AU2008356409B2 - Quinuclidine derivatives as muscarinic M3 receptor antagonists - Google Patents

Info

Publication number

AU2008356409B2

AU2008356409B2 AU2008356409A AU2008356409A AU2008356409B2 AU 2008356409 B2 AU2008356409 B2 AU 2008356409B2 AU 2008356409 A AU2008356409 A AU 2008356409A AU 2008356409 A AU2008356409 A AU 2008356409A AU 2008356409 B2 AU2008356409 B2 AU 2008356409B2

Authority

AU

Australia

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.)

Ceased

Links

• Espacenet
• Global Dossier
• Discuss

• 229940122694 Muscarinic M3 receptor antagonist Drugs 0.000 title 1
• 239000003681 muscarinic M3 receptor antagonist Substances 0.000 title 1
• 150000008584 quinuclidines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 248
• 238000011282 treatment Methods 0.000 claims abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 17
• 238000004519 manufacturing process Methods 0.000 claims abstract description 11
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 9
• SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims abstract description 5
• -1 6-Methyl-pyridin-3-ylcarbamoyl Chemical group 0.000 claims description 84
• 238000000034 method Methods 0.000 claims description 44
• 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
• 208000006673 asthma Diseases 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 229940127557 pharmaceutical product Drugs 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 12
• 241001465754 Metazoa Species 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 11
• 150000001450 anions Chemical class 0.000 claims description 11
• 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
• 241000124008 Mammalia Species 0.000 claims description 6
• 229940124750 glucocorticoid receptor agonist Drugs 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 230000003637 steroidlike Effects 0.000 claims description 6
• 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
• GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 102000020233 phosphotransferase Human genes 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• ADCKYXTWKHFAIF-XOPUIGJFSA-O [(3r)-1-[2-[2-(3-fluorophenoxy)ethylamino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound FC1=CC=CC(OCCNC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2C=CC=CC=2)=C1 ADCKYXTWKHFAIF-XOPUIGJFSA-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
• WZKCUYWQFWEJSC-AKFGGTECSA-O [(3r)-1-[2-oxo-2-(pyridin-2-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=1N=CC=CC=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 WZKCUYWQFWEJSC-AKFGGTECSA-O 0.000 claims description 2
• LVPSGBXQSUVRGV-LMEDFRRQSA-O [(3r)-1-[2-oxo-2-(pyridin-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=CN=CC=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 LVPSGBXQSUVRGV-LMEDFRRQSA-O 0.000 claims description 2
• ZJWZVDHWCDIUEQ-HBUOLCFLSA-O [(3r)-1-[2-oxo-2-(pyrimidin-2-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=1N=CC=CN=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 ZJWZVDHWCDIUEQ-HBUOLCFLSA-O 0.000 claims description 2
• HOKQUUQXQVTPAL-HBUOLCFLSA-O [(3r)-1-[2-oxo-2-(pyrimidin-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=1N=CN=CC=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 HOKQUUQXQVTPAL-HBUOLCFLSA-O 0.000 claims description 2
• AGZJDEDTIYMPHM-UYXPAWESSA-O [(3r)-1-[2-oxo-2-(pyrimidin-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=1C=NC=NC=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 AGZJDEDTIYMPHM-UYXPAWESSA-O 0.000 claims description 2
• UWXPRCSQCGFXDJ-REUUHXOVSA-O [(3r)-1-[2-oxo-2-[[6-(trifluoromethyl)pyridin-2-yl]amino]ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2C=CC=CC=2)=N1 UWXPRCSQCGFXDJ-REUUHXOVSA-O 0.000 claims description 2
• IEVMTZSLCPGAQR-DQXUUOSFSA-N [(3r)-1-[3-(4-cyanophenoxy)propyl]-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+]21CCCOC1=CC=C(C#N)C=C1 IEVMTZSLCPGAQR-DQXUUOSFSA-N 0.000 claims description 2
• FMRJFBVIMHOAPF-DPPLCSQNSA-N [(3s)-1-(3-phenoxypropyl)-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+]21CCCOC1=CC=CC=C1 FMRJFBVIMHOAPF-DPPLCSQNSA-N 0.000 claims description 2
• 238000002156 mixing Methods 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 1
• 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 1
• 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 1
• SNWDRXJIILIOII-KRXIBUGQSA-O [(3r)-1-[2-(4-methylanilino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound C1=CC(C)=CC=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 SNWDRXJIILIOII-KRXIBUGQSA-O 0.000 claims 1
• 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 1
• 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 1
• ILQZJPKOIMGJOM-LMEDFRRQSA-O [(3r)-1-[2-oxo-2-(pyridin-3-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=NC=CC=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 ILQZJPKOIMGJOM-LMEDFRRQSA-O 0.000 claims 1
• IZCYOTUDBSSMCK-BUNRZTFGSA-O [(3r)-1-[2-oxo-2-[[6-(trifluoromethyl)pyridazin-3-yl]amino]ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound N1=NC(C(F)(F)F)=CC=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 IZCYOTUDBSSMCK-BUNRZTFGSA-O 0.000 claims 1
• 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 abstract description 6
• 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 abstract description 6
• 230000001404 mediated effect Effects 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 309
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 154
