RU2232162C2 - Пирролоиндолы, пиридиноиндолы и азепиноиндолы в качестве агонистов 5-нт2с - Google Patents
Пирролоиндолы, пиридиноиндолы и азепиноиндолы в качестве агонистов 5-нт2с Download PDFInfo
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- RU2232162C2 RU2232162C2 RU2001108570/04A RU2001108570A RU2232162C2 RU 2232162 C2 RU2232162 C2 RU 2232162C2 RU 2001108570/04 A RU2001108570/04 A RU 2001108570/04A RU 2001108570 A RU2001108570 A RU 2001108570A RU 2232162 C2 RU2232162 C2 RU 2232162C2
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- Russia
- Prior art keywords
- compound according
- dihydro
- pyrrolo
- carboxaldehyde
- indol
- Prior art date
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- 239000003478 serotonin 5-HT2 receptor agonist Substances 0.000 title abstract 2
- ISZIQZCZKOFSBT-UHFFFAOYSA-N pyrrolo[2,3-g][1]benzazepine Chemical class N1=CC=CC=C2C3=NC=CC3=CC=C21 ISZIQZCZKOFSBT-UHFFFAOYSA-N 0.000 title description 2
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- AYNAVHUTXWVDLR-UHFFFAOYSA-N 1-(6,7-difluoro-2,3-dihydro-1h-pyrrolo[1,2-a]indol-4-yl)propan-2-amine Chemical compound C12=CC(F)=C(F)C=C2C(CC(N)C)=C2N1CCC2 AYNAVHUTXWVDLR-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Landscapes
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- Organic Chemistry (AREA)
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
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| GBGB9819035.8A GB9819035D0 (en) | 1998-09-01 | 1998-09-01 | Chemical compounds VII |
| GB9819035.8 | 1998-09-01 |
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| RU2001108570A RU2001108570A (ru) | 2003-06-20 |
| RU2232162C2 true RU2232162C2 (ru) | 2004-07-10 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2375361C2 (ru) * | 2005-04-08 | 2009-12-10 | Авентис Фарма С.А. | НОВЫЕ ПРОИЗВОДНЫЕ ИЗОИНДОЛОВ, КОМПОЗИЦИИ, СОДЕРЖАЩИЕ ИХ, ИХ ПОЛУЧЕНИЕ И ФАРМАЦЕВТИЧЕСКОЕ ПРИМЕНЕНИЕ, В ЧАСТНОСТИ В КАЧЕСТВЕ ИНГИБИТОРОВ АКТИВНОСТИ БЕЛКА-ШАПЕРОНА Hsp90 |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US6960579B1 (en) | 1998-05-19 | 2005-11-01 | Alcon Manufacturing, Ltd. | Serotonergic 5HT7 receptor compounds for treating ocular and CNS disorders |
| GB9902047D0 (en) * | 1999-01-29 | 1999-03-17 | Cerebrus Ltd | Chemical compounds XI |
| US6465467B1 (en) | 1999-05-21 | 2002-10-15 | Biovitrum Ab | Certain aryl-aliphatic and heteroaryl-aliphatic piperazinyl pyrazines and their use in the treatment of serotonin-related diseases |
| GB9918965D0 (en) * | 1999-08-11 | 1999-10-13 | Cerebrus Ltd | Chemical compounds xxi |
| US6818639B2 (en) | 2000-07-21 | 2004-11-16 | Biovitrum Ab | Pharmaceutical combination formulation and method of treatment with the combination |
| SE0002754D0 (sv) * | 2000-07-21 | 2000-07-21 | Pharmacia & Upjohn Ab | New pharmaceutical combination formulation and method of treatment with the combination |
| SE0004245D0 (sv) | 2000-11-20 | 2000-11-20 | Pharmacia Ab | Novel compounds and their use |
| ATE433962T1 (de) | 2000-11-20 | 2009-07-15 | Biovitrum Ab Publ | Piperazinylpyrazinverbindungen als antagonisten des serotonin-5-ht2-rezeptors |
| WO2002059082A2 (en) | 2000-12-20 | 2002-08-01 | Bristol-Myers Squibb Pharma Company | Aryl and aminoaryl substituted serotonin receptor agonist and antagonist ligands |
| DE60129841T2 (de) * | 2000-12-27 | 2008-04-17 | Vernalis Research Ltd., Winnersh | Indolderivate und deren verwendung als 5-ht2b- und 5-ht2c-rezeptorliganden |
