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 PDF

Info

Publication number: NO327814B1
Authority: NO; Norway
Prior art keywords: phenyl; dimethyl; methylsulfonyl; furanone; aminosulfonyl
Prior art date: 1999-04-14

Application number

NO20014986A

Other languages

English (en)

Norwegian (no)

Other versions

NO20014986L (no

NO20014986D0 (no

Inventor

Song Seok Shin

Min-Soo Noh

Young Joo Byun

Jin Kyu Choi

Jin Kwan Kim

Kyung Min Lim

Ji Young Kim

Young Hoon Choi

Jun-Yong Ha

Ki-Wha Lee

Joo Hyun Moh

Yeon Su Jeong

Shin Chung

Yung Hyup Joo

Chang Hoon Lee

Seon Hwa Kang

Young-Ho Park

Jung Bum Yl

Original Assignee

Pacific Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-04-14

Filing date

2001-10-12

Publication date

2009-09-28

1999-04-14 Priority claimed from KR1019990013170A external-priority patent/KR20000066223A/ko

1999-07-22 Priority claimed from KR1019990029779A external-priority patent/KR20010010728A/ko

1999-09-13 Priority claimed from KR1019990039043A external-priority patent/KR20010027342A/ko

2000-03-31 Priority claimed from KR1020000016866A external-priority patent/KR20010094519A/ko

2000-04-04 Priority claimed from KR1020000017647A external-priority patent/KR20010094161A/ko

2001-10-12 Application filed by Pacific Corp filed Critical Pacific Corp

2001-10-12 Publication of NO20014986D0 publication Critical patent/NO20014986D0/no

2001-11-01 Publication of NO20014986L publication Critical patent/NO20014986L/no

2009-09-28 Publication of NO327814B1 publication Critical patent/NO327814B1/no

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
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Classifications

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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—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
- 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
- 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
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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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
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- 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
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- 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
- C07D307/58—One oxygen atom, e.g. butenolide
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- 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
- C07D307/64—Sulfur atoms
- 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
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems

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NO20014986A 1999-04-14 2001-10-12 4,5-diaryl-3(2H)-furanonderivater, fremgangsmate for fremstilling derav, farmasoytiske preparater samt anvendelse av slike derivater NO327814B1 (no)

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 (fr)	1999-04-14	2000-04-12	Derives de 4,5-diaryl-3(2h)-furanone comme inhibiteurs de cyclo-oxygenase-2

Publications (3)

Publication Number	Publication Date
NO20014986D0 NO20014986D0 (no)	2001-10-12
NO20014986L NO20014986L (no)	2001-11-01
NO327814B1 true NO327814B1 (no)	2009-09-28

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ID=27532305

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Application Number	Title	Priority Date	Filing Date
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

Country Status (26)

Country	Link
US (1)	US6492416B1 (fr)
EP (1)	EP1109799B1 (fr)
JP (1)	JP3844657B2 (fr)
KR (1)	KR20010111584A (fr)
CN (1)	CN1166658C (fr)
AT (1)	ATE256672T1 (fr)
AU (1)	AU767811B2 (fr)
BR (1)	BRPI0011172B8 (fr)
CA (1)	CA2369979C (fr)
CZ (1)	CZ300766B6 (fr)
DE (1)	DE60007267T2 (fr)
DZ (1)	DZ3265A1 (fr)
EA (1)	EA004432B1 (fr)
ES (1)	ES2213007T3 (fr)
HK (1)	HK1046413B (fr)
HU (1)	HU227863B1 (fr)
IL (2)	IL145305A0 (fr)
MA (1)	MA25406A1 (fr)
MX (1)	MXPA01010312A (fr)
NO (1)	NO327814B1 (fr)
NZ (1)	NZ514101A (fr)
PL (1)	PL204249B1 (fr)
PT (1)	PT1109799E (fr)
SK (1)	SK286314B6 (fr)
TR (1)	TR200102958T2 (fr)
WO (1)	WO2000061571A1 (fr)

