SK284788B6 - Použitie inhibítorov cyklooxygenázy-2 pri liečení a prevencii neoplázie - Google Patents

Info

Publication number

SK284788B6

SK284788B6 SK462-99A SK46299A SK284788B6 SK 284788 B6 SK284788 B6 SK 284788B6 SK 46299 A SK46299 A SK 46299A SK 284788 B6 SK284788 B6 SK 284788B6

Authority

SK

Slovakia

Prior art keywords

phenyl

benzenesulfonamide

trifluoromethyl

pyrazol

methylsulfonyl

Prior art date

1996-10-15

Links

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• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 51
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title claims abstract description 38
• 230000009826 neoplastic cell growth Effects 0.000 title claims abstract description 30
• 239000003814 drug Substances 0.000 claims abstract description 9
• -1 hormonal agents Substances 0.000 claims description 121
• 150000001875 compounds Chemical class 0.000 claims description 46
• 150000003839 salts Chemical class 0.000 claims description 33
• 229940111134 coxibs Drugs 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 230000002265 prevention Effects 0.000 claims description 17
• 239000000126 substance Substances 0.000 claims description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• 125000001188 haloalkyl group Chemical group 0.000 claims description 14
• 239000003112 inhibitor Substances 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 108010037462 Cyclooxygenase 2 Proteins 0.000 claims description 12
• 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims description 12
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
• 125000003282 alkyl amino group Chemical group 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 9
• 125000004414 alkyl thio group Chemical group 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 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 9
• 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 9
• 125000001145 hydrido group Chemical group *[H] 0.000 claims description 9
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 7
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000004043 oxo group Chemical group O=* 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 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 5
• 206010060862 Prostate cancer Diseases 0.000 claims description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• ZJOUYQCSZYKGKU-UHFFFAOYSA-N 3-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=NC=CC=2)=NC(C(F)(F)F)=C1 ZJOUYQCSZYKGKU-UHFFFAOYSA-N 0.000 claims description 4
• NSRMOHFGSWCCFK-UHFFFAOYSA-N 4-[2-(5-methylpyridin-3-yl)-4-(trifluoromethyl)imidazol-1-yl]benzenesulfonamide Chemical compound CC1=CN=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(N)(=O)=O)=C1 NSRMOHFGSWCCFK-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• UJSFKTUZOASIPA-UHFFFAOYSA-N 4-[5-(hydroxymethyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(CO)ON=C1C1=CC=CC=C1 UJSFKTUZOASIPA-UHFFFAOYSA-N 0.000 claims description 4
• 208000004804 Adenomatous Polyps Diseases 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 4
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
• 239000004305 biphenyl Substances 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• 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 3
• LWIFWMYFVZYWMS-UHFFFAOYSA-N 1,2-difluoro-3-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=C(F)C=CC=2)F)CCC1 LWIFWMYFVZYWMS-UHFFFAOYSA-N 0.000 claims description 2
• GWMFOHRUWPDLIP-UHFFFAOYSA-N 1-(4-methylsulfonylphenyl)-2-phenyl-4-(trifluoromethyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC=CC=2)=NC(C(F)(F)F)=C1 GWMFOHRUWPDLIP-UHFFFAOYSA-N 0.000 claims description 2
• MBUIIOVYVHAZOU-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)cyclopenten-1-yl]-4-methylsulfonylbenzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)CCC1 MBUIIOVYVHAZOU-UHFFFAOYSA-N 0.000 claims description 2
