JP2019516737A5

JP2019516737A5 -

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Publication number: JP2019516737A5
Authority: JP; Japan
Prior art keywords: methyl; amino; benzenesulfonamide; thiazol; fluoro
Prior art date: 2017-05-19
Legal status : Granted

Application number

JP2018560884A

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English (en)

Japanese (ja)

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JP2019516737A (ja

JP6938545B2 (ja

Filing date

2017-05-19

Publication date

2020-06-25

2017-05-19 Application filed filed Critical

2017-05-19 Priority claimed from PCT/US2017/033634 external-priority patent/WO2017201468A1/en

2019-06-20 Publication of JP2019516737A publication Critical patent/JP2019516737A/ja

2020-06-25 Publication of JP2019516737A5 publication Critical patent/JP2019516737A5/ja

2021-09-01 Priority to JP2021142186A priority Critical patent/JP2021185189A/ja

2021-09-22 Application granted granted Critical

2021-09-22 Publication of JP6938545B2 publication Critical patent/JP6938545B2/ja

Status Active legal-status Critical Current

2037-05-19 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims description 143
150000003839 salts Chemical class 0.000 claims description 84
239000012453 solvate Substances 0.000 claims description 74
125000000217 alkyl group Chemical group 0.000 claims description 66
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 58
229910052739 hydrogen Inorganic materials 0.000 claims description 49
239000001257 hydrogen Substances 0.000 claims description 49
150000002431 hydrogen Chemical class 0.000 claims description 45
125000001188 haloalkyl group Chemical group 0.000 claims description 37
239000000203 mixture Substances 0.000 claims description 37
125000003710 aryl alkyl group Chemical group 0.000 claims description 29
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 26
125000003118 aryl group Chemical group 0.000 claims description 23
125000003107 substituted aryl group Chemical group 0.000 claims description 23
150000001408 amides Chemical class 0.000 claims description 22
125000002947 alkylene group Chemical group 0.000 claims description 21
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 21
125000005843 halogen group Chemical group 0.000 claims description 20
125000000623 heterocyclic group Chemical group 0.000 claims description 18
125000001113 thiadiazolyl group Chemical group 0.000 claims description 16
125000000335 thiazolyl group Chemical group 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 14
125000000842 isoxazolyl group Chemical group 0.000 claims description 14
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 12
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
125000001072 heteroaryl group Chemical group 0.000 claims description 11
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 8
206010015037 epilepsy Diseases 0.000 claims description 8
-1 trimethylsilanyl Chemical group 0.000 claims description 7
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 5
HNOCOLAFLBICIU-KRWDZBQOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-2,6-difluoro-3-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=C(C(=C(C(=C1)F)S(=O)(=O)NC=1N=CSC=1)F)C)C HNOCOLAFLBICIU-KRWDZBQOSA-N 0.000 claims description 4
GUBDMIDNRVTGRF-SFHVURJKSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-2-fluoro-3-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=C(C(=C(C=C1)S(=O)(=O)NC=1N=CSC=1)F)C)C GUBDMIDNRVTGRF-SFHVURJKSA-N 0.000 claims description 4
OZSYKDBMNQAWEN-SFHVURJKSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,2-thiazol-3-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC1=NSC=C1)F)C OZSYKDBMNQAWEN-SFHVURJKSA-N 0.000 claims description 4
UCSHINHOAVARGQ-SFHVURJKSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F)C UCSHINHOAVARGQ-SFHVURJKSA-N 0.000 claims description 4
WWVPJQZQMFPHCX-INIZCTEOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-5-bromo-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C=C1Br)S(=O)(=O)NC=1N=CSC=1)F)C WWVPJQZQMFPHCX-INIZCTEOSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
206010010904 Convulsion Diseases 0.000 claims description 3
208000028329 epileptic seizure Diseases 0.000 claims description 3
SXKMQBMMBOPKEZ-HNNXBMFYSA-N 2,6-difluoro-3-methyl-4-[methyl-[(3S)-1-[[6-(trifluoromethyl)pyridin-2-yl]methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C(=CC(=C1C)N([C@@H]1CN(CC1)CC1=NC(=CC=C1)C(F)(F)F)C)F)S(=O)(=O)NC=1N=CSC=1 SXKMQBMMBOPKEZ-HNNXBMFYSA-N 0.000 claims description 2
JMRZDHWIINGZKK-INIZCTEOSA-N 2,6-difluoro-4-[[(3S)-1-[(2-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-3-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C(=CC(=C1C)N(C)[C@@H]1CN(CC1)CC1=C(C=CC=C1)F)F)S(=O)(=O)NC=1N=CSC=1 JMRZDHWIINGZKK-INIZCTEOSA-N 0.000 claims description 2
MCZUVSMKLIOVFW-KRWDZBQOSA-N 2,6-difluoro-4-[[(3S)-1-[(3-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-3-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C(=CC(=C1C)N(C)[C@@H]1CN(CC1)CC1=CC(=CC=C1)F)F)S(=O)(=O)NC=1N=CSC=1 MCZUVSMKLIOVFW-KRWDZBQOSA-N 0.000 claims description 2
SFYUPMFOEIBHEO-SFHVURJKSA-N 2-fluoro-4-[[(3S)-1-[(2-fluoro-3-methylphenyl)methyl]pyrrolidin-3-yl]-methylamino]-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N(C)[C@@H]1CN(CC1)CC1=C(C(=CC=C1)C)F)C)S(=O)(=O)NC=1N=CSC=1 SFYUPMFOEIBHEO-SFHVURJKSA-N 0.000 claims description 2
RVIAJECZWSHVFF-KRWDZBQOSA-N 2-fluoro-4-[[(3S)-1-[(2-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N(C)[C@@H]1CN(CC1)CC1=C(C=CC=C1)F)C)S(=O)(=O)NC=1N=CSC=1 RVIAJECZWSHVFF-KRWDZBQOSA-N 0.000 claims description 2
WNLZKQSUQRXEPA-KRWDZBQOSA-N 2-fluoro-4-[[(3S)-1-[(2-hydroxyphenyl)methyl]pyrrolidin-3-yl]-methylamino]-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N(C)[C@@H]1CN(CC1)CC1=C(C=CC=C1)O)C)S(=O)(=O)NC=1N=CSC=1 WNLZKQSUQRXEPA-KRWDZBQOSA-N 0.000 claims description 2
