ES2213485B1 - Derivados de la 2-fenilpiran-4-ona. - Google Patents
Derivados de la 2-fenilpiran-4-ona.Info
- Publication number
- ES2213485B1 ES2213485B1 ES200300355A ES200300355A ES2213485B1 ES 2213485 B1 ES2213485 B1 ES 2213485B1 ES 200300355 A ES200300355 A ES 200300355A ES 200300355 A ES200300355 A ES 200300355A ES 2213485 B1 ES2213485 B1 ES 2213485B1
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- pyran
- methanesulfinylphenyl
- compound according
- group
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000004429 atom Chemical group 0.000 claims abstract description 18
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- -1 methylthio, amino Chemical group 0.000 claims description 62
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- OTLLZHXQRRNIOL-UHFFFAOYSA-N 3-(2,4-difluorophenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=C(F)C=C1F OTLLZHXQRRNIOL-UHFFFAOYSA-N 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 7
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 7
- RZDNFEBTJXOTQW-UHFFFAOYSA-N 3-(4-bromo-2-fluorophenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=C(Br)C=C1F RZDNFEBTJXOTQW-UHFFFAOYSA-N 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 6
- 206010037660 Pyrexia Diseases 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 229940127293 prostanoid Drugs 0.000 claims description 4
- 150000003814 prostanoids Chemical class 0.000 claims description 4
- 230000016160 smooth muscle contraction Effects 0.000 claims description 4
- 229940095064 tartrate Drugs 0.000 claims description 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 4
- NFRYFKOUAODBAF-UHFFFAOYSA-N 3-(4-chloro-2-fluorophenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=C(Cl)C=C1F NFRYFKOUAODBAF-UHFFFAOYSA-N 0.000 claims description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- UHXBJUHBIWWBPR-UHFFFAOYSA-N 3-(2,4-dibromophenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound BrC1=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=CC(=C1)Br UHXBJUHBIWWBPR-UHFFFAOYSA-N 0.000 claims description 2
- SWTYZBNPBSTVNO-UHFFFAOYSA-N 3-(2-bromophenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=CC=C1Br SWTYZBNPBSTVNO-UHFFFAOYSA-N 0.000 claims description 2
- JZYGNSNKBTXZLJ-UHFFFAOYSA-N 3-(2-chloro-4-methylphenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound ClC1=CC(C)=CC=C1OC1=C(C=2C=CC(=CC=2)S(C)=O)OC(C)=CC1=O JZYGNSNKBTXZLJ-UHFFFAOYSA-N 0.000 claims description 2
- ZAGZBIZSAODIBG-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound FC1=CC(C)=CC=C1OC1=C(C=2C=CC(=CC=2)S(C)=O)OC(C)=CC1=O ZAGZBIZSAODIBG-UHFFFAOYSA-N 0.000 claims description 2
- LRGCMGSFOVPALE-UHFFFAOYSA-N 3-(3-bromophenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound BrC=1C=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=CC=1 LRGCMGSFOVPALE-UHFFFAOYSA-N 0.000 claims description 2
- OVKKZRXNHVYQKY-UHFFFAOYSA-N 3-(4-bromo-2-chlorophenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound BrC1=CC(=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=C1)Cl OVKKZRXNHVYQKY-UHFFFAOYSA-N 0.000 claims description 2
- HHKBCGKZRATJJS-UHFFFAOYSA-N 3-(4-chloro-2-methylphenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound ClC1=CC(=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=C1)C HHKBCGKZRATJJS-UHFFFAOYSA-N 0.000 claims description 2
- XXDKQLSSQGPHCS-UHFFFAOYSA-N 3-(4-fluoro-2-methylphenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound FC1=CC(=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=C1)C XXDKQLSSQGPHCS-UHFFFAOYSA-N 0.000 claims description 2
- ZCCLJVFGLVAYFA-UHFFFAOYSA-N 6-methyl-3-(2-methylphenoxy)-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound CS(=O)C1=CC=C(C=C1)C=1OC(=CC(C=1OC1=C(C=CC=C1)C)=O)C ZCCLJVFGLVAYFA-UHFFFAOYSA-N 0.000 claims description 2
- ZLWHNMIJIHYPKX-UHFFFAOYSA-N 6-methyl-3-(3-methylphenoxy)-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound CS(=O)C1=CC=C(C=C1)C=1OC(=CC(C=1OC1=CC(=CC=C1)C)=O)C ZLWHNMIJIHYPKX-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 229940124599 anti-inflammatory drug Drugs 0.000 abstract description 2
