CA2410091A1 - Piperidyindoles comme ligands du recepteur de la serotonine - Google Patents
Piperidyindoles comme ligands du recepteur de la serotonine Download PDFInfo
- Publication number
- CA2410091A1 CA2410091A1 CA002410091A CA2410091A CA2410091A1 CA 2410091 A1 CA2410091 A1 CA 2410091A1 CA 002410091 A CA002410091 A CA 002410091A CA 2410091 A CA2410091 A CA 2410091A CA 2410091 A1 CA2410091 A1 CA 2410091A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- hydrogen
- formula
- fluoro
- dihydro
- 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.)
- Abandoned
Links
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 title description 4
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 title description 4
- 239000003446 ligand Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- 239000001257 hydrogen Substances 0.000 claims abstract description 35
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 29
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- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
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- 238000002360 preparation method Methods 0.000 claims description 4
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000003772 serotonin uptake inhibitor Substances 0.000 claims description 3
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- 239000005720 sucrose Substances 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- JYNFUBKIYXPKOW-KWSDIJCZSA-N tert-butyl (2S,4R)-4-(6-fluoro-1H-indol-3-yl)-2-methylpiperidine-1-carboxylate 6-fluoro-3-[(2R,4S)-2-methylpiperidin-4-yl]-1H-indole Chemical compound FC1=CC=C2C(=CNC2=C1)[C@H]1C[C@@H](N(CC1)C(=O)OC(C)(C)C)C.FC1=CC=C2C(=CNC2=C1)[C@@H]1C[C@H](NCC1)C JYNFUBKIYXPKOW-KWSDIJCZSA-N 0.000 description 1
- PVZMHIFOIJRJFT-NEPJUHHUSA-N tert-butyl (2r,4s)-4-(6,7-difluoro-1h-indol-3-yl)-2-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)[C@H](C)C[C@H]1C1=CNC2=C(F)C(F)=CC=C12 PVZMHIFOIJRJFT-NEPJUHHUSA-N 0.000 description 1
- YTIQCZRAPLRSBD-OLZOCXBDSA-N tert-butyl (2r,4s)-4-(6-fluoro-1h-indol-3-yl)-2-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)[C@H](C)C[C@H]1C1=CNC2=CC(F)=CC=C12 YTIQCZRAPLRSBD-OLZOCXBDSA-N 0.000 description 1
- MPGINHJVRZRXLT-OCCSQVGLSA-N tert-butyl (2r,4s)-4-(6-fluoro-7-methyl-1h-indol-3-yl)-2-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)[C@H](C)C[C@H]1C1=CNC2=C(C)C(F)=CC=C12 MPGINHJVRZRXLT-OCCSQVGLSA-N 0.000 description 1
- YTIQCZRAPLRSBD-QWHCGFSZSA-N tert-butyl (2s,4r)-4-(6-fluoro-1h-indol-3-yl)-2-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)[C@@H](C)C[C@@H]1C1=CNC2=CC(F)=CC=C12 YTIQCZRAPLRSBD-QWHCGFSZSA-N 0.000 description 1
- MPGINHJVRZRXLT-GXTWGEPZSA-N tert-butyl (2s,4r)-4-(6-fluoro-7-methyl-1h-indol-3-yl)-2-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)[C@@H](C)C[C@@H]1C1=CNC2=C(C)C(F)=CC=C12 MPGINHJVRZRXLT-GXTWGEPZSA-N 0.000 description 1
- QQTGGWRADFEJGW-UHFFFAOYSA-N tert-butyl 4-(6,7-difluoro-1h-indol-3-yl)-2-methyl-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)C(C)CC(C=2C3=CC=C(F)C(F)=C3NC=2)=C1 QQTGGWRADFEJGW-UHFFFAOYSA-N 0.000 description 1
- JEORCJYLBWCGIH-UHFFFAOYSA-N tert-butyl 4-(6,7-difluoro-1h-indol-3-yl)-6-methyl-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)C(C)C=C1C1=CNC2=C(F)C(F)=CC=C12 JEORCJYLBWCGIH-UHFFFAOYSA-N 0.000 description 1
