NO327814B1 - 4,5-diaryl-3(2H)-furanonderivater, fremgangsmate for fremstilling derav, farmasoytiske preparater samt anvendelse av slike derivater - Google Patents
4,5-diaryl-3(2H)-furanonderivater, fremgangsmate for fremstilling derav, farmasoytiske preparater samt anvendelse av slike derivater Download PDFInfo
- Publication number
- NO327814B1 NO327814B1 NO20014986A NO20014986A NO327814B1 NO 327814 B1 NO327814 B1 NO 327814B1 NO 20014986 A NO20014986 A NO 20014986A NO 20014986 A NO20014986 A NO 20014986A NO 327814 B1 NO327814 B1 NO 327814B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- dimethyl
- methylsulfonyl
- furanone
- aminosulfonyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 167
- 238000002360 preparation method Methods 0.000 title claims description 69
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
- 230000008569 process Effects 0.000 title claims description 3
- 206010061218 Inflammation Diseases 0.000 claims abstract description 18
- 230000004054 inflammatory process Effects 0.000 claims abstract description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
- 201000010099 disease Diseases 0.000 claims abstract description 9
- 230000001404 mediated effect Effects 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 962
- -1 pentylideneyl Chemical group 0.000 claims description 186
- 150000001875 compounds Chemical class 0.000 claims description 164
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims description 47
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 40
- 238000003786 synthesis reaction Methods 0.000 claims description 35
- 230000015572 biosynthetic process Effects 0.000 claims description 34
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- 239000001301 oxygen Substances 0.000 claims description 34
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 32
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 29
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 26
- 239000000460 chlorine Chemical group 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- LYINKTVZUSKQEQ-UHFFFAOYSA-N furan-3-one Chemical group O=C1COC=C1 LYINKTVZUSKQEQ-UHFFFAOYSA-N 0.000 claims description 21
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 239000011593 sulfur Substances 0.000 claims description 18
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 16
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 10
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 239000005864 Sulphur Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 7
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 claims description 7
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 5
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims description 4
- DMXFGVSTNVNKJF-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-3-(4-propan-2-ylphenyl)-1-oxaspiro[4.4]non-2-en-4-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)OC11CCCC1 DMXFGVSTNVNKJF-UHFFFAOYSA-N 0.000 claims description 4
