CA2701126A1 - 4-substituted quinuclidine derivatives, methods of production, and pharmaceutical uses thereof - Google Patents
4-substituted quinuclidine derivatives, methods of production, and pharmaceutical uses thereof Download PDFInfo
- Publication number
- CA2701126A1 CA2701126A1 CA2701126A CA2701126A CA2701126A1 CA 2701126 A1 CA2701126 A1 CA 2701126A1 CA 2701126 A CA2701126 A CA 2701126A CA 2701126 A CA2701126 A CA 2701126A CA 2701126 A1 CA2701126 A1 CA 2701126A1
- Authority
- CA
- Canada
- Prior art keywords
- ylmethyl
- compound
- indole
- carboxylate
- solvate
- 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
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- -1 4-substituted quinuclidine Chemical class 0.000 title claims description 43
- 238000004519 manufacturing process Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 278
- 239000000203 mixture Substances 0.000 claims abstract description 97
- 238000009472 formulation Methods 0.000 claims abstract description 73
- 150000003839 salts Chemical class 0.000 claims description 162
- 239000012453 solvate Substances 0.000 claims description 147
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 73
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
- 238000011282 treatment Methods 0.000 claims description 33
- 239000008177 pharmaceutical agent Substances 0.000 claims description 32
- 230000001404 mediated effect Effects 0.000 claims description 31
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- PKBVKBLTOFEJGO-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-4-ylmethyl)-1,2-benzothiazole-3-carboxamide Chemical compound C1=CC=C2C(C(NCC34CCN(CC3)CC4)=O)=NSC2=C1 PKBVKBLTOFEJGO-UHFFFAOYSA-N 0.000 claims description 22
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 17
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- BYCMSLAAWXLXLI-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptan-4-ylmethyl 5-methoxy-1h-indole-3-carboxylate Chemical compound C12=CC(OC)=CC=C2NC=C1C(=O)OCC1(C2)CCN2CC1 BYCMSLAAWXLXLI-UHFFFAOYSA-N 0.000 claims description 12
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- C07D—HETEROCYCLIC COMPOUNDS
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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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| US97672407P | 2007-10-01 | 2007-10-01 | |
| US60/976,724 | 2007-10-01 | ||
| PCT/US2008/078320 WO2009046025A1 (en) | 2007-10-01 | 2008-09-30 | Quinuclidin-4-ylmethyl 1h-indole-3-carboxylate derivatives as alpha 7 nicotinic acetylcholine receptor ligands for the treatment of alzheimer's disease |
Publications (1)
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| CA2701126A1 true CA2701126A1 (en) | 2009-04-09 |
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| CA2701126A Abandoned CA2701126A1 (en) | 2007-10-01 | 2008-09-30 | 4-substituted quinuclidine derivatives, methods of production, and pharmaceutical uses thereof |
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| WO (1) | WO2009046025A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| KR20140146216A (ko) | 2008-11-19 | 2014-12-24 | 포럼 파마슈티칼즈 인크. | (ｒ)-７-클로로-ｎ-(퀴누클리딘-３-일)벤조［ｂ］티오펜-２-카르복사미드 및 그 약학적으로 허용가능한 염을 이용한 인지 장애의 치료 |
| PE20120324A1 (es) * | 2009-05-11 | 2012-04-17 | Envivo Pharmaceuticals Inc | Combinacion que comprende (r)-7-cloro-n-(quinuclidin-3-il)benzo[b]tiofeno-2-carboxamida y donezepilo como moduladora de trastornos cognitivos |
| TWI558398B (zh) | 2009-09-22 | 2016-11-21 | 諾華公司 | 菸鹼乙醯膽鹼受體α７活化劑之用途 |
| MY165234A (en) | 2010-05-17 | 2018-03-14 | Forum Pharmaceuticals Inc | A crystalline form of (r)-7-chloro-n-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate |
| WO2011163539A2 (en) * | 2010-06-25 | 2011-12-29 | The Johns Hopkins University | nAChRα7 AGONISTS AND nAChRα7 ANTAGONISTS FOR TREATING ULCERATIVE COLITIS (UC) AND CROHN'S DISEASE (CD) |