- 125000000962 organic group Chemical group 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 20
- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 16
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 150000003254 radicals Chemical class 0.000 description 14
- 102000010906 Cyclooxygenase 1 Human genes 0.000 description 12
- 108010037464 Cyclooxygenase 1 Proteins 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000013543 active substance Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 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 4
- 239000007832 Na2SO4 Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 230000001404 mediated effect Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- YSSYIJBAPDTSAY-UHFFFAOYSA-N 2-bromo-1-(4-methylsulfanylphenyl)ethanone Chemical compound CSC1=CC=C(C(=O)CBr)C=C1 YSSYIJBAPDTSAY-UHFFFAOYSA-N 0.000 description 3
- 206010009944 Colon cancer Diseases 0.000 description 3
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- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 3
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 3
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- 208000006673 asthma Diseases 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- PVRATXCXJDHJJN-IMJSIDKUSA-N dimethyl (2s,3s)-2,3-dihydroxybutanedioate Chemical compound COC(=O)[C@@H](O)[C@H](O)C(=O)OC PVRATXCXJDHJJN-IMJSIDKUSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- 241000282414 Homo sapiens Species 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
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- 238000005119 centrifugation Methods 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
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- KHIWWQKSHDUIBK-UHFFFAOYSA-M periodate Chemical compound [O-]I(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-M 0.000 description 2
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- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
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- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
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- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- ZHYFMSAURZABER-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-1-(4-methylsulfanylphenyl)ethanone Chemical compound C1=CC(SC)=CC=C1C(=O)COC1=CC=C(F)C=C1F ZHYFMSAURZABER-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
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- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- HWULRPYVKPSPQR-UHFFFAOYSA-N 3-(2,4-difluorophenoxy)-6-methyl-2-(4-methylsulfanylphenyl)pyran-4-one Chemical compound C1=CC(SC)=CC=C1C1=C(OC=2C(=CC(F)=CC=2)F)C(=O)C=C(C)O1 HWULRPYVKPSPQR-UHFFFAOYSA-N 0.000 description 1
- OTLLZHXQRRNIOL-AREMUKBSSA-N 3-(2,4-difluorophenoxy)-6-methyl-2-[4-[(r)-methylsulfinyl]phenyl]pyran-4-one Chemical compound C=1C=C([S@@](C)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=C(F)C=C1F OTLLZHXQRRNIOL-AREMUKBSSA-N 0.000 description 1
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- 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
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- A—HUMAN NECESSITIES
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Landscapes
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- Catalysts (AREA)
- Pyrane Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200300355A ES2213485B1 (es) | 2003-02-13 | 2003-02-13 | Derivados de la 2-fenilpiran-4-ona. |
| EP04710358A EP1592680B9 (en) | 2003-02-13 | 2004-02-12 | 2-phenylpyran-4-one derivatives as selective cox-2 inhibitors |
| PCT/EP2004/001295 WO2004072058A1 (en) | 2003-02-13 | 2004-02-12 | 2-phenylpyran-4-one derivatives as selective cox-2 inhibitors |
| CNB2004800087372A CN100436438C (zh) | 2003-02-13 | 2004-02-12 | 2-苯基吡喃-4-酮衍生物作为环加氧酶-2的抑制剂 |
| DE602004013542T DE602004013542D1 (en) | 2003-02-13 | 2004-02-12 | 2-phenylpyran-4-on-derivate als selektive cox-2 inhibitoren |
| ES04710358T ES2303938T4 (es) | 2003-02-13 | 2004-02-12 | Derivados de 2-fenilpiran-2-ona como inhibidores selectivos de cox-2. |
