KR20090130105A - 치환된 2,3,4,5-테트라히드로-1h-피리도[4,3-b] 인돌, 그 제조방법 및 용도 - Google Patents
치환된 2,3,4,5-테트라히드로-1h-피리도[4,3-b] 인돌, 그 제조방법 및 용도 Download PDFInfo
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- KR20090130105A KR20090130105A KR1020097023171A KR20097023171A KR20090130105A KR 20090130105 A KR20090130105 A KR 20090130105A KR 1020097023171 A KR1020097023171 A KR 1020097023171A KR 20097023171 A KR20097023171 A KR 20097023171A KR 20090130105 A KR20090130105 A KR 20090130105A
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- South Korea
- Prior art keywords
- pyrido
- indole
- tetrahydro
- formula
- methyl
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- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title abstract description 16
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 134
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 150000003839 salts Chemical class 0.000 claims abstract description 78
- 125000001424 substituent group Chemical group 0.000 claims abstract description 47
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 41
- 150000004677 hydrates Chemical class 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 13
- 125000003277 amino group Chemical group 0.000 claims abstract description 11
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 6
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- -1 (2-phenylethenyl) 2,3,4,5-tetrahydro -1H- pyrido [4, 3-b] indole Chemical compound 0.000 claims description 228
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 72
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- 108020003175 receptors Proteins 0.000 claims description 51
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- NESQBWDSPUMXBW-UHFFFAOYSA-N 5-ethyl-1,2,3,4-tetrahydropyrido[4,3-b]indole Chemical class C12=CC=CC=C2N(CC)C2=C1CNCC2 NESQBWDSPUMXBW-UHFFFAOYSA-N 0.000 claims description 8
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- XBVCLWSNUNVPNC-UHFFFAOYSA-N 2-methyl-5-(2-pyridin-3-ylethynyl)-8-(trifluoromethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C(F)(F)F)=CC=C1N2C#CC1=CC=CN=C1 XBVCLWSNUNVPNC-UHFFFAOYSA-N 0.000 claims description 4
- HCWWPLNFZNUYRH-UHFFFAOYSA-N 8-fluoro-2-methyl-5-(2-pyridin-4-ylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(F)=CC=C1N2C#CC1=CC=NC=C1 HCWWPLNFZNUYRH-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- NCRLGWIBMFMWHM-UHFFFAOYSA-N 2,8-dimethyl-5-(2-phenylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2C#CC1=CC=CC=C1 NCRLGWIBMFMWHM-UHFFFAOYSA-N 0.000 claims description 3
- DUUHEGAGOHEODE-UHFFFAOYSA-N 2,8-dimethyl-5-(2-pyrazin-2-ylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CN=CC=N1 DUUHEGAGOHEODE-UHFFFAOYSA-N 0.000 claims description 3
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- CTSIMNCXAXCWOY-UHFFFAOYSA-N 2,8-dimethyl-5-(2-pyridin-3-ylethynyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2C#CC1=CC=CN=C1 CTSIMNCXAXCWOY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- KPGWZRTZTASLIF-UHFFFAOYSA-N 2-methyl-5-(2-phenylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical group C1N(C)CCC2=C1C1=CC=CC=C1N2CCC1=CC=CC=C1 KPGWZRTZTASLIF-UHFFFAOYSA-N 0.000 claims description 3
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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| EP2537849A3 (en) | 2006-01-17 | 2013-04-03 | Vertex Pharmaceuticals, Inc. | Azaindoles useful as inhibitors of janus kinases |
| WO2008076392A2 (en) | 2006-12-14 | 2008-06-26 | Vertex Pharmaceuticals Incorporated | Compounds useful as protein kinase inhibitors |
| RU2007139634A (ru) | 2007-10-25 | 2009-04-27 | Сергей Олегович Бачурин (RU) | Новые тиазол-, триазол- или оксадиазол-содержащие тетрациклические соединения |
| JP2011507835A (ja) * | 2007-12-21 | 2011-03-10 | アンドレイ・アレクサンドロビッチ・イワシェンコ | α−アドレナリン受容体、ドーパミン、ヒスタミン、イミダゾリン及びセロトニン受容体のリガンド並びにその使用 |
