ZA200207184B - 2-phenylpyran-4-one derivatives. - Google Patents
2-phenylpyran-4-one derivatives. Download PDFInfo
- Publication number
- ZA200207184B ZA200207184B ZA200207184A ZA200207184A ZA200207184B ZA 200207184 B ZA200207184 B ZA 200207184B ZA 200207184 A ZA200207184 A ZA 200207184A ZA 200207184 A ZA200207184 A ZA 200207184A ZA 200207184 B ZA200207184 B ZA 200207184B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- alkyl
- formula
- methanesulfonylphenyl
- methyl
- Prior art date
Links
- UFECLJRYNAOWOI-UHFFFAOYSA-N 2-phenylpyran-4-one Chemical class O=C1C=COC(C=2C=CC=CC=2)=C1 UFECLJRYNAOWOI-UHFFFAOYSA-N 0.000 title description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 117
- 150000001875 compounds Chemical class 0.000 claims description 82
- -1 methylthio, amino Chemical group 0.000 claims description 67
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 claims description 14
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004434 sulfur atom Chemical group 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 7
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 6
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 206010011416 Croup infectious Diseases 0.000 claims description 4
- 201000010549 croup Diseases 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 208000002193 Pain Diseases 0.000 claims description 3
- 206010037660 Pyrexia Diseases 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000004054 inflammatory process Effects 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
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 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 2
- 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 2
- 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 2
- 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 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 229940099990 ogen Drugs 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 230000016160 smooth muscle contraction Effects 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 241001302806 Helogenes Species 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 238000006264 debenzylation reaction Methods 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 229940127293 prostanoid Drugs 0.000 claims 1
- 150000003814 prostanoids Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 3
- 102000010906 Cyclooxygenase 1 Human genes 0.000 description 3
- 108010037464 Cyclooxygenase 1 Proteins 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical class [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 2
- 150000003180 prostaglandins Chemical class 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- KNZCMOTWSWAOQG-UHFFFAOYSA-N 3-(4-bromo-2-fluorophenoxy)-6-methyl-2-(4-methylsulfonylphenyl)-2h-pyran Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C1OC(C)=CC=C1OC1=CC=C(Br)C=C1F KNZCMOTWSWAOQG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- PXNGUZXOJZTTRK-UHFFFAOYSA-N F.FS(F)(F)F Chemical compound F.FS(F)(F)F PXNGUZXOJZTTRK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000091 aluminium hydride Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- IAQWMWUKBQPOIY-UHFFFAOYSA-N chromium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Cr+4] IAQWMWUKBQPOIY-UHFFFAOYSA-N 0.000 description 1
- AYTAKQFHWFYBMA-UHFFFAOYSA-N chromium(IV) oxide Inorganic materials O=[Cr]=O AYTAKQFHWFYBMA-UHFFFAOYSA-N 0.000 description 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- USSBDBZGEDUBHE-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate Chemical compound [Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O USSBDBZGEDUBHE-UHFFFAOYSA-L 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012740 non-selective inhibitor Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 230000008327 renal blood flow Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200000637 | 2000-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200207184B true ZA200207184B (en) | 2003-12-08 |
Family
ID=8492732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200207184A ZA200207184B (en) | 2000-03-16 | 2002-09-06 | 2-phenylpyran-4-one derivatives. |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7354936B2 (xx) |
| EP (1) | EP1263751B1 (xx) |
| JP (1) | JP2003527389A (xx) |
| KR (1) | KR20030005221A (xx) |
| CN (1) | CN1429221A (xx) |
| AR (1) | AR030410A1 (xx) |
| AT (1) | ATE269316T1 (xx) |
| AU (1) | AU2001254692A1 (xx) |
| BG (1) | BG107101A (xx) |
| BR (1) | BR0109252A (xx) |
| CA (1) | CA2403149A1 (xx) |
| CZ (1) | CZ20023058A3 (xx) |
| DE (1) | DE60103859T2 (xx) |
| EE (1) | EE200200528A (xx) |
| ES (1) | ES2223830T3 (xx) |
| HK (1) | HK1048117A1 (xx) |
| HU (1) | HUP0301696A2 (xx) |
| IL (1) | IL151598A0 (xx) |