• VKUCTHVTLJBHDT-UHFFFAOYSA-N 1-[4,4-dimethyl-2-(4-methylsulfonylphenyl)cyclopenten-1-yl]-4-fluorobenzene Chemical compound C1C(C)(C)CC(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 VKUCTHVTLJBHDT-UHFFFAOYSA-N 0.000 claims description 2
• XKSNSSNGFIQSFK-UHFFFAOYSA-N 1-ethyl-4-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)pyrazole Chemical compound FC(F)(F)C=1N(CC)N=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=1C1=CC=C(F)C=C1 XKSNSSNGFIQSFK-UHFFFAOYSA-N 0.000 claims description 2
• RAUHMMADXJJVRP-UHFFFAOYSA-N 1-methoxy-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 RAUHMMADXJJVRP-UHFFFAOYSA-N 0.000 claims description 2
• VCLNQQUCGTWUKD-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-thiazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(C=2C(=CC=CC=2)Cl)S1 VCLNQQUCGTWUKD-UHFFFAOYSA-N 0.000 claims description 2
• NWVGCEQIXKQQPS-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=C(F)C(F)=CC=2)=NC(C(F)(F)F)=C1 NWVGCEQIXKQQPS-UHFFFAOYSA-N 0.000 claims description 2
• YLFBPUKBMRJHLM-UHFFFAOYSA-N 2-(3-chlorophenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=C(Cl)C=CC=2)=NC(C(F)(F)F)=C1 YLFBPUKBMRJHLM-UHFFFAOYSA-N 0.000 claims description 2
• UFSJAWLGOHKVBH-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound C1=C(F)C(OC)=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(C)(=O)=O)C=C1 UFSJAWLGOHKVBH-UHFFFAOYSA-N 0.000 claims description 2
• MEAMLMDMYOLDGW-UHFFFAOYSA-N 2-(3-fluoro-5-methylphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound CC1=CC(F)=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 MEAMLMDMYOLDGW-UHFFFAOYSA-N 0.000 claims description 2
• RSABMOYFBOLDLO-UHFFFAOYSA-N 2-(3-methylphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound CC1=CC=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 RSABMOYFBOLDLO-UHFFFAOYSA-N 0.000 claims description 2
• ZZBKFGAUXXMYNA-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(4-methylsulfonylphenyl)-4-phenylimidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=NC(C=2C=CC=CC=2)=C1 ZZBKFGAUXXMYNA-UHFFFAOYSA-N 0.000 claims description 2
• UPXZCQZUZDWZHE-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=NC(C=2C=CC(F)=CC=2)=C1 UPXZCQZUZDWZHE-UHFFFAOYSA-N 0.000 claims description 2
• RIZFWOPNUQFLEF-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-methyl-1-(4-methylsulfonylphenyl)imidazole Chemical compound N=1C(C)=CN(C=2C=CC(=CC=2)S(C)(=O)=O)C=1C1=CC=C(Cl)C=C1 RIZFWOPNUQFLEF-UHFFFAOYSA-N 0.000 claims description 2
• PEUVGLHBVHFKPT-UHFFFAOYSA-N 2-(4-methylphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound C1=CC(C)=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(C)(=O)=O)C=C1 PEUVGLHBVHFKPT-UHFFFAOYSA-N 0.000 claims description 2
• YRVHNSYUGHFPFQ-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)pyrazol-1-yl]-n-phenylacetamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=C1C(F)(F)F)C=2C=CC(F)=CC=2)=NN1CC(=O)NC1=CC=CC=C1 YRVHNSYUGHFPFQ-UHFFFAOYSA-N 0.000 claims description 2
• AGCRHVNIFLDQNI-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-oxazol-2-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(CC(O)=O)O1 AGCRHVNIFLDQNI-UHFFFAOYSA-N 0.000 claims description 2
• NECDCTAHUMBLQG-UHFFFAOYSA-N 2-bromo-6-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridine-3-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C#N)=C(Br)N=C1C1=CC=C(F)C=C1 NECDCTAHUMBLQG-UHFFFAOYSA-N 0.000 claims description 2
• KYNAWJZJGXEMMS-UHFFFAOYSA-N 2-chloro-1-methoxy-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 KYNAWJZJGXEMMS-UHFFFAOYSA-N 0.000 claims description 2
• ZTHDILTXFNKYMK-UHFFFAOYSA-N 2-methyl-4-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound C1=NC(C)=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 ZTHDILTXFNKYMK-UHFFFAOYSA-N 0.000 claims description 2