| JP2006501815A JP2006517560A (ja) | 2003-02-13 | 2004-02-12 | 選択的ｃｏｘ−２阻害剤としての２−フェニルピラン−４−オン誘導体 |
| AT04710358T ATE394386T1 (de) | 2003-02-13 | 2004-02-12 | 2-phenylpyran-4-on-derivate als selektive cox-2 inhibitoren |
| US10/544,361 US7582676B2 (en) | 2003-02-13 | 2004-02-12 | 2-phenylpyran-4-one derivatives as selective COX-2 inhibitors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200300355A ES2213485B1 (es) | 2003-02-13 | 2003-02-13 | Derivados de la 2-fenilpiran-4-ona. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2213485A1 ES2213485A1 (es) | 2004-08-16 |
| ES2213485B1 true ES2213485B1 (es) | 2005-12-16 |
Family
ID=32865136
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200300355A Expired - Fee Related ES2213485B1 (es) | 2003-02-13 | 2003-02-13 | Derivados de la 2-fenilpiran-4-ona. |
| ES04710358T Expired - Lifetime ES2303938T4 (es) | 2003-02-13 | 2004-02-12 | Derivados de 2-fenilpiran-2-ona como inhibidores selectivos de cox-2. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04710358T Expired - Lifetime ES2303938T4 (es) | 2003-02-13 | 2004-02-12 | Derivados de 2-fenilpiran-2-ona como inhibidores selectivos de cox-2. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7582676B2 (https=) |
| EP (1) | EP1592680B9 (https=) |
| JP (1) | JP2006517560A (https=) |
| CN (1) | CN100436438C (https=) |
| AT (1) | ATE394386T1 (https=) |
| DE (1) | DE602004013542D1 (https=) |
| ES (2) | ES2213485B1 (https=) |
| WO (1) | WO2004072058A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2213485B1 (es) | 2003-02-13 | 2005-12-16 | Almirall Prodesfarma, S.A. | Derivados de la 2-fenilpiran-4-ona. |
| ES2214130B1 (es) * | 2003-02-13 | 2005-12-01 | Almirall Prodesfarma, S.A. | 2-3'-bipiridinas. |
| ES2214129B1 (es) * | 2003-02-13 | 2005-12-01 | Almirall Prodesfarma, S.A. | 3-fenilfuran-2-onas. |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000014083A1 (en) * | 1998-09-09 | 2000-03-16 | Inflazyme Pharmaceuticals Ltd. | SUBSTITUTED η-PHENYL-Δ-LACTONES AND ANALOGS THEREOF AND USES RELATED THERETO |
| ES2154561B1 (es) * | 1998-09-25 | 2001-12-01 | Almirall Prodesfarma Sa | Derivados de 2-fenilpiran-4-ona. |
| US6340694B1 (en) * | 1998-08-22 | 2002-01-22 | Pacific Corporation | Diarylbenzopyran derivatives as cyclooxygenase-2 inhibitors |
| US6492416B1 (en) * | 1999-04-14 | 2002-12-10 | Pacific Corporation | 4,5-diaryl-3(2H)-furanone derivatives as cyclooxygenase-2 inhibitors |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4304728A (en) * | 1979-04-05 | 1981-12-08 | Lilly Industries Limited | 6-Substituted pyranone compounds and their use as pharmaceuticals |
| US6486194B2 (en) | 1993-06-24 | 2002-11-26 | Merck Frosst Canada, Inc. | Use of inhibitors of cyclooxygenase in the treatment of neurodegenerative diseases |
| US5585504A (en) | 1994-09-16 | 1996-12-17 | Merck & Co., Inc. | Process of making cox-2 inhibitors having a lactone bridge |
| GB2294879A (en) | 1994-10-19 | 1996-05-15 | Merck & Co Inc | Cylcooxygenase-2 Inhibitors |
| US6231888B1 (en) * | 1996-01-18 | 2001-05-15 | Perio Products Ltd. | Local delivery of non steroidal anti inflammatory drugs (NSAIDS) to the colon as a treatment for colonic polyps |
| ES2125161B1 (es) | 1996-03-21 | 1999-11-16 | Grupo Farmaceutico Almirall S | Nuevos derivados de 2-(3h)-oxazolona. |
| CN1140267C (zh) | 1996-05-17 | 2004-03-03 | 麦克公司 | 治疗环加氧酶-2介导的疾病的每天一次的组合物 |
| IL127441A (en) | 1996-07-18 | 2003-02-12 | Merck Frosst Canada Inc | Substituted pyridines, pharmaceutical compositions comprising them and their use in the preparation of anti-inflammatory medicaments or as selective cyclooxygenase-2 inhibitors |
| US6307047B1 (en) * | 1997-08-22 | 2001-10-23 | Abbott Laboratories | Prostaglandin endoperoxide H synthase biosynthesis inhibitors |
| ES2256817T3 (es) * | 1997-09-05 | 2006-07-16 | Glaxo Group Limited | Composiciones farmaceuticas que comprenden derivados de 2,3-diaril-pirazolo(1,5-b)piridazina. |
| ES2131015B1 (es) | 1997-09-12 | 2000-03-01 | Almirall Prodesfarma Sa | Nuevos derivados de 2-(3h)-oxazolona, procedimientos para su preparacion y su empleo en composiciones farmaceuticas. |
