NO312066B1 - Substituerte isoxazoler, farmasöytisk preparat inneholdende slike forbindelser, fremgangsmåte for deres fremstilling oganvendelse derav, samt mellomprodukter - Google Patents

Info

Publication number

NO312066B1

NO312066B1 NO19973711A NO973711A NO312066B1 NO 312066 B1 NO312066 B1 NO 312066B1 NO 19973711 A NO19973711 A NO 19973711A NO 973711 A NO973711 A NO 973711A NO 312066 B1 NO312066 B1 NO 312066B1

Authority

NO

Norway

Prior art keywords

alkyl

phenyl

benzenesulfonamide

phenylisoxazol

methyl

Prior art date

1995-02-13

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 117
• 238000002360 preparation method Methods 0.000 title claims description 141
• 238000000034 method Methods 0.000 title claims description 85
• 239000000825 pharmaceutical preparation Chemical class 0.000 title claims description 9
• 230000008569 process Effects 0.000 title claims description 8
• 150000002545 isoxazoles Chemical class 0.000 title description 19
• 239000000543 intermediate Substances 0.000 title description 10
• -1 carboxyphenyloxy Chemical group 0.000 claims description 129
• 239000000203 mixture Substances 0.000 claims description 115
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 58
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 48
• 238000006243 chemical reaction Methods 0.000 claims description 43
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 40
• 150000002923 oximes Chemical class 0.000 claims description 38
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 37
• 239000002253 acid Substances 0.000 claims description 35
• 229910052736 halogen Inorganic materials 0.000 claims description 32
• 150000002367 halogens Chemical class 0.000 claims description 31
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 29
• 229940124530 sulfonamide Drugs 0.000 claims description 27
• 150000003456 sulfonamides Chemical class 0.000 claims description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 24
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
• 235000011054 acetic acid Nutrition 0.000 claims description 20
• 230000004054 inflammatory process Effects 0.000 claims description 20
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 18
• 206010061218 Inflammation Diseases 0.000 claims description 18
• XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 18
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 18
• 239000000460 chlorine Substances 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
• OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 claims description 11
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
• 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 11
• 229910021529 ammonia Inorganic materials 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 150000008064 anhydrides Chemical class 0.000 claims description 7
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• 208000035475 disorder Diseases 0.000 claims description 7
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 7
• 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 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 claims description 6
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 6
• 206010003246 arthritis Diseases 0.000 claims description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
• 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 6
• ZHHXZLZHSVHDAY-UHFFFAOYSA-N 4-(3-phenyl-5-propyl-1,2-oxazol-4-yl)benzenesulfonamide Chemical compound CCCC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 ZHHXZLZHSVHDAY-UHFFFAOYSA-N 0.000 claims description 5
• JCVNIGQCRRPLCI-UHFFFAOYSA-N 4-[5-(chloromethyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(CCl)ON=C1C1=CC=CC=C1 JCVNIGQCRRPLCI-UHFFFAOYSA-N 0.000 claims description 5
• 208000002193 Pain Diseases 0.000 claims description 5
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
• 150000001450 anions Chemical class 0.000 claims description 5
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 230000036407 pain Effects 0.000 claims description 5
• 230000001225 therapeutic effect Effects 0.000 claims description 5