- DPHNMQFIJICFJL-UHFFFAOYSA-N 3-(4-acetylphenyl)-2-(4-methylsulfonylphenyl)-1-oxaspiro[4.5]dec-2-en-4-one Chemical compound C1=CC(C(=O)C)=CC=C1C(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)OC11CCCCC1 DPHNMQFIJICFJL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 claims description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- PFWLGELXJMOEOK-UHFFFAOYSA-N 2,2-dimethyl-5-(4-methylsulfonylphenyl)-4-phenylfuran-3-one Chemical compound O=C1C(C)(C)OC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C1=CC=CC=C1 PFWLGELXJMOEOK-UHFFFAOYSA-N 0.000 claims description 3
- MTWACRKDNUVWOT-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-3-phenyl-1-oxaspiro[4.4]non-2-en-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(O1)=C(C=2C=CC=CC=2)C(=O)C11CCCC1 MTWACRKDNUVWOT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- YPMFTIAJMACOSF-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(4-methylsulfonylphenyl)-1,8-dioxaspiro[4.5]dec-2-en-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(O1)=C(C=2C=C(Cl)C=CC=2)C(=O)C11CCOCC1 YPMFTIAJMACOSF-UHFFFAOYSA-N 0.000 claims description 3
- INTSLNXNGISFFS-UHFFFAOYSA-N 3-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1-oxaspiro[4.5]dec-2-en-4-one Chemical compound CC1=CC=CC(C=2C(C3(CCCCC3)OC=2C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 INTSLNXNGISFFS-UHFFFAOYSA-N 0.000 claims description 3
- JZQRBJMAMIHLPH-UHFFFAOYSA-N 3-(4-acetylphenyl)-2-(4-methylsulfonylphenyl)-1-oxaspiro[4.4]non-2-en-4-one Chemical compound C1=CC(C(=O)C)=CC=C1C(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)OC11CCCC1 JZQRBJMAMIHLPH-UHFFFAOYSA-N 0.000 claims description 3
- UZMDRBXCKGDLMV-UHFFFAOYSA-N 4-(3-acetylphenyl)-2,2-dimethyl-5-(4-methylsulfonylphenyl)furan-3-one Chemical compound CC(=O)C1=CC=CC(C=2C(C(C)(C)OC=2C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 UZMDRBXCKGDLMV-UHFFFAOYSA-N 0.000 claims description 3
- NNFCIYWJLLJEMN-UHFFFAOYSA-N dec-2-en-4-one Chemical compound CCCCCCC(=O)C=CC NNFCIYWJLLJEMN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 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 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 2
- MPNAYBIVFGUCRJ-UHFFFAOYSA-N 2,2-diethyl-5-(4-methylsulfonylphenyl)-4-phenylfuran-3-one Chemical compound O=C1C(CC)(CC)OC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C1=CC=CC=C1 MPNAYBIVFGUCRJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 2
- RLLXAVJTMUKPET-UHFFFAOYSA-N 2,2-dimethyl-5-(4-methylsulfanylphenyl)-4-thiophen-3-ylfuran-3-one Chemical compound C1=CC(SC)=CC=C1C1=C(C2=CSC=C2)C(=O)C(C)(C)O1 RLLXAVJTMUKPET-UHFFFAOYSA-N 0.000 claims description 2
- MYHMXOXFHGBANN-UHFFFAOYSA-N 2,2-dimethyl-5-(4-methylsulfonylphenyl)-4-(3-nitrophenyl)furan-3-one Chemical compound O=C1C(C)(C)OC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C1=CC=CC([N+]([O-])=O)=C1 MYHMXOXFHGBANN-UHFFFAOYSA-N 0.000 claims description 2