BDTNKVDLIDNNMC-SFHVURJKSA-N 2-fluoro-4-[[(3S)-1-[(2-methoxyphenyl)methyl]pyrrolidin-3-yl]-methylamino]-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N(C)[C@@H]1CN(CC1)CC1=C(C=CC=C1)OC)C)S(=O)(=O)NC=1N=CSC=1 BDTNKVDLIDNNMC-SFHVURJKSA-N 0.000 claims description 2
OMRSEARSOZVCNM-INIZCTEOSA-N 2-fluoro-4-[[(3S)-1-[(3-fluoro-6-methylpyridin-2-yl)methyl]pyrrolidin-3-yl]-methylamino]-3-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=CC(=C1C)N(C)[C@@H]1CN(CC1)CC1=NC(=CC=C1F)C)S(=O)(=O)NC=1N=CSC=1 OMRSEARSOZVCNM-INIZCTEOSA-N 0.000 claims description 2
GQBIUYQZBTXKCI-INIZCTEOSA-N 2-fluoro-4-[[(3S)-1-[(3-fluoro-6-methylpyridin-2-yl)methyl]pyrrolidin-3-yl]-methylamino]-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N(C)[C@@H]1CN(CC1)CC1=NC(=CC=C1F)C)C)S(=O)(=O)NC=1N=CSC=1 GQBIUYQZBTXKCI-INIZCTEOSA-N 0.000 claims description 2
AYYLGCHNORVESF-SFHVURJKSA-N 2-fluoro-4-[[(3S)-1-[(3-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N(C)[C@@H]1CN(CC1)CC1=CC(=CC=C1)F)C)S(=O)(=O)NC=1N=CSC=1 AYYLGCHNORVESF-SFHVURJKSA-N 0.000 claims description 2
AXWTUCSIBGJUCC-KRWDZBQOSA-N 2-fluoro-4-[[(3S)-1-[(3-hydroxyphenyl)methyl]pyrrolidin-3-yl]-methylamino]-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N(C)[C@@H]1CN(CC1)CC1=CC(=CC=C1)O)C)S(=O)(=O)NC=1N=CSC=1 AXWTUCSIBGJUCC-KRWDZBQOSA-N 0.000 claims description 2
MYBZEGQXAHHUNE-KRWDZBQOSA-N 2-fluoro-4-[[(3S)-1-[(4-hydroxyphenyl)methyl]pyrrolidin-3-yl]-methylamino]-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N(C)[C@@H]1CN(CC1)CC1=CC=C(C=C1)O)C)S(=O)(=O)NC=1N=CSC=1 MYBZEGQXAHHUNE-KRWDZBQOSA-N 0.000 claims description 2
VCLGXGWFSJUHNO-HNNXBMFYSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-(1,3-oxazol-4-ylmethyl)pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC=1N=COC=1)C)C)S(=O)(=O)NC=1N=CSC=1 VCLGXGWFSJUHNO-HNNXBMFYSA-N 0.000 claims description 2
IKROIAHQZBAUNM-AWEZNQCLSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-(1,3-thiazol-2-ylmethyl)pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC=1SC=CN=1)C)C)S(=O)(=O)NC=1N=CSC=1 IKROIAHQZBAUNM-AWEZNQCLSA-N 0.000 claims description 2
VPMFTZHGMWVYLA-HNNXBMFYSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-(1,3-thiazol-4-ylmethyl)pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC=1N=CSC=1)C)C)S(=O)(=O)NC=1N=CSC=1 VPMFTZHGMWVYLA-HNNXBMFYSA-N 0.000 claims description 2
NEGPUMQIHNEADR-IBGZPJMESA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-(2-phenylethyl)pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CCC1=CC=CC=C1)C)C)S(=O)(=O)NC=1N=CSC=1 NEGPUMQIHNEADR-IBGZPJMESA-N 0.000 claims description 2
CNJDHZWCBTZZJF-IBGZPJMESA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-ylmethyl)pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC1=NN2C(CCCC2)=C1)C)C)S(=O)(=O)NC=1N=CSC=1 CNJDHZWCBTZZJF-IBGZPJMESA-N 0.000 claims description 2
JPBDKQCYDKIOLW-IBGZPJMESA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-(pyrazolo[1,5-a]pyridin-2-ylmethyl)pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC1=NN2C(C=CC=C2)=C1)C)C)S(=O)(=O)NC=1N=CSC=1 JPBDKQCYDKIOLW-IBGZPJMESA-N 0.000 claims description 2
XUHTVHWLFKLPKA-KRWDZBQOSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC1=NC=CC=C1)C)C)S(=O)(=O)NC=1N=CSC=1 XUHTVHWLFKLPKA-KRWDZBQOSA-N 0.000 claims description 2
ZJUIZFGNZTZVNS-INIZCTEOSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-[(2-methyl-1,3-oxazol-4-yl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC=1N=C(OC=1)C)C)C)S(=O)(=O)NC=1N=CSC=1 ZJUIZFGNZTZVNS-INIZCTEOSA-N 0.000 claims description 2
FSJFIKLZMJAZHH-IBGZPJMESA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-[(2-methylphenyl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC1=C(C=CC=C1)C)C)C)S(=O)(=O)NC=1N=CSC=1 FSJFIKLZMJAZHH-IBGZPJMESA-N 0.000 claims description 2
PKBLNJQHGWHMLE-FQEVSTJZSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-[(2-phenyl-1,3-thiazol-4-yl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC=1N=C(SC=1)C1=CC=CC=C1)C)C)S(=O)(=O)NC=1N=CSC=1 PKBLNJQHGWHMLE-FQEVSTJZSA-N 0.000 claims description 2
YZAOPSMSRVIYJT-HNNXBMFYSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-[(4-methyl-1,3-oxazol-2-yl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC=1OC=C(N=1)C)C)C)S(=O)(=O)NC=1N=CSC=1 YZAOPSMSRVIYJT-HNNXBMFYSA-N 0.000 claims description 2
YQUPJKLEJYAKKK-HNNXBMFYSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-[(4-methyl-1,3-thiazol-2-yl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC=1SC=C(N=1)C)C)C)S(=O)(=O)NC=1N=CSC=1 YQUPJKLEJYAKKK-HNNXBMFYSA-N 0.000 claims description 2
KNEJGFDKABZVQJ-INIZCTEOSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-[(5-methylfuran-2-yl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC=1OC(=CC=1)C)C)C)S(=O)(=O)NC=1N=CSC=1 KNEJGFDKABZVQJ-INIZCTEOSA-N 0.000 claims description 2
WZUZFHXWPYKMFC-INIZCTEOSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-[[1-(2,2,2-trifluoroethyl)pyrazol-3-yl]methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC1=NN(C=C1)CC(F)(F)F)C)C)S(=O)(=O)NC=1N=CSC=1 WZUZFHXWPYKMFC-INIZCTEOSA-N 0.000 claims description 2
YOEAFTQECPSLGP-HNNXBMFYSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-[[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC1=CC=NN1CC(F)(F)F)C)C)S(=O)(=O)NC=1N=CSC=1 YOEAFTQECPSLGP-HNNXBMFYSA-N 0.000 claims description 2
WKSWFYVKUUHFGO-AWEZNQCLSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-[[2-(trifluoromethyl)-1,3-thiazol-4-yl]methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC=1N=C(SC=1)C(F)(F)F)C)C)S(=O)(=O)NC=1N=CSC=1 WKSWFYVKUUHFGO-AWEZNQCLSA-N 0.000 claims description 2
