JP2009539831A5 - - Google Patents
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- JP2009539831A5 JP2009539831A5 JP2009514231A JP2009514231A JP2009539831A5 JP 2009539831 A5 JP2009539831 A5 JP 2009539831A5 JP 2009514231 A JP2009514231 A JP 2009514231A JP 2009514231 A JP2009514231 A JP 2009514231A JP 2009539831 A5 JP2009539831 A5 JP 2009539831A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- piperidyl
- benzimidazol
- hexahydro
- alkoxy
- 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.)
- Ceased
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- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- -1 4-heptyl Chemical group 0.000 claims description 16
- SXVOJMDLKZHJBL-ROUUACIJSA-N ethyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 SXVOJMDLKZHJBL-ROUUACIJSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 89
- 150000001875 compounds Chemical class 0.000 claims 41
- 150000003839 salts Chemical class 0.000 claims 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 30
- 239000001257 hydrogen Substances 0.000 claims 30
- 150000002431 hydrogen Chemical class 0.000 claims 24
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 150000002367 halogens Chemical class 0.000 claims 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
- 125000002393 azetidinyl group Chemical group 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000003386 piperidinyl group Chemical group 0.000 claims 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 4
- 125000004104 aryloxy 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
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 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 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-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
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- DBWUZUSWJDAQMD-FGZHOGPDSA-N (3ar,7ar)-3-[1-(1-benzoylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CCN1C(=O)C1=CC=CC=C1 DBWUZUSWJDAQMD-FGZHOGPDSA-N 0.000 claims 1
- LCIHDOOZKXOYAA-RTBURBONSA-N (3ar,7ar)-3-[1-(1-butanoylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)CCC)CCC1N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 LCIHDOOZKXOYAA-RTBURBONSA-N 0.000 claims 1
- LUDJURAMNWXMQL-DHIUTWEWSA-N (3ar,7ar)-3-[1-[1-(2,6-dimethylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CC1=CC=CC(C)=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 LUDJURAMNWXMQL-DHIUTWEWSA-N 0.000 claims 1
- CDHZCKYVYJFWIQ-FGZHOGPDSA-N (3ar,7ar)-3-[1-[1-(2-methoxybenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound COC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 CDHZCKYVYJFWIQ-FGZHOGPDSA-N 0.000 claims 1
- CEEPQONDLRSWHP-DHIUTWEWSA-N (3ar,7ar)-3-[1-[1-(2-methylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 CEEPQONDLRSWHP-DHIUTWEWSA-N 0.000 claims 1
- HFTYBVTZIUWPKC-NHCUHLMSSA-N (3ar,7ar)-3-[1-[1-(cyclopentanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CCN1C(=O)C1CCCC1 HFTYBVTZIUWPKC-NHCUHLMSSA-N 0.000 claims 1
- ACVMDJFCEPWEDE-RTBURBONSA-N (3ar,7ar)-3-[1-[1-(cyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CCN1C(=O)C1CC1 ACVMDJFCEPWEDE-RTBURBONSA-N 0.000 claims 1
- GNIWETLLWMGHQG-NHCUHLMSSA-N (3ar,7ar)-3-[1-[1-[3-(2-oxopyrrolidin-1-yl)propanoyl]piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CCN1C(=O)CCN1CCCC1=O GNIWETLLWMGHQG-NHCUHLMSSA-N 0.000 claims 1
