PH26574A - 5-lopoxygenase inhibiting 4-(4-phenyl-1-piperazinyl) phenols - Google Patents
5-lopoxygenase inhibiting 4-(4-phenyl-1-piperazinyl) phenols Download PDFInfo
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- PH26574A PH26574A PH38255A PH38255A PH26574A PH 26574 A PH26574 A PH 26574A PH 38255 A PH38255 A PH 38255A PH 38255 A PH38255 A PH 38255A PH 26574 A PH26574 A PH 26574A
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- Philippines
- Prior art keywords
- galkyl
- parts
- formula
- aryl
- radical
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- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 10
- QPANQEGICMMPRR-UHFFFAOYSA-N 4-(4-phenylpiperazin-1-yl)phenol Chemical class C1=CC(O)=CC=C1N1CCN(C=2C=CC=CC=2)CC1 QPANQEGICMMPRR-UHFFFAOYSA-N 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract description 88
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 19
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims abstract description 15
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims abstract description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
- 239000004480 active ingredient Substances 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 81
- -1 nitro, amino Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- OSKCITFPVIJNIJ-UHFFFAOYSA-N 5-butan-2-yl-1,2,4-triazol-3-one Chemical compound CCC(C)C1=NC(=O)N=N1 OSKCITFPVIJNIJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 208000037765 diseases and disorders Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 5
- 150000002989 phenols Chemical class 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- 239000000047 product Substances 0.000 description 76
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 59
- 239000000243 solution Substances 0.000 description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 150000003254 radicals Chemical class 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 31
- 239000003480 eluent Substances 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- 238000001816 cooling Methods 0.000 description 23
- 239000000543 intermediate Substances 0.000 description 23
- 238000003756 stirring Methods 0.000 description 22
- 239000007787 solid Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 229960001701 chloroform Drugs 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- 125000005843 halogen group Chemical group 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 13
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 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 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- 102000003820 Lipoxygenases Human genes 0.000 description 8
- 108090000128 Lipoxygenases Proteins 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000002617 leukotrienes Chemical class 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229920002307 Dextran Polymers 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 229940114079 arachidonic acid Drugs 0.000 description 5
- 235000021342 arachidonic acid Nutrition 0.000 description 5
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 210000005069 ears Anatomy 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- KMVPXBDOWDXXEN-UHFFFAOYSA-N 4-nitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1 KMVPXBDOWDXXEN-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 101150023090 CAH gene Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 238000007126 N-alkylation reaction Methods 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- XEXFMTLVGVELAA-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-4-methoxyaniline Chemical compound COC1=CC=C(N(CCCl)CCCl)C=C1 XEXFMTLVGVELAA-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 4
- 239000008194 pharmaceutical composition 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
- 230000003389 potentiating effect Effects 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- ZVRXDYHMCJQEFP-UHFFFAOYSA-N 1-(4-isothiocyanatophenyl)-4-(4-methoxyphenyl)piperazine Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(=CC=2)N=C=S)CC1 ZVRXDYHMCJQEFP-UHFFFAOYSA-N 0.000 description 3
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 102000011730 Arachidonate 12-Lipoxygenase Human genes 0.000 description 3
- 108010076676 Arachidonate 12-lipoxygenase Proteins 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
