JP2013532146A5 - - Google Patents
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- Publication number
- JP2013532146A5 JP2013532146A5 JP2013514676A JP2013514676A JP2013532146A5 JP 2013532146 A5 JP2013532146 A5 JP 2013532146A5 JP 2013514676 A JP2013514676 A JP 2013514676A JP 2013514676 A JP2013514676 A JP 2013514676A JP 2013532146 A5 JP2013532146 A5 JP 2013532146A5
- Authority
- JP
- Japan
- Prior art keywords
- chromeno
- dihydro
- oxo
- pyrrol
- compound according
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 34
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 125000004432 carbon atom Chemical group C* 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 208000030159 metabolic disease Diseases 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 150000002148 esters Chemical class 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical group 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- -1 —CH 2 -aryl Chemical group 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 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 4
- 208000016097 disease of metabolism Diseases 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000034 thioazolyl group Chemical group 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 102000030595 Glucokinase Human genes 0.000 claims 2
- 108010021582 Glucokinase Proteins 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- YCPFQYGGDDPZBJ-ZDUSSCGKSA-N (2s)-2-(5,8-dimethoxy-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-4-methylpentanoic acid Chemical compound C1C=2C(OC)=CC=C(OC)C=2OC2=C1CN([C@@H](CC(C)C)C(O)=O)C2=O YCPFQYGGDDPZBJ-ZDUSSCGKSA-N 0.000 claims 1
- ZGQKUSRLSNZSAZ-SFHVURJKSA-N (2s)-2-(5-chloro-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-3-cyclohexyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound C([C@H](N1C(=O)C2=C(C1)CC=1C=CC=C(C=1O2)Cl)C(=O)NC=1SC=CN=1)C1CCCCC1 ZGQKUSRLSNZSAZ-SFHVURJKSA-N 0.000 claims 1
- DDWDSGPCZOUOIV-FQEVSTJZSA-N (2s)-2-(5-chloro-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-3-cyclohexyl-n-pyridin-2-ylpropanamide Chemical compound C([C@H](N1C(=O)C2=C(C1)CC=1C=CC=C(C=1O2)Cl)C(=O)NC=1N=CC=CC=1)C1CCCCC1 DDWDSGPCZOUOIV-FQEVSTJZSA-N 0.000 claims 1
- GAUIONMVLNGSKI-HNNXBMFYSA-N (2s)-2-(5-chloro-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-4-methyl-n-(1,3-thiazol-2-yl)pentanamide Chemical compound O=C([C@@H](N1C(C2=C(CC3=CC=CC(Cl)=C3O2)C1)=O)CC(C)C)NC1=NC=CS1 GAUIONMVLNGSKI-HNNXBMFYSA-N 0.000 claims 1
- YWKFGOWRGVXVRX-KRWDZBQOSA-N (2s)-2-(5-chloro-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-4-methyl-n-pyridin-2-ylpentanamide Chemical compound O=C([C@@H](N1C(C2=C(CC3=CC=CC(Cl)=C3O2)C1)=O)CC(C)C)NC1=CC=CC=N1 YWKFGOWRGVXVRX-KRWDZBQOSA-N 0.000 claims 1
- KODSXHNGZNXMHC-SFHVURJKSA-N (2s)-2-(8-chloro-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-3-cyclohexyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound C([C@H](N1CC2=C(C1=O)OC=1C=CC=C(C=1C2)Cl)C(=O)NC=1SC=CN=1)C1CCCCC1 KODSXHNGZNXMHC-SFHVURJKSA-N 0.000 claims 1
