JP7383012B2 - ヘテロアリール置換スルホンアミド化合物、およびナトリウムチャネル阻害剤としてのその使用 - Google Patents

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Publication number

JP7383012B2

JP7383012B2 JP2021510446A JP2021510446A JP7383012B2 JP 7383012 B2 JP7383012 B2 JP 7383012B2 JP 2021510446 A JP2021510446 A JP 2021510446A JP 2021510446 A JP2021510446 A JP 2021510446A JP 7383012 B2 JP7383012 B2 JP 7383012B2

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JP

Japan

Prior art keywords

optionally substituted

alkyl

methyl

sulfonamide

formula

Prior art date

2018-08-31

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.)

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• -1 sulfonamide compounds Chemical class 0.000 title claims description 126
• 102000018674 Sodium Channels Human genes 0.000 title description 27
• 108010052164 Sodium Channels Proteins 0.000 title description 27
• 229940124530 sulfonamide Drugs 0.000 title description 15
• 239000003112 inhibitor Substances 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims description 783
• 125000000217 alkyl group Chemical group 0.000 claims description 330
• 239000001257 hydrogen Substances 0.000 claims description 281
• 229910052739 hydrogen Inorganic materials 0.000 claims description 281
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 171
• 239000000203 mixture Substances 0.000 claims description 160
• 238000000034 method Methods 0.000 claims description 147
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 135
• 125000001188 haloalkyl group Chemical group 0.000 claims description 106
• 150000003839 salts Chemical class 0.000 claims description 106
• 150000002431 hydrogen Chemical class 0.000 claims description 98
• 239000012453 solvate Substances 0.000 claims description 90
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 89
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 81
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 70
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 68
• 125000003107 substituted aryl group Chemical group 0.000 claims description 65
• 206010015037 epilepsy Diseases 0.000 claims description 59
• 125000002947 alkylene group Chemical group 0.000 claims description 58
• 201000010099 disease Diseases 0.000 claims description 51
• 239000008194 pharmaceutical composition Substances 0.000 claims description 50
• 241000124008 Mammalia Species 0.000 claims description 47
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 47
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 42
• 125000001072 heteroaryl group Chemical group 0.000 claims description 41
• 206010010904 Convulsion Diseases 0.000 claims description 39
• 230000000694 effects Effects 0.000 claims description 39
• 108010053752 Voltage-Gated Sodium Channels Proteins 0.000 claims description 38
• 125000000623 heterocyclic group Chemical group 0.000 claims description 38
• 102000016913 Voltage-Gated Sodium Channels Human genes 0.000 claims description 37
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 27
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 27
• 125000000335 thiazolyl group Chemical group 0.000 claims description 26
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 25
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 25
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 25
• 125000004076 pyridyl group Chemical group 0.000 claims description 24
• 230000002401 inhibitory effect Effects 0.000 claims description 20
