JP2004525166A5 - - Google Patents
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- JP2004525166A5 JP2004525166A5 JP2002578948A JP2002578948A JP2004525166A5 JP 2004525166 A5 JP2004525166 A5 JP 2004525166A5 JP 2002578948 A JP2002578948 A JP 2002578948A JP 2002578948 A JP2002578948 A JP 2002578948A JP 2004525166 A5 JP2004525166 A5 JP 2004525166A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazole
- dihydro
- trifluoromethyl
- aminosulfonylphenyl
- group
- 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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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- 229910052731 fluorine Inorganic materials 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 7
- -1 acetylaminosulfonyl group Chemical group 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 7
- 102000010907 Cyclooxygenase 2 Human genes 0.000 claims 6
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 6
- 230000001575 pathological Effects 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000011780 sodium chloride Substances 0.000 claims 6
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 5
- 108010001801 Tumor Necrosis Factor-alpha Proteins 0.000 claims 5
- 230000015572 biosynthetic process Effects 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 230000002062 proliferating Effects 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- NUUXNKLZACNVSR-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C(=CC(F)=CC=2)F)N=C(C(F)(F)F)C1 NUUXNKLZACNVSR-UHFFFAOYSA-N 0.000 claims 3
- DXANXCBCSPZANW-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C=CC(F)=CC=2)N=C(C(F)(F)F)C1 DXANXCBCSPZANW-UHFFFAOYSA-N 0.000 claims 3
- ZZMJXWXXMAAPLI-UHFFFAOYSA-N 4-[3-(2,4-difluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC(F)=CC=2)F)CC(C(F)(F)F)=N1 ZZMJXWXXMAAPLI-UHFFFAOYSA-N 0.000 claims 3
- 206010006895 Cachexia Diseases 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 230000033115 angiogenesis Effects 0.000 claims 3
- 230000014509 gene expression Effects 0.000 claims 3
- 150000003219 pyrazolines Chemical class 0.000 claims 3
- 230000001629 suppression Effects 0.000 claims 3
- 238000003786 synthesis reaction Methods 0.000 claims 3
- 230000002194 synthesizing Effects 0.000 claims 3
- QDJRZKJPHCZNDT-UHFFFAOYSA-N 3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-2-[2-(trifluoromethyl)phenyl]-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C(=CC=CC=2)C(F)(F)F)N=C(C(F)(F)F)C1 QDJRZKJPHCZNDT-UHFFFAOYSA-N 0.000 claims 2
- 238000005755 formation reaction Methods 0.000 claims 2
- 230000001613 neoplastic Effects 0.000 claims 2
- 230000003449 preventive Effects 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- FTMOPUYNYHRMFN-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C(=CC(Cl)=CC=2)Cl)N=C(C(F)(F)F)C1 FTMOPUYNYHRMFN-UHFFFAOYSA-N 0.000 claims 1
- WYTGCYYFONATBA-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound CC1=CC(C)=CC=C1N1C(C=2C=CC(=CC=2)S(C)(=O)=O)CC(C(F)(F)F)=N1 WYTGCYYFONATBA-UHFFFAOYSA-N 0.000 claims 1
- HSHVCHZVLHORQM-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C(=CC=CC=2)Cl)N=C(C(F)(F)F)C1 HSHVCHZVLHORQM-UHFFFAOYSA-N 0.000 claims 1
- DMMVWGZOGYNMGY-UHFFFAOYSA-N 2-(2-fluorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C(=CC=CC=2)F)N=C(C(F)(F)F)C1 DMMVWGZOGYNMGY-UHFFFAOYSA-N 0.000 claims 1
- CPYSYVKZVKFTHJ-UHFFFAOYSA-N 2-(2-methylphenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound CC1=CC=CC=C1N1C(C=2C=CC(=CC=2)S(C)(=O)=O)CC(C(F)(F)F)=N1 CPYSYVKZVKFTHJ-UHFFFAOYSA-N 0.000 claims 1
- JWBPVMWEHROJMV-UHFFFAOYSA-N 2-(3-fluorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C=C(F)C=CC=2)N=C(C(F)(F)F)C1 JWBPVMWEHROJMV-UHFFFAOYSA-N 0.000 claims 1
- SWAUQQYFPQVQSJ-UHFFFAOYSA-N 2-(3-methylphenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound CC1=CC=CC(N2C(CC(=N2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 SWAUQQYFPQVQSJ-UHFFFAOYSA-N 0.000 claims 1
- RTHYHPLQWLNMPZ-UHFFFAOYSA-N 2-(4-chloro-2-methylphenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound CC1=CC(Cl)=CC=C1N1C(C=2C=CC(=CC=2)S(C)(=O)=O)CC(C(F)(F)F)=N1 RTHYHPLQWLNMPZ-UHFFFAOYSA-N 0.000 claims 1
- JBRFWCGJQZUHBW-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C=CC(Cl)=CC=2)N=C(C(F)(F)F)C1 JBRFWCGJQZUHBW-UHFFFAOYSA-N 0.000 claims 1
- KYDWPNBHFLBRIS-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C=CC(F)=CC=2)N=CC1 KYDWPNBHFLBRIS-UHFFFAOYSA-N 0.000 claims 1
- BQMJBDAPQSEBHC-UHFFFAOYSA-N 2-(4-methylphenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(C)=CC=C1N1C(C=2C=CC(=CC=2)S(C)(=O)=O)CC(C(F)(F)F)=N1 BQMJBDAPQSEBHC-UHFFFAOYSA-N 0.000 claims 1
