CA2425889A1 - Agoniste d'activite hormonale stimulant un follicule - Google Patents
Agoniste d'activite hormonale stimulant un follicule Download PDFInfo
- Publication number
- CA2425889A1 CA2425889A1 CA002425889A CA2425889A CA2425889A1 CA 2425889 A1 CA2425889 A1 CA 2425889A1 CA 002425889 A CA002425889 A CA 002425889A CA 2425889 A CA2425889 A CA 2425889A CA 2425889 A1 CA2425889 A1 CA 2425889A1
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- substituted
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- alkyl
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- 239000000556 agonist Substances 0.000 title claims abstract description 23
- 108010079345 Follicle Stimulating Hormone Proteins 0.000 title description 61
- 102000012673 Follicle Stimulating Hormone Human genes 0.000 title description 61
- 229940028334 follicle stimulating hormone Drugs 0.000 title description 61
- 230000003054 hormonal effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 213
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- 102000008175 FSH Receptors Human genes 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 41
- 239000000018 receptor agonist Substances 0.000 claims abstract description 13
- 229940044601 receptor agonist Drugs 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 150
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 125000000623 heterocyclic group Chemical group 0.000 claims description 62
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 40
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- 229910052717 sulfur Inorganic materials 0.000 claims description 33
- 230000000694 effects Effects 0.000 claims description 30
- 125000003107 substituted aryl group Chemical group 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 25
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 22
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- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 135
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 122
- 239000000243 solution Substances 0.000 description 105
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- 239000000047 product Substances 0.000 description 43
- -1 small molecule organic compounds Chemical class 0.000 description 42
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 39
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 38
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 34
- 238000004128 high performance liquid chromatography Methods 0.000 description 33
- 238000003756 stirring Methods 0.000 description 32
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- 238000002347 injection Methods 0.000 description 18
- 238000002953 preparative HPLC Methods 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 229910052736 halogen Inorganic materials 0.000 description 15
- 150000002367 halogens Chemical class 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- 238000010828 elution Methods 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- NJVDYCNYTDOXPX-UHFFFAOYSA-N 2-(3-ethoxy-4-methoxyphenyl)ethanamine Chemical compound CCOC1=CC(CCN)=CC=C1OC NJVDYCNYTDOXPX-UHFFFAOYSA-N 0.000 description 13
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 12
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
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Classifications
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Reproductive Health (AREA)
- Neurology (AREA)
- Endocrinology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Communicable Diseases (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (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.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62924800A | 2000-07-27 | 2000-07-27 | |
| US09/629,248 | 2000-07-27 | ||
| PCT/US2001/023395 WO2002009706A1 (fr) | 2000-07-27 | 2001-07-24 | Agoniste d'activite hormonale stimulant un follicule |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2425889A1 true CA2425889A1 (fr) | 2002-02-07 |
Family
ID=24522195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002425889A Abandoned CA2425889A1 (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) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003255844A1 (en) * | 2002-08-23 | 2004-03-11 | Ionix Pharmaceuticals Limited | Five-membered heterocyclic compounds in the treatment of chronic and acute pain |
| ES2399047T3 (es) * | 2002-09-20 | 2013-03-25 | Merck Serono Sa | Derivados de piperazina y procedimiento de uso |
