JP2019519484A5 - - Google Patents
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- Publication number
- JP2019519484A5 JP2019519484A5 JP2018557818A JP2018557818A JP2019519484A5 JP 2019519484 A5 JP2019519484 A5 JP 2019519484A5 JP 2018557818 A JP2018557818 A JP 2018557818A JP 2018557818 A JP2018557818 A JP 2018557818A JP 2019519484 A5 JP2019519484 A5 JP 2019519484A5
- Authority
- JP
- Japan
- Prior art keywords
- acetamide
- pyrazol
- sulfamoylphenyl
- chlorophenyl
- phenyl
- Prior art date
- 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.)
- Granted
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- -1 methylenedioxy group Chemical group 0.000 claims 229
- 229910052739 hydrogen Inorganic materials 0.000 claims 45
- 239000001257 hydrogen Substances 0.000 claims 45
- 229910052736 halogen Inorganic materials 0.000 claims 39
- 150000002367 halogens Chemical group 0.000 claims 36
- 150000002431 hydrogen Chemical group 0.000 claims 32
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 27
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 25
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 21
- 208000002193 Pain Diseases 0.000 claims 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- 230000036407 pain Effects 0.000 claims 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 201000010099 disease Diseases 0.000 claims 10
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 9
- 125000001153 fluoro group Chemical group F* 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 8
- 201000009273 Endometriosis Diseases 0.000 claims 7
- 150000001204 N-oxides Chemical class 0.000 claims 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 6
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 208000024891 symptom Diseases 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 3
- 208000005171 Dysmenorrhea Diseases 0.000 claims 3
- 206010013935 Dysmenorrhoea Diseases 0.000 claims 3
- 208000004483 Dyspareunia Diseases 0.000 claims 3
- 206010020751 Hypersensitivity Diseases 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 208000026935 allergic disease Diseases 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 230000002496 gastric effect Effects 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- NKFLEFWUYAUDJV-UHFFFAOYSA-N pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1 NKFLEFWUYAUDJV-UHFFFAOYSA-N 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- CBVBUDSEEGXIRC-HOTGVXAUSA-N 2-(2-chlorophenyl)-N-[4-[4-[(2S,5S)-2,5-dimethylpyrrolidin-1-yl]pyrazol-1-yl]-3-sulfamoylphenyl]acetamide Chemical compound C[C@H]1CC[C@H](C)N1c1cnn(c1)-c1ccc(NC(=O)Cc2ccccc2Cl)cc1S(N)(=O)=O CBVBUDSEEGXIRC-HOTGVXAUSA-N 0.000 claims 2
- NEURYOYRKPFLKH-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=C(N=C=O)C(Cl)=C1 NEURYOYRKPFLKH-UHFFFAOYSA-N 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 206010065390 Inflammatory pain Diseases 0.000 claims 2
- 208000008930 Low Back Pain Diseases 0.000 claims 2
- MKJMGCGGPAJFCB-UHFFFAOYSA-N N-[4-bromo-3-(dimethylaminomethylideneamino)sulfonylphenyl]-2-(2-chlorophenyl)acetamide Chemical compound BrC1=C(C=C(C=C1)NC(CC1=C(C=CC=C1)Cl)=O)S(N=CN(C)C)(=O)=O MKJMGCGGPAJFCB-UHFFFAOYSA-N 0.000 claims 2
- 208000000450 Pelvic Pain Diseases 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 230000013872 defecation Effects 0.000 claims 2
- 206010013990 dysuria Diseases 0.000 claims 2
- 230000004761 fibrosis Effects 0.000 claims 2
- 230000003176 fibrotic effect Effects 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 230000009610 hypersensitivity Effects 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- WRFOJGXVZQHQRF-UHFFFAOYSA-N 1-[2-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-nitrophenyl]pyrazole-4-carboxylic acid Chemical compound COC1=C(CNS(=O)(=O)C2=C(C=CC(=C2)[N+](=O)[O-])N2N=CC(=C2)C(=O)O)C=CC(=C1)OC WRFOJGXVZQHQRF-UHFFFAOYSA-N 0.000 claims 1
- YXJYVKZMIASXAG-UHFFFAOYSA-N 1-[4-[[2-(2-chlorophenyl)acetyl]amino]-2-sulfamoylphenyl]-N-cyclopropyl-N-methylpyrazole-4-carboxamide Chemical compound CN(C1CC1)C(=O)c1cnn(c1)-c1ccc(NC(=O)Cc2ccccc2Cl)cc1S(N)(=O)=O YXJYVKZMIASXAG-UHFFFAOYSA-N 0.000 claims 1
