JP2008518890A5 - - Google Patents
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- Publication number
- JP2008518890A5 JP2008518890A5 JP2007538352A JP2007538352A JP2008518890A5 JP 2008518890 A5 JP2008518890 A5 JP 2008518890A5 JP 2007538352 A JP2007538352 A JP 2007538352A JP 2007538352 A JP2007538352 A JP 2007538352A JP 2008518890 A5 JP2008518890 A5 JP 2008518890A5
- Authority
- JP
- Japan
- Prior art keywords
- azonia
- bicyclo
- acetoxy
- hydroxy
- phenyl
- 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 description 15
- -1 1-ethyl Chemical group 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 4
- BDDIUTHMWNWMRJ-UHFFFAOYSA-N octane;hydrobromide Chemical compound Br.CCCCCCCC BDDIUTHMWNWMRJ-UHFFFAOYSA-N 0.000 claims 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- NNQWPPFQQVLUFE-UHFFFAOYSA-N octane;phosphoric acid Chemical compound OP(O)(O)=O.CCCCCCCC NNQWPPFQQVLUFE-UHFFFAOYSA-N 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- UFSPOLRWNODOPM-XEYCJBLXSA-O [(3r)-1-(2-amino-2-oxo-1-pyrimidin-4-ylethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-2-ylacetate Chemical compound C1CC([C@H](C2)OC(=O)C(O)(C3CCCCC3)C=3SC=CC=3)CC[N+]12C(C(=O)N)C1=CC=NC=N1 UFSPOLRWNODOPM-XEYCJBLXSA-O 0.000 claims 1
- HPYXAVWBFYPGII-MILPUHMWSA-O [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-bis(2-chlorophenyl)-2-hydroxyacetate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)C(O)(C=3C(=CC=CC=3)Cl)C=3C(=CC=CC=3)Cl)[N+]21CC(=O)NC=1C=CON=1 HPYXAVWBFYPGII-MILPUHMWSA-O 0.000 claims 1
- LYEUZKSCFWFFMP-OFIQDHIESA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-bis(2-chlorophenyl)-2-hydroxyacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C=3C(=CC=CC=3)Cl)C=3C(=CC=CC=3)Cl)[N+]21CC(=O)NC=1C=CON=1 LYEUZKSCFWFFMP-OFIQDHIESA-N 0.000 claims 1
- HZGHGUPFITZHEX-GXVQUIFISA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-diphenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(C1)CC(=O)NC1=NOC=C1)C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 HZGHGUPFITZHEX-GXVQUIFISA-N 0.000 claims 1
- DYJLKQXGEJBNTE-NGKDMHNESA-O [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-diphenylpropanoate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)C(C)(C=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CC(=O)NC=1C=CON=1 DYJLKQXGEJBNTE-NGKDMHNESA-O 0.000 claims 1
- QNGBQXNPFDMABV-WULMZJJMSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-diphenylpropanoate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(C)(C=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CC(=O)NC=1C=CON=1 QNGBQXNPFDMABV-WULMZJJMSA-N 0.000 claims 1
- XJQRRXDTQMFSPX-DQNCVNJQSA-O [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate Chemical compound O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 XJQRRXDTQMFSPX-DQNCVNJQSA-O 0.000 claims 1
- GRPDJYSPOSONBX-CXXVJMAYSA-O [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-2-ylacetate Chemical compound O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCCC1 GRPDJYSPOSONBX-CXXVJMAYSA-O 0.000 claims 1
- UYDZCDBOKNTCDY-NSLDKZMESA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCCC1 UYDZCDBOKNTCDY-NSLDKZMESA-N 0.000 claims 1
- OPKZTANCWQVQNS-CHPMHQDOSA-O [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate Chemical compound O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 OPKZTANCWQVQNS-CHPMHQDOSA-O 0.000 claims 1
- IPYXMSOXADDKER-SUSCGCCGSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 IPYXMSOXADDKER-SUSCGCCGSA-N 0.000 claims 1