| US20080004263A1 (en) * | 2004-03-04 | 2008-01-03 | Santora Vincent J | Ligands of Follicle Stimulating Hormone Receptor and Methods of Use Thereof |
| US7691848B2 (en) | 2005-03-02 | 2010-04-06 | Wyeth | Pyrrolobenzodiazepine arylcarboxamides and derivatives thereof as follicle-stimulating hormone receptor antagonists |
| UA92009C2 (ru) | 2005-05-04 | 2010-09-27 | Н.В. Органон | Производные 4-фенил-5-оксо-1,4,5,6,7,8-гексагидрохинолина для лечения бесплодия |
| UA92007C2 (ru) | 2005-05-04 | 2010-09-27 | Н.В. Органон | Производные 4-фенил-5-оксо-1,4,5,6,7,8-гексагидрохинолина для лечения бесплодности |
| UA92008C2 (en) | 2005-05-04 | 2010-09-27 | Н.В. Органон | 4-PHENYL-5-OXO-l,4,5,6,7,8-HEXAHYDROQUINOLINE DERIVATIVES AS MEDICAMENTS FOR THE TREATMENT OF INFERTILITY |
| DK1879866T3 (da) | 2005-05-04 | 2011-06-06 | Organon Nv | Dihydropyridinderivater |
| MX2007014085A (es) | 2005-05-12 | 2008-02-07 | Wyeth Corp | Pirrolobenzodiazepinas y derivados de carboxamida heterociclica como antagonistas de receptor de hormona estimulante del foliculo. |
| WO2006135687A1 (fr) | 2005-06-09 | 2006-12-21 | Wyeth | Pyrrolobenzodiazepine pyridine carboxamides et derives utilises comme antagonistes du recepteur de l'hormone de stimulation folliculaire |
| JP5474548B2 (ja) * | 2006-08-23 | 2014-04-16 | アラーガン インコーポレイテッド | 治療用の置換チアゾリジノン類、オキサゾリジノン類および関連化合物 |
| TW200944523A (en) | 2008-02-08 | 2009-11-01 | Organon Nv | (Dihydro)pyrrolo[2,1-a]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 |
| TW201116531A (en) | 2009-07-29 | 2011-05-16 | Organon Nv | Ring-annulated dihydropyrrolo[2,1-a]isoquinolines |
| TW201116515A (en) | 2009-07-31 | 2011-05-16 | Organon Nv | Dihydrobenzoindazoles |
| CA2837524C (fr) | 2011-07-01 | 2019-08-20 | Merck Patent Gmbh | Dihydropyrazoles |
| JP6162694B2 (ja) | 2011-07-18 | 2017-07-12 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | ベンズアミド類 |
| CN104080784B (zh) * | 2012-01-10 | 2017-07-18 | 默克专利有限公司 | 用作卵泡刺激素调节剂的苯甲酰胺衍生物 |
| CN104114544A (zh) * | 2012-02-08 | 2014-10-22 | 默克专利有限公司 | 用作卵泡刺激素受体激动剂的氘化噻唑烷酮类似物 |
| JP6625973B2 (ja) | 2013-06-24 | 2019-12-25 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | Fshrの調節剤としてのピラゾール化合物及びその使用 |
| EP3013823B1 (fr) | 2013-06-24 | 2017-11-01 | Merck Patent GmbH | Composés imidazole servant de modulateurs des récepteurs de la fshr et leurs utilisations |
| AU2015269598B2 (en) | 2014-06-05 | 2019-11-14 | Merck Patent Gmbh | Novel quinoline derivatives and their use in neurodegenerative diseases |
| WO2015196335A1 (fr) | 2014-06-23 | 2015-12-30 | Tocopherx, Inc. | Composés de pyrazole utilisés comme modulateurs de fshr et leurs utilisations |
| JP6571756B2 (ja) | 2014-07-31 | 2019-09-04 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 神経変性疾患に適応可能なインドリジン誘導体 |
| AU2015311826B2 (en) | 2014-09-05 | 2019-05-23 | Merck Patent Gmbh | Cyclohexyl-ethyl substituted diaza- and triaza-tricyclic compounds as indole-amine-2,3-dioxygenase (IDO) antagonists for the treatment of cancer |
| EP3233841A1 (fr) | 2014-12-15 | 2017-10-25 | Merck Patent GmbH | Dérivés indoliques et azaindoliques et leur utilisation dans le traitement de maladies neurodégénératives |
| 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 |
| WO2024184461A2 (fr) | 2023-03-08 | 2024-09-12 | Ferring B.V. | Modulateurs du récepteur fsh à petites molécules |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3328415A (en) * | 1961-06-29 | 1967-06-27 | Sterling Drug Inc | 5-(2-hydroxyethyl)-4-thiazolidones and derivatives thereof |
| CH548411A (de) * | 1971-12-06 | 1974-04-30 | Ciba Geigy Ag | Verfahren zur herstellung von neuen 1,1-dioxothiazolidin4-onen. |
| US5061720A (en) * | 1989-09-13 | 1991-10-29 | A. H. Robins Company, Inc. | Substituted-4-thiazolidinone derivatives |
| GB9824614D0 (en) * | 1998-11-11 | 1999-01-06 | Glaxo Group Ltd | Chemical compounds |
-
2001
- 2001-07-24 CA CA002425889A patent/CA2425889A1/fr not_active Abandoned
- 2001-07-24 AU AU2001278006A patent/AU2001278006A1/en not_active Abandoned
- 2001-07-24 EP EP01955958A patent/EP1307193A1/fr not_active Withdrawn
- 2001-07-24 WO PCT/US2001/023395 patent/WO2002009706A1/fr not_active Ceased
- 2001-07-24 JP JP2002515259A patent/JP2004505051A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1307193A1 (fr) | 2003-05-07 |
| AU2001278006A1 (en) | 2002-02-13 |
| JP2004505051A (ja) | 2004-02-19 |
| WO2002009706A1 (fr) | 2002-02-07 |
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