JP2009516698A5 - - Google Patents
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- Publication number
- JP2009516698A5 JP2009516698A5 JP2008541476A JP2008541476A JP2009516698A5 JP 2009516698 A5 JP2009516698 A5 JP 2009516698A5 JP 2008541476 A JP2008541476 A JP 2008541476A JP 2008541476 A JP2008541476 A JP 2008541476A JP 2009516698 A5 JP2009516698 A5 JP 2009516698A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- dimethyl
- tetrazol
- yloxy
- benzamide
- 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
Links
- 229910052736 halogen Inorganic materials 0.000 claims 30
- 150000002367 halogens Chemical class 0.000 claims 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- -1 3,3-dimethylbutyl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 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 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- IEYXODYZSDTZLM-UHFFFAOYSA-N 4-[1-[3,5-dimethyl-4-(4-propan-2-ylphenyl)phenoxy]-2-methylpropyl]-n-(2h-tetrazol-5-yl)benzamide Chemical compound C=1C=C(C(=O)NC=2NN=NN=2)C=CC=1C(C(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(C)C)C=C1 IEYXODYZSDTZLM-UHFFFAOYSA-N 0.000 claims 2
- OEAZXCZQIDSXFF-UHFFFAOYSA-N 4-[1-[3,5-dimethyl-4-(4-propan-2-ylphenyl)phenoxy]-3,3-dimethylbutyl]-n-(2h-tetrazol-5-yl)benzamide Chemical compound C1=CC(C(C)C)=CC=C1C(C(=C1)C)=C(C)C=C1OC(CC(C)(C)C)C1=CC=C(C(=O)NC=2NN=NN=2)C=C1 OEAZXCZQIDSXFF-UHFFFAOYSA-N 0.000 claims 2
- GGIYFPRCXGGSNT-UHFFFAOYSA-N 4-[1-[3,5-dimethyl-4-(4-propan-2-ylphenyl)phenoxy]-3,3-dimethylbutyl]-n-(2h-tetrazol-5-ylmethyl)benzamide Chemical compound C1=CC(C(C)C)=CC=C1C(C(=C1)C)=C(C)C=C1OC(CC(C)(C)C)C1=CC=C(C(=O)NCC=2NN=NN=2)C=C1 GGIYFPRCXGGSNT-UHFFFAOYSA-N 0.000 claims 2
- RNXZFVLSWQEPEX-UHFFFAOYSA-N 4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-2-methylpropyl]-n-(2h-tetrazol-5-yl)benzamide Chemical compound C=1C=C(C(=O)NC=2NN=NN=2)C=CC=1C(C(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(F)(F)F)C=C1 RNXZFVLSWQEPEX-UHFFFAOYSA-N 0.000 claims 2
- QSSGXZVLWGNTOW-UHFFFAOYSA-N 4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-2-methylpropyl]-n-(2h-tetrazol-5-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC=2NN=NN=2)C=CC=1C(C(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(F)(F)F)C=C1 QSSGXZVLWGNTOW-UHFFFAOYSA-N 0.000 claims 2
- KVSVWUQFESTPKK-UHFFFAOYSA-N 4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-3,3-dimethylbutyl]-n-(2h-tetrazol-5-yl)benzamide Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(CC(C)(C)C)C(C=C1)=CC=C1C(=O)NC1=NN=NN1 KVSVWUQFESTPKK-UHFFFAOYSA-N 0.000 claims 2
- NMCDXFULMXWSFS-UHFFFAOYSA-N 4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-3,3-dimethylbutyl]-n-(2h-tetrazol-5-ylmethyl)benzamide Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(CC(C)(C)C)C(C=C1)=CC=C1C(=O)NCC1=NN=NN1 NMCDXFULMXWSFS-UHFFFAOYSA-N 0.000 claims 2
- JBQBBKXNCPHWPO-UHFFFAOYSA-N 4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-4,4-dimethylpentyl]-n-(2h-tetrazol-5-ylmethyl)benzamide Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(CCC(C)(C)C)C(C=C1)=CC=C1C(=O)NCC1=NN=NN1 JBQBBKXNCPHWPO-UHFFFAOYSA-N 0.000 claims 2
