JP2012507566A5 - - Google Patents
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- JP2012507566A5 JP2012507566A5 JP2011534826A JP2011534826A JP2012507566A5 JP 2012507566 A5 JP2012507566 A5 JP 2012507566A5 JP 2011534826 A JP2011534826 A JP 2011534826A JP 2011534826 A JP2011534826 A JP 2011534826A JP 2012507566 A5 JP2012507566 A5 JP 2012507566A5
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- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- compound
- salt
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 94
- -1 perhaloalkyl Chemical group 0.000 claims description 68
- 150000003839 salts Chemical class 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- 125000001475 halogen functional group Chemical group 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 208000010877 cognitive disease Diseases 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 208000028017 Psychotic disease Diseases 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000004442 acylamino group Chemical group 0.000 claims description 22
- 125000005102 carbonylalkoxy group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000004423 acyloxy group Chemical group 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 125000005589 carbonylalkylenealkoxy group Chemical group 0.000 claims description 12
- 125000004001 thioalkyl group Chemical group 0.000 claims description 12
- 150000003573 thiols Chemical class 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- 230000001537 neural effect Effects 0.000 claims description 8
- 239000002858 neurotransmitter agent Substances 0.000 claims description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 6
- 125000005121 aminocarbonylalkoxy group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 12
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 208000035475 disorder Diseases 0.000 description 23
- 208000024891 symptom Diseases 0.000 description 19
- 208000028698 Cognitive impairment Diseases 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000003814 drug Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 0 CC(c(cc1)ccc1C(NC=C)=C[*@]1c(ccc(*)c2)c2C(C2)=C1CC*2N*=C)=C Chemical compound CC(c(cc1)ccc1C(NC=C)=C[*@]1c(ccc(*)c2)c2C(C2)=C1CC*2N*=C)=C 0.000 description 4
- 230000001149 cognitive effect Effects 0.000 description 4
- 230000019771 cognition Effects 0.000 description 3
- 230000007370 cognitive improvement Effects 0.000 description 3
- 102000000543 Histamine Receptors Human genes 0.000 description 2
- 108010002059 Histamine Receptors Proteins 0.000 description 2
- 230000000561 anti-psychotic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003414 procognitive effect Effects 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11051908P | 2008-10-31 | 2008-10-31 | |
| US61/110,519 | 2008-10-31 | ||
| US17396009P | 2009-04-29 | 2009-04-29 | |
| US61/173,960 | 2009-04-29 | ||
| US24515009P | 2009-09-23 | 2009-09-23 | |
| US61/245,150 | 2009-09-23 | ||
| PCT/US2009/062869 WO2010051501A1 (en) | 2008-10-31 | 2009-10-30 | Pyrido (4,3-b) indoles containing rigid moieties |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014087277A Division JP2014133759A (ja) | 2008-10-31 | 2014-04-21 | 剛性の部分を有するピリド［４，３−ｂ］インドール |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012507566A JP2012507566A (ja) | 2012-03-29 |
| JP2012507566A5 true JP2012507566A5 (enExample) | 2012-12-20 |
| JP5588991B2 JP5588991B2 (ja) | 2014-09-10 |
Family
ID=42129313
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011534826A Expired - Fee Related JP5588991B2 (ja) | 2008-10-31 | 2009-10-30 | 剛性の部分を有するピリド［４，３−ｂ］インドール |
| JP2014087277A Withdrawn JP2014133759A (ja) | 2008-10-31 | 2014-04-21 | 剛性の部分を有するピリド［４，３−ｂ］インドール |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014087277A Withdrawn JP2014133759A (ja) | 2008-10-31 | 2014-04-21 | 剛性の部分を有するピリド［４，３−ｂ］インドール |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US8907097B2 (enExample) |
| EP (1) | EP2346332A4 (enExample) |
| JP (2) | JP5588991B2 (enExample) |
| CN (1) | CN102271508B (enExample) |
| AR (1) | AR073923A1 (enExample) |
| AU (1) | AU2009308706C1 (enExample) |
| BR (1) | BRPI0919948A2 (enExample) |
| CA (1) | CA2742320A1 (enExample) |
| TW (1) | TWI477503B (enExample) |
| WO (1) | WO2010051501A1 (enExample) |
Families Citing this family (34)