| US5994379A (en) * | 1998-02-13 | 1999-11-30 | Merck Frosst Canada, Inc. | Bisaryl COX-2 inhibiting compounds, compositions and methods of use |
| TW587079B (en) * | 1998-09-25 | 2004-05-11 | Almirall Prodesfarma Ag | 2-phenylpyran-4-one derivatives |
| US6303972B1 (en) * | 1998-11-25 | 2001-10-16 | Micron Technology, Inc. | Device including a conductive layer protected against oxidation |
| AU5873000A (en) | 1999-06-24 | 2001-01-31 | Pharmacia Corporation | Combination of tumors necrocis factor (tnf) antagonists and cox-2 inhibitors forthe treatment of inflammation |
| DE60006057T2 (de) * | 1999-12-03 | 2004-05-27 | Pfizer Products Inc., Groton | Heteroarylphenylpyrazolverbindungen zur Verwendung als analgetisches/entzündungshemmendes Mittel |
| PE20011333A1 (es) * | 2000-03-16 | 2002-01-16 | Almirall Prodesfarma Ag | Derivados de 2-fenilpiran-4-ona como inhibidores de ciclooxigenasa 2 |
| CA2412651A1 (en) * | 2000-05-22 | 2001-11-29 | Dr. Reddy's Laboratories Limited | Novel compounds having antiinflammatory activity: process for their preparation and pharmaceutical compositions containing them |
| WO2001091856A2 (en) | 2000-06-01 | 2001-12-06 | Pharmacia Corporation | Use of cox2 inhibitors for treating skin injury from exposure to ultraviolet radiation |
| JP2004505060A (ja) | 2000-07-27 | 2004-02-19 | ファルマシア・コーポレーション | 炎症関連心臓血管障害を防止するかまたは治療するためのアルドステロンアンタゴニストおよびシクロオキシゲナーゼ−２阻害剤併用療法 |
| WO2002055502A1 (en) | 2001-01-02 | 2002-07-18 | Fujisawa Pharmaceutical Co., Ltd. | Pyridine derivatives useful as cyclooxygenase inhibitor |
| WO2003006451A1 (en) | 2001-07-10 | 2003-01-23 | Almirall Prodesfarma S.A. | 4-phenylpyran-2-one derivatives |
| EP1492773B1 (en) | 2002-04-05 | 2009-02-04 | Cadila Healthcare Ltd. | 4-(heterocyclyl)-benzenesulfoximine compounds for the treatment of inflammation |
| ES2214129B1 (es) | 2003-02-13 | 2005-12-01 | Almirall Prodesfarma, S.A. | 3-fenilfuran-2-onas. |
| ES2214130B1 (es) | 2003-02-13 | 2005-12-01 | Almirall Prodesfarma, S.A. | 2-3'-bipiridinas. |
| ES2213485B1 (es) | 2003-02-13 | 2005-12-16 | Almirall Prodesfarma, S.A. | Derivados de la 2-fenilpiran-4-ona. |
-
2003
- 2003-02-13 ES ES200300355A patent/ES2213485B1/es not_active Expired - Fee Related
-
2004
- 2004-02-12 WO PCT/EP2004/001295 patent/WO2004072058A1/en not_active Ceased
- 2004-02-12 JP JP2006501815A patent/JP2006517560A/ja active Pending
- 2004-02-12 ES ES04710358T patent/ES2303938T4/es not_active Expired - Lifetime
- 2004-02-12 CN CNB2004800087372A patent/CN100436438C/zh not_active Expired - Fee Related
- 2004-02-12 AT AT04710358T patent/ATE394386T1/de not_active IP Right Cessation
- 2004-02-12 DE DE602004013542T patent/DE602004013542D1/de not_active Expired - Fee Related
- 2004-02-12 US US10/544,361 patent/US7582676B2/en not_active Expired - Fee Related
- 2004-02-12 EP EP04710358A patent/EP1592680B9/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6340694B1 (en) * | 1998-08-22 | 2002-01-22 | Pacific Corporation | Diarylbenzopyran derivatives as cyclooxygenase-2 inhibitors |
| WO2000014083A1 (en) * | 1998-09-09 | 2000-03-16 | Inflazyme Pharmaceuticals Ltd. | SUBSTITUTED η-PHENYL-Δ-LACTONES AND ANALOGS THEREOF AND USES RELATED THERETO |
| ES2154561B1 (es) * | 1998-09-25 | 2001-12-01 | Almirall Prodesfarma Sa | Derivados de 2-fenilpiran-4-ona. |
| US6492416B1 (en) * | 1999-04-14 | 2002-12-10 | Pacific Corporation | 4,5-diaryl-3(2H)-furanone derivatives as cyclooxygenase-2 inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1592680B9 (en) | 2009-03-25 |
| ES2213485A1 (es) | 2004-08-16 |
| DE602004013542D1 (en) | 2008-06-19 |
| CN1768049A (zh) | 2006-05-03 |
| US7582676B2 (en) | 2009-09-01 |
| CN100436438C (zh) | 2008-11-26 |
| ES2303938T3 (es) | 2008-09-01 |
| WO2004072058A1 (en) | 2004-08-26 |
| EP1592680A1 (en) | 2005-11-09 |
| EP1592680B1 (en) | 2008-05-07 |
| ATE394386T1 (de) | 2008-05-15 |
| ES2303938T4 (es) | 2009-06-05 |
| US20060142380A1 (en) | 2006-06-29 |
| JP2006517560A (ja) | 2006-07-27 |
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