| WO2002098350A2 (en) | 2001-06-01 | 2002-12-12 | Alcon, Inc. | Pyranoindazoles and their use for the treatment of glaucoma |
| JP2004532887A (ja) | 2001-06-01 | 2004-10-28 | アルコン，インコーポレイテッド | 新規な融合インダゾールおよびインドールおよび緑内障治療へのこれらの使用 |
| MXPA03010806A (es) | 2001-06-01 | 2004-11-22 | Alcon Inc | Nuevos analogos de arilaminopropano y su uso para el tratamiento de glaucoma. |
| TW593302B (en) | 2001-12-20 | 2004-06-21 | Alcon Inc | Novel benzodifuranimidazoline and benzofuranimidazoline derivatives and their use for the treatment of glaucoma |
| AU2003243089B2 (en) | 2002-06-19 | 2010-01-07 | Biovitrum Ab (Publ) | Novel compounds, their use and preparation |
| WO2004019874A2 (en) * | 2002-08-30 | 2004-03-11 | Alcon, Inc. | Substituted 5-chroman-5-yl-ethylamine compounds and their use for the treatment of glaucoma |
| EP1581209A4 (en) | 2002-12-13 | 2009-03-11 | Alcon Inc | NEW BENZOPYRAN ANALOGUE AND ITS USE FOR THE TREATMENT OF GLAUKOM |
| CL2004000826A1 (es) | 2003-04-25 | 2005-03-04 | Pfizer | Uso de un agonista para el receptor 5-ht2c para preparar un medicamento util en el tratamiento de la incontinencia urinaria provocada por estres, con la condicion de que el agonista no sea 1-[6-cloro-5-(trifluorometil)-2-piridinil]piperazina (org-129 |
| GB0314967D0 (en) * | 2003-06-26 | 2003-07-30 | Hoffmann La Roche | Piperazine derivatives |
| US7435837B2 (en) * | 2003-10-24 | 2008-10-14 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| US7476687B2 (en) | 2003-11-26 | 2009-01-13 | Alcon, Inc. | Substituted furo[2,3-g]indazoles for the treatment of glaucoma |
| US7129257B1 (en) | 2003-12-15 | 2006-10-31 | Alcon, Inc. | Pyrazolo[3,4- e]benzoxazoles for the treatment of glaucoma |
| US7338972B1 (en) | 2003-12-15 | 2008-03-04 | Alcon, Inc. | Substituted 1-alkylamino-1H-indazoles for the treatment of glaucoma |
| AR046890A1 (es) | 2003-12-15 | 2005-12-28 | Alcon Inc | [1,4] oxazino [2,3-g] indazoles sustituidos para el tratamiento del glaucoma. |
| WO2006022420A1 (ja) | 2004-08-25 | 2006-03-02 | Takeda Pharmaceutical Company Limited | 腹圧性尿失禁の予防・治療剤及びそのスクリーニング方法 |
| CA2585967A1 (en) | 2004-11-01 | 2006-05-11 | Wyeth | Substituted indolizines and derivatives as cns agents |
| US7425572B2 (en) | 2004-12-08 | 2008-09-16 | Alcon, Inc. | Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma |
| NZ560917A (en) | 2005-03-31 | 2011-01-28 | Pfizer Prod Inc | Cyclopentapyridine and tetrahydroquinoline derivatives |
| EP1879875A1 (en) * | 2005-04-22 | 2008-01-23 | Wyeth | Crystal forms opf {[(2r)-7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}amine hydrochloride |
| CN101171252B (zh) * | 2005-05-03 | 2011-06-01 | 霍夫曼-拉罗奇有限公司 | 作为5-ht2配体的四环氮杂吡嗪并二氢吲哚类化合物 |
| JP5528699B2 (ja) | 2006-05-16 | 2014-06-25 | 武田薬品工業株式会社 | 縮合複素環化合物およびその用途 |
| MX2009000508A (es) * | 2006-07-14 | 2009-01-27 | Pfizer Prod Inc | Sal tartrato de (7s)-7-[(5-fluoro-2-metil-bencil)oxi]-2-[(2r)-2-me tilpiperazin-1-il]-6,7-dihidro-5h-ciclopenta[b]piridina. |
| JP5520051B2 (ja) | 2007-11-15 | 2014-06-11 | 武田薬品工業株式会社 | 縮合ピリジン誘導体およびその用途 |
| KR101062376B1 (ko) | 2008-04-10 | 2011-09-06 | 한국화학연구원 | 신규 인돌 카르복실산 비스피리딜 카르복사마이드 유도체,이의 제조방법 및 이를 유효성분으로 함유하는 조성물 |
| EP2510949A4 (en) | 2009-12-11 | 2013-11-13 | Astellas Pharma Inc | THERAPEUTICS FOR FIBROMYALGIA |
| US20130267500A1 (en) | 2010-09-01 | 2013-10-10 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level |
