NO328707B1 - Quinuklidin-karbamat-derivater samt medisinske sammensetninger omfattende slike - Google Patents
Quinuklidin-karbamat-derivater samt medisinske sammensetninger omfattende slike Download PDFInfo
- Publication number
- NO328707B1 NO328707B1 NO20032889A NO20032889A NO328707B1 NO 328707 B1 NO328707 B1 NO 328707B1 NO 20032889 A NO20032889 A NO 20032889A NO 20032889 A NO20032889 A NO 20032889A NO 328707 B1 NO328707 B1 NO 328707B1
- Authority
- NO
- Norway
- Prior art keywords
- octane
- azoniabicyclo
- group
- bromide
- azabicyclo
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title description 24
- DSTLXMSUVMLNBP-UHFFFAOYSA-N 1-azoniabicyclo[2.2.2]octane;carbamate Chemical class NC(O)=O.C1CC2CCN1CC2 DSTLXMSUVMLNBP-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 243
- 238000000034 method Methods 0.000 claims description 191
- -1 furan-2-ylmethyl Chemical group 0.000 claims description 129
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 127
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 23
- 208000023504 respiratory system disease Diseases 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 7
- 150000003431 steroids Chemical class 0.000 claims description 7
- 208000014001 urinary system disease Diseases 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 102000007202 Muscarinic M3 Receptor Human genes 0.000 claims description 6
- 108010008405 Muscarinic M3 Receptor Proteins 0.000 claims description 6
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims description 6
- 230000000241 respiratory effect Effects 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- VRZIYMYSNOVVOK-KRWDZBQOSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n,n-bis(thiophen-2-ylmethyl)carbamate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)N(CC=1SC=CC=1)CC1=CC=CS1 VRZIYMYSNOVVOK-KRWDZBQOSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 230000003266 anti-allergic effect Effects 0.000 claims description 4
- WKFZHVFBHYHYAK-UHFFFAOYSA-N benzyl(phenyl)carbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)CC1=CC=CC=C1 WKFZHVFBHYHYAK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- QLPCBFZOKBZFEV-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-yl n-benzyl-n-phenylcarbamate Chemical compound C1CN(CC2)CCC12OC(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 QLPCBFZOKBZFEV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 208000012931 Urologic disease Diseases 0.000 claims description 3
- 208000010643 digestive system disease Diseases 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 208000018685 gastrointestinal system disease Diseases 0.000 claims description 3
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 238000002414 normal-phase solid-phase extraction Methods 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- TXFPDUVPZSZURQ-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-benzyl-n-phenylcarbamate;hydrochloride Chemical compound Cl.C1N(CC2)CCC2C1OC(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 TXFPDUVPZSZURQ-UHFFFAOYSA-N 0.000 claims description 2
- HSGQPXOPCPJENX-CCOWBORGSA-M [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(thiophen-2-ylmethyl)carbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CC=3SC=CC=3)C=3C=CC=CC=3)[N+]21CCOC1=CC=CC=C1 HSGQPXOPCPJENX-CCOWBORGSA-M 0.000 claims description 2
