JPH0146512B2 - - Google Patents
Info
- Publication number
- JPH0146512B2 JPH0146512B2 JP59147042A JP14704284A JPH0146512B2 JP H0146512 B2 JPH0146512 B2 JP H0146512B2 JP 59147042 A JP59147042 A JP 59147042A JP 14704284 A JP14704284 A JP 14704284A JP H0146512 B2 JPH0146512 B2 JP H0146512B2
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- fluoro
- quinoline
- dihydro
- 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
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- RNFVYNHWISDANK-UHFFFAOYSA-N 6-fluoro-1-(4-methoxyphenyl)-7-(1-methylpiperazin-2-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=CC=C(C=C1)N1C=C(C(C2=CC(=C(C=C12)C1N(CCNC1)C)F)=O)C(=O)O RNFVYNHWISDANK-UHFFFAOYSA-N 0.000 description 27
- 239000002253 acid Substances 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- -1 (substituted) phenyl group Chemical group 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 18
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- JQRIKWHVMIRRIC-UHFFFAOYSA-N 7-chloro-6-fluoro-1-(4-methoxyphenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1C2=CC(Cl)=C(F)C=C2C(=O)C(C(O)=O)=C1 JQRIKWHVMIRRIC-UHFFFAOYSA-N 0.000 description 14
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 7
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 5
- LNDZQOCPDSKPRL-UHFFFAOYSA-N 6-fluoro-4-oxo-1-phenyl-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=CC=C1 LNDZQOCPDSKPRL-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- FAKJFAMIABOKBW-UHFFFAOYSA-N 1-(2,4-dichloro-5-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC(F)=C(Cl)C=C1Cl FAKJFAMIABOKBW-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JSLUSQSYDLPXHJ-UHFFFAOYSA-N 6-fluoro-1-(4-fluorophenyl)-7-[3-(methylamino)pyrrolidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(NC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1 JSLUSQSYDLPXHJ-UHFFFAOYSA-N 0.000 description 3
- FBAMWRYINJFGPJ-UHFFFAOYSA-N 7-chloro-6-fluoro-1-(4-fluorophenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 FBAMWRYINJFGPJ-UHFFFAOYSA-N 0.000 description 3
- ZPDINCURCCHBQE-UHFFFAOYSA-N 7-chloro-6-fluoro-4-oxo-1-phenylquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=CC=C1 ZPDINCURCCHBQE-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 125000004193 piperazinyl group Chemical group 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- XBHBWNFJWIASRO-UHFFFAOYSA-N 6-fluoro-1-(4-fluorophenyl)-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 XBHBWNFJWIASRO-UHFFFAOYSA-N 0.000 description 2
- PVEJGMQLRSFBKT-UHFFFAOYSA-N 6-fluoro-1-(4-fluorophenyl)-4-oxo-7-thiomorpholin-4-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCSCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 PVEJGMQLRSFBKT-UHFFFAOYSA-N 0.000 description 2
- VBYVJSSJBFHEEU-UHFFFAOYSA-N 6-fluoro-1-(4-fluorophenyl)-7-morpholin-4-yl-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCOCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 VBYVJSSJBFHEEU-UHFFFAOYSA-N 0.000 description 2
- ODPMCMZVMWSRDZ-UHFFFAOYSA-N 6-fluoro-1-(4-hydroxyphenyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(O)C=C1 ODPMCMZVMWSRDZ-UHFFFAOYSA-N 0.000 description 2
- NWIWVTIRFXWVKH-UHFFFAOYSA-N 6-fluoro-1-(4-methoxyphenyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1C2=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(O)=O)=C1 NWIWVTIRFXWVKH-UHFFFAOYSA-N 0.000 description 2
- QEFDSJQBPGAMEG-UHFFFAOYSA-N 6-fluoro-1-(4-methylphenyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1N1C2=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(O)=O)=C1 QEFDSJQBPGAMEG-UHFFFAOYSA-N 0.000 description 2
