JP5653907B2 - 11β−ヒドロキシステロイドデヒドロゲナーゼ1のカルバマート及び尿素阻害剤 - Google Patents
11β−ヒドロキシステロイドデヒドロゲナーゼ1のカルバマート及び尿素阻害剤 Download PDFInfo
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- JP5653907B2 JP5653907B2 JP2011506287A JP2011506287A JP5653907B2 JP 5653907 B2 JP5653907 B2 JP 5653907B2 JP 2011506287 A JP2011506287 A JP 2011506287A JP 2011506287 A JP2011506287 A JP 2011506287A JP 5653907 B2 JP5653907 B2 JP 5653907B2
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- Prior art keywords
- alkyl
- adamantyl
- carboxylate
- pyrrolidine
- represented
- 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.)
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- 239000003112 inhibitor Substances 0.000 title description 22
- 102100036506 11-beta-hydroxysteroid dehydrogenase 1 Human genes 0.000 title description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title description 2
- 101710186107 11-beta-hydroxysteroid dehydrogenase 1 Proteins 0.000 title 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title 1
- 239000004202 carbamide Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 241
- 150000001875 compounds Chemical class 0.000 claims description 227
- 125000001072 heteroaryl group Chemical group 0.000 claims description 161
- 125000000623 heterocyclic group Chemical group 0.000 claims description 138
- 125000003118 aryl group Chemical group 0.000 claims description 131
- -1 (3R)-(1- (hydroxymethyl) -4-adamantyl) Chemical group 0.000 claims description 111
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 93
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 88
- 229910052736 halogen Inorganic materials 0.000 claims description 78
- 150000002367 halogens Chemical class 0.000 claims description 76
- 150000003839 salts Chemical class 0.000 claims description 70
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 50
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 46
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 43
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 201000010099 disease Diseases 0.000 claims description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
- 230000000694 effects Effects 0.000 claims description 18
- 125000003107 substituted aryl group Chemical group 0.000 claims description 18
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
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- 125000005842 heteroatom Chemical group 0.000 claims description 8
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- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 8
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
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- LDWNGJZCOABBTF-UHFFFAOYSA-N 2-adamantyl 3-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pyrrolidine-1-carboxylate Chemical compound C1C(N(C)C(=O)OC(C)(C)C)CCN1C(=O)OC1C(C2)CC3CC2CC1C3 LDWNGJZCOABBTF-UHFFFAOYSA-N 0.000 claims description 4
- KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
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- IIVUJUOJERNGQX-UHFFFAOYSA-N pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=CN=C1 IIVUJUOJERNGQX-UHFFFAOYSA-N 0.000 claims description 3
- PIBARXGEUTVUOA-JOUIXUNQSA-N (5-carbamoyl-2-adamantyl) (3r)-3-(2-methylpropoxycarbonylamino)pyrrolidine-1-carboxylate Chemical compound C1[C@H](NC(=O)OCC(C)C)CCN1C(=O)OC1C2CC(C3)CC1CC3(C(N)=O)C2 PIBARXGEUTVUOA-JOUIXUNQSA-N 0.000 claims description 2
- ZIPTYTLLXWDDDB-UHFFFAOYSA-N 1-(5-cyanopyridin-2-yl)-1,7-diazaspiro[4.4]nonane-7-carboxylic acid Chemical compound C1CC2(CCN(C2)C(=O)O)N(C1)C3=NC=C(C=C3)C#N ZIPTYTLLXWDDDB-UHFFFAOYSA-N 0.000 claims description 2
- JOGYVMHTBBGSEP-UHFFFAOYSA-N 1-o-tert-butyl 7-o-(5-carbamoyl-2-adamantyl) 1,7-diazaspiro[4.4]nonane-1,7-dicarboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC11CN(C(=O)OC2C3CC4CC2CC(C4)(C3)C(N)=O)CC1 JOGYVMHTBBGSEP-UHFFFAOYSA-N 0.000 claims description 2
