JPH0379336B2 - - Google Patents
Info
- Publication number
- JPH0379336B2 JPH0379336B2 JP58203632A JP20363283A JPH0379336B2 JP H0379336 B2 JPH0379336 B2 JP H0379336B2 JP 58203632 A JP58203632 A JP 58203632A JP 20363283 A JP20363283 A JP 20363283A JP H0379336 B2 JPH0379336 B2 JP H0379336B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- group
- compound according
- sodium salt
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 154
- 239000002253 acid Substances 0.000 claims description 137
- -1 carboxymethoxy group Chemical group 0.000 claims description 132
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 55
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 43
- 159000000000 sodium salts Chemical class 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 27
- 239000005711 Benzoic acid Substances 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 235000010233 benzoic acid Nutrition 0.000 claims description 13
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 12
- 231100000252 nontoxic Toxicity 0.000 claims description 12
- 230000003000 nontoxic effect Effects 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 claims description 6
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 150000003857 carboxamides Chemical class 0.000 claims description 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- ZOELXJWPWNNTHY-UHFFFAOYSA-N 2-[(4-pentylbenzoyl)amino]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1C(=O)NC1=CC=CC=C1C(O)=O ZOELXJWPWNNTHY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- GAMRBCZMOOMBSQ-CCEZHUSRSA-N N-(p-amylcinnamoyl)anthranilic acid Chemical compound C1=CC(CCCCC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1C(O)=O GAMRBCZMOOMBSQ-CCEZHUSRSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 183
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 73
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 64
- 238000005481 NMR spectroscopy Methods 0.000 description 61
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
- 238000000034 method Methods 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 40
- 238000004809 thin layer chromatography Methods 0.000 description 39
- 230000000704 physical effect Effects 0.000 description 36
- 239000000203 mixture Substances 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 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 22
- 239000000243 solution Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000000746 purification Methods 0.000 description 21
- 238000010898 silica gel chromatography Methods 0.000 description 21
- 239000007858 starting material Substances 0.000 description 21
- 239000000126 substance Substances 0.000 description 21
- 239000012141 concentrate Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 235000008504 concentrate Nutrition 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 17
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
- 108010064785 Phospholipases Proteins 0.000 description 16
- 102000015439 Phospholipases Human genes 0.000 description 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 15
- 150000002617 leukotrienes Chemical class 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- 150000003180 prostaglandins Chemical class 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 241001024304 Mino Species 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- 239000000052 vinegar Substances 0.000 description 11
- 235000021419 vinegar Nutrition 0.000 description 11
- 229940114079 arachidonic acid Drugs 0.000 description 10
- 235000021342 arachidonic acid Nutrition 0.000 description 10
- 230000002401 inhibitory effect Effects 0.000 description 10
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 8
- LZUMEVGHGKCPJK-UHFFFAOYSA-N 3-(4-pentylphenyl)prop-2-enoic acid Chemical compound CCCCCC1=CC=C(C=CC(O)=O)C=C1 LZUMEVGHGKCPJK-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 7
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 7
- 108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 235000013985 cinnamic acid Nutrition 0.000 description 7
- 229930016911 cinnamic acid Natural products 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 7
