NO840557L - Kinolonkarboksylsyrer, fremgangsmaate til deres fremstilling samt antibakterielle midler som inneholder disse - Google Patents
Kinolonkarboksylsyrer, fremgangsmaate til deres fremstilling samt antibakterielle midler som inneholder disseInfo
- Publication number
- NO840557L NO840557L NO840557A NO840557A NO840557L NO 840557 L NO840557 L NO 840557L NO 840557 A NO840557 A NO 840557A NO 840557 A NO840557 A NO 840557A NO 840557 L NO840557 L NO 840557L
- Authority
- NO
- Norway
- Prior art keywords
- oxo
- formula
- acid
- dihydro
- fluoro
- Prior art date
Links
- -1 QUINOLON CARBOXYLIC ACIDS Chemical class 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 18
- 229940088710 antibiotic agent Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 11
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 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
- ZYRCHQNKLLACTA-UHFFFAOYSA-N 7-[4-(2-chloro-2-cyanoethyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCN(CC(Cl)C#N)CC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ZYRCHQNKLLACTA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 10
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 claims 1
- 229940124350 antibacterial drug Drugs 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000000354 decomposition reaction Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 11
- MYSWGUAQZAJSOK-UHFFFAOYSA-N Ciprofloxacin Natural products C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- DIOIOSKKIYDRIQ-UHFFFAOYSA-N ciprofloxacin hydrochloride Chemical compound Cl.C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 DIOIOSKKIYDRIQ-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- JXWCOCIEGOAZOG-UHFFFAOYSA-N 1,5-dichloro-2-fluoro-4-methylbenzene Chemical compound CC1=CC(F)=C(Cl)C=C1Cl JXWCOCIEGOAZOG-UHFFFAOYSA-N 0.000 description 6
- RPZXUSJCSDQNTE-UHFFFAOYSA-N 2,4-dichloro-5-fluorobenzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=C(Cl)C=C1Cl RPZXUSJCSDQNTE-UHFFFAOYSA-N 0.000 description 6
- ISPVACVJFUIDPD-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ISPVACVJFUIDPD-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- IGSFOXNHUBLZHU-UHFFFAOYSA-N 2,4-dichloro-5-methylaniline Chemical compound CC1=CC(N)=C(Cl)C=C1Cl IGSFOXNHUBLZHU-UHFFFAOYSA-N 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- DYRSCZBWQXEMNL-UHFFFAOYSA-N diethyl 2-(2,4-dichloro-5-fluorobenzoyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)C1=CC(F)=C(Cl)C=C1Cl DYRSCZBWQXEMNL-UHFFFAOYSA-N 0.000 description 5
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- XDKNLTYKSCDBAS-UHFFFAOYSA-N benzyl 3-iodopropanoate Chemical compound ICCC(=O)OCC1=CC=CC=C1 XDKNLTYKSCDBAS-UHFFFAOYSA-N 0.000 description 4
- FGIPJRPVDXUTRY-UHFFFAOYSA-N benzyl 6-iodohexanoate Chemical compound ICCCCCC(=O)OCC1=CC=CC=C1 FGIPJRPVDXUTRY-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- POKPUCWXUHWGMX-UHFFFAOYSA-N ethyl 3-(2,4-dichloro-5-fluorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC(F)=C(Cl)C=C1Cl POKPUCWXUHWGMX-UHFFFAOYSA-N 0.000 description 4
- UYJWKMILOGUYTL-UHFFFAOYSA-N ethyl 3-(cyclopropylamino)-2-(2,4-dichloro-5-fluorobenzoyl)prop-2-enoate Chemical compound C=1C(F)=C(Cl)C=C(Cl)C=1C(=O)C(C(=O)OCC)=CNC1CC1 UYJWKMILOGUYTL-UHFFFAOYSA-N 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 229940032330 sulfuric acid Drugs 0.000 description 4
- 230000007306 turnover Effects 0.000 description 4
- DYRWTUITSIYILW-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1CNC(C)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 DYRWTUITSIYILW-UHFFFAOYSA-N 0.000 description 3
- YLICLSGVCRSWEH-UHFFFAOYSA-N 1-cyclopropyl-6-nitro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCNCC3)=C([N+]([O-])=O)C=C2C(=O)C(C(=O)O)=CN1C1CC1 YLICLSGVCRSWEH-UHFFFAOYSA-N 0.000 description 3
- PISYZMAJMMQIRQ-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=CC=C2C(=O)C(C(=O)O)=CN1C1CC1 PISYZMAJMMQIRQ-UHFFFAOYSA-N 0.000 description 3
- SSZUMRRPCBEXRX-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-nitro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C([N+]([O-])=O)C=C2C(=O)C(C(=O)O)=CN1C1CC1 SSZUMRRPCBEXRX-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- IWQJEAWVHIBCDP-UHFFFAOYSA-N 1-cyclopropyl-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCNCC3)=CC=C2C(=O)C(C(=O)O)=CN1C1CC1 IWQJEAWVHIBCDP-UHFFFAOYSA-N 0.000 description 2
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 2