- ZQTIEFGJUPAYBC-UHFFFAOYSA-N 4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]-4,4,4-trifluorobutyl]-n-(2h-tetrazol-5-ylmethyl)benzamide Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(C)(C)C)C(C)=CC=1OC(CCC(F)(F)F)C(C=C1)=CC=C1C(=O)NCC1=NN=NN1 ZQTIEFGJUPAYBC-UHFFFAOYSA-N 0.000 claims 2
- XHJDPUMOLPKCMD-UHFFFAOYSA-N 4-[cyclobutyl-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]methyl]-n-(2h-tetrazol-5-ylmethyl)benzamide Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(C=1C=CC(=CC=1)C(=O)NCC=1NN=NN=1)C1CCC1 XHJDPUMOLPKCMD-UHFFFAOYSA-N 0.000 claims 2
- LZEOMBAXFVHWFT-UHFFFAOYSA-N 4-[cyclopentyl-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]methyl]-n-(2h-tetrazol-5-ylmethyl)benzamide Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(C=1C=CC(=CC=1)C(=O)NCC=1NN=NN=1)C1CCCC1 LZEOMBAXFVHWFT-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- GAHUZRFXZQEOEF-UHFFFAOYSA-N 4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-3-methylbutyl]-n-(2h-tetrazol-5-yl)benzamide Chemical compound C=1C=C(C(=O)NC=2NN=NN=2)C=CC=1C(CC(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(F)(F)F)C=C1 GAHUZRFXZQEOEF-UHFFFAOYSA-N 0.000 claims 1
- IVQQVZWFMFPKRQ-UHFFFAOYSA-N 4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-3-methylbutyl]-n-(2h-tetrazol-5-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC=2NN=NN=2)C=CC=1C(CC(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(F)(F)F)C=C1 IVQQVZWFMFPKRQ-UHFFFAOYSA-N 0.000 claims 1
- SGOVBKMRAJLULN-UHFFFAOYSA-N 4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-4,4-dimethylpentyl]-n-(2h-tetrazol-5-yl)benzamide Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(CCC(C)(C)C)C(C=C1)=CC=C1C(=O)NC1=NN=NN1 SGOVBKMRAJLULN-UHFFFAOYSA-N 0.000 claims 1
- AKNWPCSPFNLSNW-UHFFFAOYSA-N 4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-5,5,5-trifluoropentyl]-n-(2h-tetrazol-5-ylmethyl)benzamide Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(CCCC(F)(F)F)C(C=C1)=CC=C1C(=O)NCC1=NN=NN1 AKNWPCSPFNLSNW-UHFFFAOYSA-N 0.000 claims 1
- WVDFSQNKAABBIU-UHFFFAOYSA-N 4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]-3-methylbutyl]-n-(2h-tetrazol-5-yl)benzamide Chemical compound C=1C=C(C(=O)NC=2NN=NN=2)C=CC=1C(CC(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(C)(C)C)C=C1 WVDFSQNKAABBIU-UHFFFAOYSA-N 0.000 claims 1
- TWKGZHZSBKORHR-UHFFFAOYSA-N 4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]-3-methylbutyl]-n-(2h-tetrazol-5-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC=2NN=NN=2)C=CC=1C(CC(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(C)(C)C)C=C1 TWKGZHZSBKORHR-UHFFFAOYSA-N 0.000 claims 1
- 125000000439 4-methylpentoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73872305P | 2005-11-22 | 2005-11-22 | |
| US60/738,723 | 2005-11-22 | ||
| PCT/US2006/060976 WO2007120270A2 (en) | 2005-11-22 | 2006-11-16 | Glucagon receptor antagonists, preparation and therapeutic uses |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009516698A JP2009516698A (ja) | 2009-04-23 |
| JP2009516698A5 true JP2009516698A5 (enExample) | 2009-12-17 |
| JP5230436B2 JP5230436B2 (ja) | 2013-07-10 |
Family
ID=38609982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008541476A Expired - Fee Related JP5230436B2 (ja) | 2005-11-22 | 2006-11-16 | グルカゴン受容体アンタゴニスト、製造及び治療的使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8691856B2 (enExample) |
| EP (1) | EP1957068B1 (enExample) |
