SI9500392A - 5-lipoxygenase inhibitors. - Google Patents
5-lipoxygenase inhibitors. Download PDFInfo
- Publication number
- SI9500392A SI9500392A SI9500392A SI9500392A SI9500392A SI 9500392 A SI9500392 A SI 9500392A SI 9500392 A SI9500392 A SI 9500392A SI 9500392 A SI9500392 A SI 9500392A SI 9500392 A SI9500392 A SI 9500392A
- Authority
- SI
- Slovenia
- Prior art keywords
- alkyl
- halo
- substituted
- pyran
- phenyl
- Prior art date
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- 239000000867 Lipoxygenase Inhibitor Substances 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 137
- -1 hydroxy, cyano, amino Chemical group 0.000 claims abstract description 79
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 16
- 125000005843 halogen group Chemical group 0.000 claims abstract description 16
- 125000001424 substituent group Chemical group 0.000 claims abstract description 14
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 7
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 6
- 239000004480 active ingredient Substances 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims abstract description 5
- 206010020751 Hypersensitivity Diseases 0.000 claims abstract description 5
- 241000124008 Mammalia Species 0.000 claims abstract description 5
- 230000007815 allergy Effects 0.000 claims abstract description 5
- 125000004429 atom Chemical group 0.000 claims abstract description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 5
- 125000005564 oxazolylene group Chemical group 0.000 claims abstract description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 5
- 125000005551 pyridylene group Chemical group 0.000 claims abstract description 5
- 125000005557 thiazolylene group Chemical group 0.000 claims abstract description 5
- 125000005556 thienylene group Chemical group 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims abstract description 3
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims abstract description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims abstract 2
- 125000001041 indolyl group Chemical group 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 230
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims description 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 7
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 claims description 4
- VPTONMHDLLMOOV-UHFFFAOYSA-N 4-[3-[4-(2-methylimidazol-1-yl)phenyl]sulfanylphenyl]oxane-4-carboxamide Chemical compound CC1=NC=CN1C(C=C1)=CC=C1SC1=CC=CC(C2(CCOCC2)C(N)=O)=C1 VPTONMHDLLMOOV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- VIIMIHGRUTXXBD-UHFFFAOYSA-N 4-[3-[4-(pyrrol-1-ylmethyl)phenyl]sulfanylphenyl]oxane-4-carboxamide Chemical compound C=1C=CC(SC=2C=CC(CN3C=CC=C3)=CC=2)=CC=1C1(C(=O)N)CCOCC1 VIIMIHGRUTXXBD-UHFFFAOYSA-N 0.000 claims description 2
- 230000000172 allergic effect Effects 0.000 claims description 2
- 208000010668 atopic eczema Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000004968 inflammatory condition Effects 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- DGOYLVBDCVINQZ-UHFFFAOYSA-N oxane-4-carboxamide Chemical compound NC(=O)C1CCOCC1 DGOYLVBDCVINQZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 abstract 1
- 208000026935 allergic disease Diseases 0.000 abstract 1
- 208000027866 inflammatory disease Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
- 238000005481 NMR spectroscopy Methods 0.000 description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 239000000203 mixture Substances 0.000 description 58
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 44
- 238000000034 method Methods 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
- 239000012267 brine Substances 0.000 description 33
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000002244 precipitate Substances 0.000 description 29
