CA2490082A1 - Quinuclidine derivatives and pharmaceutical compositions containing the same - Google Patents

Info

Publication number

CA2490082A1

CA2490082A1 CA002490082A CA2490082A CA2490082A1 CA 2490082 A1 CA2490082 A1 CA 2490082A1 CA 002490082 A CA002490082 A CA 002490082A CA 2490082 A CA2490082 A CA 2490082A CA 2490082 A1 CA2490082 A1 CA 2490082A1

Authority

CA

Canada

Prior art keywords

ylmethyl

azoniabicyclo

octane

compound

optionally substituted

Prior art date

2002-06-21

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

• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 15
• 150000008584 quinuclidines Chemical class 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 209
• 150000003839 salts Chemical class 0.000 claims abstract description 11
• 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims abstract description 9
• 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims abstract description 9
• 239000005557 antagonist Substances 0.000 claims abstract description 7
• 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 289
• -1 furan-2-ylmethyl Chemical group 0.000 claims description 171
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical group [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 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 40
• 125000000217 alkyl group Chemical group 0.000 claims description 32
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
• 125000004122 cyclic group Chemical group 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 28
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
• 239000002253 acid Substances 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 208000023504 respiratory system disease Diseases 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 150000002367 halogens Chemical class 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 208000018522 Gastrointestinal disease Diseases 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 11
• 208000014001 urinary system disease Diseases 0.000 claims description 11
• 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 10
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 239000000460 chlorine Substances 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 239000011737 fluorine Substances 0.000 claims description 10
• 230000000241 respiratory effect Effects 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 10
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 150000001450 anions Chemical class 0.000 claims description 8
• 208000010643 digestive system disease Diseases 0.000 claims description 8
• 208000018685 gastrointestinal system disease Diseases 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 7
• 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 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 6
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 208000035475 disorder Diseases 0.000 claims description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 5
• 208000012931 Urologic disease Diseases 0.000 claims description 5
• 239000000556 agonist Substances 0.000 claims description 5
• 230000008485 antagonism Effects 0.000 claims description 5
• 239000000043 antiallergic agent Substances 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 5
• 150000003431 steroids Chemical class 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• QNJLKXCSRKQDKU-JQXPCOHGSA-M [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-(3-methylphenyl)-n-[(2,4,5-trifluorophenyl)methyl]carbamate;bromide Chemical compound [Br-].CC1=CC=CC(N(CC=2C(=CC(F)=C(F)C=2)F)C(=O)O[C@@H]2C3CC[N+](CC3)(CCOC=3C=CC=CC=3)C2)=C1 QNJLKXCSRKQDKU-JQXPCOHGSA-M 0.000 claims description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims description 4
