RU2417225C2 - Индазолы, бензотиазолы, бензоизотиазолы, бензизоксазолы и их получение и применение - Google Patents
Индазолы, бензотиазолы, бензоизотиазолы, бензизоксазолы и их получение и применение Download PDFInfo
- Publication number
- RU2417225C2 RU2417225C2 RU2006137472/04A RU2006137472A RU2417225C2 RU 2417225 C2 RU2417225 C2 RU 2417225C2 RU 2006137472/04 A RU2006137472/04 A RU 2006137472/04A RU 2006137472 A RU2006137472 A RU 2006137472A RU 2417225 C2 RU2417225 C2 RU 2417225C2
- Authority
- RU
- Russia
- Prior art keywords
- azabicyclo
- oct
- indazole
- carboxamide
- carbon atoms
- Prior art date
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- -1 bentothiazoles Chemical class 0.000 title claims 12
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title 1
- 150000008316 benzisoxazoles Chemical class 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 150000002473 indoazoles Chemical class 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 91
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 70
- 125000000217 alkyl group Chemical group 0.000 claims abstract 33
- 150000003839 salts Chemical class 0.000 claims abstract 26
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 11
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 10
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims abstract 8
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims abstract 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 5
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 4
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims abstract 4
- 230000000694 effects Effects 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract 4
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract 4
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract 4
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims abstract 3
- 239000003446 ligand Substances 0.000 claims abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract 2
- 125000003971 isoxazolinyl group Chemical group 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract 2
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims abstract 2
- 239000003814 drug Substances 0.000 claims 18
- 238000011282 treatment Methods 0.000 claims 13
- 206010012289 Dementia Diseases 0.000 claims 6
- 208000010877 cognitive disease Diseases 0.000 claims 6
- 206010027175 memory impairment Diseases 0.000 claims 5
- 208000000044 Amnesia Diseases 0.000 claims 4
- 208000028698 Cognitive impairment Diseases 0.000 claims 4
- DNNLVYLDOAZDKN-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-(1,3-thiazol-2-yl)-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2C1=NC=CS1 DNNLVYLDOAZDKN-HNNXBMFYSA-N 0.000 claims 4
- BAJXGRSDFUMTTO-CYBMUJFWSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-(trifluoromethoxy)-1h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NNC2=CC=C(OC(F)(F)F)C=C21 BAJXGRSDFUMTTO-CYBMUJFWSA-N 0.000 claims 4
- 230000001575 pathological effect Effects 0.000 claims 4
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- WMCJBRAWOZRWGI-ZDUSSCGKSA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-6-hydroxy-1H-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NNC2=CC(O)=CC=C21 WMCJBRAWOZRWGI-ZDUSSCGKSA-N 0.000 claims 3
- 230000004913 activation Effects 0.000 claims 3
- 230000006984 memory degeneration Effects 0.000 claims 3
- 208000023060 memory loss Diseases 0.000 claims 3
- ACNNVXKERMJQRY-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(1,3-thiazol-2-yl)-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C1=NC=CS1 ACNNVXKERMJQRY-HNNXBMFYSA-N 0.000 claims 3
- BAJXGRSDFUMTTO-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(trifluoromethoxy)-1h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NNC2=CC=C(OC(F)(F)F)C=C21 BAJXGRSDFUMTTO-ZDUSSCGKSA-N 0.000 claims 3
- BMQBMQFHTPBOBT-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-cyano-1h-indazole-3-carboxamide Chemical compound C1=C(C#N)C=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=NNC2=C1 BMQBMQFHTPBOBT-AWEZNQCLSA-N 0.000 claims 3