- SHVSMVJGYZMRJR-UHFFFAOYSA-N tert-butyl 4-(6-fluoro-1h-indol-3-yl)-2-methyl-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)C(C)CC(C=2C3=CC=C(F)C=C3NC=2)=C1 SHVSMVJGYZMRJR-UHFFFAOYSA-N 0.000 description 1
- YTIQCZRAPLRSBD-UHFFFAOYSA-N tert-butyl 4-(6-fluoro-1h-indol-3-yl)-2-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)C(C)CC1C1=CNC2=CC(F)=CC=C12 YTIQCZRAPLRSBD-UHFFFAOYSA-N 0.000 description 1
- ZFORAKSVUAMSCE-UHFFFAOYSA-N tert-butyl 4-(6-fluoro-7-methyl-1h-indol-3-yl)-2-methyl-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)C(C)CC(C=2C3=CC=C(F)C(C)=C3NC=2)=C1 ZFORAKSVUAMSCE-UHFFFAOYSA-N 0.000 description 1
- KDHPXBGCZHUCBV-UHFFFAOYSA-N tert-butyl 4-(6-fluoro-7-methyl-1h-indol-3-yl)-6-methyl-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)C(C)C=C1C1=CNC2=C(C)C(F)=CC=C12 KDHPXBGCZHUCBV-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Otolaryngology (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
L'invention concerne un composé pharmaceutique représenté par la formule (I) dans laquelle R?1¿ et R?2¿ représentent chacun hydrogène ou alkyle C¿1-6?, R?3¿ représente SR?10¿, -SOR?10¿, -SO¿2?R?10¿, -COR?10¿, -CH¿2?OH ou -CONHR?11¿, où R?10¿ représente alkyle C¿1-6? et R?11¿ représente hydrogène ou alkyle C¿1-6?, R?4¿, R?5¿, R?6¿ et R?7¿ représentent chacun hydrogène ou alkyle C¿1-6?, à la condition qu'au moins un parmi R?4¿, R?5¿, R?6¿ et R?7¿ représente alkyle C¿1-6?, R?8¿ et R?9¿ représentent chacun hydrogène, halo, alkyle C¿1-6? ou cyano, n vaut 0 ou 1 et m vaut 2 ou 3,x est (a) ou (b), et y est (c) (d), où R?12¿ et R?13¿ représentent chacun hydrogène, alkyle C1-6, cyclopropyle ou cyclopropyle-alkyle C¿1-6?. L'invention concerne également des sels de ce composé.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0012082.4 | 2000-05-18 | ||
| GB0012082A GB2362381A (en) | 2000-05-18 | 2000-05-18 | Pharmaceutically active indolyl-piperidines |
| PCT/US2001/011744 WO2001087881A1 (fr) | 2000-05-18 | 2001-05-04 | Piperidyindoles comme ligands du recepteur de la serotonine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2410091A1 true CA2410091A1 (fr) | 2001-11-22 |
Family
ID=9891893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002410091A Abandoned CA2410091A1 (fr) | 2000-05-18 | 2001-05-04 | Piperidyindoles comme ligands du recepteur de la serotonine |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1286992A1 (fr) |
| JP (1) | JP2003533523A (fr) |
| AU (1) | AU2001259051A1 (fr) |
| CA (1) | CA2410091A1 (fr) |
| GB (1) | GB2362381A (fr) |
| WO (1) | WO2001087881A1 (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR028685A1 (es) * | 2000-06-14 | 2003-05-21 | Lundbeck & Co As H | Derivados de indol |
| EP1468996B1 (fr) * | 2000-06-14 | 2007-09-26 | H. Lundbeck A/S | Derivés d'indole pour le traitement des maladies du système nerveux central |
| TWI391387B (zh) * | 2004-05-12 | 2013-04-01 | Eisai R&D Man Co Ltd | 具有哌啶環之吲哚衍生物 |
| KR20080007649A (ko) * | 2005-05-11 | 2008-01-22 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 피페리딘환을 가지는 인돌 유도체의 결정 및 그의 제조방법 |