- XLGPMIWEYLAQAN-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-3-phenyl-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC=CC=2)CC=N1 XLGPMIWEYLAQAN-UHFFFAOYSA-N 0.000 claims 1
- ICDOEQFGMOCZMV-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-3-phenyl-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC=CC=2)CC(C(F)(F)F)=N1 ICDOEQFGMOCZMV-UHFFFAOYSA-N 0.000 claims 1
- MYEDBOXTBGKCOU-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-2-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)CC(C(F)(F)F)=N1 MYEDBOXTBGKCOU-UHFFFAOYSA-N 0.000 claims 1
- FRQSGXCNDIYEIH-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C(=CC=CC=2)F)CC(C(F)(F)F)=N1 FRQSGXCNDIYEIH-UHFFFAOYSA-N 0.000 claims 1
- JGJAPXOXMKQZFJ-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-2-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=C(F)C(F)=CC=2)CC(C(F)(F)F)=N1 JGJAPXOXMKQZFJ-UHFFFAOYSA-N 0.000 claims 1
- UCLTWOHUTQRYOX-UHFFFAOYSA-N 3-(3-fluorophenyl)-2-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=C(F)C=CC=2)CC(C(F)(F)F)=N1 UCLTWOHUTQRYOX-UHFFFAOYSA-N 0.000 claims 1
- SCPUBMXALQFIJC-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(F)=CC=2)CC(C(F)(F)F)=N1 SCPUBMXALQFIJC-UHFFFAOYSA-N 0.000 claims 1
- WGTRCKXLJLADDX-UHFFFAOYSA-N 3-(4-fluorophenyl)-5-methyl-2-(4-methylsulfonylphenyl)-3,4-dihydropyrazole Chemical compound C1C(C)=NN(C=2C=CC(=CC=2)S(C)(=O)=O)C1C1=CC=C(F)C=C1 WGTRCKXLJLADDX-UHFFFAOYSA-N 0.000 claims 1
- HFHHSMJIOSROMS-UHFFFAOYSA-N 3-(4-methylphenyl)-2-(4-methylsulfonylphenyl)-3,4-dihydropyrazole-5-carbonitrile Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(C)(=O)=O)N=C(C#N)C1 HFHHSMJIOSROMS-UHFFFAOYSA-N 0.000 claims 1
- PMLQIOBJCLELTH-UHFFFAOYSA-N 3-(4-methylphenyl)-2-(4-methylsulfonylphenyl)-3,4-dihydropyrazole-5-carboxamide Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(C)(=O)=O)N=C(C(N)=O)C1 PMLQIOBJCLELTH-UHFFFAOYSA-N 0.000 claims 1
- SJBQRYJKBSPTKG-UHFFFAOYSA-M 3-(4-methylphenyl)-2-(4-methylsulfonylphenyl)-3,4-dihydropyrazole-5-carboxylate Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(C)(=O)=O)N=C(C([O-])=O)C1 SJBQRYJKBSPTKG-UHFFFAOYSA-M 0.000 claims 1
- SJBQRYJKBSPTKG-UHFFFAOYSA-N 3-(4-methylphenyl)-2-(4-methylsulfonylphenyl)-3,4-dihydropyrazole-5-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(C)(=O)=O)N=C(C(O)=O)C1 SJBQRYJKBSPTKG-UHFFFAOYSA-N 0.000 claims 1
- DUWSUJBWSUSJSF-UHFFFAOYSA-N 3-(4-methylphenyl)-2-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(C)(=O)=O)N=C(C(F)(F)F)C1 DUWSUJBWSUSJSF-UHFFFAOYSA-N 0.000 claims 1
- ACXXZWIJKRQJLQ-UHFFFAOYSA-N 3-(4-methylphenyl)-2-(4-sulfamoylphenyl)-3,4-dihydropyrazole-5-carboxamide Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(N)=O)C1 ACXXZWIJKRQJLQ-UHFFFAOYSA-N 0.000 claims 1
- YACZNKGYISHAOT-UHFFFAOYSA-M 3-(4-methylphenyl)-2-(4-sulfamoylphenyl)-3,4-dihydropyrazole-5-carboxylate Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C([O-])=O)C1 YACZNKGYISHAOT-UHFFFAOYSA-M 0.000 claims 1
- YACZNKGYISHAOT-UHFFFAOYSA-N 3-(4-methylphenyl)-2-(4-sulfamoylphenyl)-3,4-dihydropyrazole-5-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(O)=O)C1 YACZNKGYISHAOT-UHFFFAOYSA-N 0.000 claims 1
- SALWHXXPZFQWIF-UHFFFAOYSA-N 3-(4-methylsulfonylphenyl)-2-phenyl-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C=CC=CC=2)N=C(C(F)(F)F)C1 SALWHXXPZFQWIF-UHFFFAOYSA-N 0.000 claims 1
- SCJYUURHLNBEIH-UHFFFAOYSA-N 3-phenyl-2-(4-sulfamoylphenyl)-3,4-dihydropyrazole-5-carboxamide Chemical compound C1C(C(=O)N)=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C1C1=CC=CC=C1 SCJYUURHLNBEIH-UHFFFAOYSA-N 0.000 claims 1
- ZWPZGFZPOQCGAA-UHFFFAOYSA-M 3-phenyl-2-(4-sulfamoylphenyl)-3,4-dihydropyrazole-5-carboxylate Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)CC(C([O-])=O)=N1 ZWPZGFZPOQCGAA-UHFFFAOYSA-M 0.000 claims 1
- ZWPZGFZPOQCGAA-UHFFFAOYSA-N 3-phenyl-2-(4-sulfamoylphenyl)-3,4-dihydropyrazole-5-carboxylic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)CC(C(O)=O)=N1 ZWPZGFZPOQCGAA-UHFFFAOYSA-N 0.000 claims 1
- NADGCWXUHBRQPK-UHFFFAOYSA-N 4-(3-phenyl-3,4-dihydropyrazol-2-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)CC=N1 NADGCWXUHBRQPK-UHFFFAOYSA-N 0.000 claims 1
- VKKYVYAAEHCIQR-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-3-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1N(C=2C=CC(F)=CC=2)N=C(C(F)(F)F)C1 VKKYVYAAEHCIQR-UHFFFAOYSA-N 0.000 claims 1
- VTYPWKRHGVKCAN-UHFFFAOYSA-N 4-[3-(2,3-difluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=C(F)C=CC=2)F)CC(C(F)(F)F)=N1 VTYPWKRHGVKCAN-UHFFFAOYSA-N 0.000 claims 1