- RUMIBZGNGQBYPD-DSSKCDFUSA-M [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(thiophen-3-ylmethyl)carbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CC3=CSC=C3)C=3C=CC=CC=3)[N+]21CCOC1=CC=CC=C1 RUMIBZGNGQBYPD-DSSKCDFUSA-M 0.000 claims description 2
- RFHYCEHWBDUMOY-AEDYTTQKSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-(furan-2-ylmethyl)-n-phenylcarbamate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C([C@@H](C(CC1)CC2)OC(=O)N(CC=3OC=CC=3)C=3C=CC=CC=3)[N+]21CCCC1=CC=CC=C1 RFHYCEHWBDUMOY-AEDYTTQKSA-M 0.000 claims description 2
- GNNJTNLPQMHFBR-DSSKCDFUSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-cyclopentyl-n-(thiophen-2-ylmethyl)carbamate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C([C@@H](C(CC1)CC2)OC(=O)N(CC=3SC=CC=3)C3CCCC3)[N+]21CCCC1=CC=CC=C1 GNNJTNLPQMHFBR-DSSKCDFUSA-M 0.000 claims description 2
- OEHUXJMRJMPURF-MNFPOUGWSA-M [(3r)-1-[3-(4-fluorophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CCCC)C=3C=CC=CC=3)[N+]21CCCOC1=CC=C(F)C=C1 OEHUXJMRJMPURF-MNFPOUGWSA-M 0.000 claims description 2
- VMIBAMSECPDFRO-KRWDZBQOSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n,n-bis(furan-2-ylmethyl)carbamate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)N(CC=1OC=CC=1)CC1=CC=CO1 VMIBAMSECPDFRO-KRWDZBQOSA-N 0.000 claims description 2
- DAZOPBNVULHBMK-WPNSFFRFSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(2-phenylethyl)carbamate;[(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(thiophen-2-ylmethyl)carbamate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)N(C=1C=CC=CC=1)CC1=CC=CS1.O([C@@H]1C2CCN(CC2)C1)C(=O)N(C=1C=CC=CC=1)CCC1=CC=CC=C1 DAZOPBNVULHBMK-WPNSFFRFSA-N 0.000 claims description 2
- 229940124748 beta 2 agonist Drugs 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 239000013066 combination product Substances 0.000 claims description 2
- 229940127555 combination product Drugs 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- GDLWJBJOVTYAJR-GSEXTUOBSA-M [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CCOC1=CC=CC=C1 GDLWJBJOVTYAJR-GSEXTUOBSA-M 0.000 claims 1
- JZCRAMPGFZJPOE-ZZNGFPBBSA-M [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CCCC)C=3C=CC=CC=3)[N+]21CCOC1=CC=CC=C1 JZCRAMPGFZJPOE-ZZNGFPBBSA-M 0.000 claims 1
- MSEFDPBADMQKQW-RARKWRLQSA-M [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(2-phenylethyl)carbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CCC=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CCOC1=CC=CC=C1 MSEFDPBADMQKQW-RARKWRLQSA-M 0.000 claims 1
- PIJFPTVLIXOHMJ-DSSKCDFUSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n,n-bis(thiophen-2-ylmethyl)carbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CC=3SC=CC=3)CC=3SC=CC=3)[N+]21CCCC1=CC=CC=C1 PIJFPTVLIXOHMJ-DSSKCDFUSA-M 0.000 claims 1
- PNWQOMABRMWDMF-LVKSKBLHSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CCCC1=CC=CC=C1 PNWQOMABRMWDMF-LVKSKBLHSA-M 0.000 claims 1
- ZEKWXBFSCSXDLQ-NRMJQQDLSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CCCC)C=3C=CC=CC=3)[N+]21CCCC1=CC=CC=C1 ZEKWXBFSCSXDLQ-NRMJQQDLSA-M 0.000 claims 1