- WEEKKOREMIGRDV-FQEVSTJZSA-N (2s)-2-(8-chloro-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-3-cyclohexyl-n-pyridin-2-ylpropanamide Chemical compound C([C@H](N1CC2=C(C1=O)OC=1C=CC=C(C=1C2)Cl)C(=O)NC=1N=CC=CC=1)C1CCCCC1 WEEKKOREMIGRDV-FQEVSTJZSA-N 0.000 claims 1
- GXNPIVLAMAOIGX-HNNXBMFYSA-N (2s)-2-(8-chloro-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-4-methyl-n-(1,3-thiazol-2-yl)pentanamide Chemical compound O=C([C@@H](N1C(C2=C(CC3=C(Cl)C=CC=C3O2)C1)=O)CC(C)C)NC1=NC=CS1 GXNPIVLAMAOIGX-HNNXBMFYSA-N 0.000 claims 1
- FNNWHXSUOJRBJO-KRWDZBQOSA-N (2s)-2-(8-chloro-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-4-methyl-n-pyridin-2-ylpentanamide Chemical compound O=C([C@@H](N1C(C2=C(CC3=C(Cl)C=CC=C3O2)C1)=O)CC(C)C)NC1=CC=CC=N1 FNNWHXSUOJRBJO-KRWDZBQOSA-N 0.000 claims 1
- ZFITUKKMKFQVOV-HNNXBMFYSA-N (2s)-2-(8-methoxy-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-4-methyl-n-(1,3-thiazol-2-yl)pentanamide Chemical compound O=C([C@H](CC(C)C)N1CC2=C(C1=O)OC=1C=CC=C(C=1C2)OC)NC1=NC=CS1 ZFITUKKMKFQVOV-HNNXBMFYSA-N 0.000 claims 1
- XRHQBOSYMFERIZ-SFHVURJKSA-N (2s)-3-cyclohexyl-2-(5,8-dimethoxy-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C([C@H](N1CC2=C(C1=O)OC=1C(OC)=CC=C(C=1C2)OC)C(=O)NC=1SC=CN=1)C1CCCCC1 XRHQBOSYMFERIZ-SFHVURJKSA-N 0.000 claims 1
- ZBTKODPNXRFMSF-FQEVSTJZSA-N (2s)-3-cyclohexyl-2-(5,8-dimethoxy-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-n-pyridin-2-ylpropanamide Chemical compound C([C@H](N1CC2=C(C1=O)OC=1C(OC)=CC=C(C=1C2)OC)C(=O)NC=1N=CC=CC=1)C1CCCCC1 ZBTKODPNXRFMSF-FQEVSTJZSA-N 0.000 claims 1
- OREFYHQAZOLNIE-SFHVURJKSA-N (2s)-3-cyclohexyl-2-(8-methoxy-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C([C@H](N1CC2=C(C1=O)OC=1C=CC=C(C=1C2)OC)C(=O)NC=1SC=CN=1)C1CCCCC1 OREFYHQAZOLNIE-SFHVURJKSA-N 0.000 claims 1
- UTYJLKOOXXNAFD-FQEVSTJZSA-N (2s)-3-cyclohexyl-2-(8-methoxy-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-n-pyridin-2-ylpropanamide Chemical compound C([C@H](N1CC2=C(C1=O)OC=1C=CC=C(C=1C2)OC)C(=O)NC=1N=CC=CC=1)C1CCCCC1 UTYJLKOOXXNAFD-FQEVSTJZSA-N 0.000 claims 1
- UCLWFNCLGOWCAZ-CTNGQTDRSA-N (2s)-3-cyclohexyl-n-[1-[(2r)-2,3-dihydroxypropyl]pyrazol-3-yl]-2-(8-methoxy-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)propanamide Chemical compound C([C@H](N1CC2=C(C1=O)OC=1C=CC=C(C=1C2)OC)C(=O)NC1=NN(C[C@@H](O)CO)C=C1)C1CCCCC1 UCLWFNCLGOWCAZ-CTNGQTDRSA-N 0.000 claims 1
- CGSWQZWTNQZWNF-KRWDZBQOSA-N (2s)-n-(5-chloropyridin-2-yl)-2-(5,8-dimethoxy-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-4-methylpentanamide Chemical compound O=C([C@H](CC(C)C)N1CC2=C(C1=O)OC=1C(OC)=CC=C(C=1C2)OC)NC1=CC=C(Cl)C=N1 CGSWQZWTNQZWNF-KRWDZBQOSA-N 0.000 claims 1
- QSWSHRPPPUYIDY-FQEVSTJZSA-N (2s)-n-(5-chloropyridin-2-yl)-3-cyclohexyl-2-(5,8-dimethoxy-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)propanamide Chemical compound C([C@H](N1CC2=C(C1=O)OC=1C(OC)=CC=C(C=1C2)OC)C(=O)NC=1N=CC(Cl)=CC=1)C1CCCCC1 QSWSHRPPPUYIDY-FQEVSTJZSA-N 0.000 claims 1
