to refer to an aromatic substituent having a single aromatic ring or multiple aromatic rings which are fused together, linked covalently, or linked to a common group such as a methylene or ethylene moiety.
  • the common linking group may also be a carbonyl as in benzophenone.
  • the aromatic ring(s) may include phenyl, naphthyl, biphenyl, diphenylmethyl and benzophenone among others.
  • contacting is used herein interchangeably with the following: combined with, added to, mixed with, passed over, incubated with, flowed over, etc.
  • the thiazolidinone compounds of present invention can be "administered" to a subject by any conventional method such as, for example, parenteral, oral, topical and inhalation routes as described herein.
  • An amount sufficient” or “an effective amount” is that amount of a given thiazolidinone analog which exhibits the binding/activity of interest or, which provides an improvement in gamete recruitment.
  • EC50 is the effective concentration, i.e., the concentration of a compound at which 50% of the maximal response of that obtained with FSH would be achieved.
  • R > 8 and ⁇ R9 are independently members selected form the group consisting of H, halogen, ketone, alkyl, substituted alkyl, phenyl, substituted phenyl, lower alkoxy, aryloxy, substituted aryloxy, carboxylic acid, carboxylic acid amide, sulfonic acid, sulfonic acid amide, alkynyl, substituted alkynyl and -CONR ⁇ CH ⁇ t Z wherein t is an integer from one to four;
  • the present invention provides a compound wherein, when substituent R 4 , on C-5, is H, and a second substituent at C-5 (R ) is not H, said substituent R on C-5 and substituent R on C-2 are oriented in a cis manner.
  • the compounds of this invention can be incorporated into a variety of formulations for therapeutic administration. More particularly, the compounds of the present invention can be formulated into pharmaceutical compositions by combination with appropriate, pharmaceutically acceptable carriers or diluents, and may be formulated into preparations in solid, semi-solid, liquid or gaseous forms, such as tablets, capsules, pills, powders, granules, dragees, gels, slurries, ointments, solutions, suppositories, injections, inhalants and aerosols. As such, administration of the compounds can be achieved in various ways, including oral, buccal, rectal, parenteral, intraperitoneal, intradermal, transdermal, intracheal, etc., administration.
  • a compound of the present invention is twice as effective in cell culture assay as hMG (i.e., the EC 5 o of that compound is equal to one-half the EC 50 of hMG in the same assay)
  • an initial effective dosage of the compound of the present invention would be one-half the known dosage for hMG.
  • toxicity and therapeutic efficacy of the compounds described herein can be determined by standard pharmaceutical procedures in cell cultures or experimental animals, e.g., by determining the LD 5 o (the dose required to cause death in 50% of the subjects tested) and the ED 5 o (the dose that produces a defined effect in 50% of the subjects tested).
  • Membranes were prepared from Chinese hamster ovary (CHO) cells which expressed FSH-R as described above. These cells specifically bind 125 I-labeled FSH. When a binding assay was performed in the presence of 100 ⁇ M thiazolidinone, no inhibition of the radiolabeled FSH was observed. Thus, although the thiazolidinones are able to bind to the FSH receptor and to elicit a response, they do not block the interaction between FSH and its receptor.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Endocrinology (AREA)
  • Biomedical Technology (AREA)
  • Reproductive Health (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Psychiatry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Diabetes (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Pregnancy & Childbirth (AREA)
  • Urology & Nephrology (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

Selon un premier mode de réalisation, l'invention concerne de nouveaux composés. L'invention concerne également un agoniste de récepteur d'hormone de stimulation de follicule (FSH), dans lequel l'agoniste se lie à un récepteur de FSH possédant un site de liaison de FSH, et dans lequel ledit agoniste n'entre pas en concurrence avec FSH pour le site de liaison de FSH. Selon un second mode de réalisation, l'invention concerne des méthodes d'utilisation desdits composés dans diverses applications pharmaceutiques, par exemple, des thérapies utilisant des agents anti-ischémiques CNS, des agents possédant des propriétés antipsychotiques ou psychoactives, des agents antimicrobiens, et un agent de régulation de la fertilité d'un mammifère.
PCT/US2001/023395 2000-07-27 2001-07-24 Agoniste d'activite hormonale stimulant un follicule Ceased WO2002009706A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP01955958A EP1307193A1 (fr) 2000-07-27 2001-07-24 Agoniste d'activite hormonale stimulant un follicule
CA002425889A CA2425889A1 (fr) 2000-07-27 2001-07-24 Agoniste d'activite hormonale stimulant un follicule
AU2001278006A AU2001278006A1 (en) 2000-07-27 2001-07-24 Agonists of follicle stimulating hormone activity
JP2002515259A JP2004505051A (ja) 2000-07-27 2001-07-24 卵胞刺激ホルモン活性のアゴニスト

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US62924800A 2000-07-27 2000-07-27
US09/629,248 2000-07-27

Publications (1)