- ROECTEAZZKLWOE-MSZWFKHVSA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n,n-bis(thiophen-2-ylmethyl)carbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CC=3SC=CC=3)CC=3SC=CC=3)[N+]21CCCC1=CC=CS1 ROECTEAZZKLWOE-MSZWFKHVSA-M 0.000 claims 1
- MCGSMQKZGMDZFT-AEDYTTQKSA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CCCC1=CC=CS1 MCGSMQKZGMDZFT-AEDYTTQKSA-M 0.000 claims 1
- FHESLQGDLROIOJ-SSVLGJNASA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CCCC)C=3C=CC=CC=3)[N+]21CCCC1=CC=CS1 FHESLQGDLROIOJ-SSVLGJNASA-M 0.000 claims 1
- NBAFBTBCPVIPLO-OCJYMVTRSA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(thiophen-2-ylmethyl)carbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CC=3SC=CC=3)C=3C=CC=CC=3)[N+]21CCCC1=CC=CS1 NBAFBTBCPVIPLO-OCJYMVTRSA-M 0.000 claims 1
- WUXTWVZFGDCASM-ZZNGFPBBSA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(thiophen-3-ylmethyl)carbamate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C([C@@H](C(CC1)CC2)OC(=O)N(CC3=CSC=C3)C=3C=CC=CC=3)[N+]21CCCC1=CC=CS1 WUXTWVZFGDCASM-ZZNGFPBBSA-M 0.000 claims 1
- RRDGGSLRLZXWCU-CCOWBORGSA-N [(3r)-1-[3-(3-hydroxyphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)N(CCCC)C=3C=CC=CC=3)[N+]21CCCOC1=CC=CC(O)=C1 RRDGGSLRLZXWCU-CCOWBORGSA-N 0.000 claims 1
- XPVJWYRFNSRXMP-NRYUZRROSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-cyclopentyl-n-(thiophen-2-ylmethyl)carbamate;[(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-(furan-2-ylmethyl)-n-phenylcarbamate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)N(C1CCCC1)CC1=CC=CS1.O([C@@H]1C2CCN(CC2)C1)C(=O)N(C=1C=CC=CC=1)CC1=CC=CO1 XPVJWYRFNSRXMP-NRYUZRROSA-N 0.000 claims 1
- SRSDGJOKLMADHL-SFHVURJKSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-pentyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)N(CCCCC)C1=CC=CC=C1 SRSDGJOKLMADHL-SFHVURJKSA-N 0.000 claims 1
- QPRWDHVZZSSIHZ-QMAMVGRZSA-M [Br-].C1CC([C@H](C2)OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 Chemical compound [Br-].C1CC([C@H](C2)OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 QPRWDHVZZSSIHZ-QMAMVGRZSA-M 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 80
- 238000005481 NMR spectroscopy Methods 0.000 description 30
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000725 suspension Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000003826 tablet Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 6
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 230000027455 binding Effects 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 230000002485 urinary effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- LQYINUYCLXSNNX-KGBLJUBMSA-N [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(thiophen-3-ylmethyl)carbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CC3=CSC=C3)C=3C=CC=CC=3)[N+]21CCCC1=CC=CC=C1 LQYINUYCLXSNNX-KGBLJUBMSA-N 0.000 description 1
- DQUOPWPTYBNISH-IIIFQBMYSA-N [(3r)-1-(3-phenylsulfanylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CCCSC1=CC=CC=C1 DQUOPWPTYBNISH-IIIFQBMYSA-N 0.000 description 1
- KRQWWJKJMBKOEK-IYUIPRCHSA-N [(3r)-1-(3-pyrrol-1-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CCCC)C=3C=CC=CC=3)[N+]21CCCN1C=CC=C1 KRQWWJKJMBKOEK-IYUIPRCHSA-N 0.000 description 1
