JP2012507567A5 - - Google Patents
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- JP2012507567A5 JP2012507567A5 JP2011534828A JP2011534828A JP2012507567A5 JP 2012507567 A5 JP2012507567 A5 JP 2012507567A5 JP 2011534828 A JP2011534828 A JP 2011534828A JP 2011534828 A JP2011534828 A JP 2011534828A JP 2012507567 A5 JP2012507567 A5 JP 2012507567A5
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- Japan
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- independently
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 143
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- 125000005843 halogen group Chemical group 0.000 claims description 56
- -1 perhaloalkyl Chemical group 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 38
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000005102 carbonylalkoxy group Chemical group 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000004423 acyloxy group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 15
- 125000004001 thioalkyl group Chemical group 0.000 claims description 15
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000004442 acylamino group Chemical group 0.000 claims description 13
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 150000003573 thiols Chemical class 0.000 claims description 8
- 125000005589 carbonylalkylenealkoxy group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 3
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 102000000543 Histamine Receptors Human genes 0.000 claims description 2
- 108010002059 Histamine Receptors Proteins 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 7
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 description 21
- 208000024891 symptom Diseases 0.000 description 19
- 208000028698 Cognitive impairment Diseases 0.000 description 18
- 208000028017 Psychotic disease Diseases 0.000 description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 208000035475 disorder Diseases 0.000 description 13
- 238000000034 method Methods 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 230000007370 cognitive improvement Effects 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 0 CC*c1c(C)cccc1 Chemical compound CC*c1c(C)cccc1 0.000 description 3
- 125000002757 morpholinyl group Chemical group 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 125000005121 aminocarbonylalkoxy group Chemical group 0.000 description 2
- 230000000561 anti-psychotic effect Effects 0.000 description 2
- 230000019771 cognition Effects 0.000 description 2
- 230000001149 cognitive effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000003414 procognitive effect Effects 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11052708P | 2008-10-31 | 2008-10-31 | |
| US61/110,527 | 2008-10-31 | ||
| US17396509P | 2009-04-29 | 2009-04-29 | |
| US61/173,965 | 2009-04-29 | ||
| US24525709P | 2009-09-23 | 2009-09-23 | |
| US61/245,257 | 2009-09-23 | ||
| PCT/US2009/062872 WO2010051503A1 (en) | 2008-10-31 | 2009-10-30 | Azepino [4, 5-b] indoles and methods of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012507567A JP2012507567A (ja) | 2012-03-29 |
| JP2012507567A5 true JP2012507567A5 (https=) | 2012-12-20 |
| JP5551708B2 JP5551708B2 (ja) | 2014-07-16 |
Family
ID=42129314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011534828A Expired - Fee Related JP5551708B2 (ja) | 2008-10-31 | 2009-10-30 | アゼピノ［４，５−ｂ］インドール化合物およびその使用方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US8569287B2 (https=) |
| EP (1) | EP2348847A4 (https=) |
| JP (1) | JP5551708B2 (https=) |
| CN (1) | CN102316732B (https=) |
| AR (1) | AR073924A1 (https=) |
| AU (1) | AU2009308708B2 (https=) |
| BR (1) | BRPI0921798A2 (https=) |
| CA (1) | CA2742322A1 (https=) |
| TW (1) | TWI482773B (https=) |
| WO (1) | WO2010051503A1 (https=) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2007139634A (ru) | 2007-10-25 | 2009-04-27 | Сергей Олегович Бачурин (RU) | Новые тиазол-, триазол- или оксадиазол-содержащие тетрациклические соединения |
| 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 |
| CL2009000725A1 (es) | 2008-03-24 | 2009-05-29 | Medivation Technologies Inc | Compuestos derivados de heterociclos con uniones puente sustituidos, moduladores de receptores adrenergicos, de serotonina, de dopamina y de histaminas; composicion farmaceutica; kit farmaceutico; y su uso en el tratamiento del trastorno cognitivo y trastorno psicotico. |
| WO2009120717A2 (en) | 2008-03-24 | 2009-10-01 | Medivation Technologies, Inc. | Pyrido [3, 4-b] indoles and methods of use |
| TWI477503B (zh) * | 2008-10-31 | 2015-03-21 | Medivation Technologies Inc | 含有剛性部分之吡啶并〔４，３－ｂ〕吲哚 |