- UUBYQHPZHKFMTG-UHFFFAOYSA-N 2-(2-bromophenyl)-N-[3-sulfamoyl-4-[5-(trifluoromethyl)pyridin-3-yl]phenyl]acetamide 2-(2,4-difluorophenyl)-N-[3-sulfamoyl-4-[5-(trifluoromethyl)pyridin-3-yl]phenyl]acetamide Chemical compound FC1=C(C=CC(=C1)F)CC(=O)NC1=CC(=C(C=C1)C=1C=NC=C(C1)C(F)(F)F)S(N)(=O)=O.BrC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)C=1C=NC=C(C1)C(F)(F)F)S(N)(=O)=O UUBYQHPZHKFMTG-UHFFFAOYSA-N 0.000 claims 1
- WFWOKUIHMRBMMC-UHFFFAOYSA-N 2-(2-chloro-3,6-difluorophenyl)-N-[3-sulfamoyl-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound ClC1=C(C(=CC=C1F)F)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C(F)(F)F)S(N)(=O)=O WFWOKUIHMRBMMC-UHFFFAOYSA-N 0.000 claims 1
- HECFUHGLZHWEBY-UHFFFAOYSA-N 2-(2-chloro-4,5-difluorophenyl)-N-[3-sulfamoyl-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound ClC1=C(C=C(C(=C1)F)F)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C(F)(F)F)S(N)(=O)=O HECFUHGLZHWEBY-UHFFFAOYSA-N 0.000 claims 1
- DWWXZBCXDPIIEW-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-N-[3-sulfamoyl-4-[3-(trifluoromethyl)-1,2,4-triazol-1-yl]phenyl]acetamide Chemical compound ClC1=C(C=CC(=C1)F)CC(=O)NC1=CC(=C(C=C1)N1N=C(N=C1)C(F)(F)F)S(N)(=O)=O DWWXZBCXDPIIEW-UHFFFAOYSA-N 0.000 claims 1
- AXJHRVLFGPAXBK-UHFFFAOYSA-N 2-(2-chloro-5-fluorophenyl)-N-[3-sulfamoyl-4-[3-(trifluoromethyl)-1,2,4-triazol-1-yl]phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2cc(F)ccc2Cl)ccc1-n1cnc(n1)C(F)(F)F AXJHRVLFGPAXBK-UHFFFAOYSA-N 0.000 claims 1
- OTLVSNJUJOOHPB-UHFFFAOYSA-N 2-(2-chloro-5-fluorophenyl)-N-[4-[1-(difluoromethyl)pyrazol-4-yl]-3-sulfamoylphenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2cc(F)ccc2Cl)ccc1-c1cnn(c1)C(F)F OTLVSNJUJOOHPB-UHFFFAOYSA-N 0.000 claims 1
- RYHZLLODHLOTKS-UHFFFAOYSA-N 2-(2-chloro-5-methylphenyl)-N-[3-sulfamoyl-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound ClC1=C(C=C(C=C1)C)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C(F)(F)F)S(N)(=O)=O RYHZLLODHLOTKS-UHFFFAOYSA-N 0.000 claims 1
- GXTOAJYKJQVLRS-UHFFFAOYSA-N 2-(2-chloro-6-fluoro-3-methylphenyl)-N-[3-sulfamoyl-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound ClC1=C(C(=CC=C1C)F)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C(F)(F)F)S(N)(=O)=O GXTOAJYKJQVLRS-UHFFFAOYSA-N 0.000 claims 1
- VUBLKOPPIWFMFK-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-N-[3-sulfamoyl-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide 2-(2-methoxyphenyl)-N-[3-sulfamoyl-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound ClC1=C(C(=CC=C1)F)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C(F)(F)F)S(N)(=O)=O.COC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C(F)(F)F)S(N)(=O)=O VUBLKOPPIWFMFK-UHFFFAOYSA-N 0.000 claims 1
- LIMPZMGFKMXMJK-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-N-[4-(6-chloropyridin-3-yl)-3-sulfamoylphenyl]acetamide N-[4-(6-chloropyridin-3-yl)-3-sulfamoylphenyl]-2-[4-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C(C=N1)C1=C(C=C(C=C1)NC(CC1=CC=C(C=C1)C(F)(F)F)=O)S(N)(=O)=O.ClC1=C(C(=CC=C1)F)CC(=O)NC1=CC(=C(C=C1)C=1C=NC(=CC1)Cl)S(N)(=O)=O LIMPZMGFKMXMJK-UHFFFAOYSA-N 0.000 claims 1
- IRLXVYHKRZXIME-UHFFFAOYSA-N 2-(2-chloro-6-methoxyphenyl)-N-[3-sulfamoyl-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound ClC1=C(C(=CC=C1)OC)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C(F)(F)F)S(N)(=O)=O IRLXVYHKRZXIME-UHFFFAOYSA-N 0.000 claims 1
- RRBGMAAPGQFCFU-UHFFFAOYSA-N 2-(2-chlorophenyl)-2,2-difluoro-N-[3-sulfamoyl-4-[3-(trifluoromethyl)-1,2,4-triazol-1-yl]phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)C(F)(F)c2ccccc2Cl)ccc1-n1cnc(n1)C(F)(F)F RRBGMAAPGQFCFU-UHFFFAOYSA-N 0.000 claims 1
- VAHUDOHTZQAQBR-UHFFFAOYSA-N 2-(2-chlorophenyl)-2-hydroxy-N-[3-sulfamoyl-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)C(O)c2ccccc2Cl)ccc1-n1cc(cn1)C(F)(F)F VAHUDOHTZQAQBR-UHFFFAOYSA-N 0.000 claims 1
- JNONWZWBKPDTKL-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-(dimethylaminomethylideneamino)sulfonyl-4-(1-methylpyrrol-3-yl)phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)C1=CN(C=C1)C)S(N=CN(C)C)(=O)=O JNONWZWBKPDTKL-UHFFFAOYSA-N 0.000 claims 1
- PALDDDCDUCGIIK-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-(dimethylaminomethylideneamino)sulfonyl-4-(1H-pyrazol-4-yl)phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)C=1C=NNC=1)S(N=CN(C)C)(=O)=O PALDDDCDUCGIIK-UHFFFAOYSA-N 0.000 claims 1
