NO20024393L - 2-fenylpyran-4-on-derivater - Google Patents
2-fenylpyran-4-on-derivater Download PDFInfo
- Publication number
- NO20024393L NO20024393L NO20024393A NO20024393A NO20024393L NO 20024393 L NO20024393 L NO 20024393L NO 20024393 A NO20024393 A NO 20024393A NO 20024393 A NO20024393 A NO 20024393A NO 20024393 L NO20024393 L NO 20024393L
- Authority
- NO
- Norway
- Prior art keywords
- group
- alkyl
- methanesulfonylphenyl
- formula
- pyran
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 148
- 125000000217 alkyl group Chemical group 0.000 claims description 123
- -1 trifluoromethyl- Chemical group 0.000 claims description 101
- 238000002360 preparation method Methods 0.000 claims description 73
- 238000000034 method Methods 0.000 claims description 70
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 16
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 11
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 206010061218 Inflammation Diseases 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000004054 inflammatory process Effects 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 6
- 206010037660 Pyrexia Diseases 0.000 claims description 6
- UOXRODFUOLJMSO-UHFFFAOYSA-N 3-(2,4-difluorophenoxy)-6-(hydroxymethyl)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C(=CC(F)=CC=2)F)C(=O)C=C(CO)O1 UOXRODFUOLJMSO-UHFFFAOYSA-N 0.000 claims description 5
- OETIMMSWPHDTTA-UHFFFAOYSA-N 3-(4-fluoro-2-methylphenoxy)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=C(F)C=C1C OETIMMSWPHDTTA-UHFFFAOYSA-N 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 229940127293 prostanoid Drugs 0.000 claims description 5
- 150000003814 prostanoids Chemical class 0.000 claims description 5
- 230000016160 smooth muscle contraction Effects 0.000 claims description 5
- KRFKBVRMCXACPL-UHFFFAOYSA-N 2-(difluoromethyl)-5-(2,4-difluorophenoxy)-3-methyl-6-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(F)C=C(F)C=1OC=1C(=O)C(C)=C(C(F)F)OC=1C1=CC=C(S(C)(=O)=O)C=C1 KRFKBVRMCXACPL-UHFFFAOYSA-N 0.000 claims description 4
- HZIMQUSOGVRMRT-UHFFFAOYSA-N 3-(4-bromo-2-fluorophenoxy)-6-(hydroxymethyl)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C(=CC(Br)=CC=2)F)C(=O)C=C(CO)O1 HZIMQUSOGVRMRT-UHFFFAOYSA-N 0.000 claims description 4
- JHQUVTCAOQVFBH-UHFFFAOYSA-N 3-(4-bromophenoxy)-6-(difluoromethyl)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(Br)=CC=2)C(=O)C=C(C(F)F)O1 JHQUVTCAOQVFBH-UHFFFAOYSA-N 0.000 claims description 4
- BEUSXCFVSULHCA-UHFFFAOYSA-N 3-(4-chlorophenoxy)-6-(hydroxymethyl)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(Cl)=CC=2)C(=O)C=C(CO)O1 BEUSXCFVSULHCA-UHFFFAOYSA-N 0.000 claims description 4
- XPNVQFBDBFNUDM-UHFFFAOYSA-N 3-(4-chlorophenoxy)-6-(methoxymethyl)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(COC)=CC(=O)C=1OC1=CC=C(Cl)C=C1 XPNVQFBDBFNUDM-UHFFFAOYSA-N 0.000 claims description 4
- SBRUXVDEMQJAFP-UHFFFAOYSA-N 3-(4-fluorophenoxy)-6-(hydroxymethyl)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(F)=CC=2)C(=O)C=C(CO)O1 SBRUXVDEMQJAFP-UHFFFAOYSA-N 0.000 claims description 4
- RGBUWQFPRPMUDZ-UHFFFAOYSA-N 3-(4-fluorophenoxy)-6-(methoxymethyl)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(COC)=CC(=O)C=1OC1=CC=C(F)C=C1 RGBUWQFPRPMUDZ-UHFFFAOYSA-N 0.000 claims description 4
- ODZXJBMBUAGGSS-UHFFFAOYSA-N 3-bromo-2-(difluoromethyl)-5-(2,4-difluorophenoxy)-6-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C(=CC(F)=CC=2)F)C(=O)C(Br)=C(C(F)F)O1 ODZXJBMBUAGGSS-UHFFFAOYSA-N 0.000 claims description 4
- BUVNUHAZLOLFFJ-UHFFFAOYSA-N 3-bromo-5-(4-chlorophenoxy)-2-methyl-6-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(Cl)C=CC=1OC=1C(=O)C(Br)=C(C)OC=1C1=CC=C(S(C)(=O)=O)C=C1 BUVNUHAZLOLFFJ-UHFFFAOYSA-N 0.000 claims description 4
- VRQFSFPNHQFPIE-UHFFFAOYSA-N 3-chloro-5-(2,4-difluorophenoxy)-2-methyl-6-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(F)C=C(F)C=1OC=1C(=O)C(Cl)=C(C)OC=1C1=CC=C(S(C)(=O)=O)C=C1 VRQFSFPNHQFPIE-UHFFFAOYSA-N 0.000 claims description 4
- HWJYVVCKPDYAMV-UHFFFAOYSA-N 3-chloro-5-(4-chlorophenoxy)-2-methyl-6-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(Cl)C=CC=1OC=1C(=O)C(Cl)=C(C)OC=1C1=CC=C(S(C)(=O)=O)C=C1 HWJYVVCKPDYAMV-UHFFFAOYSA-N 0.000 claims description 4
- ICMSGBUGGUXQQI-UHFFFAOYSA-N 5-(2,4-difluorophenoxy)-2,3-dimethyl-6-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(F)C=C(F)C=1OC=1C(=O)C(C)=C(C)OC=1C1=CC=C(S(C)(=O)=O)C=C1 ICMSGBUGGUXQQI-UHFFFAOYSA-N 0.000 claims description 4
- AQJZPWCLCJWGFK-UHFFFAOYSA-N 5-(2,4-difluorophenoxy)-2-ethyl-3-methyl-6-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(F)C=C(F)C=1OC=1C(=O)C(C)=C(CC)OC=1C1=CC=C(S(C)(=O)=O)C=C1 AQJZPWCLCJWGFK-UHFFFAOYSA-N 0.000 claims description 4
- RLGNMIDASULXKL-UHFFFAOYSA-N 5-(2,4-difluorophenoxy)-3-ethenyl-2-methyl-6-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(F)C=C(F)C=1OC=1C(=O)C(C=C)=C(C)OC=1C1=CC=C(S(C)(=O)=O)C=C1 RLGNMIDASULXKL-UHFFFAOYSA-N 0.000 claims description 4
- DZSILQIXYOZOKN-UHFFFAOYSA-N 5-(2,4-difluorophenoxy)-3-ethyl-2-methyl-6-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(F)C=C(F)C=1OC=1C(=O)C(CC)=C(C)OC=1C1=CC=C(S(C)(=O)=O)C=C1 DZSILQIXYOZOKN-UHFFFAOYSA-N 0.000 claims description 4
- ISESFZQITYBRSI-UHFFFAOYSA-N 5-(2,4-difluorophenoxy)-6-(4-methylsulfonylphenyl)-4-oxopyran-2-carboxylic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C(=CC(F)=CC=2)F)C(=O)C=C(C(O)=O)O1 ISESFZQITYBRSI-UHFFFAOYSA-N 0.000 claims description 4
- NYPDNQOXSBKAQW-UHFFFAOYSA-N 5-(4-chlorophenoxy)-6-(4-methylsulfonylphenyl)-4-oxopyran-2-carboxylic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C=CC(Cl)=CC=2)C(=O)C=C(C(O)=O)O1 NYPDNQOXSBKAQW-UHFFFAOYSA-N 0.000 claims description 4
- OEAXYUHTGDWJIK-UHFFFAOYSA-N 6-(difluoromethyl)-3-(2,4-difluorophenoxy)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(OC=2C(=CC(F)=CC=2)F)C(=O)C=C(C(F)F)O1 OEAXYUHTGDWJIK-UHFFFAOYSA-N 0.000 claims description 4
- ZSGDYBFTFRRKPD-UHFFFAOYSA-N 6-(difluoromethyl)-3-(4-methylphenoxy)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C1=CC(C)=CC=C1OC1=C(C=2C=CC(=CC=2)S(C)(=O)=O)OC(C(F)F)=CC1=O ZSGDYBFTFRRKPD-UHFFFAOYSA-N 0.000 claims description 4
- QFGVWVQHHYWJKM-UHFFFAOYSA-N 6-methyl-3-(2-methylphenoxy)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=CC=C1C QFGVWVQHHYWJKM-UHFFFAOYSA-N 0.000 claims description 4
- RTHQRIZEGPCCGE-UHFFFAOYSA-N 6-methyl-3-(3-methylphenoxy)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound CC1=CC=CC(OC=2C(C=C(C)OC=2C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 RTHQRIZEGPCCGE-UHFFFAOYSA-N 0.000 claims description 4
- HDTJKCFXYMUHAK-UHFFFAOYSA-N [5-(2,4-difluorophenoxy)-6-(4-methylsulfonylphenyl)-4-oxopyran-2-yl]methyl acetate Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(COC(=O)C)=CC(=O)C=1OC1=CC=C(F)C=C1F HDTJKCFXYMUHAK-UHFFFAOYSA-N 0.000 claims description 4
- UFXBWNALEHHQFP-UHFFFAOYSA-N [5-(4-chlorophenoxy)-6-(4-methylsulfonylphenyl)-4-oxopyran-2-yl]methyl acetate Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(COC(=O)C)=CC(=O)C=1OC1=CC=C(Cl)C=C1 UFXBWNALEHHQFP-UHFFFAOYSA-N 0.000 claims description 4
- RQQOJQGCCQYSLO-UHFFFAOYSA-N [5-(4-fluorophenoxy)-6-(4-methylsulfonylphenyl)-4-oxopyran-2-yl]methyl acetate Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(COC(=O)C)=CC(=O)C=1OC1=CC=C(F)C=C1 RQQOJQGCCQYSLO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- AFXJOGTTYJOEFU-UHFFFAOYSA-N 3-(2,4-dibromophenoxy)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=C(Br)C=C1Br AFXJOGTTYJOEFU-UHFFFAOYSA-N 0.000 claims description 3
- QCFSNFXCEXHHCL-UHFFFAOYSA-N 3-(2,4-difluorophenoxy)-2-(4-ethylsulfonylphenyl)-6-methylpyran-4-one Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C1=C(OC=2C(=CC(F)=CC=2)F)C(=O)C=C(C)O1 QCFSNFXCEXHHCL-UHFFFAOYSA-N 0.000 claims description 3
- DFQHKIXVIYDTGY-UHFFFAOYSA-N 3-(2,4-difluorophenoxy)-6-(methoxymethyl)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(COC)=CC(=O)C=1OC1=CC=C(F)C=C1F DFQHKIXVIYDTGY-UHFFFAOYSA-N 0.000 claims description 3
- WBEBBJFBRLUVMQ-UHFFFAOYSA-N 3-(2-bromophenoxy)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=CC=C1Br WBEBBJFBRLUVMQ-UHFFFAOYSA-N 0.000 claims description 3
- DUSGGEPBMGVOMH-UHFFFAOYSA-N 3-(2-chloro-4-methylphenoxy)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound ClC1=CC(C)=CC=C1OC1=C(C=2C=CC(=CC=2)S(C)(=O)=O)OC(C)=CC1=O DUSGGEPBMGVOMH-UHFFFAOYSA-N 0.000 claims description 3
- JAIOAMPOGJIYQK-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenoxy)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound FC1=CC(C)=CC=C1OC1=C(C=2C=CC(=CC=2)S(C)(=O)=O)OC(C)=CC1=O JAIOAMPOGJIYQK-UHFFFAOYSA-N 0.000 claims description 3
- AQKBTKCEELLTSZ-UHFFFAOYSA-N 3-(3-bromophenoxy)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=CC(Br)=C1 AQKBTKCEELLTSZ-UHFFFAOYSA-N 0.000 claims description 3
- DPYLMVIJRWFZIG-UHFFFAOYSA-N 3-(4-bromo-2-chlorophenoxy)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=C(Br)C=C1Cl DPYLMVIJRWFZIG-UHFFFAOYSA-N 0.000 claims description 3
- SGZPDQDNNJQFNW-UHFFFAOYSA-N 3-(4-bromo-2-fluorophenoxy)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=C(Br)C=C1F SGZPDQDNNJQFNW-UHFFFAOYSA-N 0.000 claims description 3
- DICHKUSVPRXKBB-UHFFFAOYSA-N 3-(4-chloro-2-methylphenoxy)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=C(Cl)C=C1C DICHKUSVPRXKBB-UHFFFAOYSA-N 0.000 claims description 3
- MFPZGTHLTRZKEO-UHFFFAOYSA-N 3-bromo-5-(2,4-difluorophenoxy)-2-methyl-6-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(F)C=C(F)C=1OC=1C(=O)C(Br)=C(C)OC=1C1=CC=C(S(C)(=O)=O)C=C1 MFPZGTHLTRZKEO-UHFFFAOYSA-N 0.000 claims description 3
- VMYMVQUKYUNQHW-UHFFFAOYSA-N 3-chloro-5-(4-fluorophenoxy)-2-methyl-6-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(F)C=CC=1OC=1C(=O)C(Cl)=C(C)OC=1C1=CC=C(S(C)(=O)=O)C=C1 VMYMVQUKYUNQHW-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 238000006264 debenzylation reaction Methods 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 125
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
- 239000007787 solid Substances 0.000 description 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000004440 column chromatography Methods 0.000 description 25
- 239000000741 silica gel Substances 0.000 description 25
- 229910002027 silica gel Inorganic materials 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000003480 eluent Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- 238000004519 manufacturing process Methods 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- UFECLJRYNAOWOI-UHFFFAOYSA-N 2-phenylpyran-4-one Chemical class O=C1C=COC(C=2C=CC=CC=2)=C1 UFECLJRYNAOWOI-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000000746 purification Methods 0.000 description 16
- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 14
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Classifications
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- C—CHEMISTRY; METALLURGY
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200000637 | 2000-03-16 | ||
| PCT/EP2001/003042 WO2001068633A1 (en) | 2000-03-16 | 2001-03-16 | 2-phenylpyran-4-one derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20024393D0 NO20024393D0 (no) | 2002-09-13 |
| NO20024393L true NO20024393L (no) | 2002-11-13 |
Family
ID=8492732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20024393A NO20024393L (no) | 2000-03-16 | 2002-09-13 | 2-fenylpyran-4-on-derivater |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7354936B2 (cs) |
| EP (1) | EP1263751B1 (cs) |
| JP (1) | JP2003527389A (cs) |
| KR (1) | KR20030005221A (cs) |
| CN (1) | CN1429221A (cs) |
| AR (1) | AR030410A1 (cs) |
| AT (1) | ATE269316T1 (cs) |
| AU (1) | AU2001254692A1 (cs) |
| BG (1) | BG107101A (cs) |
| BR (1) | BR0109252A (cs) |
| CA (1) | CA2403149A1 (cs) |
| CZ (1) | CZ20023058A3 (cs) |
| DE (1) | DE60103859T2 (cs) |
| EE (1) | EE200200528A (cs) |
| ES (1) | ES2223830T3 (cs) |
| HK (1) | HK1048117A1 (cs) |
| HU (1) | HUP0301696A2 (cs) |
| IL (1) | IL151598A0 (cs) |
| MX (1) | MXPA02009016A (cs) |
| NO (1) | NO20024393L (cs) |
| NZ (1) | NZ521187A (cs) |
| PE (1) | PE20011333A1 (cs) |
| PL (1) | PL358062A1 (cs) |
| RU (1) | RU2002127728A (cs) |
| SK (1) | SK12832002A3 (cs) |
| WO (1) | WO2001068633A1 (cs) |
| ZA (1) | ZA200207184B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6465509B2 (en) | 2000-06-30 | 2002-10-15 | Merck Frosst Canada & Co. | Pyrones as inhibitors of cyclooxygenase-2 |
| ES2213485B1 (es) * | 2003-02-13 | 2005-12-16 | Almirall Prodesfarma, S.A. | Derivados de la 2-fenilpiran-4-ona. |
| CN102731456B (zh) * | 2011-04-01 | 2014-07-09 | 华中科技大学 | 一种抗肿瘤化合物及其制备方法和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH524614A (de) | 1969-12-31 | 1972-06-30 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Imidazolderivaten |
| US3901908A (en) | 1970-12-28 | 1975-08-26 | Ciba Geigy Corp | 2-alkyl- and 2-cycloalkyl-4,5-bis-phenyl-imidazoles |
| US4304728A (en) | 1979-04-05 | 1981-12-08 | Lilly Industries Limited | 6-Substituted pyranone compounds and their use as pharmaceuticals |
| IL59748A (en) | 1979-04-05 | 1983-11-30 | Lilly Industries Ltd | 5-substituted pyranone derivatives,their production and pharmaceutical compositions containing them |
| US6048850A (en) | 1992-09-22 | 2000-04-11 | Young; Donald A. | Method of inhibiting prostaglandin synthesis in a human host |
| WO1995014014A2 (en) * | 1993-11-19 | 1995-05-26 | Parke, Davis & Company | Pyrone derivatives as protease inhibitors and antiviral agents |
| US5521213A (en) | 1994-08-29 | 1996-05-28 | Merck Frosst Canada, Inc. | Diaryl bicyclic heterocycles as inhibitors of cyclooxygenase-2 |
| US5541204A (en) | 1994-12-02 | 1996-07-30 | Bristol-Myers Squibb Company | Aryloxypropanolamine β 3 adrenergic agonists |
| EA199700209A1 (ru) | 1995-04-04 | 1998-04-30 | Глаксо Груп Лимитед | ПРОИЗВОДНЫЕ ИМИДАЗО[1,2-a]ПИРИДИНА |
| BR9813998A (pt) | 1997-11-19 | 2000-09-26 | Kowa Co | Novos derivados de piridazina e produtos medicinais contendo os mesmos como ingredientes efetivos |
| TW587079B (en) * | 1998-09-25 | 2004-05-11 | Almirall Prodesfarma Ag | 2-phenylpyran-4-one derivatives |
-
2001
- 2001-03-13 PE PE2001000241A patent/PE20011333A1/es not_active Application Discontinuation
- 2001-03-15 AR ARP010101221A patent/AR030410A1/es not_active Application Discontinuation
- 2001-03-16 AT AT01927742T patent/ATE269316T1/de not_active IP Right Cessation
- 2001-03-16 HU HU0301696A patent/HUP0301696A2/hu unknown
- 2001-03-16 NZ NZ521187A patent/NZ521187A/en unknown
- 2001-03-16 SK SK1283-2002A patent/SK12832002A3/sk unknown