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 28
- 235000019341 magnesium sulphate Nutrition 0.000 description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
- 239000007787 solid Substances 0.000 description 24
- 239000000284 extract Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- WTOCSHWGOZQZQQ-UHFFFAOYSA-N ethyl 2-(3-fluoro-5-phenylmethoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC(F)=CC(OCC=2C=CC=CC=2)=C1 WTOCSHWGOZQZQQ-UHFFFAOYSA-N 0.000 description 7
- SNAQPKWTPCDKQR-UHFFFAOYSA-N ethyl 4-[3-fluoro-5-[[4-(2-methylimidazol-1-yl)phenyl]methoxy]phenyl]oxane-4-carboxylate Chemical compound C=1C(F)=CC(OCC=2C=CC(=CC=2)N2C(=NC=C2)C)=CC=1C1(C(=O)OCC)CCOCC1 SNAQPKWTPCDKQR-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- WHLPQLRCPSXNEZ-UHFFFAOYSA-N ethyl 4-(3-fluoro-5-phenylmethoxyphenyl)oxane-4-carboxylate Chemical compound C=1C(F)=CC(OCC=2C=CC=CC=2)=CC=1C1(C(=O)OCC)CCOCC1 WHLPQLRCPSXNEZ-UHFFFAOYSA-N 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- ZWIIPKTYHOPGIG-UHFFFAOYSA-N 1-[4-(chloromethyl)phenyl]-2-methylimidazole;hydrochloride Chemical compound Cl.CC1=NC=CN1C1=CC=C(CCl)C=C1 ZWIIPKTYHOPGIG-UHFFFAOYSA-N 0.000 description 5
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 5
- 102000003820 Lipoxygenases Human genes 0.000 description 5
- 108090000128 Lipoxygenases Proteins 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 5
- AVPKHOTUOHDTLW-UHFFFAOYSA-N oxane-4-carboxylic acid Chemical compound OC(=O)C1CCOCC1 AVPKHOTUOHDTLW-UHFFFAOYSA-N 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229940114079 arachidonic acid Drugs 0.000 description 4
- 235000021342 arachidonic acid Nutrition 0.000 description 4
- 229910052681 coesite Inorganic materials 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 229910052906 cristobalite Inorganic materials 0.000 description 4
- WSNKLYIWJLWVDJ-UHFFFAOYSA-N ethyl 4-(3-fluoro-5-hydroxyphenyl)oxane-4-carboxylate Chemical compound C=1C(O)=CC(F)=CC=1C1(C(=O)OCC)CCOCC1 WSNKLYIWJLWVDJ-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 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
- 239000000377 silicon dioxide Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 229910052682 stishovite Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 229910052905 tridymite Inorganic materials 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- REVPKMONQSPHGF-UHFFFAOYSA-N 1-(4-iodophenyl)-2-methylimidazole Chemical compound CC1=NC=CN1C1=CC=C(I)C=C1 REVPKMONQSPHGF-UHFFFAOYSA-N 0.000 description 3
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 3
- QVCJYNZQZXKOCN-UHFFFAOYSA-N 4-[3-[4-(2-methylimidazol-1-yl)phenyl]sulfanylphenyl]oxane-4-carboxylic acid Chemical compound CC1=NC=CN1C(C=C1)=CC=C1SC1=CC=CC(C2(CCOCC2)C(O)=O)=C1 QVCJYNZQZXKOCN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
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- 150000001768 cations Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- XRLDSWLMHUQECH-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1CCCC1 XRLDSWLMHUQECH-UHFFFAOYSA-N 0.000 description 3
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- KMIXQRTUEYLWJW-UHFFFAOYSA-N ethyl 4-[3-[4-(2-methylimidazol-1-yl)phenyl]sulfanylphenyl]oxane-4-carboxylate Chemical compound C=1C=CC(SC=2C=CC(=CC=2)N2C(=NC=C2)C)=CC=1C1(C(=O)OCC)CCOCC1 KMIXQRTUEYLWJW-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 3
- SEZGTMZGDDDWKN-UHFFFAOYSA-N methyl 1-(3-fluoro-5-methoxyphenyl)cyclopent-3-ene-1-carboxylate Chemical compound C=1C(F)=CC(OC)=CC=1C1(C(=O)OC)CC=CC1 SEZGTMZGDDDWKN-UHFFFAOYSA-N 0.000 description 3
- KTJFGMKBXRSHFX-UHFFFAOYSA-N methyl 2-(3-fluoro-5-methoxyphenyl)acetate Chemical compound COC(=O)CC1=CC(F)=CC(OC)=C1 KTJFGMKBXRSHFX-UHFFFAOYSA-N 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