| 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 |
| CA2742322A1 (en) | 2008-10-31 | 2010-05-06 | Medivation Technologies, Inc. | Azepino[4,5-b]indoles and methods of use |
| CA2742320A1 (en) | 2008-10-31 | 2010-05-06 | Medivation Technologies, Inc. | Pyrido[4,3-b]indoles containing rigid moieties |
| US9962368B2 (en) | 2009-01-09 | 2018-05-08 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| CN102405043B (zh) | 2009-01-09 | 2017-08-22 | 得克萨斯州大学系统董事会 | 前神经原性化合物 |
| US9162980B2 (en) | 2009-01-09 | 2015-10-20 | Board Of Regents Of The University Of Texas System | Anti-depression compounds |
| WO2010093425A1 (en) | 2009-02-11 | 2010-08-19 | Sepracor Inc. | Histamine h3 inverse agonists and antagonists and methods of use thereof |
| CN102480955B (zh) * | 2009-04-29 | 2015-08-05 | 梅迪维新技术公司 | 吡啶并[4,3-b]吲哚类和使用方法 |
| CA2760516A1 (en) * | 2009-04-29 | 2011-02-17 | Medivation Technologies, Inc. | Pyrido[4,3-b]indoles and methods of use |
| WO2011031818A2 (en) * | 2009-09-11 | 2011-03-17 | Sepracor Inc. | Histamine h3 inverse agonists and antagonists and methods of use thereof |
| WO2011038161A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Pyrido[4,3-b]indoles and methods of use |
| EP2480081A4 (en) | 2009-09-23 | 2013-03-06 | Medivation Technologies Inc | Bridged heterocyclic compounds and methods for their use |
| US9079904B2 (en) | 2009-09-23 | 2015-07-14 | Medivation Technologies, Inc. | Pyrido[3,4-B]indoles 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 |
| US9034865B2 (en) | 2010-02-18 | 2015-05-19 | Medivation Technologies, Inc. | Pyrido [4,3-B] indole and pyrido [3,4-B] indole derivatives and methods of use |
| WO2011103485A1 (en) | 2010-02-18 | 2011-08-25 | Medivation Technologies, Inc. | Fused tetracyclic 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 |
| 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 |
| WO2012006419A2 (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 |
| 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 |
| US8791132B2 (en) | 2011-02-18 | 2014-07-29 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| WO2014031170A1 (en) * | 2012-08-22 | 2014-02-27 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
| WO2014031165A1 (en) * | 2012-08-22 | 2014-02-27 | Medivation Technologies, Inc. | Compounds and methods of treating diabetes |
| EP2925129A4 (en) * | 2012-08-24 | 2016-06-08 | Univ Texas | PRO-NEUROGENIC COMPOUNDS |
| WO2015070234A2 (en) | 2013-11-11 | 2015-05-14 | Board Of Regents Of The University Of Texas System | Neuroprotective compounds and use thereof |
| WO2016037106A1 (en) | 2014-09-05 | 2016-03-10 | Allosteros Therapeutics, Inc | CaMKII INHIBITORS AND USES THEREOF |
| WO2020037155A1 (en) | 2018-08-16 | 2020-02-20 | Recreo Pharmaceuticals Llc | 1,3,4,9-tetrahydro-2h-pyrido[3,4-b]indole derivative compounds and uses thereof |
| US12357619B2 (en) | 2020-03-19 | 2025-07-15 | Alla Chem Llc | Noradrenergic and specific serotonergic anxiolytic and antidepressant, method for the production and use thereof |
| US12016847B2 (en) | 2021-03-12 | 2024-06-25 | Bristol-Myers Squibb Company | Methods of treating prostate cancer |
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2009
- 2009-10-30 CA CA2742320A patent/CA2742320A1/en not_active Abandoned
- 2009-10-30 EP EP09824199A patent/EP2346332A4/en not_active Withdrawn
- 2009-10-30 TW TW098137048A patent/TWI477503B/zh not_active IP Right Cessation
- 2009-10-30 CN CN200980153434.2A patent/CN102271508B/zh not_active Expired - Fee Related
- 2009-10-30 US US12/610,217 patent/US8907097B2/en not_active Expired - Fee Related
- 2009-10-30 BR BRPI0919948-9A patent/BRPI0919948A2/pt not_active IP Right Cessation
- 2009-10-30 JP JP2011534826A patent/JP5588991B2/ja not_active Expired - Fee Related
- 2009-10-30 WO PCT/US2009/062869 patent/WO2010051501A1/en not_active Ceased
- 2009-10-30 AR ARP090104220A patent/AR073923A1/es unknown
- 2009-10-30 AU AU2009308706A patent/AU2009308706C1/en not_active Ceased
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2013
- 2013-03-08 US US13/791,544 patent/US8906925B2/en not_active Expired - Fee Related
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2014
- 2014-04-21 JP JP2014087277A patent/JP2014133759A/ja not_active Withdrawn
- 2014-11-03 US US14/531,915 patent/US9458155B2/en not_active Expired - Fee Related