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 |
|---|---|---|---|---|
| JP6297590B2 (ja) * | 2012-12-25 | 2018-03-20 | ファ・メディシンＨｕａ Ｍｅｄｉｃｉｎｅ | １−（［１，３］ジオキソラン−４−イルメチル）−１ｈ−ピラゾール−３−イルアミンを調製するための方法 |
| GB201714777D0 (en) | 2017-09-14 | 2017-11-01 | Univ London Queen Mary | Agent |
| US20210387996A1 (en) * | 2018-10-24 | 2021-12-16 | Hoffmann-La Roche Inc. | Tricyclic compounds for the treatment and prophylaxis of hepatitis b virus disease |
| 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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| RS53981B1 (sr) | 2006-03-24 | 2015-10-30 | Array Biopharma Inc. | Analozi 2-aminopiridina kao aktivatori glukokinaze |
| WO2007115968A2 (en) | 2006-04-12 | 2007-10-18 | F. Hoffmann-La Roche Ag | Process for the preparation of a glucokinase activator |
| JP5190448B2 (ja) | 2006-04-20 | 2013-04-24 | ファイザー・プロダクツ・インク | グルコキナーゼ仲介疾患を予防および治療するための縮合フェニルアミド複素環化合物 |
| CA2649577A1 (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. |
| US7888504B2 (en) | 2006-07-06 | 2011-02-15 | Bristol-Myers Squibb Company | Glucokinase activators and methods of using same |
| 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 |
| US7910747B2 (en) | 2006-07-06 | 2011-03-22 | Bristol-Myers Squibb Company | Phosphonate and phosphinate pyrazolylamide glucokinase activators |
| BRPI0715531A2 (pt) | 2006-07-24 | 2014-06-24 | Hoffmann La Roche | Composto, composição farmacêutica, método para o tratamento de uma enfermidade e/ou distúrbio metabólico, processo para a preparação de compostos e uso do composto |
| MX2009009525A (es) | 2007-03-07 | 2009-09-16 | Kyorin Seiyaku Kk | Activador de glucocinasa. |
| 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 KR KR1020127032727A patent/KR20130120993A/ko not_active Ceased
- 2011-06-14 JP JP2013514676A patent/JP5844355B2/ja not_active Expired - Fee Related
- 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
- 2011-06-14 CA CA2801168A patent/CA2801168A1/en not_active Abandoned
- 2011-06-14 MX MX2012010668A patent/MX2012010668A/es active IP Right Grant
- 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 CN CN201180029732.8A patent/CN102947311B/zh not_active Expired - Fee Related
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