JP2010539151A5 - - Google Patents
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- JP2010539151A5 JP2010539151A5 JP2010524582A JP2010524582A JP2010539151A5 JP 2010539151 A5 JP2010539151 A5 JP 2010539151A5 JP 2010524582 A JP2010524582 A JP 2010524582A JP 2010524582 A JP2010524582 A JP 2010524582A JP 2010539151 A5 JP2010539151 A5 JP 2010539151A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- compound
- piperidyl
- heterocycloalkyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 74
- 125000003545 alkoxy group Chemical group 0.000 claims 50
- 150000001875 compounds Chemical class 0.000 claims 49
- 150000003839 salts Chemical class 0.000 claims 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 14
- 239000000203 mixture Substances 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 10
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- -1 diastereomers Chemical class 0.000 claims 2
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 2
- NNBXAFHPUMFFFB-RTBURBONSA-N (3ar,7ar)-3-[1-[1-(cyclopropanecarbonyl)-4-methylpiperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(C)(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CCN1C(=O)C1CC1 NNBXAFHPUMFFFB-RTBURBONSA-N 0.000 claims 1
- LEPSCPYTKQZCBU-QUCCMNQESA-N (3ar,7as)-1-[1-[1-(cyclopropanecarbonyl)-4-methylpiperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-3h-indol-2-one Chemical compound C1CC(C)(N2CCC(CC2)N2C(C[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1CC1 LEPSCPYTKQZCBU-QUCCMNQESA-N 0.000 claims 1
- AQFWXNVSYIPMHD-ROUUACIJSA-N (3as,7as)-3-[1-(4-methyl-1-propanoylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)CC)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 AQFWXNVSYIPMHD-ROUUACIJSA-N 0.000 claims 1
- NNBXAFHPUMFFFB-OALUTQOASA-N (3as,7as)-3-[1-[1-(cyclopropanecarbonyl)-4-methylpiperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(C)(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1CC1 NNBXAFHPUMFFFB-OALUTQOASA-N 0.000 claims 1
- SEEBTWYJDVPAJW-SFTDATJTSA-N (3as,7as)-3-[1-[1-(cyclopropanecarbonyl)-4-propylpiperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(CCC)(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1CC1 SEEBTWYJDVPAJW-SFTDATJTSA-N 0.000 claims 1
- NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 claims 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims 1
- CCHCOSYSXRNJPP-NBJLRHFZSA-N 2-fluoroethyl 3-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1CC(N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C1(C)CCN(C(=O)OCCF)C1 CCHCOSYSXRNJPP-NBJLRHFZSA-N 0.000 claims 1
- BILIYBGFXJGAPT-UHFFFAOYSA-N 3-methylpyrrolidine-1-carboxylic acid Chemical compound CC1CCN(C(O)=O)C1 BILIYBGFXJGAPT-UHFFFAOYSA-N 0.000 claims 1
- VIRFRHVDXNAETH-UHFFFAOYSA-N 4-methylpiperidine-1-carboxylic acid Chemical compound CC1CCN(C(O)=O)CC1 VIRFRHVDXNAETH-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- QZHXKFXCKFGNJH-NVPCEHRXSA-N but-2-ynyl 3-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC#CC)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 QZHXKFXCKFGNJH-NVPCEHRXSA-N 0.000 claims 1
- XXXPJMMKHPCKGA-PMACEKPBSA-N but-2-ynyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC#CC)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 XXXPJMMKHPCKGA-PMACEKPBSA-N 0.000 claims 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- LJENYWOZYGSALB-LGJCEAAXSA-N ethyl 3-[4-[(3ar,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 LJENYWOZYGSALB-LGJCEAAXSA-N 0.000 claims 1
- FSRWEZFSESZVCX-NOORDXFBSA-N ethyl 3-[4-[(3as,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-indol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1(C)N1CCC(N2C(C[C@@H]3CCCC[C@H]32)=O)CC1 FSRWEZFSESZVCX-NOORDXFBSA-N 0.000 claims 1
- LJENYWOZYGSALB-NBJLRHFZSA-N ethyl 3-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 LJENYWOZYGSALB-NBJLRHFZSA-N 0.000 claims 1
- IVJDEIANCSDDAO-QZTJIDSGSA-N ethyl 4-[4-[(3ar,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 IVJDEIANCSDDAO-QZTJIDSGSA-N 0.000 claims 1
- IVJDEIANCSDDAO-MSOLQXFVSA-N ethyl 4-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@@H]32)=O)CC1 IVJDEIANCSDDAO-MSOLQXFVSA-N 0.000 claims 1
