PH26044A - Substituted naphthalene carboxylic acids - Google Patents
Substituted naphthalene carboxylic acids Download PDFInfo
- Publication number
- PH26044A PH26044A PH39658A PH39658A PH26044A PH 26044 A PH26044 A PH 26044A PH 39658 A PH39658 A PH 39658A PH 39658 A PH39658 A PH 39658A PH 26044 A PH26044 A PH 26044A
- Authority
- PH
- Philippines
- Prior art keywords
- hydrogen
- lower alkyl
- rio
- compound
- methyl
- Prior art date
Links
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical class C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 title description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 150
- 239000001257 hydrogen Substances 0.000 claims description 150
- 150000001875 compounds Chemical class 0.000 claims description 118
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 150000002431 hydrogen Chemical group 0.000 claims description 55
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- -1 2,3-dihydroxyphenyl Chemical group 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 125000002252 acyl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 229910052702 rhenium Inorganic materials 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004494 ethyl ester group Chemical group 0.000 claims description 9
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- MHQJFDYDSRISNY-UHFFFAOYSA-N 6-[6-(2,3-dihydroxyphenyl)hexoxy]naphthalene-2-carboxylic acid Chemical compound C1=CC2=CC(C(=O)O)=CC=C2C=C1OCCCCCCC1=CC=CC(O)=C1O MHQJFDYDSRISNY-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 91
- 239000000203 mixture Substances 0.000 description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 45
- 239000003921 oil Substances 0.000 description 42
- 235000019198 oils Nutrition 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
- 239000011541 reaction mixture Substances 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 38
- 230000002829 reductive effect Effects 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 32
- 229940073584 methylene chloride Drugs 0.000 description 30
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 27
- 239000002904 solvent Substances 0.000 description 26
- 238000004128 high performance liquid chromatography Methods 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 238000010992 reflux Methods 0.000 description 19
- 235000019441 ethanol Nutrition 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 15
- 238000001819 mass spectrum Methods 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
- 229960004756 ethanol Drugs 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 150000001793 charged compounds Chemical class 0.000 description 13
- 239000000284 extract Substances 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- 238000001228 spectrum Methods 0.000 description 13
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229960001407 sodium bicarbonate Drugs 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 9
- 235000009518 sodium iodide Nutrition 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 229940022682 acetone Drugs 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 230000037361 pathway Effects 0.000 description 8
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 8
- POHYPAHTFHBKTR-UHFFFAOYSA-N 1-(6-bromohexyl)-2,3-bis(phenylmethoxy)benzene Chemical compound C=1C=CC=CC=1COC=1C(CCCCCCBr)=CC=CC=1OCC1=CC=CC=C1 POHYPAHTFHBKTR-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229940063656 aluminum chloride Drugs 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 206010009887 colitis Diseases 0.000 description 6