- SJAQTRZWNSMCLZ-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-hydroxy-1h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NNC2=CC=C(O)C=C21 SJAQTRZWNSMCLZ-ZDUSSCGKSA-N 0.000 claims 3
- CYUBVTKBHKHYEQ-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-methoxy-1h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NNC2=CC=C(OC)C=C21 CYUBVTKBHKHYEQ-AWEZNQCLSA-N 0.000 claims 3
- PDYXITUQEAWCJS-SFHVURJKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-piperidin-1-yl-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2N1CCCCC1 PDYXITUQEAWCJS-SFHVURJKSA-N 0.000 claims 3
- PQLZUYZNOVJHOX-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-(1-methylimidazol-2-yl)-1h-indazole-3-carboxamide Chemical compound CN1C=CN=C1C1=CC=C(C(=NN2)C(=O)N[C@@H]3C4CCN(CC4)C3)C2=C1 PQLZUYZNOVJHOX-INIZCTEOSA-N 0.000 claims 3
- URJRGCNBYUZPLW-SFHVURJKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-(3,6-dihydro-2h-pyran-4-yl)-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2C1=CCOCC1 URJRGCNBYUZPLW-SFHVURJKSA-N 0.000 claims 3
- XIYQUORHPQHVQN-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-cyano-1h-indazole-3-carboxamide Chemical compound N#CC1=CC=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=NNC2=C1 XIYQUORHPQHVQN-AWEZNQCLSA-N 0.000 claims 3
- ACNNVXKERMJQRY-OAHLLOKOSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-(1,3-thiazol-2-yl)-1h-indazole-3-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C1=NC=CS1 ACNNVXKERMJQRY-OAHLLOKOSA-N 0.000 claims 3
- BMQBMQFHTPBOBT-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-cyano-1h-indazole-3-carboxamide Chemical compound C1=C(C#N)C=C2C(C(N[C@H]3C4CCN(CC4)C3)=O)=NNC2=C1 BMQBMQFHTPBOBT-CQSZACIVSA-N 0.000 claims 3
- CYUBVTKBHKHYEQ-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-methoxy-1h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NNC2=CC=C(OC)C=C21 CYUBVTKBHKHYEQ-CQSZACIVSA-N 0.000 claims 3
- DNNLVYLDOAZDKN-OAHLLOKOSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(1,3-thiazol-2-yl)-1h-indazole-3-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2C1=NC=CS1 DNNLVYLDOAZDKN-OAHLLOKOSA-N 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
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- GXXHINQJSXGKMJ-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(1,3-oxazol-2-yl)-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C1=NC=CO1 GXXHINQJSXGKMJ-HNNXBMFYSA-N 0.000 claims 2
- LTBCACIRLQIDPD-IBGZPJMESA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(cyclohexen-1-yl)-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C1=CCCCC1 LTBCACIRLQIDPD-IBGZPJMESA-N 0.000 claims 2
- OICNDHYOFLQFCV-SFHVURJKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(oxan-4-yl)-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C1CCOCC1 OICNDHYOFLQFCV-SFHVURJKSA-N 0.000 claims 2
- KJULPOILUGHJEX-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-ethynyl-1h-indazole-3-carboxamide Chemical compound C1=C(C#C)C=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=NNC2=C1 KJULPOILUGHJEX-HNNXBMFYSA-N 0.000 claims 2
- RMHCVPSLCOLOQE-IBGZPJMESA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-phenoxy-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2OC1=CC=CC=C1 RMHCVPSLCOLOQE-IBGZPJMESA-N 0.000 claims 2
- LMFXLOSPHRQRAD-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyrrolidin-1-yl-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2N1CCCC1 LMFXLOSPHRQRAD-KRWDZBQOSA-N 0.000 claims 2
- PWHPQTFXMPANAS-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-(1,3-oxazol-2-yl)-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2C1=NC=CO1 PWHPQTFXMPANAS-HNNXBMFYSA-N 0.000 claims 2
- ZFHJKWVOLRJASD-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-ethynyl-1h-indazole-3-carboxamide Chemical compound C#CC1=CC=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=NNC2=C1 ZFHJKWVOLRJASD-HNNXBMFYSA-N 0.000 claims 2
