DE69422306T4 - Substituierte pyrazolyl-benzolsulfonamide zur behandlung von entzündungen - Google Patents
Substituierte pyrazolyl-benzolsulfonamide zur behandlung von entzündungenInfo
- Publication number
- DE69422306T4 DE69422306T4 DE69422306T DE69422306T DE69422306T4 DE 69422306 T4 DE69422306 T4 DE 69422306T4 DE 69422306 T DE69422306 T DE 69422306T DE 69422306 T DE69422306 T DE 69422306T DE 69422306 T4 DE69422306 T4 DE 69422306T4
- Authority
- DE
- Germany
- Prior art keywords
- pyrazol
- benzenesulfonamide
- trifluoromethyl
- phenyl
- chloro
- 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 - Lifetime
Links
- 230000004054 inflammatory process Effects 0.000 title abstract description 14
- 206010061218 Inflammation Diseases 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- -1 C1 -C10 alkyl Chemical group 0.000 claims description 163
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 29
- NSQNZEUFHPTJME-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C(F)(F)F)=N1 NSQNZEUFHPTJME-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- JDCWOBTUQSMXDU-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(difluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C(F)F)=N1 JDCWOBTUQSMXDU-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Chemical group 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- WAZQAZKAZLXFMK-UHFFFAOYSA-N deracoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 WAZQAZKAZLXFMK-UHFFFAOYSA-N 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- VSQLZYPQFJIORU-UHFFFAOYSA-N 4-[3-(difluoromethyl)-5-(4-methoxyphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 VSQLZYPQFJIORU-UHFFFAOYSA-N 0.000 claims description 6
- XRHRZRHLXNWUTF-UHFFFAOYSA-N 4-[4-chloro-5-(4-chlorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical class C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=C(Cl)C(C(F)(F)F)=N1 XRHRZRHLXNWUTF-UHFFFAOYSA-N 0.000 claims description 6
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 6
- HIWZHRWGHFMASQ-UHFFFAOYSA-N 4-[4-methyl-5-phenyl-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound CC=1C(C(F)(F)F)=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C=1C1=CC=CC=C1 HIWZHRWGHFMASQ-UHFFFAOYSA-N 0.000 claims description 5
- HUXWHUIRGULKHT-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-(3-hydroxypropyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(F)=CC=2)=CC(CCCO)=N1 HUXWHUIRGULKHT-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- AUDIKJKYMGBIIN-UHFFFAOYSA-N n-(3-chlorophenyl)-5-(4-fluorophenyl)-1-(4-sulfamoylphenyl)pyrazole-3-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(F)=CC=2)=CC(C(=O)NC=2C=C(Cl)C=CC=2)=N1 AUDIKJKYMGBIIN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- AJYWXMJXJSEWLW-UHFFFAOYSA-N 4-(4-chloro-5-phenylpyrazol-1-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=C(Cl)C=N1 AJYWXMJXJSEWLW-UHFFFAOYSA-N 0.000 claims description 4
- ZFFYQVIHYPYXPI-UHFFFAOYSA-N 4-[3-(difluoromethyl)-5-phenylpyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=CC(C(F)F)=N1 ZFFYQVIHYPYXPI-UHFFFAOYSA-N 0.000 claims description 4
- ONLJCFGOAOBBRC-UHFFFAOYSA-N 4-[3-[chloro(difluoro)methyl]-5-(4-chlorophenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C(F)(F)Cl)=N1 ONLJCFGOAOBBRC-UHFFFAOYSA-N 0.000 claims description 4
- UUGSJYRNELHGOL-UHFFFAOYSA-N 4-[3-cyano-5-(4-fluorophenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(F)=CC=2)=CC(C#N)=N1 UUGSJYRNELHGOL-UHFFFAOYSA-N 0.000 claims description 4