| JP (1) | JP5230436B2 (enExample) |
| CN (1) | CN101312723B (enExample) |
| AU (1) | AU2006342137B2 (enExample) |
| BR (1) | BRPI0618140A2 (enExample) |
| CA (1) | CA2629172C (enExample) |
| ES (1) | ES2516691T3 (enExample) |
| WO (1) | WO2007120270A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1758853E (pt) * | 2004-06-14 | 2010-03-02 | Lilly Co Eli | Antagonistas do receptor de glucagon, sua preparação e usos terapêuticos |
| MX2009008534A (es) | 2007-02-09 | 2009-11-23 | Metabasis Therapeutics Inc | Antagonistas novedosos del receptor de glucagon. |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP2799428B1 (en) | 2008-08-13 | 2016-11-16 | Metabasis Therapeutics, Inc. | Glucagon antagonists |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| AU2011346670B2 (en) * | 2010-12-23 | 2015-05-07 | Pfizer Inc. | Glucagon receptor modulators |
| PH12013501557A1 (en) | 2011-02-08 | 2019-06-03 | Pfizer | Glucagon receptor modulator |
| WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| RU2013157388A (ru) | 2011-07-22 | 2015-08-27 | Пфайзер Инк. | Хинолинильные модуляторы глюкагонового рецептора |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP3065736B1 (en) | 2013-11-04 | 2018-11-14 | Merck Sharp & Dohme Corp. | Glucagon receptor antagonist compounds, compositions thereof, and methods of use |
| WO2015191900A1 (en) | 2014-06-12 | 2015-12-17 | Ligand Pharmaceuticals, Inc. | Glucagon antagonists |
| JP2021513564A (ja) | 2018-02-13 | 2021-05-27 | リガンド・ファーマシューティカルズ・インコーポレイテッド | グルカゴン受容体拮抗薬 |
| CN108727157B (zh) * | 2018-07-06 | 2020-04-28 | 大连理工大学 | 胰高血糖素受体拮抗剂中间体的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4973731A (en) | 1987-04-23 | 1990-11-27 | Riker Laboratories, Inc. | Di-t-butylphenyl alkyl and benzyl ether nitriles |
| GB9420557D0 (en) | 1994-10-12 | 1994-11-30 | Zeneca Ltd | Aromatic compounds |
| US6706744B2 (en) | 2000-11-17 | 2004-03-16 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
| AU2002365622A1 (en) | 2001-12-03 | 2003-06-17 | Novo Nordisk A/S | Novel glucagon antagonists |
| JP2006500325A (ja) * | 2002-06-27 | 2006-01-05 | ノボ ノルディスク アクティーゼルスカブ | 新規なグルカゴンアンタゴニスト |
| WO2004056763A2 (en) | 2002-12-20 | 2004-07-08 | Novo Nordisk A/S | Novel glucagon antagonists |
| PT1758853E (pt) * | 2004-06-14 | 2010-03-02 | Lilly Co Eli | Antagonistas do receptor de glucagon, sua preparação e usos terapêuticos |
| US8318760B2 (en) | 2005-03-21 | 2012-11-27 | Merck Sharp & Dohme Corp. | Substituted aryl and heteroaryl derivatives, compositions containing such compounds and methods of use |
-
2006
- 2006-11-16 CN CN2006800436264A patent/CN101312723B/zh not_active Expired - Fee Related
- 2006-11-16 AU AU2006342137A patent/AU2006342137B2/en not_active Ceased
- 2006-11-16 ES ES06850764.9T patent/ES2516691T3/es active Active
- 2006-11-16 WO PCT/US2006/060976 patent/WO2007120270A2/en not_active Ceased
- 2006-11-16 US US12/093,601 patent/US8691856B2/en not_active Expired - Fee Related
- 2006-11-16 EP EP06850764.9A patent/EP1957068B1/en not_active Not-in-force
- 2006-11-16 BR BRPI0618140-6A patent/BRPI0618140A2/pt not_active IP Right Cessation
- 2006-11-16 CA CA2629172A patent/CA2629172C/en not_active Expired - Fee Related
- 2006-11-16 JP JP2008541476A patent/JP5230436B2/ja not_active Expired - Fee Related