- XHONDBFNYXSIDM-OKBRVIPFSA-N [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-pent-4-enyl-n-phenylcarbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CCCC=C)C=3C=CC=CC=3)[N+]21CCCC1=CC=CS1 XHONDBFNYXSIDM-OKBRVIPFSA-N 0.000 description 1
- GHGXEKZZCDTJHT-OKBRVIPFSA-N [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-pentyl-n-phenylcarbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CCCCC)C=3C=CC=CC=3)[N+]21CCCC1=CC=CS1 GHGXEKZZCDTJHT-OKBRVIPFSA-N 0.000 description 1
- BOUIEQCLPBGZOL-GPQFNORQSA-N [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(2-phenylethyl)carbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CCC=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CCCC1=CC=CS1 BOUIEQCLPBGZOL-GPQFNORQSA-N 0.000 description 1
- WZOMXRTVBFDJPD-MUZWYTLNSA-N [(3r)-1-(4-methylpent-3-enyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CCC=C(C)C)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 WZOMXRTVBFDJPD-MUZWYTLNSA-N 0.000 description 1
- BIGKVGNUQGNIIK-JEPVQIMHSA-N [(3r)-1-(4-methylpent-3-enyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(CCC=C(C)C)C1)C(=O)N(CCCC)C1=CC=CC=C1 BIGKVGNUQGNIIK-JEPVQIMHSA-N 0.000 description 1
- VJWIOXAVZUSCES-GEMBBTIOSA-N [(3r)-1-(4-oxo-4-phenylbutyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CCCC(=O)C=1C=CC=CC=1)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 VJWIOXAVZUSCES-GEMBBTIOSA-N 0.000 description 1
- PBEUVUYKCAADTE-FYKVLBHHSA-N [(3r)-1-(4-oxo-4-thiophen-2-ylbutyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CCCC(=O)C=1SC=CC=1)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 PBEUVUYKCAADTE-FYKVLBHHSA-N 0.000 description 1
- MXWTXHAECXYZMB-CJQCTXEWSA-N [(3r)-1-(4-oxo-4-thiophen-2-ylbutyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CCCC)C=3C=CC=CC=3)[N+]21CCCC(=O)C1=CC=CS1 MXWTXHAECXYZMB-CJQCTXEWSA-N 0.000 description 1
- HLVAALPZDHYGFR-FUFAFYGISA-N [(3r)-1-(4-phenylbutyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CCCCC1=CC=CC=C1 HLVAALPZDHYGFR-FUFAFYGISA-N 0.000 description 1
- KRFAYJZMZMKWAE-KGBLJUBMSA-N [(3r)-1-(4-phenylbutyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CCCC)C=3C=CC=CC=3)[N+]21CCCCC1=CC=CC=C1 KRFAYJZMZMKWAE-KGBLJUBMSA-N 0.000 description 1
- PANZZNJSRYFNJN-CRIAOJQNSA-N [(3r)-1-(cyclopropylmethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CC1CC1 PANZZNJSRYFNJN-CRIAOJQNSA-N 0.000 description 1
- AQQCLPGRJNJCHI-RXFKJLCSSA-N [(3r)-1-[2-(2-methoxyethoxy)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CCOCCOC)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 AQQCLPGRJNJCHI-RXFKJLCSSA-N 0.000 description 1
- SAQHUZWTXIFWGY-CVCZCXRASA-N [(3r)-1-[2-(2-methoxyethoxy)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(CCOCCOC)C1)C(=O)N(CCCC)C1=CC=CC=C1 SAQHUZWTXIFWGY-CVCZCXRASA-N 0.000 description 1
- UYMHACUGWKANKD-HLJRPHAASA-N [(3r)-1-[3-(1,3-benzodioxol-5-yloxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(CCCOC=2C=C3OCOC3=CC=2)C1)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 UYMHACUGWKANKD-HLJRPHAASA-N 0.000 description 1
- FFARTKVMUGKDJW-JWNAFBRWSA-N [(3r)-1-[3-(2,4,6-trimethylphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound CC1=CC(C)=CC(C)=C1OCCC[N+]1(C[C@@H]2OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)CCC2CC1 FFARTKVMUGKDJW-JWNAFBRWSA-N 0.000 description 1