- CNPPMLHQUZNOFF-YKSBVNFPSA-N (3ar,7as)-1-[1-[1-(2-methylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-3h-indol-2-one Chemical compound CC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(C[C@H]3CCCC[C@@H]32)=O)CC1 CNPPMLHQUZNOFF-YKSBVNFPSA-N 0.000 claims 1
- DBWUZUSWJDAQMD-YADHBBJMSA-N (3as,7ar)-3-[1-(1-benzoylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1 DBWUZUSWJDAQMD-YADHBBJMSA-N 0.000 claims 1
- FMQGKZLVPYCWGW-PMACEKPBSA-N (3as,7as)-1-[1-[1-(3-methoxythiophene-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3-methyl-3a,4,5,6,7,7a-hexahydrobenzimidazol-2-one Chemical compound C1=CSC(C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N(C)[C@H]3CCCC[C@@H]32)=O)=C1OC FMQGKZLVPYCWGW-PMACEKPBSA-N 0.000 claims 1
- OFMSVAGCJZSCGP-PMACEKPBSA-N (3as,7as)-1-[1-[1-(cyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3-methyl-3a,4,5,6,7,7a-hexahydrobenzimidazol-2-one Chemical compound N1([C@H]2CCCC[C@@H]2N(C1=O)C)C(CC1)CCN1C(CC1)CCN1C(=O)C1CC1 OFMSVAGCJZSCGP-PMACEKPBSA-N 0.000 claims 1
- RZUTVWOSQTVGCZ-ZEQRLZLVSA-N (3as,7as)-1-methyl-3-[1-[1-(2-methylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydrobenzimidazol-2-one Chemical compound N1([C@H]2CCCC[C@@H]2N(C1=O)C)C(CC1)CCN1C(CC1)CCN1C(=O)C1=CC=CC=C1C RZUTVWOSQTVGCZ-ZEQRLZLVSA-N 0.000 claims 1
- JRWADFLOEGGLNP-VXKWHMMOSA-N (3as,7as)-1-methyl-3-[1-[1-[3-(2-oxopyrrolidin-1-yl)propanoyl]piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydrobenzimidazol-2-one Chemical compound N1([C@H]2CCCC[C@@H]2N(C1=O)C)C(CC1)CCN1C(CC1)CCN1C(=O)CCN1CCCC1=O JRWADFLOEGGLNP-VXKWHMMOSA-N 0.000 claims 1
- YKYIFBPVNIHHID-HOTGVXAUSA-N (3as,7as)-3-(1-piperidin-4-ylpiperidin-4-yl)-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound N1([C@H]2CCCC[C@@H]2NC1=O)C(CC1)CCN1C1CCNCC1 YKYIFBPVNIHHID-HOTGVXAUSA-N 0.000 claims 1
- LCIHDOOZKXOYAA-OALUTQOASA-N (3as,7as)-3-[1-(1-butanoylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)CCC)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 LCIHDOOZKXOYAA-OALUTQOASA-N 0.000 claims 1
- TXOFDYDHTGBFSI-OALUTQOASA-N (3as,7as)-3-[1-[1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1(C)CC1 TXOFDYDHTGBFSI-OALUTQOASA-N 0.000 claims 1
- CLYBZACMYSDIOQ-PMACEKPBSA-N (3as,7as)-3-[1-[1-(1-methylpyrrole-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CN1C=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 CLYBZACMYSDIOQ-PMACEKPBSA-N 0.000 claims 1
- YUOPUHPAOHYNNR-FQECFTEESA-N (3as,7as)-3-[1-[1-(2,2-difluorocyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound FC1(F)CC1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 YUOPUHPAOHYNNR-FQECFTEESA-N 0.000 claims 1
- SWJGZBJNGIXQFY-OALUTQOASA-N (3as,7as)-3-[1-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)C(C)(C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 SWJGZBJNGIXQFY-OALUTQOASA-N 0.000 claims 1
- KBLTWAQGHCHBCP-VXKWHMMOSA-N (3as,7as)-3-[1-[1-(2-chlorobenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound ClC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 KBLTWAQGHCHBCP-VXKWHMMOSA-N 0.000 claims 1
- HGQNZTNYMPWMTA-NSOVKSMOSA-N (3as,7as)-3-[1-[1-(2-cyclohexylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1C1CCCCC1 HGQNZTNYMPWMTA-NSOVKSMOSA-N 0.000 claims 1
- BKDCFHZJHGPZAG-VXKWHMMOSA-N (3as,7as)-3-[1-[1-(2-fluorobenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound FC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 BKDCFHZJHGPZAG-VXKWHMMOSA-N 0.000 claims 1
