CA2461567C - Substituted pyrazolyl benzenesulfamide compounds for the treatment of inflammation - Google Patents
Substituted pyrazolyl benzenesulfamide compounds for the treatment of inflammation Download PDFInfo
- Publication number
- CA2461567C CA2461567C CA002461567A CA2461567A CA2461567C CA 2461567 C CA2461567 C CA 2461567C CA 002461567 A CA002461567 A CA 002461567A CA 2461567 A CA2461567 A CA 2461567A CA 2461567 C CA2461567 C CA 2461567C
- Authority
- CA
- Canada
- Prior art keywords
- benzo
- indazole
- carboxamide
- amino
- compound
- 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.)
- Expired - Fee Related
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- -1 pyrazolyl benzenesulfamide compounds Chemical class 0.000 title claims description 138
- 206010061218 Inflammation Diseases 0.000 title abstract description 16
- 230000004054 inflammatory process Effects 0.000 title abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims description 153
- 150000003839 salts Chemical class 0.000 claims description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- DITBWPUMEUDVLU-UHFFFAOYSA-N 1h-indazole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=NNC2=C1 DITBWPUMEUDVLU-UHFFFAOYSA-N 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 4
- YSENAEKMLMQUTO-UHFFFAOYSA-N 8-[(2-chlorobenzoyl)amino]-1-(4-methylsulfonylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=C3C=C(NC(=O)C=4C(=CC=CC=4)Cl)C=CC3=CC=C2C(C(N)=O)=N1 YSENAEKMLMQUTO-UHFFFAOYSA-N 0.000 claims description 3
- IRJIRVSKERCRMY-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-8-[(2-chlorobenzoyl)amino]benzo[g]indazole-3-carboxamide Chemical compound NC(=O)C1=NN(C=2C=C3OCOC3=CC=2)C(C2=C3)=C1C=CC2=CC=C3NC(=O)C1=CC=CC=C1Cl IRJIRVSKERCRMY-UHFFFAOYSA-N 0.000 claims description 2
- OYIRAXMOKCBHOO-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-8-[(3-chloropyridine-4-carbonyl)amino]benzo[g]indazole-3-carboxamide Chemical compound NC(=O)C1=NN(C=2C=C3OCOC3=CC=2)C(C2=C3)=C1C=CC2=CC=C3NC(=O)C1=CC=NC=C1Cl OYIRAXMOKCBHOO-UHFFFAOYSA-N 0.000 claims description 2
- NMYOONGGAWQTBP-UHFFFAOYSA-N 8-[(2-chlorobenzoyl)amino]-1-(3-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C(=CC=CC=3)Cl)C=C2C2=C1C(C(=O)N)=NN2C1=CC=CC(S(N)(=O)=O)=C1 NMYOONGGAWQTBP-UHFFFAOYSA-N 0.000 claims description 2
- AXTAWXZBXIYFRD-UHFFFAOYSA-N 8-[(3-chloropyridine-4-carbonyl)amino]-1-(4-fluorophenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C(=CN=CC=3)Cl)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(F)C=C1 AXTAWXZBXIYFRD-UHFFFAOYSA-N 0.000 claims description 2
- XJJRJIBGSRKMKZ-UHFFFAOYSA-N 8-amino-1-(1,3-benzodioxol-5-yl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(N)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(OCO2)C2=C1 XJJRJIBGSRKMKZ-UHFFFAOYSA-N 0.000 claims description 2
- ZOWYAWPJDSTETF-UHFFFAOYSA-N 8-amino-1-(4-fluorophenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(N)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(F)C=C1 ZOWYAWPJDSTETF-UHFFFAOYSA-N 0.000 claims description 2