• TZUKXDRCVJCLLL-UHFFFAOYSA-N 2-methyl-5-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound C1=NC(C)=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(C)(=O)=O)C=C1 TZUKXDRCVJCLLL-UHFFFAOYSA-N 0.000 claims description 2
• UJAMUMWHXRVKDM-UHFFFAOYSA-N 2-methyl-6-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound CC1=CC=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 UJAMUMWHXRVKDM-UHFFFAOYSA-N 0.000 claims description 2
• AMTZZFUBJIWXKB-UHFFFAOYSA-N 2-tert-butyl-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-oxazole Chemical compound O1C(C(C)(C)C)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 AMTZZFUBJIWXKB-UHFFFAOYSA-N 0.000 claims description 2
• OCROGSYJFYKXMO-UHFFFAOYSA-N 3-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-6-prop-2-ynoxy-2-(trifluoromethyl)pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(OCC#C)=NC(C(F)(F)F)=C1C1=CC=C(F)C=C1 OCROGSYJFYKXMO-UHFFFAOYSA-N 0.000 claims description 2
• VTXIMXSYKSVSGP-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-methoxy-4-(4-methylsulfonylphenyl)-2-(trifluoromethyl)pyridine Chemical compound C=1C=C(F)C=CC=1C=1C(C(F)(F)F)=NC(OC)=CC=1C1=CC=C(S(C)(=O)=O)C=C1 VTXIMXSYKSVSGP-UHFFFAOYSA-N 0.000 claims description 2
• FQJOALWXRJKJFW-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)-1,3-oxazole Chemical compound O1C(C)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 FQJOALWXRJKJFW-UHFFFAOYSA-N 0.000 claims description 2
• HLSMDYHXAPYMPD-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-1-(2-phenylethyl)-5-(trifluoromethyl)pyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=C1C(F)(F)F)C=2C=CC(F)=CC=2)=NN1CCC1=CC=CC=C1 HLSMDYHXAPYMPD-UHFFFAOYSA-N 0.000 claims description 2
• YTLPYUWXEWWKRU-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-1-(2-phenylethyl)pyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=C1)C=2C=CC(F)=CC=2)=NN1CCC1=CC=CC=C1 YTLPYUWXEWWKRU-UHFFFAOYSA-N 0.000 claims description 2
• OHEHAWXOSFKVTI-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-1-prop-2-enyl-5-(trifluoromethyl)pyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=NN(CC=C)C(C(F)(F)F)=C1C1=CC=C(F)C=C1 OHEHAWXOSFKVTI-UHFFFAOYSA-N 0.000 claims description 2
• SAVMISCIBLZUAE-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(trifluoromethyl)-1,3-thiazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(C(F)(F)F)S1 SAVMISCIBLZUAE-UHFFFAOYSA-N 0.000 claims description 2
• QDPWDPOAKFQYJR-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-phenyl-1,3-oxazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(C=2C=CC=CC=2)O1 QDPWDPOAKFQYJR-UHFFFAOYSA-N 0.000 claims description 2
• ISMZMNIRFHOTII-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-thiophen-2-yl-1,3-thiazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(C=2SC=CC=2)S1 ISMZMNIRFHOTII-UHFFFAOYSA-N 0.000 claims description 2
• DEXPHZXXTBGSGZ-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-n-propyl-1,3-thiazol-2-amine Chemical compound S1C(NCCC)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 DEXPHZXXTBGSGZ-UHFFFAOYSA-N 0.000 claims description 2
• UUVBGFWWLRWVAV-UHFFFAOYSA-N 4-(4-methylsulfonylphenyl)-5-thiophen-2-yl-2-(trifluoromethyl)-1h-imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2SC=CC=2)NC(C(F)(F)F)=N1 UUVBGFWWLRWVAV-UHFFFAOYSA-N 0.000 claims description 2
• JPWKLILKLRXARO-UHFFFAOYSA-N 4-[2-(2-methylpyridin-3-yl)-4-(trifluoromethyl)imidazol-1-yl]benzenesulfonamide Chemical compound CC1=NC=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(N)(=O)=O)C=C1 JPWKLILKLRXARO-UHFFFAOYSA-N 0.000 claims description 2
• MSULOQJDYOQZPZ-UHFFFAOYSA-N 4-[2-(3-chloro-4-methoxyphenyl)-4,5-difluorophenyl]benzenesulfonamide Chemical compound C1=C(Cl)C(OC)=CC=C1C1=CC(F)=C(F)C=C1C1=CC=C(S(N)(=O)=O)C=C1 MSULOQJDYOQZPZ-UHFFFAOYSA-N 0.000 claims description 2
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