MXPA03001178A - Derivados de quinolina como agentes anti-inflamatorios. - Google Patents
Derivados de quinolina como agentes anti-inflamatorios.Info
- Publication number
- MXPA03001178A MXPA03001178A MXPA03001178A MXPA03001178A MXPA03001178A MX PA03001178 A MXPA03001178 A MX PA03001178A MX PA03001178 A MXPA03001178 A MX PA03001178A MX PA03001178 A MXPA03001178 A MX PA03001178A MX PA03001178 A MXPA03001178 A MX PA03001178A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- methoxy
- compound
- phenyl
- methanesulfonyl
- Prior art date
Links
- 239000002260 anti-inflammatory agent Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 163
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
- 201000010099 disease Diseases 0.000 claims abstract description 21
- 239000003112 inhibitor Substances 0.000 claims abstract description 13
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 5
- -1 alkylsulfañyl Chemical group 0.000 claims description 150
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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 59
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 19
- 230000003647 oxidation Effects 0.000 claims description 16
- 238000007254 oxidation reaction Methods 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 229940002612 prodrug Drugs 0.000 claims description 7
- 239000000651 prodrug Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 206010003246 arthritis Diseases 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 208000027418 Wounds and injury Diseases 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- 230000006378 damage Effects 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 208000014674 injury Diseases 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 206010006811 Bursitis Diseases 0.000 claims description 4
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 4
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 4
- 201000005569 Gout Diseases 0.000 claims description 4
- 206010019233 Headaches Diseases 0.000 claims description 4
- 201000002481 Myositis Diseases 0.000 claims description 4
- 208000010040 Sprains and Strains Diseases 0.000 claims description 4
- 208000000491 Tendinopathy Diseases 0.000 claims description 4
- 206010043255 Tendonitis Diseases 0.000 claims description 4
- 231100000869 headache Toxicity 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 201000004595 synovitis Diseases 0.000 claims description 4
- 201000004415 tendinitis Diseases 0.000 claims description 4
- 208000004371 toothache Diseases 0.000 claims description 4
- 208000008822 Ankylosis Diseases 0.000 claims description 3
- 208000008035 Back Pain Diseases 0.000 claims description 3
- 206010023198 Joint ankylosis Diseases 0.000 claims description 3
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 3
- 201000002661 Spondylitis Diseases 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 3
- 125000004476 heterocycloamino group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 206010036600 Premature labour Diseases 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005171 cycloalkylsulfanyl group Chemical group 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 208000026440 premature labor Diseases 0.000 claims description 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 abstract description 5
- 208000023275 Autoimmune disease Diseases 0.000 abstract description 4
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 229910001868 water Inorganic materials 0.000 description 30
- 235000019439 ethyl acetate Nutrition 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 18
- 150000002431 hydrogen Chemical group 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 239000012425 OXONE® Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 230000003110 anti-inflammatory effect Effects 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 150000003180 prostaglandins Chemical class 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- 125000003884 phenylalkyl group Chemical group 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 7
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 238000003556 assay Methods 0.000 description 7
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 208000002193 Pain Diseases 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 235000010418 carrageenan Nutrition 0.000 description 6
- 229920001525 carrageenan Polymers 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- AREWYRAETFMKAH-UHFFFAOYSA-N 1-sulfidoquinolin-1-ium Chemical compound C1=CC=C2[N+]([S-])=CC=CC2=C1 AREWYRAETFMKAH-UHFFFAOYSA-N 0.000 description 5