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 208000028329 epileptic seizure Diseases 0.000 claims description 15
• DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 230000004907 flux Effects 0.000 claims description 11
• 150000002500 ions Chemical class 0.000 claims description 9
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
• KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims description 5
• RYQRIENXVZJZNK-KRWDZBQOSA-N 5-[[(3S)-1-[(2-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-4-methyl-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound FC1=C(CN2C[C@H](CC2)N(C=2C(=CC(=NC=2)S(=O)(=O)NC=2N=CSC=2)C)C)C=CC=C1 RYQRIENXVZJZNK-KRWDZBQOSA-N 0.000 claims description 5
• DJFUXPHZXBXNLT-SFHVURJKSA-N 5-[[(3S)-1-[(3-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-4-methyl-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound FC=1C=C(CN2C[C@H](CC2)N(C=2C(=CC(=NC=2)S(=O)(=O)NC=2N=CSC=2)C)C)C=CC=1 DJFUXPHZXBXNLT-SFHVURJKSA-N 0.000 claims description 4
• UVTKLEDYIBVKFF-SFHVURJKSA-N 5-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-4-methyl-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C=1C(=CC(=NC=1)S(=O)(=O)NC=1N=CSC=1)C)C UVTKLEDYIBVKFF-SFHVURJKSA-N 0.000 claims description 4
• DKJLBBQRXBDVCC-MRXNPFEDSA-N 3-fluoro-4-methyl-5-[1-[(1R)-1-phenylethyl]piperidin-4-yl]oxy-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound FC=1C(=NC=C(C=1C)OC1CCN(CC1)[C@H](C)C1=CC=CC=C1)S(=O)(=O)NC=1N=CSC=1 DKJLBBQRXBDVCC-MRXNPFEDSA-N 0.000 claims description 3
• RSAVKVUPOAKTAP-KRWDZBQOSA-N 3-fluoro-5-[[(3S)-1-[(2-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound FC=1C(=NC=C(C=1C)N(C)[C@@H]1CN(CC1)CC1=C(C=CC=C1)F)S(=O)(=O)NC1=NC(=CC=C1)F RSAVKVUPOAKTAP-KRWDZBQOSA-N 0.000 claims description 3
• OVYARDCMVLNIME-UHFFFAOYSA-N 3-fluoro-5-[[1-[(2-fluorophenyl)methyl]piperidin-4-yl]-methylamino]-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound FC=1C(=NC=C(C=1C)N(C)C1CCN(CC1)CC1=C(C=CC=C1)F)S(=O)(=O)NC1=NC(=CC=C1)F OVYARDCMVLNIME-UHFFFAOYSA-N 0.000 claims description 3
• BRNCCSABTKOFCT-GOSISDBHSA-N 3-fluoro-N-(6-fluoropyridin-2-yl)-4-methyl-5-[methyl-[1-[(1R)-1-phenylethyl]piperidin-4-yl]amino]pyridine-2-sulfonamide Chemical compound FC=1C(=NC=C(C=1C)N(C1CCN(CC1)[C@H](C)C1=CC=CC=C1)C)S(=O)(=O)NC1=NC(=CC=C1)F BRNCCSABTKOFCT-GOSISDBHSA-N 0.000 claims description 3
• PUYTUEYRQMDTSC-UHFFFAOYSA-N 4-[(1-benzylpiperidin-4-yl)-methylamino]-5-chloro-N-(6-fluoropyridin-2-yl)thiophene-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C=1C=C(SC=1Cl)S(=O)(=O)NC1=NC(=CC=C1)F)C PUYTUEYRQMDTSC-UHFFFAOYSA-N 0.000 claims description 3
• YIKJNPKJBVVXED-UHFFFAOYSA-N 4-[(1-benzylpiperidin-4-yl)-methylamino]-N-(6-fluoropyridin-2-yl)-5-methylthiophene-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C=1C=C(SC=1C)S(=O)(=O)NC1=NC(=CC=C1)F)C YIKJNPKJBVVXED-UHFFFAOYSA-N 0.000 claims description 3
• WGWQZIYFWVTYSK-QGZVFWFLSA-N 4-methyl-5-[1-[(1R)-1-phenylethyl]piperidin-4-yl]oxy-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound CC1=CC(=NC=C1OC1CCN(CC1)[C@H](C)C1=CC=CC=C1)S(=O)(=O)NC=1N=CSC=1 WGWQZIYFWVTYSK-QGZVFWFLSA-N 0.000 claims description 3
• XEULAQCJPRLGCH-MJGOQNOKSA-N 4-methyl-5-[methyl-[(3S)-1-[(1R)-1-phenylethyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound CC1=CC(=NC=C1N([C@@H]1CN(CC1)[C@H](C)C1=CC=CC=C1)C)S(=O)(=O)NC=1N=CSC=1 XEULAQCJPRLGCH-MJGOQNOKSA-N 0.000 claims description 3
• TXFKWTKEDQDMLS-KRWDZBQOSA-N 4-methyl-5-[methyl-[(3S)-1-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound C(C)(C)C=1SC=C(N=1)CN1C[C@H](CC1)N(C=1C(=CC(=NC=1)S(=O)(=O)NC=1N=CSC=1)C)C TXFKWTKEDQDMLS-KRWDZBQOSA-N 0.000 claims description 3
