JP5240941B2 - Ｐ２ｘ７調節因子としてのビシクロへテロアリール化合物およびその使用 - Google Patents
Ｐ２ｘ７調節因子としてのビシクロへテロアリール化合物およびその使用 Download PDFInfo
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- JP5240941B2 JP5240941B2 JP2009500521A JP2009500521A JP5240941B2 JP 5240941 B2 JP5240941 B2 JP 5240941B2 JP 2009500521 A JP2009500521 A JP 2009500521A JP 2009500521 A JP2009500521 A JP 2009500521A JP 5240941 B2 JP5240941 B2 JP 5240941B2
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- Prior art keywords
- oxo
- isoquinolin
- dihydro
- hydroxy
- phenyl
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- PMJXNWPUMRXYGK-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-n-[2-(2-hydroxyethyl)-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1=CC=C2C(=O)N(CCO)C=CC2=C1NC(=O)CC1=CC=C(F)C(Cl)=C1 PMJXNWPUMRXYGK-UHFFFAOYSA-N 0.000 claims 1
- VEHSOQCTZZUPOB-GFCCVEGCSA-N 2-(3-chloro-4-fluorophenyl)-n-[2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(F)C(Cl)=C1 VEHSOQCTZZUPOB-GFCCVEGCSA-N 0.000 claims 1
- VEHSOQCTZZUPOB-LBPRGKRZSA-N 2-(3-chloro-4-fluorophenyl)-n-[2-[(2s)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1=CC=C2C(=O)N([C@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(F)C(Cl)=C1 VEHSOQCTZZUPOB-LBPRGKRZSA-N 0.000 claims 1
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- MUBSUNWSXCIFPI-GFCCVEGCSA-N 2-(4-chloro-2-fluorophenyl)-n-[2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C=C1F MUBSUNWSXCIFPI-GFCCVEGCSA-N 0.000 claims 1
- BUCKXRYOPVRRMW-UHFFFAOYSA-N 2-(4-chloro-3-fluorophenyl)-n-[2-(1-hydroxy-2-methylpropan-2-yl)-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1=CC=C2C(=O)N(C(C)(CO)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C(F)=C1 BUCKXRYOPVRRMW-UHFFFAOYSA-N 0.000 claims 1
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- UFSZNGPKJWFSHR-CYBMUJFWSA-N 2-(4-chloro-3-fluorophenyl)-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C(F)=C1 UFSZNGPKJWFSHR-CYBMUJFWSA-N 0.000 claims 1
- LHSCZMRBDSGDQW-LBPRGKRZSA-N 2-(4-chloro-3-fluorophenyl)-n-[2-[(2s)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1=CC=C2C(=O)N([C@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C(F)=C1 LHSCZMRBDSGDQW-LBPRGKRZSA-N 0.000 claims 1
- NNKBOZOTRMTPFO-LLVKDONJSA-N 2-(4-chloro-3-fluorophenyl)-n-[6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C(F)=C1 NNKBOZOTRMTPFO-LLVKDONJSA-N 0.000 claims 1
- XKKXIJIKSKGNDK-KPMSDPLLSA-N 2-(4-chlorophenyl)-n-[1-oxo-2-[[(2r)-pyrrolidin-2-yl]methyl]isoquinolin-5-yl]propanamide Chemical compound C=1C=C(Cl)C=CC=1C(C)C(=O)NC1=CC=CC(C2=O)=C1C=CN2C[C@H]1CCCN1 XKKXIJIKSKGNDK-KPMSDPLLSA-N 0.000 claims 1
- XKKXIJIKSKGNDK-PKHIMPSTSA-N 2-(4-chlorophenyl)-n-[1-oxo-2-[[(2s)-pyrrolidin-2-yl]methyl]isoquinolin-5-yl]propanamide Chemical compound C=1C=C(Cl)C=CC=1C(C)C(=O)NC1=CC=CC(C2=O)=C1C=CN2C[C@@H]1CCCN1 XKKXIJIKSKGNDK-PKHIMPSTSA-N 0.000 claims 1