- QKEFWPKESMVSLC-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-5-bromo-8-[(2-chloropyridine-3-carbonyl)amino]benzo[g]indazole-3-carboxamide Chemical compound NC(=O)C1=NN(C=2C=C3OCOC3=CC=2)C(C2=C3)=C1C=C(Br)C2=CC=C3NC(=O)C1=CC=CN=C1Cl QKEFWPKESMVSLC-UHFFFAOYSA-N 0.000 claims 1
- HDBKIRZVBCKYEO-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-8-[(2-chloropyridine-3-carbonyl)amino]benzo[g]indazole-3-carboxamide Chemical compound NC(=O)C1=NN(C=2C=C3OCOC3=CC=2)C(C2=C3)=C1C=CC2=CC=C3NC(=O)C1=CC=CN=C1Cl HDBKIRZVBCKYEO-UHFFFAOYSA-N 0.000 claims 1
- VBSNYYOEBYLXIE-UHFFFAOYSA-N 1-(4-fluorophenyl)-8-(methanesulfonamido)benzo[g]indazole-3-carboxamide Chemical compound C1=2C3=CC(NS(=O)(=O)C)=CC=C3C=CC=2C(C(N)=O)=NN1C1=CC=C(F)C=C1 VBSNYYOEBYLXIE-UHFFFAOYSA-N 0.000 claims 1
- VSGFWUNCQSGEIK-UHFFFAOYSA-N 1-(4-fluorophenyl)-8-[(4-methylpiperazine-1-carbonyl)amino]benzo[g]indazole-3-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC1=CC=C(C=CC2=C3N(C=4C=CC(F)=CC=4)N=C2C(N)=O)C3=C1 VSGFWUNCQSGEIK-UHFFFAOYSA-N 0.000 claims 1
- VYYTWHWXHOFAFM-UHFFFAOYSA-N 1-(4-methylsulfonylphenyl)-8-[[2-(trifluoromethyl)benzoyl]amino]benzo[g]indazole-3-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=C3C=C(NC(=O)C=4C(=CC=CC=4)C(F)(F)F)C=CC3=CC=C2C(C(N)=O)=N1 VYYTWHWXHOFAFM-UHFFFAOYSA-N 0.000 claims 1
- UAJVYIZILZLPPG-UHFFFAOYSA-N 1-(4-sulfamoylphenyl)-8-[(2,4,5-trichlorophenyl)sulfonylamino]benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NS(=O)(=O)C=3C(=CC(Cl)=C(Cl)C=3)Cl)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 UAJVYIZILZLPPG-UHFFFAOYSA-N 0.000 claims 1
- CWTJBNYVAMWZKR-UHFFFAOYSA-N 1-(4-sulfamoylphenyl)-8-[[2-(trifluoromethoxy)benzoyl]amino]benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C(=CC=CC=3)OC(F)(F)F)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 CWTJBNYVAMWZKR-UHFFFAOYSA-N 0.000 claims 1
- OWBDGHXIGRTSDQ-UHFFFAOYSA-N 1-(4-sulfamoylphenyl)-8-[[2-(trifluoromethyl)benzoyl]amino]benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C(=CC=CC=3)C(F)(F)F)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 OWBDGHXIGRTSDQ-UHFFFAOYSA-N 0.000 claims 1
- ZHARIULECHTJBG-UHFFFAOYSA-N 1-(4-sulfamoylphenyl)-8-[[3-(trifluoromethyl)benzoyl]amino]benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 ZHARIULECHTJBG-UHFFFAOYSA-N 0.000 claims 1
- PLIKKMXVSLCITH-UHFFFAOYSA-N 1-(4-sulfamoylphenyl)-8-[[3-(trifluoromethyl)phenyl]sulfonylamino]benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NS(=O)(=O)C=3C=C(C=CC=3)C(F)(F)F)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 PLIKKMXVSLCITH-UHFFFAOYSA-N 0.000 claims 1
- RBRJBLJYCSQGOP-UHFFFAOYSA-N 5-bromo-8-[(3-chloropyridine-4-carbonyl)amino]-1-(4-fluorophenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=C(Br)C2=CC=C(NC(=O)C=3C(=CN=CC=3)Cl)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(F)C=C1 RBRJBLJYCSQGOP-UHFFFAOYSA-N 0.000 claims 1
- WSBCJXSDSZGMNA-UHFFFAOYSA-N 8-(methanesulfonamido)-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=2C3=CC(NS(=O)(=O)C)=CC=C3C=CC=2C(C(N)=O)=NN1C1=CC=C(S(N)(=O)=O)C=C1 WSBCJXSDSZGMNA-UHFFFAOYSA-N 0.000 claims 1