• GPVQUBTVOQYQDA-GOSISDBHSA-N 4-methyl-5-[methyl-[1-[(1R)-1-phenylethyl]piperidin-4-yl]amino]-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound CC1=CC(=NC=C1N(C1CCN(CC1)[C@H](C)C1=CC=CC=C1)C)S(=O)(=O)NC=1N=CSC=1 GPVQUBTVOQYQDA-GOSISDBHSA-N 0.000 claims description 3
• VTUSRSPUBDAVAP-UHFFFAOYSA-N 5-(1-benzylpiperidin-4-yl)oxy-4-methyl-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)OC=1C(=CC(=NC=1)S(=O)(=O)NC=1N=CSC=1)C VTUSRSPUBDAVAP-UHFFFAOYSA-N 0.000 claims description 3
• FJMBZYJJACPBPX-UHFFFAOYSA-N 5-(1-benzylpiperidin-4-yl)oxy-N-(1,3-thiazol-4-yl)-4-(trifluoromethyl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)OC=1C(=CC(=NC=1)S(=O)(=O)NC=1N=CSC=1)C(F)(F)F FJMBZYJJACPBPX-UHFFFAOYSA-N 0.000 claims description 3
• LOEIOUFEFDPFQL-UHFFFAOYSA-N 5-(1-benzylpiperidin-4-yl)oxy-N-(6-fluoropyridin-2-yl)-4-(trifluoromethyl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)OC=1C(=CC(=NC=1)S(=O)(=O)NC1=NC(=CC=C1)F)C(F)(F)F LOEIOUFEFDPFQL-UHFFFAOYSA-N 0.000 claims description 3
• HVHOCAKRYXUBFR-UHFFFAOYSA-N 5-(1-benzylpiperidin-4-yl)oxy-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)OC=1C(=CC(=NC=1)S(=O)(=O)NC1=NC(=CC=C1)F)C HVHOCAKRYXUBFR-UHFFFAOYSA-N 0.000 claims description 3
• IHFMJBPORBWZPE-UHFFFAOYSA-N 5-[(1-benzylpiperidin-4-yl)-methylamino]-3-fluoro-4-methyl-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C=1C(=C(C(=NC=1)S(=O)(=O)NC=1N=CSC=1)F)C)C IHFMJBPORBWZPE-UHFFFAOYSA-N 0.000 claims description 3
• OPLDBEPQSWHFQM-UHFFFAOYSA-N 5-[(1-benzylpiperidin-4-yl)-methylamino]-3-fluoro-N-(1,3-thiazol-4-yl)-4-(trifluoromethyl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C=1C(=C(C(=NC=1)S(=O)(=O)NC=1N=CSC=1)F)C(F)(F)F)C OPLDBEPQSWHFQM-UHFFFAOYSA-N 0.000 claims description 3
• QUHULGIHZLHSEE-UHFFFAOYSA-N 5-[(1-benzylpiperidin-4-yl)-methylamino]-3-fluoro-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C=1C(=C(C(=NC=1)S(=O)(=O)NC1=NC(=CC=C1)F)F)C)C QUHULGIHZLHSEE-UHFFFAOYSA-N 0.000 claims description 3
• FFYXKCTYHJPFJU-UHFFFAOYSA-N 5-[(1-benzylpiperidin-4-yl)-methylamino]-3-fluoro-N-(6-fluoropyridin-2-yl)-6-methylpyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C=1C=C(C(=NC=1C)S(=O)(=O)NC1=NC(=CC=C1)F)F)C FFYXKCTYHJPFJU-UHFFFAOYSA-N 0.000 claims description 3
• DLWRDQXPSVYUAE-UHFFFAOYSA-N 5-[(1-benzylpiperidin-4-yl)-methylamino]-4-methyl-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C=1C(=CC(=NC=1)S(=O)(=O)NC=1N=CSC=1)C)C DLWRDQXPSVYUAE-UHFFFAOYSA-N 0.000 claims description 3
• VBJIDHLXTVKFSL-UHFFFAOYSA-N 5-[(1-benzylpiperidin-4-yl)-methylamino]-N-(1,3-thiazol-4-yl)-4-(trifluoromethyl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C=1C(=CC(=NC=1)S(=O)(=O)NC=1N=CSC=1)C(F)(F)F)C VBJIDHLXTVKFSL-UHFFFAOYSA-N 0.000 claims description 3
• SWLHLTFLWZXZIH-UHFFFAOYSA-N 5-[(1-benzylpiperidin-4-yl)-methylamino]-N-(6-fluoropyridin-2-yl)-4-(trifluoromethyl)-1,3-thiazole-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C1=C(N=C(S1)S(=O)(=O)NC1=NC(=CC=C1)F)C(F)(F)F)C SWLHLTFLWZXZIH-UHFFFAOYSA-N 0.000 claims description 3
• CLFSCPAUCZAERY-UHFFFAOYSA-N 5-[(1-benzylpiperidin-4-yl)-methylamino]-N-(6-fluoropyridin-2-yl)-4-(trifluoromethyl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C=1C(=CC(=NC=1)S(=O)(=O)NC1=NC(=CC=C1)F)C(F)(F)F)C CLFSCPAUCZAERY-UHFFFAOYSA-N 0.000 claims description 3
• AMQJFTMGKNIINO-UHFFFAOYSA-N 5-[(1-benzylpiperidin-4-yl)-methylamino]-N-(6-fluoropyridin-2-yl)-4-methyl-1,3-thiazole-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C1=C(N=C(S1)S(=O)(=O)NC1=NC(=CC=C1)F)C)C AMQJFTMGKNIINO-UHFFFAOYSA-N 0.000 claims description 3