- WXELPGWWHJCPHS-UHFFFAOYSA-N 4-[3-(2,4-dichlorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)CC(C(F)(F)F)=N1 WXELPGWWHJCPHS-UHFFFAOYSA-N 0.000 claims 1
- JQBARVBPEJYKGP-UHFFFAOYSA-N 4-[3-(2,4-dimethoxyphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound COC1=CC(OC)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 JQBARVBPEJYKGP-UHFFFAOYSA-N 0.000 claims 1
- HTDDWURRXIGACU-UHFFFAOYSA-N 4-[3-(2,4-dimethylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 HTDDWURRXIGACU-UHFFFAOYSA-N 0.000 claims 1
- HZNMOTSUIFCOCF-UHFFFAOYSA-N 4-[3-(2-chloro-4-fluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC(F)=CC=2)Cl)CC(C(F)(F)F)=N1 HZNMOTSUIFCOCF-UHFFFAOYSA-N 0.000 claims 1
- JSKIKBFERIDANX-UHFFFAOYSA-N 4-[3-(2-chlorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC=CC=2)Cl)CC(C(F)(F)F)=N1 JSKIKBFERIDANX-UHFFFAOYSA-N 0.000 claims 1
- SLSINBTZGDBROZ-UHFFFAOYSA-N 4-[3-(2-fluoro-4-methoxyphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound FC1=CC(OC)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 SLSINBTZGDBROZ-UHFFFAOYSA-N 0.000 claims 1
- GGIFCPPVQVEHCG-UHFFFAOYSA-N 4-[3-(2-fluoro-4-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound FC1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 GGIFCPPVQVEHCG-UHFFFAOYSA-N 0.000 claims 1
- ASUHJSUSKBNECS-UHFFFAOYSA-N 4-[3-(2-fluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC=CC=2)F)CC(C(F)(F)F)=N1 ASUHJSUSKBNECS-UHFFFAOYSA-N 0.000 claims 1
- FUKIEVBHHBTNDY-UHFFFAOYSA-N 4-[3-(2-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound CC1=CC=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 FUKIEVBHHBTNDY-UHFFFAOYSA-N 0.000 claims 1
- FFZJOJGVAOJVOA-UHFFFAOYSA-N 4-[3-(3,4-difluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=C(F)C(F)=CC=2)CC(C(F)(F)F)=N1 FFZJOJGVAOJVOA-UHFFFAOYSA-N 0.000 claims 1
- INCZYKUDDWCUDZ-UHFFFAOYSA-N 4-[3-(3,4-dimethylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=C(C)C(C)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 INCZYKUDDWCUDZ-UHFFFAOYSA-N 0.000 claims 1
- UXMSSKLTDLLVKZ-UHFFFAOYSA-N 4-[3-(3-chloro-4-fluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=C(Cl)C(F)=CC=2)CC(C(F)(F)F)=N1 UXMSSKLTDLLVKZ-UHFFFAOYSA-N 0.000 claims 1
- JKMVJKYQBPOCDY-UHFFFAOYSA-N 4-[3-(3-fluoro-2-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound CC1=C(F)C=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 JKMVJKYQBPOCDY-UHFFFAOYSA-N 0.000 claims 1
- SEEZUXWJFQKHJH-UHFFFAOYSA-N 4-[3-(3-fluoro-4-methoxyphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 SEEZUXWJFQKHJH-UHFFFAOYSA-N 0.000 claims 1
- WWTIGFLZKWDAKZ-UHFFFAOYSA-N 4-[3-(3-fluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=C(F)C=CC=2)CC(C(F)(F)F)=N1 WWTIGFLZKWDAKZ-UHFFFAOYSA-N 0.000 claims 1
- DASSSRCBIOPSDJ-UHFFFAOYSA-N 4-[3-(3-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound CC1=CC=CC(C2N(N=C(C2)C(F)(F)F)C=2C=CC(=CC=2)S(N)(=O)=O)=C1 DASSSRCBIOPSDJ-UHFFFAOYSA-N 0.000 claims 1
- AXMQEIGLBBEBIR-UHFFFAOYSA-N 4-[3-(4-chloro-2-fluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)F)CC(C(F)(F)F)=N1 AXMQEIGLBBEBIR-UHFFFAOYSA-N 0.000 claims 1
- DGRJCTLVHASBJO-UHFFFAOYSA-N 4-[3-(4-fluoro-2-methoxyphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound COC1=CC(F)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 DGRJCTLVHASBJO-UHFFFAOYSA-N 0.000 claims 1
- FBBVAAMIUGCGKM-UHFFFAOYSA-N 4-[3-(4-fluoro-2-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(F)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 FBBVAAMIUGCGKM-UHFFFAOYSA-N 0.000 claims 1
- NEVHKLLTWKFJOF-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(F)=CC=2)CC(C(F)(F)F)=N1 NEVHKLLTWKFJOF-UHFFFAOYSA-N 0.000 claims 1
- RZJICADINWJPMA-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-5-methyl-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1C(C)=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C1C1=CC=C(F)C=C1 RZJICADINWJPMA-UHFFFAOYSA-N 0.000 claims 1
- QAPXFHIPWJILOM-UHFFFAOYSA-N 4-[3-(4-methoxy-2-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(OC)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 QAPXFHIPWJILOM-UHFFFAOYSA-N 0.000 claims 1
- VBHSLDFADJEMET-UHFFFAOYSA-N 4-[3-(4-methoxy-3-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=C(C)C(OC)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 VBHSLDFADJEMET-UHFFFAOYSA-N 0.000 claims 1
- BSYNCTSOUUMGKG-UHFFFAOYSA-N 4-[3-(4-methoxyphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 BSYNCTSOUUMGKG-UHFFFAOYSA-N 0.000 claims 1