• JKLWRNPSXPFPNN-UHFFFAOYSA-N 2-[3-phenyl-4-(4-sulfamoylphenyl)-1,2-oxazol-5-yl]propanoic acid Chemical compound OC(=O)C(C)C=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 JKLWRNPSXPFPNN-UHFFFAOYSA-N 0.000 claims description 4
• BSPWDCBKHIARSE-UHFFFAOYSA-N 3-(3-chloro-4-methoxyphenyl)-5-methyl-4-(4-methylsulfonylphenyl)-1,2-oxazole Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NOC(C)=C1C1=CC=C(S(C)(=O)=O)C=C1 BSPWDCBKHIARSE-UHFFFAOYSA-N 0.000 claims description 4
• BHTAUAXXUUNFFL-UHFFFAOYSA-N 4-(5-cyclohexyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C2CCCCC2)ON=C1C1=CC=CC=C1 BHTAUAXXUUNFFL-UHFFFAOYSA-N 0.000 claims description 4
• BEGIFIRFMQXGMC-UHFFFAOYSA-N 4-(5-ethyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide Chemical compound CCC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 BEGIFIRFMQXGMC-UHFFFAOYSA-N 0.000 claims description 4
• GLECBWFQVQHIJB-UHFFFAOYSA-N 4-[3-(3,5-difluorophenyl)-5-methyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound CC=1ON=C(C=2C=C(F)C=C(F)C=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 GLECBWFQVQHIJB-UHFFFAOYSA-N 0.000 claims description 4
• XVRUBQNKFOVVQW-UHFFFAOYSA-N 4-[3-(3-chloro-4-methylphenyl)-5-methyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound CC=1ON=C(C=2C=C(Cl)C(C)=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 XVRUBQNKFOVVQW-UHFFFAOYSA-N 0.000 claims description 4
• YFZHJDXAHZEAGF-UHFFFAOYSA-N 4-[3-(4-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound CC=1ON=C(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 YFZHJDXAHZEAGF-UHFFFAOYSA-N 0.000 claims description 4
• GOXOPHCMJMGBPC-UHFFFAOYSA-N 4-[5-(2-methylpropyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound CC(C)CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 GOXOPHCMJMGBPC-UHFFFAOYSA-N 0.000 claims description 4
• QAXHRJUFSGUUNC-UHFFFAOYSA-N 4-[5-(3-hydroxypropyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(CCCO)ON=C1C1=CC=CC=C1 QAXHRJUFSGUUNC-UHFFFAOYSA-N 0.000 claims description 4
• AGQZHNGQSJSQMR-UHFFFAOYSA-N 4-[5-(cyclohexylmethyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(C(=NO1)C=2C=CC=CC=2)=C1CC1CCCCC1 AGQZHNGQSJSQMR-UHFFFAOYSA-N 0.000 claims description 4
• DVSOGWILWKEIDD-UHFFFAOYSA-N 4-[5-(difluoromethyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C(F)F)ON=C1C1=CC=CC=C1 DVSOGWILWKEIDD-UHFFFAOYSA-N 0.000 claims description 4
• OWYQECTYMQVGEG-UHFFFAOYSA-N 4-[5-(methoxymethyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound COCC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 OWYQECTYMQVGEG-UHFFFAOYSA-N 0.000 claims description 4
• XPCNRAYPJOMCMK-UHFFFAOYSA-N 4-[5-[(4-chlorophenyl)methyl]-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(C(=NO1)C=2C=CC=CC=2)=C1CC1=CC=C(Cl)C=C1 XPCNRAYPJOMCMK-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
• 125000000217 alkyl group Chemical group 0.000 claims description 4
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
• 230000018044 dehydration Effects 0.000 claims description 4
• 238000006297 dehydration reaction Methods 0.000 claims description 4
• 125000006003 dichloroethyl group Chemical group 0.000 claims description 4
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 4
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 125000006343 heptafluoro propyl group Chemical group 0.000 claims description 4
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
• AQKFDFRMIGWSJH-UHFFFAOYSA-N 2-[3-phenyl-4-(4-sulfamoylphenyl)-1,2-oxazol-5-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(CC(O)=O)ON=C1C1=CC=CC=C1 AQKFDFRMIGWSJH-UHFFFAOYSA-N 0.000 claims description 3
• PRDZNASBXLEEBZ-UHFFFAOYSA-N 4-(3-phenyl-5-propan-2-yl-1,2-oxazol-4-yl)benzenesulfonamide Chemical compound CC(C)C=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 PRDZNASBXLEEBZ-UHFFFAOYSA-N 0.000 claims description 3
• LIMULJONDWLNRH-UHFFFAOYSA-N 4-(3-phenyl-5-propyl-1,2-oxazol-4-yl)benzenesulfonic acid Chemical compound CCCC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(O)(=O)=O)C=C1 LIMULJONDWLNRH-UHFFFAOYSA-N 0.000 claims description 3
• XUMZDTTVZVNYGS-UHFFFAOYSA-N 4-(5-cyano-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C#N)ON=C1C1=CC=CC=C1 XUMZDTTVZVNYGS-UHFFFAOYSA-N 0.000 claims description 3