- KAPVKSYSBOIXJZ-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-(dimethylaminomethylideneamino)sulfonyl-4-(4-fluoropyrazol-1-yl)phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)F)S(N=CN(C)C)(=O)=O KAPVKSYSBOIXJZ-UHFFFAOYSA-N 0.000 claims 1
- RKIWJHBFPPFMEF-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-(dimethylaminomethylideneamino)sulfonyl-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C(F)(F)F)S(N=CN(C)C)(=O)=O RKIWJHBFPPFMEF-UHFFFAOYSA-N 0.000 claims 1
- AGMBSMPRGQFESB-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-(3-fluoropyrazol-1-yl)phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=C(C=C1)F)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O AGMBSMPRGQFESB-UHFFFAOYSA-N 0.000 claims 1
- NUIRIRYFAWADKY-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-(4-methylimidazol-1-yl)phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1C=NC(=C1)C)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O NUIRIRYFAWADKY-UHFFFAOYSA-N 0.000 claims 1
- WXXOJGGADMTRMS-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-(4-methylpyrazol-1-yl)phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O WXXOJGGADMTRMS-UHFFFAOYSA-N 0.000 claims 1
- VWBUZNWFISPPHO-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-(4-propan-2-ylpyrazol-1-yl)phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C(C)C)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O VWBUZNWFISPPHO-UHFFFAOYSA-N 0.000 claims 1
- ZJHAFSKUIBONBG-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-[4-(2,2,2-trifluoroethylamino)pyrazol-1-yl]phenyl]acetamide Chemical compound COc1ccc(CNS(=O)(=O)c2cc(NC(=O)Cc3ccccc3Cl)ccc2-n2cc(NCC(F)(F)F)cn2)c(OC)c1 ZJHAFSKUIBONBG-UHFFFAOYSA-N 0.000 claims 1
- CEOCTVPKOXCATN-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-[4-(2,5-dimethylpyrrolidin-1-yl)pyrazol-1-yl]phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)N1C(CCC1C)C)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O CEOCTVPKOXCATN-UHFFFAOYSA-N 0.000 claims 1
- QFWFVJRZFFZIAD-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-[4-(2-methoxyethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)CCOC)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O QFWFVJRZFFZIAD-UHFFFAOYSA-N 0.000 claims 1
- JZMWQTDDRRQFJK-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-pyrazolo[3,4-b]pyridin-2-ylphenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=C2N=CC=CC2=C1)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O JZMWQTDDRRQFJK-UHFFFAOYSA-N 0.000 claims 1
- WSVFQMHOJQDNHU-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-pyrazolo[3,4-c]pyridin-2-ylphenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=C2C=NC=CC2=C1)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O WSVFQMHOJQDNHU-UHFFFAOYSA-N 0.000 claims 1
- ARTKRNWQJIEISO-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-pyrazolo[4,3-b]pyridin-2-ylphenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=C2C(N=CC=C2)=C1)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O ARTKRNWQJIEISO-UHFFFAOYSA-N 0.000 claims 1
- JUTVSOMZGLRXHQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-sulfamoyl-2-(trifluoromethyl)-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound NS(=O)(=O)c1c(ccc(NC(=O)Cc2ccccc2Cl)c1C(F)(F)F)-n1cc(cn1)C(F)(F)F JUTVSOMZGLRXHQ-UHFFFAOYSA-N 0.000 claims 1
- GFFKSVRSKNJISM-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[3-sulfamoyl-4-[3-(trifluoromethyl)-1,2,4-triazol-1-yl]phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2ccccc2Cl)ccc1-n1cnc(n1)C(F)(F)F GFFKSVRSKNJISM-UHFFFAOYSA-N 0.000 claims 1
- QATOWVCRISSBKW-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-(2-methoxy-1,3-thiazol-4-yl)-3-sulfamoylphenyl]acetamide Chemical compound COc1nc(cs1)-c1ccc(NC(=O)Cc2ccccc2Cl)cc1S(N)(=O)=O QATOWVCRISSBKW-UHFFFAOYSA-N 0.000 claims 1
- DLPOODQABXLEGI-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-(3-cyclopropylpyrazol-1-yl)-3-[(2,4-dimethoxyphenyl)methylsulfamoyl]phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=C(C=C1)C1CC1)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O DLPOODQABXLEGI-UHFFFAOYSA-N 0.000 claims 1