- LHDJHAUXLFWFHX-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-6-fluoro-1-(4-fluorophenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1 LHDJHAUXLFWFHX-UHFFFAOYSA-N 0.000 description 2
- RKTHURGQCPDPBA-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-6-fluoro-4-oxo-1-phenylquinoline-3-carboxylic acid Chemical compound C1C(N)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1=CC=CC=C1 RKTHURGQCPDPBA-UHFFFAOYSA-N 0.000 description 2
- OSLNLORLIWUNRI-UHFFFAOYSA-N 7-[3-(dimethylamino)pyrrolidin-1-yl]-6-fluoro-1-(4-fluorophenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N(C)C)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1 OSLNLORLIWUNRI-UHFFFAOYSA-N 0.000 description 2
- WJISURFRPUDUEE-UHFFFAOYSA-N 7-chloro-6-fluoro-1-(4-hydroxyphenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(O)C=C1 WJISURFRPUDUEE-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000194017 Streptococcus Species 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 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
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 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
- AVAWMINJNRAQFS-UHFFFAOYSA-N n,n-dimethylpyrrolidin-3-amine Chemical compound CN(C)C1CCNC1 AVAWMINJNRAQFS-UHFFFAOYSA-N 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007909 solid dosage form Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-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
- 125000004178 (C1-C4) alkyl group Chemical group 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
- AAMFCDRGHVWGAW-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1F AAMFCDRGHVWGAW-UHFFFAOYSA-N 0.000 description 1
- BJAIPQXHPCWFOA-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-[3-(dimethylamino)pyrrolidin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N(C)C)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1F BJAIPQXHPCWFOA-UHFFFAOYSA-N 0.000 description 1
- KZZORAQLFRLNGQ-UHFFFAOYSA-N 1-(4-bromophenyl)-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(Br)C=C1 KZZORAQLFRLNGQ-UHFFFAOYSA-N 0.000 description 1
- SXGXCNFCFOPZOW-UHFFFAOYSA-N 1-(4-chlorophenyl)-6-fluoro-4-oxo-2-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1N1C2=CC=C(F)C=C2C(=O)C(C(=O)O)=C1N1CCNCC1 SXGXCNFCFOPZOW-UHFFFAOYSA-N 0.000 description 1
- ADJYBZROBYWXRW-UHFFFAOYSA-N 1-(4-chlorophenyl)-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(Cl)C=C1 ADJYBZROBYWXRW-UHFFFAOYSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical group CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- 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 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 description 1
- GUFVLIDVTHOZEJ-UHFFFAOYSA-N 4-oxo-7-piperazin-1-yl-1h-quinoline-3-carboxylic acid Chemical class C=1C=C2C(=O)C(C(=O)O)=CNC2=CC=1N1CCNCC1 GUFVLIDVTHOZEJ-UHFFFAOYSA-N 0.000 description 1
- SVOCSSPPJITSSN-UHFFFAOYSA-N 6-fluoro-1-(2-fluorophenyl)-4-oxo-2-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C=1C=CC=C(F)C=1N1C2=CC=C(F)C=C2C(=O)C(C(=O)O)=C1N1CCNCC1 SVOCSSPPJITSSN-UHFFFAOYSA-N 0.000 description 1
- ARZDSVFJNIANND-UHFFFAOYSA-N 6-fluoro-1-(2-fluorophenyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=CC=C1F ARZDSVFJNIANND-UHFFFAOYSA-N 0.000 description 1
- ZOZNRCBKOAEONL-UHFFFAOYSA-N 6-fluoro-1-(3-fluorophenyl)-4-oxo-2-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C=1C=CC(F)=CC=1N1C2=CC=C(F)C=C2C(=O)C(C(=O)O)=C1N1CCNCC1 ZOZNRCBKOAEONL-UHFFFAOYSA-N 0.000 description 1
- NSHVCBPBJCZADI-UHFFFAOYSA-N 6-fluoro-1-(3-fluorophenyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=CC(F)=C1 NSHVCBPBJCZADI-UHFFFAOYSA-N 0.000 description 1
