JPH0227329B2 - - Google Patents
Info
- Publication number
- JPH0227329B2 JPH0227329B2 JP55038837A JP3883780A JPH0227329B2 JP H0227329 B2 JPH0227329 B2 JP H0227329B2 JP 55038837 A JP55038837 A JP 55038837A JP 3883780 A JP3883780 A JP 3883780A JP H0227329 B2 JPH0227329 B2 JP H0227329B2
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- amino
- quinolinecarboxylate
- compound
- methoxy
- 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
- -1 2-ethoxyphenyl Chemical group 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 76
- 230000027119 gastric acid secretion Effects 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 230000028327 secretion Effects 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- LTPVJDPFDLGLRT-UHFFFAOYSA-N ethyl 8-ethoxy-4-(2-methoxyanilino)quinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C(OCC)=CC=CC2=C1NC1=CC=CC=C1OC LTPVJDPFDLGLRT-UHFFFAOYSA-N 0.000 claims description 2
- NXUSNIUACDUXQM-UHFFFAOYSA-N ethyl 8-methoxy-4-(2-methoxyanilino)-5-methylquinoline-3-carboxylate;dihydrochloride Chemical compound Cl.Cl.CCOC(=O)C1=CN=C2C(OC)=CC=C(C)C2=C1NC1=CC=CC=C1OC NXUSNIUACDUXQM-UHFFFAOYSA-N 0.000 claims description 2
- CRJUJZNGVQRIJL-UHFFFAOYSA-N ethyl 8-methoxy-4-(2-methylanilino)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1C CRJUJZNGVQRIJL-UHFFFAOYSA-N 0.000 claims description 2
- DXCCJYWRCAJAGW-UHFFFAOYSA-N ethyl 8-methoxy-4-(2-methylanilino)quinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1C DXCCJYWRCAJAGW-UHFFFAOYSA-N 0.000 claims description 2
- WTSHTUPDVKVIMP-UHFFFAOYSA-N ethyl 8-methoxy-4-[2-(trifluoromethyl)anilino]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1C(F)(F)F WTSHTUPDVKVIMP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims 29
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 4
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims 1
- IJJNSCKCJMFURY-UHFFFAOYSA-N ethyl 4-(2,6-dichloroanilino)-8-methoxyquinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=C(Cl)C=CC=C1Cl IJJNSCKCJMFURY-UHFFFAOYSA-N 0.000 claims 1
- RPVDYDOFURVOTB-UHFFFAOYSA-N ethyl 4-(2-ethylanilino)-8-methoxyquinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1CC RPVDYDOFURVOTB-UHFFFAOYSA-N 0.000 claims 1
- PRKZRASUCFJROT-UHFFFAOYSA-N ethyl 4-(2-methylsulfanylanilino)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C=CC=CC2=C1NC1=CC=CC=C1SC PRKZRASUCFJROT-UHFFFAOYSA-N 0.000 claims 1
- RARVHEZYDGPABL-UHFFFAOYSA-N ethyl 4-(2-methylsulfanylanilino)quinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C=CC=CC2=C1NC1=CC=CC=C1SC RARVHEZYDGPABL-UHFFFAOYSA-N 0.000 claims 1
- ASMBUJKAYWWTFO-UHFFFAOYSA-N ethyl 8-ethoxy-4-(2-methoxyanilino)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OCC)=CC=CC2=C1NC1=CC=CC=C1OC ASMBUJKAYWWTFO-UHFFFAOYSA-N 0.000 claims 1
- CNMNSQIDRWUQCU-UHFFFAOYSA-N ethyl 8-ethoxy-4-(2-methylanilino)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OCC)=CC=CC2=C1NC1=CC=CC=C1C CNMNSQIDRWUQCU-UHFFFAOYSA-N 0.000 claims 1
- PIZUEXPYKUOJJJ-UHFFFAOYSA-N ethyl 8-ethoxy-4-(2-methylanilino)quinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C(OCC)=CC=CC2=C1NC1=CC=CC=C1C PIZUEXPYKUOJJJ-UHFFFAOYSA-N 0.000 claims 1
- KFLMZCBVKCTUIR-UHFFFAOYSA-N ethyl 8-methoxy-4-(2-methoxyanilino)-5-methylquinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OC)=CC=C(C)C2=C1NC1=CC=CC=C1OC KFLMZCBVKCTUIR-UHFFFAOYSA-N 0.000 claims 1
- KRIDZTDGIKDFGO-UHFFFAOYSA-N ethyl 8-methoxy-4-(2-methoxyanilino)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1OC KRIDZTDGIKDFGO-UHFFFAOYSA-N 0.000 claims 1
- GWABEZHJVSPHNE-UHFFFAOYSA-N ethyl 8-methoxy-4-(2-methoxyanilino)quinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1OC GWABEZHJVSPHNE-UHFFFAOYSA-N 0.000 claims 1
- SSIABRIIJOPUTM-UHFFFAOYSA-N ethyl 8-methoxy-4-(2-methylsulfanylanilino)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1SC SSIABRIIJOPUTM-UHFFFAOYSA-N 0.000 claims 1