- VGQJTRFBPVRRJK-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-(4-cyano-1,3-thiazol-2-yl)-3-sulfamoylphenyl]acetamide 2-(2-chlorophenyl)-N-[4-[2-(difluoromethyl)-1,3-thiazol-5-yl]-3-sulfamoylphenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)C1=CN=C(S1)C(F)F)S(N)(=O)=O.ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)C=1SC=C(N1)C#N)S(N)(=O)=O VGQJTRFBPVRRJK-UHFFFAOYSA-N 0.000 claims 1
- UMUFLWJJAWFMLD-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-(4-cyanopyrazol-1-yl)-3-sulfamoyl-2-(trifluoromethyl)phenyl]acetamide Chemical compound NS(=O)(=O)c1c(ccc(NC(=O)Cc2ccccc2Cl)c1C(F)(F)F)-n1cc(cn1)C#N UMUFLWJJAWFMLD-UHFFFAOYSA-N 0.000 claims 1
- VLGCAGJBFFVXAV-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-(4-cyanopyrazol-1-yl)-3-sulfamoylphenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C#N)S(N)(=O)=O VLGCAGJBFFVXAV-UHFFFAOYSA-N 0.000 claims 1
- OIOJUHGSQNSGQC-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-(4-cyanopyrazol-1-yl)-5-sulfamoyl-2-(trifluoromethyl)phenyl]acetamide 2-(2-chlorophenyl)-N-[3-sulfamoyl-4-[2-(trifluoromethyl)-1,3-thiazol-5-yl]phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=C(C=C(C(=C1)S(N)(=O)=O)N1N=CC(=C1)C#N)C(F)(F)F.ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)C1=CN=C(S1)C(F)(F)F)S(N)(=O)=O OIOJUHGSQNSGQC-UHFFFAOYSA-N 0.000 claims 1
- PYFFLIYKHFVRHQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-(4-cyclopropylimidazol-1-yl)-3-[(2,4-dimethoxyphenyl)methylsulfamoyl]phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1C=NC(=C1)C1CC1)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O PYFFLIYKHFVRHQ-UHFFFAOYSA-N 0.000 claims 1
- FGDPMFCYEFTFOU-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-(4-methyl-1,3-oxazol-2-yl)-3-sulfamoylphenyl]acetamide 2-(2-chlorophenyl)-N-[3-sulfamoyl-4-[2-(trifluoromethyl)-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)C=1N=C(SC1)C(F)(F)F)S(N)(=O)=O.ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)C=1OC=C(N1)C)S(N)(=O)=O FGDPMFCYEFTFOU-UHFFFAOYSA-N 0.000 claims 1
- QMJCWWFHHFSGBY-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-(5-chloropyridin-2-yl)-3-sulfamoylphenyl]acetamide 2-(2-chlorophenyl)-N-[4-(1,2-dimethylimidazol-4-yl)-3-sulfamoylphenyl]acetamide Chemical compound CC1=NC(=CN1C)C2=C(C=C(C=C2)NC(=O)CC3=CC=CC=C3Cl)S(=O)(=O)N.C1=CC=C(C(=C1)CC(=O)NC2=CC(=C(C=C2)C3=NC=C(C=C3)Cl)S(=O)(=O)N)Cl QMJCWWFHHFSGBY-UHFFFAOYSA-N 0.000 claims 1
- DEBYNMZGKRFJFD-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-(5-cyano-1-methylpyrrol-2-yl)-3-(dimethylaminomethylideneamino)sulfonylphenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)C=1N(C(=CC=1)C#N)C)S(N=CN(C)C)(=O)=O DEBYNMZGKRFJFD-UHFFFAOYSA-N 0.000 claims 1
- MHGYTJHQOUNZDM-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-3-sulfamoylphenyl]acetamide N-[4-[4-(difluoromethyl)pyrazol-1-yl]-3-sulfamoylphenyl]-2-(2-fluorophenyl)acetamide Chemical compound FC(C=1C=NN(C1)C1=C(C=C(C=C1)NC(CC1=C(C=CC=C1)F)=O)S(N)(=O)=O)F.ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)C=1OC(=NN1)C1CC1)S(N)(=O)=O MHGYTJHQOUNZDM-UHFFFAOYSA-N 0.000 claims 1
- CETKNPSQOTULQP-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-[1-(3-hydroxy-3-methylbutyl)pyrazol-4-yl]-3-sulfamoylphenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)C=1C=NN(C=1)CCC(C)(C)O)S(N)(=O)=O CETKNPSQOTULQP-UHFFFAOYSA-N 0.000 claims 1
- JVFXOPGUOCLKLO-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-[1-(difluoromethyl)-5-(trifluoromethyl)pyrazol-4-yl]-3-sulfamoylphenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2ccccc2Cl)ccc1-c1cnn(C(F)F)c1C(F)(F)F JVFXOPGUOCLKLO-UHFFFAOYSA-N 0.000 claims 1
- KVMJKCFVZLPEBO-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-[1-(difluoromethyl)pyrazol-4-yl]-3-sulfamoyl-2-(trifluoromethyl)phenyl]acetamide Chemical compound NS(=O)(=O)c1c(ccc(NC(=O)Cc2ccccc2Cl)c1C(F)(F)F)-c1cnn(c1)C(F)F KVMJKCFVZLPEBO-UHFFFAOYSA-N 0.000 claims 1
- IMQZZFQCHRTSJI-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-[1-(difluoromethyl)pyrazol-4-yl]-5-sulfamoyl-2-(trifluoromethyl)phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2ccccc2Cl)c(cc1-c1cnn(c1)C(F)F)C(F)(F)F IMQZZFQCHRTSJI-UHFFFAOYSA-N 0.000 claims 1