ODMSQVRRGMVXCI-AWEZNQCLSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-[[2-methyl-5-(trifluoromethyl)-1,3-oxazol-4-yl]methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC=1N=C(OC=1C(F)(F)F)C)C)C)S(=O)(=O)NC=1N=CSC=1 ODMSQVRRGMVXCI-AWEZNQCLSA-N 0.000 claims description 2
QIHUVPFPZWJAQZ-ZDUSSCGKSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-[[4-(trifluoromethyl)-1,3-thiazol-2-yl]methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC=1SC=C(N=1)C(F)(F)F)C)C)S(=O)(=O)NC=1N=CSC=1 QIHUVPFPZWJAQZ-ZDUSSCGKSA-N 0.000 claims description 2
DNIZSMWPXKBXDJ-AWEZNQCLSA-N 2-fluoro-5-methyl-4-[methyl-[(3S)-1-[[5-(trifluoromethyl)furan-2-yl]methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC=1OC(=CC=1)C(F)(F)F)C)C)S(=O)(=O)NC=1N=CSC=1 DNIZSMWPXKBXDJ-AWEZNQCLSA-N 0.000 claims description 2
SUUGGLCRMKIDCF-GOSISDBHSA-N 2-fluoro-5-methyl-4-[methyl-[1-[(1R)-1-phenylethyl]piperidin-4-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N(C1CCN(CC1)[C@H](C)C1=CC=CC=C1)C)C)S(=O)(=O)NC=1N=CSC=1 SUUGGLCRMKIDCF-GOSISDBHSA-N 0.000 claims description 2
CHUDGNRDARIVIH-HNNXBMFYSA-N 3-chloro-2,6-difluoro-4-[methyl-[(3S)-1-[(6-methylpyridin-2-yl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=C(C(=CC=1N([C@@H]1CN(CC1)CC1=NC(=CC=C1)C)C)F)S(=O)(=O)NC=1N=CSC=1)F CHUDGNRDARIVIH-HNNXBMFYSA-N 0.000 claims description 2
VOKQIKSPDIJNJB-RDJZCZTQSA-N 3-chloro-2-fluoro-N-(6-fluoropyridin-2-yl)-4-[[(3S)-1-[(1S)-1-phenylethyl]pyrrolidin-3-yl]amino]benzenesulfonamide Chemical compound ClC=1C(=C(C=CC=1N[C@@H]1CN(CC1)[C@@H](C)C1=CC=CC=C1)S(=O)(=O)NC1=NC(=CC=C1)F)F VOKQIKSPDIJNJB-RDJZCZTQSA-N 0.000 claims description 2
OJVOTCPGNIMSNG-OAHLLOKOSA-N 3-chloro-4-[[(3R)-1-[(2-fluorophenyl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1N[C@H]1CN(CC1)CC1=C(C=CC=C1)F)S(=O)(=O)NC=1SC=CN=1 OJVOTCPGNIMSNG-OAHLLOKOSA-N 0.000 claims description 2
HZPTZJQNSFSZKU-MRXNPFEDSA-N 3-chloro-4-[[(3R)-1-[(3-chlorophenyl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1N[C@H]1CN(CC1)CC1=CC(=CC=C1)Cl)S(=O)(=O)NC=1SC=CN=1 HZPTZJQNSFSZKU-MRXNPFEDSA-N 0.000 claims description 2
CKFUPVGLXCXQKS-QGZVFWFLSA-N 3-chloro-4-[[(3R)-1-[(3-methylphenyl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1N[C@H]1CN(CC1)CC1=CC(=CC=C1)C)S(=O)(=O)NC=1SC=CN=1 CKFUPVGLXCXQKS-QGZVFWFLSA-N 0.000 claims description 2
DPHDXIHKQSBLIQ-WMZOPIPTSA-N 3-chloro-4-[[(3S)-1-[(1S)-2,3-dihydro-1H-inden-1-yl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=C(C=CC=1N(C)[C@@H]1CN(CC1)[C@H]1CCC2=CC=CC=C12)S(=O)(=O)NC=1N=CSC=1)F DPHDXIHKQSBLIQ-WMZOPIPTSA-N 0.000 claims description 2
FOUHCIMZPGVJLK-QFIPXVFZSA-N 3-chloro-4-[[(3S)-1-[(2-fluoro-5-methylphenyl)methyl]-3-methylpyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1N[C@@]1(CN(CC1)CC1=C(C=CC(=C1)C)F)C)S(=O)(=O)NC=1N=CSC=1 FOUHCIMZPGVJLK-QFIPXVFZSA-N 0.000 claims description 2
WCURWKBDZLIGDL-KRWDZBQOSA-N 3-chloro-4-[[(3S)-1-[(3-chlorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1N(C)[C@@H]1CN(CC1)CC1=CC(=CC=C1)Cl)S(=O)(=O)NC=1SC=CN=1 WCURWKBDZLIGDL-KRWDZBQOSA-N 0.000 claims description 2
XINHDDMQPYHSAU-INIZCTEOSA-N 3-chloro-4-[[(3S)-1-[(5-chloro-2-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1N(C)[C@@H]1CN(CC1)CC1=C(C=CC(=C1)Cl)F)S(=O)(=O)NC=1N=CSC=1 XINHDDMQPYHSAU-INIZCTEOSA-N 0.000 claims description 2
ZTRURHABBFJPPY-KRWDZBQOSA-N 3-chloro-4-[[(3S)-1-[[3-(difluoromethyl)phenyl]methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1N(C)[C@@H]1CN(CC1)CC1=CC(=CC=C1)C(F)F)S(=O)(=O)NC=1SC=CN=1 ZTRURHABBFJPPY-KRWDZBQOSA-N 0.000 claims description 2
JNDLJVZRHHUFHP-KRWDZBQOSA-N 3-chloro-4-[[(3S)-1-[[3-(difluoromethyl)phenyl]methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1N(C)[C@@H]1CN(CC1)CC1=CC(=CC=C1)C(F)F)S(=O)(=O)NC=1N=CSC=1 JNDLJVZRHHUFHP-KRWDZBQOSA-N 0.000 claims description 2
BJHKESOKFRPALP-SFHVURJKSA-N 3-chloro-4-[methyl-[(3S)-1-(2-phenylpropan-2-yl)pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1N([C@@H]1CN(CC1)C(C)(C)C1=CC=CC=C1)C)S(=O)(=O)NC=1N=CSC=1 BJHKESOKFRPALP-SFHVURJKSA-N 0.000 claims description 2
CZWFPNHIOMKGHV-AEFFLSMTSA-N 3-chloro-4-[methyl-[(3S)-1-[(1R)-1-phenylethyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1N([C@@H]1CN(CC1)[C@H](C)C1=CC=CC=C1)C)S(=O)(=O)NC=1SC=CN=1 CZWFPNHIOMKGHV-AEFFLSMTSA-N 0.000 claims description 2
QKIPEOQCVFJQTI-AEFFLSMTSA-N 3-chloro-4-[methyl-[(3S)-1-[(1R)-1-phenylethyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1N([C@@H]1CN(CC1)[C@H](C)C1=CC=CC=C1)C)S(=O)(=O)NC=1N=CSC=1 QKIPEOQCVFJQTI-AEFFLSMTSA-N 0.000 claims description 2
CZWFPNHIOMKGHV-WMZOPIPTSA-N 3-chloro-4-[methyl-[(3S)-1-[(1S)-1-phenylethyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1N([C@@H]1CN(CC1)[C@@H](C)C1=CC=CC=C1)C)S(=O)(=O)NC=1SC=CN=1 CZWFPNHIOMKGHV-WMZOPIPTSA-N 0.000 claims description 2
QKIPEOQCVFJQTI-WMZOPIPTSA-N 3-chloro-4-[methyl-[(3S)-1-[(1S)-1-phenylethyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1N([C@@H]1CN(CC1)[C@@H](C)C1=CC=CC=C1)C)S(=O)(=O)NC=1N=CSC=1 QKIPEOQCVFJQTI-WMZOPIPTSA-N 0.000 claims description 2
XBCBOCLSBWFNRH-UHFFFAOYSA-N 4-(1-benzylazetidin-3-yl)oxy-3-chloro-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1CC(C1)OC1=C(C=C(C=C1)S(=O)(=O)NC=1SC=CN=1)Cl XBCBOCLSBWFNRH-UHFFFAOYSA-N 0.000 claims description 2
OFKCOGYFJSZGET-UHFFFAOYSA-N 4-[(1-benzyl-3-methylpyrrolidin-3-yl)-methylamino]-3-chloro-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1CC(CC1)(C)N(C1=C(C=C(C=C1)S(=O)(=O)NC=1SC=CN=1)Cl)C OFKCOGYFJSZGET-UHFFFAOYSA-N 0.000 claims description 2
DVMCAPAGTTZRQU-UHFFFAOYSA-N 4-[(1-benzyl-3-methylpyrrolidin-3-yl)amino]-3-chloro-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1CC(CC1)(C)NC1=C(C=C(C=C1)S(=O)(=O)NC=1SC=CN=1)Cl DVMCAPAGTTZRQU-UHFFFAOYSA-N 0.000 claims description 2
UGUIXQQJCIAWSG-UHFFFAOYSA-N 4-[(1-benzylpiperidin-4-yl)-methylamino]-5-chloro-2-fluoro-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C1=CC(=C(C=C1Cl)S(=O)(=O)NC=1SC=CN=1)F)C UGUIXQQJCIAWSG-UHFFFAOYSA-N 0.000 claims description 2