- QKWYYKNTCJWPIW-VWNNWTLOSA-O [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate Chemical compound O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCC1 QKWYYKNTCJWPIW-VWNNWTLOSA-O 0.000 claims 1
- PFNWPHKQGJNTSN-UTEXUTGQSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCC1 PFNWPHKQGJNTSN-UTEXUTGQSA-N 0.000 claims 1
- YAQGWYFZNASGCH-UYXPAWESSA-O [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-bis(4-methylphenyl)acetate Chemical compound C1=CC(C)=CC=C1C(O)(C=1C=CC(C)=CC=1)C(=O)O[C@@H]1C(CC2)CC[N+]2(CC(=O)NC2=NOC=C2)C1 YAQGWYFZNASGCH-UYXPAWESSA-O 0.000 claims 1
- LMVPTKHKZQNMTP-DMWRAEOSSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-bis(4-methylphenyl)acetate;bromide Chemical compound [Br-].C1=CC(C)=CC=C1C(O)(C=1C=CC(C)=CC=1)C(=O)O[C@@H]1C(CC2)CC[N+]2(CC(=O)NC2=NOC=C2)C1 LMVPTKHKZQNMTP-DMWRAEOSSA-N 0.000 claims 1
- QGEDBQACWDBQMA-BQNWASQZSA-O [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-(2-methylphenyl)-2-phenylacetate Chemical compound CC1=CC=CC=C1C(O)(C=1C=CC=CC=1)C(=O)O[C@@H]1C(CC2)CC[N+]2(CC(=O)NC2=NOC=C2)C1 QGEDBQACWDBQMA-BQNWASQZSA-O 0.000 claims 1
- SQKMLNPPWDJIOV-KNNDMWINSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-(2-methylphenyl)-2-phenylacetate;bromide Chemical compound [Br-].CC1=CC=CC=C1C(O)(C=1C=CC=CC=1)C(=O)O[C@@H]1C(CC2)CC[N+]2(CC(=O)NC2=NOC=C2)C1 SQKMLNPPWDJIOV-KNNDMWINSA-N 0.000 claims 1
- JFEYVAIZYICFSH-NGKDMHNESA-O [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-methoxy-2,2-diphenylacetate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)C(OC)(C=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CC(=O)NC=1C=CON=1 JFEYVAIZYICFSH-NGKDMHNESA-O 0.000 claims 1
- QJIBWXVASULUCW-WULMZJJMSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-methoxy-2,2-diphenylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(OC)(C=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CC(=O)NC=1C=CON=1 QJIBWXVASULUCW-WULMZJJMSA-N 0.000 claims 1
- REAAZRXMTNPMKU-CLPKMKQYSA-O [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate Chemical compound O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=NC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 REAAZRXMTNPMKU-CLPKMKQYSA-O 0.000 claims 1
- VTFGHQOKBDCJRA-WNCQOFSISA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=NC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 VTFGHQOKBDCJRA-WNCQOFSISA-N 0.000 claims 1
- QHXGSRAXXWHYPW-SSPRTNKYSA-O [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate Chemical compound O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=NC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 QHXGSRAXXWHYPW-SSPRTNKYSA-O 0.000 claims 1
- DQWQUUWAYXIMGT-ZVPZRTFFSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=NC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 DQWQUUWAYXIMGT-ZVPZRTFFSA-N 0.000 claims 1
- ZYOJAGYMAGTXMP-QDBCHFMASA-O [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate Chemical compound O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=NC=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCC1 ZYOJAGYMAGTXMP-QDBCHFMASA-O 0.000 claims 1
- CFMGCNDIOKQGHM-AYFIPJBYSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=NC=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCC1 CFMGCNDIOKQGHM-AYFIPJBYSA-N 0.000 claims 1
- VPTKBULFHLYZHD-CLPKMKQYSA-O [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate Chemical compound O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 VPTKBULFHLYZHD-CLPKMKQYSA-O 0.000 claims 1