- LOPISVUVHAYYRS-UHFFFAOYSA-N ethyl 8-methoxy-4-(2-methylsulfanylanilino)quinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1SC LOPISVUVHAYYRS-UHFFFAOYSA-N 0.000 claims 1
- MYINBRFPVSYSLM-UHFFFAOYSA-N ethyl 8-methoxy-4-[2-(trifluoromethyl)anilino]quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1C(F)(F)F MYINBRFPVSYSLM-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 46
- 238000002360 preparation method Methods 0.000 description 33
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 28
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 21
- 241000700159 Rattus Species 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 210000002784 stomach Anatomy 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- UEFKMJWKPVAVND-UHFFFAOYSA-N 4-aminoquinoline-3-carboxylic acid Chemical class C1=CC=C2C(N)=C(C(O)=O)C=NC2=C1 UEFKMJWKPVAVND-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 208000008469 Peptic Ulcer Diseases 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- DWXQUAHMZWZXHP-UHFFFAOYSA-N ethyl 4-chloroquinoline-3-carboxylate Chemical compound C1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 DWXQUAHMZWZXHP-UHFFFAOYSA-N 0.000 description 7
- 229960001340 histamine Drugs 0.000 description 7
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 7
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WBRPQQSADOCKCH-UHFFFAOYSA-N 2-methylsulfanylaniline Chemical compound CSC1=CC=CC=C1N WBRPQQSADOCKCH-UHFFFAOYSA-N 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 208000025865 Ulcer Diseases 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- 108010012944 Tetragastrin Proteins 0.000 description 5
- 210000001198 duodenum Anatomy 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RGYLYUZOGHTBRF-BIHRQFPBSA-N tetragastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C2=CC=CC=C2NC=1)CCSC)C(N)=O)C1=CC=CC=C1 RGYLYUZOGHTBRF-BIHRQFPBSA-N 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 4
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000000692 Student's t-test Methods 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 238000007619 statistical method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 235000010407 ammonium alginate Nutrition 0.000 description 3
- 239000000728 ammonium alginate Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000001647 drug administration Methods 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- BBOZDELEERNECG-UHFFFAOYSA-N ethyl 4-chloro-8-methoxyquinoline-3-carboxylate Chemical compound COC1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 BBOZDELEERNECG-UHFFFAOYSA-N 0.000 description 3
- VWVPBLLIVVAAPY-UHFFFAOYSA-N ethyl 4-chloro-8-phenylquinoline-3-carboxylate Chemical compound C=1C=CC2=C(Cl)C(C(=O)OCC)=CN=C2C=1C1=CC=CC=C1 VWVPBLLIVVAAPY-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 229960002329 methacholine Drugs 0.000 description 3
- NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 208000011906 peptic ulcer disease Diseases 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000013223 sprague-dawley female rat Methods 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- 230000036269 ulceration Effects 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 2
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 2
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 2
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- OLACLXKBINPWKR-UHFFFAOYSA-N 3-(dimethylamino)propyl 8-methoxy-4-(2-methylanilino)quinoline-3-carboxylate Chemical compound CN(C)CCCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1C OLACLXKBINPWKR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 208000007107 Stomach Ulcer Diseases 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- DIOLOCSXUMYFJN-UHFFFAOYSA-N calcium;azane Chemical compound N.[Ca+2] DIOLOCSXUMYFJN-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical class CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 210000003238 esophagus Anatomy 0.000 description 2