- HKXRBVAXMSVGPO-UHFFFAOYSA-N 8-(pyridine-3-carbonylamino)-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C=NC=CC=3)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 HKXRBVAXMSVGPO-UHFFFAOYSA-N 0.000 claims 1
- WRRCTFCMOOGHLF-UHFFFAOYSA-N 8-(pyridine-4-carbonylamino)-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C=CN=CC=3)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 WRRCTFCMOOGHLF-UHFFFAOYSA-N 0.000 claims 1
- OYFLVROKNUKMSS-UHFFFAOYSA-N 8-[(2,3-dichlorobenzoyl)amino]-1-(4-methylsulfonylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=C3C=C(NC(=O)C=4C(=C(Cl)C=CC=4)Cl)C=CC3=CC=C2C(C(N)=O)=N1 OYFLVROKNUKMSS-UHFFFAOYSA-N 0.000 claims 1
- OJYJVDZWGQXTJM-UHFFFAOYSA-N 8-[(2,3-dichlorobenzoyl)amino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C(=C(Cl)C=CC=3)Cl)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 OJYJVDZWGQXTJM-UHFFFAOYSA-N 0.000 claims 1
- JKNISKROFGFKIS-UHFFFAOYSA-N 8-[(2,6-dichlorobenzoyl)amino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C(=CC=CC=3Cl)Cl)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 JKNISKROFGFKIS-UHFFFAOYSA-N 0.000 claims 1
- LCMARONKGAIQHX-UHFFFAOYSA-N 8-[(2-chlorobenzoyl)amino]-1-(3-fluorophenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C(=CC=CC=3)Cl)C=C2C2=C1C(C(=O)N)=NN2C1=CC=CC(F)=C1 LCMARONKGAIQHX-UHFFFAOYSA-N 0.000 claims 1
- GGIDEVVLGIXWGV-UHFFFAOYSA-N 8-[(2-chlorobenzoyl)amino]-1-(4-fluorophenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C(=CC=CC=3)Cl)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(F)C=C1 GGIDEVVLGIXWGV-UHFFFAOYSA-N 0.000 claims 1
- YTVRMYRLSBIWDZ-UHFFFAOYSA-N 8-[(2-chlorobenzoyl)amino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C(=CC=CC=3)Cl)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 YTVRMYRLSBIWDZ-UHFFFAOYSA-N 0.000 claims 1
- AMMVEXZQWZFDSY-UHFFFAOYSA-N 8-[(2-chlorophenyl)sulfonylamino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NS(=O)(=O)C=3C(=CC=CC=3)Cl)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 AMMVEXZQWZFDSY-UHFFFAOYSA-N 0.000 claims 1
- GCGCEIVFHMGWGN-UHFFFAOYSA-N 8-[(2-chloropyridine-3-carbonyl)amino]-1-(2,4-difluorophenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C(=NC=CC=3)Cl)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(F)C=C1F GCGCEIVFHMGWGN-UHFFFAOYSA-N 0.000 claims 1
- AHOHBBAUQRVGCC-UHFFFAOYSA-N 8-[(2-chloropyridine-3-carbonyl)amino]-1-(4-fluorophenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C(=NC=CC=3)Cl)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(F)C=C1 AHOHBBAUQRVGCC-UHFFFAOYSA-N 0.000 claims 1
- GPYJOURSTWRTKQ-UHFFFAOYSA-N 8-[(2-chloropyridine-3-carbonyl)amino]-1-(4-methylsulfonylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=C3C=C(NC(=O)C=4C(=NC=CC=4)Cl)C=CC3=CC=C2C(C(N)=O)=N1 GPYJOURSTWRTKQ-UHFFFAOYSA-N 0.000 claims 1
- DHVRFCPOWAEZIE-UHFFFAOYSA-N 8-[(2-chloropyridine-3-carbonyl)amino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C(=NC=CC=3)Cl)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 DHVRFCPOWAEZIE-UHFFFAOYSA-N 0.000 claims 1