- WIPSKZFMGOHWQN-UHFFFAOYSA-N 2,2-dimethyl-5-(4-methylsulfonylphenyl)-4-(4-propylphenyl)furan-3-one Chemical compound C1=CC(CCC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)OC(C)(C)C1=O WIPSKZFMGOHWQN-UHFFFAOYSA-N 0.000 claims description 2
- NVTBMWDRWUGZID-UHFFFAOYSA-N 2,2-dimethyl-5-(4-methylsulfonylphenyl)-4-pyridin-2-ylfuran-3-one Chemical compound O=C1C(C)(C)OC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C1=CC=CC=N1 NVTBMWDRWUGZID-UHFFFAOYSA-N 0.000 claims description 2
- DDXOZNQBBLORSF-UHFFFAOYSA-N 2,2-dimethyl-5-(4-methylsulfonylphenyl)-4-pyrimidin-5-ylfuran-3-one Chemical compound O=C1C(C)(C)OC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C1=CN=CN=C1 DDXOZNQBBLORSF-UHFFFAOYSA-N 0.000 claims description 2
- BENGSGPWRHSAHX-UHFFFAOYSA-N 2,2-dimethyl-5-(4-methylsulfonylphenyl)-4-thiophen-3-ylfuran-3-one Chemical compound O=C1C(C)(C)OC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C=1C=CSC=1 BENGSGPWRHSAHX-UHFFFAOYSA-N 0.000 claims description 2
- ZWQMFKLUSVRFAD-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-3-phenyl-1,8-dioxaspiro[4.5]dec-2-en-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(O1)=C(C=2C=CC=CC=2)C(=O)C11CCOCC1 ZWQMFKLUSVRFAD-UHFFFAOYSA-N 0.000 claims description 2
- GXIUOBUVBCHPBW-UHFFFAOYSA-N 2-bromo-4-[3-(3-fluorophenyl)-5,5-dimethyl-4-oxofuran-2-yl]benzenesulfonamide Chemical compound O=C1C(C)(C)OC(C=2C=C(Br)C(=CC=2)S(N)(=O)=O)=C1C1=CC=CC(F)=C1 GXIUOBUVBCHPBW-UHFFFAOYSA-N 0.000 claims description 2
- QKHJLAMJWWSUNE-UHFFFAOYSA-N 2-chloro-4-(5,5-dimethyl-4-oxo-3-phenylfuran-2-yl)benzenesulfonamide Chemical compound O=C1C(C)(C)OC(C=2C=C(Cl)C(=CC=2)S(N)(=O)=O)=C1C1=CC=CC=C1 QKHJLAMJWWSUNE-UHFFFAOYSA-N 0.000 claims description 2
- CPPLZMBUZWKADE-UHFFFAOYSA-N 2-chloro-4-[3-(2,5-difluorophenyl)-5,5-dimethyl-4-oxofuran-2-yl]benzenesulfonamide Chemical compound O=C1C(C)(C)OC(C=2C=C(Cl)C(=CC=2)S(N)(=O)=O)=C1C1=CC(F)=CC=C1F CPPLZMBUZWKADE-UHFFFAOYSA-N 0.000 claims description 2
- KHYMGNFKHYJBHT-UHFFFAOYSA-N 2-ethyl-2-methyl-5-(4-methylsulfonylphenyl)-4-phenylfuran-3-one Chemical compound O=C1C(CC)(C)OC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C1=CC=CC=C1 KHYMGNFKHYJBHT-UHFFFAOYSA-N 0.000 claims description 2
- HKWUJVQBIHIVSM-UHFFFAOYSA-N 2-fluoro-4-[3-(2-fluorophenyl)-5,5-dimethyl-4-oxofuran-2-yl]benzenesulfonamide Chemical compound O=C1C(C)(C)OC(C=2C=C(F)C(=CC=2)S(N)(=O)=O)=C1C1=CC=CC=C1F HKWUJVQBIHIVSM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- XFALLWUTEJUDPQ-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-(4-methylsulfonylphenyl)-1-oxaspiro[4.4]non-2-en-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(O1)=C(C=2C(=CC=CC=2)F)C(=O)C11CCCC1 XFALLWUTEJUDPQ-UHFFFAOYSA-N 0.000 claims description 2
