JP5022494B2 - アルツハイマー病治療用のα７ニコチン性アセチルコリン受容体リガンドとしてのキヌクリジン−４−イルメチル１Ｈ−インドール−３−カルボキシレート誘導体 - Google Patents
アルツハイマー病治療用のα７ニコチン性アセチルコリン受容体リガンドとしてのキヌクリジン−４−イルメチル１Ｈ−インドール−３−カルボキシレート誘導体 Download PDFInfo
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- JP5022494B2 JP5022494B2 JP2010527249A JP2010527249A JP5022494B2 JP 5022494 B2 JP5022494 B2 JP 5022494B2 JP 2010527249 A JP2010527249 A JP 2010527249A JP 2010527249 A JP2010527249 A JP 2010527249A JP 5022494 B2 JP5022494 B2 JP 5022494B2
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- Prior art keywords
- indole
- ylmethyl
- carboxylate
- quinuclidin
- alkyl
- Prior art date
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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| US20130197028A1 (en) * | 2010-06-25 | 2013-08-01 | Oklahoma Medical Research Foundation | nAChRalpha7 Agonists and nAChRalpha7 Antagonists for Treating Ulcerative Colitis (UC) and Crohn's Disease (CD) |
| CN103747681A (zh) * | 2011-07-01 | 2014-04-23 | 英维沃医药有限公司 | 有限认知损害的治疗方法 |
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| RU2635522C2 (ru) | 2012-05-08 | 2017-11-13 | Форум Фармасьютикалз, Инк. | Способы поддержания, лечения или улучшения когнитивной функции |
| JP6261048B2 (ja) * | 2012-12-05 | 2018-01-17 | 国立大学法人 新潟大学 | 破骨細胞が関与する疾患の予防又は治療剤 |
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Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1223873A (en) * | 1982-04-14 | 1987-07-07 | Francis D. King | Pharmaceutically active compounds |
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| US4910193A (en) | 1985-12-16 | 1990-03-20 | Sandoz Ltd. | Treatment of gastrointestinal disorders |
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| WO1989000158A1 (en) | 1987-07-02 | 1989-01-12 | Pfizer Inc. | Bridged-diazabicycloalkyl quinolone carboxylic acids and esters |
| US4950759A (en) | 1988-07-07 | 1990-08-21 | Duphar International Research B.V. | Substituted 1,7-annelated 1H-indazoles |
| IT1228293B (it) | 1989-02-06 | 1991-06-07 | Angeli Inst Spa | Benzoderivati di composti eterociclici contenenti azoto. |
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| US5190953A (en) * | 1992-03-26 | 1993-03-02 | A. H. Robins Company, Incorporated | Heterocyclic carboxylic acid amides and esters of azabicyclic compounds as gastric prokinetic, antiemetic, anxiolytic and antiarrhythmic agents |
| US5300512A (en) | 1992-06-24 | 1994-04-05 | G. D. Searle & Co. | Benzimidazole compounds |
| IL107184A (en) | 1992-10-09 | 1997-08-14 | Abbott Lab | Heterocyclic ether compounds that enhance cognitive function |
| US5852041A (en) | 1993-04-07 | 1998-12-22 | Sibia Neurosciences, Inc. | Substituted pyridines useful as modulators of acethylcholine receptors |
| JP3235913B2 (ja) | 1993-07-30 | 2001-12-04 | エーザイ株式会社 | アミノ安息香酸誘導体 |
| US5399562A (en) | 1994-02-04 | 1995-03-21 | G. D. Searle & Co. | Indolones useful as serotonergic agents |
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| US5585388A (en) | 1995-04-07 | 1996-12-17 | Sibia Neurosciences, Inc. | Substituted pyridines useful as modulators of acetylcholine receptors |
| US5583140A (en) | 1995-05-17 | 1996-12-10 | Bencherif; Merouane | Pharmaceutical compositions for the treatment of central nervous system disorders |
| IL118279A (en) | 1995-06-07 | 2006-10-05 | Abbott Lab | Compounds 3 - Pyridyloxy (or Thio) Alkyl Heterocyclic Pharmaceutical Compositions Containing Them and Their Uses for Preparing Drugs to Control Synaptic Chemical Transmission |
| US5712270A (en) | 1995-11-06 | 1998-01-27 | American Home Products Corporation | 2-arylamidothiazole derivatives with CNS activity |
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| AR013184A1 (es) | 1997-07-18 | 2000-12-13 | Astrazeneca Ab | Aminas heterociclicas espiroazobiciclicas, composicion farmaceutica, uso de dichas aminas para preparar medicamentos y metodo de tratamiento o profilaxis |