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 5
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000000460 chlorine Chemical group 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- XEMZUOZUYGPCSL-UHFFFAOYSA-N 6-methoxy-2-methylsulfonylquinoline Chemical compound N1=C(S(C)(=O)=O)C=CC2=CC(OC)=CC=C21 XEMZUOZUYGPCSL-UHFFFAOYSA-N 0.000 description 4
- 208000024827 Alzheimer disease Diseases 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000008282 halocarbons Chemical class 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 238000005192 partition Methods 0.000 description 4
- 239000003880 polar aprotic solvent Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- PEZNEXFPRSOYPL-UHFFFAOYSA-N (bis(trifluoroacetoxy)iodo)benzene Chemical compound FC(F)(F)C(=O)OI(OC(=O)C(F)(F)F)C1=CC=CC=C1 PEZNEXFPRSOYPL-UHFFFAOYSA-N 0.000 description 3
- ZFEJTYQUWRVCFW-UHFFFAOYSA-N 2-chloro-6-methoxyquinoline Chemical compound N1=C(Cl)C=CC2=CC(OC)=CC=C21 ZFEJTYQUWRVCFW-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- OIYRFJFOTTZCJL-UHFFFAOYSA-N 5-(4-fluorophenyl)sulfanyl-2-methylsulfonylquinolin-6-ol Chemical compound OC=1C=CC2=NC(S(=O)(=O)C)=CC=C2C=1SC1=CC=C(F)C=C1 OIYRFJFOTTZCJL-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- OQHHSGRZCKGLCY-UHFFFAOYSA-N 8-nitroquinoline Chemical compound C1=CN=C2C([N+](=O)[O-])=CC=CC2=C1 OQHHSGRZCKGLCY-UHFFFAOYSA-N 0.000 description 3
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- 102000004190 Enzymes Human genes 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
- 210000000416 exudates and transudate Anatomy 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
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- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
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- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 3
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- 229940068968 polysorbate 80 Drugs 0.000 description 3
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- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 3
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- 239000003826 tablet Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- UZOLLAZNQYGQJJ-UHFFFAOYSA-N (6-methoxy-2-methylsulfonylquinolin-5-yl)-(4-methoxyphenyl)methanol Chemical compound C1=CC(OC)=CC=C1C(O)C1=C(OC)C=CC2=NC(S(C)(=O)=O)=CC=C12 UZOLLAZNQYGQJJ-UHFFFAOYSA-N 0.000 description 2
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 2
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- 239000002105 nanoparticle Substances 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- LVSJDHGRKAEGLX-UHFFFAOYSA-N oxolane;2,2,2-trifluoroacetic acid Chemical compound C1CCOC1.OC(=O)C(F)(F)F LVSJDHGRKAEGLX-UHFFFAOYSA-N 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- 125000004351 phenylcyclohexyl group Chemical group C1(=CC=CC=C1)C1(CCCCC1)* 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 201000003068 rheumatic fever Diseases 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 101150073238 sor1 gene Proteins 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- 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
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pregnancy & Childbirth (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22419600P | 2000-08-09 | 2000-08-09 | |
| PCT/EP2001/008880 WO2002012192A1 (en) | 2000-08-09 | 2001-08-01 | Quinolene derivatives as anti-inflammation agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA03001178A true MXPA03001178A (es) | 2003-06-30 |
Family
ID=22839655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA03001178A MXPA03001178A (es) | 2000-08-09 | 2001-08-01 | Derivados de quinolina como agentes anti-inflamatorios. |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7049325B2 (enExample) |
| EP (1) | EP1313707B1 (enExample) |
| JP (1) | JP3930428B2 (enExample) |
| KR (1) | KR20030027016A (enExample) |
| CN (1) | CN1199950C (enExample) |
| AR (1) | AR033554A1 (enExample) |
| AT (1) | ATE367379T1 (enExample) |
| AU (1) | AU2001277560A1 (enExample) |
| BR (1) | BR0113175A (enExample) |
| CA (1) | CA2418832A1 (enExample) |
| DE (1) | DE60129445T2 (enExample) |
| ES (1) | ES2290161T3 (enExample) |
| MX (1) | MXPA03001178A (enExample) |
| WO (1) | WO2002012192A1 (enExample) |
| ZA (1) | ZA200300847B (enExample) |
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|---|---|---|---|---|
| TW591089B (en) * | 2001-08-09 | 2004-06-11 | Cheil Ind Inc | Slurry composition for use in chemical mechanical polishing of metal wiring |
| GB0220953D0 (en) * | 2002-09-10 | 2002-10-23 | Novartis Ag | Organic compounds |
