PT1811999E - Derivados de quinoclidina e sua utilizaçâo como antagonistas do receptor muscarínico m3 - Google Patents

Info

Publication number

PT1811999E

PT1811999E PT05798470T PT05798470T PT1811999E PT 1811999 E PT1811999 E PT 1811999E PT 05798470 T PT05798470 T PT 05798470T PT 05798470 T PT05798470 T PT 05798470T PT 1811999 E PT1811999 E PT 1811999E

Authority

PT

Portugal

Prior art keywords

bicyclo

azonia

hydroxy

octane

ylcarbamoylmethyl

Prior art date

2004-11-02

Links

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• 150000008584 quinuclidines Chemical class 0.000 title description 3
• 229940122694 Muscarinic M3 receptor antagonist Drugs 0.000 title description 2
• 239000003681 muscarinic M3 receptor antagonist Substances 0.000 title description 2
• -1 9H-fluoren-9-yl Chemical group 0.000 claims description 387
• 150000001875 compounds Chemical class 0.000 claims description 138
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 57
• 239000000203 mixture Substances 0.000 claims description 41
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
• 238000000034 method Methods 0.000 claims description 30
• 150000003839 salts Chemical class 0.000 claims description 30
• 238000011282 treatment Methods 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 239000001301 oxygen Chemical group 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
• 239000011593 sulfur Chemical group 0.000 claims description 12
• 229910052717 sulfur Chemical group 0.000 claims description 12
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
• 239000000126 substance Substances 0.000 claims description 11
• 150000002431 hydrogen Chemical class 0.000 claims description 10
• 230000000144 pharmacologic effect Effects 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 9
• 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 7
• 230000003110 anti-inflammatory effect Effects 0.000 claims description 7
• 230000002757 inflammatory effect Effects 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 208000027866 inflammatory disease Diseases 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
• 230000001387 anti-histamine Effects 0.000 claims description 5
• 239000000739 antihistaminic agent Substances 0.000 claims description 5
• 229940124630 bronchodilator Drugs 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 159000000000 sodium salts Chemical class 0.000 claims description 5
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 4
• BDDIUTHMWNWMRJ-UHFFFAOYSA-N octane;hydrobromide Chemical compound Br.CCCCCCCC BDDIUTHMWNWMRJ-UHFFFAOYSA-N 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
• 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 description 3
• 229940124584 antitussives Drugs 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 239000000850 decongestant Substances 0.000 claims description 3
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
• LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 claims description 2
• 102000007202 Muscarinic M3 Receptor Human genes 0.000 claims description 2
• 108010008405 Muscarinic M3 Receptor Proteins 0.000 claims description 2
• 208000027771 Obstructive airways disease Diseases 0.000 claims description 2
• GAZDVSXUYQWHSZ-QVOXVMGDSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(C1)C(=O)NC=1N=NC=CC=1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 GAZDVSXUYQWHSZ-QVOXVMGDSA-N 0.000 claims description 2
• WASPVIDRFWKIFH-PMLWWUNYSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-fluorene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3C4=CC=CC=C4C4=CC=CC=C43)[N+]21C(=O)NC1=CC=CN=N1 WASPVIDRFWKIFH-PMLWWUNYSA-N 0.000 claims description 2
• IINGMDFVUYFQHG-PMLWWUNYSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-xanthene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3C4=CC=CC=C4OC4=CC=CC=C43)[N+]21C(=O)NC1=CC=CN=N1 IINGMDFVUYFQHG-PMLWWUNYSA-N 0.000 claims description 2
• PZQITBZKKUYABR-VWNNWTLOSA-O [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate Chemical compound O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1OC=CC=1)(O)C1CCCC1 PZQITBZKKUYABR-VWNNWTLOSA-O 0.000 claims description 2
• XAPIRXONNQLWIT-CJYZSSDISA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-fluorene-9-carboxylate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2C3=CC=CC=C3C3=CC=CC=C32)=N1 XAPIRXONNQLWIT-CJYZSSDISA-N 0.000 claims description 2
• PYZGCNACJWBRHV-OQLFIWBKSA-O [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-3-yl)-2-hydroxyacetate Chemical compound O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CN=2)C1)C(=O)C(C1=COC=C1)(O)C1CCCC1 PYZGCNACJWBRHV-OQLFIWBKSA-O 0.000 claims description 2
• 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 description 2
• WUJYVHUCCLKWKW-SGFHCSRJSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-fluorene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4C4=CC=CC=C43)CC[N+]12CC(=O)NC1=CN=CC=N1 WUJYVHUCCLKWKW-SGFHCSRJSA-N 0.000 claims description 2