- PWLNYYLLSJKGPC-JCBDZXOXSA-N [(3r)-1-[3-(2,4-difluorophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound FC1=CC(F)=CC=C1OCCC[N+]1(C[C@@H]2OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)CCC2CC1 PWLNYYLLSJKGPC-JCBDZXOXSA-N 0.000 description 1
- FAVVGJGQYQWYFV-PGSWAALUSA-O [(3r)-1-[3-(2-carbamoylphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound NC(=O)C1=CC=CC=C1OCCC[N+]1(C[C@@H]2OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)CCC2CC1 FAVVGJGQYQWYFV-PGSWAALUSA-O 0.000 description 1
- CUFYKVLCPCKODY-PAQIEUDPSA-N [(3r)-1-[3-(2-chlorophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound ClC1=CC=CC=C1OCCC[N+]1(C[C@@H]2OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)CCC2CC1 CUFYKVLCPCKODY-PAQIEUDPSA-N 0.000 description 1
- ZMYAWMOOPIUDQM-YGRPKTSXSA-N [(3r)-1-[3-(3-cyanophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CCCOC1=CC=CC(C#N)=C1 ZMYAWMOOPIUDQM-YGRPKTSXSA-N 0.000 description 1
- YCWQBKLGBCCWNC-KCTUUFLGSA-O [(3r)-1-[3-(3-hydroxyphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound OC1=CC=CC(OCCC[N+]23CCC(CC2)[C@H](C3)OC(=O)N(CC=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YCWQBKLGBCCWNC-KCTUUFLGSA-O 0.000 description 1
- JHKMWVOLJZNNLJ-VTIINTLQSA-O [(3r)-1-[3-(3-hydroxyphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-pent-4-enyl-n-phenylcarbamate Chemical compound OC1=CC=CC(OCCC[N+]23CCC(CC2)[C@H](C3)OC(=O)N(CCCC=C)C=2C=CC=CC=2)=C1 JHKMWVOLJZNNLJ-VTIINTLQSA-O 0.000 description 1
- DBWGXIVARZJXDU-VTIINTLQSA-O [(3r)-1-[3-(3-hydroxyphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-pentyl-n-phenylcarbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CCCCC)C=3C=CC=CC=3)[N+]21CCCOC1=CC=CC(O)=C1 DBWGXIVARZJXDU-VTIINTLQSA-O 0.000 description 1
- DONMTVHZXYHUGU-GYNTZMJKSA-O [(3r)-1-[3-(3-hydroxyphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(2-phenylethyl)carbamate Chemical compound OC1=CC=CC(OCCC[N+]23CCC(CC2)[C@H](C3)OC(=O)N(CCC=2C=CC=CC=2)C=2C=CC=CC=2)=C1 DONMTVHZXYHUGU-GYNTZMJKSA-O 0.000 description 1
- CXTDREZIFCNIQA-AUSLDBMVSA-O [(3r)-1-[3-(3-hydroxyphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(thiophen-2-ylmethyl)carbamate Chemical compound OC1=CC=CC(OCCC[N+]23CCC(CC2)[C@H](C3)OC(=O)N(CC=2SC=CC=2)C=2C=CC=CC=2)=C1 CXTDREZIFCNIQA-AUSLDBMVSA-O 0.000 description 1
- OLZIGXQADUFNMR-VTIINTLQSA-O [(3r)-1-[3-(3-hydroxyphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(thiophen-3-ylmethyl)carbamate Chemical compound OC1=CC=CC(OCCC[N+]23CCC(CC2)[C@H](C3)OC(=O)N(CC2=CSC=C2)C=2C=CC=CC=2)=C1 OLZIGXQADUFNMR-VTIINTLQSA-O 0.000 description 1
- IOEQBIZZTMJIOX-OGQZCOGXSA-O [(3r)-1-[3-(4-acetamidophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound C1=CC(NC(=O)C)=CC=C1OCCC[N+]1(C[C@@H]2OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)CCC2CC1 IOEQBIZZTMJIOX-OGQZCOGXSA-O 0.000 description 1
- HWEHPSONIGSNOS-PAQIEUDPSA-N [(3r)-1-[3-(4-fluorophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound C1=CC(F)=CC=C1OCCC[N+]1(C[C@@H]2OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)CCC2CC1 HWEHPSONIGSNOS-PAQIEUDPSA-N 0.000 description 1
- WRFYJTUKCQJARJ-VOHYGNEJSA-N [(3r)-1-[3-(4-fluorophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CCCC)C=3C=CC=CC=3)[N+]21CCCOC1=CC=C(F)C=C1 WRFYJTUKCQJARJ-VOHYGNEJSA-N 0.000 description 1