- 230000037361 pathway Effects 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- AMVRSHNTGTWNLY-UHFFFAOYSA-N 2-amino-2-phenoxyacetic acid Chemical compound OC(=O)C(N)OC1=CC=CC=C1 AMVRSHNTGTWNLY-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 206010020751 Hypersensitivity Diseases 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 208000026935 allergic disease Diseases 0.000 description 6
- 230000000172 allergic effect Effects 0.000 description 6
- 125000005427 anthranyl group Chemical group 0.000 description 6
- 208000010668 atopic eczema Diseases 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 6
- 208000002874 Acne Vulgaris Diseases 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 206010000496 acne Diseases 0.000 description 5
- 230000007815 allergy Effects 0.000 description 5
- 230000003042 antagnostic effect Effects 0.000 description 5
- 208000006673 asthma Diseases 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 210000004072 lung Anatomy 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000012746 preparative thin layer chromatography Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 4
- KPIVDNYJNOPGBE-UHFFFAOYSA-N 2-aminonicotinic acid Chemical compound NC1=NC=CC=C1C(O)=O KPIVDNYJNOPGBE-UHFFFAOYSA-N 0.000 description 4
- 201000004384 Alopecia Diseases 0.000 description 4
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 4
- 208000007536 Thrombosis Diseases 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 231100000360 alopecia Toxicity 0.000 description 4
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- JLWMMYZWEHHTFF-UHFFFAOYSA-N 2-[6-(3-carbamimidoylphenoxy)-4-[di(propan-2-yl)amino]-3,5-difluoropyridin-2-yl]oxy-5-(2-methylpropylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC(C(=O)NCC(C)C)=CC=C1OC1=NC(OC=2C=C(C=CC=2)C(N)=N)=C(F)C(N(C(C)C)C(C)C)=C1F JLWMMYZWEHHTFF-UHFFFAOYSA-N 0.000 description 3
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 102000003820 Lipoxygenases Human genes 0.000 description 3
- 108090000128 Lipoxygenases Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 208000027515 Tracheal disease Diseases 0.000 description 3
- 102000014384 Type C Phospholipases Human genes 0.000 description 3
- 108010079194 Type C Phospholipases Proteins 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 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
- 230000006378 damage Effects 0.000 description 3
- 150000002085 enols Chemical class 0.000 description 3
- 239000005556 hormone Substances 0.000 description 3
- 229940088597 hormone Drugs 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 3
- 230000037353 metabolic pathway Effects 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 239000003428 phospholipase inhibitor Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000001568 sexual effect Effects 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- NITWSHWHQAQBAW-QPJJXVBHSA-N (E)-4-coumaric acid methyl ester Chemical compound COC(=O)\C=C\C1=CC=C(O)C=C1 NITWSHWHQAQBAW-QPJJXVBHSA-N 0.000 description 2
- KAMZUSZBMGHSEB-UHFFFAOYSA-N 3-(4-octoxyphenyl)prop-2-enoic acid Chemical compound CCCCCCCCOC1=CC=C(C=CC(O)=O)C=C1 KAMZUSZBMGHSEB-UHFFFAOYSA-N 0.000 description 2
- AJFPXCKPARAFNO-UHFFFAOYSA-N 3-decylbenzoic acid Chemical compound CCCCCCCCCCC1=CC=CC(C(O)=O)=C1 AJFPXCKPARAFNO-UHFFFAOYSA-N 0.000 description 2
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 2
- RTRTWCIWPQFYDU-UHFFFAOYSA-N 4-decylbenzoic acid Chemical compound CCCCCCCCCCC1=CC=C(C(O)=O)C=C1 RTRTWCIWPQFYDU-UHFFFAOYSA-N 0.000 description 2
- CWYNKKGQJYAHQG-UHFFFAOYSA-N 4-pentylbenzoic acid Chemical compound CCCCCC1=CC=C(C(O)=O)C=C1 CWYNKKGQJYAHQG-UHFFFAOYSA-N 0.000 description 2
- JNUUNUQHXIOFDA-XTDASVJISA-N 5-HPETE Chemical compound CCCCC\C=C/C\C=C/C\C=C/C=C/C(OO)CCCC(O)=O JNUUNUQHXIOFDA-XTDASVJISA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
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- YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical class 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20363283A JPS6097946A (ja) | 1983-11-01 | 1983-11-01 | カルボキサミド誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20363283A JPS6097946A (ja) | 1983-11-01 | 1983-11-01 | カルボキサミド誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6097946A JPS6097946A (ja) | 1985-05-31 |