- OPLPCLYSPBXJPG-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-[2-(2-hydroxypropan-2-yl)-1,3-thiazol-5-yl]-3-sulfamoylphenyl]acetamide 2-(2-chlorophenyl)-N-[3-sulfamoyl-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)C1=CN=C(S1)C(C)(C)O)S(N)(=O)=O.ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)C=1SC=C(N1)C(F)(F)F)S(N)(=O)=O OPLPCLYSPBXJPG-UHFFFAOYSA-N 0.000 claims 1
- FBANTQAXGUSKLQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-[3-(difluoromethyl)-1,2,4-triazol-1-yl]-3-[(2,4-dimethoxyphenyl)methylsulfamoyl]phenyl]acetamide Chemical compound COc1ccc(CNS(=O)(=O)c2cc(NC(=O)Cc3ccccc3Cl)ccc2-n2cnc(n2)C(F)F)c(OC)c1 FBANTQAXGUSKLQ-UHFFFAOYSA-N 0.000 claims 1
- NKRBYPKNEBEFHB-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-[4-(2,2-difluoroethyl)pyrazol-1-yl]-3-[(2,4-dimethoxyphenyl)methylsulfamoyl]phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)CC(F)F)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O NKRBYPKNEBEFHB-UHFFFAOYSA-N 0.000 claims 1
- OYWKDMLWQADSHR-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-[4-(2,2-difluoroethylamino)pyrazol-1-yl]-3-[(2,4-dimethoxyphenyl)methylsulfamoyl]phenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)NCC(F)F)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O OYWKDMLWQADSHR-UHFFFAOYSA-N 0.000 claims 1
- UPLUVTGCHXLFNE-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-[4-(3,3-difluoroazetidine-1-carbonyl)pyrazol-1-yl]-3-sulfamoylphenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2ccccc2Cl)ccc1-n1cc(cn1)C(=O)N1CC(F)(F)C1 UPLUVTGCHXLFNE-UHFFFAOYSA-N 0.000 claims 1
- ZGMKFEZZAGBGAZ-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-[4-(difluoromethyl)pyrazol-1-yl]-3-sulfamoylphenyl]acetamide 2-(2-chlorophenyl)-N-[5-sulfamoyl-6-[4-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC=1C=NC(=C(C1)S(N)(=O)=O)N1N=CC(=C1)C(F)(F)F.ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C(F)F)S(N)(=O)=O ZGMKFEZZAGBGAZ-UHFFFAOYSA-N 0.000 claims 1
- DDZDRJBURFLRCD-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-[4-[(2,2-difluoroethylamino)methyl]pyrazol-1-yl]-3-sulfamoylphenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)CNCC(F)F)S(N)(=O)=O DDZDRJBURFLRCD-UHFFFAOYSA-N 0.000 claims 1
- CBVBUDSEEGXIRC-IYBDPMFKSA-N 2-(2-chlorophenyl)-N-[4-[4-[(2R,5S)-2,5-dimethylpyrrolidin-1-yl]pyrazol-1-yl]-3-sulfamoylphenyl]acetamide Chemical compound C[C@H]1CC[C@@H](C)N1c1cnn(c1)-c1ccc(NC(=O)Cc2ccccc2Cl)cc1S(N)(=O)=O CBVBUDSEEGXIRC-IYBDPMFKSA-N 0.000 claims 1
- FGKBKRCMQMHDOO-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-[4-chloro-3-(trifluoromethyl)pyrazol-1-yl]-3-sulfamoylphenyl]acetamide 2-(2-chlorophenyl)-N-[4-(3,4-dimethylpyrazol-1-yl)-3-sulfamoylphenyl]acetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=C(C(=C1)C)C)S(N)(=O)=O.ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=C(C(=C1)Cl)C(F)(F)F)S(N)(=O)=O FGKBKRCMQMHDOO-UHFFFAOYSA-N 0.000 claims 1
- UECHMZCALZYWRD-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[4-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-3-[(2,4-dimethoxyphenyl)methylsulfamoyl]phenyl]acetamide Chemical compound COc1ccc(CNS(=O)(=O)c2cc(NC(=O)Cc3ccccc3Cl)ccc2-c2nnc(o2)C(F)F)c(OC)c1 UECHMZCALZYWRD-UHFFFAOYSA-N 0.000 claims 1
- MYYIEEXEJSJHFK-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[5-sulfamoyl-2-(trifluoromethyl)-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2ccccc2Cl)c(cc1-n1cc(cn1)C(F)(F)F)C(F)(F)F MYYIEEXEJSJHFK-UHFFFAOYSA-N 0.000 claims 1
- OGFQTGAABVGWOY-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[6-(4-cyanopyrazol-1-yl)-5-sulfamoylpyridin-3-yl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2ccccc2Cl)cnc1-n1cc(cn1)C#N OGFQTGAABVGWOY-UHFFFAOYSA-N 0.000 claims 1
- IIOPLGGZMXJSJM-UHFFFAOYSA-N 2-(2-chloropyridin-3-yl)-N-[3-sulfamoyl-4-[3-(trifluoromethyl)-1,2,4-triazol-1-yl]phenyl]acetamide Chemical compound ClC1=NC=CC=C1CC(=O)NC1=CC(=C(C=C1)N1N=C(N=C1)C(F)(F)F)S(N)(=O)=O IIOPLGGZMXJSJM-UHFFFAOYSA-N 0.000 claims 1
- ZAEJKTURZRTOJF-UHFFFAOYSA-N 2-(3-chlorophenyl)-N-[3-sulfamoyl-4-[5-(trifluoromethyl)pyridin-3-yl]phenyl]acetamide 2-(4-methylphenyl)-N-[3-sulfamoyl-4-[5-(trifluoromethyl)pyridin-3-yl]phenyl]acetamide Chemical compound CC1=CC=C(C=C1)CC(=O)NC1=CC(=C(C=C1)C=1C=NC=C(C1)C(F)(F)F)S(N)(=O)=O.ClC=1C=C(C=CC1)CC(=O)NC1=CC(=C(C=C1)C=1C=NC=C(C1)C(F)(F)F)S(N)(=O)=O ZAEJKTURZRTOJF-UHFFFAOYSA-N 0.000 claims 1