- OMGCHPHZOOFRIQ-UHFFFAOYSA-N 6-fluoro-1-(4-fluorophenyl)-4-oxo-2-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C=1C=C(F)C=CC=1N1C2=CC=C(F)C=C2C(=O)C(C(=O)O)=C1N1CCNCC1 OMGCHPHZOOFRIQ-UHFFFAOYSA-N 0.000 description 1
- VQJDQQGGVLGRJN-UHFFFAOYSA-N 6-fluoro-1-(4-hydroxyphenyl)-4-oxo-2-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C=1C=C(O)C=CC=1N1C2=CC=C(F)C=C2C(=O)C(C(=O)O)=C1N1CCNCC1 VQJDQQGGVLGRJN-UHFFFAOYSA-N 0.000 description 1
- ZCUGOOOGXFPWRD-UHFFFAOYSA-N 6-fluoro-1-(4-hydroxyphenyl)-4-oxo-7-thiomorpholin-4-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCSCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(O)C=C1 ZCUGOOOGXFPWRD-UHFFFAOYSA-N 0.000 description 1
- YMLIGHBTBFCTRN-UHFFFAOYSA-N 6-fluoro-4-oxo-1-phenyl-7-thiomorpholin-4-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCSCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=CC=C1 YMLIGHBTBFCTRN-UHFFFAOYSA-N 0.000 description 1
- WDLYMRGLMZNZDF-UHFFFAOYSA-N 6-fluoro-7-morpholin-4-yl-4-oxo-1-phenylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCOCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=CC=C1 WDLYMRGLMZNZDF-UHFFFAOYSA-N 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
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- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical class C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51471683A | 1983-07-18 | 1983-07-18 | |
| US514716 | 1983-07-18 | ||
| US57422784A | 1984-01-26 | 1984-01-26 | |
| US574227 | 1984-01-26 | ||
| US597854 | 1984-04-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6056959A JPS6056959A (ja) | 1985-04-02 |
| JPH0146512B2 true JPH0146512B2 (ko) | 1989-10-09 |
Family
ID=27058300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14704284A Granted JPS6056959A (ja) | 1983-07-18 | 1984-07-17 | キノリン抗菌性化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6056959A (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL83049A (en) * | 1986-07-04 | 1991-12-12 | Chemie Linz Ag | 4-quinolinone-3-carboxylic acid derivatives,their manufacture and pharmaceutical compositions containing them |
| KR20190016962A (ko) * | 2016-06-15 | 2019-02-19 | 와쿠나가 세이야쿠 가부시키 가이샤 | 신규 피리돈카르복실산 유도체 또는 그 염 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1147336A (en) * | 1965-06-14 | 1969-04-02 | Lilly Industries Ltd | Quinoline-3-carboxylic acid derivatives |
| JPS5466686A (en) * | 1977-09-20 | 1979-05-29 | Dainippon Pharmaceut Co Ltd | Quinoline-3-carboxylic acid derivative, its preparation, and pharmaceutical composition containig the same |
| JPS5777683A (en) * | 1980-09-03 | 1982-05-15 | Bayer Ag | 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro- naphthyridine-3-carboxylic acids or salts thereof, manufacture and antibacterial thereof as active ingredient |
-
1984
- 1984-07-17 JP JP14704284A patent/JPS6056959A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1147336A (en) * | 1965-06-14 | 1969-04-02 | Lilly Industries Ltd | Quinoline-3-carboxylic acid derivatives |
| JPS5466686A (en) * | 1977-09-20 | 1979-05-29 | Dainippon Pharmaceut Co Ltd | Quinoline-3-carboxylic acid derivative, its preparation, and pharmaceutical composition containig the same |
| JPS5777683A (en) * | 1980-09-03 | 1982-05-15 | Bayer Ag | 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro- naphthyridine-3-carboxylic acids or salts thereof, manufacture and antibacterial thereof as active ingredient |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6056959A (ja) | 1985-04-02 |
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| JPH0780876B2 (ja) | １‐シクロプロピル‐１，４‐ジヒドロ‐４‐オキソ‐７‐［４‐（２‐オキソ‐１，３‐ジオキソル‐４‐イル‐メチル）‐１‐ピペラジニル‐３‐キノリンカルボン酸 | |
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