- XWJUDDGELKXYNO-QMMMGPOBSA-N desmethylnaproxen Chemical compound C1=C(O)C=CC2=CC([C@@H](C(O)=O)C)=CC=C21 XWJUDDGELKXYNO-QMMMGPOBSA-N 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 239000002953 phosphate buffered saline Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 206010061218 Inflammation Diseases 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 229960000443 hydrochloric acid Drugs 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 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 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 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 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-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
- 229910052744 lithium Inorganic materials 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 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
- 210000004877 mucosa Anatomy 0.000 description 4
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- CZBWWODJZHOSHU-LJAQVGFWSA-N (2s)-2-[6-[6-[2,3-bis(phenylmethoxy)phenyl]hexoxy]naphthalen-2-yl]propanoic acid Chemical compound C1=CC2=CC([C@@H](C(O)=O)C)=CC=C2C=C1OCCCCCCC(C=1OCC=2C=CC=CC=2)=CC=CC=1OCC1=CC=CC=C1 CZBWWODJZHOSHU-LJAQVGFWSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- LTKSPZPBTADPFM-UHFFFAOYSA-N 1-(5-bromopentyl)-2,3-dimethoxybenzene Chemical compound COC1=CC=CC(CCCCCBr)=C1OC LTKSPZPBTADPFM-UHFFFAOYSA-N 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- GSURLQOKWRJLPY-UHFFFAOYSA-N 2-(1-methylnaphthalen-2-yl)acetic acid Chemical compound C1=CC=C2C(C)=C(CC(O)=O)C=CC2=C1 GSURLQOKWRJLPY-UHFFFAOYSA-N 0.000 description 3
- CZBWWODJZHOSHU-UHFFFAOYSA-N 2-[6-[6-[2,3-bis(phenylmethoxy)phenyl]hexoxy]naphthalen-2-yl]propanoic acid Chemical compound C1=CC2=CC(C(C(O)=O)C)=CC=C2C=C1OCCCCCCC(C=1OCC=2C=CC=CC=2)=CC=CC=1OCC1=CC=CC=C1 CZBWWODJZHOSHU-UHFFFAOYSA-N 0.000 description 3
- DQHMQVUPZMRDKN-UHFFFAOYSA-N 3-(6-bromohexyl)benzene-1,2-diol Chemical compound OC1=CC=CC(CCCCCCBr)=C1O DQHMQVUPZMRDKN-UHFFFAOYSA-N 0.000 description 3
- PXSLZAFTAHRCFV-UHFFFAOYSA-N 4-(6-bromohexyl)-1,2-bis(phenylmethoxy)benzene Chemical compound C=1C=CC=CC=1COC1=CC(CCCCCCBr)=CC=C1OCC1=CC=CC=C1 PXSLZAFTAHRCFV-UHFFFAOYSA-N 0.000 description 3
- QCNFNXGEAPXXBQ-UHFFFAOYSA-N 4-(6-bromohexyl)-1,2-dimethoxybenzene Chemical compound COC1=CC=C(CCCCCCBr)C=C1OC QCNFNXGEAPXXBQ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 108090001069 Chymopapain Proteins 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 229920000881 Modified starch Polymers 0.000 description 3
- 102000003896 Myeloperoxidases Human genes 0.000 description 3
- 108090000235 Myeloperoxidases Proteins 0.000 description 3
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 3
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 3
- 201000004681 Psoriasis Diseases 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 210000004969 inflammatory cell Anatomy 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 2
- MUJIAJQCEOAVGZ-UHFFFAOYSA-N 1-(6-bromohexyl)-2,3-dimethoxybenzene Chemical compound COC1=CC=CC(CCCCCCBr)=C1OC MUJIAJQCEOAVGZ-UHFFFAOYSA-N 0.000 description 2
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 2
- JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 description 2
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 2