- FBMWQXFLRCKPIQ-OALUTQOASA-N ethyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(CC)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 FBMWQXFLRCKPIQ-OALUTQOASA-N 0.000 claims 1
- IVJDEIANCSDDAO-ROUUACIJSA-N ethyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 IVJDEIANCSDDAO-ROUUACIJSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- DYRVQYFEYGVZSQ-NRAVZPKASA-N methyl 3-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 DYRVQYFEYGVZSQ-NRAVZPKASA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- AQNYLONDPBAVGN-GAOSQQNJSA-N prop-2-ynyl 3-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1CC(N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C1(C)CCN(C(=O)OCC#C)C1 AQNYLONDPBAVGN-GAOSQQNJSA-N 0.000 claims 1
- PTNFPCNYGTUQIT-OALUTQOASA-N prop-2-ynyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CC(N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C1(C)CCN(C(=O)OCC#C)CC1 PTNFPCNYGTUQIT-OALUTQOASA-N 0.000 claims 1
- ZXKUTOMRBVXFKV-RTBURBONSA-N propan-2-yl 4-[4-[(3ar,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 ZXKUTOMRBVXFKV-RTBURBONSA-N 0.000 claims 1
- ZXKUTOMRBVXFKV-MOPGFXCFSA-N propan-2-yl 4-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@@H]32)=O)CC1 ZXKUTOMRBVXFKV-MOPGFXCFSA-N 0.000 claims 1
- IXBYUAVOBQEXJC-QUCCMNQESA-N propan-2-yl 4-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-indol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1(C)N1CCC(N2C(C[C@H]3CCCC[C@@H]32)=O)CC1 IXBYUAVOBQEXJC-QUCCMNQESA-N 0.000 claims 1
- ZILONDDNNQKVBD-PMACEKPBSA-N propan-2-yl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound C1CC(N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C1(CC)CCN(C(=O)OC(C)C)CC1 ZILONDDNNQKVBD-PMACEKPBSA-N 0.000 claims 1
- ZXKUTOMRBVXFKV-OALUTQOASA-N propan-2-yl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 ZXKUTOMRBVXFKV-OALUTQOASA-N 0.000 claims 1
- XDVGHJKTMFQYAT-SFTDATJTSA-N propan-2-yl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-propylpiperidine-1-carboxylate Chemical compound C1CC(N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C1(CCC)CCN(C(=O)OC(C)C)CC1 XDVGHJKTMFQYAT-SFTDATJTSA-N 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- FOLNBRUMVDDPBA-RTBURBONSA-N tert-butyl 4-[4-[(3ar,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 FOLNBRUMVDDPBA-RTBURBONSA-N 0.000 claims 1
- FOLNBRUMVDDPBA-OALUTQOASA-N tert-butyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 FOLNBRUMVDDPBA-OALUTQOASA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97128807P | 2007-09-11 | 2007-09-11 | |
| PCT/GB2008/050802 WO2009034380A1 (en) | 2007-09-11 | 2008-09-09 | Piperidine derivatives as agonists of muscarinic receptors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010539151A JP2010539151A (ja) | 2010-12-16 |
| JP2010539151A5 true JP2010539151A5 (enExample) | 2011-10-13 |
Family
ID=40011174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010524582A Pending JP2010539151A (ja) | 2007-09-11 | 2008-09-09 | ムスカリン受容体のアゴニストとしてのピペリジン誘導体 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8119661B2 (enExample) |
| EP (1) | EP2197843B1 (enExample) |
| JP (1) | JP2010539151A (enExample) |
| KR (1) | KR20100052528A (enExample) |
| CN (1) | CN101874020B (enExample) |
| AR (1) | AR071245A1 (enExample) |
| AT (1) | ATE539056T1 (enExample) |
| AU (1) | AU2008299604A1 (enExample) |
| BR (1) | BRPI0816331A2 (enExample) |
| CA (1) | CA2699286A1 (enExample) |
| CL (1) | CL2008002689A1 (enExample) |
| ES (1) | ES2377772T3 (enExample) |
| MX (1) | MX2010002584A (enExample) |
| PE (1) | PE20091090A1 (enExample) |
| RU (1) | RU2010110036A (enExample) |
| TW (1) | TW200924766A (enExample) |
| UY (1) | UY31334A1 (enExample) |
| WO (1) | WO2009034380A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200815405A (en) * | 2006-06-09 | 2008-04-01 | Astrazeneca Ab | Novel compounds |
| TW200813018A (en) * | 2006-06-09 | 2008-03-16 | Astrazeneca Ab | Novel compounds |
| US20090221642A1 (en) * | 2008-03-03 | 2009-09-03 | Astrazeneca Ab | Muscarinic receptor agonists, compositions, methods of treatment thereof, and processes for preparation thereof-176 |
| US20090275574A1 (en) * | 2008-05-05 | 2009-11-05 | Astrazeneca Ab | Novel compounds-300 |
| ES2619829T3 (es) | 2011-11-18 | 2017-06-27 | Heptares Therapeutics Limited | Agonistas del receptor muscarínico M1 |
