CA2723981A1 - New compounds 273 - Google Patents

Info

Publication number

CA2723981A1

CA2723981A1 CA2723981A CA2723981A CA2723981A1 CA 2723981 A1 CA2723981 A1 CA 2723981A1 CA 2723981 A CA2723981 A CA 2723981A CA 2723981 A CA2723981 A CA 2723981A CA 2723981 A1 CA2723981 A1 CA 2723981A1

Authority

CA

Canada

Prior art keywords

bicyclo

phenyl

cycloheptanecarbonyloxy

azonia

octane

Prior art date

2008-05-13

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 244
• 238000011282 treatment Methods 0.000 claims abstract description 20
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 238000004519 manufacturing process Methods 0.000 claims abstract description 10
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 9
• 238000000034 method Methods 0.000 claims description 42
• 239000003112 inhibitor Substances 0.000 claims description 35
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 13
• 239000004480 active ingredient Substances 0.000 claims description 12
• 229940127557 pharmaceutical product Drugs 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 11
• 241001465754 Metazoa Species 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 10
• 150000001450 anions Chemical class 0.000 claims description 10
• JFUAWXPBHXKZGA-IBGZPJMESA-N 4-fluoro-2-[(4r)-5,5,5-trifluoro-4-hydroxy-2-methyl-4-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-yl]phenol Chemical compound C([C@@](O)(CC=1NC2=CN=CC=C2C=1)C(F)(F)F)C(C)(C)C1=CC(F)=CC=C1O JFUAWXPBHXKZGA-IBGZPJMESA-N 0.000 claims description 6
• 229940124750 glucocorticoid receptor agonist Drugs 0.000 claims description 6
• 230000003637 steroidlike Effects 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 5
• 108091000080 Phosphotransferase Proteins 0.000 claims description 5
• 239000002671 adjuvant Substances 0.000 claims description 5
• 239000000048 adrenergic agonist Substances 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 102000020233 phosphotransferase Human genes 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 102000009410 Chemokine receptor Human genes 0.000 claims description 4
• 108050000299 Chemokine receptor Proteins 0.000 claims description 4
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 4
• 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 4
• 229940099471 Phosphodiesterase inhibitor Drugs 0.000 claims description 3
• 239000002571 phosphodiesterase inhibitor Substances 0.000 claims description 3
• WVDUSDHWEXNGTR-PNDBIIQMSA-O [(3r)-1-(2-anilino-2-oxoethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CC(=O)NC=1C=CC=CC=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 WVDUSDHWEXNGTR-PNDBIIQMSA-O 0.000 claims description 2
• WOZYWLXIGDFAPW-DZHMJCDGSA-N [(3r)-1-(2-pyrazin-2-ylethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)[N+]21CCC1=CN=CC=N1 WOZYWLXIGDFAPW-DZHMJCDGSA-N 0.000 claims description 2
• MDNJCXFVPOUYNC-SHCORVSCSA-N [(3r)-1-(2-pyridin-3-yloxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)[N+]21CCOC1=CC=CN=C1 MDNJCXFVPOUYNC-SHCORVSCSA-N 0.000 claims description 2
• HEOCROWSMBACAP-XCCMJPSHSA-N [(3r)-1-(3-pyridin-4-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)[N+]21CCCC1=CC=NC=C1 HEOCROWSMBACAP-XCCMJPSHSA-N 0.000 claims description 2
• VDFJURJEIWWHOJ-MOOYVADDSA-O [(3r)-1-[2-(1,2-benzoxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CC(=O)NC=1C2=CC=CC=C2ON=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 VDFJURJEIWWHOJ-MOOYVADDSA-O 0.000 claims description 2
• WTICJOFLWLLTMR-ZITBFLLYSA-O [(3r)-1-[2-(1,2-benzoxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-thiophen-2-ylcycloheptane-1-carboxylate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CC(=O)NC=1C2=CC=CC=C2ON=1)C(=O)C1(C=2SC=CC=2)CCCCCC1 WTICJOFLWLLTMR-ZITBFLLYSA-O 0.000 claims description 2
• JKWGPZJKRRPSHL-JLMMNGPTSA-O [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-(3-fluorophenyl)cycloheptane-1-carboxylate Chemical compound FC1=CC=CC(C2(CCCCCC2)C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)=C1 JKWGPZJKRRPSHL-JLMMNGPTSA-O 0.000 claims description 2
• YEVKJUHVUKDBGV-HZCURFCSSA-O [(3r)-1-[2-(1,3-oxazol-2-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CC(=O)NC=1OC=CN=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 YEVKJUHVUKDBGV-HZCURFCSSA-O 0.000 claims description 2
• RMBASTRUSAROFV-LROTXVJESA-O [(3r)-1-[2-(2,3-difluoroanilino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound FC1=CC=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2C=CC=CC=2)=C1F RMBASTRUSAROFV-LROTXVJESA-O 0.000 claims description 2