- WWLXCBWZRWCQOW-SVXFNXITSA-N 2-adamantyl (3r)-3-(2-methylpropoxycarbonylamino)pyrrolidine-1-carboxylate Chemical compound C1[C@H](NC(=O)OCC(C)C)CCN1C(=O)OC1C(C2)CC3CC2CC1C3 WWLXCBWZRWCQOW-SVXFNXITSA-N 0.000 claims description 2
- MTMPMDZHCAGNOP-OBYDGYHJSA-N 2-adamantyl (3r)-3-(propan-2-yloxycarbonylamino)pyrrolidine-1-carboxylate Chemical compound C1[C@H](NC(=O)OC(C)C)CCN1C(=O)OC1C(C2)CC3CC2CC1C3 MTMPMDZHCAGNOP-OBYDGYHJSA-N 0.000 claims description 2
- SSLZFXAKKAGXLV-OBYDGYHJSA-N 2-adamantyl (3r)-3-(propoxycarbonylamino)pyrrolidine-1-carboxylate Chemical compound C1[C@H](NC(=O)OCCC)CCN1C(=O)OC1C(C2)CC3CC2CC1C3 SSLZFXAKKAGXLV-OBYDGYHJSA-N 0.000 claims description 2
- CIPVYGVVXDZUIY-UHFFFAOYSA-N 2-adamantyl 3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpyrrolidine-1-carboxylate Chemical compound C1CN(C(=O)OC2C3CC4CC(C3)CC2C4)CC1(NC(=O)OC(C)(C)C)C1=CC=CC=C1 CIPVYGVVXDZUIY-UHFFFAOYSA-N 0.000 claims description 2
- WZLAPUQGAHBBHA-UHFFFAOYSA-N 2-adamantyl 3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]azetidine-1-carboxylate Chemical compound C1C(CNC(=O)OC(C)(C)C)CN1C(=O)OC1C(C2)CC3CC2CC1C3 WZLAPUQGAHBBHA-UHFFFAOYSA-N 0.000 claims description 2
- XLULVUAXKZRSAI-UHFFFAOYSA-N 3-[(3-cyanopyridin-2-yl)amino]-3-methylpyrrolidine-1-carboxylic acid Chemical compound CC1(CCN(C1)C(=O)O)NC2=C(C=CC=N2)C#N XLULVUAXKZRSAI-UHFFFAOYSA-N 0.000 claims description 2
- DLBNBWGSRQHXBC-UHFFFAOYSA-N 3-[(5-cyanopyridin-2-yl)amino]-3-methylpyrrolidine-1-carboxylic acid Chemical compound CC1(CCN(C1)C(=O)O)NC2=NC=C(C=C2)C#N DLBNBWGSRQHXBC-UHFFFAOYSA-N 0.000 claims description 2
- AXOCXCOXJZFBEG-UHFFFAOYSA-N 5-o-(2-adamantyl) 1-o-tert-butyl 2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-1,5-dicarboxylate Chemical compound C1C(CC2C3)CC3CC1C2OC(=O)N1CC2CCN(C(=O)OC(C)(C)C)C2C1 AXOCXCOXJZFBEG-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C07—ORGANIC CHEMISTRY
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- C07D487/04—Ortho-condensed systems
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12507208P | 2008-04-22 | 2008-04-22 | |
| US61/125,072 | 2008-04-22 | ||
| PCT/US2009/002478 WO2009131669A2 (en) | 2008-04-22 | 2009-04-21 | Carbamate and urea inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011518218A JP2011518218A (ja) | 2011-06-23 |
| JP2011518218A5 JP2011518218A5 (enExample) | 2012-06-07 |
| JP5653907B2 true JP5653907B2 (ja) | 2015-01-14 |
Family
ID=41100453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011506287A Expired - Fee Related JP5653907B2 (ja) | 2008-04-22 | 2009-04-21 | 11β−ヒドロキシステロイドデヒドロゲナーゼ1のカルバマート及び尿素阻害剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8399504B2 (enExample) |
| EP (1) | EP2276730A2 (enExample) |
| JP (1) | JP5653907B2 (enExample) |
| AR (1) | AR071386A1 (enExample) |
| CA (1) | CA2721750A1 (enExample) |
| TW (1) | TW200944526A (enExample) |
| WO (1) | WO2009131669A2 (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009017671A1 (en) | 2007-07-26 | 2009-02-05 | Vitae Pharmaceuticals, Inc. | Synthesis of inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 |
| AR069207A1 (es) | 2007-11-07 | 2010-01-06 | Vitae Pharmaceuticals Inc | Ureas ciclicas como inhibidores de la 11 beta - hidroxi-esteroide deshidrogenasa 1 |
| EP2220048B1 (en) * | 2007-11-16 | 2017-01-25 | Boehringer Ingelheim International GmbH | Aryl- and heteroarylcarbonyl derivatives of benzomorphanes and related scaffolds, medicaments containing such compounds and their use |
| US8440658B2 (en) | 2007-12-11 | 2013-05-14 | Vitae Pharmaceuticals, Inc. | Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| TW200934490A (en) | 2008-01-07 | 2009-08-16 | Vitae Pharmaceuticals Inc | Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1 |
| US8592409B2 (en) | 2008-01-24 | 2013-11-26 | Vitae Pharmaceuticals, Inc. | Cyclic carbazate and semicarbazide inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| EP2245014B1 (en) * | 2008-02-12 | 2011-11-02 | Boehringer Ingelheim International GmbH | Urea derivatives of benzomorphanes and related scaffolds, medicaments containing such compounds and their use |