- NMVSLNFFVPUNBH-GYNTZMJKSA-N [(3r)-1-[3-(4-methoxyphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound C1=CC(OC)=CC=C1OCCC[N+]1(C[C@@H]2OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)CCC2CC1 NMVSLNFFVPUNBH-GYNTZMJKSA-N 0.000 description 1
- HNJJZBGQKLSMEJ-PAQIEUDPSA-N [(3r)-1-[3-(4-nitrophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OCCC[N+]1(C[C@@H]2OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)CCC2CC1 HNJJZBGQKLSMEJ-PAQIEUDPSA-N 0.000 description 1
- WINGGJASQUSDDW-BWFJTVLFSA-N [(3r)-1-[3-(4-phenylphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CCCOC(C=C1)=CC=C1C1=CC=CC=C1 WINGGJASQUSDDW-BWFJTVLFSA-N 0.000 description 1
- OAUGUNJWIHEVGN-YFGMWWGUSA-N [(3r)-1-[3-(5,6,7,8-tetrahydronaphthalen-2-yloxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(CCCOC=2C=C3CCCCC3=CC=2)C1)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 OAUGUNJWIHEVGN-YFGMWWGUSA-N 0.000 description 1
- NJLRKWWHEPWZAQ-YGRPKTSXSA-N [(3r)-1-[3-(n-methylanilino)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CCCN(C)C=1C=CC=CC=1)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 NJLRKWWHEPWZAQ-YGRPKTSXSA-N 0.000 description 1
- WOLZQBNTZSFZDY-OGQZCOGXSA-N [(3r)-1-[3-[3-(dimethylamino)phenoxy]propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound CN(C)C1=CC=CC(OCCC[N+]23CCC(CC2)[C@H](C3)OC(=O)N(CC=2C=CC=CC=2)C=2C=CC=CC=2)=C1 WOLZQBNTZSFZDY-OGQZCOGXSA-N 0.000 description 1
- UJZOYTRXQXQLMV-YQUUDUBZSA-N [(3r)-1-[3-[3-(trifluoromethyl)phenoxy]propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound FC(F)(F)C1=CC=CC(OCCC[N+]23CCC(CC2)[C@H](C3)OC(=O)N(CC=2C=CC=CC=2)C=2C=CC=CC=2)=C1 UJZOYTRXQXQLMV-YQUUDUBZSA-N 0.000 description 1
- AMYPPPYVTXQXKB-GEMBBTIOSA-N [(3r)-1-[3-[4-(hydroxymethyl)phenoxy]propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound C1=CC(CO)=CC=C1OCCC[N+]1(C[C@@H]2OC(=O)N(CC=3C=CC=CC=3)C=3C=CC=CC=3)CCC2CC1 AMYPPPYVTXQXKB-GEMBBTIOSA-N 0.000 description 1
- DUVRCCCAGVFLMM-FQEVSTJZSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-benzyl-n-(4-fluorophenyl)carbamate Chemical compound C1=CC(F)=CC=C1N(C(=O)O[C@@H]1C2CCN(CC2)C1)CC1=CC=CC=C1 DUVRCCCAGVFLMM-FQEVSTJZSA-N 0.000 description 1
- SNNFRAGGSGAUHH-NRFANRHFSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-benzyl-n-(4-methylphenyl)carbamate Chemical compound C1=CC(C)=CC=C1N(C(=O)O[C@@H]1C2CCN(CC2)C1)CC1=CC=CC=C1 SNNFRAGGSGAUHH-NRFANRHFSA-N 0.000 description 1
- BDLKVZCRRROJRY-FQEVSTJZSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 BDLKVZCRRROJRY-FQEVSTJZSA-N 0.000 description 1
- KNBSJPRRHIODSI-KRWDZBQOSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-butyl-n-(4-fluorophenyl)carbamate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)N(CCCC)C1=CC=C(F)C=C1 KNBSJPRRHIODSI-KRWDZBQOSA-N 0.000 description 1
- LIAJJEHSFRHBLC-KRWDZBQOSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)N(CCCC)C1=CC=CC=C1 LIAJJEHSFRHBLC-KRWDZBQOSA-N 0.000 description 1
- HBVQDYSCZMLKJI-SFHVURJKSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-pent-4-enyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)N(CCCC=C)C1=CC=CC=C1 HBVQDYSCZMLKJI-SFHVURJKSA-N 0.000 description 1