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- UMNZJXXHDVHFNE-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[2-(2-hydroxyethyl)-1-oxoisoquinolin-5-yl]propanamide Chemical compound C=1C=CC(C(N(CCO)C=C2)=O)=C2C=1NC(=O)C(C)C1=CC=C(Cl)C=C1 UMNZJXXHDVHFNE-UHFFFAOYSA-N 0.000 claims 1
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- WBYJNDMJZGFXFL-GFCCVEGCSA-N 2-[2,4-bis(trifluoromethyl)phenyl]-n-[2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1C(F)(F)F WBYJNDMJZGFXFL-GFCCVEGCSA-N 0.000 claims 1
- OATNOQBYVOVZJE-UHFFFAOYSA-N 2-[2,5-bis(trifluoromethyl)phenyl]-n-[2-(2-hydroxyethyl)-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1=CC=C2C(=O)N(CCO)C=CC2=C1NC(=O)CC1=CC(C(F)(F)F)=CC=C1C(F)(F)F OATNOQBYVOVZJE-UHFFFAOYSA-N 0.000 claims 1
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- VSGLANORJMNZRC-CYBMUJFWSA-N 2-[2-fluoro-3-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1F VSGLANORJMNZRC-CYBMUJFWSA-N 0.000 claims 1
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- HKGHKWAHPXKDNF-OAHLLOKOSA-N 2-[4-chloro-3-(trifluoromethyl)phenyl]-n-[1-oxo-2-[[(2r)-pyrrolidin-2-yl]methyl]isoquinolin-5-yl]acetamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(CC(=O)NC=2C3=C(C(N(C[C@@H]4NCCC4)C=C3)=O)C=CC=2)=C1 HKGHKWAHPXKDNF-OAHLLOKOSA-N 0.000 claims 1
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- XHTRUFHCZQQMOM-GFCCVEGCSA-N 2-[4-chloro-3-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C(C(F)(F)F)=C1 XHTRUFHCZQQMOM-GFCCVEGCSA-N 0.000 claims 1
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- ZFESFSVNBNRVFO-GFCCVEGCSA-N 2-[4-fluoro-3-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(F)C(C(F)(F)F)=C1 ZFESFSVNBNRVFO-GFCCVEGCSA-N 0.000 claims 1
- UTSFTJWRTXSFSI-CYBMUJFWSA-N 2-[4-fluoro-3-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(F)C(C(F)(F)F)=C1 UTSFTJWRTXSFSI-CYBMUJFWSA-N 0.000 claims 1
- ZFESFSVNBNRVFO-LBPRGKRZSA-N 2-[4-fluoro-3-(trifluoromethyl)phenyl]-n-[2-[(2s)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1=CC=C2C(=O)N([C@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(F)C(C(F)(F)F)=C1 ZFESFSVNBNRVFO-LBPRGKRZSA-N 0.000 claims 1
- DNGBWHSPBDNOKD-UHFFFAOYSA-N 2-[5-chloro-2-(trifluoromethyl)phenyl]-n-[2-(2-hydroxyethyl)-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1=CC=C2C(=O)N(CCO)C=CC2=C1NC(=O)CC1=CC(Cl)=CC=C1C(F)(F)F DNGBWHSPBDNOKD-UHFFFAOYSA-N 0.000 claims 1
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- WIVVTASCOMNZJL-UHFFFAOYSA-N 2-chloro-n-[2-(1-hydroxypropan-2-yl)-1-oxoisoquinolin-5-yl]benzamide Chemical compound C1=CC=C2C(=O)N(C(CO)C)C=CC2=C1NC(=O)C1=CC=CC=C1Cl WIVVTASCOMNZJL-UHFFFAOYSA-N 0.000 claims 1
- AMFOSJXVADGGME-UHFFFAOYSA-N 2-chloro-n-[2-(2-hydroxy-2-methylpropyl)-1-oxoisoquinolin-5-yl]benzamide Chemical compound C1=CC=C2C(=O)N(CC(C)(O)C)C=CC2=C1NC(=O)C1=CC=CC=C1Cl AMFOSJXVADGGME-UHFFFAOYSA-N 0.000 claims 1
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- ITOLDJHTYYVNBX-UHFFFAOYSA-N 2-chloro-n-[2-(2-hydroxypropyl)-1-oxoisoquinolin-5-yl]benzamide Chemical compound C1=CC=C2C(=O)N(CC(O)C)C=CC2=C1NC(=O)C1=CC=CC=C1Cl ITOLDJHTYYVNBX-UHFFFAOYSA-N 0.000 claims 1