• SZUGBQXPVVBDJC-CJYZSSDISA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-fluorene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4C4=CC=CC=C43)CC[N+]12CC(=O)NC1=CN=CN=C1 SZUGBQXPVVBDJC-CJYZSSDISA-N 0.000 claims description 2
• 125000001246 bromo group Chemical group Br* 0.000 claims description 2
• 229960003728 ciclesonide Drugs 0.000 claims description 2
• WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 claims description 2
• 229960000289 fluticasone propionate Drugs 0.000 claims description 2
• 125000002346 iodo group Chemical group I* 0.000 claims description 2
• 230000001404 mediated effect Effects 0.000 claims description 2
• WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 claims description 2
• 229960002744 mometasone furoate Drugs 0.000 claims description 2
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
• 229940121786 Beta 2 adrenoreceptor agonist Drugs 0.000 claims 2
• 239000003862 glucocorticoid Substances 0.000 claims 2
• 206010027654 Allergic conditions Diseases 0.000 claims 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
• MWDBLAXQQMGHGP-UZJJCEHNSA-O [(2r)-2-methyl-1-[(5-methyl-1,2-oxazol-3-yl)carbamoyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-diphenylacetate Chemical compound C1([C@H]([N+]2(CCC1CC2)C(=O)NC1=NOC(C)=C1)C)OC(=O)C(O)(C=1C=CC=CC=1)C1=CC=CC=C1 MWDBLAXQQMGHGP-UZJJCEHNSA-O 0.000 claims 1
• XJQRRXDTQMFSPX-POXKQJJMSA-O [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclohexyl-2-hydroxy-2-phenylacetate Chemical compound C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=CC=CC=2)CCCCC1 XJQRRXDTQMFSPX-POXKQJJMSA-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
• QURMEKJIUAZANR-FVRMQZBVSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclobutyl-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)C1CCC1 QURMEKJIUAZANR-FVRMQZBVSA-N 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
• 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
• KNRAZWQROOQZCD-HIPLPVRDSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-(2-methoxyphenyl)-2-phenylacetate;bromide Chemical compound [Br-].COC1=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 KNRAZWQROOQZCD-HIPLPVRDSA-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
• VTBLMPHPICFVKP-FIQQBEOASA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-phenyl-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C=3C=CC=CC=3)[N+]21CC(=O)NC=1C=CON=1 VTBLMPHPICFVKP-FIQQBEOASA-N 0.000 claims 1
• DAKBDLXZFNNQTD-RTDUGLMJSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9,10-dihydroanthracene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4CC4=CC=CC=C43)CC[N+]12CC(=O)NC=1C=CON=1 DAKBDLXZFNNQTD-RTDUGLMJSA-N 0.000 claims 1
• VLRPFSHYKSDKKG-CUZWAUKLSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopropyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CC2)C=2SC=CC=2)=N1 VLRPFSHYKSDKKG-CUZWAUKLSA-N 0.000 claims 1
• QVPAEXCVBGXRLP-DXLVBJHUSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-di(thiophen-3-yl)acetate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2=CSC=C2)C2=CSC=C2)=N1 QVPAEXCVBGXRLP-DXLVBJHUSA-N 0.000 claims 1
• RCVVTPNGORUHNV-OANMHNKXSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-phenyl-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2=CSC=C2)C=2C=CC=CC=2)=N1 RCVVTPNGORUHNV-OANMHNKXSA-N 0.000 claims 1
• JNSNUESJPBPJFB-XCEOWTAJSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9,10-dihydroanthracene-9-carboxylate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2C3=CC=CC=C3CC3=CC=CC=C32)=N1 JNSNUESJPBPJFB-XCEOWTAJSA-N 0.000 claims 1
• JOMHYNAWONELCA-SUSCGCCGSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-(furan-3-yl)-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2=COC=C2)C=2C=CC=CC=2)=N1 JOMHYNAWONELCA-SUSCGCCGSA-N 0.000 claims 1
• RJKIEYOHIQSNMU-UTEXUTGQSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclobutyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CCC2)C=2SC=CC=2)=N1 RJKIEYOHIQSNMU-UTEXUTGQSA-N 0.000 claims 1
• WIQJVHQRIJIIIT-NSLDKZMESA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CCCC2)C=2OC=CC=2)=N1 WIQJVHQRIJIIIT-NSLDKZMESA-N 0.000 claims 1
• RLIHYEQLMBPUPE-FVRMQZBVSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopropyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CC2)C=2SC=CC=2)=N1 RLIHYEQLMBPUPE-FVRMQZBVSA-N 0.000 claims 1
• BAJKRLDRJMTAPQ-PKLCTQDOSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9,10-dihydroanthracene-9-carboxylate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2C3=CC=CC=C3CC3=CC=CC=C32)=N1 BAJKRLDRJMTAPQ-PKLCTQDOSA-N 0.000 claims 1
• OBLKUAOGTWYWDH-NOWPHXOYSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-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)NC=2N=CN=CN=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCCC1 OBLKUAOGTWYWDH-NOWPHXOYSA-N 0.000 claims 1
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