- FJVQALKRJDSNIH-SFHVURJKSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(thiophen-2-ylmethyl)carbamate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)N(C=1C=CC=CC=1)CC1=CC=CS1 FJVQALKRJDSNIH-SFHVURJKSA-N 0.000 description 1
- OYPHGGHOVVOVKM-KGBLJUBMSA-N [(3r)-1-heptyl-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CCCCCCC)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 OYPHGGHOVVOVKM-KGBLJUBMSA-N 0.000 description 1
- FMSQASUZXQGXMN-CRIAOJQNSA-N [(3r)-1-heptyl-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CCCCCCC)C(=O)N(CCCC)C1=CC=CC=C1 FMSQASUZXQGXMN-CRIAOJQNSA-N 0.000 description 1
- ZBDPTPGWTQLPMM-MMPATGFWSA-N [(3r)-1-methyl-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)C)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 ZBDPTPGWTQLPMM-MMPATGFWSA-N 0.000 description 1
- KWXUBQOLGJJRDI-JGCRXCKMSA-N [(3r)-1-methyl-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(C)C1)C(=O)N(CCCC)C1=CC=CC=C1 KWXUBQOLGJJRDI-JGCRXCKMSA-N 0.000 description 1
- XAPJEQRFWBXQJS-JEPVQIMHSA-N [(3r)-1-propan-2-yl-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)C(C)C)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 XAPJEQRFWBXQJS-JEPVQIMHSA-N 0.000 description 1
- RBWNIIRYXXFSSA-WWAKMMQFSA-N [(3r)-1-propan-2-yl-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)C(C)C)C(=O)N(CCCC)C1=CC=CC=C1 RBWNIIRYXXFSSA-WWAKMMQFSA-N 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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- Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Heart & Thoracic Surgery (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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ES200003084 | 2000-12-22 | ||
PCT/EP2001/015169 WO2002051841A1 (en) | 2000-12-22 | 2001-12-20 | Quinuclidine carbamate derivatives and their use as m3 antagonists |
Publications (3)
Publication Number | Publication Date |
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NO20032889D0 NO20032889D0 (no) | 2003-06-23 |
NO20032889L NO20032889L (no) | 2003-08-08 |
NO328707B1 true NO328707B1 (no) | 2010-05-03 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20032889A NO328707B1 (no) | 2000-12-22 | 2003-06-23 | Quinuklidin-karbamat-derivater samt medisinske sammensetninger omfattende slike |
Country Status (33)
Country | Link |
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US (3) | US7208501B2 (et) |
EP (1) | EP1345937B1 (et) |
JP (1) | JP4445704B2 (et) |
KR (1) | KR100869722B1 (et) |
CN (1) | CN1298717C (et) |
AR (1) | AR035410A1 (et) |
AT (1) | ATE305468T1 (et) |
AU (1) | AU2002228015B2 (et) |
BG (1) | BG107930A (et) |
BR (1) | BR0116450A (et) |
CA (1) | CA2441896A1 (et) |
CZ (1) | CZ301323B6 (et) |
DE (1) | DE60113719T2 (et) |
DK (1) | DK1345937T3 (et) |
EC (1) | ECSP034660A (et) |
EE (1) | EE200300295A (et) |
ES (1) | ES2248409T3 (et) |
HK (1) | HK1055120A1 (et) |
HU (1) | HUP0303529A3 (et) |
IL (1) | IL156499A0 (et) |
MX (1) | MXPA03005583A (et) |
MY (1) | MY136674A (et) |
NO (1) | NO328707B1 (et) |
NZ (1) | NZ526580A (et) |
PE (1) | PE20020719A1 (et) |
PL (1) | PL362989A1 (et) |
RU (1) | RU2296762C2 (et) |
SI (1) | SI1345937T1 (et) |
SK (1) | SK8002003A3 (et) |
UA (1) | UA76131C2 (et) |
UY (1) | UY27092A1 (et) |
WO (1) | WO2002051841A1 (et) |
ZA (1) | ZA200304769B (et) |
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