| RU2544856C2 (ru) | 2008-01-25 | 2015-03-20 | Сергей Олегович Бачурин | НОВЫЕ ПРОИЗВОДНЫЕ 2,3,4,5-ТЕТРАГИДРО-1-ПИРИДО[4,3-b]ИНДОЛА И СПОСОБЫ ИХ ПРИМЕНЕНИЯ |
| EP2280968A2 (en) | 2008-03-24 | 2011-02-09 | Medivation Technologies, Inc. | Pyrido [3, 4-b]indoles and methods of use |
| PE20091820A1 (es) | 2008-03-24 | 2009-12-10 | Medivation Technologies Inc | Compuestos heterociclicos con uniones puente y metodos para usarlos |
| US8907097B2 (en) * | 2008-10-31 | 2014-12-09 | Medivation Technologies, Inc. | Pyrido[4,3-b]indoles containing rigid moieties |
| JP5551708B2 (ja) | 2008-10-31 | 2014-07-16 | メディベイション テクノロジーズ, インコーポレイテッド | アゼピノ[4,5−b]インドール化合物およびその使用方法 |
| US9962368B2 (en) | 2009-01-09 | 2018-05-08 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| US9162980B2 (en) | 2009-01-09 | 2015-10-20 | Board Of Regents Of The University Of Texas System | Anti-depression compounds |
| US8362277B2 (en) | 2009-01-09 | 2013-01-29 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| US8604074B2 (en) | 2009-01-09 | 2013-12-10 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| KR20110132564A (ko) * | 2009-02-11 | 2011-12-08 | 선오비온 파마슈티컬스 인코포레이티드 | 히스타민 h3 역 작용제 및 길항제, 및 이의 사용 방법 |
| WO2010115342A1 (zh) * | 2009-04-10 | 2010-10-14 | 中国人民解放军军事医学科学院毒物药物研究所 | 含有四氢吡啶[4,3-b]吲哚衍生物的缓释组合物及该衍生物的制备方法 |
| EP2424364A4 (en) * | 2009-04-29 | 2012-12-19 | Medivation Technologies Inc | PYRIDO [4.3-B] INDOLES AND METHODS OF USE |
| US8741919B2 (en) | 2009-04-29 | 2014-06-03 | Medivation Technologies, Inc. | Pyrido[4,3-B]indoles and methods of use |
| SG10201405826RA (en) | 2009-06-17 | 2014-12-30 | Vertex Pharma | Inhibitors of influenza viruses replication |
| RU2009128817A (ru) * | 2009-07-28 | 2011-02-10 | Общество с ограниченной ответственностью "Инномед" (RU) | Производные гидрированных пиридо[4,3-b]индолов, фармацевтическая композиция, способы получения и применения |
| EP2475664A2 (en) * | 2009-09-11 | 2012-07-18 | Sunovion Pharmaceuticals Inc. | Histamine h3 inverse agonists and antagonists and methods of use thereof |
| CA2775328A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Pyrido[4,3-b]indoles and methods of use |
| WO2011038163A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Pyrido[3,4-b]indoles and methods of use |
| BR112012006648A2 (pt) | 2009-09-23 | 2019-09-24 | Medivation Neurology Inc | composto,método de tratamento de um distúrbio cognitivo, distúrbio psicótico, distúrbio mediado por neurotransmissor ou um distúrbio neuronal, composição farmacêutica e kit |
| US20130137705A1 (en) * | 2009-09-23 | 2013-05-30 | Sarvajit Chakravarty | Pyrido[3,4-b]indoles and methods of use |
| WO2011103433A1 (en) | 2010-02-18 | 2011-08-25 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
| US9040519B2 (en) | 2010-02-18 | 2015-05-26 | Medivation Technologies, Inc. | Fused tetracyclic pyrido [4,3-B] indole and pyrido [3,4-B] indole derivatives and methods of use |
| US9193728B2 (en) | 2010-02-18 | 2015-11-24 | Medivation Technologies, Inc. | Fused tetracyclic pyrido [4,3-B] indole and pyrido [3,4-B] indole derivatives and methods of use |
| WO2011103430A1 (en) | 2010-02-19 | 2011-08-25 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
| WO2011103448A1 (en) * | 2010-02-19 | 2011-08-25 | Medivation Technologies, Inc. | Methods and compositions for treating psychotic disorders using antipsychotic combination therapy |
| CA2804161A1 (en) | 2010-07-07 | 2012-01-12 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| US9035056B2 (en) | 2011-02-18 | 2015-05-19 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
| US9434747B2 (en) | 2011-02-18 | 2016-09-06 | Medivation Technologies, Inc. | Methods of treating diabetes |