- JTDYOAXMJCYREN-UHFFFAOYSA-N 4-[4-chloro-5-(4-chlorophenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=C(Cl)C=N1 JTDYOAXMJCYREN-UHFFFAOYSA-N 0.000 claims description 4
- XKWYBHGPQNBIPG-UHFFFAOYSA-N 4-[4-ethyl-5-(4-methoxy-3-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound CCC=1C(C(F)(F)F)=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C=1C1=CC=C(OC)C(C)=C1 XKWYBHGPQNBIPG-UHFFFAOYSA-N 0.000 claims description 4
- FUHLJNQTSZQWBE-UHFFFAOYSA-N 4-[4-fluoro-5-phenyl-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=C(F)C(C(F)(F)F)=N1 FUHLJNQTSZQWBE-UHFFFAOYSA-N 0.000 claims description 4
- FRACLAJOOXHIIC-UHFFFAOYSA-N 4-[5-(3,5-dichloro-4-methoxyphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(OC)=C(Cl)C=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 FRACLAJOOXHIIC-UHFFFAOYSA-N 0.000 claims description 4
- FDAUDEPTKJFWGY-UHFFFAOYSA-N 4-[5-(3-ethyl-4-methoxyphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=C(OC)C(CC)=CC(C=2N(N=C(C=2)C(F)(F)F)C=2C=CC(=CC=2)S(N)(=O)=O)=C1 FDAUDEPTKJFWGY-UHFFFAOYSA-N 0.000 claims description 4
- GETBJRSHOBBZKB-UHFFFAOYSA-N 4-[5-(3-fluoro-4-methoxyphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 GETBJRSHOBBZKB-UHFFFAOYSA-N 0.000 claims description 4
- NAWWYLUQZOLWBT-UHFFFAOYSA-N 4-[5-(4-methoxyphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 NAWWYLUQZOLWBT-UHFFFAOYSA-N 0.000 claims description 4
- DVWHCFFOQZQHTQ-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)phenyl]-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 DVWHCFFOQZQHTQ-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- AHTVFSVKWLEYMA-UHFFFAOYSA-N ethyl 2-cyano-3-[5-phenyl-1-(4-sulfamoylphenyl)pyrazol-3-yl]prop-2-enoate Chemical compound C=1C=C(S(N)(=O)=O)C=CC=1N1N=C(C=C(C(=O)OCC)C#N)C=C1C1=CC=CC=C1 AHTVFSVKWLEYMA-UHFFFAOYSA-N 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- TTZNQDOUNXBMJV-UHFFFAOYSA-N mavacoxib Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(F)=CC=2)=CC(C(F)(F)F)=N1 TTZNQDOUNXBMJV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- MPHUNBLFEKLVLF-UHFFFAOYSA-N 4-[3-(difluoromethyl)-5-(4-methylphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 MPHUNBLFEKLVLF-UHFFFAOYSA-N 0.000 claims description 3
- FMTOVRQULOLSDM-UHFFFAOYSA-N 4-[5-(3-amino-4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=C(N)C(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 FMTOVRQULOLSDM-UHFFFAOYSA-N 0.000 claims description 3
- IYPAUZQRSAWCBH-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(hydroxymethyl)pyrazol-1-yl]benzenesulfonamide Chemical class C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(CO)=N1 IYPAUZQRSAWCBH-UHFFFAOYSA-N 0.000 claims description 3
- GEHUNGKNSFDUNT-UHFFFAOYSA-N 4-[5-[4-(methylamino)phenyl]-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(NC)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 GEHUNGKNSFDUNT-UHFFFAOYSA-N 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- YZEUTWRRPLTJON-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)-1-(4-sulfamoylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(S(N)(=O)=O)C=CC=1N1N=C(C(=O)OCC)C=C1C1=CC=C(Cl)C=C1 YZEUTWRRPLTJON-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- OYZKFVIVPRQRQQ-UHFFFAOYSA-N 1-phenylsulfonamide-3-trifluoromethyl-5-parabromophenylpyrazole Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Br)=CC=2)=CC(C(F)(F)F)=N1 OYZKFVIVPRQRQQ-UHFFFAOYSA-N 0.000 claims description 2
