NO327987B1 - 2-Fenylpyran-4-on derivater - Google Patents
2-Fenylpyran-4-on derivater Download PDFInfo
- Publication number
- NO327987B1 NO327987B1 NO20011512A NO20011512A NO327987B1 NO 327987 B1 NO327987 B1 NO 327987B1 NO 20011512 A NO20011512 A NO 20011512A NO 20011512 A NO20011512 A NO 20011512A NO 327987 B1 NO327987 B1 NO 327987B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- methanesulfonylphenyl
- methylpyran
- alkyl
- formula
- Prior art date
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- 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 20
- 150000001875 compounds Chemical class 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- -1 methylthio, amino Chemical group 0.000 claims description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 7
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- GPURLOFCRUSYCW-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-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=1C1=CC=C(F)C=C1F GPURLOFCRUSYCW-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 208000002193 Pain Diseases 0.000 claims description 4
- 206010037660 Pyrexia Diseases 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 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
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
- UOUHUNXQGPPJIS-UHFFFAOYSA-N 3-(2,5-difluorophenoxy)-6-methyl-2-(2-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=CC=C(S(C)(=O)=O)C=1C=1OC(C)=CC(=O)C=1OC1=CC(F)=CC=C1F UOUHUNXQGPPJIS-UHFFFAOYSA-N 0.000 claims description 3
- ZGYXDCGAOVKCQH-UHFFFAOYSA-N 3-(2-chlorophenoxy)-6-methyl-2-(2-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=CC=C(S(C)(=O)=O)C=1C=1OC(C)=CC(=O)C=1OC1=CC=CC=C1Cl ZGYXDCGAOVKCQH-UHFFFAOYSA-N 0.000 claims description 3
- QXJHSRWDYCYSRO-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-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=1C1=CC=C(Cl)C(Cl)=C1 QXJHSRWDYCYSRO-UHFFFAOYSA-N 0.000 claims description 3
- SVAIEEBVIUQQQM-UHFFFAOYSA-N 3-(3-chloro-4-methylphenyl)-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=1C1=CC=C(C)C(Cl)=C1 SVAIEEBVIUQQQM-UHFFFAOYSA-N 0.000 claims description 3
- WFHGNFDDTVLOEU-UHFFFAOYSA-N 3-(4-bromophenyl)-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=1C1=CC=C(Br)C=C1 WFHGNFDDTVLOEU-UHFFFAOYSA-N 0.000 claims description 3
- XRHLSOYDPVRXAE-UHFFFAOYSA-N 6-methyl-2-(4-methylsulfonylphenyl)-3-phenoxypyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=CC=C1 XRHLSOYDPVRXAE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 238000006264 debenzylation reaction Methods 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- 229940127293 prostanoid Drugs 0.000 claims description 3
- 150000003814 prostanoids Chemical class 0.000 claims description 3
- 230000016160 smooth muscle contraction Effects 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 41
- 239000002904 solvent Substances 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000011734 sodium Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 15
- 239000003480 eluent Substances 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 14
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 102000010906 Cyclooxygenase 1 Human genes 0.000 description 10
- 108010037464 Cyclooxygenase 1 Proteins 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 6
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- MWFHCAZWUNYBDP-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(4-methylsulfonylphenyl)-4-oxopyran-2-carbaldehyde Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)C=C(C=O)O1 MWFHCAZWUNYBDP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 4
- 230000002917 arthritic effect Effects 0.000 description 4
- 208000006673 asthma Diseases 0.000 description 4
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000001404 mediated effect Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WOBUKGPQDSRSPN-UHFFFAOYSA-N 3-(2,4-difluorophenoxy)-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=C1F WOBUKGPQDSRSPN-UHFFFAOYSA-N 0.000 description 3
- JFVGUQHTGVPGKP-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-(difluoromethyl)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)C=C(C(F)F)O1 JFVGUQHTGVPGKP-UHFFFAOYSA-N 0.000 description 3
- WHZQULKJHFNVJF-UHFFFAOYSA-N 3-(4-chlorophenyl)-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=1C1=CC=C(Cl)C=C1 WHZQULKJHFNVJF-UHFFFAOYSA-N 0.000 description 3
- RVXUQYKMAOJXAP-UHFFFAOYSA-N 3-(4-chlorophenyl)-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=1C1=CC=C(Cl)C=C1 RVXUQYKMAOJXAP-UHFFFAOYSA-N 0.000 description 3
- RQVVYXPUTAFVJV-UHFFFAOYSA-N 3-(4-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(F)C=C1 RQVVYXPUTAFVJV-UHFFFAOYSA-N 0.000 description 3