NTWUMXFPSJIFGL-DNVCBOLYSA-N 4-[[(2R,3R)-1-benzyl-2-methylpyrrolidin-3-yl]-methylamino]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1[C@@H]([C@@H](CC1)N(C1=CC(=C(C=C1Cl)S(=O)(=O)NC=1N=CSC=1)F)C)C NTWUMXFPSJIFGL-DNVCBOLYSA-N 0.000 claims description 2
IQAQMUYQSMWZFI-OAQYLSRUSA-N 4-[[(3R)-1-benzyl-3-methylpyrrolidin-3-yl]amino]-3-chloro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@](CC1)(C)NC1=C(C=C(C=C1)S(=O)(=O)NC=1N=CSC=1)Cl IQAQMUYQSMWZFI-OAQYLSRUSA-N 0.000 claims description 2
UCSHINHOAVARGQ-GOSISDBHSA-N 4-[[(3R)-1-benzylpyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F)C UCSHINHOAVARGQ-GOSISDBHSA-N 0.000 claims description 2
OBZZBTQNBCLIJV-MRXNPFEDSA-N 4-[[(3R)-1-benzylpyrrolidin-3-yl]-methylamino]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@@H](CC1)N(C1=CC(=C(C=C1Cl)S(=O)(=O)NC=1N=CSC=1)F)C OBZZBTQNBCLIJV-MRXNPFEDSA-N 0.000 claims description 2
RXUQULDRLQESSI-QGZVFWFLSA-N 4-[[(3R)-1-benzylpyrrolidin-3-yl]amino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@@H](CC1)NC1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F RXUQULDRLQESSI-QGZVFWFLSA-N 0.000 claims description 2
SJLWHSFIDHSHQA-MRXNPFEDSA-N 4-[[(3R)-1-benzylpyrrolidin-3-yl]amino]-3-chloro-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@@H](CC1)NC1=C(C=C(C=C1)S(=O)(=O)NC=1SC=CN=1)Cl SJLWHSFIDHSHQA-MRXNPFEDSA-N 0.000 claims description 2
PJBRISXDJULDNF-OAHLLOKOSA-N 4-[[(3R)-1-benzylpyrrolidin-3-yl]amino]-5-chloro-2-fluoro-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@@H](CC1)NC1=CC(=C(C=C1Cl)S(=O)(=O)NC=1SC=CN=1)F PJBRISXDJULDNF-OAHLLOKOSA-N 0.000 claims description 2
JJUQYLPLPQPCPI-OAHLLOKOSA-N 4-[[(3R)-1-benzylpyrrolidin-3-yl]amino]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@@H](CC1)NC1=CC(=C(C=C1Cl)S(=O)(=O)NC=1N=CSC=1)F JJUQYLPLPQPCPI-OAHLLOKOSA-N 0.000 claims description 2
TXCKAMAKLHVARQ-QRWLVFNGSA-N 4-[[(3R,4R)-1-benzyl-4-methylpyrrolidin-3-yl]amino]-3-chloro-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C[C@@H]1CN(Cc2ccccc2)C[C@@H]1Nc1ccc(cc1Cl)S(=O)(=O)Nc1nccs1 TXCKAMAKLHVARQ-QRWLVFNGSA-N 0.000 claims description 2
TXCKAMAKLHVARQ-YWZLYKJASA-N 4-[[(3R,4S)-1-benzyl-4-methylpyrrolidin-3-yl]amino]-3-chloro-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C[C@H]1CN(Cc2ccccc2)C[C@@H]1Nc1ccc(cc1Cl)S(=O)(=O)Nc1nccs1 TXCKAMAKLHVARQ-YWZLYKJASA-N 0.000 claims description 2
FHFUJRVNNSNZCQ-INIZCTEOSA-N 4-[[(3S)-1-(1,3-benzothiazol-2-ylmethyl)pyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound S1C(=NC2=C1C=CC=C2)CN1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F)C FHFUJRVNNSNZCQ-INIZCTEOSA-N 0.000 claims description 2
DDTBAVFOGFAFLC-HNNXBMFYSA-N 4-[[(3S)-1-(2,2-dimethylpropyl)pyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(C=C(C(=C1)N([C@@H]1CN(CC1)CC(C)(C)C)C)C)S(=O)(=O)NC=1N=CSC=1 DDTBAVFOGFAFLC-HNNXBMFYSA-N 0.000 claims description 2
IUGYBBOXHMNSHT-IBGZPJMESA-N 4-[[(3S)-1-(2,3-dihydro-1H-inden-2-yl)pyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C1C(CC2=CC=CC=C12)N1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F)C IUGYBBOXHMNSHT-IBGZPJMESA-N 0.000 claims description 2
SLSDNMVCDKTOOM-SFHVURJKSA-N 4-[[(3S)-1-(cyclohexylmethyl)pyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C1(CCCCC1)CN1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F)C SLSDNMVCDKTOOM-SFHVURJKSA-N 0.000 claims description 2
CGAZMXTTWBQTDZ-INIZCTEOSA-N 4-[[(3S)-1-[(1,4-dimethylimidazol-2-yl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound CN1C(=NC(=C1)C)CN1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F)C CGAZMXTTWBQTDZ-INIZCTEOSA-N 0.000 claims description 2
FMDPANUXNUXTEH-KRWDZBQOSA-N 4-[[(3S)-1-[(1,5-dimethylpyrazol-3-yl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound CN1N=C(C=C1C)CN1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F)C FMDPANUXNUXTEH-KRWDZBQOSA-N 0.000 claims description 2
IIIHYGXZQMVUJP-FQEVSTJZSA-N 4-[[(3S)-1-[(1-benzylpyrazol-4-yl)methyl]pyrrolidin-3-yl]-methylamino]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)CN1C[C@H](CC1)N(C1=CC(=C(C=C1Cl)S(=O)(=O)NC=1N=CSC=1)F)C IIIHYGXZQMVUJP-FQEVSTJZSA-N 0.000 claims description 2
VAEWPQNDVJTFSB-RXVVDRJESA-N 4-[[(3S)-1-[(1S)-2,3-dihydro-1H-inden-1-yl]pyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound CN([C@H]1CCN(C1)[C@H]1CCc2ccccc12)c1cc(F)c(cc1C)S(=O)(=O)Nc1cscn1 VAEWPQNDVJTFSB-RXVVDRJESA-N 0.000 claims description 2
KKALBNJTIFZMBP-HNNXBMFYSA-N 4-[[(3S)-1-[(2,3-difluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-2,6-difluoro-3-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(CN2C[C@H](CC2)N(C2=C(C(=C(C(=C2)F)S(=O)(=O)NC=2N=CSC=2)F)C)C)C=CC=C1F KKALBNJTIFZMBP-HNNXBMFYSA-N 0.000 claims description 2
RVAUTCOLGIFJMK-INIZCTEOSA-N 4-[[(3S)-1-[(2,3-difluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(CN2C[C@H](CC2)N(C2=CC(=C(C=C2C)S(=O)(=O)NC=2N=CSC=2)F)C)C=CC=C1F RVAUTCOLGIFJMK-INIZCTEOSA-N 0.000 claims description 2
JPGBAAWAHJVFTN-INIZCTEOSA-N 4-[[(3S)-1-[(2,5-difluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-2,6-difluoro-3-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(CN2C[C@H](CC2)N(C2=C(C(=C(C(=C2)F)S(=O)(=O)NC=2N=CSC=2)F)C)C)C=C(C=C1)F JPGBAAWAHJVFTN-INIZCTEOSA-N 0.000 claims description 2
FWBORLQLOZGSJI-KRWDZBQOSA-N 4-[[(3S)-1-[(2,5-difluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-3-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(CN2C[C@H](CC2)N(C2=C(C(=C(C=C2)S(=O)(=O)NC=2N=CSC=2)F)C)C)C=C(C=C1)F FWBORLQLOZGSJI-KRWDZBQOSA-N 0.000 claims description 2
UWGGQDPGEXYSGG-SFHVURJKSA-N 4-[[(3S)-1-[(2,5-difluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-3-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC1=C(CN2C[C@H](CC2)N(C2=C(C=C(C=C2)S(=O)(=O)NC=2N=CSC=2)C)C)C=C(C=C1)F UWGGQDPGEXYSGG-SFHVURJKSA-N 0.000 claims description 2