- YLCJWKZCOBCZLY-UHFFFAOYSA-N 2-(3-chloropyridin-4-yl)-N-[3-sulfamoyl-4-[3-(trifluoromethyl)-1,2,4-triazol-1-yl]phenyl]acetamide Chemical compound ClC=1C=NC=CC=1CC(=O)NC1=CC(=C(C=C1)N1N=C(N=C1)C(F)(F)F)S(N)(=O)=O YLCJWKZCOBCZLY-UHFFFAOYSA-N 0.000 claims 1
- VCQVPDREGQJVIV-UHFFFAOYSA-N 2-(3-chloropyridin-4-yl)-N-[4-(4-cyanopyrazol-1-yl)-3-sulfamoylphenyl]acetamide N-[4-(4-cyanopyrazol-1-yl)-3-sulfamoylphenyl]-2-[4-(difluoromethyl)phenyl]acetamide Chemical compound C(#N)C=1C=NN(C1)C1=C(C=C(C=C1)NC(CC1=CC=C(C=C1)C(F)F)=O)S(N)(=O)=O.ClC=1C=NC=CC1CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C#N)S(N)(=O)=O VCQVPDREGQJVIV-UHFFFAOYSA-N 0.000 claims 1
- AYNQNASJBDNENF-UHFFFAOYSA-N 2-(3-cyclopropylpyrazol-1-yl)-N-[(2,4-dimethoxyphenyl)methyl]-5-nitrobenzenesulfonamide Chemical compound C1(CC1)C1=NN(C=C1)C1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)NCC1=C(C=C(C=C1)OC)OC AYNQNASJBDNENF-UHFFFAOYSA-N 0.000 claims 1
- IAGDUBGJJVAEGH-UHFFFAOYSA-N 2-(4-bromopyrazol-1-yl)-N-[(2,4-dimethoxyphenyl)methyl]-5-nitrobenzenesulfonamide Chemical compound BrC=1C=NN(C=1)C1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)NCC1=C(C=C(C=C1)OC)OC IAGDUBGJJVAEGH-UHFFFAOYSA-N 0.000 claims 1
- WJPIIJHLNLPVBF-UHFFFAOYSA-N 2-(4-chloropyrazol-1-yl)-N-[(2,4-dimethoxyphenyl)methyl]-5-nitrobenzenesulfonamide Chemical compound ClC=1C=NN(C=1)C1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)NCC1=C(C=C(C=C1)OC)OC WJPIIJHLNLPVBF-UHFFFAOYSA-N 0.000 claims 1
- YAFALPCGBLOTTA-UHFFFAOYSA-N 2-(4-cyanopyrazol-1-yl)-5-nitrobenzenesulfonamide Chemical compound C(#N)C=1C=NN(C=1)C1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)N YAFALPCGBLOTTA-UHFFFAOYSA-N 0.000 claims 1
- SRVNIWZFNZSVBC-UHFFFAOYSA-N 2-(4-cyanopyrazol-1-yl)-N-[(2,4-dimethoxyphenyl)methyl]-5-nitrobenzenesulfonamide Chemical compound C(#N)C=1C=NN(C=1)C1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)NCC1=C(C=C(C=C1)OC)OC SRVNIWZFNZSVBC-UHFFFAOYSA-N 0.000 claims 1
- DQRFOSJQFMDSHJ-UHFFFAOYSA-N 2-(4-cyclopropylimidazol-1-yl)-N-[(2,4-dimethoxyphenyl)methyl]-5-nitrobenzenesulfonamide Chemical compound C1(CC1)C=1N=CN(C=1)C1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)NCC1=C(C=C(C=C1)OC)OC DQRFOSJQFMDSHJ-UHFFFAOYSA-N 0.000 claims 1
- OOZGQZARSZOUJN-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[4-(4-fluoropyrazol-1-yl)-3-sulfamoylphenyl]acetamide Chemical compound FC1=CC=C(C=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)F)S(N)(=O)=O OOZGQZARSZOUJN-UHFFFAOYSA-N 0.000 claims 1
- RKBLYIVQUDOLGU-UHFFFAOYSA-N 2-(5-bromo-4-fluoro-2-methylphenyl)-N-[3-sulfamoyl-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound BrC=1C(=CC(=C(C=1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C(F)(F)F)S(N)(=O)=O)C)F RKBLYIVQUDOLGU-UHFFFAOYSA-N 0.000 claims 1
- QMFDJNHWUUDLNN-UHFFFAOYSA-N 2-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-N-[(2,4-dimethoxyphenyl)methyl]-5-nitrobenzenesulfonamide Chemical compound C1(CC1)C1=NC(=NO1)C1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)NCC1=C(C=C(C=C1)OC)OC QMFDJNHWUUDLNN-UHFFFAOYSA-N 0.000 claims 1
- LHCKXYXQCWEGEK-UHFFFAOYSA-N 2-[(2,4-dimethoxyphenyl)methylsulfamoyl]-N'-hydroxy-4-nitrobenzenecarboximidamide Chemical compound COC1=C(CNS(=O)(=O)C2=C(C=CC(=C2)[N+](=O)[O-])C(N)=NO)C=CC(=C1)OC LHCKXYXQCWEGEK-UHFFFAOYSA-N 0.000 claims 1
- CRYMAXVTMJFTJG-UHFFFAOYSA-N 2-[2-(difluoromethoxy)phenyl]-N-[3-sulfamoyl-4-[3-(trifluoromethyl)-1,2,4-triazol-1-yl]phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2ccccc2OC(F)F)ccc1-n1cnc(n1)C(F)(F)F CRYMAXVTMJFTJG-UHFFFAOYSA-N 0.000 claims 1
- CNVOKKQPLDXRLO-UHFFFAOYSA-N 2-[2-chloro-3-(trifluoromethyl)phenyl]-N-[3-sulfamoyl-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound ClC1=C(C=CC=C1C(F)(F)F)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)C(F)(F)F)S(N)(=O)=O CNVOKKQPLDXRLO-UHFFFAOYSA-N 0.000 claims 1
- RJMISFCPOKWUGV-UHFFFAOYSA-N 2-[2-chloro-3-(trifluoromethyl)phenyl]-N-[4-(4-cyanopyrazol-1-yl)-5-sulfamoyl-2-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=C(C=CC=C1C(F)(F)F)CC(=O)NC1=C(C=C(C(=C1)S(N)(=O)=O)N1N=CC(=C1)C#N)C(F)(F)F RJMISFCPOKWUGV-UHFFFAOYSA-N 0.000 claims 1
