ZA200308626B - Utilization of pyrazoline derivatives in the preparation of a medicament for the prevention and/or treatment of poroliferative cell diseases. - Google Patents
Utilization of pyrazoline derivatives in the preparation of a medicament for the prevention and/or treatment of poroliferative cell diseases. Download PDFInfo
- Publication number
- ZA200308626B ZA200308626B ZA200308626A ZA200308626A ZA200308626B ZA 200308626 B ZA200308626 B ZA 200308626B ZA 200308626 A ZA200308626 A ZA 200308626A ZA 200308626 A ZA200308626 A ZA 200308626A ZA 200308626 B ZA200308626 B ZA 200308626B
- Authority
- ZA
- South Africa
- Prior art keywords
- dihydro
- pyrazol
- trifluoromethyl
- aminosulphonylphenyl
- methylsulphonylphenyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 15
- 239000003814 drug Substances 0.000 title claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 10
- 201000010099 disease Diseases 0.000 title claims description 8
- 150000003219 pyrazolines Chemical class 0.000 title claims description 3
- 230000002265 prevention Effects 0.000 title description 7
- -1 methoxy, trifluoromethoxy, methylsulphonyl Chemical group 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000004429 atom Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 102000010907 Cyclooxygenase 2 Human genes 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 15
- 108090000623 proteins and genes Proteins 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 230000001173 tumoral effect Effects 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 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 description 9
- 230000014509 gene expression Effects 0.000 claims description 9
- 230000002914 neoplasic effect Effects 0.000 claims description 8
- 206010006895 Cachexia Diseases 0.000 claims description 7
- 230000004663 cell proliferation Effects 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 230000005764 inhibitory process Effects 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 101150071146 COX2 gene Proteins 0.000 claims description 3
- 230000009826 neoplastic cell growth Effects 0.000 claims description 3
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 108050007852 Tumour necrosis factor Proteins 0.000 claims 5
- 102000018594 Tumour necrosis factor Human genes 0.000 claims 5
- 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 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
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- 230000002194 synthesizing effect Effects 0.000 claims 3
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- YSBOXIAEPKVZLS-UHFFFAOYSA-N 3,4,5-trifluoro-1-methylpyrazole Chemical compound CN1N=C(F)C(F)=C1F YSBOXIAEPKVZLS-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims 2
- 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
- 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
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- SUWOQIFACNCUKF-UHFFFAOYSA-N 3-(trifluoromethyl)-4,5-dihydro-1h-pyrazole Chemical compound FC(F)(F)C1=NNCC1 SUWOQIFACNCUKF-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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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
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| 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. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200308626B true ZA200308626B (en) | 2004-11-05 |
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Family Applications (1)
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|---|---|---|---|
| ZA200308626A ZA200308626B (en) | 2001-04-06 | 2002-03-21 | Utilization of pyrazoline derivatives in the preparation of a medicament for the prevention and/or treatment of poroliferative cell diseases. |
Country Status (26)
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|---|---|
| US (1) | US20040034082A1 (https=) |
| EP (2) | EP1516621A3 (https=) |
| JP (1) | JP4451599B2 (https=) |
| KR (1) | KR20040025912A (https=) |
| CN (2) | CN1299682C (https=) |
| AT (1) | ATE326966T1 (https=) |
| AU (1) | AU2002246152B2 (https=) |
| BR (1) | BR0208805A (https=) |
| CA (1) | CA2442974C (https=) |
| CY (1) | CY1105523T1 (https=) |
| DE (1) | DE60211681T2 (https=) |
| DK (1) | DK1384477T3 (https=) |
| ES (2) | ES2174757B1 (https=) |
| HU (1) | HUP0400918A3 (https=) |
| IL (1) | IL158269A0 (https=) |
| IS (1) | IS6973A (https=) |
| MA (1) | MA27019A1 (https=) |
| MX (1) | MXPA03009124A (https=) |
| NO (1) | NO20034470L (https=) |
| NZ (1) | NZ529304A (https=) |
| PL (1) | PL365220A1 (https=) |
| PT (1) | PT1384477E (https=) |
| RU (1) | RU2305545C2 (https=) |
| UA (1) | UA75402C2 (https=) |
| WO (1) | WO2002080909A1 (https=) |
| ZA (1) | ZA200308626B (https=) |
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| WO2005077910A1 (en) * | 2004-02-16 | 2005-08-25 | Laboratorios Del Dr. Esteve S.A. | Pyrazoline derivatives useful for the treatment of cancer |
| ES2238923B1 (es) * | 2004-02-16 | 2006-11-01 | Laboratorios Del Dr. Esteve, S.A. | Nuevos derivados pirazolinicos sustituidos. |
| US7998996B2 (en) | 2004-02-17 | 2011-08-16 | Laboratorios Del Dr. Esteve S.A. | Substituted pyrazoline compounds for reducing triglycerides in blood |