- MQKGKXATGINIDF-UHFFFAOYSA-N 4-[3-(4-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 MQKGKXATGINIDF-UHFFFAOYSA-N 0.000 claims 1
- VEMICYBXEGHMIY-UHFFFAOYSA-N 4-[3-[2-fluoro-4-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC(=CC=2)C(F)(F)F)F)CC(C(F)(F)F)=N1 VEMICYBXEGHMIY-UHFFFAOYSA-N 0.000 claims 1
- IFRATYFQLPOODQ-UHFFFAOYSA-N 4-[3-[4-(trifluoromethoxy)phenyl]-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(OC(F)(F)F)=CC=2)CC(C(F)(F)F)=N1 IFRATYFQLPOODQ-UHFFFAOYSA-N 0.000 claims 1
- RWIGCNOMEIOVFW-UHFFFAOYSA-N 4-[3-[4-fluoro-2-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC(F)=CC=2)C(F)(F)F)CC(C(F)(F)F)=N1 RWIGCNOMEIOVFW-UHFFFAOYSA-N 0.000 claims 1
- XFLCCCUNVGNSHZ-UHFFFAOYSA-N 4-[3-phenyl-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)CC(C(F)(F)F)=N1 XFLCCCUNVGNSHZ-UHFFFAOYSA-N 0.000 claims 1
- SEMBZXOXJZAKEY-UHFFFAOYSA-N 4-[5-(difluoromethyl)-3-(2,4-difluorophenyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC(F)=CC=2)F)CC(C(F)F)=N1 SEMBZXOXJZAKEY-UHFFFAOYSA-N 0.000 claims 1
- VVXNPWRDLOBWRE-UHFFFAOYSA-N 4-[5-(difluoromethyl)-3-(2,4-dimethylphenyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)F)C1 VVXNPWRDLOBWRE-UHFFFAOYSA-N 0.000 claims 1
- HFMFBVYFNNETMN-UHFFFAOYSA-N 4-[5-(trifluoromethyl)-3-(2,3,4-trifluorophenyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=C(F)C(F)=CC=2)F)CC(C(F)(F)F)=N1 HFMFBVYFNNETMN-UHFFFAOYSA-N 0.000 claims 1
- NJHCSSOPPPFIQV-UHFFFAOYSA-N 4-[5-methyl-3-(4-methylphenyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1C(C)=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C1C1=CC=C(C)C=C1 NJHCSSOPPPFIQV-UHFFFAOYSA-N 0.000 claims 1
- XMRZZVGLGSTXFW-UHFFFAOYSA-N 4-[5-methyl-3-[4-(trifluoromethyl)phenyl]-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1C(C)=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C1C1=CC=C(C(F)(F)F)C=C1 XMRZZVGLGSTXFW-UHFFFAOYSA-N 0.000 claims 1
- FQFJVLUVKRGNPQ-UHFFFAOYSA-N 4-[5-methyl-5-phenyl-3-(trifluoromethyl)-4H-pyrazol-1-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1C1(C)CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 FQFJVLUVKRGNPQ-UHFFFAOYSA-N 0.000 claims 1
- NYHPBHAHZFULOT-UHFFFAOYSA-N 5-methyl-2-(4-methylsulfonylphenyl)-3-[4-(trifluoromethyl)phenyl]-3,4-dihydropyrazole Chemical compound C1C(C)=NN(C=2C=CC(=CC=2)S(C)(=O)=O)C1C1=CC=C(C(F)(F)F)C=C1 NYHPBHAHZFULOT-UHFFFAOYSA-N 0.000 claims 1
- VACFVFJHUPMIEL-UHFFFAOYSA-N 5-methyl-3-(4-methylphenyl)-2-(4-methylsulfonylphenyl)-3,4-dihydropyrazole Chemical compound C1C(C)=NN(C=2C=CC(=CC=2)S(C)(=O)=O)C1C1=CC=C(C)C=C1 VACFVFJHUPMIEL-UHFFFAOYSA-N 0.000 claims 1
- VMRBITBSIDDKSD-UHFFFAOYSA-N 5-methyl-3-(4-methylsulfonylphenyl)-2-phenyl-3,4-dihydropyrazole Chemical compound C1C(C)=NN(C=2C=CC=CC=2)C1C1=CC=C(S(C)(=O)=O)C=C1 VMRBITBSIDDKSD-UHFFFAOYSA-N 0.000 claims 1
- NCTYCSBNIWUFGY-UHFFFAOYSA-N N-[4-[3-(2,4-difluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1N1C(C=2C(=CC(F)=CC=2)F)CC(C(F)(F)F)=N1 NCTYCSBNIWUFGY-UHFFFAOYSA-N 0.000 claims 1
- 208000008636 Neoplastic Process Diseases 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 230000022534 cell killing Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 230000009089 cytolysis Effects 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 230000017074 necrotic cell death Effects 0.000 claims 1
- 230000001855 preneoplastic Effects 0.000 claims 1
- 230000002195 synergetic Effects 0.000 claims 1
Claims (3)
- 細胞増殖疾患の予防又は治療薬の調製におけるピラゾリン誘導体又はその生理的許容塩の使用であって、
前記ピラゾリン誘導体は次の一般構造式（Ｉ）で示され、
Ｒ１は、水素原子、メチル基、フルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、カルボキシル基、炭素数１〜４の低級アルコキシカルボニル基、カルバモイル基、又はシアノ基を示し、
Ｒ２は、水素原子又はメチル基を示し、
Ｒ３、Ｒ４、Ｒ７、及びＲ８はそれぞれ、水素原子、塩素原子、フッ素原子、メチル基、トリフルオロメチル基、又はメトキシ基を示し、
Ｒ５は、水素原子、塩素原子、フッ素原子、メチル基、トリフルオロメチル基、メトキシ基、トリフルオロメトキシ基、メチルスルホニル基、アミノスルホニル基、又はアセチルアミノスルホニル基を示し、
Ｒ６は、水素原子、塩素原子、フッ素原子、メチル基、トリフルオロメチル基、メトキシ基、トリフルオロメトキシ基、メチルスルホニル基、アミノスルホニル基、又はアセチルアミノスルホニル基を示すものであって、
置換基Ｒ５又はＲ６の一方は、メチルスルホニル基、アミノスルホニル基、又はアセチルアミノスルホニル基であり、
また、Ｒ１がメチル基を示す場合、
Ｒ２は、水素原子又はメチル基を示し、
Ｒ３及びＲ８はそれぞれ、水素原子、塩素原子、フッ素原子、メチル基、又はトリフルオロメチル基を示し、
Ｒ４は、水素原子、フッ素原子、メチル基、トリフルオロメチル基、又はメトキシ基を示し、
Ｒ５は、フッ素原子、トリフルオロメチル基、トリフルオロメトキシ基、メチルスルホニル基、アミノスルホニル基、又はアセチルアミノスルホニル基を示し、
Ｒ６は、水素原子、塩素原子、フッ素原子、メチル基、トリフルオロメチル基、メトキシ基、トリフルオロメトキシ基、メチルスルホニル基、アミノスルホニル基、又はアセチルアミノスルホニル基を示すものであって、
置換基Ｒ５又はＲ６の一方は、メチルスルホニル基、アミノスルホニル基、又はアセチルアミノスルホニル基であり、
Ｒ７は、水素原子、塩素原子、フッ素原子、メチル基、トリフルオロメチル基、又はメトキシ基を示すものであり、
前記ピラゾリン誘導体又はその生理的許容塩を、ヒトを含む哺乳動物における細胞増殖疾患の予防又は治療薬、より詳細には、新生物形成前又は新生物形成過程、腫瘍血管新生、悪液質、及び腫瘍壊死因子（ＴＮＦ）に関わる病的状態、また一般に、シクロオキシゲナーゼ−２（ＣＯＸ−２）合成の原因となる遺伝子の発現抑制により利益を受ける病的状態の予防又は治療薬の調製に使用することを特徴とする方法。 - 請求項１に記載の一般構造式（Ｉ）で示される化合物又はその生理的許容塩の使用であって、
前記化合物は、