- WJMZUULFKISOCN-UHFFFAOYSA-N 3-(4-fluorophenyl)-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=1C1=CC=C(F)C=C1 WJMZUULFKISOCN-UHFFFAOYSA-N 0.000 description 3
- AYAKDXHPTOEADO-UHFFFAOYSA-N 4-(dibenzylsulfamoyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 AYAKDXHPTOEADO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 201000004624 Dermatitis Diseases 0.000 description 3
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 3
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
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- 208000027418 Wounds and injury Diseases 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
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- 229910052801 chlorine Inorganic materials 0.000 description 3
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- 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 2
- 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 2
- PHUUAEKXLFCCKB-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-1-(4-methylsulfonylphenyl)ethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)COC1=CC=C(F)C=C1F PHUUAEKXLFCCKB-UHFFFAOYSA-N 0.000 description 2
- YRCBOEDYXNRZGI-UHFFFAOYSA-N 3-(2-fluorophenoxy)-6-methyl-2-(2-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=CC=C(S(C)(=O)=O)C=1C=1OC(C)=CC(=O)C=1OC1=CC=CC=C1F YRCBOEDYXNRZGI-UHFFFAOYSA-N 0.000 description 2
- ZGQDYDMRFRTLDT-UHFFFAOYSA-N 3-(2-fluorophenyl)-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=1C1=CC=CC=C1F ZGQDYDMRFRTLDT-UHFFFAOYSA-N 0.000 description 2
- IFAPESKQRSIUFT-UHFFFAOYSA-N 3-(4-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=C(Br)C=C1 IFAPESKQRSIUFT-UHFFFAOYSA-N 0.000 description 2
- XWKIRCKDFSBMOU-UHFFFAOYSA-N 3-(4-chlorophenoxy)-6-methyl-2-(2-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=CC=C(S(C)(=O)=O)C=1C=1OC(C)=CC(=O)C=1OC1=CC=C(Cl)C=C1 XWKIRCKDFSBMOU-UHFFFAOYSA-N 0.000 description 2
- YZXBCOGZVJACRE-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-(hydroxymethyl)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)C=C(CO)O1 YZXBCOGZVJACRE-UHFFFAOYSA-N 0.000 description 2
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- 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
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- 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
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9802011A ES2154561B1 (es) | 1998-09-25 | 1998-09-25 | Derivados de 2-fenilpiran-4-ona. |
| ES009900619A ES2168895A1 (es) | 1999-03-26 | 1999-03-26 | Derivados de 2-fenilpiran-4-ona. |
| PCT/EP1999/006873 WO2000018753A1 (en) | 1998-09-25 | 1999-09-16 | 2-phenylpyran-4-one derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20011512D0 NO20011512D0 (no) | 2001-03-23 |
| NO20011512L NO20011512L (no) | 2001-05-25 |
| NO327987B1 true NO327987B1 (no) | 2009-11-02 |
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|---|---|---|---|
| NO20011512A NO327987B1 (no) | 1998-09-25 | 2001-03-23 | 2-Fenylpyran-4-on derivater |
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| EP (1) | EP1115716B1 (es) |
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| BG (1) | BG65308B1 (es) |
| BR (1) | BR9913939A (es) |
| CA (1) | CA2345069C (es) |
| CO (1) | CO5140127A1 (es) |
| CZ (1) | CZ300357B6 (es) |
| DE (1) | DE69904738T2 (es) |
| DK (1) | DK1115716T3 (es) |
| EE (1) | EE04812B1 (es) |
| EG (1) | EG23802A (es) |
| ES (1) | ES2190252T3 (es) |
| HK (1) | HK1034961A1 (es) |
| HU (1) | HUP0104620A3 (es) |
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| MX (1) | MXPA01003069A (es) |
| MY (1) | MY121793A (es) |
| NO (1) | NO327987B1 (es) |
| NZ (1) | NZ510625A (es) |
| PE (1) | PE20001067A1 (es) |
| PL (1) | PL346895A1 (es) |
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| SK (1) | SK286471B6 (es) |
| TR (1) | TR200100852T2 (es) |
| TW (1) | TW587079B (es) |
| WO (1) | WO2000018753A1 (es) |
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| PE20011333A1 (es) | 2000-03-16 | 2002-01-16 | Almirall Prodesfarma Ag | Derivados de 2-fenilpiran-4-ona como inhibidores de ciclooxigenasa 2 |
| US20040147581A1 (en) * | 2002-11-18 | 2004-07-29 | Pharmacia Corporation | Method of using a Cox-2 inhibitor and a 5-HT1A receptor modulator as a combination therapy |
| ES2214129B1 (es) * | 2003-02-13 | 2005-12-01 | Almirall Prodesfarma, S.A. | 3-fenilfuran-2-onas. |
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| US304728A (en) * | 1884-09-09 | Maubice hellwig | ||
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| 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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