- CDHZCKYVYJFWIQ-VXKWHMMOSA-N (3as,7as)-3-[1-[1-(2-methoxybenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound COC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 CDHZCKYVYJFWIQ-VXKWHMMOSA-N 0.000 claims 1
- CEEPQONDLRSWHP-GOTSBHOMSA-N (3as,7as)-3-[1-[1-(2-methylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 CEEPQONDLRSWHP-GOTSBHOMSA-N 0.000 claims 1
- JNVGUNGAJYNXKS-YIGDWTTGSA-N (3as,7as)-3-[1-[1-(2-methylcyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CC1CC1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 JNVGUNGAJYNXKS-YIGDWTTGSA-N 0.000 claims 1
- SFKZMNQERBDWTD-OALUTQOASA-N (3as,7as)-3-[1-[1-(2-methylpropanoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)C(C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 SFKZMNQERBDWTD-OALUTQOASA-N 0.000 claims 1
- JYCQGNFNEBGBNB-AHWVRZQESA-N (3as,7as)-3-[1-[1-(2-morpholin-4-ylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1N1CCOCC1 JYCQGNFNEBGBNB-AHWVRZQESA-N 0.000 claims 1
- WDPWCQKKCSYSFN-NSOVKSMOSA-N (3as,7as)-3-[1-[1-(2-phenylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1C1=CC=CC=C1 WDPWCQKKCSYSFN-NSOVKSMOSA-N 0.000 claims 1
- CYEFUBXMFRJDMS-GOTSBHOMSA-N (3as,7as)-3-[1-[1-(2-propylpentanoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)C(CCC)CCC)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 CYEFUBXMFRJDMS-GOTSBHOMSA-N 0.000 claims 1
- FZOZQNJAAVKVOT-GOTSBHOMSA-N (3as,7as)-3-[1-[1-(3-methoxybenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound COC1=CC=CC(C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)=C1 FZOZQNJAAVKVOT-GOTSBHOMSA-N 0.000 claims 1
- CLOVXUMUVUNELE-OALUTQOASA-N (3as,7as)-3-[1-[1-(3-methoxythiophene-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1=CSC(C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)=C1OC CLOVXUMUVUNELE-OALUTQOASA-N 0.000 claims 1
- GDPVOBYRPRZLFB-PMACEKPBSA-N (3as,7as)-3-[1-[1-(3-methylbutanoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)CC(C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 GDPVOBYRPRZLFB-PMACEKPBSA-N 0.000 claims 1
- YGSAIPMMUUNJAB-PMACEKPBSA-N (3as,7as)-3-[1-[1-(3-methylfuran-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1=COC(C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)=C1C YGSAIPMMUUNJAB-PMACEKPBSA-N 0.000 claims 1
- SHQRUJGLGJBNCK-PMACEKPBSA-N (3as,7as)-3-[1-[1-(3-methylthiophene-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1=CSC(C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)=C1C SHQRUJGLGJBNCK-PMACEKPBSA-N 0.000 claims 1
- CVOKURJIAZYYGI-GOTSBHOMSA-N (3as,7as)-3-[1-[1-(4-methoxybenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 CVOKURJIAZYYGI-GOTSBHOMSA-N 0.000 claims 1
- WAVRRRRZOHOAAA-PMACEKPBSA-N (3as,7as)-3-[1-[1-(cyclobutanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1CCC1 WAVRRRRZOHOAAA-PMACEKPBSA-N 0.000 claims 1
- RIUYKDFTYOCUAI-VXKWHMMOSA-N (3as,7as)-3-[1-[1-(cyclohexanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1CCCCC1 RIUYKDFTYOCUAI-VXKWHMMOSA-N 0.000 claims 1
- HFTYBVTZIUWPKC-SFTDATJTSA-N (3as,7as)-3-[1-[1-(cyclopentanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1CCCC1 HFTYBVTZIUWPKC-SFTDATJTSA-N 0.000 claims 1
- ACVMDJFCEPWEDE-OALUTQOASA-N (3as,7as)-3-[1-[1-(cyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1CC1 ACVMDJFCEPWEDE-OALUTQOASA-N 0.000 claims 1
- DFSPYDUYYXGDBM-DQEYMECFSA-N (3as,7as)-3-[1-[1-(quinoline-4-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1=CC=C2C(C(N3CCC(CC3)N3CCC(CC3)N3C(N[C@H]4CCCC[C@@H]43)=O)=O)=CC=NC2=C1 DFSPYDUYYXGDBM-DQEYMECFSA-N 0.000 claims 1