- VBIYLYUWXZELLQ-WNCQOFSISA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 VBIYLYUWXZELLQ-WNCQOFSISA-N 0.000 claims 1
- NWPFZFYKYBIFAJ-SSPRTNKYSA-O [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate Chemical compound O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 NWPFZFYKYBIFAJ-SSPRTNKYSA-O 0.000 claims 1
- QGJDAWHXJGNHNS-ZVPZRTFFSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 QGJDAWHXJGNHNS-ZVPZRTFFSA-N 0.000 claims 1
- YOUZWXDYCYBCBI-QDBCHFMASA-O [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate Chemical compound O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCC1 YOUZWXDYCYBCBI-QDBCHFMASA-O 0.000 claims 1
- NINFWSUPOJXCOM-AYFIPJBYSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCC1 NINFWSUPOJXCOM-AYFIPJBYSA-N 0.000 claims 1
- IEPDOGMLEYKOGZ-DQHVLQIQSA-O [(3r)-1-[2-oxo-2-[(4-phenyl-1,2-oxazol-3-yl)amino]ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate Chemical compound O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2C(=CON=2)C=2C=CC=CC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 IEPDOGMLEYKOGZ-DQHVLQIQSA-O 0.000 claims 1
- KVRBYPPMUIHVSM-NXCMLHJESA-N [(3r)-1-[2-oxo-2-[(4-phenyl-1,2-oxazol-3-yl)amino]ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2C(=CON=2)C=2C=CC=CC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 KVRBYPPMUIHVSM-NXCMLHJESA-N 0.000 claims 1
- KWOSOGIXVROBEO-RSYBFYOOSA-N [O-]P([O-])([O-])=O.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=CC=CC=2)CCCCC1.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=CC=CC=2)CCCCC1.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=CC=CC=2)CCCCC1 Chemical compound [O-]P([O-])([O-])=O.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=CC=CC=2)CCCCC1.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=CC=CC=2)CCCCC1.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=CC=CC=2)CCCCC1 KWOSOGIXVROBEO-RSYBFYOOSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 150000003839 salts Chemical group 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 238000003556 assay Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0424284.8 | 2004-11-02 | ||
| GBGB0424284.8A GB0424284D0 (en) | 2004-11-02 | 2004-11-02 | Organic compounds |
| PCT/EP2005/011662 WO2006048225A1 (en) | 2004-11-02 | 2005-10-31 | Quinuclidine derivatives and their use as muscarinic m3 receptor antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008518890A JP2008518890A (ja) | 2008-06-05 |
| JP2008518890A5 true JP2008518890A5 (OSRAM) | 2012-03-15 |
| JP4950896B2 JP4950896B2 (ja) | 2012-06-13 |
Family
ID=33515948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007538352A Expired - Fee Related JP4950896B2 (ja) | 2004-11-02 | 2005-10-31 | ムスカリンｍ３受容体アンタゴニストとしてのキヌクリジン誘導体およびその使用 |
Country Status (33)
| Country | Link |
|---|---|
| US (2) | US7723356B2 (OSRAM) |
| EP (2) | EP2206499A1 (OSRAM) |
| JP (1) | JP4950896B2 (OSRAM) |
| KR (1) | KR101252307B1 (OSRAM) |
| CN (1) | CN101056634B (OSRAM) |
| AR (1) | AR054090A1 (OSRAM) |
| AT (1) | ATE481099T1 (OSRAM) |
| AU (1) | AU2005300710B2 (OSRAM) |
| BR (1) | BRPI0517945A (OSRAM) |
| CA (1) | CA2583237C (OSRAM) |
| CY (1) | CY1110952T1 (OSRAM) |
| DE (1) | DE602005023639D1 (OSRAM) |
| DK (1) | DK1811999T3 (OSRAM) |
| EC (1) | ECSP077424A (OSRAM) |
| ES (1) | ES2353142T3 (OSRAM) |
| GB (1) | GB0424284D0 (OSRAM) |
| HR (1) | HRP20100693T1 (OSRAM) |
| IL (1) | IL182695A0 (OSRAM) |
| JO (1) | JO2613B1 (OSRAM) |
| MA (1) | MA29080B1 (OSRAM) |
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