- QBUSCYKEOVJXKP-UHFFFAOYSA-N 8-[(2-fluorobenzoyl)amino]-1-(4-methylsulfonylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=C3C=C(NC(=O)C=4C(=CC=CC=4)F)C=CC3=CC=C2C(C(N)=O)=N1 QBUSCYKEOVJXKP-UHFFFAOYSA-N 0.000 claims 1
- TZKFVQABKHKXCC-UHFFFAOYSA-N 8-[(2-fluorobenzoyl)amino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C(=CC=CC=3)F)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 TZKFVQABKHKXCC-UHFFFAOYSA-N 0.000 claims 1
- HUMNCGXAIMQQQC-UHFFFAOYSA-N 8-[(2-methoxybenzoyl)amino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound COC1=CC=CC=C1C(=O)NC1=CC=C(C=CC2=C3N(C=4C=CC(=CC=4)S(N)(=O)=O)N=C2C(N)=O)C3=C1 HUMNCGXAIMQQQC-UHFFFAOYSA-N 0.000 claims 1
- LRSSLIUHVLUOPN-UHFFFAOYSA-N 8-[(2-methylbenzoyl)amino]-1-(4-methylsulfonylphenyl)benzo[g]indazole-3-carboxamide Chemical compound CC1=CC=CC=C1C(=O)NC1=CC=C(C=CC2=C3N(C=4C=CC(=CC=4)S(C)(=O)=O)N=C2C(N)=O)C3=C1 LRSSLIUHVLUOPN-UHFFFAOYSA-N 0.000 claims 1
- YNXNBVXNPMPOOL-UHFFFAOYSA-N 8-[(2-methylbenzoyl)amino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound CC1=CC=CC=C1C(=O)NC1=CC=C(C=CC2=C3N(C=4C=CC(=CC=4)S(N)(=O)=O)N=C2C(N)=O)C3=C1 YNXNBVXNPMPOOL-UHFFFAOYSA-N 0.000 claims 1
- DRCYKKRDZNGWSL-UHFFFAOYSA-N 8-[(3,4-dichlorophenyl)sulfonylamino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NS(=O)(=O)C=3C=C(Cl)C(Cl)=CC=3)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 DRCYKKRDZNGWSL-UHFFFAOYSA-N 0.000 claims 1
- UDEVUXGQAWKILK-UHFFFAOYSA-N 8-[(3-bromobenzoyl)amino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C=C(Br)C=CC=3)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 UDEVUXGQAWKILK-UHFFFAOYSA-N 0.000 claims 1
- FKULKEFTJCTKTK-UHFFFAOYSA-N 8-[(3-bromophenyl)sulfonylamino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NS(=O)(=O)C=3C=C(Br)C=CC=3)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 FKULKEFTJCTKTK-UHFFFAOYSA-N 0.000 claims 1
- ABKYIIHCGGMFDF-UHFFFAOYSA-N 8-[(3-chlorobenzoyl)amino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C=C(Cl)C=CC=3)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 ABKYIIHCGGMFDF-UHFFFAOYSA-N 0.000 claims 1
- SPYVYTSXPDERML-UHFFFAOYSA-N 8-[(3-chlorophenyl)sulfonylamino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NS(=O)(=O)C=3C=C(Cl)C=CC=3)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 SPYVYTSXPDERML-UHFFFAOYSA-N 0.000 claims 1
- DAOBPMJSYDOSBJ-UHFFFAOYSA-N 8-[(3-cyanobenzoyl)amino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NC(=O)C=3C=C(C=CC=3)C#N)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 DAOBPMJSYDOSBJ-UHFFFAOYSA-N 0.000 claims 1
- AEKWFICQAOHHBI-UHFFFAOYSA-N 8-[(3-methoxybenzoyl)amino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C3C=4N(C=5C=CC(=CC=5)S(N)(=O)=O)N=C(C=4C=CC3=CC=2)C(N)=O)=C1 AEKWFICQAOHHBI-UHFFFAOYSA-N 0.000 claims 1
- RVNAKHRUZLIOEG-UHFFFAOYSA-N 8-[(3-methylbenzoyl)amino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound CC1=CC=CC(C(=O)NC=2C=C3C=4N(C=5C=CC(=CC=5)S(N)(=O)=O)N=C(C=4C=CC3=CC=2)C(N)=O)=C1 RVNAKHRUZLIOEG-UHFFFAOYSA-N 0.000 claims 1
