JPH0568466B2 - - Google Patents
Info
- Publication number
- JPH0568466B2 JPH0568466B2 JP8511122A JP1112285A JPH0568466B2 JP H0568466 B2 JPH0568466 B2 JP H0568466B2 JP 8511122 A JP8511122 A JP 8511122A JP 1112285 A JP1112285 A JP 1112285A JP H0568466 B2 JPH0568466 B2 JP H0568466B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- formula
- oxo
- quinoline
- carboxylic acid
- 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 40
- -1 hydroxy-substituted phenyl group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 23
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 22
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
- IFNWESYYDINUHV-UHFFFAOYSA-N 2,6-dimethylpiperazine Chemical compound CC1CNCC(C)N1 IFNWESYYDINUHV-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 4
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-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
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- KWDVJYLIAJHEOW-UHFFFAOYSA-N ethyl 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propanoate Chemical compound CCOC(=O)CC(=O)C1=CC(F)=C(F)C(F)=C1F KWDVJYLIAJHEOW-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- HDCCJUCOIKLZNM-UHFFFAOYSA-N n-pyrrolidin-3-ylacetamide Chemical compound CC(=O)NC1CCNC1 HDCCJUCOIKLZNM-UHFFFAOYSA-N 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 150000003248 quinolines Chemical class 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical group CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 description 2
- SNZSGXYIECMAGY-UHFFFAOYSA-N 5-(4-fluorophenyl)-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid Chemical compound C12=CC=3OCOC=3C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 SNZSGXYIECMAGY-UHFFFAOYSA-N 0.000 description 2
- GWYWORGKFDQQDR-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid Chemical compound C12=CC=3OCOC=3C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(O)C=C1 GWYWORGKFDQQDR-UHFFFAOYSA-N 0.000 description 2
- ZIVRWYNUCZNRHY-UHFFFAOYSA-N 5-(4-methoxyphenyl)-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1C2=CC(OCO3)=C3C=C2C(=O)C(C(O)=O)=C1 ZIVRWYNUCZNRHY-UHFFFAOYSA-N 0.000 description 2
- UZMFIWOHBVVVQV-UHFFFAOYSA-N 6,8-difluoro-1-(4-fluorophenyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 UZMFIWOHBVVVQV-UHFFFAOYSA-N 0.000 description 2
- WBSMYKBTVQONBQ-UHFFFAOYSA-N 6,8-difluoro-1-(4-hydroxyphenyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(O)C=C1 WBSMYKBTVQONBQ-UHFFFAOYSA-N 0.000 description 2
- BJBXYKUCVIHUPN-UHFFFAOYSA-N 6,8-difluoro-4-oxo-1-phenyl-7-pyrrolidin-1-ylquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=CC=C1 BJBXYKUCVIHUPN-UHFFFAOYSA-N 0.000 description 2
- CZRQTENFPFMNKL-UHFFFAOYSA-N 6,8-difluoro-7-(2-hydroxyethylamino)-4-oxo-1-phenylquinoline-3-carboxylic acid Chemical group FC=1C(NCCO)=C(F)C=C(C(C(C(O)=O)=C2)=O)C=1N2C1=CC=CC=C1 CZRQTENFPFMNKL-UHFFFAOYSA-N 0.000 description 2
- YDIMYCBPIFNBRM-UHFFFAOYSA-N 6,8-difluoro-7-(3-hydroxypyrrolidin-1-yl)-4-oxo-1-phenylquinoline-3-carboxylic acid Chemical compound C1C(O)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C=CC=CC=3)C2=C1F YDIMYCBPIFNBRM-UHFFFAOYSA-N 0.000 description 2
- UATOSTMTFSFXKR-UHFFFAOYSA-N 6,8-difluoro-7-hydrazinyl-4-oxo-1-phenylquinoline-3-carboxylic acid Chemical compound FC=1C(NN)=C(F)C=C(C(C(C(O)=O)=C2)=O)C=1N2C1=CC=CC=C1 UATOSTMTFSFXKR-UHFFFAOYSA-N 0.000 description 2
- MISWKBJYRUSEQI-UHFFFAOYSA-N 6,8-difluoro-7-morpholin-4-yl-4-oxo-1-phenylquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCOCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=CC=C1 MISWKBJYRUSEQI-UHFFFAOYSA-N 0.000 description 2
- PNEHWOALOQLSME-UHFFFAOYSA-N 6-fluoro-1-(4-fluorophenyl)-4-oxo-7-pyridin-4-ylquinoline-3-carboxylic acid Chemical compound C12=CC(C=3C=CN=CC=3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 PNEHWOALOQLSME-UHFFFAOYSA-N 0.000 description 2
- ZPXFWKRWHCLHDG-UHFFFAOYSA-N 6-fluoro-4-oxo-1-phenyl-7-pyridin-4-ylquinoline-3-carboxylic acid Chemical compound C12=CC(C=3C=CN=CC=3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=CC=C1 ZPXFWKRWHCLHDG-UHFFFAOYSA-N 0.000 description 2
- KNKODDVZZBFNQB-UHFFFAOYSA-N 7-(3,5-dimethylpiperazin-1-yl)-6,8-difluoro-1-(4-hydroxyphenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)NC(C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C=CC(O)=CC=3)C2=C1F KNKODDVZZBFNQB-UHFFFAOYSA-N 0.000 description 2
- ZRAOKMRKMIUHBV-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-6,8-difluoro-1-(4-hydroxyphenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C=CC(O)=CC=3)C2=C1F ZRAOKMRKMIUHBV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000007864 aqueous solution 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
