JPH0114224B2 - - Google Patents
Info
- Publication number
- JPH0114224B2 JPH0114224B2 JP55039610A JP3961080A JPH0114224B2 JP H0114224 B2 JPH0114224 B2 JP H0114224B2 JP 55039610 A JP55039610 A JP 55039610A JP 3961080 A JP3961080 A JP 3961080A JP H0114224 B2 JPH0114224 B2 JP H0114224B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- quinolone
- hydrogen
- melting point
- compound
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 90
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- -1 quinolone compound Chemical class 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000001475 halogen functional group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- UYGONJYYUKVHDD-UHFFFAOYSA-N flosequinan Chemical compound C1=C(F)C=C2N(C)C=C(S(C)=O)C(=O)C2=C1 UYGONJYYUKVHDD-UHFFFAOYSA-N 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 113
- 238000002844 melting Methods 0.000 description 93
- 230000008018 melting Effects 0.000 description 93
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 150000007660 quinolones Chemical class 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 230000003647 oxidation Effects 0.000 description 13
- 238000007254 oxidation reaction Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 230000036772 blood pressure Effects 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- 239000003826 tablet Substances 0.000 description 11
- 241000700159 Rattus Species 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 239000002775 capsule Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000012265 solid product Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- 230000011987 methylation Effects 0.000 description 4
- 238000007069 methylation reaction Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000003462 sulfoxides Chemical class 0.000 description 4
- GEMDGXXVKPNXOV-UHFFFAOYSA-N 7-bromo-3-methylsulfinyl-3h-quinolin-4-one Chemical compound BrC1=CC=C2C(=O)C(S(=O)C)C=NC2=C1 GEMDGXXVKPNXOV-UHFFFAOYSA-N 0.000 description 3
- GZQHWCULMKQPMV-UHFFFAOYSA-N 7-chloro-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound C1=C(Cl)C=C2N(C)C=C(S(C)=O)C(=O)C2=C1 GZQHWCULMKQPMV-UHFFFAOYSA-N 0.000 description 3
- ZGFPFJNYSUVWHB-UHFFFAOYSA-N 7-fluoro-3-methylsulfinyl-3h-quinolin-4-one Chemical compound FC1=CC=C2C(=O)C(S(=O)C)C=NC2=C1 ZGFPFJNYSUVWHB-UHFFFAOYSA-N 0.000 description 3
- LIHRHGSHVXLIOB-UHFFFAOYSA-N 7-tert-butyl-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound C1=C(C(C)(C)C)C=C2N(C)C=C(S(C)=O)C(=O)C2=C1 LIHRHGSHVXLIOB-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
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 150000005130 benzoxazines Chemical class 0.000 description 3
- 239000001506 calcium phosphate Substances 0.000 description 3
- 229910000389 calcium phosphate Inorganic materials 0.000 description 3
- 235000011010 calcium phosphates Nutrition 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 3
- AKNVDMJCVKFYSB-UHFFFAOYSA-N 1-methyl-3-methylsulfanyl-7-propan-2-ylquinolin-4-one Chemical compound CC(C)C1=CC=C2C(=O)C(SC)=CN(C)C2=C1 AKNVDMJCVKFYSB-UHFFFAOYSA-N 0.000 description 2
- FCLWUYJURISLKH-UHFFFAOYSA-N 1-methyl-3-methylsulfinyl-7-(trifluoromethyl)quinolin-4-one Chemical compound C1=C(C(F)(F)F)C=C2N(C)C=C(S(C)=O)C(=O)C2=C1 FCLWUYJURISLKH-UHFFFAOYSA-N 0.000 description 2
- SEUSIPHENXRHAC-UHFFFAOYSA-N 2-methyl-3h-quinoline-4-thione Chemical compound C1=CC=C2C(=S)CC(C)=NC2=C1 SEUSIPHENXRHAC-UHFFFAOYSA-N 0.000 description 2
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 2
- BGDOLELXXPTPFX-UHFFFAOYSA-N 3,4-dihydro-2h-1,2-benzoxazine Chemical class C1=CC=C2ONCCC2=C1 BGDOLELXXPTPFX-UHFFFAOYSA-N 0.000 description 2