- VGVIEZJKAURHMU-UHFFFAOYSA-N 4-(3-cyano-5-phenylpyrazol-1-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=CC(C#N)=N1 VGVIEZJKAURHMU-UHFFFAOYSA-N 0.000 claims description 2
- WEZAMBRJDZBTFD-UHFFFAOYSA-N 4-(4-bromo-3-cyano-5-phenylpyrazol-1-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=C(Br)C(C#N)=N1 WEZAMBRJDZBTFD-UHFFFAOYSA-N 0.000 claims description 2
- DTLUCZWMHFLYLP-UHFFFAOYSA-N 4-(4-chloro-3-cyano-5-phenylpyrazol-1-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=C(Cl)C(C#N)=N1 DTLUCZWMHFLYLP-UHFFFAOYSA-N 0.000 claims description 2
- JAKUSVQKFVDBEC-UHFFFAOYSA-N 4-(4-chloro-3-methyl-5-phenylpyrazol-1-yl)benzenesulfonamide Chemical compound ClC=1C(C)=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C=1C1=CC=CC=C1 JAKUSVQKFVDBEC-UHFFFAOYSA-N 0.000 claims description 2
- ASSIMMUUPKWALS-UHFFFAOYSA-N 4-(4-chloro-5-phenyl-3-propan-2-ylpyrazol-1-yl)benzenesulfonamide Chemical compound ClC=1C(C(C)C)=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C=1C1=CC=CC=C1 ASSIMMUUPKWALS-UHFFFAOYSA-N 0.000 claims description 2
- UTAMLNUWNIAVPF-UHFFFAOYSA-N 4-[3-(difluoromethyl)-5-(2-fluoro-4-methoxyphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound FC1=CC(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 UTAMLNUWNIAVPF-UHFFFAOYSA-N 0.000 claims description 2
- SWQKKJIXYSKEFA-UHFFFAOYSA-N 4-[3-(difluoromethyl)-5-(2-methoxyphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 SWQKKJIXYSKEFA-UHFFFAOYSA-N 0.000 claims description 2
- CTNFCWNXUCDANF-UHFFFAOYSA-N 4-[3-(difluoromethyl)-5-(3,4-dimethoxyphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 CTNFCWNXUCDANF-UHFFFAOYSA-N 0.000 claims description 2
- LEMZOAJNWONTGE-UHFFFAOYSA-N 4-[3-(difluoromethyl)-5-(4-methylsulfanylphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(SC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 LEMZOAJNWONTGE-UHFFFAOYSA-N 0.000 claims description 2
- WQKRRUDWJUIGNO-UHFFFAOYSA-N 4-[3-(difluoromethyl)-5-(4-methylsulfonylphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 WQKRRUDWJUIGNO-UHFFFAOYSA-N 0.000 claims description 2
- QHWWEXGUDGYPKK-UHFFFAOYSA-N 4-[3-[chloro(difluoro)methyl]-5-(3-fluoro-4-methoxyphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)(F)Cl)=NN1C1=CC=C(S(N)(=O)=O)C=C1 QHWWEXGUDGYPKK-UHFFFAOYSA-N 0.000 claims description 2
- QXNBVNWBOSRLNB-UHFFFAOYSA-N 4-[3-cyano-5-(4-methoxyphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CC(C#N)=NN1C1=CC=C(S(N)(=O)=O)C=C1 QXNBVNWBOSRLNB-UHFFFAOYSA-N 0.000 claims description 2
- LKWYTUBTXYQQRD-UHFFFAOYSA-N 4-[3-cyano-5-(4-methylphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1=CC(C#N)=NN1C1=CC=C(S(N)(=O)=O)C=C1 LKWYTUBTXYQQRD-UHFFFAOYSA-N 0.000 claims description 2
- YLMCFMMBDTVYOA-UHFFFAOYSA-N 4-[3-cyano-5-(4-methylsulfanylphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(SC)=CC=C1C1=CC(C#N)=NN1C1=CC=C(S(N)(=O)=O)C=C1 YLMCFMMBDTVYOA-UHFFFAOYSA-N 0.000 claims description 2
- WCWCVJNCKAHYGP-UHFFFAOYSA-N 4-[4-bromo-3-(difluoromethyl)-5-phenylpyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=C(Br)C(C(F)F)=N1 WCWCVJNCKAHYGP-UHFFFAOYSA-N 0.000 claims description 2
- XIOMLJYZWRLNTF-UHFFFAOYSA-N 4-[4-bromo-3-cyano-5-(4-fluorophenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(F)=CC=2)=C(Br)C(C#N)=N1 XIOMLJYZWRLNTF-UHFFFAOYSA-N 0.000 claims description 2