- JVFARHQUXPIWSC-OALUTQOASA-N (3as,7as)-3-[1-[1-(thiophene-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CS1 JVFARHQUXPIWSC-OALUTQOASA-N 0.000 claims 1
- KNGBCSZKNUYXJV-ROUUACIJSA-N (3as,7as)-3-[1-[1-[1-(trifluoromethyl)cyclopropanecarbonyl]piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1(C(F)(F)F)CC1 KNGBCSZKNUYXJV-ROUUACIJSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims 1
- RWIIUBCMPVZLBA-UHFFFAOYSA-N 1,3,3a,4,5,6,7,7a-octahydrobenzimidazol-2-one Chemical compound C1CCCC2NC(=O)NC21 RWIIUBCMPVZLBA-UHFFFAOYSA-N 0.000 claims 1
- IWVLXAWCUVLTGS-GOTSBHOMSA-N 2-[4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carbonyl]benzonitrile Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1C#N IWVLXAWCUVLTGS-GOTSBHOMSA-N 0.000 claims 1
- XGGBTENKEWPYIR-ROUUACIJSA-N 2-fluoroethyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCCF)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 XGGBTENKEWPYIR-ROUUACIJSA-N 0.000 claims 1
- BIUQRDFLGXLVOH-PMACEKPBSA-N 2-methylpropyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC(C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 BIUQRDFLGXLVOH-PMACEKPBSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- SXVOJMDLKZHJBL-QZTJIDSGSA-N ethyl 4-[4-[(3ar,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 SXVOJMDLKZHJBL-QZTJIDSGSA-N 0.000 claims 1
- SXVOJMDLKZHJBL-MSOLQXFVSA-N ethyl 4-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1CCC(N2C(N[C@@H]3CCCC[C@@H]32)=O)CC1 SXVOJMDLKZHJBL-MSOLQXFVSA-N 0.000 claims 1
- SXVOJMDLKZHJBL-ZWKOTPCHSA-N ethyl 4-[4-[(3as,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1CCC(N2C(N[C@H]3CCCC[C@H]32)=O)CC1 SXVOJMDLKZHJBL-ZWKOTPCHSA-N 0.000 claims 1
- ZWZHLKCQSCOKOI-SFTDATJTSA-N ethyl 4-[4-[(3as,7as)-2-oxo-3-propan-2-yl-3a,4,5,6,7,7a-hexahydrobenzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1CCC(N2C(N(C(C)C)[C@H]3CCCC[C@@H]32)=O)CC1 ZWZHLKCQSCOKOI-SFTDATJTSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- DCAUAGVMSPDZLB-IRXDYDNUSA-N methyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 DCAUAGVMSPDZLB-IRXDYDNUSA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- MTVKPGFOMDTATR-OALUTQOASA-N prop-1-en-2-yl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(=C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 MTVKPGFOMDTATR-OALUTQOASA-N 0.000 claims 1
- PYJAXKIMFNHYSK-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]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 PYJAXKIMFNHYSK-RTBURBONSA-N 0.000 claims 1
- PYJAXKIMFNHYSK-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]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1N1CCC(N2C(N[C@@H]3CCCC[C@@H]32)=O)CC1 PYJAXKIMFNHYSK-MOPGFXCFSA-N 0.000 claims 1
- ATDYFOLFOQOQHV-XLIONFOSSA-N propan-2-yl 4-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-indol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1N1CCC(N2C(C[C@H]3CCCC[C@@H]32)=O)CC1 ATDYFOLFOQOQHV-XLIONFOSSA-N 0.000 claims 1
- PYJAXKIMFNHYSK-RBUKOAKNSA-N propan-2-yl 4-[4-[(3as,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@H]32)=O)CC1 PYJAXKIMFNHYSK-RBUKOAKNSA-N 0.000 claims 1
- PYJAXKIMFNHYSK-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]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 PYJAXKIMFNHYSK-OALUTQOASA-N 0.000 claims 1