| US9199985B2 (en) | 2011-02-18 | 2015-12-01 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| WO2012154261A1 (en) * | 2011-02-18 | 2012-11-15 | Medivation Technologies, Inc. | Compounds and methods of treating diabetes |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| RU2490268C2 (ru) * | 2011-11-10 | 2013-08-20 | Федеральное Государственное Бюджетное Учреждение Науки Институт Физиологически Активных Веществ Российской Академии Наук (Ифав Ран) | ХЛОРГИДРАТЫ ФТОРСОДЕРЖАЩИХ ЗАМЕЩЕННЫХ 5-[2-(ПИРИД-3-ИЛ)-ЭТИЛ]-2,3,4,5-ТЕТРАГИДРО-1Н-ПИРИДО[4,3-b]ИНДОЛОВ, В КАЧЕСТВЕ СРЕДСТВ СНИЖЕНИЯ НЕКОНТРОЛИРУЕМОЙ АГРЕГАЦИИ БЕЛКОВ В НЕРВНОЙ СИСТЕМЕ, ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ИХ ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
| CA2882826A1 (en) | 2012-08-24 | 2014-02-27 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| US9902713B2 (en) | 2013-11-11 | 2018-02-27 | Board Of Regents Of The University Of Texas System | Neuroprotective compounds and use thereof |
| WO2015070237A1 (en) | 2013-11-11 | 2015-05-14 | Board Of Regents Of The University Of Texas System | Neuroprotective chemicals and methods for identifying and using same |
| PT3068776T (pt) | 2013-11-13 | 2019-08-26 | Vertex Pharma | Inibidores da replicação de vírus da gripe |
| WO2015073481A1 (en) | 2013-11-13 | 2015-05-21 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| EP3294735B8 (en) | 2015-05-13 | 2022-01-05 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| JP6704416B2 (ja) | 2015-05-13 | 2020-06-03 | バーテックス ファーマシューティカルズ インコーポレイテッドVertex Pharmaceuticals Incorporated | インフルエンザウイルスの複製の阻害剤を調製する方法 |
| JP6757037B2 (ja) * | 2016-02-15 | 2020-09-16 | 学校法人近畿大学 | ストレス評価方法 |
| EA202191320A1 (ru) * | 2020-03-19 | 2021-10-22 | Андрей Александрович ИВАЩЕНКО | Норадренергический и специфически серотонинергический анксиолитик и антидепрессант, способ его получения и применения |
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| US3484449A (en) * | 1966-05-12 | 1969-12-16 | Hoffmann La Roche | Certain substituted phenyl amino-ethylpyridine intermediates |
| US3502688A (en) * | 1968-09-10 | 1970-03-24 | Hoffmann La Roche | 5-(4-pyridylethyl)-pyridoindole derivatives |
| RU2140417C1 (ru) | 1995-10-17 | 1999-10-27 | Институт физиологически активных веществ РАН | Производные гидрированных пиридо(4,3-b)индолов, способы их получения, фармацевтическая композиция и способ лечения |
| RU2106864C1 (ru) * | 1995-10-23 | 1998-03-20 | Николай Серафимович Зефиров | Средство для лечения болезни альцгеймера |
| RU2283108C2 (ru) | 2003-12-08 | 2006-09-10 | Сергей Олегович Бачурин | ГЕРОПРОТЕКТОР НА ОСНОВЕ ГИДРИРОВАННЫХ ПИРИДО(4,3-b) ИНДОЛОВ (ВАРИАНТЫ), ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕГО ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
| AU2007309390A1 (en) * | 2006-10-27 | 2008-05-02 | Medivation Neurology, Inc. | Methods and combination therapies for treating Alzheimer's disease |
| RU2334514C1 (ru) * | 2006-12-01 | 2008-09-27 | Институт физиологически активных веществ Российской Академии наук | СРЕДСТВО ДЛЯ УЛУЧШЕНИЯ КОГНИТИВНЫХ ФУНКЦИЙ И ПАМЯТИ НА ОСНОВЕ ГИДРИРОВАННЫХ ПИРИДО (4,3-b) ИНДОЛОВ (ВАРИАНТЫ), ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕГО ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
| JP2010540439A (ja) * | 2007-09-20 | 2010-12-24 | ディー2イー,エルエルシー | 神経保護性の及び認知を向上させる性質を備えた水素化されたピリド[4,3−b]インドール類のフッ素を含有する誘導体、調製するための工程、並びに使用 |
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| JP2011507835A (ja) * | 2007-12-21 | 2011-03-10 | アンドレイ・アレクサンドロビッチ・イワシェンコ | α−アドレナリン受容体、ドーパミン、ヒスタミン、イミダゾリン及びセロトニン受容体のリガンド並びにその使用 |
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| JP5580731B2 (ja) | 2014-08-27 |
| AU2008236872B2 (en) | 2013-01-17 |
| JP2010523556A (ja) | 2010-07-15 |
| WO2008123796A2 (ru) | 2008-10-16 |
| UA98324C2 (ru) | 2012-05-10 |
| WO2008123796A3 (ru) | 2008-12-31 |
| EP2145887A4 (en) | 2011-03-02 |
| EP2145887A2 (en) | 2010-01-20 |
| RU2334747C1 (ru) | 2008-09-27 |
| US20130217703A1 (en) | 2013-08-22 |
| US8541437B2 (en) | 2013-09-24 |
| CA2683453C (en) | 2013-06-11 |
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