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WO2005009342A2 (fr) *	2003-07-16	2005-02-03	Pharmacia Corporation	Methode de traitement ou de prevention de troubles dermatologiques a l'aide d'un seul inhibiteur de la cyclooxygenase-2 ou en combinaison avec un agent de traitement dermatologique, et compositions contenant ceux-ci
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WO2005023189A2 (fr) *	2003-09-03	2005-03-17	Pharmacia Corporation	Procede de prevention ou de traitement de la douleur, de l'inflammation, et de troubles lies a l'inflammation avec un inhibiteur selectif de cox-2 en combinaison avec un agent donneur de monoxyde d'azote et compositions en contenant
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 (fr) *	2004-03-30	2005-10-13	Amorepacific Corporation	Double inhibition de la cyclooxygenase 2 et de l'anhydrase carbonique
WO2007052937A2 (fr) *	2005-11-02	2007-05-10	Amorepacific Corporation	Regimes de dosage destines a l'inhibiteur cox-2
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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
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
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
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2000
- 2000-04-12 EP EP00921133A patent/EP1109799B1/fr not_active Expired - Lifetime
- 2000-04-12 KR KR1020017012902A patent/KR20010111584A/ko active Granted
- 2000-04-12 CZ CZ20013662A patent/CZ300766B6/cs not_active IP Right Cessation
- 2000-04-12 HU HU0200623A patent/HU227863B1/hu unknown
- 2000-04-12 CA CA002369979A patent/CA2369979C/fr not_active Expired - Lifetime
- 2000-04-12 HK HK02108027.8A patent/HK1046413B/zh not_active IP Right Cessation
- 2000-04-12 DZ DZ003265A patent/DZ3265A1/fr active
- 2000-04-12 PL PL351125A patent/PL204249B1/pl unknown
- 2000-04-12 IL IL14530500A patent/IL145305A0/xx active IP Right Grant
- 2000-04-12 PT PT00921133T patent/PT1109799E/pt unknown
- 2000-04-12 US US09/744,762 patent/US6492416B1/en not_active Expired - Lifetime
- 2000-04-12 ES ES00921133T patent/ES2213007T3/es not_active Expired - Lifetime
- 2000-04-12 BR BRPI0011172A patent/BRPI0011172B8/pt not_active IP Right Cessation
- 2000-04-12 DE DE60007267T patent/DE60007267T2/de not_active Expired - Lifetime
- 2000-04-12 NZ NZ514101A patent/NZ514101A/en not_active IP Right Cessation
- 2000-04-12 AU AU41480/00A patent/AU767811B2/en not_active Expired
- 2000-04-12 WO PCT/KR2000/000339 patent/WO2000061571A1/fr not_active Ceased
- 2000-04-12 CN CNB008062293A patent/CN1166658C/zh not_active Expired - Lifetime
- 2000-04-12 EA EA200100958A patent/EA004432B1/ru not_active IP Right Cessation
- 2000-04-12 SK SK1451-2001A patent/SK286314B6/sk not_active IP Right Cessation
- 2000-04-12 JP JP2000610845A patent/JP3844657B2/ja not_active Expired - Lifetime
- 2000-04-12 AT AT00921133T patent/ATE256672T1/de not_active IP Right Cessation
- 2000-04-12 TR TR2001/02958T patent/TR200102958T2/xx unknown
2001
- 2001-09-06 IL IL145305A patent/IL145305A/en not_active IP Right Cessation
- 2001-10-12 MA MA26357A patent/MA25406A1/fr unknown
- 2001-10-12 NO NO20014986A patent/NO327814B1/no not_active IP Right Cessation
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Also Published As

Publication number	Publication date
HUP0200623A3 (en)	2002-10-28
CA2369979A1 (fr)	2000-10-19
US6492416B1 (en)	2002-12-10
NO20014986L (no)	2001-11-01
DZ3265A1 (fr)	2000-10-19
NO20014986D0 (no)	2001-10-12
ES2213007T3 (es)	2004-08-16
EA200100958A1 (ru)	2002-06-27
HU0200623D0 (en)	2002-03-28
CZ20013662A3 (cs)	2002-02-13
PT1109799E (pt)	2004-05-31
WO2000061571A1 (fr)	2000-10-19
TR200102958T2 (tr)	2002-05-21
BRPI0011172B1 (pt)	2017-05-16
JP2002541251A (ja)	2002-12-03
JP3844657B2 (ja)	2006-11-15
CN1348447A (zh)	2002-05-08
CZ300766B6 (cs)	2009-08-05
EP1109799B1 (fr)	2003-12-17
SK14512001A3 (sk)	2002-04-04
BRPI0011172B8 (pt)	2021-05-25
CA2369979C (fr)	2009-12-08
ATE256672T1 (de)	2004-01-15
HUP0200623A2 (hu)	2002-07-29
MXPA01010312A (es)	2005-07-25
EA004432B1 (ru)	2004-04-29
CN1166658C (zh)	2004-09-15
PL204249B1 (pl)	2009-12-31
SK286314B6 (en)	2008-07-07
HK1046413A1 (en)	2003-01-10
DE60007267D1 (de)	2004-01-29
EP1109799A1 (fr)	2001-06-27
MA25406A1 (fr)	2002-04-01
AU767811B2 (en)	2003-11-27
NZ514101A (en)	2001-09-28
BR0011172A (pt)	2002-02-19
KR20010111584A (ko)	2001-12-19
HU227863B1 (en)	2012-05-29
PL351125A1 (en)	2003-03-24
HK1046413B (zh)	2005-05-27
AU4148000A (en)	2000-11-14
DE60007267T2 (de)	2004-09-16
IL145305A (en)	2006-10-31
IL145305A0 (en)	2002-06-30

Legal Events

Date	Code	Title	Description
2013-12-02	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
EP1109799B1 (fr)	2003-12-17	Derives de 4,5-diaryl-3(2h)-furanone comme inhibiteurs de cyclo-oxygenase-2
JP2977137B2 (ja)	1999-11-10	シクロオキシゲナーゼ−２阻害剤としてのフェニルヘテロ環
US6057319A (en)	2000-05-02	3,4-Diaryl-2-hydroxy-2,5-dihydrofurans as prodrugs to cox-2 inhibitors
CA2293952A1 (fr)	1994-07-21	Preparation d'esters et analogues de ces esters
JPH10504829A (ja)	1998-05-12	シクロオキシゲナーゼ−２阻害剤としてのジアリール複素二環
NO321042B1 (no)	2006-03-06	(Metylsulfonyl)fenyl-2-(5H)-furanoner, farmasoytiske preparater som omfatter forbindelsene, samt anvendelse av forbindelsene for fremstilling av medikamenter som COX-2 inhibitorer
AU706518B2 (en)	1999-06-17	Bisarylcyclobutene derivates as cyclooxygenase inhibitors
AU717146B2 (en)	2000-03-16	Novel furan diarylmethylidene derivatives, method for their preparation and therapeutical uses thereof
NO327987B1 (no)	2009-11-02	2-Fenylpyran-4-on derivater
ES2337794T3 (es)	2010-04-29	Inhibidores no nucleosidos de la transcriptasa inversa.
KR100495389B1 (ko)	2005-06-16	시클로옥시게네이즈-2 저해제로서의4,5-디아릴-3(2ｈ)-퓨라논 유도체
JP3490406B2 (ja)	2004-01-26	シクロオキシゲナーゼ−２阻害剤としてのフェニルヘテロ環
HU228070B1 (hu)	2012-09-28	4,5-Diaril-3(2H9-furanonszármazékok, mint a ciklooxigenáz-2 inhibitorai, diaril-oxaspiro-biciklusos származékok
JP2018538334A (ja)	2018-12-27	Ｔｒｐｍ８拮抗薬としての４−ヒドロキシ−２−フェニル−１，３−チアゾール−５−イルメタノン誘導体