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- 238000009835 boiling Methods 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000006900 dealkylation reaction Methods 0.000 description 3
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- 230000004054 inflammatory process Effects 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- BBFPAWVWKPGXTA-UHFFFAOYSA-N 1-(2,2-dimethoxyethyl)-3-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]thiourea Chemical compound C1=CC(NC(=S)NCC(OC)OC)=CC=C1N1CCN(C=2C=CC(OC)=CC=2)CC1 BBFPAWVWKPGXTA-UHFFFAOYSA-N 0.000 description 2
- ZESMYJSRHBSHEE-UHFFFAOYSA-N 1-(4-aminophenyl)-3-ethylpyrimidine-2,4-dione Chemical compound O=C1N(CC)C(=O)C=CN1C1=CC=C(N)C=C1 ZESMYJSRHBSHEE-UHFFFAOYSA-N 0.000 description 2
- IUEJPGLGKJDIRU-UHFFFAOYSA-N 1-(4-nitrophenyl)pyrimidine-2,4-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(=O)NC(=O)C=C1 IUEJPGLGKJDIRU-UHFFFAOYSA-N 0.000 description 2
- WKLIAXFVRMZLIN-UHFFFAOYSA-N 1-amino-3-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]thiourea Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(NC(=S)NN)=CC=2)CC1 WKLIAXFVRMZLIN-UHFFFAOYSA-N 0.000 description 2
- FGWSTEBBICTTDP-UHFFFAOYSA-N 2,2,2-trifluoroethyl naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)OCC(F)(F)F)=CC=C21 FGWSTEBBICTTDP-UHFFFAOYSA-N 0.000 description 2
- MLORCSNXINFAMQ-UHFFFAOYSA-N 2-(4-aminophenyl)-4-butyl-1,2,4-triazine-3,5-dione Chemical compound O=C1N(CCCC)C(=O)C=NN1C1=CC=C(N)C=C1 MLORCSNXINFAMQ-UHFFFAOYSA-N 0.000 description 2
- HZMWGMJTNJGRGT-UHFFFAOYSA-N 2-(4-aminophenyl)-5-methyl-4-propyl-1,2,4-triazol-3-one Chemical compound O=C1N(CCC)C(C)=NN1C1=CC=C(N)C=C1 HZMWGMJTNJGRGT-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- SJIKNQWCDVQSPW-UHFFFAOYSA-N 3-ethyl-1-(4-nitrophenyl)pyrimidine-2,4-dione Chemical compound O=C1N(CC)C(=O)C=CN1C1=CC=C([N+]([O-])=O)C=C1 SJIKNQWCDVQSPW-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
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- A61P11/08—Bronchodilators
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US16182588A | 1988-02-29 | 1988-02-29 |
Publications (1)
Publication Number | Publication Date |
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PH26574A true PH26574A (en) | 1992-08-19 |
Family
ID=22582912
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PH38255A PH26574A (en) | 1988-02-29 | 1989-02-28 | 5-lopoxygenase inhibiting 4-(4-phenyl-1-piperazinyl) phenols |
Country Status (26)
Country | Link |
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US (1) | US4931444A (ko) |
EP (1) | EP0331232B1 (ko) |
JP (1) | JPH075564B2 (ko) |
KR (1) | KR0133074B1 (ko) |
CN (1) | CN1021223C (ko) |
AT (1) | ATE105711T1 (ko) |
AU (1) | AU615519B2 (ko) |
BG (1) | BG49940A3 (ko) |
CA (1) | CA1331757C (ko) |
DE (1) | DE68915308T2 (ko) |
DK (1) | DK91889A (ko) |
ES (1) | ES2056190T3 (ko) |
FI (1) | FI97383C (ko) |
HU (2) | HU9303071D0 (ko) |
IE (1) | IE63150B1 (ko) |
IL (1) | IL89426A (ko) |
JO (1) | JO1559B1 (ko) |
MA (1) | MA21502A1 (ko) |
MY (1) | MY103802A (ko) |
NO (1) | NO174049C (ko) |
NZ (1) | NZ228016A (ko) |
PH (1) | PH26574A (ko) |
PT (1) | PT89875B (ko) |
RU (1) | RU2107064C1 (ko) |
TN (1) | TNSN89019A1 (ko) |
ZA (1) | ZA891547B (ko) |
Families Citing this family (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2631625B1 (fr) * | 1988-05-17 | 1992-10-16 | Synthelabo | Derives de phenyl-6 piperazinylalkyl-3 1h,3h-pyrimidinedione-2,4, leur preparation et leur application en therapeutique |
CA2076257A1 (en) * | 1991-09-13 | 1993-03-14 | Jan Heeres | 4-¬4-¬4-(4-hydroxyphenyl)-1- piperazinyl|phenyl|-5-methyl-3h -1,2,4-triazol-3-one derivatives |
IL103558A0 (en) * | 1991-10-30 | 1993-03-15 | Schering Corp | Tri-substituted tetrahydrofuran antifungals |
GR1001394B (el) * | 1992-10-12 | 1993-10-29 | Janssen Pharmaceutica Nv | Παράγωγα 4-[4-[4-(4-υδροξυφαινυλ)-1-πιπεραζινυλ] φαινυλ]-5-με?υλ3Η-1,2,4-τριαζολ-3-όνης. |
TW279864B (ko) * | 1993-02-19 | 1996-07-01 | Janssen Pharmaceutica Nv | |
JP3075451B2 (ja) * | 1993-05-19 | 2000-08-14 | 矢崎総業株式会社 | レバー式コネクタ |
FR2705959B1 (fr) * | 1993-06-01 | 1995-08-11 | Oreal | Procédé de synthèse stéréospécifique de leucotriène B4 sous sa configuration 6Z, 8E, 10E et produits intermédiaires. |