- QQXIGVYUZQSHNK-UHFFFAOYSA-N 3-butylsulfanyl-1-methylquinolin-4-one Chemical compound C1=CC=C2C(=O)C(SCCCC)=CN(C)C2=C1 QQXIGVYUZQSHNK-UHFFFAOYSA-N 0.000 description 2
- SCWPCJKOXRPFCD-UHFFFAOYSA-N 3-ethylsulfanyl-1-methylquinolin-4-one Chemical compound C1=CC=C2C(=O)C(SCC)=CN(C)C2=C1 SCWPCJKOXRPFCD-UHFFFAOYSA-N 0.000 description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
- BACOFPPVBVJWHF-UHFFFAOYSA-N 6,7-dimethoxy-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C1C=C(OC)C(OC)=C2 BACOFPPVBVJWHF-UHFFFAOYSA-N 0.000 description 2
- KUFYVZBJMBNICU-UHFFFAOYSA-N 7-chloro-6-methoxy-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C1C=C(Cl)C(OC)=C2 KUFYVZBJMBNICU-UHFFFAOYSA-N 0.000 description 2
- ZKTQPDBLGNGCBO-UHFFFAOYSA-N 7-ethyl-1,3-dimethylquinoline-4-thione Chemical compound CN1C=C(C)C(=S)C=2C1=CC(CC)=CC=2 ZKTQPDBLGNGCBO-UHFFFAOYSA-N 0.000 description 2
- CKQUAMJNMYKHBP-UHFFFAOYSA-N 7-fluoro-6-methoxy-1,3-dimethylquinoline-4-thione Chemical compound CN1C=C(C)C(=S)C2=C1C=C(F)C(OC)=C2 CKQUAMJNMYKHBP-UHFFFAOYSA-N 0.000 description 2
- ZCTAXXJVBDEDEK-UHFFFAOYSA-N 7-methoxy-1,3-dimethylquinoline-4-thione Chemical compound CN1C=C(C)C(=S)C=2C1=CC(OC)=CC=2 ZCTAXXJVBDEDEK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 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 2
- 235000019759 Maize starch Nutrition 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000002702 enteric coating Substances 0.000 description 2
- 238000009505 enteric coating Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 150000004967 organic peroxy acids Chemical class 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- SEYHGPJTLNZDRF-UHFFFAOYSA-N 1,3,5,6-tetramethylquinoline-4-thione Chemical compound CN1C=C(C)C(=S)C2=C(C)C(C)=CC=C21 SEYHGPJTLNZDRF-UHFFFAOYSA-N 0.000 description 1
- GTCKDDFNAUGPSX-UHFFFAOYSA-N 1,3,5,7-tetramethylquinoline-4-thione Chemical compound CN1C=C(C)C(=S)C=2C1=CC(C)=CC=2C GTCKDDFNAUGPSX-UHFFFAOYSA-N 0.000 description 1
- PISQUBRUAURAFJ-UHFFFAOYSA-N 1,3,6,7-tetramethylquinoline-4-thione Chemical compound CN1C=C(C)C(=S)C2=C1C=C(C)C(C)=C2 PISQUBRUAURAFJ-UHFFFAOYSA-N 0.000 description 1
- PEOBPJSNIMNPPY-UHFFFAOYSA-N 1,5,6-trimethyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C(C)C(C)=CC=C21 PEOBPJSNIMNPPY-UHFFFAOYSA-N 0.000 description 1
- HAZYXTYCLOYJIL-UHFFFAOYSA-N 1,5,7-trimethyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C=2C1=CC(C)=CC=2C HAZYXTYCLOYJIL-UHFFFAOYSA-N 0.000 description 1
- XDRVLQHWGPQSCN-UHFFFAOYSA-N 1,6-dimethyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=CC(C)=CC=C21 XDRVLQHWGPQSCN-UHFFFAOYSA-N 0.000 description 1
- ZXNFYHLFPXEBGY-UHFFFAOYSA-N 1,7-dimethyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C=2C1=CC(C)=CC=2 ZXNFYHLFPXEBGY-UHFFFAOYSA-N 0.000 description 1
- FCSWOQDHAURNPI-UHFFFAOYSA-N 1,7-dimethyl-3-methylsulfinylquinoline-4-thione Chemical compound CN1C=C(S(C)=O)C(=S)C=2C1=CC(C)=CC=2 FCSWOQDHAURNPI-UHFFFAOYSA-N 0.000 description 1
- VHBJGBWEWWARRW-UHFFFAOYSA-N 1,8-dimethyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C1C(C)=CC=C2 VHBJGBWEWWARRW-UHFFFAOYSA-N 0.000 description 1
- UAUPCSQPVYZSPA-UHFFFAOYSA-N 1-(1,3-dimethyl-4-sulfanylidenequinolin-6-yl)ethanone Chemical compound CN1C=C(C)C(=S)C2=CC(C(=O)C)=CC=C21 UAUPCSQPVYZSPA-UHFFFAOYSA-N 0.000 description 1
- SQENVUCMPYZOOM-UHFFFAOYSA-N 1-(1,3-dimethyl-4-sulfanylidenequinolin-7-yl)ethanone Chemical compound CN1C=C(C)C(=S)C=2C1=CC(C(=O)C)=CC=2 SQENVUCMPYZOOM-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- KCGIHQJVXLDUKZ-UHFFFAOYSA-N 1-butyl-3-methylsulfinylquinolin-4-one Chemical compound C1=CC=C2N(CCCC)C=C(S(C)=O)C(=O)C2=C1 KCGIHQJVXLDUKZ-UHFFFAOYSA-N 0.000 description 1
- YVJLDIJYCATDIW-UHFFFAOYSA-N 1-methyl-3,5-bis(methylsulfanyl)quinolin-4-one Chemical compound CN1C=C(SC)C(=O)C2=C1C=CC=C2SC YVJLDIJYCATDIW-UHFFFAOYSA-N 0.000 description 1