• AAWLKVCZTLVWDS-KRWDZBQOSA-N 5-[[(3S)-1-[(2,5-difluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-4-methyl-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound FC1=C(CN2C[C@H](CC2)N(C=2C(=CC(=NC=2)S(=O)(=O)NC=2N=CSC=2)C)C)C=C(C=C1)F AAWLKVCZTLVWDS-KRWDZBQOSA-N 0.000 claims description 3
• ZDUZWIILKLWKKB-INIZCTEOSA-N 5-[[(3S)-1-[(4-cyclopropyl-1,3-thiazol-2-yl)methyl]pyrrolidin-3-yl]-methylamino]-4-methyl-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound N(C)(C1=C(C=C(N=C1)S(=O)(=O)NC=1N=CSC=1)C)[C@H]1CCN(C1)CC1=NC(C2CC2)=CS1 ZDUZWIILKLWKKB-INIZCTEOSA-N 0.000 claims description 3
• CNAHEFHKJNPJSB-HNNXBMFYSA-N 5-[[(3S)-1-[[1-(difluoromethyl)pyrazol-3-yl]methyl]pyrrolidin-3-yl]-methylamino]-4-methyl-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound FC(N1N=C(C=C1)CN1C[C@H](CC1)N(C=1C(=CC(=NC=1)S(=O)(=O)NC=1N=CSC=1)C)C)F CNAHEFHKJNPJSB-HNNXBMFYSA-N 0.000 claims description 3
• RLTVQPTYWXWWPV-SFHVURJKSA-N 5-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-3-fluoro-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C=1C(=C(C(=NC=1)S(=O)(=O)NC1=NC(=CC=C1)F)F)C)C RLTVQPTYWXWWPV-SFHVURJKSA-N 0.000 claims description 3
• TWQUCFJAUXUMQF-INIZCTEOSA-N 5-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-4-(difluoromethyl)-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C=1C(=CC(=NC=1)S(=O)(=O)NC=1N=CSC=1)C(F)F)C TWQUCFJAUXUMQF-INIZCTEOSA-N 0.000 claims description 3
• ODGXYSJPMZSCEK-SFHVURJKSA-N 5-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-4-methyl-N-(1,2-thiazol-3-yl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C=1C(=CC(=NC=1)S(=O)(=O)NC1=NSC=C1)C)C ODGXYSJPMZSCEK-SFHVURJKSA-N 0.000 claims description 3
• LPVNIMONLMBGBU-SFHVURJKSA-N 5-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-6-methyl-N-(1,3-thiazol-4-yl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C=1C=CC(=NC=1C)S(=O)(=O)NC=1N=CSC=1)C LPVNIMONLMBGBU-SFHVURJKSA-N 0.000 claims description 3
• KFVONUQMFLKFLK-INIZCTEOSA-N 5-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)-4-(trifluoromethyl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C=1C(=CC(=NC=1)S(=O)(=O)NC=1N=CSC=1)C(F)(F)F)C KFVONUQMFLKFLK-INIZCTEOSA-N 0.000 claims description 3
• QQWICYYXCHMGMZ-IBGZPJMESA-N 5-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-N-(6-fluoropyridin-2-yl)-4-methylpyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C=1C(=CC(=NC=1)S(=O)(=O)NC1=NC(=CC=C1)F)C)C QQWICYYXCHMGMZ-IBGZPJMESA-N 0.000 claims description 3
• YNQLJLLZKKMQSJ-HNNXBMFYSA-N 5-[[(3S)-1-benzylpyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)-4-(trifluoromethyl)pyridine-2-sulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)NC=1C(=CC(=NC=1)S(=O)(=O)NC=1N=CSC=1)C(F)(F)F YNQLJLLZKKMQSJ-HNNXBMFYSA-N 0.000 claims description 3
• XCVXMOSTQLIATQ-MRXNPFEDSA-N 5-[[1-[(1R)-1-(2-fluorophenyl)ethyl]piperidin-4-yl]-methylamino]-N-(6-fluoropyridin-2-yl)-4-methyl-1,3-thiazole-2-sulfonamide Chemical compound FC1=C(C=CC=C1)[C@@H](C)N1CCC(CC1)N(C1=C(N=C(S1)S(=O)(=O)NC1=NC(=CC=C1)F)C)C XCVXMOSTQLIATQ-MRXNPFEDSA-N 0.000 claims description 3
• UNVIEINZNCZQGZ-UHFFFAOYSA-N 5-[[1-[(2,5-difluorophenyl)methyl]piperidin-4-yl]-methylamino]-N-(1,3-thiazol-4-yl)-4-(trifluoromethyl)pyridine-2-sulfonamide Chemical compound FC1=C(CN2CCC(CC2)N(C=2C(=CC(=NC=2)S(=O)(=O)NC=2N=CSC=2)C(F)(F)F)C)C=C(C=C1)F UNVIEINZNCZQGZ-UHFFFAOYSA-N 0.000 claims description 3
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