| EP1880995B1 (fr) | 2005-05-11 | 2011-12-21 | Eisai R&D Management Co., Ltd. | Méthode de synthèse d un dérivé d'indole comportant un cycle pipéridine |
| CN101171249B (zh) * | 2005-05-11 | 2010-11-10 | 卫材R&D管理有限公司 | 制备具有哌啶环的吲哚衍生物的方法 |
| CL2007003591A1 (es) * | 2006-12-12 | 2008-02-29 | Wyeth Corp | Compuestos derivados de sulfonamida ciclicos, inhibidores de retoma de monoamina; procedimiento de preparacion; composicion farmaceutica; y uso para el tratamiento o prevencion de disfuncion sexual, trastorno gastrointestinal, trastorno genitourinari |
| WO2008073958A2 (fr) | 2006-12-12 | 2008-06-19 | Wyeth | Dérivés de benzothiadiazinedioxyde substitués et procédés d'utilisation de ceux-ci |
| CN101250154B (zh) * | 2008-03-13 | 2011-05-04 | 台州市知青化工有限公司 | 一种工业化生产6-氟吲哚的方法 |
| NZ748306A (en) * | 2016-07-04 | 2020-07-31 | Bayer Cropscience Ag | Benzosultams and analogues and their use as fungicides |
| CN112457235B (zh) * | 2020-12-02 | 2023-04-25 | 烟台凯博医药科技有限公司 | 一种7-甲基吲哚的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4335127A (en) * | 1979-01-08 | 1982-06-15 | Janssen Pharmaceutica, N.V. | Piperidinylalkyl quinazoline compounds, composition and method of use |
| FR2621588B1 (fr) * | 1987-10-08 | 1991-05-24 | Roussel Uclaf | Nouveaux derives de la 1,1-dioxo 1,2-benzoisothiazol 3-one, leur procede de preparation et leur application comme medicaments |
| IL90858A (en) * | 1988-07-07 | 1994-08-26 | Rhone Poulenc Sante | Derivatives of (AZA) naphthalensultam, their preparation and compositions containing them |
| EP0536419B1 (fr) * | 1991-04-23 | 1999-10-13 | Toray Industries, Inc. | Derives de triazole tricyclique, production et utilisation de ces derives |
| FR2675801A1 (fr) * | 1991-04-24 | 1992-10-30 | Rhone Poulenc Rorer Sa | Piperidines, leur preparation et les medicaments les contenant. |
| DE19500689A1 (de) * | 1995-01-12 | 1996-07-18 | Merck Patent Gmbh | Indolpiperidin-Derivate |
| WO1999010346A1 (fr) * | 1997-08-22 | 1999-03-04 | Eli Lilly And Company Limited | Derives de benzothiadiazinyl-indole et leur utilisation comme ligands recepteurs de la serotonine |
| GB9810886D0 (en) * | 1998-05-13 | 1998-07-22 | Lilly Industries Ltd | Pharmaceutical compounds |
| GB9825413D0 (en) * | 1998-11-19 | 1999-01-13 | Lilly Co Eli | Pharmaceutical compounds |
| GB9903784D0 (en) * | 1999-02-18 | 1999-04-14 | Lilly Co Eli | Pharmaceutical compounds |
| EP1106605A4 (fr) * | 1999-06-24 | 2005-12-07 | Toray Industries | Antagonistes du recepteur adrenergique-alpha1b |
-
2000
- 2000-05-18 GB GB0012082A patent/GB2362381A/en not_active Withdrawn
-
2001
- 2001-05-04 AU AU2001259051A patent/AU2001259051A1/en not_active Abandoned
- 2001-05-04 WO PCT/US2001/011744 patent/WO2001087881A1/fr not_active Ceased
- 2001-05-04 CA CA002410091A patent/CA2410091A1/fr not_active Abandoned
- 2001-05-04 JP JP2001584275A patent/JP2003533523A/ja not_active Withdrawn
- 2001-05-04 EP EP01932534A patent/EP1286992A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB0012082D0 (en) | 2000-07-12 |
| EP1286992A1 (fr) | 2003-03-05 |
| WO2001087881A1 (fr) | 2001-11-22 |
| AU2001259051A1 (en) | 2001-11-26 |
| JP2003533523A (ja) | 2003-11-11 |
| GB2362381A (en) | 2001-11-21 |
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