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- QYTPZHFPGSBJJU-UHFFFAOYSA-N 1-(3-hydroxyphenyl)cyclopentane-1-carboxamide Chemical compound C=1C=CC(O)=CC=1C1(C(=O)N)CCCC1 QYTPZHFPGSBJJU-UHFFFAOYSA-N 0.000 description 2
- PXSHJLGMSITNOP-UHFFFAOYSA-N 2-(2,5-difluoro-3-methoxyphenyl)acetonitrile Chemical compound COC1=CC(F)=CC(CC#N)=C1F PXSHJLGMSITNOP-UHFFFAOYSA-N 0.000 description 2
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- MSRAZUGPWHWDHN-UHFFFAOYSA-N 2h-pyran-4-carboxylic acid Chemical compound OC(=O)C1=CCOC=C1 MSRAZUGPWHWDHN-UHFFFAOYSA-N 0.000 description 2
- KPPATEAUQLUXHN-UHFFFAOYSA-N 3-[tert-butyl(dimethyl)silyl]oxy-2,5-difluorobenzaldehyde Chemical compound CC(C)(C)[Si](C)(C)OC1=CC(F)=CC(C=O)=C1F KPPATEAUQLUXHN-UHFFFAOYSA-N 0.000 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
- YQDNBVODWMMCMI-UHFFFAOYSA-N 3-fluoro-5-[4-(1-hydroxyethyl)oxan-4-yl]phenol Chemical compound C=1C(O)=CC(F)=CC=1C1(C(O)C)CCOCC1 YQDNBVODWMMCMI-UHFFFAOYSA-N 0.000 description 2
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- PKMDIVSLKFUBIS-UHFFFAOYSA-N methyl 2-(3-fluoro-5-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC(O)=CC(F)=C1 PKMDIVSLKFUBIS-UHFFFAOYSA-N 0.000 description 1
- KSSDATBGROGULK-UHFFFAOYSA-N methyl 2-phenylethaneperoxoate Chemical compound COOC(=O)CC1=CC=CC=C1 KSSDATBGROGULK-UHFFFAOYSA-N 0.000 description 1
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- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
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- 239000002243 precursor Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
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- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- SCLRYYDLDQIZJH-UHFFFAOYSA-N tert-butyl-(2,5-difluorophenoxy)-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC(F)=CC=C1F SCLRYYDLDQIZJH-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9401747 | 1994-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI9500392A true SI9500392A (en) | 1996-08-31 |
Family
ID=14098722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9500392A SI9500392A (en) | 1994-10-18 | 1995-10-17 | 5-lipoxygenase inhibitors. |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP0787127B1 (cs) |
| JP (1) | JP3032579B2 (cs) |
| CN (1) | CN1093536C (cs) |
| AT (1) | ATE198474T1 (cs) |
| AU (1) | AU681520B2 (cs) |
| BG (1) | BG61768B1 (cs) |
| CA (1) | CA2202057C (cs) |
| CO (1) | CO4480026A1 (cs) |
| CZ (1) | CZ287350B6 (cs) |
| DE (1) | DE69519804T2 (cs) |
| DK (1) | DK0787127T3 (cs) |
| ES (1) | ES2153033T3 (cs) |
| FI (1) | FI971632A0 (cs) |
| GR (1) | GR3035471T3 (cs) |
| HU (1) | HU221543B (cs) |
| IL (1) | IL115581A (cs) |
| LV (1) | LV11468B (cs) |
| MY (1) | MY114680A (cs) |
| NO (1) | NO314629B1 (cs) |
| NZ (1) | NZ285163A (cs) |
| PE (1) | PE49196A1 (cs) |
| PL (1) | PL180104B1 (cs) |
| RU (1) | RU2136666C1 (cs) |
| SI (1) | SI9500392A (cs) |
| SK (1) | SK281577B6 (cs) |
| TR (1) | TR199501274A2 (cs) |
| TW (1) | TW411339B (cs) |
| UA (1) | UA45312C2 (cs) |
| WO (1) | WO1996011911A1 (cs) |
| YU (1) | YU65995A (cs) |
| ZA (1) | ZA958748B (cs) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6239285B1 (en) | 1998-02-06 | 2001-05-29 | Pfizer Inc | Process for making 5-lipoxygenase inhibitors having varied heterocyclic ring systems |
| US6194585B1 (en) * | 1998-12-22 | 2001-02-27 | Pfizer Inc. | Process for preparing 5-lipoxygenase inhibitors |
| US6344563B1 (en) | 1999-08-31 | 2002-02-05 | Timothy Norris | Process for making 5-lipoxygenase inhibitors having varied heterocyclic ring systems |
| US6346624B1 (en) * | 1999-08-31 | 2002-02-12 | Pfizer Inc | Process for making 5-lipoxygenase inhibitors having varied heterocyclic ring systems |
| SG87145A1 (en) * | 1999-08-31 | 2002-03-19 | Pfizer Prod Inc | Process for making 5-lipoxygenase inhibitors having varied heterocyclic ring systems |