- HINLPSGAVZPTIW-UHFFFAOYSA-N ethyl 4,8-dichloroquinoline-3-carboxylate Chemical compound ClC1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 HINLPSGAVZPTIW-UHFFFAOYSA-N 0.000 description 2
- QURGQUFEJWWDRF-UHFFFAOYSA-N ethyl 4-chloro-6-methoxyquinoline-3-carboxylate Chemical compound C1=CC(OC)=CC2=C(Cl)C(C(=O)OCC)=CN=C21 QURGQUFEJWWDRF-UHFFFAOYSA-N 0.000 description 2
- MHOFAUCLSGVKOH-UHFFFAOYSA-N ethyl 4-chloro-8-cyanoquinoline-3-carboxylate Chemical compound N#CC1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 MHOFAUCLSGVKOH-UHFFFAOYSA-N 0.000 description 2
- UNMTVPUUJFYTOJ-UHFFFAOYSA-N ethyl 4-chloro-8-ethoxyquinoline-3-carboxylate Chemical compound CCOC1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 UNMTVPUUJFYTOJ-UHFFFAOYSA-N 0.000 description 2
- PGGVUZUNDXCMSS-UHFFFAOYSA-N ethyl 4-chloro-8-methylquinoline-3-carboxylate Chemical compound CC1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 PGGVUZUNDXCMSS-UHFFFAOYSA-N 0.000 description 2
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- 239000005457 ice water Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- JHPHVAVFUYTVCL-UHFFFAOYSA-M methacholine chloride Chemical compound [Cl-].C[N+](C)(C)CC(C)OC(C)=O JHPHVAVFUYTVCL-UHFFFAOYSA-M 0.000 description 1
- 229960002931 methacholine chloride Drugs 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 231100000668 minimum lethal dose Toxicity 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- KEBXGLIHHLGNJH-UHFFFAOYSA-N n-methylsulfanylaniline Chemical compound CSNC1=CC=CC=C1 KEBXGLIHHLGNJH-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000000580 secretagogue effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 210000005070 sphincter Anatomy 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2398179A | 1979-03-26 | 1979-03-26 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1250369A Division JPH02117663A (ja) | 1979-03-26 | 1989-09-26 | ４―アミノ―３―キノリンカルボン酸類およびそのエステル類 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55147222A JPS55147222A (en) | 1980-11-17 |
| JPH0227329B2 true JPH0227329B2 (enrdf_load_stackoverflow) | 1990-06-15 |
Family
ID=21818223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3883780A Granted JPS55147222A (en) | 1979-03-26 | 1980-03-26 | 44aminoo33quinolinecarboxylic acid and its ester and gastric gland secretion control and*or antiipepticculcer |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS55147222A (enrdf_load_stackoverflow) |
| KR (1) | KR840000768B1 (enrdf_load_stackoverflow) |
| BE (1) | BE882414A (enrdf_load_stackoverflow) |
| HU (1) | HU184253B (enrdf_load_stackoverflow) |
| ZA (1) | ZA801526B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8804444D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| US5215999A (en) * | 1990-03-28 | 1993-06-01 | Otsuka Pharmaceutical Co., Ltd. | Quinoline derivative and antiulcer agent containing said quinoline derivative |
| FR2862301B1 (fr) * | 2003-11-17 | 2007-12-21 | Aventis Pharma Sa | Nouveau procede de preparation de quinoleines 3-fluorees |
-
1980
- 1980-03-14 ZA ZA00801526A patent/ZA801526B/xx unknown
- 1980-03-25 HU HU80699A patent/HU184253B/hu not_active IP Right Cessation
- 1980-03-25 KR KR1019800001231A patent/KR840000768B1/ko not_active Expired
- 1980-03-25 BE BE0/199934A patent/BE882414A/fr not_active IP Right Cessation
- 1980-03-26 JP JP3883780A patent/JPS55147222A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| KR830001899A (ko) | 1983-05-19 |
| ZA801526B (en) | 1981-08-26 |
| BE882414A (fr) | 1980-07-16 |
| JPS55147222A (en) | 1980-11-17 |
| HU184253B (en) | 1984-07-30 |
| KR840000768B1 (ko) | 1984-06-08 |
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