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- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
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| US10155742B2 (en) | 2012-01-13 | 2018-12-18 | President And Fellows Of Harvard College | Halofuginol derivatives and their use in cosmetic and pharmaceutical compositions |
| US9409917B2 (en) | 2012-01-20 | 2016-08-09 | Actelion Pharmaceuticals Ltd. | Heterocyclic amide derivatives as P2X7 receptor antagonists |
| WO2014091415A1 (en) | 2012-12-12 | 2014-06-19 | Actelion Pharmaceuticals Ltd | Indole carboxamide derivatives as p2x7 receptor antagonists |
| KR102232744B1 (ko) | 2012-12-18 | 2021-03-26 | 이도르시아 파마슈티컬스 리미티드 | Ｐ２ｘ７ 수용체 길항제로서의 인돌 카르복사미드 유도체 |
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| ES2616883T3 (es) | 2013-01-22 | 2017-06-14 | Actelion Pharmaceuticals Ltd. | Derivados amida heterocíclicos como antagonistas del receptor P2X7 |
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| WO2019099509A1 (en) * | 2017-11-14 | 2019-05-23 | Second Genome, Inc. | Use of a p2x7 receptor antagonist to treat an inflammatory disease or disorder |
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| IL302906A (en) * | 2020-11-20 | 2023-07-01 | Denali Therapeutics Inc | Compounds, compositions, and methods |
| TWI825637B (zh) | 2021-03-31 | 2023-12-11 | 美商輝瑞股份有限公司 | 啶－１，６（２ｈ，７ｈ）－二酮 |
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- 2007-03-16 CA CA2645568A patent/CA2645568C/en not_active Expired - Fee Related
- 2007-03-16 US US11/725,153 patent/US7816371B2/en not_active Expired - Fee Related
- 2007-03-16 DK DK07753368.5T patent/DK1933622T3/en active
- 2007-03-16 CN CN2007800170265A patent/CN101442909B/zh active Active
- 2007-03-16 ES ES07753368.5T patent/ES2569352T3/es active Active
- 2007-03-16 AR ARP070101082A patent/AR059920A1/es not_active Application Discontinuation
-
2010
- 2010-10-18 US US12/925,297 patent/US20110092476A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2645568A1 (en) | 2007-09-27 |
| MX2008011922A (es) | 2008-11-28 |
| US7816371B2 (en) | 2010-10-19 |
| BRPI0709581A8 (pt) | 2018-12-11 |
| CA2645568C (en) | 2014-11-18 |
| DK1933622T3 (en) | 2016-05-02 |
| JP2009530304A (ja) | 2009-08-27 |
| EP1933622A4 (en) | 2010-03-10 |
| ES2569352T3 (es) | 2016-05-10 |
| CN101442909A (zh) | 2009-05-27 |
| TWI464148B (zh) | 2014-12-11 |
| CN101442909B (zh) | 2013-03-27 |
| WO2007109192A3 (en) | 2007-11-22 |
| EP1933622A2 (en) | 2008-06-25 |
| TW200800904A (en) | 2008-01-01 |
| US20110092476A1 (en) | 2011-04-21 |
| US20070225324A1 (en) | 2007-09-27 |
| AR059920A1 (es) | 2008-05-07 |
| BRPI0709581A2 (pt) | 2011-07-19 |
| EP1933622B1 (en) | 2016-03-09 |
| HK1133787A1 (en) | 2010-04-09 |
| WO2007109192A2 (en) | 2007-09-27 |
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