GZTOIWCEHLVEFC-INIZCTEOSA-N 4-[[(3S)-1-[(2,5-dimethyl-1,3-oxazol-4-yl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound CC=1OC(=C(N=1)CN1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F)C)C GZTOIWCEHLVEFC-INIZCTEOSA-N 0.000 claims description 2
MUZRKCPDAHUGSX-INIZCTEOSA-N 4-[[(3S)-1-[(4-bromophenyl)methyl]pyrrolidin-3-yl]-methylamino]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound BrC1=CC=C(CN2C[C@H](CC2)N(C2=CC(=C(C=C2Cl)S(=O)(=O)NC=2N=CSC=2)F)C)C=C1 MUZRKCPDAHUGSX-INIZCTEOSA-N 0.000 claims description 2
DNVKGIJYPXUCCW-ZDUSSCGKSA-N 4-[[(3S)-1-[(5-chloro-1,3-thiazol-2-yl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC1=CN=C(S1)CN1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F)C DNVKGIJYPXUCCW-ZDUSSCGKSA-N 0.000 claims description 2
MRCDRWKJKXYPPV-AWEZNQCLSA-N 4-[[(3S)-1-[(6-bromopyridin-2-yl)methyl]pyrrolidin-3-yl]-methylamino]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound BrC1=CC=CC(=N1)CN1C[C@H](CC1)N(C1=CC(=C(C=C1Cl)S(=O)(=O)NC=1N=CSC=1)F)C MRCDRWKJKXYPPV-AWEZNQCLSA-N 0.000 claims description 2
FOWVCVFRPKIDJL-INIZCTEOSA-N 4-[[(3S)-1-[[1-(2,2-difluoroethyl)pyrazol-3-yl]methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC(CN1N=C(C=C1)CN1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F)C)F FOWVCVFRPKIDJL-INIZCTEOSA-N 0.000 claims description 2
SVIQCPQXOGYORQ-HNNXBMFYSA-N 4-[[(3S)-1-[[1-(difluoromethyl)pyrazol-3-yl]methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC(N1N=C(C=C1)CN1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F)C)F SVIQCPQXOGYORQ-HNNXBMFYSA-N 0.000 claims description 2
RILHRNHDSBTCFP-INIZCTEOSA-N 4-[[(3S)-1-[[3-(difluoromethyl)phenyl]methyl]pyrrolidin-3-yl]-methylamino]-2,6-difluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound FC(C=1C=C(CN2C[C@H](CC2)N(C2=CC(=C(C(=C2)F)S(=O)(=O)NC=2N=CSC=2)F)C)C=CC=1)F RILHRNHDSBTCFP-INIZCTEOSA-N 0.000 claims description 2
NQVBEWCKXHTCLT-KRWDZBQOSA-N 4-[[(3S)-1-[[6-(azetidin-1-yl)pyridin-2-yl]methyl]pyrrolidin-3-yl]-methylamino]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound N1(CCC1)C1=CC=CC(=N1)CN1C[C@H](CC1)N(C1=CC(=C(C=C1Cl)S(=O)(=O)NC=1N=CSC=1)F)C NQVBEWCKXHTCLT-KRWDZBQOSA-N 0.000 claims description 2
IQAQMUYQSMWZFI-NRFANRHFSA-N 4-[[(3S)-1-benzyl-3-methylpyrrolidin-3-yl]amino]-3-chloro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@@](CC1)(C)NC1=C(C=C(C=C1)S(=O)(=O)NC=1N=CSC=1)Cl IQAQMUYQSMWZFI-NRFANRHFSA-N 0.000 claims description 2
QRMIRKQEEYSFLS-IBGZPJMESA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-ethylamino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F)CC QRMIRKQEEYSFLS-IBGZPJMESA-N 0.000 claims description 2
HQKYPRIQMLDJBN-KRWDZBQOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-ethylamino]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C=C1Cl)S(=O)(=O)NC=1N=CSC=1)F)CC HQKYPRIQMLDJBN-KRWDZBQOSA-N 0.000 claims description 2
ZFHZHCJFMMZFFD-INIZCTEOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-2,5-difluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C=C1F)S(=O)(=O)NC=1N=CSC=1)F)C ZFHZHCJFMMZFFD-INIZCTEOSA-N 0.000 claims description 2
FJOZGGJMUOMTMA-KRWDZBQOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-2,6-difluoro-3-methyl-N-(1,2-thiazol-3-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=C(C(=C(C(=C1)F)S(=O)(=O)NC1=NSC=C1)F)C)C FJOZGGJMUOMTMA-KRWDZBQOSA-N 0.000 claims description 2
ZMJGMDUEPPFODC-INIZCTEOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-2,6-difluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C(=C1)F)S(=O)(=O)NC=1N=CSC=1)F)C ZMJGMDUEPPFODC-INIZCTEOSA-N 0.000 claims description 2
CTXUKQDMHMZQRU-IBGZPJMESA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-2,6-difluoro-N-(5-fluoropyridin-2-yl)-3-methylbenzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=C(C(=C(C(=C1)F)S(=O)(=O)NC1=NC=C(C=C1)F)F)C)C CTXUKQDMHMZQRU-IBGZPJMESA-N 0.000 claims description 2
IZAGUWQJXNVBMO-SFHVURJKSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-2,6-difluoro-N-(6-fluoropyridin-2-yl)-3-methylbenzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=C(C(=C(C(=C1)F)S(=O)(=O)NC1=NC(=CC=C1)F)F)C)C IZAGUWQJXNVBMO-SFHVURJKSA-N 0.000 claims description 2
LGYWUIZBYUKVPS-IBGZPJMESA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-2-fluoro-5-methyl-N-(1,2-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC=1C=NSC=1)F)C LGYWUIZBYUKVPS-IBGZPJMESA-N 0.000 claims description 2
VZCNXUWHCLMKQD-FQEVSTJZSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-2-fluoro-N-(5-fluoropyridin-2-yl)-5-methylbenzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC1=NC=C(C=C1)F)F)C VZCNXUWHCLMKQD-FQEVSTJZSA-N 0.000 claims description 2
IKTNKGPVFJEKTJ-IBGZPJMESA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-2-fluoro-N-(6-fluoropyridin-2-yl)-5-methylbenzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C=C1C)S(=O)(=O)NC1=NC(=CC=C1)F)F)C IKTNKGPVFJEKTJ-IBGZPJMESA-N 0.000 claims description 2
KDBCNDYXFRQBOP-HNNXBMFYSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-3-chloro-2,6-difluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=C(C(=C(C(=C1)F)S(=O)(=O)NC=1N=CSC=1)F)Cl)C KDBCNDYXFRQBOP-HNNXBMFYSA-N 0.000 claims description 2
DCYXJUFCSMSKRD-INIZCTEOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-3-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=C(C(=C(C=C1)S(=O)(=O)NC=1N=CSC=1)F)Cl)C DCYXJUFCSMSKRD-INIZCTEOSA-N 0.000 claims description 2
WOVKYJCOVPVJEK-KRWDZBQOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-3-chloro-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=C(C=C(C=C1)S(=O)(=O)NC=1SC=CN=1)Cl)C WOVKYJCOVPVJEK-KRWDZBQOSA-N 0.000 claims description 2
WYYRWSBARVOUES-KRWDZBQOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-3-chloro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=C(C=C(C=C1)S(=O)(=O)NC=1N=CSC=1)Cl)C WYYRWSBARVOUES-KRWDZBQOSA-N 0.000 claims description 2