- WTLKONFDBRCXBH-UHFFFAOYSA-N 2-[2-chloro-3-(trifluoromethyl)phenyl]-N-[4-(4-fluoropyrazol-1-yl)-5-sulfamoyl-2-(trifluoromethyl)phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2cccc(c2Cl)C(F)(F)F)c(cc1-n1cc(F)cn1)C(F)(F)F WTLKONFDBRCXBH-UHFFFAOYSA-N 0.000 claims 1
- HFTNBRFUQUZWKU-UHFFFAOYSA-N 2-[2-chloro-3-(trifluoromethyl)phenyl]-N-[4-[1-(difluoromethyl)pyrazol-4-yl]-3-sulfamoylphenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2cccc(c2Cl)C(F)(F)F)ccc1-c1cnn(c1)C(F)F HFTNBRFUQUZWKU-UHFFFAOYSA-N 0.000 claims 1
- JXRJLJXZDACBRJ-UHFFFAOYSA-N 2-[2-chloro-3-(trifluoromethyl)phenyl]-N-[5-sulfamoyl-2-(trifluoromethyl)-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2cccc(c2Cl)C(F)(F)F)c(cc1-n1cc(cn1)C(F)(F)F)C(F)(F)F JXRJLJXZDACBRJ-UHFFFAOYSA-N 0.000 claims 1
- VFAIDMARDPCQJK-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenyl]-N-[4-(4-fluoropyrazol-1-yl)-5-sulfamoyl-2-(trifluoromethyl)phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2ccc(cc2Cl)C(F)(F)F)c(cc1-n1cc(F)cn1)C(F)(F)F VFAIDMARDPCQJK-UHFFFAOYSA-N 0.000 claims 1
- RTIQZJNAAVIFJB-UHFFFAOYSA-N 2-[2-chloro-5-(trifluoromethyl)phenyl]-N-[4-(4-cyanopyrazol-1-yl)-3-sulfamoylphenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2cc(ccc2Cl)C(F)(F)F)ccc1-n1cc(cn1)C#N RTIQZJNAAVIFJB-UHFFFAOYSA-N 0.000 claims 1
- WJKRZGMDVZRFDQ-UHFFFAOYSA-N 2-[2-chloro-5-(trifluoromethyl)phenyl]-N-[4-(4-cyanopyrazol-1-yl)-5-sulfamoyl-2-(trifluoromethyl)phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2cc(ccc2Cl)C(F)(F)F)c(cc1-n1cc(cn1)C#N)C(F)(F)F WJKRZGMDVZRFDQ-UHFFFAOYSA-N 0.000 claims 1
- JIQFWRDMOKZIBK-UHFFFAOYSA-N 2-[2-chloro-5-(trifluoromethyl)phenyl]-N-[4-(4-fluoropyrazol-1-yl)-5-sulfamoyl-2-(trifluoromethyl)phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2cc(ccc2Cl)C(F)(F)F)c(cc1-n1cc(F)cn1)C(F)(F)F JIQFWRDMOKZIBK-UHFFFAOYSA-N 0.000 claims 1
- HSXYLAUZXDWLSC-UHFFFAOYSA-N 2-[2-chloro-5-(trifluoromethyl)phenyl]-N-[5-sulfamoyl-2-(trifluoromethyl)-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2cc(ccc2Cl)C(F)(F)F)c(cc1-n1cc(cn1)C(F)(F)F)C(F)(F)F HSXYLAUZXDWLSC-UHFFFAOYSA-N 0.000 claims 1
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- FCHGVOAFBNPOFH-UHFFFAOYSA-N N-[(2,4-dimethoxyphenyl)methyl]-5-nitro-2-[4-(2,2,2-trifluoroethylamino)pyrazol-1-yl]benzenesulfonamide Chemical compound COc1ccc(CNS(=O)(=O)c2cc(ccc2-n2cc(NCC(F)(F)F)cn2)[N+]([O-])=O)c(OC)c1 FCHGVOAFBNPOFH-UHFFFAOYSA-N 0.000 claims 1
- MNMLNTUJYASXFO-UHFFFAOYSA-N N-[(2,4-dimethoxyphenyl)methyl]-5-nitro-2-[4-(2-oxoethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound COc1ccc(CNS(=O)(=O)c2cc(ccc2-n2cc(CC=O)cn2)[N+]([O-])=O)c(OC)c1 MNMLNTUJYASXFO-UHFFFAOYSA-N 0.000 claims 1
- ZLJNKPJOGNMHJB-UHFFFAOYSA-N N-[(2,4-dimethoxyphenyl)methyl]-5-nitro-2-[4-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound COC1=C(CNS(=O)(=O)C2=C(C=CC(=C2)[N+](=O)[O-])N2N=CC(=C2)C(F)(F)F)C=CC(=C1)OC ZLJNKPJOGNMHJB-UHFFFAOYSA-N 0.000 claims 1
- ZMFPILOIJLLGGW-UHFFFAOYSA-N N-[(2,4-dimethoxyphenyl)methyl]-5-nitro-2-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenesulfonamide Chemical compound COc1ccc(CNS(=O)(=O)c2cc(ccc2-c2noc(n2)C(F)(F)F)[N+]([O-])=O)c(OC)c1 ZMFPILOIJLLGGW-UHFFFAOYSA-N 0.000 claims 1
- IIWWGHMXIVJQDJ-UHFFFAOYSA-N N-[(2,4-dimethoxyphenyl)methyl]-5-nitro-2-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]benzenesulfonamide Chemical compound COc1ccc(CNS(=O)(=O)c2cc(ccc2-c2nnc(o2)C(F)(F)F)[N+]([O-])=O)c(OC)c1 IIWWGHMXIVJQDJ-UHFFFAOYSA-N 0.000 claims 1
- GAEWFDMNPFDKGU-UHFFFAOYSA-N N-[(2,4-dimethoxyphenyl)methyl]-5-nitro-2-pyrazolo[3,4-b]pyridin-2-ylbenzenesulfonamide Chemical compound COC1=C(CNS(=O)(=O)C2=C(C=CC(=C2)[N+](=O)[O-])N2N=C3N=CC=CC3=C2)C=CC(=C1)OC GAEWFDMNPFDKGU-UHFFFAOYSA-N 0.000 claims 1
- QJYPEMSWMIBIDB-UHFFFAOYSA-N N-[(2,4-dimethoxyphenyl)methyl]-5-nitro-2-pyrazolo[3,4-c]pyridin-2-ylbenzenesulfonamide Chemical compound COC1=C(CNS(=O)(=O)C2=C(C=CC(=C2)[N+](=O)[O-])N2N=C3C=NC=CC3=C2)C=CC(=C1)OC QJYPEMSWMIBIDB-UHFFFAOYSA-N 0.000 claims 1
- CDLGZSYJVYTYKJ-UHFFFAOYSA-N N-[(2,4-dimethoxyphenyl)methyl]-5-nitro-2-pyrazolo[4,3-b]pyridin-2-ylbenzenesulfonamide Chemical compound COC1=C(CNS(=O)(=O)C2=C(C=CC(=C2)[N+](=O)[O-])N2N=C3C(N=CC=C3)=C2)C=CC(=C1)OC CDLGZSYJVYTYKJ-UHFFFAOYSA-N 0.000 claims 1