| RU2014103474A (ru) * | 2011-07-01 | 2015-08-10 | Энвиво Фармасьютикалз, Инк. | Способы лечения умеренных когнитивных нарушений |
| JP6088491B2 (ja) * | 2012-04-10 | 2017-03-01 | 大日本住友製薬株式会社 | 新規１位置換インダゾール誘導体 |
| US9585877B2 (en) | 2012-05-08 | 2017-03-07 | Forum Pharmaceuticals, Inc. | Methods of maintaining, treating or improving cognitive function |
| 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 |
| CA2903431C (en) | 2013-03-14 | 2022-12-06 | Kalyra Pharmaceuticals, Inc. | Bicyclopentane analgesic compounds |
| EA032196B1 (ru) | 2013-10-03 | 2019-04-30 | Кура Онколоджи, Инк. | Ингибиторы erk и способы применения |
| US10189780B2 (en) | 2013-12-12 | 2019-01-29 | Zeno Royalties & Milestones, LLC | Bicyclic alkyl compounds and synthesis |
| WO2015134710A1 (en) | 2014-03-07 | 2015-09-11 | Kalyra Pharmaceuticals, Inc. | Propellane derivates and synthesis |
| EP3166940A4 (en) * | 2014-07-11 | 2018-04-25 | Alpharmagen, LLC | Quinuclidine compounds for modulating alpha7 -nicotinic acetylcholine receptor activity |
| EP3193855B1 (en) | 2014-09-17 | 2021-05-19 | Recurium IP Holdings, LLC | Bicyclic compounds |
| WO2017120532A1 (en) * | 2016-01-08 | 2017-07-13 | Alpharmagen, Llc | Polymorphs of a phosphate salt of quinuclidin-4-ylmethyl 4-methyl-1h-indole-3-carboxylate and uses thereof |
| US20190083460A1 (en) * | 2016-03-16 | 2019-03-21 | Zeno Royalties & Milestones, LLC | Analgesic compounds |
| MX389668B (es) | 2017-05-15 | 2025-03-20 | Recurium Ip Holdings Llc | Compuestos biciclo[1.1.1]pentilo sustituidos y uso de los mismos para el tratamiento del dolor y fiebre. |
| EP3520803A1 (en) * | 2018-01-31 | 2019-08-07 | Zarodex Therapeutics Limited | Novel uses |
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| NL8701682A (nl) | 1986-07-30 | 1988-02-16 | Sandoz Ag | Werkwijze voor het therapeutisch toepassen van serotonine antagonisten, aktieve verbindingen en farmaceutische preparaten die deze verbindingen bevatten. |
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| US5712270A (en) | 1995-11-06 | 1998-01-27 | American Home Products Corporation | 2-arylamidothiazole derivatives with CNS activity |
| SE9600683D0 (sv) | 1996-02-23 | 1996-02-23 | Astra Ab | Azabicyclic esters of carbamic acids useful in therapy |
| AUPN862996A0 (en) | 1996-03-13 | 1996-04-04 | Fujisawa Pharmaceutical Co., Ltd. | A novel substituted-acetamide compound |
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| EP1381603A2 (en) | 2000-08-18 | 2004-01-21 | PHARMACIA & UPJOHN COMPANY | Quinuclidine-substituedaryl moieties for treatment of disease ( nicotinic acetylcholine receptor ligands ) |
| AU2001282875A1 (en) | 2000-08-21 | 2002-03-04 | Pharmacia And Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease |
| EP1311505A2 (en) | 2000-08-21 | 2003-05-21 | PHARMACIA & UPJOHN COMPANY | Quinuclidine-substituted heteroaryl moieties for treatment of disease ( nicotinic acetylcholine receptor ligands ) |
| WO2002015662A2 (en) | 2000-08-21 | 2002-02-28 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease (nicotinic acetylcholine receptor antagonists |
| PE20020719A1 (es) | 2000-12-22 | 2002-10-11 | Almirall Prodesfarma Ag | Derivados de carbamato de quinuclidina como agentes antimuscarinicos m3 |
| CN100484937C (zh) * | 2002-09-25 | 2009-05-06 | 记忆药物公司 | 吲唑、苯并噻唑和苯并异噻唑，以及它们的制备和用途 |
| US7488737B2 (en) | 2004-04-22 | 2009-02-10 | Memory Pharmaceutical Corporation | Indoles, 1H-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof |
| BRPI0517494A (pt) | 2004-12-22 | 2008-10-14 | Memory Pharm Corp | composto, composição farmacêutica, método de ativação/estimulação seletiva de receptores nicotìnicos de a-7 em um paciente em que tal ativação/estimulação tem um efeito terapêutico, método de tratamento de um paciente que sofre de uma doença psicótica, uma doença neurodegenerativa que envolve uma disfunção do sistema colinérgico, e/ou uma condição de debilitação da memória e/ou da cognição, método de tratamento de um paciente que sofre de demência e/ou uma outra condição com perda da memória, método de tratamento de um paciente que sofre de debilitação da memória devido à debilitação cognitiva suave devido ao envelhecimento, mal de alzheimer, esquizofrenia, mal de parkinson, mal de huntington, mal de pick, mal de creutzfeldt-jakob, depressão, envelhecimento, trauma na cabeça, acidente vascular cerebral, hipoxia do snc, senilidade cerebral, demência de multiinfarto, hiv e/ou doença cardiovascular, método de tratamento e/ou prevenção da demência em um paciente com o mal de alzheimer, método de tratamento de um paciente para cortar o vìcio do álcool ou o tratamento de um paciente com a terapia anti-intoxicação, método de tratamento de um paciente para propiciar neuroproteção contra os danos associados com acidentes vasculares cerebrais e isquemia e excitotoxicidade induzida por glutamatos, método de tratamento de um paciente que sofre do vìcio da nicotina, dor, tontura do fuso horário, obesidade e/ou diabetes, método de indução do ato de parar fumar em um paciente, método de tratamento de um paciente que sofre de debilitação cognitiva suave (mci), demência vascular (vad), declìnio cognitivo associado com a idade (aacd), amnésia associada com a cirurgia com o coração aberto, parada cardìaca, anestesia geral, deficiências da memória devido à exposição a agentes anestésicos, debilitação cognitiva induzida pela privação do sono, sìndrome de fadiga crÈnica, narcolepsia, demência relacionada com a aids, debilitação cognitiva relacionada com a epilepsia, sìndrome de down, demência relacionada ao alcoolismo, debilitações da memória induzidas por drogas/substáncias, demência pugilìstica (sìndrome do boxeador), ou demência animal, método para o tratamento da perda da memória, método para o tratamento de um paciente que sofre de debilitação da memória, método para o tratamento ou a profilaxia de uma doença ou de uma condição resultante da disfunção da transmissão do receptor nicotìnico de acetilcolina em um paciente, método para o tratamento ou a profilaxia de uma doença ou de uma condição resultante de receptores nicotìnicos de acetilcolina defeituosos ou funcionando mal em um paciente, método para o tratamento ou a profilaxia de uma doença ou de uma condição resultante da transmissão suprimida do receptor nicotìnico de acetilcolina em um paciente, método para o tratamento ou a profilaxia de uma doença ou de uma condição resultante da perda de sinapses colinérgicas em um paciente, método para a proteção dos neurÈnios em um paciente com neurotoxicidade induzi |
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2008
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- 2008-09-30 KR KR1020107008479A patent/KR101565469B1/ko not_active Expired - Fee Related
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- 2008-09-30 CA CA2701126A patent/CA2701126A1/en not_active Abandoned
- 2008-09-30 WO PCT/US2008/078320 patent/WO2009046025A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| KR101565469B1 (ko) | 2015-11-03 |
| HK1204616A1 (en) | 2015-11-27 |
| CN104193741A (zh) | 2014-12-10 |
| US20090088418A1 (en) | 2009-04-02 |
| ATE503754T1 (de) | 2011-04-15 |
| KR20100068290A (ko) | 2010-06-22 |
| US8114891B2 (en) | 2012-02-14 |
| EP2217597B1 (en) | 2011-03-30 |
| DK2217597T3 (da) | 2011-06-20 |
| MX2010003375A (es) | 2010-05-17 |
| EP2217597A1 (en) | 2010-08-18 |
| JP2010540562A (ja) | 2010-12-24 |
| DE602008005928D1 (de) | 2011-05-12 |
| JP5022494B2 (ja) | 2012-09-12 |
| CN104193741B (zh) | 2016-08-24 |
| WO2009046025A1 (en) | 2009-04-09 |
| CN101883771A (zh) | 2010-11-10 |
| ES2362326T3 (es) | 2011-07-01 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20130924 |
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| FZDE | Discontinued |
Effective date: 20171213 |