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 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
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 239000013066 combination product Substances 0.000 claims description 3
• 229940127555 combination product Drugs 0.000 claims description 3
• 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 description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 229910052740 iodine Inorganic materials 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• TVSLNRQODQRVJZ-UHFFFAOYSA-N 2-(3,4,5-trifluorophenyl)acetonitrile Chemical group FC1=CC(CC#N)=CC(F)=C1F TVSLNRQODQRVJZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 2
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
• ODFAODFYHWXZBL-FTBISJDPSA-N C1=CSC(CN(CCC=2C=CC(F)=CC=2)C(O)=O)=C1C.FC1=CC(OC)=CC=C1CN(C(=O)O[C@@H]1C2CCN(CC2)C1)CC1=C(C)OC(C)=C1 Chemical compound C1=CSC(CN(CCC=2C=CC(F)=CC=2)C(O)=O)=C1C.FC1=CC(OC)=CC=C1CN(C(=O)O[C@@H]1C2CCN(CC2)C1)CC1=C(C)OC(C)=C1 ODFAODFYHWXZBL-FTBISJDPSA-N 0.000 claims description 2
• XGVQBSWEQBCRQW-LMOVPXPDSA-N FC1=CC(=C(C=C1)N(C(O)=O)CC=1SC=CC1C)C.N12C[C@@H](C(CC1)CC2)OC(N(C2=C(C=C(C(=C2)F)F)F)CC=2SC(=CC2)Br)=O Chemical compound FC1=CC(=C(C=C1)N(C(O)=O)CC=1SC=CC1C)C.N12C[C@@H](C(CC1)CC2)OC(N(C2=C(C=C(C(=C2)F)F)F)CC=2SC(=CC2)Br)=O XGVQBSWEQBCRQW-LMOVPXPDSA-N 0.000 claims description 2
• HHFGZGKXBXBZBZ-BDQAORGHSA-N O1C(C)=CC(CN(CC2=COC=C2)C(O)=O)=C1C(F)(F)F.O1C(C)=CC=C1CN(C(=O)O[C@@H]1C2CCN(CC2)C1)CC1=CC(C)=C(C)O1 Chemical compound O1C(C)=CC(CN(CC2=COC=C2)C(O)=O)=C1C(F)(F)F.O1C(C)=CC=C1CN(C(=O)O[C@@H]1C2CCN(CC2)C1)CC1=CC(C)=C(C)O1 HHFGZGKXBXBZBZ-BDQAORGHSA-N 0.000 claims description 2
• QKWOYWROMVNAEX-QKIIOBKNSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-(3-methylphenyl)-n-[(2,4,5-trifluorophenyl)methyl]carbamate;bromide Chemical compound [Br-].CC1=CC=CC(N(CC=2C(=CC(F)=C(F)C=2)F)C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3C=CC=CC=3)C2)=C1 QKWOYWROMVNAEX-QKIIOBKNSA-M 0.000 claims description 2
• CLOSPRMVOVWGOW-SFHVURJKSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-[(4-bromo-5-methylthiophen-2-yl)methyl]-n-[(3-methylthiophen-2-yl)methyl]carbamate Chemical compound C1=CSC(CN(CC=2SC(C)=C(Br)C=2)C(=O)O[C@@H]2C3CCN(CC3)C2)=C1C CLOSPRMVOVWGOW-SFHVURJKSA-N 0.000 claims description 2
• DXNQLZJOTVNBOZ-UHFFFAOYSA-N [O]C(=O)Nc1ccccc1 Chemical group [O]C(=O)Nc1ccccc1 DXNQLZJOTVNBOZ-UHFFFAOYSA-N 0.000 claims description 2
• 150000001805 chlorine compounds Chemical group 0.000 claims description 2
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
• 239000011630 iodine Substances 0.000 claims description 2
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 2
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
• 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
• 230000001575 pathological effect Effects 0.000 claims 5
• CRDNCFIFWUFJEI-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n,n-diphenylcarbamate;1-azabicyclo[2.2.2]octan-3-yl n-ethyl-n-phenylcarbamate Chemical compound C1N(CC2)CCC2C1OC(=O)N(CC)C1=CC=CC=C1.C1N(CC2)CCC2C1OC(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 CRDNCFIFWUFJEI-UHFFFAOYSA-N 0.000 claims 1
• PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical class C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims 1