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 141
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 136
• 239000007787 solid Substances 0.000 description 131
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 119
• 238000005481 NMR spectroscopy Methods 0.000 description 116
• 239000011541 reaction mixture Substances 0.000 description 92
• VOWQGVADNCNFKU-IBGZPJMESA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 VOWQGVADNCNFKU-IBGZPJMESA-N 0.000 description 76
• 239000000203 mixture Substances 0.000 description 75
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
• 239000000243 solution Substances 0.000 description 69
• 229910001868 water Inorganic materials 0.000 description 63
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
• 235000019439 ethyl acetate Nutrition 0.000 description 54
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
• 238000010898 silica gel chromatography Methods 0.000 description 42
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 38
• 239000012044 organic layer Substances 0.000 description 37
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
• 238000006243 chemical reaction Methods 0.000 description 33
• 239000010410 layer Substances 0.000 description 30
• 239000003921 oil Substances 0.000 description 29
• 235000019198 oils Nutrition 0.000 description 29
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
• 125000000217 alkyl group Chemical group 0.000 description 28
• 238000003756 stirring Methods 0.000 description 28
• 229910052757 nitrogen Inorganic materials 0.000 description 27
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 26
• 229960005419 nitrogen Drugs 0.000 description 26
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
• 239000012043 crude product Substances 0.000 description 24
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 20
• LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 19
• 238000010992 reflux Methods 0.000 description 19
• VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 18
• 239000013078 crystal Substances 0.000 description 18
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
• 239000003795 chemical substances by application Substances 0.000 description 17
• 235000019341 magnesium sulphate Nutrition 0.000 description 17
• 238000000746 purification Methods 0.000 description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 15
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
• 239000012071 phase Substances 0.000 description 13
• 229910000027 potassium carbonate Inorganic materials 0.000 description 13
• 239000000725 suspension Substances 0.000 description 13
• DEFBPPYKOPTXIJ-UHFFFAOYSA-N 1-phenylcycloheptane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCCCCC1 DEFBPPYKOPTXIJ-UHFFFAOYSA-N 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• IIGOBGCDNPRZDU-INIZCTEOSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] 1-thiophen-2-ylcycloheptane-1-carboxylate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)C1(C=2SC=CC=2)CCCCCC1 IIGOBGCDNPRZDU-INIZCTEOSA-N 0.000 description 12
• 239000005557 antagonist Substances 0.000 description 12
• 238000004440 column chromatography Methods 0.000 description 12
• 229910052736 halogen Inorganic materials 0.000 description 12
• 150000002367 halogens Chemical class 0.000 description 12
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
• 125000001424 substituent group Chemical group 0.000 description 12
• JJMRJPAPJCFDAM-UHFFFAOYSA-N 2-chloro-n-pyridin-2-ylacetamide Chemical compound ClCC(=O)NC1=CC=CC=N1 JJMRJPAPJCFDAM-UHFFFAOYSA-N 0.000 description 11
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
• 230000027455 binding Effects 0.000 description 11
• 239000000377 silicon dioxide Substances 0.000 description 11
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• 230000001154 acute effect Effects 0.000 description 10
• 238000013459 approach Methods 0.000 description 10
• 201000010099 disease Diseases 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
• 238000000634 powder X-ray diffraction Methods 0.000 description 10
• 239000003039 volatile agent Substances 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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• CMSOWTAJRISGOS-XDVWKIBCSA-N [(3r)-1-[2-(2-fluoroanilino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate;bromide Chemical compound [Br-].FC1=CC=CC=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 CMSOWTAJRISGOS-XDVWKIBCSA-N 0.000 description 1
• FXVQCJVHWVZEMS-GLSBDXMNSA-N [(3r)-1-[2-(2-methylanilino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate;bromide Chemical compound [Br-].CC1=CC=CC=C1NC(=O)C[N+]1(C[C@@H]2OC(=O)C3(CCCCCC3)C=3C=CC=CC=3)CCC2CC1 FXVQCJVHWVZEMS-GLSBDXMNSA-N 0.000 description 1
• 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 description 1
• PTAYXJFBLHSYDR-YJSSFVECSA-N [(3r)-1-[2-(3,5-difluoroanilino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate;bromide Chemical compound [Br-].FC1=CC(F)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(CCCCCC2)C=2C=CC=CC=2)=C1 PTAYXJFBLHSYDR-YJSSFVECSA-N 0.000 description 1
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• OIXUASDYSNTQAN-MVIHUCQCSA-N [(3r)-1-[2-(pyridine-2-carbonylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-phenylcycloheptane-1-carboxylate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(C1)CCNC(=O)C=1N=CC=CC=1)C(=O)C1(C=2C=CC=CC=2)CCCCCC1 OIXUASDYSNTQAN-MVIHUCQCSA-N 0.000 description 1
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