| MX (1) | MXPA02009016A (xx) |
| NO (1) | NO20024393L (xx) |
| NZ (1) | NZ521187A (xx) |
| PE (1) | PE20011333A1 (xx) |
| PL (1) | PL358062A1 (xx) |
| RU (1) | RU2002127728A (xx) |
| SK (1) | SK12832002A3 (xx) |
| WO (1) | WO2001068633A1 (xx) |
| ZA (1) | ZA200207184B (xx) |
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 |
| EP0729466A1 (en) * | 1993-11-19 | 1996-09-04 | 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 |
| CN1186492A (zh) | 1995-04-04 | 1998-07-01 | 葛兰素集团有限公司 | 咪唑并[1,2－α]吡啶衍生物 |
| PT1043317E (pt) * | 1997-11-19 | 2009-05-11 | Kowa Co | Novos derivados de piridazina e fármacos que os contêm como ingrediente activo |
| 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 IL IL15159801A patent/IL151598A0/xx unknown
- 2001-03-16 JP JP2001567725A patent/JP2003527389A/ja not_active Withdrawn
- 2001-03-16 AU AU2001254692A patent/AU2001254692A1/en not_active Abandoned
- 2001-03-16 EE EEP200200528A patent/EE200200528A/xx unknown
- 2001-03-16 CN CN01809447A patent/CN1429221A/zh active Pending
- 2001-03-16 NZ NZ521187A patent/NZ521187A/en unknown
- 2001-03-16 HU HU0301696A patent/HUP0301696A2/hu unknown
- 2001-03-16 DE DE60103859T patent/DE60103859T2/de not_active Expired - Lifetime
- 2001-03-16 KR KR1020027011875A patent/KR20030005221A/ko not_active Application Discontinuation
- 2001-03-16 RU RU2002127728/04A patent/RU2002127728A/ru not_active Application Discontinuation
- 2001-03-16 CZ CZ20023058A patent/CZ20023058A3/cs unknown
- 2001-03-16 EP EP01927742A patent/EP1263751B1/en not_active Expired - Lifetime
- 2001-03-16 SK SK1283-2002A patent/SK12832002A3/sk unknown
- 2001-03-16 WO PCT/EP2001/003042 patent/WO2001068633A1/en active IP Right Grant
- 2001-03-16 AT AT01927742T patent/ATE269316T1/de not_active IP Right Cessation
- 2001-03-16 PL PL01358062A patent/PL358062A1/xx not_active Application Discontinuation
- 2001-03-16 CA CA002403149A patent/CA2403149A1/en not_active Abandoned
- 2001-03-16 MX MXPA02009016A patent/MXPA02009016A/es unknown
- 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
-
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
-
2003
- 2003-01-11 HK HK03100285.1A patent/HK1048117A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7354936B2 (en) | 2008-04-08 |
| BR0109252A (pt) | 2002-12-24 |
| SK12832002A3 (sk) | 2003-11-04 |
| EP1263751B1 (en) | 2004-06-16 |
| ATE269316T1 (de) | 2004-07-15 |
| CZ20023058A3 (cs) | 2004-01-14 |
| WO2001068633A1 (en) | 2001-09-20 |
| KR20030005221A (ko) | 2003-01-17 |
| PL358062A1 (en) | 2004-08-09 |
| DE60103859T2 (de) | 2005-07-21 |
| HK1048117A1 (zh) | 2003-03-21 |
| JP2003527389A (ja) | 2003-09-16 |
| IL151598A0 (en) | 2003-04-10 |
| US20030232880A1 (en) | 2003-12-18 |
| RU2002127728A (ru) | 2004-03-20 |
| NO20024393D0 (no) | 2002-09-13 |
| AU2001254692A1 (en) | 2001-09-24 |
| NZ521187A (en) | 2004-03-26 |
| NO20024393L (no) | 2002-11-13 |
| EE200200528A (et) | 2004-04-15 |
| EP1263751A1 (en) | 2002-12-11 |
| BG107101A (bg) | 2003-07-31 |
| CA2403149A1 (en) | 2001-09-20 |
| AR030410A1 (es) | 2003-08-20 |
| CN1429221A (zh) | 2003-07-09 |
| HUP0301696A2 (hu) | 2003-09-29 |
| PE20011333A1 (es) | 2002-01-16 |
| DE60103859D1 (de) | 2004-07-22 |
| MXPA02009016A (es) | 2004-10-15 |
| ES2223830T3 (es) | 2005-03-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0828724B1 (en) | Diaryl-5-oxygenated-2-(5h)-furanones as cox-2 inhibitors | |
| JPH11500146A (ja) | Ｃｏｘ−２インヒビターとしての（メチルスルホニル）フェニル−２−（５ｈ）−フラノン類 | |
| JP2001517654A (ja) | Ｃｏｘ−２のインヒビターとして有用なジアリールピリジンの製造方法 | |
| CA2301742C (en) | 2,3,5-trisubstituted pyridines as inhibitors of cyclooxygenase-2 | |
| CZ79297A3 (en) | Process for preparing phenylheterocyclic compounds | |
| JPH11500748A (ja) | Ｃｏｘ−２阻害剤のプロドラッグとしての３，４−ジアリール−２−ヒドロキシ−２，５−ジヒドロフラン | |
| HUT52494A (en) | Process for the preparation of cyclic ether derivatives | |
| US6465509B2 (en) | Pyrones as inhibitors of cyclooxygenase-2 | |
| ZA200207184B (en) | 2-phenylpyran-4-one derivatives. | |
| JP4717211B2 (ja) | ２−フェニルピラン−４−オン誘導体 | |
| AU2001268881A1 (en) | Pyrones as inhibitors of cyclooxygenase-2 | |
| JPS5851953B2 (ja) | ピラゾ−ルユウドウタイノセイゾウホウホウオヨビドウブツヨウイヤク | |
| JP2001514668A (ja) | Ｃｏｘ−２阻害薬としての酸素連結部を有する（メチルスルホニル）フェニル−２−（５ｈ）−フラノン類 | |
| AU741790B2 (en) | Diaryl-5-alkyl-5-methyl-2(5H)-furanones as selective cyclooxygenase-2 inhibitors | |
| TW200528444A (en) | Novel triarylimidazole derivatives | |
| CA1105024A (en) | Anti-inflammatory-4,5-dicyclic-2-(substituted thio) imidazoles and their corresponding sulfoxides and sulfones | |
| US6004960A (en) | Pyridazinones as inhibitors of cyclooxygenase-2 | |
| JP2006517561A (ja) | Ｃｏｘ−２阻害剤としての３−フェニルフラン−２−オン誘導体 | |
| ZA200102393B (en) | 2-phenylpyran-4-one derivatives. | |
| EP1048649A1 (en) | 5-arylpyrrole derivatives |