［１］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（４−メチルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［２］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−メチル−５−フェニル−３−トリフルオロメチル−１Ｈ−ピラゾール、
［３］１−（４−アミノスルホニルフェニル）−５−（２，４−ジフルオロフェニル）−４，５−ジヒドロ−３−トリフルオロメチル−１Ｈ−ピラゾール、
［４］４，５−ジヒドロ−１−（４−メチルフェニル）−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［５］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−フェニル−３−トリフルオロメチル−１Ｈ−ピラゾール、
［６］４，５−ジヒドロ−５−フェニル−１−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［７］４，５−ジヒドロ−５−（４−メチルフェニル）−１−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［８］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（４−フルオロフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［９］４，５−ジヒドロ−５−（４−フルオロフェニル）−１−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［１０］４，５−ジヒドロ−１−（４−フルオロフェニル）−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［１１］１−（４−アミノスルホニルフェニル）−５−（３，４−ジフルオロフェニル）−４，５−ジヒドロ−３−トリフルオロメチル−１Ｈ−ピラゾール、
［１２］５−（２，４−ジクロロフェニル）−４，５−ジヒドロ−１−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［１３］１−（４−アミノスルホニルフェニル）−５−（２，４−ジクロロフェニル）−４，５−ジヒドロ−３−トリフルオロメチル−１Ｈ−ピラゾール、
［１４］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（２−メチルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［１５］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（３−メチルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［１６］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（２−フルオロフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［１７］４，５−ジヒドロ−５−（２−フルオロフェニル）−１−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［１８］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（３−フルオロフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［１９］４，５−ジヒドロ−５−（３−フルオロフェニル）−１−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［２０］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（４−メトキシフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［２１］１−（４−アミノスルホニルフェニル）−５−（３−クロロ−４−フルオロフェニル）−４，５−ジヒドロ−３−トリフルオロメチル−１Ｈ−ピラゾール、
［２２］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−３−トリフルオロメチル−５−（４−トリフルオロメトキシフェニル）−１Ｈ−ピラゾール、
［２３］１−（４−アミノスルホニルフェニル）−５−（２，３−ジフルオロフェニル）−４，５−ジヒドロ−３−トリフルオロメチル−１Ｈ−ピラゾール、
［２４］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（２，４−ジメチルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［２５］５−（３，４−ジフルオロフェニル）−４，５−ジヒドロ−１−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［２６］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（４−フルオロフェニル）−３−メチル−１Ｈ−ピラゾール、
［２７］４，５−ジヒドロ−５−（４−フルオロフェニル）−３−メチル−１−（４−メチルスルホニルフェニル）−１Ｈ−ピラゾール、
［２８］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−３−メチル−５−（４−メチルフェニル）−１Ｈ−ピラゾール、
［２９］４，５−ジヒドロ−３−メチル−５−（４−メチルフェニル）−１−（４−メチルスルホニルフェニル）−１Ｈ−ピラゾール、
［３０］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−３−メチル−５−（４−トリフルオロメチルフェニル）−１Ｈ−ピラゾール、
［３１］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−フェニル−１Ｈ−ピラゾール、
［３２］４，５−ジヒドロ−５−フェニル−１−（４−メチルスルホニルフェニル） −１Ｈ−ピラゾール、
［３３］４，５−ジヒドロ−３−メチル−１−（４−メチルスルホニルフェニル）−５−（４−トリフルオロメチルフェニル）−１Ｈ−ピラゾール、
［３４］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（４−メチルフェニル）−１Ｈ−ピラゾール−３−カルボン酸、
［３５］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−フェニル−１Ｈ−ピラゾール−３−カルボン酸、
［３６］４，５−ジヒドロ−５−（４−メチルフェニル）−１−（４−メチルスルホニルフェニル）−１Ｈ−ピラゾール−３−カルボン酸、
［３７］メチル＝１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（４−メチルフェニル）−１Ｈ−ピラゾール−３−カルボキシラート、
［３８］メチル＝１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−フェニル−１Ｈ−ピラゾール−３−カルボキシラート、
［３９］メチル＝４，５−ジヒドロ−５−（４−メチルフェニル）−１−（４−メチルスルホニルフェニル）−１Ｈ−ピラゾール−３−カルボキシラート、
［４０］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−フェニル−１Ｈ−ピラゾール−３−カルボキサミド、
［４１］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（４−メチルフェニル）−１Ｈ−ピラゾール−３−カルボキサミド、
［４２］４，５−ジヒドロ−５−（４−メチルフェニル）−１−（４−メチルスルホニルフェニル）−１Ｈ−ピラゾール−３−カルボキサミド、
［４３］３−シアノ−４，５−ジヒドロ−５−（４−メチルフェニル）−１−（４−メチルスルホニルフェニル）−１Ｈ−ピラゾール、
［４４］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（３，４−ジメチルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［４５］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（３−メチル−４−メトキシフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［４６］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（３−フルオロ−４−メトキシフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［４７］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（２−フルオロ−４−メトキシフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［４８］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（２，４−ジメトキシフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［４９］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（４−フルオロ−２−メトキシフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［５０］１−（４−アミノスルホニルフェニル）−３−ジフルオロメチル−４，５−ジヒドロ−５−（２，４−ジメチルフェニル）−１Ｈ−ピラゾール、
［５１］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（２，３，４−トリフルオロフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［５２］１−（４−アミノスルホニルフェニル）−５−（２−クロロ−４−フルオロフェニル）−４，５−ジヒドロ−３−トリフルオロメチル−１Ｈ−ピラゾール、