• JARYHXHZIFTPKI-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)ethyl-[(5-methylfuran-2-yl)methyl]carbamic acid Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C(O)=O)CC1=CC=C(C)O1 JARYHXHZIFTPKI-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• LMHGDAVQSRGVLZ-OPSAGGCXSA-L CCOC(=O)CCCC[N+]12CCC(CC1)[C@H](C2)OC(=O)N(CCC3=CC(=C(C=C3)OC)OC)CC4=CC=C(O4)C.CCOC(=O)CCCC[N+]12CCC(CC1)[C@H](C2)OC(=O)N(CCC3=CC(=C(C=C3)OC)OC)CC4=CC=C(O4)C.C(=O)(C(F)(F)F)[O-].C(=O)(C(F)(F)F)[O-] Chemical compound CCOC(=O)CCCC[N+]12CCC(CC1)[C@H](C2)OC(=O)N(CCC3=CC(=C(C=C3)OC)OC)CC4=CC=C(O4)C.CCOC(=O)CCCC[N+]12CCC(CC1)[C@H](C2)OC(=O)N(CCC3=CC(=C(C=C3)OC)OC)CC4=CC=C(O4)C.C(=O)(C(F)(F)F)[O-].C(=O)(C(F)(F)F)[O-] LMHGDAVQSRGVLZ-OPSAGGCXSA-L 0.000 claims 1
• SXBLOXRYPVLVLR-KXSSUAHJSA-N N12C[C@@H](C(CC1)CC2)OC(N(CC2=C(C=C(C(=C2)F)F)F)CC2=CSC=C2)=O.N21C[C@@H](C(CC2)CC1)OC(N(CC1=CSC=C1)C1=CC(=C(C=C1)OC)F)=O Chemical compound N12C[C@@H](C(CC1)CC2)OC(N(CC2=C(C=C(C(=C2)F)F)F)CC2=CSC=C2)=O.N21C[C@@H](C(CC2)CC1)OC(N(CC1=CSC=C1)C1=CC(=C(C=C1)OC)F)=O SXBLOXRYPVLVLR-KXSSUAHJSA-N 0.000 claims 1
• KAEPUDLIBVYOEJ-XAEROCQYSA-M [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-(4-fluoro-2-methylphenyl)-n-[(3-methylthiophen-2-yl)methyl]carbamate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CSC(CN(C(=O)O[C@@H]2C3CC[N+](CC3)(CCOC=3C=CC=CC=3)C2)C=2C(=CC(F)=CC=2)C)=C1C KAEPUDLIBVYOEJ-XAEROCQYSA-M 0.000 claims 1
• ZETQILUTJDIRCU-GLSBDXMNSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-[(4-bromo-5-methylthiophen-2-yl)methyl]-n-[(3-methylthiophen-2-yl)methyl]carbamate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CSC(CN(CC=2SC(C)=C(Br)C=2)C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3C=CC=CC=3)C2)=C1C ZETQILUTJDIRCU-GLSBDXMNSA-M 0.000 claims 1
• WIFYAJXTBJHEAS-NSTLWARWSA-N [(3r)-1-[3-(3-hydroxyphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-[(4,5-dimethylfuran-2-yl)methyl]-n-[(5-methylfuran-2-yl)methyl]carbamate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.O1C(C)=CC=C1CN(C(=O)O[C@@H]1C2CC[N+](CC2)(CCCOC=2C=C(O)C=CC=2)C1)CC1=CC(C)=C(C)O1 WIFYAJXTBJHEAS-NSTLWARWSA-N 0.000 claims 1
• KAJQEDYZTVPRPW-WGLRCJLISA-M [(3r)-1-[3-(4-fluorophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-(furan-3-ylmethyl)-n-[[5-methyl-2-(trifluoromethyl)furan-3-yl]methyl]carbamate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.O1C(C)=CC(CN(CC2=COC=C2)C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=CC(F)=CC=3)C2)=C1C(F)(F)F KAJQEDYZTVPRPW-WGLRCJLISA-M 0.000 claims 1
• RDXICHROOMAYQC-SFYJNAPPSA-M [(3r)-1-methyl-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate;iodide Chemical compound [I-].O([C@@H]1C2CC[N+](CC2)(C1)C)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 RDXICHROOMAYQC-SFYJNAPPSA-M 0.000 claims 1
• 238000002360 preparation method Methods 0.000 abstract description 41
• 230000008569 process Effects 0.000 abstract description 7
• 238000002560 therapeutic procedure Methods 0.000 abstract description 3
• 150000004657 carbamic acid derivatives Chemical class 0.000 abstract description 2
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 106
• 238000005481 NMR spectroscopy Methods 0.000 description 98
• 238000005160 1H NMR spectroscopy Methods 0.000 description 39
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
• 239000000243 solution Substances 0.000 description 29
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• 239000003921 oil Substances 0.000 description 22
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
• 239000000047 product Substances 0.000 description 21
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 239000000725 suspension Substances 0.000 description 14