- RKEIUKWUQDIZFV-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-methoxy-1h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NNC2=CC(OC)=CC=C21 RKEIUKWUQDIZFV-AWEZNQCLSA-N 0.000 claims 2
- FARLLDXBOZAKTC-SFHVURJKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-pent-1-ynyl-1h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NNC2=CC(C#CCCC)=CC=C21 FARLLDXBOZAKTC-SFHVURJKSA-N 0.000 claims 2
- XKRFIYFJYZVHKA-SFHVURJKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-piperidin-1-yl-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2N1CCCCC1 XKRFIYFJYZVHKA-SFHVURJKSA-N 0.000 claims 2
- YUHAPKIULYTVCM-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-pyrrolidin-1-yl-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2N1CCCC1 YUHAPKIULYTVCM-KRWDZBQOSA-N 0.000 claims 2
- GXXHINQJSXGKMJ-OAHLLOKOSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-(1,3-oxazol-2-yl)-1h-indazole-3-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C1=NC=CO1 GXXHINQJSXGKMJ-OAHLLOKOSA-N 0.000 claims 2
- OICNDHYOFLQFCV-GOSISDBHSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-(oxan-4-yl)-1h-indazole-3-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C1CCOCC1 OICNDHYOFLQFCV-GOSISDBHSA-N 0.000 claims 2
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- PWHPQTFXMPANAS-OAHLLOKOSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(1,3-oxazol-2-yl)-1h-indazole-3-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2C1=NC=CO1 PWHPQTFXMPANAS-OAHLLOKOSA-N 0.000 claims 2
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2005
- 2005-03-25 EP EP05745169A patent/EP1735306A2/en not_active Withdrawn
- 2005-03-25 CN CN201310692588.7A patent/CN103724343A/zh active Pending
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- 2005-03-25 BR BRPI0508771-6A patent/BRPI0508771A/pt not_active IP Right Cessation
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- 2005-03-25 JP JP2007505233A patent/JP4995075B2/ja not_active Expired - Fee Related
- 2005-03-25 AU AU2005227324A patent/AU2005227324A1/en not_active Abandoned
- 2005-03-25 KR KR1020067022085A patent/KR101176670B1/ko not_active Expired - Fee Related
- 2005-03-25 WO PCT/US2005/010120 patent/WO2005092890A2/en not_active Ceased
- 2005-03-25 SG SG200902028-0A patent/SG165199A1/en unknown
- 2005-03-25 RU RU2006137472/04A patent/RU2417225C2/ru not_active IP Right Cessation
- 2005-03-25 US US11/089,533 patent/US20050234095A1/en not_active Abandoned
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- 2006-09-19 IL IL178188A patent/IL178188A/en not_active IP Right Cessation
- 2006-10-20 MA MA29406A patent/MA28972B1/fr unknown
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- 2006-10-24 NO NO20064826A patent/NO20064826L/no not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2005092890A3 (en) | 2006-02-02 |
| IL218692A0 (en) | 2012-05-31 |
| CR8711A (es) | 2007-08-28 |
| EP2336128A1 (en) | 2011-06-22 |
| AU2005227324A1 (en) | 2005-10-06 |
| CA2560741A1 (en) | 2005-10-06 |
| IL178188A0 (en) | 2006-12-31 |
| NO20064826L (no) | 2006-12-20 |
| IL178188A (en) | 2012-10-31 |
| BRPI0508771A (pt) | 2007-08-14 |
| US20050234095A1 (en) | 2005-10-20 |
| US8263619B2 (en) | 2012-09-11 |
| JP2011252002A (ja) | 2011-12-15 |
| JP2007530590A (ja) | 2007-11-01 |
| US20130217683A1 (en) | 2013-08-22 |
| ECSP066951A (es) | 2006-12-20 |
| US20100105677A1 (en) | 2010-04-29 |
| KR20070015406A (ko) | 2007-02-02 |
| JP4995075B2 (ja) | 2012-08-08 |
| EP1735306A2 (en) | 2006-12-27 |
| MXPA06010852A (es) | 2007-01-16 |
| CA2560741C (en) | 2013-08-06 |
| MA28972B1 (fr) | 2007-11-01 |
| CN103724343A (zh) | 2014-04-16 |
| US20110319407A1 (en) | 2011-12-29 |
| US8486937B2 (en) | 2013-07-16 |
| WO2005092890A2 (en) | 2005-10-06 |
| SG165199A1 (en) | 2010-10-28 |
| KR101176670B1 (ko) | 2012-08-23 |
| US8691841B2 (en) | 2014-04-08 |
| RU2006137472A (ru) | 2008-04-27 |
| CR20120010A (es) | 2012-02-13 |
| NZ550534A (en) | 2009-07-31 |
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