Publication Number Publication Date
WO2002009706A1 true WO2002009706A1 (fr) 2002-02-07

Family

ID=24522195

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/023395 Ceased WO2002009706A1 (fr) 2000-07-27 2001-07-24 Agoniste d'activite hormonale stimulant un follicule

Country Status (5)

Country Link
EP (1) EP1307193A1 (fr)
JP (1) JP2004505051A (fr)
AU (1) AU2001278006A1 (fr)
CA (1) CA2425889A1 (fr)
WO (1) WO2002009706A1 (fr)

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004017966A1 (fr) * 2002-08-23 2004-03-04 Ionix Pharmaceuticals Limited Composes heterocycliques a cinq chainons utilises dans le traitement de douleurs chroniques et aigues
WO2005087765A1 (fr) * 2004-03-04 2005-09-22 Arena Pharmaceuticals, Inc. Ligands du recepteur de l'hormone folliculo-stimulante et methodes d'utilisation associees
US7678787B2 (en) 2005-06-09 2010-03-16 Wyeth Pyrrolobenzodiazepine pyridine carboxamides and derivatives as follicle-stimulating hormone receptor antagonists
US7687623B2 (en) 2005-05-12 2010-03-30 Wyeth Llc Pyrrolobenzodiazepines and heterocyclic carboxamide derivatives as follicle stimulating hormone receptor (FSH-R) antagonists
US7691848B2 (en) 2005-03-02 2010-04-06 Wyeth Pyrrolobenzodiazepine arylcarboxamides and derivatives thereof as follicle-stimulating hormone receptor antagonists
US7754722B2 (en) 2002-09-20 2010-07-13 Merck Serono Sa Piperazine derivatives and methods of use
WO2011012600A1 (fr) 2009-07-29 2011-02-03 N.V. Organon Dihydropyrrolo[2,1-a]isoquinoléines condensées à un noyau
WO2011012674A1 (fr) 2009-07-31 2011-02-03 N.V. Organon Dihydrobenzoindazoles
US7994189B2 (en) 2005-05-04 2011-08-09 N.V. Organon Dihydropyridine derivatives
US8017782B2 (en) 2005-05-04 2011-09-13 N.V. Organon 4-phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives as medicaments for the treatment of infertility
US8022218B2 (en) 2005-05-04 2011-09-20 N.V. Organon 4-phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives for the treatment of infertility
US8034945B2 (en) 2005-05-04 2011-10-11 N.V. Organon 4-phenyl-5-OXO-1,4,5,6,7,8-hexahydroquinoline derivatives as medicaments for the treatment of infertility
US8071587B2 (en) 2009-05-27 2011-12-06 N. V. Organon (Dihydro)imidazoiso[5,1-A]quinolines
WO2013006308A2 (fr) 2011-07-01 2013-01-10 Merck Patent Gmbh Dihydropyrazoles
WO2013012848A1 (fr) 2011-07-18 2013-01-24 Merck Patent Gmbh Benzamides
US8394789B2 (en) 2008-02-08 2013-03-12 Msd Oss B.V. (Dihydro)pyrrolo[2,1-α]isoquinolines
US8431564B2 (en) 2009-07-29 2013-04-30 Merck Sharp & Dohme B.V. Ring-annulated dihydropyrrolo[2,1-α]isoquinolines
WO2013106409A1 (fr) 2012-01-10 2013-07-18 Merck Patent Gmbh Dérivés de benzamide en tant que modulateurs de l'hormone de stimulation folliculaire
WO2013117299A1 (fr) 2012-02-08 2013-08-15 Merck Patent Gmbh Analogues de thiazolidinone deutériés utilisés comme agonistes du récepteur de l'hormone folliculo-stimulante
WO2014209978A1 (fr) 2013-06-24 2014-12-31 Merck Patent Gmbh Composés imidazole servant de modulateurs des récepteurs de la fshr et leurs utilisations
WO2015187905A1 (fr) 2014-06-05 2015-12-10 Merck Patent Gmbh Nouveaux dérivés de quinoléine et leur utilisation dans des maladies neurodégénératives
WO2015196759A1 (fr) 2014-06-23 2015-12-30 Tocopherx, Inc. Composés de pyrazole utilisés en tant que modulateurs de fshr et leurs utilisations
WO2016037026A1 (fr) 2014-09-05 2016-03-10 Merck Patent Gmbh Composés diaza et triaza tricycliques à substitution cyclohexyl-éthyle utilisés comme antagonistes de l'indoleamine-2,3-dioxygénase (ido) pour le traitement du cancer
US9546166B2 (en) 2014-07-31 2017-01-17 Merck Patent Gmbh Indolizine derivatives and their use in neurodegenerative diseases
CN107011209A (zh) * 2017-05-11 2017-08-04 蚌埠中实化学技术有限公司 一种3‑甲氧基‑4‑乙氧基苯腈的合成新工艺
US10081637B2 (en) 2013-06-24 2018-09-25 Merck Patent Gmbh Pyrazole compounds as modulators of FSHR and uses thereof
US10323000B2 (en) 2014-12-15 2019-06-18 Merck Patent Gmbh Indole derivatives and their use in neurodegenerative diseases
WO2024184461A2 (fr) 2023-03-08 2024-09-12 Ferring B.V. Modulateurs du récepteur fsh à petites molécules