• 238000006243 chemical reaction Methods 0.000 description 13
• 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 description 12
• 238000003756 stirring Methods 0.000 description 12
• 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 11
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
• 229910052708 sodium Inorganic materials 0.000 description 11
• 239000007787 solid Substances 0.000 description 10
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• FEAAEXOAAKGNBO-JOMKWTIYSA-N [(3r)-1-(2-phenoxyethyl)-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+]21CCOC1=CC=CC=C1 FEAAEXOAAKGNBO-JOMKWTIYSA-N 0.000 description 1
• NJCVUBFVVNHWHH-IIIFQBMYSA-N [(3r)-1-(2-phenoxyethyl)-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+]21CCOC1=CC=CC=C1 NJCVUBFVVNHWHH-IIIFQBMYSA-N 0.000 description 1
• 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 description 1
• 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 description 1
• VPQPEPPKQPUSKQ-KGBLJUBMSA-N [(3r)-1-(2-phenylmethoxyethyl)-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+]21CCOCC1=CC=CC=C1 VPQPEPPKQPUSKQ-KGBLJUBMSA-N 0.000 description 1
• QPOYDCASJDUGLJ-FUFAFYGISA-N [(3r)-1-(2-phenylmethoxyethyl)-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+]21CCOCC1=CC=CC=C1 QPOYDCASJDUGLJ-FUFAFYGISA-N 0.000 description 1
• SYRVXBDLMMPFEM-ROTRRZJSSA-N [(3r)-1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-phenyl-n-(thiophen-2-ylmethyl)carbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CC=3SC=CC=3)C=3C=CC=CC=3)[N+]21CCOCC1=CC=CC=C1 SYRVXBDLMMPFEM-ROTRRZJSSA-N 0.000 description 1
• QXBQBQGAGIWXEC-KGBLJUBMSA-N [(3r)-1-(2-phenylmethoxyethyl)-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+]21CCOCC1=CC=CC=C1 QXBQBQGAGIWXEC-KGBLJUBMSA-N 0.000 description 1
• PZTHGNBCWQXWTQ-IYUIPRCHSA-N [(3r)-1-(3-cyanopropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(CCCC#N)C1)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 PZTHGNBCWQXWTQ-IYUIPRCHSA-N 0.000 description 1
• HGKJUCQDXWXVOK-XWGIXXMPSA-N [(3r)-1-(3-cyanopropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(CCCC#N)C1)C(=O)N(CCCC)C1=CC=CC=C1 HGKJUCQDXWXVOK-XWGIXXMPSA-N 0.000 description 1
• NATRMGUMFWTHML-WWAKMMQFSA-N [(3r)-1-(3-hydroxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-butyl-n-phenylcarbamate Chemical compound O([C@@H]1C2CC[N+](CC2)(CCCO)C1)C(=O)N(CCCC)C1=CC=CC=C1 NATRMGUMFWTHML-WWAKMMQFSA-N 0.000 description 1
• HQLQUEMRGIWKLH-ROTRRZJSSA-N [(3r)-1-(3-phenoxypropyl)-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=C1 HQLQUEMRGIWKLH-ROTRRZJSSA-N 0.000 description 1
• VJIRAXKGKHTNIX-JOMKWTIYSA-N [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n,n-bis(thiophen-2-ylmethyl)carbamate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)N(CC=3SC=CC=3)CC=3SC=CC=3)[N+]21CCCC1=CC=CC=C1 VJIRAXKGKHTNIX-JOMKWTIYSA-N 0.000 description 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 description 1
• IJROGYSFHCIWAC-PVQGFKEISA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-(3-fluorophenyl)-n-[(3,4,5-trifluorophenyl)methyl]carbamate;bromide Chemical compound [Br-].FC1=CC=CC(N(CC=2C=C(F)C(F)=C(F)C=2)C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3C=CC=CC=3)C2)=C1 IJROGYSFHCIWAC-PVQGFKEISA-M 0.000 description 1
• VDSSSYAPDUAPAR-ACIYGYOISA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-(cyclohexylmethyl)-n-(2-fluorophenyl)carbamate;bromide Chemical compound [Br-].FC1=CC=CC=C1N(C(=O)O[C@@H]1C2CC[N+](CC2)(CCCC=2C=CC=CC=2)C1)CC1CCCCC1 VDSSSYAPDUAPAR-ACIYGYOISA-M 0.000 description 1