• CJSMXPUCAFCFAX-UHFFFAOYSA-N 4-[3-(3-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound CC=1ON=C(C=2C=C(Cl)C=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 CJSMXPUCAFCFAX-UHFFFAOYSA-N 0.000 claims description 3
• VAPRSAUIFJVXAA-UHFFFAOYSA-N 4-[3-(3-fluoro-4-methoxyphenyl)-5-methyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1C1=NOC(C)=C1C1=CC=C(S(N)(=O)=O)C=C1 VAPRSAUIFJVXAA-UHFFFAOYSA-N 0.000 claims description 3
• YHFBILXCDDTVMO-UHFFFAOYSA-N 4-[3-(3-fluoro-4-methylphenyl)-5-methyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound CC=1ON=C(C=2C=C(F)C(C)=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 YHFBILXCDDTVMO-UHFFFAOYSA-N 0.000 claims description 3
• RNIMVOKEBWWAFB-UHFFFAOYSA-N 4-[3-(3-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound CC=1ON=C(C=2C=C(F)C=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 RNIMVOKEBWWAFB-UHFFFAOYSA-N 0.000 claims description 3
• GVLVIZRBGRSLTK-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 GVLVIZRBGRSLTK-UHFFFAOYSA-N 0.000 claims description 3
• WGZUTHBSWKIFNQ-UHFFFAOYSA-N 4-[5-(2,2-dimethylpropyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound CC(C)(C)CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 WGZUTHBSWKIFNQ-UHFFFAOYSA-N 0.000 claims description 3
• ZLPCRPIDSXHGTO-UHFFFAOYSA-N 4-[5-(difluoromethyl)-3-(3-fluoro-4-methoxyphenyl)-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1C1=NOC(C(F)F)=C1C1=CC=C(S(N)(=O)=O)C=C1 ZLPCRPIDSXHGTO-UHFFFAOYSA-N 0.000 claims description 3
• SJQCGJJJDGGPCJ-UHFFFAOYSA-N 4-[5-(difluoromethyl)-3-(4-methylphenyl)-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1=NOC(C(F)F)=C1C1=CC=C(S(N)(=O)=O)C=C1 SJQCGJJJDGGPCJ-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• APMIVVBYHLSFJD-UHFFFAOYSA-N 5-(difluoromethyl)-4-(4-methylsulfonylphenyl)-3-phenyl-1,2-oxazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C(F)F)ON=C1C1=CC=CC=C1 APMIVVBYHLSFJD-UHFFFAOYSA-N 0.000 claims description 3
• AIWQSOFGFNKOOF-UHFFFAOYSA-N 5-methyl-4-(4-methylsulfonylphenyl)-3-phenyl-1,2-oxazole Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(C)(=O)=O)C=C1 AIWQSOFGFNKOOF-UHFFFAOYSA-N 0.000 claims description 3
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
• 206010037660 Pyrexia Diseases 0.000 claims description 3
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• 239000007800 oxidant agent Substances 0.000 claims description 3
• MFWGLBXPMTYHIL-UHFFFAOYSA-N 2-[3-(3-fluoro-4-methoxyphenyl)-4-(4-methylsulfonylphenyl)-1,2-oxazol-5-yl]acetic acid Chemical compound C1=C(F)C(OC)=CC=C1C1=NOC(CC(O)=O)=C1C1=CC=C(S(C)(=O)=O)C=C1 MFWGLBXPMTYHIL-UHFFFAOYSA-N 0.000 claims description 2
• GKHOLKSRNBYVCC-UHFFFAOYSA-N 4-(5-butyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide Chemical compound CCCCC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 GKHOLKSRNBYVCC-UHFFFAOYSA-N 0.000 claims description 2
• FCXBSLJSGUUREA-UHFFFAOYSA-N 4-(5-chloro-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(Cl)ON=C1C1=CC=CC=C1 FCXBSLJSGUUREA-UHFFFAOYSA-N 0.000 claims description 2
• LLWOSCPRJRUVST-UHFFFAOYSA-N 4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonic acid Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(O)(=O)=O)C=C1 LLWOSCPRJRUVST-UHFFFAOYSA-N 0.000 claims description 2
• ZEZZBHDWONEQRP-UHFFFAOYSA-N 4-(5-methyl-3-pyridin-3-yl-1,2-oxazol-4-yl)benzenesulfonamide Chemical compound CC=1ON=C(C=2C=NC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 ZEZZBHDWONEQRP-UHFFFAOYSA-N 0.000 claims description 2
• BIOIIALQVKMZGI-UHFFFAOYSA-N 4-[3-(3,4-difluorophenyl)-5-methyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound CC=1ON=C(C=2C=C(F)C(F)=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 BIOIIALQVKMZGI-UHFFFAOYSA-N 0.000 claims description 2
• MIWGTEDDCFJPDK-UHFFFAOYSA-N 4-[3-(4-bromophenyl)-5-methyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound CC=1ON=C(C=2C=CC(Br)=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 MIWGTEDDCFJPDK-UHFFFAOYSA-N 0.000 claims description 2
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