| CN102964352B (zh) * | 2012-11-23 | 2015-04-08 | 华中师范大学 | 具有生物活性的手性2,3-二氢吡咯[1,2-a]吲哚衍生物及其不对称合成方法 |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| EP3733204A4 (en) | 2017-12-27 | 2021-09-15 | Takeda Pharmaceutical Company Limited | THERAPEUTIC AGENT FOR URINARY INCONTINENCE OF STRESS AND FECAL INCONTINENCE |
| WO2020072675A1 (en) | 2018-10-02 | 2020-04-09 | Northwestern University | Beta-carbolines as positive allosteric modulators of the human serotonin receptor 2c (5-ht2c) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3250783A (en) * | 1964-09-21 | 1966-05-10 | American Cyanamid Co | Novel pyrrolo (1, 2-alpha) indoles |
| RU2014332C1 (ru) * | 1989-02-23 | 1994-06-15 | Ф.Хоффман-Ля Рош Аг | Способ получения замещенных пирролов или их фармацевтически приемлемых солей |
| RU2134266C1 (ru) * | 1992-11-02 | 1999-08-10 | Пфайзер Инк. | Производные 5-арилиндола и их применение в качестве агонистов серотонина (5-нт1) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4134894A (en) * | 1978-05-04 | 1979-01-16 | Warner-Lambert Company | Pyrrolo[1,2-a]indole compounds |
| GB8416724D0 (en) * | 1984-06-30 | 1984-08-01 | Sorbio Sa Lab | Active compounds |
| US4778812A (en) * | 1987-06-12 | 1988-10-18 | American Home Products Corporation | 2,3-dihydro-9-methyl-1H-pyrrolo[1,2-a]indol-1-amines and derivatives thereof |
| GB8802127D0 (en) | 1988-02-01 | 1988-03-02 | Glaxo Group Ltd | Chemical compounds |
| SG50693A1 (en) * | 1992-03-12 | 1998-07-20 | Smithkline Beecham Plc | Pharmaceuticals |
| EP0572863A1 (de) * | 1992-06-05 | 1993-12-08 | F. Hoffmann-La Roche Ag | ZNS Pyrazinoindole |
| AU683447B2 (en) * | 1993-03-08 | 1997-11-13 | Fujisawa Pharmaceutical Co., Ltd. | Medicament for treating or preventing cerebrovascular diseases |
| US5629427A (en) * | 1993-08-26 | 1997-05-13 | Peterson; Dwight M. | 2,7-diaminomitosene analogues |
-
1998
- 1998-09-01 GB GBGB9819035.8A patent/GB9819035D0/en not_active Ceased
-
1999
- 1999-09-01 YU YU16001A patent/YU16001A/sh unknown
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- 1999-09-01 EP EP99943091A patent/EP1109813B1/en not_active Expired - Lifetime
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- 1999-09-01 AU AU56375/99A patent/AU758084B2/en not_active Ceased
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- 1999-09-01 PL PL99346427A patent/PL346427A1/xx not_active IP Right Cessation
-
2001
- 2001-02-21 ZA ZA200101457A patent/ZA200101457B/xx unknown
- 2001-02-26 IL IL141659A patent/IL141659A/en not_active IP Right Cessation
- 2001-02-27 NO NO20010991A patent/NO321527B1/no not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3250783A (en) * | 1964-09-21 | 1966-05-10 | American Cyanamid Co | Novel pyrrolo (1, 2-alpha) indoles |
| RU2014332C1 (ru) * | 1989-02-23 | 1994-06-15 | Ф.Хоффман-Ля Рош Аг | Способ получения замещенных пирролов или их фармацевтически приемлемых солей |
| RU2134266C1 (ru) * | 1992-11-02 | 1999-08-10 | Пфайзер Инк. | Производные 5-арилиндола и их применение в качестве агонистов серотонина (5-нт1) |
Non-Patent Citations (1)
| Title |
|---|
| BOS M.j EHK et. al. European journal of Medicinal chemistry. Chimia therapeufica v.32, № 3, с.253-261. BOS et. al. j. Med. chem. 1997, v. 40, с.2762-2769. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2375361C2 (ru) * | 2005-04-08 | 2009-12-10 | Авентис Фарма С.А. | НОВЫЕ ПРОИЗВОДНЫЕ ИЗОИНДОЛОВ, КОМПОЗИЦИИ, СОДЕРЖАЩИЕ ИХ, ИХ ПОЛУЧЕНИЕ И ФАРМАЦЕВТИЧЕСКОЕ ПРИМЕНЕНИЕ, В ЧАСТНОСТИ В КАЧЕСТВЕ ИНГИБИТОРОВ АКТИВНОСТИ БЕЛКА-ШАПЕРОНА Hsp90 |
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