| EP1637522A1 (en) * | 2004-09-16 | 2006-03-22 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds for reducing triglycerides in blood |
| CA2556568A1 (en) * | 2004-02-17 | 2005-08-25 | Laboratorios Del Dr. Esteve S.A. | Substituted pyrazoline compounds for reducing triglycerides in blood |
| TW200533657A (en) | 2004-02-17 | 2005-10-16 | Esteve Labor Dr | Substituted pyrazoline compounds, their preparation and use as medicaments |
| EP1749525A1 (en) * | 2005-07-15 | 2007-02-07 | Laboratorios Del Dr. Esteve, S.A. | Combination of substituted pyrazolines and anti-addictive agent |
| WO2007009703A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A. | New formulations of substituted pyrazoline compounds |
| 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 |
| 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 |
| 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. |
| ES2319074B1 (es) * | 2005-07-15 | 2009-12-03 | Laboratorios Del Dr. Esteve, S.A. | Combinacion de principios activos. |
| 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. |
| US7897589B2 (en) | 2005-07-15 | 2011-03-01 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| EP1743892A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios del Dr. Esteve S.A. | 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 |
| ES2336883B1 (es) * | 2005-07-15 | 2011-03-22 | Laboratorios Del Dr. Esteve, S.A. | Compuestos de pirazolina sustituidos, con una estereoquimica predeterminada, para la reduccion de trigliceridos en sangre. |
| ES2326725B1 (es) * | 2005-07-15 | 2010-05-11 | Laboratorios Del Dr. Esteve, S.A. | Uso de compuestos de pirazolina sustituidos para el tratamiento de trastornos alimentarios, que incluyen la obesidad o el sindrome metabolico en pacientes con diabetes desarrollada. |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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. |
| 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. |
| 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 |
| 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 |
| 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 |
| 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 |
| EP1743643A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios Del Dr. Esteve, S.A. | New formulations of substituted pyrazoline compounds |
| 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 |
| WO2023043778A1 (en) * | 2021-09-14 | 2023-03-23 | Maverick Gold (Nv), Llc | Methods and systems for titling and trading alternative reserves |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0674624T3 (da) * | 1992-12-17 | 1999-09-13 | Pfizer | Pyrazoler med CRF-antagonistisk aktivitet |
| ES2141916T3 (es) * | 1993-11-30 | 2000-04-01 | Searle & Co | Pirazolil-bencenosulfonamidas sustituidas para el tratamiento de la inflamacion. |
| 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. |
| US6376519B1 (en) * | 1999-06-16 | 2002-04-23 | Temple University-Of The Commonwealth Of Higher Education | 1-(4-sulfamylaryl)-3-substituted-5-aryl-2-pyrazolines and inhibitors of cyclooxygenase-2 |
-
2001
- 2001-04-06 ES ES200100818A patent/ES2174757B1/es not_active Expired - Fee Related
-
2002
- 2002-03-21 PT PT02714233T patent/PT1384477E/pt unknown
- 2002-03-21 NZ NZ529304A patent/NZ529304A/en unknown
- 2002-03-21 CA CA2442974A patent/CA2442974C/en not_active Expired - Fee Related
- 2002-03-21 DK DK02714233T patent/DK1384477T3/da active
- 2002-03-21 DE DE60211681T patent/DE60211681T2/de not_active Expired - Lifetime
- 2002-03-21 WO PCT/ES2002/000137 patent/WO2002080909A1/es not_active Ceased
- 2002-03-21 UA UA2003119998A patent/UA75402C2/uk unknown
- 2002-03-21 EP EP04030751A patent/EP1516621A3/en not_active Withdrawn
- 2002-03-21 HU HU0400918A patent/HUP0400918A3/hu unknown
- 2002-03-21 BR BR0208805-3A patent/BR0208805A/pt not_active IP Right Cessation
- 2002-03-21 ES ES02714233T patent/ES2264723T3/es not_active Expired - Lifetime
- 2002-03-21 RU RU2003132457/15A patent/RU2305545C2/ru not_active IP Right Cessation
- 2002-03-21 MX MXPA03009124A patent/MXPA03009124A/es active IP Right Grant
- 2002-03-21 JP JP2002578948A patent/JP4451599B2/ja not_active Expired - Fee Related
- 2002-03-21 IL IL15826902A patent/IL158269A0/xx unknown
- 2002-03-21 ZA ZA200308626A patent/ZA200308626B/en unknown
- 2002-03-21 EP EP02714233A patent/EP1384477B1/en not_active Expired - Lifetime
- 2002-03-21 KR KR10-2003-7013062A patent/KR20040025912A/ko not_active Ceased
- 2002-03-21 PL PL02365220A patent/PL365220A1/xx not_active Application Discontinuation
- 2002-03-21 CN CNB028098935A patent/CN1299682C/zh not_active Expired - Fee Related
- 2002-03-21 AT AT02714233T patent/ATE326966T1/de not_active IP Right Cessation
- 2002-03-21 CN CNA2005100713090A patent/CN1698602A/zh active Pending
- 2002-03-21 AU AU2002246152A patent/AU2002246152B2/en not_active Ceased
- 2002-03-21 US US10/312,193 patent/US20040034082A1/en not_active Abandoned
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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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2006
- 2006-08-03 CY CY20061101088T patent/CY1105523T1/el unknown
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