- SOGPQIDCJBQCHY-FQEVSTJZSA-N (2s)-n-(5-chloropyridin-2-yl)-3-cyclohexyl-2-(8-methoxy-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)propanamide Chemical compound C([C@H](N1CC2=C(C1=O)OC=1C=CC=C(C=1C2)OC)C(=O)NC=1N=CC(Cl)=CC=1)C1CCCCC1 SOGPQIDCJBQCHY-FQEVSTJZSA-N 0.000 claims 1
- BTGVPOVWLNJLLA-ZOWNYOTGSA-N ClC=1C=CC=NC1.ClC=1C=2CC3=C(C(N(C3)[C@H](C(=O)O)CC(C)C)=O)OC2C=CC1 Chemical compound ClC=1C=CC=NC1.ClC=1C=2CC3=C(C(N(C3)[C@H](C(=O)O)CC(C)C)=O)OC2C=CC1 BTGVPOVWLNJLLA-ZOWNYOTGSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- USWJTLZIOPWSHR-SFHVURJKSA-N methyl 6-[[(2s)-2-(5,8-dimethoxy-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-4-methylpentanoyl]amino]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1NC(=O)[C@H](CC(C)C)N1C(=O)C(OC=2C(=C(OC)C=CC=2OC)C2)=C2C1 USWJTLZIOPWSHR-SFHVURJKSA-N 0.000 claims 1
- MPRPQSTVKHBSFO-SFHVURJKSA-N methyl 6-[[(2s)-2-(5-chloro-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-4-methylpentanoyl]amino]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1NC(=O)[C@H](CC(C)C)N1C(=O)C(OC=2C(=CC=CC=2Cl)C2)=C2C1 MPRPQSTVKHBSFO-SFHVURJKSA-N 0.000 claims 1
- FWJOQFXGWHNWCK-SFHVURJKSA-N methyl 6-[[(2s)-2-(8-chloro-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-4-methylpentanoyl]amino]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1NC(=O)[C@H](CC(C)C)N1C(=O)C(OC=2C(=C(Cl)C=CC=2)C2)=C2C1 FWJOQFXGWHNWCK-SFHVURJKSA-N 0.000 claims 1
- AUQLZCWIYJYNOE-SFHVURJKSA-N methyl 6-[[(2s)-2-(8-methoxy-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)-4-methylpentanoyl]amino]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1NC(=O)[C@H](CC(C)C)N1C(=O)C(OC=2C(=C(OC)C=CC=2)C2)=C2C1 AUQLZCWIYJYNOE-SFHVURJKSA-N 0.000 claims 1
- IKMJOSYSAQJYKR-NRFANRHFSA-N methyl 6-[[(2s)-3-cyclohexyl-2-(5,8-dimethoxy-3-oxo-1,9-dihydrochromeno[2,3-c]pyrrol-2-yl)propanoyl]amino]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1NC(=O)[C@@H](N1C(C2=C(CC3=C(OC)C=CC(OC)=C3O2)C1)=O)CC1CCCCC1 IKMJOSYSAQJYKR-NRFANRHFSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 0 Cc1ccc(*)c2c1OC(C(N(C1)C(C*)C(N*)=O)=O)=C1C2 Chemical compound Cc1ccc(*)c2c1OC(C(N(C1)C(C*)C(N*)=O)=O)=C1C2 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35561910P | 2010-06-17 | 2010-06-17 | |
| US61/355,619 | 2010-06-17 | ||
| PCT/EP2011/059783 WO2011157682A1 (en) | 2010-06-17 | 2011-06-14 | 3-oxo-3,9-dihydro-1h-chromeno[2,3-c]pyrroles as glucokinase activators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013532146A JP2013532146A (ja) | 2013-08-15 |
| JP2013532146A5 true JP2013532146A5 (https=) | 2014-07-31 |
| JP5844355B2 JP5844355B2 (ja) | 2016-01-13 |
Family
ID=44266428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013514676A Expired - Fee Related JP5844355B2 (ja) | 2010-06-17 | 2011-06-14 | グルコキナーゼ活性剤としての３−オキソ−３，９−ジヒドロ−１Ｈ−クロメノ［２，３−ｃ］ピロール |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8178689B2 (https=) |