• PRWDFXUFMHHGQH-KCTUUFLGSA-N [(3r)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound O([C@@H]1C2CC[N+](CC2)(CCC=2C=C3CCOC3=CC=2)C1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 PRWDFXUFMHHGQH-KCTUUFLGSA-N 0.000 claims description 2
• DQOICSUTFYLKAU-LROTXVJESA-O [(3r)-1-[2-(2,6-difluoroanilino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound FC1=CC=CC(F)=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 DQOICSUTFYLKAU-LROTXVJESA-O 0.000 claims description 2
• JFYBBPHHBZBHTO-QUBVCFFMSA-O [(3r)-1-[2-(2-fluoroanilino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound FC1=CC=CC=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 JFYBBPHHBZBHTO-QUBVCFFMSA-O 0.000 claims description 2
• JQMACVFBFUCENQ-KRXIBUGQSA-O [(3r)-1-[2-(2-methylanilino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound CC1=CC=CC=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 JQMACVFBFUCENQ-KRXIBUGQSA-O 0.000 claims description 2
• WTHBMTUJGYRMGR-HAMJSAHASA-N [(3r)-1-[2-(2-phenylethoxy)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)[N+]21CCOCCC1=CC=CC=C1 WTHBMTUJGYRMGR-HAMJSAHASA-N 0.000 claims description 2
• FCJDGRAUBKEYFV-HEOVBLLFSA-O [(3r)-1-[2-(3,5-difluoroanilino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound FC1=CC(F)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2C=CC=CC=2)=C1 FCJDGRAUBKEYFV-HEOVBLLFSA-O 0.000 claims description 2
• GKCYEIZOVBMXSO-NGKDMHNESA-O [(3r)-1-[2-(3-fluoroanilino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-thiophen-2-ylcycloheptane-1-carboxylate Chemical compound FC1=CC=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2SC=CC=2)=C1 GKCYEIZOVBMXSO-NGKDMHNESA-O 0.000 claims description 2
• RRFWSIRHJZZHKW-KRXIBUGQSA-O [(3r)-1-[2-(3-methylanilino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound CC1=CC=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2C=CC=CC=2)=C1 RRFWSIRHJZZHKW-KRXIBUGQSA-O 0.000 claims description 2
• JRPHMSGYARGWKS-NXYCWYFDSA-N [(3r)-1-[2-(4-fluorophenoxy)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound C1=CC(F)=CC=C1OCC[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 JRPHMSGYARGWKS-NXYCWYFDSA-N 0.000 claims description 2
• HWWZLRTUULTFKE-KRXIBUGQSA-N [(3r)-1-[2-(n-methylanilino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CC(=O)N(C)C=1C=CC=CC=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 HWWZLRTUULTFKE-KRXIBUGQSA-N 0.000 claims description 2
• FGEWJFRJCFLWHL-LAAOYOPBSA-O [(3r)-1-[2-(pyrazine-2-carbonylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CCNC(=O)C=1N=CC=NC=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 FGEWJFRJCFLWHL-LAAOYOPBSA-O 0.000 claims description 2
• VHTIGXNEAZTOFX-IYKJVDJMSA-O [(3r)-1-[2-[(2-methylpyridin-4-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound C1=NC(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2C=CC=CC=2)=C1 VHTIGXNEAZTOFX-IYKJVDJMSA-O 0.000 claims description 2
• IBJUZBUANZMFGF-PHMQNLDASA-O [(3r)-1-[2-[(2-methylpyrimidin-4-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound CC1=NC=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2C=CC=CC=2)=N1 IBJUZBUANZMFGF-PHMQNLDASA-O 0.000 claims description 2
• PFKYJISOTBSPED-FZCUKYEHSA-O [(3r)-1-[2-[(3-fluoropyridin-2-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound FC1=CC=CN=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 PFKYJISOTBSPED-FZCUKYEHSA-O 0.000 claims description 2
• DLBADXNZWOPANT-JFBYPVLBSA-O [(3r)-1-[2-[(3-fluoropyridin-4-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound FC1=CN=CC=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 DLBADXNZWOPANT-JFBYPVLBSA-O 0.000 claims description 2
• VHOZZSJBOFMOLB-VPPXUNETSA-O [(3r)-1-[2-[(3-methyl-1,2-oxazol-5-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-thiophen-2-ylcycloheptane-1-carboxylate Chemical compound O1N=C(C)C=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3SC=CC=3)CCC2CC1 VHOZZSJBOFMOLB-VPPXUNETSA-O 0.000 claims description 2
• XGHARZDCTSHGIG-HWGCPHSESA-N [(3r)-1-[2-[(4-cyanophenyl)methoxy]ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)[N+]21CCOCC1=CC=C(C#N)C=C1 XGHARZDCTSHGIG-HWGCPHSESA-N 0.000 claims description 2
• YHFMDYSRCQTRRJ-IIIFQBMYSA-N [(3r)-1-[2-[(4-methoxyphenyl)methoxy]ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound C1=CC(OC)=CC=C1COCC[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 YHFMDYSRCQTRRJ-IIIFQBMYSA-N 0.000 claims description 2