- XMOJSVXQECHJNT-UHFFFAOYSA-N 1-methyl-3,7-bis(methylsulfanyl)quinolin-4-one Chemical compound CN1C=C(SC)C(=O)C=2C1=CC(SC)=CC=2 XMOJSVXQECHJNT-UHFFFAOYSA-N 0.000 description 1
- WCBHMVXDXAVQMP-UHFFFAOYSA-N 1-methyl-3-methylsulfanyl-7-(trifluoromethyl)quinolin-4-one Chemical compound FC(F)(F)C1=CC=C2C(=O)C(SC)=CN(C)C2=C1 WCBHMVXDXAVQMP-UHFFFAOYSA-N 0.000 description 1
- ROFXSPPJVBQRMK-UHFFFAOYSA-N 1-methyl-3-methylsulfinyl-7-propan-2-ylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C=2C1=CC(C(C)C)=CC=2 ROFXSPPJVBQRMK-UHFFFAOYSA-N 0.000 description 1
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- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000004916 vomit Anatomy 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D215/36—Sulfur atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7910558 | 1979-03-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55130960A JPS55130960A (en) | 1980-10-11 |
| JPH0114224B2 true JPH0114224B2 (no) | 1989-03-10 |
Family
ID=10504143
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3961080A Granted JPS55130960A (en) | 1979-03-27 | 1980-03-27 | Quinolone compound |
| JP61316048A Granted JPS62215526A (ja) | 1979-03-27 | 1986-12-24 | 降圧剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61316048A Granted JPS62215526A (ja) | 1979-03-27 | 1986-12-24 | 降圧剤 |
Country Status (10)
| Country | Link |
|---|---|
| JP (2) | JPS55130960A (no) |
| BE (1) | BE882443A (no) |
| CY (1) | CY1343A (no) |
| ES (1) | ES8104232A1 (no) |
| GB (1) | GB2047691B (no) |
| GE (1) | GEP19970835B (no) |
| JO (1) | JO1072B1 (no) |
| MX (1) | MX5950A (no) |
| SU (1) | SU1124886A3 (no) |
| ZA (1) | ZA801575B (no) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA801575B (en) * | 1979-03-27 | 1981-03-25 | Boots Co Ltd | Therapeutic agents |
| IE51542B1 (en) * | 1980-09-26 | 1987-01-07 | Boots Co Ltd | Therapeutic agents |
| EP0343574B1 (en) * | 1988-05-24 | 1994-07-27 | Kirin Beer Kabushiki Kaisha | 4(1H)-quinolone derivatives |
| US8697674B2 (en) * | 2004-12-29 | 2014-04-15 | Naturon, Inc. | Xanthurenic acid derivative pharmaceutical compositions and methods related thereto |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA801575B (en) * | 1979-03-27 | 1981-03-25 | Boots Co Ltd | Therapeutic agents |
-
1980
- 1980-03-18 ZA ZA00801575A patent/ZA801575B/xx unknown
- 1980-03-25 GB GB8010075A patent/GB2047691B/en not_active Expired
- 1980-03-25 CY CY1343A patent/CY1343A/xx unknown
- 1980-03-26 BE BE0/199956A patent/BE882443A/fr not_active IP Right Cessation
- 1980-03-26 ES ES489929A patent/ES8104232A1/es not_active Expired
- 1980-03-26 JO JO19801072A patent/JO1072B1/en active
- 1980-03-27 JP JP3961080A patent/JPS55130960A/ja active Granted
-
1981
- 1981-01-19 SU SU802897803A patent/SU1124886A3/ru active
-
1985
- 1985-01-09 MX MX595085A patent/MX5950A/es unknown
-
1986
- 1986-12-24 JP JP61316048A patent/JPS62215526A/ja active Granted
-
1994
- 1994-09-07 GE GEAP19942162A patent/GEP19970835B/en unknown
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL ABSTRACTS * |
| CHIM THER=1973 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MX5950A (es) | 1993-11-01 |
| ES489929A0 (es) | 1981-04-16 |
| GEP19970835B (en) | 1997-02-10 |
| GB2047691B (en) | 1983-07-20 |
| JO1072B1 (en) | 1982-07-10 |
| ZA801575B (en) | 1981-03-25 |
| GB2047691A (en) | 1980-12-03 |
| CY1343A (en) | 1987-01-16 |
| SU1124886A3 (ru) | 1984-11-15 |
| BE882443A (fr) | 1980-09-26 |
| JPH0250086B2 (no) | 1990-11-01 |
| ES8104232A1 (es) | 1981-04-16 |
| JPS62215526A (ja) | 1987-09-22 |
| JPS55130960A (en) | 1980-10-11 |
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