| US7132432B2 (en) * | 2003-06-05 | 2006-11-07 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of tumor necrosis factor-alpha converting enzyme (TACE) |
| CN103172697A (zh) * | 2005-03-08 | 2013-06-26 | 贝林格尔.英格海姆国际有限公司 | 制备大环化合物的方法 |
| AU2009293493B2 (en) * | 2008-09-17 | 2014-09-18 | Boehringer Ingelheim International Gmbh | Combination of HCV NS3 protease inhibitor with interferon and ribavirin |
| KR20120106942A (ko) | 2009-10-30 | 2012-09-27 | 베링거 인겔하임 인터내셔날 게엠베하 | Ｂｉ２０１３３５, 인터페론 알파 및 리바비린을 포함하는 ｈｃｖ 병용 치료요법을 위한 투여 용법 |
| US9383448B2 (en) | 2012-07-05 | 2016-07-05 | Deca System Co., Ltd. | Golf GPS device with automatic hole recognition and playing hole selection |
| CN117924243B (zh) * | 2024-01-16 | 2025-09-12 | 沈阳药科大学 | 一种喹啉衍生物及其药用组合物和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9018134D0 (en) | 1989-09-29 | 1990-10-03 | Ici Plc | Heterocyclic derivatives |
| MX9200299A (es) | 1991-02-07 | 1992-12-01 | Roussel Uclaf | Nuevos derivados biciclicos nitrogenados, su procedimiento de preparacion los nuevos compuestos intermedios obtenidos su aplicacion como medicamentos y las composiciones farmaceuticas que los contienen. |
| ATE156120T1 (de) | 1991-02-07 | 1997-08-15 | Roussel Uclaf | Bizyklische stickstoffverbindungen, ihre herstellung, erhaltene zwischenprodukte, ihre verwendung als arzneimittel und diese enthaltende pharmazeutische zusammensetzungen |
| GB9311790D0 (en) * | 1993-06-08 | 1993-07-28 | Minnesota Mining & Mfg | Photothermographic materials |
| DK122693D0 (da) | 1993-10-29 | 1993-10-29 | Hempels Skibsfarve Fab J C | Marin struktur |
| EP0830133A1 (en) * | 1995-04-28 | 1998-03-25 | Takeda Chemical Industries, Ltd. | Therapeutic composition for arthritis |
| DE19638486A1 (de) * | 1996-09-20 | 1998-03-26 | Basf Ag | Hetaroylderivate |
| DE19638484A1 (de) * | 1996-09-20 | 1998-03-26 | Basf Ag | Hetaroylderivate |
| US6069151A (en) | 1996-11-06 | 2000-05-30 | Darwin Discovery, Ltd. | Quinolines and their therapeutic use |
| PA8444901A1 (es) * | 1997-01-28 | 2000-05-24 | Hoffmann La Roche | Derivados de 5-aroilnaftaleno como agentes anti-inflamatorios |
| US6034256A (en) * | 1997-04-21 | 2000-03-07 | G.D. Searle & Co. | Substituted benzopyran derivatives for the treatment of inflammation |
| US6077850A (en) * | 1997-04-21 | 2000-06-20 | G.D. Searle & Co. | Substituted benzopyran analogs for the treatment of inflammation |
| US6479438B2 (en) * | 2001-01-04 | 2002-11-12 | Isp Investments Inc. | Gel inhibited liquid carrier for a biocide containing a carbodiimide and an emulsifier mixture |
-
2001
- 2001-08-01 JP JP2002518170A patent/JP3930428B2/ja not_active Expired - Fee Related
- 2001-08-01 CA CA002418832A patent/CA2418832A1/en not_active Abandoned
- 2001-08-01 BR BR0113175-3A patent/BR0113175A/pt not_active IP Right Cessation
- 2001-08-01 DE DE60129445T patent/DE60129445T2/de not_active Expired - Fee Related
- 2001-08-01 CN CNB018163513A patent/CN1199950C/zh not_active Expired - Fee Related
- 2001-08-01 AU AU2001277560A patent/AU2001277560A1/en not_active Abandoned
- 2001-08-01 KR KR10-2003-7001942A patent/KR20030027016A/ko not_active Ceased
- 2001-08-01 ES ES01955382T patent/ES2290161T3/es not_active Expired - Lifetime
- 2001-08-01 EP EP01955382A patent/EP1313707B1/en not_active Expired - Lifetime
- 2001-08-01 WO PCT/EP2001/008880 patent/WO2002012192A1/en not_active Ceased
- 2001-08-01 MX MXPA03001178A patent/MXPA03001178A/es unknown
- 2001-08-01 AT AT01955382T patent/ATE367379T1/de not_active IP Right Cessation
- 2001-08-07 US US09/925,883 patent/US7049325B2/en not_active Expired - Fee Related
- 2001-08-08 AR ARP010103784A patent/AR033554A1/es not_active Application Discontinuation
-
2003
- 2003-01-30 ZA ZA200300847A patent/ZA200300847B/en unknown
-
2005
- 2005-11-30 US US11/291,867 patent/US7186840B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2290161T3 (es) | 2008-02-16 |
| BR0113175A (pt) | 2004-02-17 |
| US20020082276A1 (en) | 2002-06-27 |
| US7049325B2 (en) | 2006-05-23 |
| AU2001277560A1 (en) | 2002-02-18 |
| DE60129445D1 (de) | 2007-08-30 |
| ZA200300847B (en) | 2004-04-30 |
| US20060084677A1 (en) | 2006-04-20 |
| US7186840B2 (en) | 2007-03-06 |
| CA2418832A1 (en) | 2002-02-14 |
| EP1313707B1 (en) | 2007-07-18 |
| WO2002012192A1 (en) | 2002-02-14 |
| AR033554A1 (es) | 2003-12-26 |
| ATE367379T1 (de) | 2007-08-15 |
| KR20030027016A (ko) | 2003-04-03 |
| JP3930428B2 (ja) | 2007-06-13 |
| CN1199950C (zh) | 2005-05-04 |
| EP1313707A1 (en) | 2003-05-28 |
| JP2004505951A (ja) | 2004-02-26 |
| DE60129445T2 (de) | 2008-04-24 |
| CN1466575A (zh) | 2004-01-07 |
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