- NTLPMPYLLGCQQI-UHFFFAOYSA-N 8-[(3-methylphenyl)sulfonylamino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound CC1=CC=CC(S(=O)(=O)NC=2C=C3C=4N(C=5C=CC(=CC=5)S(N)(=O)=O)N=C(C=4C=CC3=CC=2)C(N)=O)=C1 NTLPMPYLLGCQQI-UHFFFAOYSA-N 0.000 claims 1
- AZXNQYZFYVIBLL-UHFFFAOYSA-N 8-[[3,5-bis(trifluoromethyl)phenyl]sulfonylamino]-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(NS(=O)(=O)C=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)C=C2C2=C1C(C(=O)N)=NN2C1=CC=C(S(N)(=O)=O)C=C1 AZXNQYZFYVIBLL-UHFFFAOYSA-N 0.000 claims 1
- CBBHFNVGJXKVMY-UHFFFAOYSA-N 8-acetamido-1-(4-sulfamoylphenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=2C3=CC(NC(=O)C)=CC=C3C=CC=2C(C(N)=O)=NN1C1=CC=C(S(N)(=O)=O)C=C1 CBBHFNVGJXKVMY-UHFFFAOYSA-N 0.000 claims 1
- UAGGSCIBLJUTQK-UHFFFAOYSA-N 8-amino-1-(3-fluorophenyl)benzo[g]indazole-3-carboxamide Chemical compound C1=CC2=CC=C(N)C=C2C2=C1C(C(=O)N)=NN2C1=CC=CC(F)=C1 UAGGSCIBLJUTQK-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 13
- 206010028980 Neoplasm Diseases 0.000 abstract description 10
- 208000035475 disorder Diseases 0.000 abstract description 9
- 239000000543 intermediate Substances 0.000 abstract description 8
- 201000011510 cancer Diseases 0.000 abstract description 6
- 206010003246 arthritis Diseases 0.000 abstract description 5
- 125000003226 pyrazolyl group Chemical group 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 description 66
- 125000003118 aryl group Chemical group 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 125000001072 heteroaryl group Chemical group 0.000 description 48
- 150000003254 radicals Chemical group 0.000 description 47
- 125000000623 heterocyclic group Chemical group 0.000 description 44
- 210000004027 cell Anatomy 0.000 description 43
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 42
- 125000001188 haloalkyl group Chemical group 0.000 description 40
- 125000001145 hydrido group Chemical group *[H] 0.000 description 38
- 101710205525 Inhibitor of nuclear factor kappa-B kinase subunit beta Proteins 0.000 description 32
- 102100021854 Inhibitor of nuclear factor kappa-B kinase subunit beta Human genes 0.000 description 32
- 239000011347 resin Substances 0.000 description 31
- 229920005989 resin Polymers 0.000 description 31
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 30
- 125000003710 aryl alkyl group Chemical group 0.000 description 30
- 230000000694 effects Effects 0.000 description 29
- 239000000872 buffer Substances 0.000 description 28
- 108090000623 proteins and genes Proteins 0.000 description 26
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- Vascular Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Communicable Diseases (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Reproductive Health (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32323001P | 2001-09-19 | 2001-09-19 | |
| US60/323,230 | 2001-09-19 | ||
| PCT/US2002/029673 WO2003027075A2 (en) | 2001-09-19 | 2002-09-19 | Substituted pyrazolyl benzenesulfamide compounds for the treatment of inflammation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2461567A1 CA2461567A1 (en) | 2003-04-03 |