- OTKJBRHPMHJJOA-UHFFFAOYSA-N 2-(5-bromopentyl)-1-chloro-3,4-dimethoxybenzene Chemical compound COC1=CC=C(Cl)C(CCCCCBr)=C1OC OTKJBRHPMHJJOA-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- JUSOJSZNQYVENH-UHFFFAOYSA-N 3-(5-bromopentyl)-1,2-dichloro-4,5-dimethoxybenzene Chemical compound COC1=CC(Cl)=C(Cl)C(CCCCCBr)=C1OC JUSOJSZNQYVENH-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- CNJONWGTMFWPDT-UHFFFAOYSA-N 4-(2,3-dimethoxyphenyl)butan-1-ol Chemical compound COC1=CC=CC(CCCCO)=C1OC CNJONWGTMFWPDT-UHFFFAOYSA-N 0.000 description 2
- BTSAKSUXEFQZCF-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)but-3-yn-1-ol Chemical compound COC1=CC=C(C#CCCO)C=C1OC BTSAKSUXEFQZCF-UHFFFAOYSA-N 0.000 description 2
- HGTHHDQDYLRWAH-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)butan-1-ol Chemical compound COC1=CC=C(CCCCO)C=C1OC HGTHHDQDYLRWAH-UHFFFAOYSA-N 0.000 description 2
- KTDOYJNNUSDTNK-UHFFFAOYSA-N 4-(6-bromohexyl)benzene-1,2-diol Chemical compound OC1=CC=C(CCCCCCBr)C=C1O KTDOYJNNUSDTNK-UHFFFAOYSA-N 0.000 description 2
- IXKZQAFRUJIBAO-UHFFFAOYSA-N 6-(2-chloro-3,4-dimethoxyphenyl)hexan-1-ol Chemical compound COC1=CC=C(CCCCCCO)C(Cl)=C1OC IXKZQAFRUJIBAO-UHFFFAOYSA-N 0.000 description 2
- GEDYTNADXWTJSU-UHFFFAOYSA-N 6-bromo-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)hexan-1-one Chemical compound COC1=C(C)C(C)=C(C(=O)CCCCCBr)C(C)=C1OC GEDYTNADXWTJSU-UHFFFAOYSA-N 0.000 description 2
- SNDQIPBGSZUJPY-UHFFFAOYSA-N 6-bromo-1-(3,4-dimethoxy-5-propan-2-ylphenyl)hexan-1-one Chemical compound COC1=CC(C(=O)CCCCCBr)=CC(C(C)C)=C1OC SNDQIPBGSZUJPY-UHFFFAOYSA-N 0.000 description 2
- FTBWBGSIRBQWHC-UHFFFAOYSA-N 6-bromo-1-(3,4-dimethoxyphenyl)hexan-1-one Chemical compound COC1=CC=C(C(=O)CCCCCBr)C=C1OC FTBWBGSIRBQWHC-UHFFFAOYSA-N 0.000 description 2
- HBPVGJGBRWIVSX-UHFFFAOYSA-N 6-bromohexanoyl chloride Chemical compound ClC(=O)CCCCCBr HBPVGJGBRWIVSX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/282,100 US4937373A (en) | 1988-12-08 | 1988-12-08 | Substituted naphthalene carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26044A true PH26044A (en) | 1994-01-29 |
Family
ID=23080114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH39658A PH26044A (en) | 1988-12-08 | 1989-12-08 | Substituted naphthalene carboxylic acids |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4937373A (xx) |
| EP (1) | EP0372385A3 (xx) |
| JP (1) | JPH02202847A (xx) |
| AU (1) | AU631822B2 (xx) |
| CA (1) | CA2004696A1 (xx) |
| DK (1) | DK615589A (xx) |
| NZ (1) | NZ231651A (xx) |
| PH (1) | PH26044A (xx) |
| ZA (1) | ZA899328B (xx) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5084575A (en) * | 1987-07-31 | 1992-01-28 | American Home Products Corporation | Quinoline substituted naphthalenepropionic acid derivatives as anti-inflammatory/antiallergic agents |
| EP0501579A1 (en) * | 1991-02-28 | 1992-09-02 | Merck Frosst Canada Inc. | Naphthalene lactones as inhibitors of leukotriene biosynthesis |
| EP0501578A1 (en) * | 1991-02-28 | 1992-09-02 | Merck Frosst Canada Inc. | Pyranylphenyl hydroxyalkylnaphthoic acids as inhibitors of leukotriene biosynthesis |
| US5227399A (en) * | 1991-02-28 | 1993-07-13 | Merck Frosst Canada, Inc. | Pyranylphenyl naphthalene lactones as inhibitors of leukotriene biosynthesis |
| US5281720A (en) * | 1991-02-28 | 1994-01-25 | Merck Frosst Canada, Inc. | Pyranylphenyl hydroxyalkylnaphthoic acids as inhibitors of leukotriene biosynthesis |
| DE4210332C1 (xx) * | 1992-03-30 | 1993-07-15 | Gruenenthal Gmbh, 5100 Aachen, De | |
| US5308852A (en) * | 1992-06-29 | 1994-05-03 | Merck Frosst Canada, Inc. | Heteroarylnaphthalenes as inhibitors of leukotriene biosynthesis |