| CA2715290A1 (en) | 2008-02-15 | 2009-08-20 | Vitae Pharmaceuticals, Inc. | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| TW200944526A (en) * | 2008-04-22 | 2009-11-01 | Vitae Pharmaceuticals Inc | Carbamate and urea inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| CA2723034A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| JP5301563B2 (ja) | 2008-05-01 | 2013-09-25 | ヴァイティー ファーマシューティカルズ,インコーポレイテッド | 11β−ヒドロキシステロイドデヒドロゲナーゼ1の環状インヒビター |
| EP2291371B1 (en) | 2008-05-01 | 2015-06-10 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| EP2288596B1 (en) | 2008-05-13 | 2016-11-30 | Boehringer Ingelheim International GmbH | Alicyclic carboxylic acid derivatives of benzomorphans and related scaffolds, medicaments containing such compounds and their use |
| CA2729998A1 (en) | 2008-07-25 | 2010-01-28 | Boehringer Ingelheim International Gmbh | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2010010150A1 (en) | 2008-07-25 | 2010-01-28 | Boehringer Ingelheim International Gmbh | Synthesis of inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 |
| PL2324018T3 (pl) | 2008-07-25 | 2014-02-28 | Boehringer Ingelheim Int | Cykliczne inhibitory dehydrogenazy 11 beta-hydroksysteroidowej typu 1 |
| WO2010046445A2 (en) | 2008-10-23 | 2010-04-29 | Boehringer Ingelheim International Gmbh | Urea derivatives of substituted nortropanes, medicaments containing such compounds and their use |
| JP5679997B2 (ja) | 2009-02-04 | 2015-03-04 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 11β−ヒドロキシステロイドデヒドロゲナーゼ1の環状阻害剤 |
| MA33216B1 (fr) | 2009-04-30 | 2012-04-02 | Boehringer Ingelheim Int | Inhibiteurs cycliques de la 11béta-hydroxysteroïde déshydrogénase 1 |
| WO2010139673A1 (en) | 2009-06-02 | 2010-12-09 | Boehringer Ingelheim International Gmbh | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| AR076936A1 (es) * | 2009-06-02 | 2011-07-20 | Vitae Pharmaceuticals Inc | Inhibidores de carbamato y urea de la 11 beta hidroxiesteroide deshidrogenasa 1 |
| WO2011011123A1 (en) | 2009-06-11 | 2011-01-27 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 based on the 1,3 -oxazinan- 2 -one structure |
| EP2448928B1 (en) | 2009-07-01 | 2014-08-13 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2011056737A1 (en) | 2009-11-05 | 2011-05-12 | Boehringer Ingelheim International Gmbh | Novel chiral phosphorus ligands |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| CN102219759B (zh) * | 2010-04-16 | 2013-07-24 | 中国科学院上海药物研究所 | 芳基甲酰胺类化合物及其制备方法、药物组合物和用途 |
| JP2013531636A (ja) | 2010-05-26 | 2013-08-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 2−オキソ−1,2−ジヒドロピリジン−4−イルボロン酸誘導体 |
| US8933072B2 (en) | 2010-06-16 | 2015-01-13 | Vitae Pharmaceuticals, Inc. | Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use |
| 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 |
| EP2585444B1 (en) | 2010-06-25 | 2014-10-22 | Boehringer Ingelheim International GmbH | Azaspirohexanones as inhibitors of 11-beta-hsd1 for the treatment of metabolic disorders |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, 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 |
| 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 |
| WO2012059416A1 (en) | 2010-11-02 | 2012-05-10 | Boehringer Ingelheim International Gmbh | Pharmaceutical combinations for the treatment of metabolic disorders |
| EP2744783A1 (en) | 2011-08-17 | 2014-06-25 | Boehringer Ingelheim International GmbH | Indenopyridine derivatives |
| 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 |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP3235813A1 (en) | 2016-04-19 | 2017-10-25 | Cidqo 2012, S.L. | Aza-tetra-cyclo derivatives |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| IL137517A0 (en) | 1998-01-27 | 2001-07-24 | Aventis Pharm Prod Inc | Substituted oxoazaheterocyclyl factor xa inhibitors |