MEZWQXBTCCBWEV-IBGZPJMESA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-3-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=C(C=C(C=C1)S(=O)(=O)NC=1N=CSC=1)C)C MEZWQXBTCCBWEV-IBGZPJMESA-N 0.000 claims description 2
MATZRPGXCBCNKE-INIZCTEOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-5-(difluoromethyl)-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C=C1C(F)F)S(=O)(=O)NC=1N=CSC=1)F)C MATZRPGXCBCNKE-INIZCTEOSA-N 0.000 claims description 2
PZGPSEBKLBZHQB-INIZCTEOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-5-chloro-2-fluoro-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CN([C@H]1CCN(CC2=CC=CC=C2)C1)C1=CC(F)=C(C=C1Cl)S(=O)(=O)NC1=NC=CS1 PZGPSEBKLBZHQB-INIZCTEOSA-N 0.000 claims description 2
OBZZBTQNBCLIJV-INIZCTEOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C=C1Cl)S(=O)(=O)NC=1N=CSC=1)F)C OBZZBTQNBCLIJV-INIZCTEOSA-N 0.000 claims description 2
ZXGZMVXBTYIWOH-KRWDZBQOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-5-chloro-2-fluoro-N-(6-fluoropyridin-2-yl)benzenesulfonamide Chemical compound CN([C@H]1CCN(CC2=CC=CC=C2)C1)C1=CC(F)=C(C=C1Cl)S(=O)(=O)NC1=NC(F)=CC=C1 ZXGZMVXBTYIWOH-KRWDZBQOSA-N 0.000 claims description 2
YYZGEPVDEIZZBG-IBGZPJMESA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-5-cyclopropyl-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C=C1C1CC1)S(=O)(=O)NC=1N=CSC=1)F)C YYZGEPVDEIZZBG-IBGZPJMESA-N 0.000 claims description 2
DPHHVGVRPZESDJ-IBGZPJMESA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-5-ethyl-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=CC(=C(C=C1CC)S(=O)(=O)NC=1N=CSC=1)F)C DPHHVGVRPZESDJ-IBGZPJMESA-N 0.000 claims description 2
GMYXENXAHHYERJ-KRWDZBQOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)-3-(trifluoromethyl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)N(C1=C(C=C(C=C1)S(=O)(=O)NC=1N=CSC=1)C(F)(F)F)C GMYXENXAHHYERJ-KRWDZBQOSA-N 0.000 claims description 2
RXUQULDRLQESSI-KRWDZBQOSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]amino]-2-fluoro-5-methyl-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)NC1=CC(=C(C=C1C)S(=O)(=O)NC=1N=CSC=1)F RXUQULDRLQESSI-KRWDZBQOSA-N 0.000 claims description 2
PJBRISXDJULDNF-HNNXBMFYSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]amino]-5-chloro-2-fluoro-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)NC1=CC(=C(C=C1Cl)S(=O)(=O)NC=1SC=CN=1)F PJBRISXDJULDNF-HNNXBMFYSA-N 0.000 claims description 2
JJUQYLPLPQPCPI-HNNXBMFYSA-N 4-[[(3S)-1-benzylpyrrolidin-3-yl]amino]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)NC1=CC(=C(C=C1Cl)S(=O)(=O)NC=1N=CSC=1)F JJUQYLPLPQPCPI-HNNXBMFYSA-N 0.000 claims description 2
XLOVSKWXNKMTQF-RDJZCZTQSA-N 4-[[(3S,5S)-1-benzyl-5-methylpyrrolidin-3-yl]-methylamino]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](C[C@@H]1C)N(C1=CC(=C(C=C1Cl)S(=O)(=O)NC=1N=CSC=1)F)C XLOVSKWXNKMTQF-RDJZCZTQSA-N 0.000 claims description 2
LHZHIYDDDPRCSX-OAQYLSRUSA-N 4-[[(7S)-5-benzyl-5-azaspiro[2.4]heptan-7-yl]-methylamino]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1CC2(CC2)[C@@H](C1)N(C1=CC(=C(C=C1Cl)S(=O)(=O)NC=1N=CSC=1)F)C LHZHIYDDDPRCSX-OAQYLSRUSA-N 0.000 claims description 2
LMOGPJUZSPUOKM-HXUWFJFHSA-N 4-[[(7S)-5-benzyl-5-azaspiro[2.4]heptan-7-yl]amino]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1CC2(CC2)[C@@H](C1)NC1=CC(=C(C=C1Cl)S(=O)(=O)NC=1N=CSC=1)F LMOGPJUZSPUOKM-HXUWFJFHSA-N 0.000 claims description 2
SNOOPGKUOHRVSG-MRXNPFEDSA-N 5-chloro-2-fluoro-4-[[(3R)-1-[(3-methylphenyl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1SC=CN=1)F)N[C@H]1CN(CC1)CC1=CC(=CC=C1)C SNOOPGKUOHRVSG-MRXNPFEDSA-N 0.000 claims description 2
BPFRUDPKDVUBOF-INIZCTEOSA-N 5-chloro-2-fluoro-4-[[(3S)-1-(imidazo[1,5-a]pyridin-3-ylmethyl)pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=NC=C2N1C=CC=C2 BPFRUDPKDVUBOF-INIZCTEOSA-N 0.000 claims description 2
NBQKVGHOLPCTDK-SFHVURJKSA-N 5-chloro-2-fluoro-4-[[(3S)-1-(isoquinolin-8-ylmethyl)pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC=1C=CC=C2C=CN=CC=12 NBQKVGHOLPCTDK-SFHVURJKSA-N 0.000 claims description 2
CLZBPBUBFIGQIV-INIZCTEOSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(2-fluoro-3-methylphenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C(=CC=C1)C)F CLZBPBUBFIGQIV-INIZCTEOSA-N 0.000 claims description 2
RDTBQHQBCOIDTI-INIZCTEOSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(2-fluoro-4-methylphenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C=C(C=C1)C)F RDTBQHQBCOIDTI-INIZCTEOSA-N 0.000 claims description 2
UUPGUIFCQKWUEW-HNNXBMFYSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(2-fluoro-5-methoxyphenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C=CC(=C1)OC)F UUPGUIFCQKWUEW-HNNXBMFYSA-N 0.000 claims description 2
QOSKDPPDQQRPMV-INIZCTEOSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(2-fluoro-5-methylphenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C=CC(=C1)C)F QOSKDPPDQQRPMV-INIZCTEOSA-N 0.000 claims description 2
XIHHQADCVGDUNT-HNNXBMFYSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(2-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C=CC=C1)F XIHHQADCVGDUNT-HNNXBMFYSA-N 0.000 claims description 2
OMESNTXOELFXRP-HNNXBMFYSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(2-hydroxyphenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C=CC=C1)O OMESNTXOELFXRP-HNNXBMFYSA-N 0.000 claims description 2
PZUYBZPEGAJTNT-INIZCTEOSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(2-methoxyphenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C=CC=C1)OC PZUYBZPEGAJTNT-INIZCTEOSA-N 0.000 claims description 2
YANIPGMLUWWQDS-INIZCTEOSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(3-fluoro-2-methylphenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C(=CC=C1)F)C YANIPGMLUWWQDS-INIZCTEOSA-N 0.000 claims description 2