| CA2461567C true CA2461567C (en) | 2008-08-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002461567A Expired - Fee Related CA2461567C (en) | 2001-09-19 | 2002-09-19 | Substituted pyrazolyl benzenesulfamide compounds for the treatment of inflammation |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6849653B2 (enExample) |
| EP (1) | EP1438293A2 (enExample) |
| JP (1) | JP2005507892A (enExample) |
| BR (1) | BR0212661A (enExample) |
| CA (1) | CA2461567C (enExample) |
| MX (1) | MXPA04002683A (enExample) |
| WO (1) | WO2003027075A2 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040092552A1 (en) * | 2000-04-25 | 2004-05-13 | Brown David L | 2-Fluorobenzenesulfonyl compounds for the treatment of inflammation |
| UA79804C2 (en) * | 2002-07-03 | 2007-07-25 | Janssen Pharmaceutica Nv | Cck-1 receptor modulators |
| EP1556053A4 (en) | 2002-10-31 | 2006-04-19 | Amgen Inc | ANTI-INFLAMMATORY AGENTS |
| US7572914B2 (en) * | 2003-12-19 | 2009-08-11 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| US7276050B2 (en) * | 2004-03-02 | 2007-10-02 | Alan Franklin | Trans-scleral drug delivery method and apparatus |
| WO2005105788A1 (en) * | 2004-04-23 | 2005-11-10 | Takeda San Diego, Inc. | Indole derivatives and use thereof as kinase inhibitors |
| TW200616967A (en) | 2004-06-24 | 2006-06-01 | Smithkline Beecham Corp | Novel indazole carboxamides and their use |
| WO2006023931A2 (en) * | 2004-08-18 | 2006-03-02 | Takeda San Diego, Inc. | Kinase inhibitors |
| TW200626142A (en) | 2004-09-21 | 2006-08-01 | Glaxo Group Ltd | Chemical compounds |
| EP1812439B2 (en) | 2004-10-15 | 2017-12-06 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| US8063071B2 (en) | 2007-10-31 | 2011-11-22 | GlaxoSmithKline, LLC | Chemical compounds |
| NZ563687A (en) | 2005-06-30 | 2011-07-29 | Smithkline Beecham Corp | 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[2-(1-methylethyl)-2,3-dihydro-1H-isoindol-5-yl]-1H-indole-7-carboxamide for inhibiting IKK2 (aka IKKbeta) |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| AR058223A1 (es) * | 2005-11-25 | 2008-01-23 | Palau Pharma Sa | Un comuesto de derivados de pirazoloisoquinolina, un procedimiento para l a preparacion de dicho compuesto y una composicion farmaceutica que comprende dicho compuesto |
| JP2010505962A (ja) | 2006-10-09 | 2010-02-25 | 武田薬品工業株式会社 | キナーゼ阻害剤 |
| AR065804A1 (es) | 2007-03-23 | 2009-07-01 | Smithkline Beecham Corp | Compuesto de indol carboxamida, composicion farmaceutica que lo comprende y uso de dicho compuesto para preparar un medicamento |
| US8354539B2 (en) | 2009-03-10 | 2013-01-15 | Glaxo Group Limited | Indole derivatives as IKK2 inhibitors |
| EP3795694A3 (en) | 2012-10-02 | 2021-06-23 | The General Hospital Corporation d/b/a Massachusetts General Hospital | Methods relating to dna-sensing pathway related conditions |
| WO2015112792A1 (en) * | 2014-01-24 | 2015-07-30 | Abbvie Inc. | Aryl and arylalkyl substituted pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators |
| TWI831738B (zh) | 2016-12-16 | 2024-02-11 | 美商瑞塔醫藥有限責任公司 | 用於抑制ＲＯＲγ及其他用途的嘧啶三環烯酮衍生物 |
| US11993574B2 (en) | 2018-06-15 | 2024-05-28 | Reata Pharmaceuticals, Inc | Pyrazole and imidazole compounds for inhibition of IL-17 and RORgamma |
| US12060340B2 (en) | 2018-06-20 | 2024-08-13 | Reata Pharmaceuticals, Inc | Cysteine-dependent inverse agonists of nuclear receptors ROR-gamma/ROR-gamma-t and methods of treating diseases or disorders therewith |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3940418A (en) * | 1972-04-07 | 1976-02-24 | G. D. Searle & Co. | Esters and amides of 4,5-dihydrobenz[g]indazole-3-carboxylic acids and related compounds |
| GB8814587D0 (en) | 1988-06-20 | 1988-07-27 | Erba Carlo Spa | Condensed pyrazole 3-oxo-propanenitrile derivatives & process for their preparation |
| US5260328A (en) * | 1989-04-06 | 1993-11-09 | Farmitalia Carlo Erba Srl | Phenyl-indenopurazol 3-oxo-propanamide derivatives useful in the treatment of rheumatoid arthritis |
| PH27357A (en) * | 1989-09-22 | 1993-06-21 | Fujisawa Pharmaceutical Co | Pyrazole derivatives and pharmaceutical compositions comprising the same |
| FR2665898B1 (fr) | 1990-08-20 | 1994-03-11 | Sanofi | Derives d'amido-3 pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| US5134155A (en) * | 1991-08-08 | 1992-07-28 | Ortho Pharmaceutical Corporation | Tetrahydroindazole, tetrahydrocyclopentapyrazole, and hexahydrocycloheptapyrazole compounds and their use as HMG-coA reductase inhibitors |
| US5434178A (en) | 1993-11-30 | 1995-07-18 | G.D. Searle & Co. | 1,3,5 trisubstituted pyrazole compounds for treatment of inflammation |
| US5696143A (en) * | 1994-09-20 | 1997-12-09 | Talley; John J. | Benz G! indazolyl derivatives for the treatment of inflammation |
| AU4006795A (en) | 1994-11-10 | 1996-06-06 | Olin Corporation | Process for gas phase chlorine dioxide delignification |
| EP1127051A2 (en) | 1998-11-06 | 2001-08-29 | Basf Aktiengesellschaft | Tricyclic pyrazole derivatives |
| WO2000059901A1 (en) | 1999-04-06 | 2000-10-12 | Knoll Gesellschaft Mit Beschraenkter Haftung | Substituted 1,4-dihydroindeno[1,2-c]pyrazoles as inhibitors of tyrosine kinase |
-
2002
- 2002-09-19 JP JP2003530666A patent/JP2005507892A/ja active Pending
- 2002-09-19 EP EP02778279A patent/EP1438293A2/en not_active Withdrawn
- 2002-09-19 BR BR0212661-3A patent/BR0212661A/pt not_active IP Right Cessation
- 2002-09-19 US US10/247,021 patent/US6849653B2/en not_active Expired - Fee Related
- 2002-09-19 CA CA002461567A patent/CA2461567C/en not_active Expired - Fee Related
- 2002-09-19 MX MXPA04002683A patent/MXPA04002683A/es active IP Right Grant
- 2002-09-19 WO PCT/US2002/029673 patent/WO2003027075A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003027075A2 (en) | 2003-04-03 |
| US20030125361A1 (en) | 2003-07-03 |
| EP1438293A2 (en) | 2004-07-21 |
| MXPA04002683A (es) | 2004-06-18 |
| JP2005507892A (ja) | 2005-03-24 |
| WO2003027075A3 (en) | 2003-08-21 |
| BR0212661A (pt) | 2004-08-24 |
| US6849653B2 (en) | 2005-02-01 |
| CA2461567A1 (en) | 2003-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |