NO20024393L - 2-fenylpyran-4-on-derivater - Google Patents

2-fenylpyran-4-on-derivater Download PDF

Info

Publication number: NO20024393L
Authority: NO; Norway
Prior art keywords: group; alkyl; methanesulfonylphenyl; formula; pyran
Prior art date: 2000-03-16

Application number

NO20024393A

Other languages

English (en)

Norwegian (no)

Other versions

NO20024393D0 (no

Inventor

Maria Isabel Crespo Crespo

Juan Miguel Jimenez Mayorga

Josep Lluis Matallana Julia

Joan Feixas Gras

Original Assignee

Almirall Prodesfarma Ag

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.)

2000-03-16

Filing date

2002-09-13

Publication date

2002-11-13

2002-09-13 Application filed by Almirall Prodesfarma Ag filed Critical Almirall Prodesfarma Ag

2002-09-13 Publication of NO20024393D0 publication Critical patent/NO20024393D0/no

2002-11-13 Publication of NO20024393L publication Critical patent/NO20024393L/no

Links

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

- 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
- 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

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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)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyrane Compounds (AREA)

NO20024393A 2000-03-16 2002-09-13 2-fenylpyran-4-on-derivater NO20024393L (no)

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

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NO20024393D0 NO20024393D0 (no)	2002-09-13
NO20024393L true NO20024393L (no)	2002-11-13

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US (1)	US7354936B2 (pl)
EP (1)	EP1263751B1 (pl)
JP (1)	JP2003527389A (pl)
KR (1)	KR20030005221A (pl)
CN (1)	CN1429221A (pl)
AR (1)	AR030410A1 (pl)
AT (1)	ATE269316T1 (pl)
AU (1)	AU2001254692A1 (pl)
BG (1)	BG107101A (pl)
BR (1)	BR0109252A (pl)
CA (1)	CA2403149A1 (pl)
CZ (1)	CZ20023058A3 (pl)
DE (1)	DE60103859T2 (pl)
EE (1)	EE200200528A (pl)
ES (1)	ES2223830T3 (pl)
HK (1)	HK1048117A1 (pl)
HU (1)	HUP0301696A2 (pl)
IL (1)	IL151598A0 (pl)
MX (1)	MXPA02009016A (pl)
NO (1)	NO20024393L (pl)
NZ (1)	NZ521187A (pl)
PE (1)	PE20011333A1 (pl)
PL (1)	PL358062A1 (pl)
RU (1)	RU2002127728A (pl)
SK (1)	SK12832002A3 (pl)
WO (1)	WO2001068633A1 (pl)
ZA (1)	ZA200207184B (pl)

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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

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CH523257A (de)	1969-12-31	1972-05-31	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
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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 RU RU2002127728/04A patent/RU2002127728A/ru not_active Application Discontinuation
- 2001-03-16 BR BR0109252-9A patent/BR0109252A/pt not_active IP Right Cessation
- 2001-03-16 IL IL15159801A patent/IL151598A0/xx unknown
- 2001-03-16 MX MXPA02009016A patent/MXPA02009016A/es unknown
- 2001-03-16 JP JP2001567725A patent/JP2003527389A/ja not_active Withdrawn
- 2001-03-16 KR KR1020027011875A patent/KR20030005221A/ko not_active Withdrawn
- 2001-03-16 PL PL01358062A patent/PL358062A1/pl not_active Application Discontinuation
- 2001-03-16 CN CN01809447A patent/CN1429221A/zh active Pending
- 2001-03-16 DE DE60103859T patent/DE60103859T2/de not_active Expired - Lifetime
- 2001-03-16 EE EEP200200528A patent/EE200200528A/xx unknown
- 2001-03-16 NZ NZ521187A patent/NZ521187A/en unknown
- 2001-03-16 AU AU2001254692A patent/AU2001254692A1/en not_active Abandoned
- 2001-03-16 SK SK1283-2002A patent/SK12832002A3/sk unknown
- 2001-03-16 EP EP01927742A patent/EP1263751B1/en not_active Expired - Lifetime
- 2001-03-16 CA CA002403149A patent/CA2403149A1/en not_active Abandoned
- 2001-03-16 HU HU0301696A patent/HUP0301696A2/hu unknown
- 2001-03-16 WO PCT/EP2001/003042 patent/WO2001068633A1/en not_active Ceased
- 2001-03-16 ES ES01927742T patent/ES2223830T3/es not_active Expired - Lifetime
- 2001-03-16 CZ CZ20023058A patent/CZ20023058A3/cs unknown
- 2001-03-16 HK HK03100285.1A patent/HK1048117A1/zh unknown
- 2001-03-16 AT AT01927742T patent/ATE269316T1/de not_active IP Right Cessation
2002
- 2002-09-06 ZA ZA200207184A patent/ZA200207184B/en unknown
- 2002-09-13 NO NO20024393A patent/NO20024393L/no not_active Application Discontinuation
- 2002-09-13 BG BG107101A patent/BG107101A/bg unknown
- 2002-09-16 US US10/245,873 patent/US7354936B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP1263751B1 (en)	2004-06-16
US20030232880A1 (en)	2003-12-18
JP2003527389A (ja)	2003-09-16
HUP0301696A2 (hu)	2003-09-29
ES2223830T3 (es)	2005-03-01
DE60103859D1 (de)	2004-07-22
MXPA02009016A (es)	2004-10-15
CA2403149A1 (en)	2001-09-20
CZ20023058A3 (cs)	2004-01-14
AU2001254692A1 (en)	2001-09-24
AR030410A1 (es)	2003-08-20
RU2002127728A (ru)	2004-03-20
BG107101A (bg)	2003-07-31
ZA200207184B (en)	2003-12-08
IL151598A0 (en)	2003-04-10
BR0109252A (pt)	2002-12-24
NO20024393D0 (no)	2002-09-13
CN1429221A (zh)	2003-07-09
EE200200528A (et)	2004-04-15
PL358062A1 (pl)	2004-08-09
NZ521187A (en)	2004-03-26
US7354936B2 (en)	2008-04-08
ATE269316T1 (de)	2004-07-15
WO2001068633A1 (en)	2001-09-20
KR20030005221A (ko)	2003-01-17
HK1048117A1 (zh)	2003-03-21
SK12832002A3 (sk)	2003-11-04
DE60103859T2 (de)	2005-07-21
EP1263751A1 (en)	2002-12-11
PE20011333A1 (es)	2002-01-16

Legal Events

Date	Code	Title	Description
2004-11-08	FC2A	Withdrawal, rejection or dismissal of laid open patent application

Publication	Publication Date	Title
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