- 239000002775 capsule Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 230000002458 infectious effect Effects 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007788 liquid Substances 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical group COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007909 solid dosage form Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
- DTYLXDLAOLOTKT-UHFFFAOYSA-N 1,4-dihydroquinoline-3-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)=CNC2=C1 DTYLXDLAOLOTKT-UHFFFAOYSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical class CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- SFKRXQKJTIYUAG-UHFFFAOYSA-N 2,3,4,5-tetrafluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C(F)=C1F SFKRXQKJTIYUAG-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical group NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- GUFVLIDVTHOZEJ-UHFFFAOYSA-N 4-oxo-7-piperazin-1-yl-1h-quinoline-3-carboxylic acid Chemical group C=1C=C2C(=O)C(C(=O)O)=CNC2=CC=1N1CCNCC1 GUFVLIDVTHOZEJ-UHFFFAOYSA-N 0.000 description 1
- NSRDBSTUJJKANY-UHFFFAOYSA-N 6,7,8-trifluoro-1-(4-fluorophenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 NSRDBSTUJJKANY-UHFFFAOYSA-N 0.000 description 1
- AZPOPHWZZLZNJB-UHFFFAOYSA-N 6,7,8-trifluoro-4-oxo-1-phenylquinoline-3-carboxylic acid Chemical compound C12=C(F)C(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=CC=C1 AZPOPHWZZLZNJB-UHFFFAOYSA-N 0.000 description 1
- DFIMGEUWHILFCF-UHFFFAOYSA-N 6,8-difluoro-1-(4-fluorophenyl)-4-oxo-7-piperidin-1-ylquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCCCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 DFIMGEUWHILFCF-UHFFFAOYSA-N 0.000 description 1
- HCEABVJPPQSYTI-UHFFFAOYSA-N 6,8-difluoro-1-(4-fluorophenyl)-4-oxo-7-pyrrolidin-1-ylquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 HCEABVJPPQSYTI-UHFFFAOYSA-N 0.000 description 1
- KLKHDURINXBXNN-UHFFFAOYSA-N 6,8-difluoro-1-(4-fluorophenyl)-7-(3-hydroxypyrrolidin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(O)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C=CC(F)=CC=3)C2=C1F KLKHDURINXBXNN-UHFFFAOYSA-N 0.000 description 1
- YAYGJMVQQPDFOW-UHFFFAOYSA-N 6,8-difluoro-1-(4-fluorophenyl)-7-morpholin-4-yl-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCOCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 YAYGJMVQQPDFOW-UHFFFAOYSA-N 0.000 description 1
- HMLHICCPIUHQIK-UHFFFAOYSA-N 6,8-difluoro-1-(4-hydroxyphenyl)-4-oxo-7-piperidin-1-ylquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCCCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(O)C=C1 HMLHICCPIUHQIK-UHFFFAOYSA-N 0.000 description 1
- JVACMVCHDLEBIP-UHFFFAOYSA-N 6,8-difluoro-1-(4-hydroxyphenyl)-7-(3-hydroxypyrrolidin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(O)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C=CC(O)=CC=3)C2=C1F JVACMVCHDLEBIP-UHFFFAOYSA-N 0.000 description 1
- ZZFGRSLBKNLDPF-UHFFFAOYSA-N 6,8-difluoro-4-oxo-1-phenyl-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=CC=C1 ZZFGRSLBKNLDPF-UHFFFAOYSA-N 0.000 description 1
- MOFNSPNUBJRLNH-UHFFFAOYSA-N 6,8-difluoro-4-oxo-1-phenyl-7-piperidin-1-ylquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCCCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=CC=C1 MOFNSPNUBJRLNH-UHFFFAOYSA-N 0.000 description 1
- NLCHCTYJNASGGK-UHFFFAOYSA-N 6-fluoro-1-(4-methoxyphenyl)-4-oxo-7-pyridin-4-ylquinoline-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1C2=CC(C=3C=CN=CC=3)=C(F)C=C2C(=O)C(C(O)=O)=C1 NLCHCTYJNASGGK-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US574225 | 1975-05-05 | ||
| US57411984A | 1984-01-26 | 1984-01-26 | |
| US574119 | 1984-01-26 | ||
| US574224 | 1984-01-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60163866A JPS60163866A (ja) | 1985-08-26 |
| JPH0568466B2 true JPH0568466B2 (xx) | 1993-09-29 |
Family
ID=24294778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1112285A Granted JPS60163866A (ja) | 1984-01-26 | 1985-01-25 | キノリン系抗菌性化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60163866A (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61251667A (ja) * | 1985-04-30 | 1986-11-08 | Otsuka Pharmaceut Co Ltd | ベンゾヘテロ環化合物 |
| ATE247089T1 (de) * | 1996-11-28 | 2003-08-15 | Wakunaga Pharma Co Ltd | Pyridoncarbonsäurederivate oder ihre salze und diese als aktive bestandteile enthaltende medikamente |
-
1985
- 1985-01-25 JP JP1112285A patent/JPS60163866A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60163866A (ja) | 1985-08-26 |
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