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 0 CC(CCN(C)C(*)=O)N(CC1)CCC1N(C1C(*2)CCCC1)C2=O Chemical compound CC(CCN(C)C(*)=O)N(CC1)CCC1N(C1C(*2)CCCC1)C2=O 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
Applications Claiming Priority (2)
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|---|---|---|---|
| US81220906P | 2006-06-09 | 2006-06-09 | |
| PCT/SE2007/000554 WO2007142583A1 (en) | 2006-06-09 | 2007-06-08 | Muscarinic receptor agonists that are effective in the treatment of pain, alzheimer's disease and schizophrenia. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009539831A JP2009539831A (ja) | 2009-11-19 |
| JP2009539831A5 true JP2009539831A5 (https=) | 2010-07-22 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2009514231A Ceased JP2009539831A (ja) | 2006-06-09 | 2007-06-08 | 疼痛、アルツハイマー病および統合失調症の治療に有効なムスカリン受容体アゴニスト |
Country Status (18)
| Country | Link |
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| US (1) | US7956069B2 (https=) |
| EP (1) | EP2035411A1 (https=) |
| JP (1) | JP2009539831A (https=) |
| KR (1) | KR20090018210A (https=) |
| CN (1) | CN101501025A (https=) |
| AR (1) | AR061305A1 (https=) |
| AU (1) | AU2007256012A1 (https=) |
| BR (1) | BRPI0712331A2 (https=) |
| CA (1) | CA2654138A1 (https=) |
| EC (1) | ECSP088966A (https=) |
| IL (1) | IL195431A0 (https=) |
| MX (1) | MX2008015136A (https=) |
| NO (1) | NO20085270L (https=) |
| RU (1) | RU2008147542A (https=) |
| SA (1) | SA07280303B1 (https=) |
| TW (1) | TW200813018A (https=) |
| UY (1) | UY30397A1 (https=) |
| WO (1) | WO2007142583A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TW200815405A (en) * | 2006-06-09 | 2008-04-01 | Astrazeneca Ab | Novel compounds |
| US8119661B2 (en) * | 2007-09-11 | 2012-02-21 | Astrazeneca Ab | Piperidine derivatives and their use as muscarinic receptor modulators |
| UY31672A1 (es) * | 2008-02-28 | 2009-09-30 | "agonistas de receptores muscarínicos composiciones farmacéuticas métodos de tratamiento de los mismos, y procedimientos para su preparación" | |
| 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 |
| GB0817982D0 (en) * | 2008-10-01 | 2008-11-05 | Glaxo Group Ltd | Compounds |
| EP2398320A4 (en) * | 2009-02-19 | 2012-09-19 | Univ Vanderbilt | ALLOSTERIC ANTAGONISTS OF AMIDOBIPIPERIDINECARBOXYLATE M1, ANALOGUES AND DERIVATIVES THEREOF, AND METHODS FOR THEIR MANUFACTURE AND USE |
| US20100286124A1 (en) * | 2009-04-10 | 2010-11-11 | Auspex Pharmaceuticals, Inc. | Prop-2-yn-1-amine inhibitors of monoamine oxidase type b |
| RU2013114771A (ru) * | 2010-09-03 | 2014-10-10 | Янссен Фармацевтика Нв | Диамиды азетидинила как ингибиторы моноацилглицерол липазы |
| WO2014122474A1 (en) | 2013-02-07 | 2014-08-14 | Takeda Pharmaceutical Company Limited | Piperidin-1 -yl and azepin-1 -yl carboxylates as muscarinic m4 receptor agonists |
| EP3774746A1 (en) * | 2018-04-06 | 2021-02-17 | Aquinox Pharmaceuticals (Canada) Inc. | Indene derivatives useful in treating pain and inflammation |
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| 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 |
| ATE216580T1 (de) | 1993-07-16 | 2002-05-15 | Merck & Co Inc | Benzoxazinon- und benzopyrimidinon- piperidinyl- verbindungen als tokolytische oxytocin-rezeptor- antagonisten |
| JP2002515008A (ja) * | 1994-10-27 | 2002-05-21 | メルク エンド カンパニー インコーポレーテッド | ムスカリン・アンタゴニスト |
| 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 |
