TWI377195B - Tricyclic indeno-pyrrole derivatives as serotonin receptor modulators - Google Patents
Tricyclic indeno-pyrrole derivatives as serotonin receptor modulators Download PDFInfo
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- TWI377195B TWI377195B TW094125988A TW94125988A TWI377195B TW I377195 B TWI377195 B TW I377195B TW 094125988 A TW094125988 A TW 094125988A TW 94125988 A TW94125988 A TW 94125988A TW I377195 B TWI377195 B TW I377195B
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- Prior art keywords
- etoac
- methyl
- mmol
- pyrrole
- found
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- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 title description 4
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 title description 4
- CNAFOLPGHNAMBW-UHFFFAOYSA-N indeno[2,1-b]pyrrole Chemical class C1=CC=CC2=CC3=NC=CC3=C21 CNAFOLPGHNAMBW-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 257
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 228
- -1 (d) Chemical group 0.000 claims description 63
- 239000007789 gas Substances 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 28
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
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- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
-
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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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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- A—HUMAN NECESSITIES
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
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- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Neurosurgery (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Addiction (AREA)
- Anesthesiology (AREA)
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| US59204704P | 2004-07-29 | 2004-07-29 |
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| TW200619196A TW200619196A (en) | 2006-06-16 |
| TWI377195B true TWI377195B (en) | 2012-11-21 |
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| TW094125988A TWI377195B (en) | 2004-07-29 | 2005-07-29 | Tricyclic indeno-pyrrole derivatives as serotonin receptor modulators |
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| EP (1) | EP1841738A4 (enExample) |
| JP (1) | JP4990164B2 (enExample) |
| KR (2) | KR20130047765A (enExample) |
| CN (1) | CN101516372A (enExample) |
| AR (1) | AR050274A1 (enExample) |
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| BR (1) | BRPI0512869A (enExample) |
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| NO (1) | NO20071102L (enExample) |
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| TW (1) | TWI377195B (enExample) |
| WO (1) | WO2007081299A2 (enExample) |
| ZA (1) | ZA200700684B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| AU2005333518B2 (en) * | 2004-07-29 | 2010-12-02 | Athersys, Inc. | Tricyclic indeno-pyrrole derivatives as serotonin receptor modulators |
| 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 |
| EP1988091B1 (en) | 2007-02-07 | 2015-06-10 | Kyowa Hakko Kirin Co., Ltd. | Tricyclic compounds |
| 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 |
| EP2242745A1 (de) * | 2008-02-07 | 2010-10-27 | Sanofi-Aventis | Neue phenyl-substituierte imidazolidine, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP3081213B1 (en) | 2008-08-06 | 2020-04-01 | Kyowa Kirin Co., Ltd. | Tricyclic compound |
| TW201041851A (en) | 2009-03-10 | 2010-12-01 | Organon Nv | Tricyclic heterocyclic derivatives |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| CN106380440B (zh) * | 2016-08-30 | 2019-02-01 | 华东师范大学 | 一种茚酮并吡咯类衍生物及其合成方法和应用 |
| CN106631989B (zh) * | 2016-11-26 | 2019-07-16 | 威海迪素制药有限公司 | 一种盐酸多奈哌齐有关物质e的制备方法 |
| EP3733204A4 (en) | 2017-12-27 | 2021-09-15 | Takeda Pharmaceutical Company Limited | THERAPEUTIC AGENT FOR URINARY INCONTINENCE OF STRESS AND FECAL INCONTINENCE |
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| EP0170093B1 (en) * | 1984-07-25 | 1990-03-07 | Abbott Laboratories | 1,2,3,3a,8,8a-hexahydro-indeno-(1,2-c)pyrrdes |
| US4622405A (en) * | 1984-07-25 | 1986-11-11 | Abbott Laboratories | 1,2,3,3a,8,8a-hexahydro-indeno[1,2-c]pyrroles useful in the treatment of hypertension |
| JPH03502701A (ja) * | 1988-12-15 | 1991-06-20 | アボツト・ラボラトリーズ | ５‐ｈｔ選択性物質 |
| US5049564A (en) * | 1989-11-17 | 1991-09-17 | Abbott Laboratories | 5-HT selective agents |
| US5244888A (en) | 1989-11-17 | 1993-09-14 | Abbott Laboratories | 5-HT selective agents |
| TW334423B (en) * | 1993-10-22 | 1998-06-21 | Hoffmann La Roche | Tricyclic 1-aminoethylpyrrole-derivatives |
| US7351711B2 (en) * | 2003-07-31 | 2008-04-01 | Janssen Pharmaceutical, N.V. | Tricyclic indanyls as integrin inhibitors |
| TWI350168B (en) * | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| AU2005333518B2 (en) * | 2004-07-29 | 2010-12-02 | Athersys, Inc. | Tricyclic indeno-pyrrole derivatives as serotonin receptor modulators |
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2005
- 2005-07-26 AU AU2005333518A patent/AU2005333518B2/en not_active Ceased
- 2005-07-26 BR BRPI0512869-2A patent/BRPI0512869A/pt not_active Application Discontinuation
- 2005-07-26 RU RU2007107494/04A patent/RU2007107494A/ru not_active Application Discontinuation
- 2005-07-26 KR KR1020137007788A patent/KR20130047765A/ko not_active Withdrawn
- 2005-07-26 WO PCT/US2005/026415 patent/WO2007081299A2/en not_active Ceased
- 2005-07-26 EP EP05858534A patent/EP1841738A4/en not_active Withdrawn
- 2005-07-26 CA CA2603249A patent/CA2603249C/en not_active Expired - Fee Related
- 2005-07-26 JP JP2007554065A patent/JP4990164B2/ja not_active Expired - Fee Related
- 2005-07-26 KR KR1020077002230A patent/KR101257233B1/ko not_active Expired - Fee Related
- 2005-07-26 US US11/189,952 patent/US20060025601A1/en not_active Abandoned
- 2005-07-26 CN CNA2005800255071A patent/CN101516372A/zh active Pending
- 2005-07-26 NZ NZ552806A patent/NZ552806A/en not_active IP Right Cessation
- 2005-07-28 AR ARP050103146A patent/AR050274A1/es not_active Application Discontinuation
- 2005-07-29 TW TW094125988A patent/TWI377195B/zh not_active IP Right Cessation
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2007
- 2007-01-24 ZA ZA200700684A patent/ZA200700684B/xx unknown
- 2007-01-25 IL IL180977A patent/IL180977A/en not_active IP Right Cessation
- 2007-02-27 NO NO20071102A patent/NO20071102L/no not_active Application Discontinuation
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2009
- 2009-06-04 US US12/478,362 patent/US7935830B2/en not_active Expired - Fee Related
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2011
- 2011-03-25 US US13/071,732 patent/US8232311B2/en not_active Expired - Fee Related
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2012
- 2012-06-18 US US13/526,249 patent/US8716324B2/en not_active Expired - Fee Related
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2014
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