- PNASJKHRHZXHMA-UHFFFAOYSA-N N-[1-[4-[[2-(2-chlorophenyl)acetyl]amino]-2-[(2,4-dimethoxyphenyl)methylsulfamoyl]phenyl]pyrazol-4-yl]-2,2-difluoroacetamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)NC(C(F)F)=O)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O PNASJKHRHZXHMA-UHFFFAOYSA-N 0.000 claims 1
- WOLMYVDNYORCDL-UHFFFAOYSA-N N-[1-[4-[[2-(2-chlorophenyl)acetyl]amino]-2-[(2,4-dimethoxyphenyl)methylsulfamoyl]phenyl]pyrazol-4-yl]-3,3,3-trifluoro-2-methylpropanamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)NC(C(C(F)(F)F)C)=O)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O WOLMYVDNYORCDL-UHFFFAOYSA-N 0.000 claims 1
- ADYYDQABIFSIHW-UHFFFAOYSA-N N-[1-[4-[[2-(2-chlorophenyl)acetyl]amino]-2-[(2,4-dimethoxyphenyl)methylsulfamoyl]phenyl]pyrazol-4-yl]-3,3,3-trifluoropropanamide Chemical compound ClC1=C(C=CC=C1)CC(=O)NC1=CC(=C(C=C1)N1N=CC(=C1)NC(CC(F)(F)F)=O)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O ADYYDQABIFSIHW-UHFFFAOYSA-N 0.000 claims 1
- UBWGMAVRUHWNHG-UHFFFAOYSA-N N-[1-[4-[[2-(2-chlorophenyl)acetyl]amino]-2-sulfamoylphenyl]pyrazol-4-yl]-3,3,3-trifluoropropanamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2ccccc2Cl)ccc1-n1cc(NC(=O)CC(F)(F)F)cn1 UBWGMAVRUHWNHG-UHFFFAOYSA-N 0.000 claims 1
- BNSIFAXJAQNLBK-UHFFFAOYSA-N N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-(4-methylpyrazol-1-yl)phenyl]-2-(2-fluorophenyl)acetamide Chemical compound COC1=C(CNS(=O)(=O)C=2C=C(C=CC=2N2N=CC(=C2)C)NC(CC2=C(C=CC=C2)F)=O)C=CC(=C1)OC BNSIFAXJAQNLBK-UHFFFAOYSA-N 0.000 claims 1
- YBHHIRSVZNIXME-UHFFFAOYSA-N N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-(4-propan-2-ylpyrazol-1-yl)phenyl]-2-(2-fluorophenyl)acetamide Chemical compound COC1=C(CNS(=O)(=O)C=2C=C(C=CC=2N2N=CC(=C2)C(C)C)NC(CC2=C(C=CC=C2)F)=O)C=CC(=C1)OC YBHHIRSVZNIXME-UHFFFAOYSA-N 0.000 claims 1
- FQOWKTRXLPVYRN-UHFFFAOYSA-N N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-[4-(2,2,2-trifluoroethyl)pyrazol-1-yl]phenyl]-2-(2-fluorophenyl)acetamide Chemical compound COc1ccc(CNS(=O)(=O)c2cc(NC(=O)Cc3ccccc3F)ccc2-n2cc(CC(F)(F)F)cn2)c(OC)c1 FQOWKTRXLPVYRN-UHFFFAOYSA-N 0.000 claims 1
- XFEUDQXBJGLTEB-UHFFFAOYSA-N N-[3-[(2,4-dimethoxyphenyl)methylsulfamoyl]-4-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]phenyl]-2-(2-fluorophenyl)acetamide Chemical compound COC1=C(CNS(=O)(=O)C=2C=C(C=CC=2C=2OC(=NN=2)C(F)(F)F)NC(CC2=C(C=CC=C2)F)=O)C=CC(=C1)OC XFEUDQXBJGLTEB-UHFFFAOYSA-N 0.000 claims 1
- TWBGNRGFIAOVDB-UHFFFAOYSA-N N-[3-sulfamoyl-4-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]-2-[2-(trifluoromethoxy)phenyl]acetamide Chemical compound S(N)(=O)(=O)C=1C=C(C=CC=1N1N=CC(=C1)C(F)(F)F)NC(CC1=C(C=CC=C1)OC(F)(F)F)=O TWBGNRGFIAOVDB-UHFFFAOYSA-N 0.000 claims 1
- KPMIIVCYNIHLND-UHFFFAOYSA-N N-[3-sulfamoyl-4-[5-(trifluoromethyl)pyridin-3-yl]phenyl]-2-[2-(trifluoromethyl)phenyl]acetamide Chemical compound NS(=O)(=O)c1cc(NC(=O)Cc2ccccc2C(F)(F)F)ccc1-c1cncc(c1)C(F)(F)F KPMIIVCYNIHLND-UHFFFAOYSA-N 0.000 claims 1
- WAAXXNKFTNZFPG-UHFFFAOYSA-N N-[4-(3-cyclopropylpyrazol-1-yl)-3-[(2,4-dimethoxyphenyl)methylsulfamoyl]phenyl]-2-(2-fluorophenyl)acetamide Chemical compound C1(CC1)C1=NN(C=C1)C1=C(C=C(C=C1)NC(CC1=C(C=CC=C1)F)=O)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O WAAXXNKFTNZFPG-UHFFFAOYSA-N 0.000 claims 1
- SNDWIHIUWCSOKL-UHFFFAOYSA-N N-[4-(4-aminopyrazol-1-yl)-3-[(2,4-dimethoxyphenyl)methylsulfamoyl]phenyl]-2-(2-chlorophenyl)acetamide Chemical compound NC=1C=NN(C=1)C1=C(C=C(C=C1)NC(CC1=C(C=CC=C1)Cl)=O)S(NCC1=C(C=C(C=C1)OC)OC)(=O)=O SNDWIHIUWCSOKL-UHFFFAOYSA-N 0.000 claims 1
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| CN111511720A (zh) * | 2017-10-29 | 2020-08-07 | 拜耳股份公司 | 用于治疗缺血性中风的芳族磺酰胺衍生物 |
| EP3844150A1 (en) | 2018-08-31 | 2021-07-07 | Xenon Pharmaceuticals Inc. | Heteroaryl-substituted sulfonamide compounds and their use as therapeutic agents |
| JP7492005B2 (ja) * | 2019-11-29 | 2024-05-28 | 武漢朗来科技発展有限公司 | ベンゼン環含有化合物及びその応用 |
| CN113082023B (zh) * | 2019-12-23 | 2024-03-01 | 武汉朗来科技发展有限公司 | P2x3抑制剂和p2x4抑制剂的药物组合及其应用 |
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| CN111511720A (zh) * | 2017-10-29 | 2020-08-07 | 拜耳股份公司 | 用于治疗缺血性中风的芳族磺酰胺衍生物 |
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