| AU2307999A (en) * | 1997-12-23 | 1999-07-12 | Alcon Laboratories, Inc. | Muscarinic agents and use thereof to treat glaucoma, myopia and various other conditions |
| JP2000323278A (ja) | 1999-05-14 | 2000-11-24 | Toray Ind Inc | 発光素子 |
| ATE275141T1 (de) | 1999-10-13 | 2004-09-15 | Banyu Pharma Co Ltd | Substituierte imidazolin-derivate |
| SE9904652D0 (sv) | 1999-12-17 | 1999-12-17 | Astra Pharma Prod | Novel Compounds |
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| JP2005532361A (ja) * | 2002-06-17 | 2005-10-27 | メルク エンド カムパニー インコーポレーテッド | 高眼圧症の治療用の眼科用組成物 |
| WO2004069828A1 (ja) * | 2003-02-04 | 2004-08-19 | Mitsubishi Pharma Corporation | ピペリジン化合物およびその医薬用途 |
| CA2524221A1 (en) | 2003-04-30 | 2004-11-18 | The Institutes For Pharmaceutical Discovery, Llc | Substituted heteroaryls as inhibitors of protein tyrosine phosphatases |
| US20050250794A1 (en) | 2003-12-19 | 2005-11-10 | Andrew Napper | Methods of treating a disorder |
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| AU2005249494A1 (en) * | 2004-05-28 | 2005-12-15 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
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| CA2581930A1 (en) | 2004-09-27 | 2006-04-06 | Jane Trepel | Modulating mxa expression |
| WO2006038594A1 (ja) | 2004-10-04 | 2006-04-13 | Ono Pharmaceutical Co., Ltd. | Ｎ型カルシウムチャネル阻害薬 |
| WO2006130469A1 (en) | 2005-05-27 | 2006-12-07 | Oregon Health & Science University | Stimulation of neurite outgrowth by small molecules |
| TW200815351A (en) | 2006-05-02 | 2008-04-01 | Astrazeneca Ab | Novel compounds |
| TW200815405A (en) | 2006-06-09 | 2008-04-01 | Astrazeneca Ab | Novel compounds |
| US8119661B2 (en) * | 2007-09-11 | 2012-02-21 | Astrazeneca Ab | Piperidine derivatives and their use as muscarinic receptor modulators |
| UY31672A1 (es) | 2008-02-28 | 2009-09-30 | "agonistas de receptores muscarínicos composiciones farmacéuticas métodos de tratamiento de los mismos, y procedimientos para su preparación" | |
| 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 |
-
2007
- 2007-05-29 TW TW096119135A patent/TW200813018A/zh unknown
- 2007-06-07 UY UY30397A patent/UY30397A1/es unknown
- 2007-06-08 AU AU2007256012A patent/AU2007256012A1/en not_active Abandoned
- 2007-06-08 RU RU2008147542/04A patent/RU2008147542A/ru not_active Application Discontinuation
- 2007-06-08 KR KR1020097000417A patent/KR20090018210A/ko not_active Withdrawn
- 2007-06-08 JP JP2009514231A patent/JP2009539831A/ja not_active Ceased
- 2007-06-08 CN CNA2007800295059A patent/CN101501025A/zh active Pending
- 2007-06-08 EP EP07748217A patent/EP2035411A1/en not_active Withdrawn
- 2007-06-08 WO PCT/SE2007/000554 patent/WO2007142583A1/en not_active Ceased
- 2007-06-08 MX MX2008015136A patent/MX2008015136A/es not_active Application Discontinuation
- 2007-06-08 US US11/760,011 patent/US7956069B2/en not_active Expired - Fee Related
- 2007-06-08 CA CA002654138A patent/CA2654138A1/en not_active Abandoned
- 2007-06-08 AR ARP070102507A patent/AR061305A1/es not_active Application Discontinuation
- 2007-06-08 BR BRPI0712331-0A patent/BRPI0712331A2/pt not_active IP Right Cessation
- 2007-06-09 SA SA7280303A patent/SA07280303B1/ar unknown
-
2008
- 2008-11-20 IL IL195431A patent/IL195431A0/en unknown
- 2008-12-12 EC EC2008008966A patent/ECSP088966A/es unknown
- 2008-12-16 NO NO20085270A patent/NO20085270L/no not_active Application Discontinuation
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