- ZCLOGDSVOHZDJS-UHFFFAOYSA-N 4-[4-bromo-5-(4-chlorophenyl)-3-(difluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=C(Br)C(C(F)F)=N1 ZCLOGDSVOHZDJS-UHFFFAOYSA-N 0.000 claims description 2
- YVAOFGAOVRXLLB-UHFFFAOYSA-N 4-[4-bromo-5-(4-chlorophenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=C(Br)C=N1 YVAOFGAOVRXLLB-UHFFFAOYSA-N 0.000 claims description 2
- YBVOKLOWYVTUOL-UHFFFAOYSA-N 4-[4-bromo-5-(4-methoxyphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=C(Br)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 YBVOKLOWYVTUOL-UHFFFAOYSA-N 0.000 claims description 2
- KDZPEBLCIRAUOO-UHFFFAOYSA-N 4-[4-bromo-5-(4-methylphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1=C(Br)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 KDZPEBLCIRAUOO-UHFFFAOYSA-N 0.000 claims description 2
- CSSBQRDEAAZIHX-UHFFFAOYSA-N 4-[4-chloro-3-(difluoromethyl)-5-(4-methoxyphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=C(Cl)C(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 CSSBQRDEAAZIHX-UHFFFAOYSA-N 0.000 claims description 2
- SVGPESKYJCFQLM-UHFFFAOYSA-N 4-[4-chloro-3-(difluoromethyl)-5-phenylpyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=C(Cl)C(C(F)F)=N1 SVGPESKYJCFQLM-UHFFFAOYSA-N 0.000 claims description 2
- ODPAVZZSCREHOA-UHFFFAOYSA-N 4-[4-chloro-3-(hydroxymethyl)-5-phenylpyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=C(Cl)C(CO)=N1 ODPAVZZSCREHOA-UHFFFAOYSA-N 0.000 claims description 2
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- HKMLRUAPIDAGIE-UHFFFAOYSA-N methyl 2,2-dichloroacetate Chemical compound COC(=O)C(Cl)Cl HKMLRUAPIDAGIE-UHFFFAOYSA-N 0.000 description 1
- AQYAHPDSJAFBOS-UHFFFAOYSA-N methyl 2,4-dioxo-4-phenylbutanoate Chemical compound COC(=O)C(=O)CC(=O)C1=CC=CC=C1 AQYAHPDSJAFBOS-UHFFFAOYSA-N 0.000 description 1
- AWUPLMYXZJKHEG-UHFFFAOYSA-N methyl 2-chloro-2,2-difluoroacetate Chemical compound COC(=O)C(F)(F)Cl AWUPLMYXZJKHEG-UHFFFAOYSA-N 0.000 description 1
- YHUDIBFBJQONAZ-UHFFFAOYSA-N methyl 3-[5-(4-fluorophenyl)-1-(4-sulfamoylphenyl)pyrazol-3-yl]propanoate Chemical compound C=1C=C(S(N)(=O)=O)C=CC=1N1N=C(CCC(=O)OC)C=C1C1=CC=C(F)C=C1 YHUDIBFBJQONAZ-UHFFFAOYSA-N 0.000 description 1
- FJWAJGTYVMQLHP-UHFFFAOYSA-N methyl 4-(2-fluorophenyl)-2,4-dioxobutanoate Chemical compound COC(=O)C(=O)CC(=O)C1=CC=CC=C1F FJWAJGTYVMQLHP-UHFFFAOYSA-N 0.000 description 1
- MDZLFGRBIDLTTH-UHFFFAOYSA-N methyl 4-(3,5-difluoro-4-methoxyphenyl)-2,4-dioxobutanoate Chemical compound COC(=O)C(=O)CC(=O)C1=CC(F)=C(OC)C(F)=C1 MDZLFGRBIDLTTH-UHFFFAOYSA-N 0.000 description 1
- AUACEYSPFQLYBF-UHFFFAOYSA-N methyl 4-[2-(4-sulfamoylphenyl)-5-(trifluoromethyl)pyrazol-3-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 AUACEYSPFQLYBF-UHFFFAOYSA-N 0.000 description 1
- DKIIWBXOGYWLLV-UHFFFAOYSA-N methyl 4-[5-(difluoromethyl)-2-(4-sulfamoylphenyl)pyrazol-3-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 DKIIWBXOGYWLLV-UHFFFAOYSA-N 0.000 description 1
- BJDGUZGBQQSADR-UHFFFAOYSA-N methyl 5-(3,5-dichloro-4-methoxyphenyl)-1-(4-sulfamoylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(S(N)(=O)=O)C=CC=1N1N=C(C(=O)OC)C=C1C1=CC(Cl)=C(OC)C(Cl)=C1 BJDGUZGBQQSADR-UHFFFAOYSA-N 0.000 description 1
- LYRWIDGNODHWSW-UHFFFAOYSA-N methyl 5-(3,5-difluoro-4-methoxyphenyl)-1-(4-sulfamoylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(S(N)(=O)=O)C=CC=1N1N=C(C(=O)OC)C=C1C1=CC(F)=C(OC)C(F)=C1 LYRWIDGNODHWSW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US08/160,594 US5466823A (en) | 1993-11-30 | 1993-11-30 | Substituted pyrazolyl benzenesulfonamides |