［５３］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（２−フルオロ−４−トリフルオロメチルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［５４］１−（４−アミノスルホニルフェニル）−５−［２，４−ビス（トリフルオロメチル）フェニル］−４，５−ジヒドロ−３−トリフルオロメチル−１Ｈ−ピラゾール、
［５５］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（２−メチル−３−フルオロフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［５６］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（２−メチル−４−メトキシフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［５７］１−（４−アミノスルホニルフェニル）−５−（２，４−ジフルオロフェニル）−３−ジフルオロメチル−４，５−ジヒドロ−１Ｈ−ピラゾール、
［５８］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（４−フルオロ−２−トリフルオロメチルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［５９］１−（２，４−ジフルオロフェニル）−４，５−ジヒドロ−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［６０］１−（４−アミノスルホニルフェニル）−５−（２−クロロフェニル）−４，５−ジヒドロ−３−トリフルオロメチル−１Ｈ−ピラゾール、
［６１］１−（４−アミノスルホニルフェニル）−５−（４−クロロ−２−フルオロフェニル）−４，５−ジヒドロ−３−トリフルオロメチル−１Ｈ−ピラゾール、
［６２］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（４−フルオロ−２−メチルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［６３］１−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−５−（２−フルオロ−４−メチルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［６４］１−（４−アセチルアミノスルホニルフェニル）−５−（２，４−ジフルオロフェニル）−４，５−ジヒドロ−３−トリフルオロメチル−１Ｈ−ピラゾール、
［６５］１−（４−クロロフェニル）−４，５−ジヒドロ−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［６６］４，５−ジヒドロ−１−フェニル−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［６７］４，５−ジヒドロ−１−（２−フルオロフェニル）−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［６８］１−（４−クロロ−２−メチルフェニル）−４，５−ジヒドロ−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［６９］４，５−ジヒドロ−１−（３−フルオロフェニル）−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［７０］４，５−ジヒドロ−１−（３−メチルフェニル）−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［７１］４，５−ジヒドロ−１−（２，４−ジメチルフェニル）−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［７２］１−（２−クロロフェニル）−４，５−ジヒドロ−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［７３］４，５−ジヒドロ−１−（２−メチルフェニル）−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［７４］１−（２，４−ジクロロフェニル）−４，５−ジヒドロ−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［７５］４，５−ジヒドロ−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１−（２−トリフルオロメチルフェニル）−１Ｈ−ピラゾール
［７６］５−（４−アミノスルホニルフェニル）−４，５−ジヒドロ−１−（４−フルオロフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［７７］４，５−ジヒドロ−１−フェニル−３−メチル−５−（４−メチルスルホニルフェニル）−１Ｈ−ピラゾール、
［７８］４，５−ジヒドロ−１−（４−フルオロフェニル）−５−（４−メチルスルホニルフェニル）−１Ｈ−ピラゾール、
［７９］（＋）−１−（４−アミノスルホニルフェニル）−５−（２，４−ジフルオロフェニル）−４，５−ジヒドロ−３−トリフルオロメチル−１Ｈ−ピラゾール、
［８０］（−）−１−（４−アミノスルホニルフェニル）−５−（２，４−ジフルオロフェニル）−４，５−ジヒドロ−３−トリフルオロメチル−１Ｈ−ピラゾール、
［８１］（＋）−４，５−ジヒドロ−１−（４−フルオロフェニル）−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［８２］（−）−４，５−ジヒドロ−１−（４−フルオロフェニル）−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［８３］（＋）−１−（２，４−ジフルオロフェニル）−４，５−ジヒドロ−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
［８４］（−）−１−（２，４−ジフルオロフェニル）−４，５−ジヒドロ−５−（４−メチルスルホニルフェニル）−３−トリフルオロメチル−１Ｈ−ピラゾール、
から成る群より選ばれ、
前記化合物又はその生理的許容塩を、ヒトを含む哺乳動物における細胞増殖疾患の予防又は治療薬、より詳細には、新生物形成前又は新生物形成過程、腫瘍血管新生、悪液質、及び腫瘍壊死因子（ＴＮＦ）に関わる病的状態、また一般に、シクロオキシゲナーゼ−２（ＣＯＸ−２）合成の原因となる遺伝子の発現抑制により利益を受ける病的状態の予防又は治療薬の調製に使用することを特徴とする方法。 - 請求項１に記載の一般構造式（Ｉ）で示される化合物又はその生理的許容塩の使用であって、
相乗効果を生じさせるため、新形成の治療に一般的に用いられる他の生成物と共に、前記化合物又はその生理的許容塩を、ヒトを含む哺乳動物における細胞増殖疾患の予防又は治療薬、より詳細には、新生物形成前又は新生物形成過程、腫瘍血管新生、悪液質、及び腫瘍壊死因子（ＴＮＦ）に関わる病的状態、また一般に、シクロオキシゲナーゼ−２（ＣＯＸ−２）合成の原因となる遺伝子の発現抑制により利益を受ける病的状態の予防又は治療薬の調製に使用することを特徴とする方法。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200100818A ES2174757B1 (es) | 2001-04-06 | 2001-04-06 | Empleo de derivados de firazolinas en la elaboracion de un medicamentopara la prevencion y/o el tratamiento de enfermedades proliferativas celulares. |
| PCT/ES2002/000137 WO2002080909A1 (es) | 2001-04-06 | 2002-03-21 | Empleo de derivados de pirazolinas en la elaboración de un medicamento para la prevención y/o el tratamiento de enfermedades proliferativas celulares |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004525166A JP2004525166A (ja) | 2004-08-19 |
| JP2004525166A5 true JP2004525166A5 (ja) | 2005-09-15 |
| JP4451599B2 JP4451599B2 (ja) | 2010-04-14 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002578948A Expired - Fee Related JP4451599B2 (ja) | 2001-04-06 | 2002-03-21 | 細胞増殖疾患の予防及び／又は治療薬の調製におけるピラゾリン誘導体の使用 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US20040034082A1 (ja) |
| EP (2) | EP1516621A3 (ja) |
| JP (1) | JP4451599B2 (ja) |
| KR (1) | KR20040025912A (ja) |
| CN (2) | CN1299682C (ja) |
| AT (1) | ATE326966T1 (ja) |
| AU (1) | AU2002246152B2 (ja) |
| BR (1) | BR0208805A (ja) |
| CA (1) | CA2442974C (ja) |
| CY (1) | CY1105523T1 (ja) |