- POADZBPKFUNRTF-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-2-(4-methylsulfonylphenyl)-1,8-dioxaspiro[4.5]dec-2-en-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(O1)=C(C=2C=C(F)C=C(F)C=2)C(=O)C11CCOCC1 POADZBPKFUNRTF-UHFFFAOYSA-N 0.000 claims description 2
- RSGRKGMCRNCVJN-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-2-(4-methylsulfonylphenyl)-1-oxaspiro[4.4]non-2-en-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(O1)=C(C=2C=C(F)C=C(F)C=2)C(=O)C11CCCC1 RSGRKGMCRNCVJN-UHFFFAOYSA-N 0.000 claims description 2
- WIGLMUDDMATVRD-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(4-methylsulfonylphenyl)-1-oxaspiro[4.4]non-2-en-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(O1)=C(C=2C=C(Cl)C=CC=2)C(=O)C11CCCC1 WIGLMUDDMATVRD-UHFFFAOYSA-N 0.000 claims description 2
- ZTKRIJHGXQFXOU-UHFFFAOYSA-N 3-(3-fluorophenyl)-2-(4-methylsulfonylphenyl)-1-oxaspiro[4.4]non-2-en-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(O1)=C(C=2C=C(F)C=CC=2)C(=O)C11CCCC1 ZTKRIJHGXQFXOU-UHFFFAOYSA-N 0.000 claims description 2
- XGAJAYPFTLAZNP-UHFFFAOYSA-N 3-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1-oxaspiro[4.4]non-2-en-4-one Chemical compound CC1=CC=CC(C=2C(C3(CCCC3)OC=2C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 XGAJAYPFTLAZNP-UHFFFAOYSA-N 0.000 claims description 2
- GUQCNEFTHHZZGQ-UHFFFAOYSA-N 3-(4-acetyl-3-fluorophenyl)-2-(4-methylsulfonylphenyl)-1-oxaspiro[4.4]non-2-en-4-one Chemical compound C1=C(F)C(C(=O)C)=CC=C1C(C1=O)=C(C=2C=CC(=CC=2)S(C)(=O)=O)OC11CCCC1 GUQCNEFTHHZZGQ-UHFFFAOYSA-N 0.000 claims description 2
- SBCNOGDXJUMDLX-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)-1-oxaspiro[4.4]non-2-en-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(O1)=C(C=2C=CC(F)=CC=2)C(=O)C11CCCC1 SBCNOGDXJUMDLX-UHFFFAOYSA-N 0.000 claims description 2
- HHMVFGUBICCSIY-UHFFFAOYSA-N 3-[5,5-dimethyl-2-(4-methylsulfonylphenyl)-4-oxofuran-3-yl]benzaldehyde Chemical compound O=C1C(C)(C)OC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C1=CC=CC(C=O)=C1 HHMVFGUBICCSIY-UHFFFAOYSA-N 0.000 claims description 2
- GSDBNJLRIWFPLE-UHFFFAOYSA-N 4-(3-chloro-4-propan-2-ylphenyl)-2-ethyl-2-methyl-5-(4-methylsulfonylphenyl)furan-3-one Chemical compound O=C1C(CC)(C)OC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C1=CC=C(C(C)C)C(Cl)=C1 GSDBNJLRIWFPLE-UHFFFAOYSA-N 0.000 claims description 2
- PSWLRFRODUGNDV-UHFFFAOYSA-N 4-(4-acetyl-3-chlorophenyl)-2-ethyl-2-methyl-5-(4-methylsulfonylphenyl)furan-3-one Chemical compound O=C1C(CC)(C)OC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C1=CC=C(C(C)=O)C(Cl)=C1 PSWLRFRODUGNDV-UHFFFAOYSA-N 0.000 claims description 2
- HCTGDGRMXGPXOR-UHFFFAOYSA-N 4-(4-chlorophenyl)-2,2-dimethyl-5-(4-methylsulfonylphenyl)furan-3-one Chemical compound O=C1C(C)(C)OC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C1=CC=C(Cl)C=C1 HCTGDGRMXGPXOR-UHFFFAOYSA-N 0.000 claims description 2