| JPH0379336B2 true JPH0379336B2 (US07368563-20080506-C00056.png) | 1991-12-18 |
Family
ID=16477256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20363283A Granted JPS6097946A (ja) | 1983-11-01 | 1983-11-01 | カルボキサミド誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6097946A (US07368563-20080506-C00056.png) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5191113A (en) * | 1987-05-07 | 1993-03-02 | Ono Pharmaceutical Co., Ltd. | Cinnamoylamide derivatives |
| JPH0562724U (ja) * | 1992-01-31 | 1993-08-20 | 株式会社大井製作所 | 回動レバーの支持構造 |
| JPH0641038A (ja) * | 1992-07-17 | 1994-02-15 | Mitsubishi Kasei Corp | カルボン酸誘導体 |
| BR9811845A (pt) * | 1997-08-05 | 2000-08-08 | American Home Prod | Análogos do ácido antranìlico |
| US6127392A (en) * | 1997-08-05 | 2000-10-03 | American Home Products Corporation | Anthranilic acid analogs |
| CN1265643A (zh) * | 1997-08-05 | 2000-09-06 | 美国家用产品公司 | 邻氨基苯甲酸类似物 |
| DE19935219A1 (de) * | 1999-07-27 | 2001-02-01 | Boehringer Ingelheim Pharma | Carbonsäureamide, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung |
| GB0319124D0 (en) * | 2003-08-14 | 2003-09-17 | Smithkline Beecham Corp | Chemical compounds |
| WO2010089984A1 (ja) * | 2009-02-03 | 2010-08-12 | 日本曹達株式会社 | フェノール性化合物および記録材料 |
| JP5549781B2 (ja) * | 2011-05-31 | 2014-07-16 | Ｄｉｃ株式会社 | 桂皮酸誘導体およびその重合体、ならびにその硬化物からなる液晶配向層 |
| US20170283445A1 (en) * | 2016-04-05 | 2017-10-05 | University Of South Carolina | Small Molecule Inhibitors Selective For Polo-Like Kinase Proteins |
| CN110357789B (zh) * | 2018-04-11 | 2022-09-30 | 华东理工大学 | 作为dhodh抑制剂的n-取代丙烯酰胺衍生物及其制备和用途 |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1077936A (en) * | 1964-09-08 | 1967-08-02 | Smith & Nephew | Substituted benzanilides |
| GB1088295A (en) * | 1965-07-10 | 1967-10-25 | Smith & Nephew | Derivatives of alkanoic acids and methods for their preparation |
| US3549689A (en) * | 1967-05-23 | 1970-12-22 | Sandoz Ag | Phenoxy-alkanoic acids |
| FR2164481A1 (en) * | 1971-12-21 | 1973-08-03 | Aries Robert | Phenylacylamino phenylalkanoic acids - antiinflammatories antipyretics analgesics and antirheumatics |
| JPS4993335A (US07368563-20080506-C00056.png) * | 1973-01-18 | 1974-09-05 | ||
| JPS50135047A (US07368563-20080506-C00056.png) * | 1974-04-16 | 1975-10-25 | ||
| JPS511439A (ja) * | 1974-04-18 | 1976-01-08 | Kissei Pharmaceutical | Hokozokuamidokarubonsan no seiho |
| JPS511440A (ja) * | 1974-04-18 | 1976-01-08 | Kissei Pharmaceutical | Shinkihokozokukarubonsanjudotai no seizohoho |
| JPS511438A (US07368563-20080506-C00056.png) * | 1974-04-18 | 1976-01-08 | Kissei Pharmaceutical | |
| JPS57106651A (en) * | 1980-12-23 | 1982-07-02 | Ono Pharmaceut Co Ltd | 1,4-disubstituted benzene compound, its preparation, and inhibitor against leukotriene biosynthesis comprising it as active ingredient |
-
1983
- 1983-11-01 JP JP20363283A patent/JPS6097946A/ja active Granted
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1077936A (en) * | 1964-09-08 | 1967-08-02 | Smith & Nephew | Substituted benzanilides |
| GB1088295A (en) * | 1965-07-10 | 1967-10-25 | Smith & Nephew | Derivatives of alkanoic acids and methods for their preparation |
| US3549689A (en) * | 1967-05-23 | 1970-12-22 | Sandoz Ag | Phenoxy-alkanoic acids |
| FR2164481A1 (en) * | 1971-12-21 | 1973-08-03 | Aries Robert | Phenylacylamino phenylalkanoic acids - antiinflammatories antipyretics analgesics and antirheumatics |
| JPS4993335A (US07368563-20080506-C00056.png) * | 1973-01-18 | 1974-09-05 | ||
| JPS50135047A (US07368563-20080506-C00056.png) * | 1974-04-16 | 1975-10-25 | ||
| JPS511439A (ja) * | 1974-04-18 | 1976-01-08 | Kissei Pharmaceutical | Hokozokuamidokarubonsan no seiho |
| JPS511440A (ja) * | 1974-04-18 | 1976-01-08 | Kissei Pharmaceutical | Shinkihokozokukarubonsanjudotai no seizohoho |
| JPS511438A (US07368563-20080506-C00056.png) * | 1974-04-18 | 1976-01-08 | Kissei Pharmaceutical | |
| JPS57106651A (en) * | 1980-12-23 | 1982-07-02 | Ono Pharmaceut Co Ltd | 1,4-disubstituted benzene compound, its preparation, and inhibitor against leukotriene biosynthesis comprising it as active ingredient |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6097946A (ja) | 1985-05-31 |
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