| SK285198B6 (sk) | 1997-10-27 | 2006-08-03 | Neurosearch A/S | Homopiperazínový derivát, farmaceutická kompozícia obsahujúca tento derivát a jeho použitie |
| PT1083889E (pt) | 1998-06-01 | 2004-04-30 | Ortho Mcneil Pharm Inc | Compostos de tetra-hidronaftaleno e sua utilizacao no tratamento de doencas neurodegenerativas |
| SE9904176D0 (sv) | 1999-11-18 | 1999-11-18 | Astra Ab | New use |
| AU2001266100B9 (en) | 2000-06-27 | 2005-10-06 | Laboratorios S.A.L.V.A.T., S.A. | Carbamates derived from arylalkylamines |
| US6486172B2 (en) | 2000-08-18 | 2002-11-26 | Pharmacia & Upjohn Company | Quinuclidine-substituted aryl compounds for treatment of disease |
| US6492386B2 (en) | 2000-08-18 | 2002-12-10 | Pharmacia & Upjohn Company | Quinuclidine-substituted aryl compounds for treatment of disease |
| US6479510B2 (en) | 2000-08-18 | 2002-11-12 | Pharmacia & Upjohn Company | Quinuclidine-substituted aryl compounds for treatment of disease |
| WO2002017358A2 (en) | 2000-08-21 | 2002-02-28 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease (nicotinic acetylcholine receptor antagonists) |
| WO2002015662A2 (en) | 2000-08-21 | 2002-02-28 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease (nicotinic acetylcholine receptor antagonists |
| JP2004506734A (ja) | 2000-08-21 | 2004-03-04 | ファルマシア・アンド・アップジョン・カンパニー | 疾患治療用のキヌクリド置換ヘテロアリール部分 |
| PL362989A1 (en) | 2000-12-22 | 2004-11-15 | Almirall Prodesfarma Ag | Quinuclidine carbamate derivatives and their use as m3 antagonists |
| EE05516B1 (et) * | 2002-09-25 | 2012-02-15 | Memory@Pharmaceuticals@Corporation | Indasoolid bensotiasoolid ja bensoisotiasoolid nende valmistamine ning kasutamine |
| EP1742944B1 (en) | 2004-04-22 | 2010-11-10 | Memory Pharmaceuticals Corporation | Indoles, 1h-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof |
| ES2342675T3 (es) * | 2004-12-22 | 2010-07-12 | Memory Pharmaceuticals Corporation | Ligandos del receptor alfa-7 nicotinico contra enfermedades relacionadas con el snc. |
-
2008
- 2008-09-30 EP EP08835512A patent/EP2217597B1/en not_active Not-in-force
- 2008-09-30 JP JP2010527249A patent/JP5022494B2/ja not_active Expired - Fee Related
- 2008-09-30 CN CN201410331886.8A patent/CN104193741B/zh not_active Expired - Fee Related
- 2008-09-30 WO PCT/US2008/078320 patent/WO2009046025A1/en not_active Ceased
- 2008-09-30 KR KR1020107008479A patent/KR101565469B1/ko not_active Expired - Fee Related
- 2008-09-30 CA CA2701126A patent/CA2701126A1/en not_active Abandoned
- 2008-09-30 DK DK08835512.8T patent/DK2217597T3/da active
- 2008-09-30 CN CN2008801186316A patent/CN101883771A/zh active Pending
- 2008-09-30 ES ES08835512T patent/ES2362326T3/es active Active
- 2008-09-30 US US12/242,389 patent/US8114891B2/en not_active Expired - Fee Related
- 2008-09-30 DE DE602008005928T patent/DE602008005928D1/de active Active
- 2008-09-30 AT AT08835512T patent/ATE503754T1/de active
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Also Published As
| Publication number | Publication date |
|---|---|
| HK1204616A1 (en) | 2015-11-27 |
| US8114891B2 (en) | 2012-02-14 |
| KR101565469B1 (ko) | 2015-11-03 |
| KR20100068290A (ko) | 2010-06-22 |
| MX2010003375A (es) | 2010-05-17 |
| JP2010540562A (ja) | 2010-12-24 |
| ES2362326T3 (es) | 2011-07-01 |
| ATE503754T1 (de) | 2011-04-15 |
| CA2701126A1 (en) | 2009-04-09 |
| WO2009046025A1 (en) | 2009-04-09 |
| EP2217597B1 (en) | 2011-03-30 |
| DK2217597T3 (da) | 2011-06-20 |
| DE602008005928D1 (de) | 2011-05-12 |
| EP2217597A1 (en) | 2010-08-18 |
| US20090088418A1 (en) | 2009-04-02 |
| CN101883771A (zh) | 2010-11-10 |
| CN104193741B (zh) | 2016-08-24 |
| CN104193741A (zh) | 2014-12-10 |
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