- CRELLWPBEKJIJW-UHFFFAOYSA-N 4-(5,5-dimethyl-3-naphthalen-1-yl-4-oxofuran-2-yl)benzenesulfonamide Chemical compound C=1C=CC2=CC=CC=C2C=1C=1C(=O)C(C)(C)OC=1C1=CC=C(S(N)(=O)=O)C=C1 CRELLWPBEKJIJW-UHFFFAOYSA-N 0.000 claims description 2
- HVMXZCNZQKVXKF-UHFFFAOYSA-N 4-(5-ethyl-5-methyl-4-oxo-3-phenylfuran-2-yl)benzenesulfonamide Chemical compound O=C1C(CC)(C)OC(C=2C=CC(=CC=2)S(N)(=O)=O)=C1C1=CC=CC=C1 HVMXZCNZQKVXKF-UHFFFAOYSA-N 0.000 claims description 2
- IGLGRIJFEHGSAV-UHFFFAOYSA-N 4-[3-(2-chlorophenyl)-5,5-dimethyl-4-oxofuran-2-yl]-2-fluorobenzenesulfonamide Chemical compound O=C1C(C)(C)OC(C=2C=C(F)C(=CC=2)S(N)(=O)=O)=C1C1=CC=CC=C1Cl IGLGRIJFEHGSAV-UHFFFAOYSA-N 0.000 claims description 2
- XSNLPJFSYUYAEY-UHFFFAOYSA-N 4-[3-(3,4-difluorophenyl)-5-ethyl-5-methyl-4-oxofuran-2-yl]benzenesulfonamide Chemical compound O=C1C(CC)(C)OC(C=2C=CC(=CC=2)S(N)(=O)=O)=C1C1=CC=C(F)C(F)=C1 XSNLPJFSYUYAEY-UHFFFAOYSA-N 0.000 claims description 2
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- C07—ORGANIC CHEMISTRY
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P27/00—Drugs for disorders of the senses
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- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019990013170A KR20000066223A (ko) | 1999-04-14 | 1999-04-14 | 디아릴-3(2h)퓨라논 유도체 및 이를 함유하는 시클로옥시게네이즈-2 저해제 조성물 |
KR1019990029779A KR20010010728A (ko) | 1999-07-22 | 1999-07-22 | 2,2-디알킬-4,5-디아릴-3(2h)퓨라논의 유도체 및 이를 함유하는 시클로옥시게네이즈-2 저해제 조성물 |
KR1019990039043A KR20010027342A (ko) | 1999-09-13 | 1999-09-13 | 2,2-디알킬-4,5-디아릴-3(2h)퓨라논의 술폰아마이드 유도체 및 이를 함유하는 시클로옥시게네이즈-2 저해제 조성물 |
KR1020000016866A KR20010094519A (ko) | 2000-03-31 | 2000-03-31 | 2,2,4,5-사중 치환된 3(2h)-퓨라논 유도체의 제조 방법 |
KR1020000017647A KR20010094161A (ko) | 2000-04-04 | 2000-04-04 | 2,2-디메틸-4,5-디아릴-3(2h)퓨라논의 유도체 및 이를함유하는 선택적인 시클로옥시게네이즈-2 저해제로서약제학적 조성물 |
PCT/KR2000/000339 WO2000061571A1 (en) | 1999-04-14 | 2000-04-12 | 4,5-diaryl-3(2h)-furanone derivatives as cyclooxygenase-2 inhibitors |
Publications (3)
Publication Number | Publication Date |
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NO20014986D0 NO20014986D0 (no) | 2001-10-12 |
NO20014986L NO20014986L (no) | 2001-11-01 |
NO327814B1 true NO327814B1 (no) | 2009-09-28 |
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NO20014986A NO327814B1 (no) | 1999-04-14 | 2001-10-12 | 4,5-diaryl-3(2H)-furanonderivater, fremgangsmate for fremstilling derav, farmasoytiske preparater samt anvendelse av slike derivater |
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EP (1) | EP1109799B1 (pt) |
JP (1) | JP3844657B2 (pt) |
KR (1) | KR20010111584A (pt) |
CN (1) | CN1166658C (pt) |
AT (1) | ATE256672T1 (pt) |
AU (1) | AU767811B2 (pt) |
BR (1) | BRPI0011172B8 (pt) |
CA (1) | CA2369979C (pt) |
CZ (1) | CZ300766B6 (pt) |
DE (1) | DE60007267T2 (pt) |
DZ (1) | DZ3265A1 (pt) |
EA (1) | EA004432B1 (pt) |
ES (1) | ES2213007T3 (pt) |