| CZ303632B6 (cs) * | 2000-03-24 | 2013-01-23 | Euro-Celtique S.A. | Arylem substituované pyrazoly, triazoly a tetrazoly a jejich pouzití |
| EP1383874B1 (en) * | 2001-04-20 | 2009-12-23 | Novozymes A/S | Variants of lipoxygenase and their use |
| GB0302094D0 (en) | 2003-01-29 | 2003-02-26 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| GB0324269D0 (en) | 2003-10-16 | 2003-11-19 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| RS20090211A (sr) * | 2006-11-27 | 2010-10-31 | Pfizer Products Inc. | Analozi pirazola |
| EA201000703A1 (ru) * | 2007-11-26 | 2010-12-30 | Пфайзер Инк. | Производные пиразола в качестве ингибиторов 5-lo |
| MX2014010272A (es) * | 2012-02-28 | 2015-08-14 | Piramal Entpr Ltd | Derivados del acido fenil alcanoico como agonistas gpr. |
| TWI827583B (zh) | 2018-03-08 | 2024-01-01 | 美商英塞特公司 | 作為ＰＩ３Ｋ-γ抑制劑之胺基吡嗪二醇化合物 |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2001730A6 (es) * | 1987-01-14 | 1988-06-01 | Ferrer Int | Procedimiento de obtencion del acio 2,3-dihidro-5-(b-(1h-imidazol-1-il) etoxi)-1h-inden-1-carboxilico |
| EP0462830B1 (en) * | 1990-06-21 | 1995-10-18 | Zeneca Limited | Cyclic ether derivatives |
| IE913866A1 (en) * | 1990-11-28 | 1992-06-03 | Ici Plc | Aryl derivatives |
| EP0505122A1 (en) * | 1991-03-21 | 1992-09-23 | Zeneca Limited | Alpha, alpha-dialkylbenzyl derivatives |
| EP0540165A1 (en) * | 1991-10-03 | 1993-05-05 | Zeneca Limited | Alkanoic acid derivatives |
| KR100190728B1 (ko) * | 1993-06-14 | 1999-06-01 | 디. 제이. 우드, 스피겔 알렌 제이 | 이미다졸 리폭시게나제 저해제 |
-
1994
- 1994-10-18 SK SK1287-95A patent/SK281577B6/sk unknown
-
1995
- 1995-05-29 CZ CZ19971177A patent/CZ287350B6/cs not_active IP Right Cessation
- 1995-05-29 PL PL95319727A patent/PL180104B1/pl not_active IP Right Cessation
- 1995-05-29 EP EP95918121A patent/EP0787127B1/en not_active Expired - Lifetime
- 1995-05-29 WO PCT/IB1995/000408 patent/WO1996011911A1/en not_active Ceased
- 1995-05-29 CA CA002202057A patent/CA2202057C/en not_active Expired - Fee Related
- 1995-05-29 NZ NZ285163A patent/NZ285163A/en unknown
- 1995-05-29 DE DE69519804T patent/DE69519804T2/de not_active Expired - Fee Related
- 1995-05-29 HU HU9701853A patent/HU221543B/hu not_active IP Right Cessation
- 1995-05-29 CN CN95195926A patent/CN1093536C/zh not_active Expired - Fee Related
- 1995-05-29 RU RU97106099/04A patent/RU2136666C1/ru not_active IP Right Cessation
- 1995-05-29 JP JP8513058A patent/JP3032579B2/ja not_active Expired - Fee Related
- 1995-05-29 DK DK95918121T patent/DK0787127T3/da active
- 1995-05-29 ES ES95918121T patent/ES2153033T3/es not_active Expired - Lifetime
- 1995-05-29 AU AU24174/95A patent/AU681520B2/en not_active Ceased
- 1995-05-29 AT AT95918121T patent/ATE198474T1/de not_active IP Right Cessation
- 1995-09-12 TW TW084109522A patent/TW411339B/zh not_active IP Right Cessation
- 1995-10-02 CO CO95045652A patent/CO4480026A1/es unknown
- 1995-10-12 IL IL11558195A patent/IL115581A/xx not_active IP Right Cessation
- 1995-10-13 UA UA95104510A patent/UA45312C2/uk unknown
- 1995-10-16 MY MYPI95003103A patent/MY114680A/en unknown
- 1995-10-17 YU YU65995A patent/YU65995A/sh unknown
- 1995-10-17 SI SI9500392A patent/SI9500392A/sl unknown
- 1995-10-17 LV LVP-95-313A patent/LV11468B/en unknown
- 1995-10-17 PE PE1995282113A patent/PE49196A1/es not_active Application Discontinuation
- 1995-10-17 ZA ZA958748A patent/ZA958748B/xx unknown
- 1995-10-18 BG BG100070A patent/BG61768B1/bg unknown
- 1995-10-18 TR TR95/01274A patent/TR199501274A2/xx unknown
-
1997
- 1997-04-17 NO NO19971773A patent/NO314629B1/no unknown
- 1997-04-17 FI FI971632A patent/FI971632A0/fi not_active IP Right Cessation
-
2001
- 2001-02-23 GR GR20010400310T patent/GR3035471T3/el not_active IP Right Cessation
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