| DE (1) | DE60211681T2 (ja) |
| DK (1) | DK1384477T3 (ja) |
| ES (2) | ES2174757B1 (ja) |
| HK (1) | HK1067311A1 (ja) |
| HU (1) | HUP0400918A3 (ja) |
| IL (1) | IL158269A0 (ja) |
| IS (1) | IS6973A (ja) |
| MA (1) | MA27019A1 (ja) |
| MX (1) | MXPA03009124A (ja) |
| NO (1) | NO20034470L (ja) |
| NZ (1) | NZ529304A (ja) |
| PL (1) | PL365220A1 (ja) |
| PT (1) | PT1384477E (ja) |
| RU (1) | RU2305545C2 (ja) |
| UA (1) | UA75402C2 (ja) |
| WO (1) | WO2002080909A1 (ja) |
| ZA (1) | ZA200308626B (ja) |
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| BRPI0507718A (pt) * | 2004-02-16 | 2007-07-03 | Esteve Labor Dr | derivados de pirazolina úteis para o tratamento de cáncer |
| ES2238923B1 (es) * | 2004-02-16 | 2006-11-01 | Laboratorios Del Dr. Esteve, S.A. | Nuevos derivados pirazolinicos sustituidos. |
| EP1637522A1 (en) * | 2004-09-16 | 2006-03-22 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds for reducing triglycerides in blood |
| KR20060135815A (ko) * | 2004-02-17 | 2006-12-29 | 라보라토리오스 델 드라. 에스테브.에스.에이. | 혈중 트리글리세리드를 감소시키기 위한 치환된 피라졸린화합물 |
| TW200533657A (en) | 2004-02-17 | 2005-10-16 | Esteve Labor Dr | Substituted pyrazoline compounds, their preparation and use as medicaments |
| US7998996B2 (en) | 2004-02-17 | 2011-08-16 | Laboratorios Del Dr. Esteve S.A. | Substituted pyrazoline compounds for reducing triglycerides in blood |
| EP1743892A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios del Dr. Esteve S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| EP1849784A1 (en) * | 2006-04-26 | 2007-10-31 | Laboratorios Del Dr. Esteve, S.A. | Indoline-substituted pyrazoline compounds, their preparation and use as medicaments |
| EP1743637A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios Del Dr. Esteve, S.A. | Use of substituted pyrazole compounds and combinations thereof for the treatment of the metabolic syndrome |
| US7897589B2 (en) | 2005-07-15 | 2011-03-01 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| WO2007009702A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| EP1849776A1 (en) * | 2006-04-26 | 2007-10-31 | Laboratorios Del Dr. Esteve, S.A. | Azepane- or Azocane-substituted pyrazoline compounds, their preparation and use as medicaments |
| EP1743642A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios Del Dr. Esteve, S.A. | Use of substituted pyrazoline compounds and their derivatives for the treatment of cannabinoid system-associated diseases |
| ES2327203B1 (es) * | 2005-07-15 | 2010-06-07 | Laboratorios Del Dr. Esteve, S.A. | Uso de compuestos de pirazolina sustituidos para el tratamiento de trastornos relacionados con la coagulacion. |
| WO2007009704A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A. | Use of substituted pyrazoline compounds for the treatment of food disorders, including obesity or metabolic syndrome in patients with developed diabetes |
| EP1749527A1 (en) * | 2005-07-15 | 2007-02-07 | Laboratorios Del Dr. Esteve, S.A. | Use of substituted pyrazoline compounds for the treatment of the lipid parameters of the metabolic syndrome |
| WO2007009699A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A | Use of substituted pyrazoline compounds and their derivatives for the treatment of cannabinoid system-associated diseases |
| WO2007009706A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| EP1743889A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios del Dr. Esteve S.A. | Sustituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| ES2319074B1 (es) * | 2005-07-15 | 2009-12-03 | Laboratorios Del Dr. Esteve, S.A. | Combinacion de principios activos. |
| ES2326724B1 (es) * | 2005-07-15 | 2010-05-11 | Laboratorios Del Dr. Esteve, S.A. | Nuevas formulaciones de compuestos de pirazolina sustituidos. |
| EP1743643A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios Del Dr. Esteve, S.A. | New formulations of substituted pyrazoline compounds |
| EP1743636A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios Del Dr. Esteve, S.A. | Combination of a substituted pyrazoline compound and a drug used in food-related disorders |
| EP1749526A1 (en) * | 2005-07-15 | 2007-02-07 | Laboratorios Del Dr. Esteve, S.A. | Use of substituted pyrazoline compounds for the treatment of food disorders, including obesity or metabolic syndrome in patients with developed diabetes |
| EP1743639A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios Del Dr. Esteve, S.A. | Use of substituted pyrazoline compounds for the treatment of coagulation related diseases |