• WAWYUYIDNWSAPS-PNYZXNCNSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-[(5-ethylthiophen-2-yl)methyl]-n-[(3-methylthiophen-2-yl)methyl]carbamate;bromide Chemical compound [Br-].S1C(CC)=CC=C1CN(C(=O)O[C@@H]1C2CC[N+](CC2)(CCCC=2C=CC=CC=2)C1)CC1=C(C)C=CS1 WAWYUYIDNWSAPS-PNYZXNCNSA-M 0.000 description 1
• QUQTWSOKVZEVEI-FUFAFYGISA-N [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-benzyl-n-(4-methylphenyl)carbamate Chemical compound C1=CC(C)=CC=C1N(C(=O)O[C@@H]1C2CC[N+](CC2)(CCCC=2C=CC=CC=2)C1)CC1=CC=CC=C1 QUQTWSOKVZEVEI-FUFAFYGISA-N 0.000 description 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 description 1
• 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 description 1
• NGQNIEGSHBVLIB-FUFAFYGISA-N [(3r)-1-(3-phenylpropyl)-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=CC=C1 NGQNIEGSHBVLIB-FUFAFYGISA-N 0.000 description 1
• 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
• 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 description 1
• JNJKTGYSCZXDCF-ROTRRZJSSA-N [(3r)-1-(3-thiophen-2-ylpropyl)-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+]21CCCC1=CC=CS1 JNJKTGYSCZXDCF-ROTRRZJSSA-N 0.000 description 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 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
• 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 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
• 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
• 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
• 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
• 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
• 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
• 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 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
• 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
• 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
• IIQLXEAKGBYKCI-IBGZPJMESA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-(3-fluoro-4-methoxyphenyl)-n-(thiophen-3-ylmethyl)carbamate Chemical compound C1=C(F)C(OC)=CC=C1N(C(=O)O[C@@H]1C2CCN(CC2)C1)CC1=CSC=C1 IIQLXEAKGBYKCI-IBGZPJMESA-N 0.000 description 1
• UXZDMXYRRQJIBJ-IBGZPJMESA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-(3-fluorophenyl)-n-[(3,4,5-trifluorophenyl)methyl]carbamate Chemical compound FC1=CC=CC(N(CC=2C=C(F)C(F)=C(F)C=2)C(=O)O[C@@H]2C3CCN(CC3)C2)=C1 UXZDMXYRRQJIBJ-IBGZPJMESA-N 0.000 description 1
• KOVBLMNQGVQJHN-IBGZPJMESA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-(4-fluoro-2-methylphenyl)-n-[(3-methylthiophen-2-yl)methyl]carbamate Chemical compound C1=CSC(CN(C(=O)O[C@@H]2C3CCN(CC3)C2)C=2C(=CC(F)=CC=2)C)=C1C KOVBLMNQGVQJHN-IBGZPJMESA-N 0.000 description 1
• OEFGLYQOZVHIOY-IBGZPJMESA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-(thiophen-3-ylmethyl)-n-[(2,4,5-trifluorophenyl)methyl]carbamate Chemical compound C1=C(F)C(F)=CC(F)=C1CN(C(=O)O[C@@H]1C2CCN(CC2)C1)CC1=CSC=C1 OEFGLYQOZVHIOY-IBGZPJMESA-N 0.000 description 1
• LJDVGEFNOREATI-KRWDZBQOSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-[(5-bromothiophen-2-yl)methyl]-n-(2,4,5-trifluorophenyl)carbamate Chemical compound C1=C(F)C(F)=CC(F)=C1N(C(=O)O[C@@H]1C2CCN(CC2)C1)CC1=CC=C(Br)S1 LJDVGEFNOREATI-KRWDZBQOSA-N 0.000 description 1
• CKNLSJBQGBWJBE-IBGZPJMESA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-[(5-ethylthiophen-2-yl)methyl]-n-[(3-methylthiophen-2-yl)methyl]carbamate Chemical compound S1C(CC)=CC=C1CN(C(=O)O[C@@H]1C2CCN(CC2)C1)CC1=C(C)C=CS1 CKNLSJBQGBWJBE-IBGZPJMESA-N 0.000 description 1
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