YLUTWCUFBMBBBY-AWEZNQCLSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(3-fluoro-6-methylpyridin-2-yl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=NC(=CC=C1F)C YLUTWCUFBMBBBY-AWEZNQCLSA-N 0.000 claims description 2
SHZMIHNXYGWYLK-INIZCTEOSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(3-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=CC(=CC=C1)F SHZMIHNXYGWYLK-INIZCTEOSA-N 0.000 claims description 2
UDWMPKWABASNAD-INIZCTEOSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(3-methoxyphenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=CC(=CC=C1)OC UDWMPKWABASNAD-INIZCTEOSA-N 0.000 claims description 2
SNOOPGKUOHRVSG-INIZCTEOSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(3-methylphenyl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1SC=CN=1)F)N[C@@H]1CN(CC1)CC1=CC(=CC=C1)C SNOOPGKUOHRVSG-INIZCTEOSA-N 0.000 claims description 2
VPOQXTCOBGLEAA-INIZCTEOSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(4-fluoro-3-methylphenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=CC(=C(C=C1)F)C VPOQXTCOBGLEAA-INIZCTEOSA-N 0.000 claims description 2
CCTRUTPPSZQGLF-INIZCTEOSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(4-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=CC=C(C=C1)F CCTRUTPPSZQGLF-INIZCTEOSA-N 0.000 claims description 2
SYIMLQDKCUQRPH-HNNXBMFYSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[(6-methoxypyridin-2-yl)methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=NC(=CC=C1)OC SYIMLQDKCUQRPH-HNNXBMFYSA-N 0.000 claims description 2
BJGCCYNZXROEED-SFHVURJKSA-N 5-chloro-2-fluoro-4-[[(3S)-1-[[3-(2-hydroxypropan-2-yl)phenyl]methyl]pyrrolidin-3-yl]-methylamino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=CC(=CC=C1)C(C)(C)O BJGCCYNZXROEED-SFHVURJKSA-N 0.000 claims description 2
BLSMPPXXTCCKRU-KRWDZBQOSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-(1-phenylcyclopropyl)pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)C1(CC1)C1=CC=CC=C1)C BLSMPPXXTCCKRU-KRWDZBQOSA-N 0.000 claims description 2
HBGSYDPAKUXTJO-KRWDZBQOSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-(2-phenylpropan-2-yl)pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)C(C)(C)C1=CC=CC=C1)C HBGSYDPAKUXTJO-KRWDZBQOSA-N 0.000 claims description 2
SQPBPXFPQWHESU-SFHVURJKSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-(3-phenylpropyl)pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)CCCC1=CC=CC=C1)C SQPBPXFPQWHESU-SFHVURJKSA-N 0.000 claims description 2
UUKZMQSEPVUSJZ-SFHVURJKSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-(quinolin-8-ylmethyl)pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)CC=1C=CC=C2C=CC=NC=12)C UUKZMQSEPVUSJZ-SFHVURJKSA-N 0.000 claims description 2
DDDSFCBWEZZPCQ-ZDUSSCGKSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-(thiophen-2-ylmethyl)pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)CC=1SC=CC=1)C DDDSFCBWEZZPCQ-ZDUSSCGKSA-N 0.000 claims description 2
IQNVVVSWODANTN-FXAWDEMLSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-[(1R)-1-phenylpropyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)[C@H](CC)C1=CC=CC=C1)C IQNVVVSWODANTN-FXAWDEMLSA-N 0.000 claims description 2
IQNVVVSWODANTN-PXNSSMCTSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-[(1S)-1-phenylpropyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)[C@@H](CC)C1=CC=CC=C1)C IQNVVVSWODANTN-PXNSSMCTSA-N 0.000 claims description 2
SAPQTCFORWDHMP-KRWDZBQOSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-[(2-methylphenyl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)CC1=C(C=CC=C1)C)C SAPQTCFORWDHMP-KRWDZBQOSA-N 0.000 claims description 2
NZJVRPUXGKRILH-SFHVURJKSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-[(3-propan-2-yloxyphenyl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=CC(=CC=C1)OC(C)C NZJVRPUXGKRILH-SFHVURJKSA-N 0.000 claims description 2
DHTLOPUCXDTVQU-KRWDZBQOSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-[(4-methylphenyl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)CC1=CC=C(C=C1)C)C DHTLOPUCXDTVQU-KRWDZBQOSA-N 0.000 claims description 2
IPLWZCIMJXRMAM-INIZCTEOSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-[(4-methylpyridin-2-yl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)CC1=NC=CC(=C1)C)C IPLWZCIMJXRMAM-INIZCTEOSA-N 0.000 claims description 2
HHNFXOYVWYCPDX-IBGZPJMESA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-[(4-propylphenyl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)CC1=CC=C(C=C1)CCC)C HHNFXOYVWYCPDX-IBGZPJMESA-N 0.000 claims description 2
CLPKNZQVQSGSCX-AWEZNQCLSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-[(5-methylfuran-2-yl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)CC=1OC(=CC=1)C)C CLPKNZQVQSGSCX-AWEZNQCLSA-N 0.000 claims description 2
NTSLOBXTZTWOPH-INIZCTEOSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-[(6-methylpyridin-2-yl)methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)CC1=NC(=CC=C1)C)C NTSLOBXTZTWOPH-INIZCTEOSA-N 0.000 claims description 2
OTONOMQCZOPDOY-AWEZNQCLSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-[[2-(trifluoromethyl)pyridin-4-yl]methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)CC1=CC(=NC=C1)C(F)(F)F)C OTONOMQCZOPDOY-AWEZNQCLSA-N 0.000 claims description 2
BSMGQIYCOMFQNZ-INIZCTEOSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-[[3-(trifluoromethyl)phenyl]methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)CC1=CC(=CC=C1)C(F)(F)F)C BSMGQIYCOMFQNZ-INIZCTEOSA-N 0.000 claims description 2
RMBMVMBQHSMKOF-LBPRGKRZSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-[[5-(trifluoromethyl)furan-2-yl]methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)CC=1OC(=CC=1)C(F)(F)F)C RMBMVMBQHSMKOF-LBPRGKRZSA-N 0.000 claims description 2