US08/223,629 US5521207A (en) | 1993-11-30 | 1994-04-06 | Substituted pyrazolyl benzenesulfonamide for the treatment of inflammation |
PCT/US1994/012720 WO1995015316A1 (en) | 1993-11-30 | 1994-11-14 | Substituted pyrazolyl benzenesulfonamides for the treatment of inflammation |
Publications (2)
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DE69422306T2 DE69422306T2 (de) | 2000-05-18 |
DE69422306T4 true DE69422306T4 (de) | 2000-09-07 |
Family
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DE69430930T Expired - Lifetime DE69430930T2 (de) | 1993-11-30 | 1994-11-14 | Substitutierte Pyrazolyl-Benzolsulfonamide zur Verwendung in der Behandlung von Entzündungen |
DE2000175033 Active DE10075033I2 (de) | 1993-11-30 | 1994-11-14 | substituierte Pyrazolyl-benzolsulfonamide zur Behandlung von Entzündungen. |
DE69432193T Expired - Lifetime DE69432193T2 (de) | 1993-11-30 | 1994-11-14 | Substituierte Pyrazolyl-benzolsulfonamide und ihre Verwendung als CyclooxygenaseII Inhibitoren |
DE69422306T Expired - Lifetime DE69422306T4 (de) | 1993-11-30 | 1994-11-14 | Substituierte pyrazolyl-benzolsulfonamide zur behandlung von entzündungen |
DE69422306A Expired - Lifetime DE69422306D1 (de) | 1993-11-30 | 1994-11-14 | Substituierte pyrazolyl-benzolsulfonamide zur behandlung von entzündungen |
DE69429836T Expired - Lifetime DE69429836T2 (de) | 1993-11-30 | 1994-11-14 | Tricyclische,substituierte Pyrazolyl- benzolsulfonamide und ihre Verwendung als Cyclooxygenase II Inhibitoren |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
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DE69430930T Expired - Lifetime DE69430930T2 (de) | 1993-11-30 | 1994-11-14 | Substitutierte Pyrazolyl-Benzolsulfonamide zur Verwendung in der Behandlung von Entzündungen |
DE2000175033 Active DE10075033I2 (de) | 1993-11-30 | 1994-11-14 | substituierte Pyrazolyl-benzolsulfonamide zur Behandlung von Entzündungen. |
DE69432193T Expired - Lifetime DE69432193T2 (de) | 1993-11-30 | 1994-11-14 | Substituierte Pyrazolyl-benzolsulfonamide und ihre Verwendung als CyclooxygenaseII Inhibitoren |
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Application Number | Title | Priority Date | Filing Date |
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DE69422306A Expired - Lifetime DE69422306D1 (de) | 1993-11-30 | 1994-11-14 | Substituierte pyrazolyl-benzolsulfonamide zur behandlung von entzündungen |
DE69429836T Expired - Lifetime DE69429836T2 (de) | 1993-11-30 | 1994-11-14 | Tricyclische,substituierte Pyrazolyl- benzolsulfonamide und ihre Verwendung als Cyclooxygenase II Inhibitoren |
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US4146721A (en) * | 1969-09-12 | 1979-03-27 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Pyrazol-4-acetic acid compounds |
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 |
DE2536003C2 (de) * | 1975-08-08 | 1985-11-14 | Schering AG, 1000 Berlin und 4709 Bergkamen | Pyrazol-Derivate, ihre Herstellung und diese enthaltende pharmazeutische Derivate |
US4826868A (en) * | 1986-05-29 | 1989-05-02 | Ortho Pharmaceutical Corporation | 1,5-Diaryl-3-substituted pyrazoles pharmaceutical compositions and use |