• IDYAWESBBMGGQX-JWALKRTLSA-O [(3r)-1-[2-[(4-methylpyridin-2-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound CC1=CC=NC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2C=CC=CC=2)=C1 IDYAWESBBMGGQX-JWALKRTLSA-O 0.000 claims description 2
• ATAASUQPYWKXQB-FZCUKYEHSA-O [(3r)-1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound N1=CC(Cl)=CC=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 ATAASUQPYWKXQB-FZCUKYEHSA-O 0.000 claims description 2
• DQCMINAFBHBOOI-FZCUKYEHSA-O [(3r)-1-[2-[(5-fluoropyridin-2-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound N1=CC(F)=CC=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 DQCMINAFBHBOOI-FZCUKYEHSA-O 0.000 claims description 2
• PRVQJAXHLAUQDK-JFBYPVLBSA-O [(3r)-1-[2-[(5-fluoropyridin-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound FC1=CN=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2C=CC=CC=2)=C1 PRVQJAXHLAUQDK-JFBYPVLBSA-O 0.000 claims description 2
• XIQZOOAAJRKKQK-VPPXUNETSA-O [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-thiophen-2-ylcycloheptane-1-carboxylate Chemical compound O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2SC=CC=2)=N1 XIQZOOAAJRKKQK-VPPXUNETSA-O 0.000 claims description 2
• GYYVQYKLYDWBOE-VORDGODZSA-O [(3r)-1-[2-[(5-methylpyrazin-2-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-thiophen-2-ylcycloheptane-1-carboxylate Chemical compound C1=NC(C)=CN=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3SC=CC=3)CCC2CC1 GYYVQYKLYDWBOE-VORDGODZSA-O 0.000 claims description 2
• GWROMZWCYWAJKT-JWALKRTLSA-O [(3r)-1-[2-[(5-methylpyridin-2-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound N1=CC(C)=CC=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 GWROMZWCYWAJKT-JWALKRTLSA-O 0.000 claims description 2
• VAPAJITXNSYUPR-PHMQNLDASA-O [(3r)-1-[2-[(6-methylpyrazin-2-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound CC1=CN=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2C=CC=CC=2)=N1 VAPAJITXNSYUPR-PHMQNLDASA-O 0.000 claims description 2
• YQHIMPAZABTRKR-PHMQNLDASA-O [(3r)-1-[2-[(6-methylpyridazin-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound N1=NC(C)=CC=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 YQHIMPAZABTRKR-PHMQNLDASA-O 0.000 claims description 2
• QKMCGNICAGLTDQ-JWALKRTLSA-O [(3r)-1-[2-[(6-methylpyridin-2-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound CC1=CC=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2C=CC=CC=2)=N1 QKMCGNICAGLTDQ-JWALKRTLSA-O 0.000 claims description 2
• DGYXUBXPMBVTPU-IYKJVDJMSA-O [(3r)-1-[2-[(6-methylpyridin-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound C1=NC(C)=CC=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 DGYXUBXPMBVTPU-IYKJVDJMSA-O 0.000 claims description 2
• DMJWMLJZIIQIDG-PHMQNLDASA-O [(3r)-1-[2-[(6-methylpyrimidin-4-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound C1=NC(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2C=CC=CC=2)=N1 DMJWMLJZIIQIDG-PHMQNLDASA-O 0.000 claims description 2
• VFFKUSRXBZIIKA-VONVOUFKSA-O [(3r)-1-[2-oxo-2-(1,2,4-thiadiazol-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CC(=O)NC=1SN=CN=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 VFFKUSRXBZIIKA-VONVOUFKSA-O 0.000 claims description 2
• DSOSUTCGTSBHKJ-QJYFYXOJSA-O [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-(3-fluorophenyl)cycloheptane-1-carboxylate Chemical compound FC1=CC=CC(C2(CCCCCC2)C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC=3N=CC=NC=3)C2)=C1 DSOSUTCGTSBHKJ-QJYFYXOJSA-O 0.000 claims description 2
• CHZZDBQXEWINOU-RWOUKYTFSA-O [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-thiophen-2-ylcycloheptane-1-carboxylate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CC(=O)NC=1N=CC=NC=1)C(=O)C1(C=2SC=CC=2)CCCCCC1 CHZZDBQXEWINOU-RWOUKYTFSA-O 0.000 claims description 2
• CSVMTCVVMOSIJL-RWOUKYTFSA-O [(3r)-1-[2-oxo-2-(pyridazin-3-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-thiophen-2-ylcycloheptane-1-carboxylate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CC(=O)NC=1N=NC=CC=1)C(=O)C1(C=2SC=CC=2)CCCCCC1 CSVMTCVVMOSIJL-RWOUKYTFSA-O 0.000 claims description 2
• LGIDQLGPVNXMJW-UYXPAWESSA-O [(3r)-1-[2-oxo-2-(pyridazin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)CC(=O)NC=1C=NN=CC=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 LGIDQLGPVNXMJW-UYXPAWESSA-O 0.000 claims description 2
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