| US7410995B1 (en) * | 1998-08-14 | 2008-08-12 | Gpi Nil Holdings Inc. | N-linked sulfonamide of heterocyclic thioesters for vision and memory disorders |
| HUP0203375A3 (en) | 1999-07-28 | 2005-03-29 | Aventis Pharm Prod Inc | Substituted oxoazaheterocyclyl compounds |
| CA2420177C (en) * | 2000-08-31 | 2008-07-08 | F. Hoffmann-La Roche Ag | Quinazoline derivatives as alpha-1 adrenergic antagonists |
| RU2300524C2 (ru) * | 2001-12-03 | 2007-06-10 | Ф.Хоффманн-Ля Рош Аг | Производные 4-пиперидинилалкиламина и фармацевтическая композиция, обладающая антагонистическим действием в отношении мускариновых рецепторов |
| TW200403058A (en) | 2002-04-19 | 2004-03-01 | Bristol Myers Squibb Co | Heterocyclo inhibitors of potassium channel function |
| CA2497440C (en) * | 2002-09-04 | 2011-03-22 | Schering Corporation | Pyrazolopyrimidines as cyclin-dependent kinase inhibitors |
| US20050256159A1 (en) | 2002-10-11 | 2005-11-17 | Astrazeneca Ab | 1,4-disubstituted piperidine derivatives and their use as 11,betahsd1 inhibitors |
| WO2004056744A1 (en) | 2002-12-23 | 2004-07-08 | Janssen Pharmaceutica N.V. | Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors |
| JP2004315511A (ja) | 2003-03-31 | 2004-11-11 | Taisho Pharmaceut Co Ltd | Mch受容体アンタゴニスト |
| GB0325745D0 (en) | 2003-11-05 | 2003-12-10 | Astrazeneca Ab | Chemical compounds |
| GB0326029D0 (en) | 2003-11-07 | 2003-12-10 | Astrazeneca Ab | Chemical compounds |
| EP2308562B1 (en) * | 2003-12-25 | 2015-02-25 | Ono Pharmaceutical Co., Ltd. | Azetidine ring compounds and drugs comprising the same |
| WO2006012226A2 (en) | 2004-06-24 | 2006-02-02 | Incyte Corporation | N-substituted piperidines and their use as pharmaceuticals |
| JP2008504278A (ja) | 2004-06-24 | 2008-02-14 | インサイト・コーポレイション | アミド化合物およびその医薬としての使用 |
| CA2585735A1 (en) | 2004-11-02 | 2006-05-11 | Pfizer Inc. | Novel compounds of substituted and unsubstituted adamantyl amides |
| US20060148871A1 (en) | 2005-01-05 | 2006-07-06 | Rohde Jeffrey J | Metabolic stabilization of substituted adamantane |
| WO2007038138A2 (en) | 2005-09-21 | 2007-04-05 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| EP1801098A1 (en) * | 2005-12-16 | 2007-06-27 | Merck Sante | 2-Adamantylurea derivatives as selective 11B-HSD1 inhibitors |
| JP2007204744A (ja) * | 2006-01-05 | 2007-08-16 | Toyobo Co Ltd | ポリエステル樹脂、ポリエステル樹脂組成物およびそれからなるポリエステル成形体並びにポリエステル成形体の製造方法 |
| US20070208001A1 (en) | 2006-03-03 | 2007-09-06 | Jincong Zhuo | Modulators of 11- beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same |
| WO2009020140A1 (ja) * | 2007-08-06 | 2009-02-12 | Dainippon Sumitomo Pharma Co., Ltd. | アダマンチルウレア誘導体 |
| TW200944526A (en) * | 2008-04-22 | 2009-11-01 | Vitae Pharmaceuticals Inc | Carbamate and urea inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
-
2009
- 2009-04-20 TW TW098112970A patent/TW200944526A/zh unknown
- 2009-04-21 WO PCT/US2009/002478 patent/WO2009131669A2/en not_active Ceased
- 2009-04-21 AR ARP090101394A patent/AR071386A1/es unknown
- 2009-04-21 US US12/988,374 patent/US8399504B2/en not_active Expired - Fee Related
- 2009-04-21 EP EP09733956A patent/EP2276730A2/en not_active Withdrawn
- 2009-04-21 CA CA2721750A patent/CA2721750A1/en not_active Abandoned
- 2009-04-21 JP JP2011506287A patent/JP5653907B2/ja not_active Expired - Fee Related
-
2013
- 2013-02-15 US US13/769,256 patent/US8828985B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AR071386A1 (es) | 2010-06-16 |
| TW200944526A (en) | 2009-11-01 |
| US8828985B2 (en) | 2014-09-09 |
| US8399504B2 (en) | 2013-03-19 |
| CA2721750A1 (en) | 2009-10-29 |
| US20130244994A1 (en) | 2013-09-19 |
| WO2009131669A2 (en) | 2009-10-29 |
| JP2011518218A (ja) | 2011-06-23 |
| US20110112062A1 (en) | 2011-05-12 |
| EP2276730A2 (en) | 2011-01-26 |
| WO2009131669A3 (en) | 2010-04-01 |
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