| EP (1) | EP2582706A1 (https=) |
| JP (1) | JP5844355B2 (https=) |
| KR (1) | KR20130120993A (https=) |
| CN (1) | CN102947311B (https=) |
| BR (1) | BR112012032235A2 (https=) |
| CA (1) | CA2801168A1 (https=) |
| MX (1) | MX2012010668A (https=) |
| RU (1) | RU2603191C2 (https=) |
| WO (1) | WO2011157682A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2938609T3 (pl) * | 2012-12-25 | 2017-08-31 | Hua Medicine | Sposób wytwarzania 1-([1,3]dioksolan-4-ylometylo)-1h-pirazol-3- iloaminy |
| GB201714777D0 (en) | 2017-09-14 | 2017-11-01 | Univ London Queen Mary | Agent |
| CN112888480A (zh) * | 2018-10-24 | 2021-06-01 | 豪夫迈·罗氏有限公司 | 用于治疗和预防乙型肝炎病毒疾病的新型三环化合物 |
| CN113493442B (zh) * | 2020-04-03 | 2024-11-08 | 天津药物研究院有限公司 | 作为葡萄糖激酶活化剂的吡咯烷酮衍生物及其制备方法和用途 |
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| EP2010520B1 (en) | 2006-04-20 | 2012-09-12 | Pfizer Products Inc. | Heterobicyclic amides for the prevention and treatment of glucokinase-mediated diseases |
| WO2007125103A2 (en) | 2006-04-28 | 2007-11-08 | Transtech Pharma, Inc. | Benzamide glucokinase activators |
| EP2049518B1 (en) | 2006-05-31 | 2011-08-31 | Takeda San Diego, Inc. | Indazole and isoindole derivatives as glucokinase activating agents. |
| CN101490064B (zh) * | 2006-07-06 | 2012-10-10 | 百时美施贵宝公司 | 新颖葡萄糖激酶活化剂及其使用方法 |
| US7888504B2 (en) | 2006-07-06 | 2011-02-15 | Bristol-Myers Squibb Company | Glucokinase activators and methods of using same |
| US7910747B2 (en) | 2006-07-06 | 2011-03-22 | Bristol-Myers Squibb Company | Phosphonate and phosphinate pyrazolylamide glucokinase activators |
| KR20090025358A (ko) | 2006-07-24 | 2009-03-10 | 에프. 호프만-라 로슈 아게 | 글루코키나제 활성화제로서의 피라졸 |
| JP5248477B2 (ja) | 2007-03-07 | 2013-07-31 | 杏林製薬株式会社 | グルコキナーゼ活性化物質 |
| WO2008121602A1 (en) | 2007-03-29 | 2008-10-09 | Smithkline Beecham Corporation | Chemical compounds |
| US7741327B2 (en) | 2008-04-16 | 2010-06-22 | Hoffmann-La Roche Inc. | Pyrrolidinone glucokinase activators |
-
2011
- 2011-06-09 US US13/156,394 patent/US8178689B2/en not_active Expired - Fee Related
- 2011-06-14 RU RU2012156706/04A patent/RU2603191C2/ru not_active IP Right Cessation
- 2011-06-14 EP EP11726127.1A patent/EP2582706A1/en not_active Withdrawn
- 2011-06-14 JP JP2013514676A patent/JP5844355B2/ja not_active Expired - Fee Related
- 2011-06-14 CN CN201180029732.8A patent/CN102947311B/zh not_active Expired - Fee Related
- 2011-06-14 MX MX2012010668A patent/MX2012010668A/es active IP Right Grant
- 2011-06-14 KR KR1020127032727A patent/KR20130120993A/ko not_active Ceased
- 2011-06-14 CA CA2801168A patent/CA2801168A1/en not_active Abandoned
- 2011-06-14 WO PCT/EP2011/059783 patent/WO2011157682A1/en not_active Ceased
- 2011-06-14 BR BR112012032235A patent/BR112012032235A2/pt not_active IP Right Cessation
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