FR2707294B1 (fr) * | 1993-07-06 | 1995-09-29 | Pf Medicament | Nouveaux dérivés de la 3,5-dioxo-(2H,4H)-1,2,4-triazine, leur préparation et leur application en thérapeutique humaine. |
GB9326232D0 (en) * | 1993-12-23 | 1994-02-23 | Zeneca Ltd | Chemical compounds |
GB9326373D0 (en) * | 1993-12-23 | 1994-02-23 | Zeneca Ltd | Chemical compounds |
ATE207910T1 (de) * | 1994-04-06 | 2001-11-15 | Janssen Pharmaceutica Nv | Anti-helicobacter ester- oder carbamatderivate von azolonen |
US5607932A (en) * | 1994-07-12 | 1997-03-04 | Janssen Pharmaceutica N.V. | Heterocyclic derivatives of azolones |
US5637592A (en) * | 1994-07-12 | 1997-06-10 | Janssen Pharmaceutica N.V. | Acyl derivatives of azolones |
US5571811A (en) * | 1994-07-12 | 1996-11-05 | Janssen Pharmaceutica N.V. | Sulfonamide derivatives of azolones |
US5639754A (en) * | 1994-07-12 | 1997-06-17 | Janssen Pharmaceutica N.V. | Urea and thiourea derivatives of azolones |
US5635514A (en) * | 1994-10-25 | 1997-06-03 | G. D. Searle & Company | Heteroaralkyl and heteroarylthioalkyl thiophenolic compounds as 5-lipoxgenase inhibitors |
US5521186A (en) * | 1994-10-27 | 1996-05-28 | Janssen Pharmaceutica N.V. | Apolipoprotein-β synthesis inhibitors |
SK281908B6 (sk) * | 1994-10-27 | 2001-09-11 | Janssen Pharmaceutica N. V. | Heteroarylsubstituované deriváty 1,3-dioxolan-4-ylmetoxyfenyl-1- piperazinylfenyl-2,4-dihydro-2-alkyl-3h-1,2,4-triazol-3-ónu, spôsob a medziprodukty na ich výrobu a farmaceutické prostriedky |
US5859014A (en) * | 1995-06-09 | 1999-01-12 | Syntex (U.S.A.) Inc. | Pyrimidinedione, pyrimidinetrione, triazinedione and tetrahydroquinazolinedione derivatives as α1 -adrenergic receptor antagonists |
JP2001504465A (ja) | 1996-11-12 | 2001-04-03 | セプラコール,インク. | 2r,4s,s,s―および2s,4r,s,s―ヒドロキシイトラコナゾール |
CA2269617A1 (en) * | 1996-11-12 | 1998-05-22 | Chris H. Senanayake | 2r,4s,r,s- and 2s,4r,r,s-hydroxyitraconazole- and hydroxysaperconazole derivatives |
US6262052B1 (en) | 1997-02-11 | 2001-07-17 | Janssen Pharmaceutica N.V. | Amino acid ester containing azole antifungals |
NZ501627A (en) * | 1997-07-10 | 2002-02-01 | Janssen Pharmaceutica Nv | 3,5-dioxo-2(3H)-triazine derivatives substituted by 4-(phenylmethyl)phenyl useful as IL-5 inhibitors |
DE19822678A1 (de) * | 1998-05-20 | 1999-11-25 | Bayer Ag | Substituierte 1,3-Diaza-2-(thi)oxo-cycloalkane |
ATE365723T1 (de) | 1998-12-18 | 2007-07-15 | Janssen Pharmaceutica Nv | Il-5 hemmende 6-uracilderivate |
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1989
- 1989-01-10 CA CA000587830A patent/CA1331757C/en not_active Expired - Fee Related
- 1989-01-12 US US07/297,010 patent/US4931444A/en not_active Expired - Fee Related
- 1989-01-20 MY MYPI89000066A patent/MY103802A/en unknown
- 1989-02-16 NZ NZ228016A patent/NZ228016A/xx unknown
- 1989-02-20 JO JO19891559A patent/JO1559B1/en active
- 1989-02-20 JP JP1038486A patent/JPH075564B2/ja not_active Expired - Lifetime
- 1989-02-21 DE DE68915308T patent/DE68915308T2/de not_active Expired - Fee Related
- 1989-02-21 AT AT89200424T patent/ATE105711T1/de not_active IP Right Cessation
- 1989-02-21 EP EP89200424A patent/EP0331232B1/en not_active Expired - Lifetime
- 1989-02-21 ES ES89200424T patent/ES2056190T3/es not_active Expired - Lifetime
- 1989-02-24 AU AU30739/89A patent/AU615519B2/en not_active Ceased
- 1989-02-24 BG BG087409A patent/BG49940A3/xx unknown
- 1989-02-27 MA MA21746A patent/MA21502A1/fr unknown
- 1989-02-27 TN TNTNSN89019A patent/TNSN89019A1/fr unknown
- 1989-02-27 DK DK091889A patent/DK91889A/da not_active Application Discontinuation
- 1989-02-27 NO NO890813A patent/NO174049C/no unknown
- 1989-02-27 FI FI890931A patent/FI97383C/fi not_active IP Right Cessation
- 1989-02-27 IL IL89426A patent/IL89426A/xx not_active IP Right Cessation
- 1989-02-28 PT PT89875A patent/PT89875B/pt not_active IP Right Cessation
- 1989-02-28 RU SU4613548A patent/RU2107064C1/ru active
- 1989-02-28 HU HU9303071A patent/HU9303071D0/hu unknown
- 1989-02-28 IE IE64189A patent/IE63150B1/en not_active IP Right Cessation
- 1989-02-28 PH PH38255A patent/PH26574A/en unknown
- 1989-02-28 ZA ZA891547A patent/ZA891547B/xx unknown
- 1989-02-28 HU HU89927A patent/HUT52080A/hu unknown
- 1989-02-28 KR KR1019890002435A patent/KR0133074B1/ko not_active IP Right Cessation
- 1989-02-28 CN CN89100931A patent/CN1021223C/zh not_active Expired - Fee Related
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