JMHGXOHDGTTXAT-AWEZNQCLSA-N 5-chloro-2-fluoro-4-[methyl-[(3S)-1-[[6-(trifluoromethyl)pyridin-2-yl]methyl]pyrrolidin-3-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)CC1=NC(=CC=C1)C(F)(F)F)C JMHGXOHDGTTXAT-AWEZNQCLSA-N 0.000 claims description 2
JYADRIHNWKOINM-MRXNPFEDSA-N 5-chloro-2-fluoro-4-[methyl-[1-[(1R)-1-phenylethyl]piperidin-4-yl]amino]-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C1CCN(CC1)[C@H](C)C1=CC=CC=C1)C JYADRIHNWKOINM-MRXNPFEDSA-N 0.000 claims description 2
FTUXQVYJPOZFNP-KRWDZBQOSA-N 5-chloro-4-[[(3S)-1-(2,3-dihydro-1H-inden-2-yl)pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)C1CC2=CC=CC=C2C1 FTUXQVYJPOZFNP-KRWDZBQOSA-N 0.000 claims description 2
BMNWDZOAQMVATD-AWEZNQCLSA-N 5-chloro-4-[[(3S)-1-(3,3-dimethylbutyl)pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CCC(C)(C)C BMNWDZOAQMVATD-AWEZNQCLSA-N 0.000 claims description 2
LHOQAADZGRIBMK-OXJNMPFZSA-N 5-chloro-4-[[(3S)-1-[(1R)-2,3-dihydro-1H-inden-1-yl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)[C@@H]1CCC2=CC=CC=C12 LHOQAADZGRIBMK-OXJNMPFZSA-N 0.000 claims description 2
LHOQAADZGRIBMK-JXFKEZNVSA-N 5-chloro-4-[[(3S)-1-[(1S)-2,3-dihydro-1H-inden-1-yl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)[C@H]1CCC2=CC=CC=C12 LHOQAADZGRIBMK-JXFKEZNVSA-N 0.000 claims description 2
HESWTPVDKFBBCO-AWEZNQCLSA-N 5-chloro-4-[[(3S)-1-[(2,3-difluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C(=CC=C1)F)F HESWTPVDKFBBCO-AWEZNQCLSA-N 0.000 claims description 2
KMNQFCVFMZDVCH-HNNXBMFYSA-N 5-chloro-4-[[(3S)-1-[(2,5-dichlorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C=CC(=C1)Cl)Cl KMNQFCVFMZDVCH-HNNXBMFYSA-N 0.000 claims description 2
HRMDNDZYDZKELN-HNNXBMFYSA-N 5-chloro-4-[[(3S)-1-[(2,5-difluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C=CC(=C1)F)F HRMDNDZYDZKELN-HNNXBMFYSA-N 0.000 claims description 2
IVRZNRGAQNJENU-KRWDZBQOSA-N 5-chloro-4-[[(3S)-1-[(2,6-dimethylphenyl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C=CC=C1C)C IVRZNRGAQNJENU-KRWDZBQOSA-N 0.000 claims description 2
WLGFYDUWRLQYDJ-ZDUSSCGKSA-N 5-chloro-4-[[(3S)-1-[(2-chloro-6-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C=CC=C1F)Cl WLGFYDUWRLQYDJ-ZDUSSCGKSA-N 0.000 claims description 2
RAOPNLNVMWUTID-HNNXBMFYSA-N 5-chloro-4-[[(3S)-1-[(2-chlorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C=CC=C1)Cl RAOPNLNVMWUTID-HNNXBMFYSA-N 0.000 claims description 2
IDQPLGVWRVONLP-AWEZNQCLSA-N 5-chloro-4-[[(3S)-1-[(3-chloro-2-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C(=CC=C1)Cl)F IDQPLGVWRVONLP-AWEZNQCLSA-N 0.000 claims description 2
KCCRUOWFWBICPA-INIZCTEOSA-N 5-chloro-4-[[(3S)-1-[(3-chlorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=CC(=CC=C1)Cl KCCRUOWFWBICPA-INIZCTEOSA-N 0.000 claims description 2
FWSYYXGCYCAYFJ-INIZCTEOSA-N 5-chloro-4-[[(3S)-1-[(4-chlorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=CC=C(C=C1)Cl FWSYYXGCYCAYFJ-INIZCTEOSA-N 0.000 claims description 2
BBGOVXSDBDNLPD-HNNXBMFYSA-N 5-chloro-4-[[(3S)-1-[(5-chloro-2-fluorophenyl)methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=C(C=CC(=C1)Cl)F BBGOVXSDBDNLPD-HNNXBMFYSA-N 0.000 claims description 2
FVEJKXNAWWCHPA-LBPRGKRZSA-N 5-chloro-4-[[(3S)-1-[[6-(difluoromethyl)-3-fluoropyridin-2-yl]methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=NC(=CC=C1F)C(F)F FVEJKXNAWWCHPA-LBPRGKRZSA-N 0.000 claims description 2
STRHWFHTELGFDG-AWEZNQCLSA-N 5-chloro-4-[[(3S)-1-[[6-(difluoromethyl)pyridin-2-yl]methyl]pyrrolidin-3-yl]-methylamino]-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N(C)[C@@H]1CN(CC1)CC1=NC(=CC=C1)C(F)F STRHWFHTELGFDG-AWEZNQCLSA-N 0.000 claims description 2
NWBFWFRORVSRPE-LWKPJOBUSA-N ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)C(C)C1=CC=CC=C1)C Chemical compound ClC=1C(=CC(=C(C=1)S(=O)(=O)NC=1N=CSC=1)F)N([C@@H]1CN(CC1)C(C)C1=CC=CC=C1)C NWBFWFRORVSRPE-LWKPJOBUSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims 18
125000006647 (C3-C15) cycloalkyl group Chemical group 0.000 claims 14
125000000753 cycloalkyl group Chemical group 0.000 claims 8
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 6
125000000262 haloalkenyl group Chemical group 0.000 claims 5
GZHKVFVRCKFOOD-UHFFFAOYSA-N 2-(1,3-thiazol-4-yl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1C1=CSC=N1 GZHKVFVRCKFOOD-UHFFFAOYSA-N 0.000 claims 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
125000001424 substituent group Chemical group 0.000 claims 4
125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 3
125000004043 oxo group Chemical group O=* 0.000 claims 2
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 1
239000000651 prodrug Substances 0.000 description 16
229940002612 prodrug Drugs 0.000 description 16
238000000034 method Methods 0.000 description 10
102000016913 Voltage-Gated Sodium Channels Human genes 0.000 description 6
108010053752 Voltage-Gated Sodium Channels Proteins 0.000 description 6
OSDHPDPYMSJEJW-UHFFFAOYSA-N 3-chloro-4-[1-[(2-fluorophenyl)methyl]-3-methylpiperidin-4-yl]oxy-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1OC1C(CN(CC1)CC1=C(C=CC=C1)F)C)S(=O)(=O)NC=1SC=CN=1 OSDHPDPYMSJEJW-UHFFFAOYSA-N 0.000 description 2
OWBNMAYPQVINOE-UHFFFAOYSA-N 3-chloro-4-[3-methyl-1-[(3-methylphenyl)methyl]piperidin-4-yl]oxy-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1OC1C(CN(CC1)CC1=CC(=CC=C1)C)C)S(=O)(=O)NC=1SC=CN=1 OWBNMAYPQVINOE-UHFFFAOYSA-N 0.000 description 2
NWDBYOZTIDJAKC-UHFFFAOYSA-N 4-(1-benzyl-3-methylpiperidin-4-yl)oxy-3-chloro-N-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C(C1=CC=CC=C1)N1CC(C(CC1)OC1=C(C=C(C=C1)S(=O)(=O)NC=1SC=CN=1)Cl)C NWDBYOZTIDJAKC-UHFFFAOYSA-N 0.000 description 2
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JP2018560884A 2016-05-20 2017-05-19 ベンゼンスルホンアミド化合物および治療剤としてのそれらの使用 Active JP6938545B2 (ja)