| EP2897948B1 (en) * | 2012-09-18 | 2016-08-31 | Heptares Therapeutics Limited | Bicyclic aza compounds as muscarinic m1 receptor agonists |
| US9593106B2 (en) | 2013-02-07 | 2017-03-14 | Heptares Therapeutics Limited | Piperidin-1-yl and azepin-1-yl carboxylates as muscarinic M4 receptor agonists |
| GB2519470A (en) * | 2013-09-18 | 2015-04-22 | Heptares Therapeutics Ltd | Bicyclic aza compounds as muscarinic M1 receptor agonists |
| RU2685230C2 (ru) | 2014-02-06 | 2019-04-17 | Хептарес Терапьютикс Лимитед | Бициклические азотсодержащие соединения как агонисты М1 мускариновых рецепторов |
| GB201404922D0 (en) | 2014-03-19 | 2014-04-30 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201513743D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| GB201519352D0 (en) | 2015-11-02 | 2015-12-16 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201617454D0 (en) | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
| GB201810239D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819960D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819961D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB202020191D0 (en) | 2020-12-18 | 2021-02-03 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3066434D1 (en) | 1979-11-21 | 1984-03-08 | Kyowa Hakko Kogyo Kk | Novel piperidine derivatives, method for the preparation thereof and pharmaceutical compositions containing them |
| DE4302051A1 (de) | 1993-01-26 | 1994-07-28 | Thomae Gmbh Dr K | 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| AU691829B2 (en) * | 1993-07-16 | 1998-05-28 | Merck & Co., Inc. | Benzoxazinone and benzopyrimidinone piperidinyl tocolytic oxytocin receptor antagonists |
| AU701127B2 (en) | 1994-10-27 | 1999-01-21 | Merck & Co., Inc. | Muscarine antagonists |
| US5756508A (en) * | 1995-10-31 | 1998-05-26 | Merck & Co., Inc. | Muscarine antagonists |
| WO1997016192A1 (en) | 1995-10-31 | 1997-05-09 | Merck & Co., Inc. | Muscarine antagonists |
| US5756497A (en) * | 1996-03-01 | 1998-05-26 | Merck & Co., Inc. | Tocolytic oxytocin receptor antagonists |
| DE59711622D1 (de) | 1996-09-10 | 2004-06-17 | Boehringer Ingelheim Pharma | Abgewandelte aminosäuren, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| JPH10158192A (ja) * | 1996-10-03 | 1998-06-16 | Eisai Co Ltd | 移植片対宿主疾患（ｇｖｈｄ）の治療および臓器移植時の移植片拒絶反応抑制のための医薬組成物 |
| SE9704546D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| WO1999032481A1 (en) | 1997-12-23 | 1999-07-01 | Alcon Laboratories, Inc. | Muscarinic agents and use thereof to treat glaucoma, myopia and various other conditions |
| PL342046A1 (en) | 1998-01-19 | 2001-05-21 | Pfizer | 4-(2-keto-1-benzimidazolinyl)piperidine compounds as agonists of orl1 receptor |
| MA26659A1 (fr) * | 1998-08-06 | 2004-12-20 | Pfizer | Dérivés de benzimidazole nouveaux, compositions pharmaceutiques les contenant et procédé pour leur préparation. |
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2008
- 2008-09-08 US US12/205,968 patent/US8119661B2/en not_active Expired - Fee Related
- 2008-09-09 CA CA2699286A patent/CA2699286A1/en not_active Abandoned
- 2008-09-09 KR KR1020107005282A patent/KR20100052528A/ko not_active Withdrawn
- 2008-09-09 RU RU2010110036/04A patent/RU2010110036A/ru unknown
- 2008-09-09 JP JP2010524582A patent/JP2010539151A/ja active Pending
- 2008-09-09 AT AT08806636T patent/ATE539056T1/de active
- 2008-09-09 EP EP08806636A patent/EP2197843B1/en not_active Not-in-force
- 2008-09-09 AU AU2008299604A patent/AU2008299604A1/en not_active Abandoned
- 2008-09-09 BR BRPI0816331 patent/BRPI0816331A2/pt not_active Application Discontinuation
- 2008-09-09 CN CN2008801155657A patent/CN101874020B/zh not_active Expired - Fee Related
- 2008-09-09 MX MX2010002584A patent/MX2010002584A/es not_active Application Discontinuation
- 2008-09-09 TW TW097134582A patent/TW200924766A/zh unknown
- 2008-09-09 ES ES08806636T patent/ES2377772T3/es active Active
- 2008-09-09 WO PCT/GB2008/050802 patent/WO2009034380A1/en not_active Ceased
- 2008-09-10 CL CL2008002689A patent/CL2008002689A1/es unknown
- 2008-09-10 UY UY31334A patent/UY31334A1/es unknown
- 2008-09-10 AR ARP080103926A patent/AR071245A1/es unknown
- 2008-09-11 PE PE2008001586A patent/PE20091090A1/es not_active Application Discontinuation