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008024765A2 (fr) * 2006-08-23 2008-02-28 Allergan, Inc. Thiazolidinones, oxazolidinones thérapeutiques associées, et composés associés

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GB1409898A (en) * 1971-12-06 1975-10-15 Ciba Geigy Ag 1,1-dioxidothiazolidin-4-ones and processes for their manufacture
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WO2000027832A2 (fr) * 1998-11-11 2000-05-18 Glaxo Group Limited Ligands de ppar gamma

Non-Patent Citations (3)

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Title
CHEMICAL ABSTRACTS, vol. 87, no. 9, 29 August 1977, Columbus, Ohio, US; abstract no. 68220Y, PATEL D.R. ET AL.: "Thiazolidinones Part XIV. Synthesis of 2-aryl-3-aryl-5-alkyl /aryl-4-thiazolidiones" page 538; column 2; XP002947081 *
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Cited By (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2396613A (en) * 2002-08-23 2004-06-30 Ionix Pharmaceuticals Ltd Five-membered heterocyclic compounds in the treatment of chronic and acute pain
WO2004017966A1 (fr) * 2002-08-23 2004-03-04 Ionix Pharmaceuticals Limited Composes heterocycliques a cinq chainons utilises dans le traitement de douleurs chroniques et aigues
JP2011088926A (ja) * 2002-09-20 2011-05-06 Merck Serono Sa ピペラジン誘導体及び使用方法
US8946227B2 (en) 2002-09-20 2015-02-03 Merck Serono Sa Piperazine derivatives and methods of use
US7754722B2 (en) 2002-09-20 2010-07-13 Merck Serono Sa Piperazine derivatives and methods of use
WO2005087765A1 (fr) * 2004-03-04 2005-09-22 Arena Pharmaceuticals, Inc. Ligands du recepteur de l'hormone folliculo-stimulante et methodes d'utilisation associees
US7691848B2 (en) 2005-03-02 2010-04-06 Wyeth Pyrrolobenzodiazepine arylcarboxamides and derivatives thereof as follicle-stimulating hormone receptor antagonists
US7994189B2 (en) 2005-05-04 2011-08-09 N.V. Organon Dihydropyridine derivatives
US8034945B2 (en) 2005-05-04 2011-10-11 N.V. Organon 4-phenyl-5-OXO-1,4,5,6,7,8-hexahydroquinoline derivatives as medicaments for the treatment of infertility
US8017782B2 (en) 2005-05-04 2011-09-13 N.V. Organon 4-phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives as medicaments for the treatment of infertility
US8022218B2 (en) 2005-05-04 2011-09-20 N.V. Organon 4-phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives for the treatment of infertility
US7687623B2 (en) 2005-05-12 2010-03-30 Wyeth Llc Pyrrolobenzodiazepines and heterocyclic carboxamide derivatives as follicle stimulating hormone receptor (FSH-R) antagonists
US7678787B2 (en) 2005-06-09 2010-03-16 Wyeth Pyrrolobenzodiazepine pyridine carboxamides and derivatives as follicle-stimulating hormone receptor antagonists
US8394789B2 (en) 2008-02-08 2013-03-12 Msd Oss B.V. (Dihydro)pyrrolo[2,1-α]isoquinolines
US8071587B2 (en) 2009-05-27 2011-12-06 N. V. Organon (Dihydro)imidazoiso[5,1-A]quinolines
US8431564B2 (en) 2009-07-29 2013-04-30 Merck Sharp & Dohme B.V. Ring-annulated dihydropyrrolo[2,1-α]isoquinolines
WO2011012600A1 (fr) 2009-07-29 2011-02-03 N.V. Organon Dihydropyrrolo[2,1-a]isoquinoléines condensées à un noyau
WO2011012674A1 (fr) 2009-07-31 2011-02-03 N.V. Organon Dihydrobenzoindazoles
WO2013006308A2 (fr) 2011-07-01 2013-01-10 Merck Patent Gmbh Dihydropyrazoles
US9517227B2 (en) 2011-07-01 2016-12-13 Merck Patent Gmbh Dihydropyrazoles
WO2013006308A3 (fr) * 2011-07-01 2013-05-10 Merck Patent Gmbh Dihydropyrazoles
US9775830B2 (en) 2011-07-01 2017-10-03 Merck Patent Gmbh Dihydropyrazoles
US8791114B2 (en) 2011-07-01 2014-07-29 Merck Patent Gmbh Dihydropyrazoles
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