| AU2009308708B2 (en) | 2008-10-31 | 2015-11-19 | Medivation Technologies, Inc. | Azepino [4, 5-b] indoles and methods of use |
| US20100113472A1 (en) * | 2008-11-03 | 2010-05-06 | Chemocentryx, Inc. | Compounds for the treatment of osteoporosis and cancers |
| US8362277B2 (en) | 2009-01-09 | 2013-01-29 | 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 |
| US9962368B2 (en) | 2009-01-09 | 2018-05-08 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| CA2748813C (en) | 2009-01-09 | 2018-07-10 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| BRPI1008020A2 (pt) | 2009-02-11 | 2016-03-15 | Sunovion Pharmaceuticals Inc | antagonistas e agonistas inversos h3 da histamina e métodos de uso dos mesmos |
| CA2760541A1 (en) | 2009-04-29 | 2010-11-04 | Medivation Technologies, Inc. | Pyrido[4,3-b] indoles and methods of use |
| EP2424366B1 (en) | 2009-04-29 | 2016-02-17 | Medivation Technologies, Inc. | Pyrido [4, 3-b]indoles and methods of use |
| MX2012002898A (es) * | 2009-09-11 | 2012-04-02 | Sunovion Pharmaceuticals Inc | Agonistas y antagonistas inversos de histamina h3 y metodos de uso para los mismos. |
| WO2011038164A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Bridged heterocyclic compounds and methods of use |
| CA2775328A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Pyrido[4,3-b]indoles and methods of use |
| US9079904B2 (en) | 2009-09-23 | 2015-07-14 | Medivation Technologies, Inc. | 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 |
| WO2011103460A1 (en) | 2010-02-18 | 2011-08-25 | Medivation Technologies, Inc. | Fused tetracyclic pyrido[4,3-b]indole and pyrido[3,4-b]ondole 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 |
| CA2804161A1 (en) | 2010-07-07 | 2012-01-12 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| WO2012112964A2 (en) * | 2011-02-18 | 2012-08-23 | Medivation Technologies, Inc. | PYRIDO[4,3-b]INDOLE AND PYRIDO[3,4-b]INDOLE DERIVATIVES AND METHODS OF USE |
| WO2012112963A1 (en) | 2011-02-18 | 2012-08-23 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| US8791132B2 (en) * | 2011-02-18 | 2014-07-29 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| US9434747B2 (en) | 2011-02-18 | 2016-09-06 | Medivation Technologies, Inc. | Methods of treating diabetes |
| WO2014031165A1 (en) * | 2012-08-22 | 2014-02-27 | Medivation Technologies, Inc. | Compounds and methods of treating diabetes |
| CA2882826A1 (en) | 2012-08-24 | 2014-02-27 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| EP2746257A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2746258A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP3068388A4 (en) | 2013-11-11 | 2017-04-12 | 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 |
| CN105037298B (zh) * | 2015-07-08 | 2017-09-26 | 华南理工大学 | 一种含三氟甲基取代连续季碳中心环氧丙烷衍生物及合成方法 |
| EP3519816A4 (en) | 2016-09-29 | 2020-05-06 | The Regents of the University of California | CONNECTIONS FOR INCREASING NEURONAL PLASTICITY |
| CA3129749A1 (en) * | 2019-02-13 | 2020-08-20 | Centre For Addiction And Mental Health | Compositions and methods relating to use of agonists of alpha5-containing gabaa receptors |
| KR102946120B1 (ko) * | 2019-02-27 | 2026-03-30 | 더 리젠츠 오브 더 유니버시티 오브 캘리포니아 | 뇌 장애를 치료하기 위한 아제피노-인돌 및 다른 헤테로사이클 |
| CN110526935A (zh) * | 2019-09-04 | 2019-12-03 | 天津理工大学 | 一种双硼氮杂菲及其衍生物的合成方法 |
| IL313455A (en) | 2021-12-15 | 2024-08-01 | Delix Therapeutics Inc | Phenoxy and benzyloxy modified psychroplastogens and their uses |
| CN117510403A (zh) * | 2022-07-29 | 2024-02-06 | 阿里生物新材料（常州）有限公司 | 一种3-乙基-吡啶-2-甲脒盐酸盐的合成方法 |
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-
2009
- 2009-10-30 AU AU2009308708A patent/AU2009308708B2/en not_active Ceased
- 2009-10-30 WO PCT/US2009/062872 patent/WO2010051503A1/en not_active Ceased
- 2009-10-30 US US12/610,152 patent/US8569287B2/en not_active Expired - Fee Related
- 2009-10-30 EP EP09824200A patent/EP2348847A4/en not_active Withdrawn
- 2009-10-30 CN CN200980153432.3A patent/CN102316732B/zh not_active Expired - Fee Related
- 2009-10-30 BR BRPI0921798A patent/BRPI0921798A2/pt not_active IP Right Cessation
- 2009-10-30 TW TW098137049A patent/TWI482773B/zh not_active IP Right Cessation
- 2009-10-30 CA CA2742322A patent/CA2742322A1/en not_active Abandoned
- 2009-10-30 JP JP2011534828A patent/JP5551708B2/ja not_active Expired - Fee Related
- 2009-10-30 AR ARP090104221A patent/AR073924A1/es unknown
-
2013
- 2013-03-08 US US13/791,648 patent/US9409910B2/en not_active Expired - Fee Related
- 2013-03-08 US US13/791,867 patent/US20130190295A1/en not_active Abandoned
- 2013-10-08 US US14/048,656 patent/US9481676B2/en not_active Expired - Fee Related
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