GB8814587D0 (en) * | 1988-06-20 | 1988-07-27 | Erba Carlo Spa | Condensed pyrazole 3-oxo-propanenitrile derivatives & process for their preparation |
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FR2665898B1 (fr) * | 1990-08-20 | 1994-03-11 | Sanofi | Derives d'amido-3 pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
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1994
- 1994-11-14 PT PT95902444T patent/PT731795E/pt unknown
- 1994-11-14 CZ CZ19961503A patent/CZ294630B6/cs not_active IP Right Cessation
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- 1994-11-14 DK DK99101677T patent/DK0924201T3/da active
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- 1994-11-14 PL PL94314695A patent/PL180717B1/pl unknown
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- 1994-11-14 CA CA002277954A patent/CA2277954A1/en not_active Abandoned
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- 1994-11-14 HU HU9601455A patent/HU223824B1/hu active Protection Beyond IP Right Term
- 1994-11-14 CA CA002276946A patent/CA2276946A1/en not_active Abandoned
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- 1994-11-14 DK DK95902444T patent/DK0731795T3/da active
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- 1994-11-14 DK DK99101697T patent/DK0923933T3/da active
- 1994-11-14 DE DE2000175033 patent/DE10075033I2/de active Active
- 1994-11-14 DE DE69432193T patent/DE69432193T2/de not_active Expired - Lifetime
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- 1994-11-14 ES ES99101677T patent/ES2172959T3/es not_active Expired - Lifetime
- 1994-11-14 CN CNB2003101142478A patent/CN1268614C/zh not_active Expired - Lifetime
- 1994-11-14 CN CN94194833A patent/CN1061036C/zh not_active Expired - Lifetime
- 1994-11-14 US US08/648,113 patent/US5760068A/en not_active Ceased
- 1994-11-14 NZ NZ336428A patent/NZ336428A/en not_active IP Right Cessation
- 1994-11-14 DE DE69422306T patent/DE69422306T4/de not_active Expired - Lifetime
- 1994-11-14 AT AT99101697T patent/ATE219937T1/de active
- 1994-11-14 DE DE69422306A patent/DE69422306D1/de not_active Expired - Lifetime
- 1994-11-14 RU RU96115039A patent/RU2139281C1/ru active
- 1994-11-14 PT PT99101697T patent/PT923933E/pt unknown
- 1994-11-14 RO RO96-01100A patent/RO118291B1/ro unknown
- 1994-11-14 AT AT95902444T patent/ATE187965T1/de active
- 1994-11-14 AT AT99101677T patent/ATE212985T1/de active
- 1994-11-14 WO PCT/US1994/012720 patent/WO1995015316A1/en active Search and Examination
- 1994-11-14 DE DE69429836T patent/DE69429836T2/de not_active Expired - Lifetime
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1995
- 1995-09-27 US US08/534,757 patent/US5753688A/en not_active Expired - Lifetime
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1996
- 1996-05-29 FI FI962249A patent/FI115053B/fi not_active IP Right Cessation
- 1996-05-29 NO NO962184A patent/NO306460B1/no not_active IP Right Cessation
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1999
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2000
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- 2000-12-13 LU LU90698C patent/LU90698I2/fr unknown
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2001
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2003
- 2003-01-06 JP JP2003032958A patent/JP3921451B2/ja not_active Expired - Lifetime
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2009
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