- 2001-03-16 JP JP2001567725A patent/JP2003527389A/ja not_active Withdrawn
- 2001-03-16 CA CA002403149A patent/CA2403149A1/en not_active Abandoned
- 2001-03-16 RU RU2002127728/04A patent/RU2002127728A/ru not_active Application Discontinuation
- 2001-03-16 ES ES01927742T patent/ES2223830T3/es not_active Expired - Lifetime
- 2001-03-16 BR BR0109252-9A patent/BR0109252A/pt not_active IP Right Cessation
- 2001-03-16 PL PL01358062A patent/PL358062A1/xx not_active Application Discontinuation
- 2001-03-16 EE EEP200200528A patent/EE200200528A/xx unknown
- 2001-03-16 CN CN01809447A patent/CN1429221A/zh active Pending
- 2001-03-16 AU AU2001254692A patent/AU2001254692A1/en not_active Abandoned
- 2001-03-16 EP EP01927742A patent/EP1263751B1/en not_active Expired - Lifetime
- 2001-03-16 CZ CZ20023058A patent/CZ20023058A3/cs unknown
- 2001-03-16 MX MXPA02009016A patent/MXPA02009016A/es unknown
- 2001-03-16 KR KR1020027011875A patent/KR20030005221A/ko not_active Application Discontinuation
- 2001-03-16 WO PCT/EP2001/003042 patent/WO2001068633A1/en active IP Right Grant
- 2001-03-16 IL IL15159801A patent/IL151598A0/xx unknown
- 2001-03-16 DE DE60103859T patent/DE60103859T2/de not_active Expired - Lifetime
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2002
- 2002-09-06 ZA ZA200207184A patent/ZA200207184B/en unknown
- 2002-09-13 BG BG107101A patent/BG107101A/bg unknown
- 2002-09-13 NO NO20024393A patent/NO20024393L/no not_active Application Discontinuation
- 2002-09-16 US US10/245,873 patent/US7354936B2/en not_active Expired - Fee Related
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2003
- 2003-01-11 HK HK03100285.1A patent/HK1048117A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL358062A1 (en) | 2004-08-09 |
| HK1048117A1 (zh) | 2003-03-21 |
| CA2403149A1 (en) | 2001-09-20 |
| BR0109252A (pt) | 2002-12-24 |
| SK12832002A3 (sk) | 2003-11-04 |
| EE200200528A (et) | 2004-04-15 |
| WO2001068633A1 (en) | 2001-09-20 |
| EP1263751B1 (en) | 2004-06-16 |
| DE60103859D1 (de) | 2004-07-22 |
| MXPA02009016A (es) | 2004-10-15 |
| JP2003527389A (ja) | 2003-09-16 |
| BG107101A (bg) | 2003-07-31 |
| HUP0301696A2 (hu) | 2003-09-29 |
| US20030232880A1 (en) | 2003-12-18 |
| AR030410A1 (es) | 2003-08-20 |
| RU2002127728A (ru) | 2004-03-20 |
| CN1429221A (zh) | 2003-07-09 |
| DE60103859T2 (de) | 2005-07-21 |
| PE20011333A1 (es) | 2002-01-16 |
| AU2001254692A1 (en) | 2001-09-24 |
| KR20030005221A (ko) | 2003-01-17 |
| US7354936B2 (en) | 2008-04-08 |
| EP1263751A1 (en) | 2002-12-11 |
| CZ20023058A3 (cs) | 2004-01-14 |
| NO20024393D0 (no) | 2002-09-13 |
| ZA200207184B (en) | 2003-12-08 |
| ES2223830T3 (es) | 2005-03-01 |
| ATE269316T1 (de) | 2004-07-15 |
| NZ521187A (en) | 2004-03-26 |
| IL151598A0 (en) | 2003-04-10 |
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| FC2A | Withdrawal, rejection or dismissal of laid open patent application |