HK (1) | HK1046413B (pt) |
HU (1) | HU227863B1 (pt) |
IL (2) | IL145305A0 (pt) |
MA (1) | MA25406A1 (pt) |
MX (1) | MXPA01010312A (pt) |
NO (1) | NO327814B1 (pt) |
NZ (1) | NZ514101A (pt) |
PL (1) | PL204249B1 (pt) |
PT (1) | PT1109799E (pt) |
SK (1) | SK286314B6 (pt) |
TR (1) | TR200102958T2 (pt) |
WO (1) | WO2000061571A1 (pt) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
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KR20000066223A (ko) * | 1999-04-14 | 2000-11-15 | 서경배 | 디아릴-3(2h)퓨라논 유도체 및 이를 함유하는 시클로옥시게네이즈-2 저해제 조성물 |
KR20010010728A (ko) * | 1999-07-22 | 2001-02-15 | 서경배 | 2,2-디알킬-4,5-디아릴-3(2h)퓨라논의 유도체 및 이를 함유하는 시클로옥시게네이즈-2 저해제 조성물 |
KR20010094161A (ko) * | 2000-04-04 | 2001-10-31 | 서경배 | 2,2-디메틸-4,5-디아릴-3(2h)퓨라논의 유도체 및 이를함유하는 선택적인 시클로옥시게네이즈-2 저해제로서약제학적 조성물 |
MXPA03000161A (es) * | 2000-05-22 | 2004-02-26 | Reddy Research Foundation | Compuestos novedosos los cuales tienen actividad antiinflamatoria, proceso para su preparacion y composiciones farmaceuticas que las contienen. |
CN100588395C (zh) | 2000-06-13 | 2010-02-10 | Wyeth公司 | 含有环氧化酶-2抑制剂的止痛和抗炎药物 |
US20030105144A1 (en) | 2001-04-17 | 2003-06-05 | Ping Gao | Stabilized oral pharmaceutical composition |
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US7041280B2 (en) | 2001-06-29 | 2006-05-09 | Genzyme Corporation | Aryl boronate functionalized polymers for treating obesity |
WO2003018575A1 (en) * | 2001-08-24 | 2003-03-06 | Wyeth Holdings Corporation | 5-substituted-3(2h)-furanones useful for inhibition of farnesyl-protein transferase |
US6667330B2 (en) * | 2002-01-31 | 2003-12-23 | Galileo Pharmaceuticals, Inc. | Furanone derivatives |
ES2213485B1 (es) * | 2003-02-13 | 2005-12-16 | Almirall Prodesfarma, S.A. | Derivados de la 2-fenilpiran-4-ona. |
ES2214129B1 (es) * | 2003-02-13 | 2005-12-01 | Almirall Prodesfarma, S.A. | 3-fenilfuran-2-onas. |
ES2214130B1 (es) * | 2003-02-13 | 2005-12-01 | Almirall Prodesfarma, S.A. | 2-3'-bipiridinas. |
US20040220155A1 (en) * | 2003-03-28 | 2004-11-04 | Pharmacia Corporation | Method of providing a steroid-sparing benefit with a cyclooxygenase-2 inhibitor and compositions therewith |
WO2005009342A2 (en) * | 2003-07-16 | 2005-02-03 | Pharmacia Corporation | Method for the treatment or prevention of dermatological disorders with a cyclooxygenase-2 inhibitor alone and in combination with a dermatological treatment agent and compositions therewith |
US20050119262A1 (en) * | 2003-08-21 | 2005-06-02 | Pharmacia Corporation | Method for preventing or treating an optic neuropathy with a cox-2 inhibitor and an intraocular pressure reducing agent |
US20050113409A1 (en) * | 2003-09-03 | 2005-05-26 | Pharmacia Corporation | Method for the prevention or treatment of pain, inflammation and inflammation-related disorders with a Cox-2 selective inhibitor in combination with a nitric oxide-donating agent and compositions therewith |