| ES2316306B1 (es) * | 2005-07-15 | 2009-11-23 | Laboratorios Del Dr. Esteve, S.A. | Combinacion de un compuesto de pirazolina sustituido y un farmaco utilizado en trastornos relacionados con los alimentos. |
| EP1746090A1 (en) * | 2005-07-15 | 2007-01-24 | Laboratorios del Dr. Esteve S.A. | Sustituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| WO2007009701A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A. | Use of substituted pyrazole compounds and combinations thereof for the treatment of the metabolic syndrome |
| EP1749525A1 (en) * | 2005-07-15 | 2007-02-07 | Laboratorios Del Dr. Esteve, S.A. | Combination of substituted pyrazolines and anti-addictive agent |
| ES2327379B1 (es) * | 2005-07-15 | 2010-05-28 | Laboratorios Del Dr. Esteve, S.A. | Compuestos de pirazolina indolinsustituidos, su preparacion y su uso como medicamentos. |
| EP1743890A1 (en) | 2005-07-15 | 2007-01-17 | Laboratorios Del Dr. Esteve, S.A. | 4,5-Dihydro-1H-pyrazole derivatives, their preparation and use as medicaments |
| ES2326857B1 (es) * | 2005-07-15 | 2010-05-11 | Laboratorios Del Dr. Esteve, S.A. | Uso de compuestos de pirazolina sustituidos para el tratamiento de los parametros lipidicos del sindrome metabolico. |
| KR101457637B1 (ko) * | 2012-10-24 | 2014-11-20 | 건국대학교 산학협력단 | 디히드로피라졸카르보티오아미드 유도체 및 그 제법 및 그 유도체를 포함하는 항암제 조성물 |
| CN103664785A (zh) * | 2013-11-04 | 2014-03-26 | 南京大学 | 一类新颖的二氢吡唑磺胺衍生物的合成及在抗癌药物中的应用 |
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| US5604253A (en) * | 1995-05-22 | 1997-02-18 | Merck Frosst Canada, Inc. | N-benzylindol-3-yl propanoic acid derivatives as cyclooxygenase inhibitors |
| US5972986A (en) * | 1997-10-14 | 1999-10-26 | G.D. Searle & Co. | Method of using cyclooxygenase-2 inhibitors in the treatment and prevention of neoplasia |
| ES2137138B1 (es) * | 1998-05-29 | 2000-09-16 | Esteve Labor Dr | Derivados de pirazolinas, su preparacion y su aplicacion como medicamentos. |
| NZ516553A (en) * | 1999-06-16 | 2004-01-30 | Univ Temple | 1-(4-sulfamylaryl)-3-substituted-5-aryl-2-pyrazolines as inhibitors of cyclooxygenase-2 and its preparation method |
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2001
- 2001-04-06 ES ES200100818A patent/ES2174757B1/es not_active Expired - Fee Related
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2002
- 2002-03-21 WO PCT/ES2002/000137 patent/WO2002080909A1/es active IP Right Grant
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- 2002-03-21 NZ NZ529304A patent/NZ529304A/en unknown
- 2002-03-21 ZA ZA200308626A patent/ZA200308626B/en unknown
- 2002-03-21 PL PL02365220A patent/PL365220A1/xx not_active Application Discontinuation
- 2002-03-21 EP EP04030751A patent/EP1516621A3/en not_active Withdrawn
- 2002-03-21 HU HU0400918A patent/HUP0400918A3/hu unknown
- 2002-03-21 CN CNB028098935A patent/CN1299682C/zh not_active Expired - Fee Related
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- 2002-03-21 DE DE60211681T patent/DE60211681T2/de not_active Expired - Lifetime
- 2002-03-21 CA CA2442974A patent/CA2442974C/en not_active Expired - Fee Related
- 2002-03-21 IL IL15826902A patent/IL158269A0/xx unknown
- 2002-03-21 CN CNA2005100713090A patent/CN1698602A/zh active Pending
- 2002-03-21 DK DK02714233T patent/DK1384477T3/da active
- 2002-03-21 PT PT02714233T patent/PT1384477E/pt unknown
- 2002-03-21 AT AT02714233T patent/ATE326966T1/de not_active IP Right Cessation
- 2002-03-21 KR KR10-2003-7013062A patent/KR20040025912A/ko not_active Application Discontinuation
- 2002-03-21 RU RU2003132457/15A patent/RU2305545C2/ru not_active IP Right Cessation
- 2002-03-21 AU AU2002246152A patent/AU2002246152B2/en not_active Ceased
- 2002-03-21 UA UA2003119998A patent/UA75402C2/uk unknown
- 2002-03-21 BR BR0208805-3A patent/BR0208805A/pt not_active IP Right Cessation
- 2002-03-21 JP JP2002578948A patent/JP4451599B2/ja not_active Expired - Fee Related
- 2002-03-21 US US10/312,193 patent/US20040034082A1/en not_active Abandoned
- 2002-03-21 MX MXPA03009124A patent/MXPA03009124A/es active IP Right Grant
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2003
- 2003-10-03 IS IS6973A patent/IS6973A/is unknown
- 2003-10-06 NO NO20034470A patent/NO20034470L/no not_active Application Discontinuation
- 2003-11-05 MA MA27382A patent/MA27019A1/fr unknown
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2004
- 2004-12-30 HK HK04110341A patent/HK1067311A1/xx not_active IP Right Cessation
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2006
- 2006-08-03 CY CY20061101088T patent/CY1105523T1/el unknown
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