| US5252599A (en) * | 1992-08-27 | 1993-10-12 | Merck Frosst Canada, Inc. | Heteroarylnaphthalene hydroxy acids as inhibitors of leukotriene biosynthesis |
| US5426109A (en) * | 1992-08-27 | 1995-06-20 | Merck Frosst Canada, Inc. | Phenylnaphthalene hydroxy acids |
| US5350744A (en) * | 1992-08-27 | 1994-09-27 | Merck Frosst Canada, Inc. | Phenylnaphthalene lactones as inhibitors of leukotriene biosynthesis |
| US5428060A (en) * | 1992-08-27 | 1995-06-27 | Merck Frosst Canada, Inc. | Heteroarylnaphthalene lactones as inhibitors of leukotriene biosynthesis |
| GB9420557D0 (en) * | 1994-10-12 | 1994-11-30 | Zeneca Ltd | Aromatic compounds |
| TW434240B (en) * | 1995-06-20 | 2001-05-16 | Zeneca Ltd | Aromatic compounds, preparation thereof and pharmaceutical composition comprising same |
| TW502026B (en) * | 1995-06-20 | 2002-09-11 | Zeneca Ltd | Aromatic compounds useful as antagonists of e-type prostaglandins, processes for the preparation thereof, pharmaceutical compositions comprising the compounds, and intermediates |
| US5834468A (en) * | 1995-07-07 | 1998-11-10 | Zeneca Limited | Substituted aryl and heteroaryl compounds as E-type prostaglandin antagonists |
| KR100370597B1 (ko) * | 2000-06-22 | 2003-02-05 | 박정일 | 산형매립초로부터 분리한 신규한 나프탈렌계 화합물 및이를 유효성분으로 하는 약학적 조성물 |
| WO2003104178A1 (en) * | 2002-06-07 | 2003-12-18 | Cortical Pty Ltd | Napththalene derivatives which inhibit the cytokine or biological activity of macrophage migration inhibitory factor (mif) |
| TW200837046A (en) * | 2006-11-08 | 2008-09-16 | Speedel Experimenta Ag | Process for preparing organic compounds |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2831887A (en) * | 1953-11-30 | 1958-04-22 | Searle & Co | Aralkoxynaphthalene deri vatives |
| IT1196334B (it) * | 1984-11-22 | 1988-11-16 | Alfa Chem Ital | Processo per la risoluzione ottica di miscugli racemi di acidi alfanaftil-propionici |
| LU85849A1 (fr) * | 1985-04-11 | 1986-11-05 | Cird | Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques |
| GB8610349D0 (en) * | 1986-04-28 | 1986-06-04 | Bdh Ltd | 6-hydroxy-2-naphthoic acid derivatives |
| JPH0796529B2 (ja) * | 1987-07-27 | 1995-10-18 | 三井東圧化学株式会社 | 光学活性化合物 |
| AU611699B2 (en) * | 1987-07-31 | 1991-06-20 | American Home Products Corporation | Naphthalene propionic acid derivatives |
| JPS6483050A (en) * | 1987-09-24 | 1989-03-28 | Mitsui Toatsu Chemicals | Optically active compound |
| DE3737179A1 (de) * | 1987-11-03 | 1989-05-18 | Bayer Ag | (6-(hetero)aryloxy-naphthalin-2-yl-oxy)-alkancarbonsaeure-derivate |
-
1988
- 1988-12-08 US US07/282,100 patent/US4937373A/en not_active Expired - Fee Related
-
1989
- 1989-11-29 EP EP19890122074 patent/EP0372385A3/de not_active Ceased
- 1989-12-06 ZA ZA899328A patent/ZA899328B/xx unknown
- 1989-12-06 DK DK615589A patent/DK615589A/da not_active Application Discontinuation
- 1989-12-06 NZ NZ231651A patent/NZ231651A/en unknown
- 1989-12-06 AU AU45977/89A patent/AU631822B2/en not_active Ceased
- 1989-12-06 CA CA002004696A patent/CA2004696A1/en not_active Abandoned
- 1989-12-08 PH PH39658A patent/PH26044A/en unknown
- 1989-12-08 JP JP1320392A patent/JPH02202847A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK615589A (da) | 1990-06-09 |
| EP0372385A2 (de) | 1990-06-13 |
| EP0372385A3 (de) | 1991-06-19 |
| CA2004696A1 (en) | 1990-06-08 |
| AU4597789A (en) | 1990-06-14 |
| AU631822B2 (en) | 1992-12-10 |
| DK615589D0 (da) | 1989-12-06 |
| US4937373A (en) | 1990-06-26 |
| ZA899328B (en) | 1990-08-29 |
| JPH02202847A (ja) | 1990-08-10 |
| NZ231651A (en) | 1992-03-26 |
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