JP4641772B2 (ja) * | 2003-10-23 | 2011-03-02 | 長谷川香料株式会社 | フラノンの製造方法 |
WO2005094815A1 (en) * | 2004-03-30 | 2005-10-13 | Amorepacific Corporation | Dual inhibition of cyclooxygenase-2 and carbonic anhydrase |
WO2007052937A2 (en) * | 2005-11-02 | 2007-05-10 | Amorepacific Corporation | Dosing regimens for cox-2 inhibitor |
EP2032147A4 (en) * | 2006-04-28 | 2011-02-02 | Cambridge Scient Pty Ltd | INHIBITOR OF COX-2 ENZYME |
WO2008094574A2 (en) * | 2007-01-30 | 2008-08-07 | Biogen Idec Ma Inc. | Furanone compounds and methods of making and using the same |
TWI634114B (zh) * | 2013-05-08 | 2018-09-01 | 永恒生物科技公司 | 作為激酶抑制劑之呋喃酮化合物 |
WO2015080435A1 (ko) * | 2013-11-26 | 2015-06-04 | 화일약품주식회사 | 4-(3-(3-플루오로페닐)-5,5-디메틸-4-옥소-4,5-디하이드로푸란-2-일)벤젠설폰아마이드의 제조 방법 |
KR101446601B1 (ko) * | 2014-01-29 | 2014-10-07 | 크리스탈지노믹스(주) | 5-(4-(아미노설포닐)페닐)-2,2-디메틸-4-(3-플루오로페닐)-3(2h)-퓨라논을 포함하는 약학적 조성물 및 캡슐 제형 |
US10413520B2 (en) | 2014-01-29 | 2019-09-17 | Crystalgenomics, Inc. | Oral pharmacological composition including 5-{4-(amino sulfonyl)phenyl}-2,2-dimethyl-4-(3-fluorophenyl)-3(2H)-furanone having crystalline structure with excellent stability |
CN104926797B (zh) * | 2014-06-10 | 2019-04-16 | 北京元博方医药科技有限公司 | 呋喃酮衍生物、制备方法及用途 |
CN104098535A (zh) * | 2014-07-25 | 2014-10-15 | 南通市华峰化工有限责任公司 | 一种4-(3-氟苯基)-2,2-二甲基-5-(4-(甲硫基)苯基)呋喃-3(2h)-酮的制备方法 |
RU2563876C1 (ru) * | 2014-11-11 | 2015-09-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Санкт-Петербургский государственный университет" (СПбГУ) | Способ получения 2,2-диалкил-4,5-диарилфуран-3(2н)-онов |
CN106866558B (zh) * | 2015-08-21 | 2019-07-30 | 宁波百思佳医药科技有限公司 | 酰基三氮唑类化合物及其制备方法和应用 |
RU2631317C1 (ru) * | 2016-05-13 | 2017-09-21 | Общество с ограниченной ответственностью "Органик Эмиттерс" | Селективные ингибиторы циклооксигеназы и способ их получения |
CN111303085B (zh) * | 2020-03-13 | 2022-04-01 | 西安瑞联新材料股份有限公司 | 5-溴-2,2-二甲基-5-(4-甲磺酰基苯基)呋喃-3(2h)-酮的合成方法 |
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JPS63313719A (ja) * | 1987-06-15 | 1988-12-21 | T Hasegawa Co Ltd | 香料組成物 |
JPH0745483B2 (ja) * | 1987-09-26 | 1995-05-17 | 長谷川香料株式会社 | フラノン類の製造方法 |
JPH0825864B2 (ja) * | 1988-12-16 | 1996-03-13 | 長谷川香料株式会社 | 柴外線吸収剤 |
US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
EP0799218B1 (en) * | 1994-12-21 | 2003-02-19 | Merck Frosst Canada & Co. | Diaryl-2-(5h)-furanones as cox-2 inhibitors |
US5698585A (en) * | 1995-04-13 | 1997-12-16 | Kikkoman Corporation | Pharmaceutical preparation for prevention and/or treatment for cataract |
UA57002C2 (uk) * | 1995-10-13 | 2003-06-16 | Мерк Фросст Кенада Енд Ко./Мерк Фросст Кенада Енд Сі. | Похідне (метилсульфоніл)феніл-2-(5н)-фуранону, фармацевтична композиція та спосіб лікування |
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- 2000-04-12 WO PCT/KR2000/000339 patent/WO2000061571A1/en active IP Right Grant
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