- SWLHSVRCVQLMBJ-UHFFFAOYSA-N 6,7-dichloro-1-cyclopropyl-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C(Cl)C=C2C(=O)C(C(=O)O)=CN1C1CC1 SWLHSVRCVQLMBJ-UHFFFAOYSA-N 0.000 description 2
- OSHQUWATYOBFNE-UHFFFAOYSA-N 6-chloro-1-cyclopropyl-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCNCC3)=C(Cl)C=C2C(=O)C(C(=O)O)=CN1C1CC1 OSHQUWATYOBFNE-UHFFFAOYSA-N 0.000 description 2
- PMPFWQDHBICXPC-UHFFFAOYSA-N 7-[4-(2-carboxyethyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CCC(=O)O)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 PMPFWQDHBICXPC-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- GFLNVOVUQPPWBI-UHFFFAOYSA-N benzyl 6-chlorohexanoate Chemical compound ClCCCCCC(=O)OCC1=CC=CC=C1 GFLNVOVUQPPWBI-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LYOAKSDOTROZEF-UHFFFAOYSA-N ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C(=O)OCC)C(=O)C1=CC(F)=C(Cl)C=C1Cl LYOAKSDOTROZEF-UHFFFAOYSA-N 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000004885 piperazines Chemical class 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- DREPONDJUKIQLX-UHFFFAOYSA-N 1-[ethenyl(ethoxy)phosphoryl]oxyethane Chemical compound CCOP(=O)(C=C)OCC DREPONDJUKIQLX-UHFFFAOYSA-N 0.000 description 1
- HHVJADXTWCQBSJ-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-4-oxo-7-(2,3,5,6-tetramethylpiperazin-1-yl)quinoline-3-carboxylic acid Chemical compound CC1C(C)NC(C)C(C)N1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 HHVJADXTWCQBSJ-UHFFFAOYSA-N 0.000 description 1
- NKFPTYVZHKOHGR-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-4-oxo-7-(2,3,5-trimethylpiperazin-1-yl)quinoline-3-carboxylic acid Chemical compound CC1C(C)NC(C)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 NKFPTYVZHKOHGR-UHFFFAOYSA-N 0.000 description 1
- DHUGVVKLSFUYLC-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-4-oxo-7-[4-(6-oxo-6-phenylmethoxyhexyl)piperazin-1-yl]quinoline-3-carboxylic acid Chemical compound C12=CC(N3CCN(CCCCCC(=O)OCC=4C=CC=CC=4)CC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 DHUGVVKLSFUYLC-UHFFFAOYSA-N 0.000 description 1
- MQODOORPWMZDTC-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-methyl-4-(3-oxo-3-phenylmethoxypropyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound CC1CN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CCN1CCC(=O)OCC1=CC=CC=C1 MQODOORPWMZDTC-UHFFFAOYSA-N 0.000 description 1
- IEGWRGSVZCECLC-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[4-(2-methylsulfonylethyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CCS(=O)(=O)C)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 IEGWRGSVZCECLC-UHFFFAOYSA-N 0.000 description 1
- RYCNQYDMRXIAPG-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[4-(3-methoxy-3-oxopropyl)-3,5-dimethylpiperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)N(CCC(=O)OC)C(C)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 RYCNQYDMRXIAPG-UHFFFAOYSA-N 0.000 description 1
- PHSWFJDDPGGNGP-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[4-(3-methoxy-3-oxopropyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CCC(=O)OC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 PHSWFJDDPGGNGP-UHFFFAOYSA-N 0.000 description 1
- MIULJOUNLMHJJQ-UHFFFAOYSA-N 1-cyclopropyl-7-(2,5-dimethylpiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound CC1CNC(C)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 MIULJOUNLMHJJQ-UHFFFAOYSA-N 0.000 description 1
- ZKKMWZWTLBXJGD-UHFFFAOYSA-N 1-cyclopropyl-7-(3,5-diethylpiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(CC)NC(CC)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 ZKKMWZWTLBXJGD-UHFFFAOYSA-N 0.000 description 1
- YTURORCTXHHHCR-UHFFFAOYSA-N 1-cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)NC(C)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 YTURORCTXHHHCR-UHFFFAOYSA-N 0.000 description 1
- PJDBOWKFHAMMHJ-UHFFFAOYSA-N 1-cyclopropyl-7-(3-ethylpiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CNC(CC)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 PJDBOWKFHAMMHJ-UHFFFAOYSA-N 0.000 description 1
- KNGLWEDNUXNFKP-UHFFFAOYSA-N 1-cyclopropyl-7-[4-(2-ethoxy-2-oxoethyl)piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CC(=O)OCC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 KNGLWEDNUXNFKP-UHFFFAOYSA-N 0.000 description 1
- NVEDCRRTKQEFRU-UHFFFAOYSA-N 1-cyclopropyl-7-[4-(3-ethoxy-3-oxopropyl)piperazin-1-yl]-6-nitro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CCC(=O)OCC)CCN1C(C(=C1)[N+]([O-])=O)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 NVEDCRRTKQEFRU-UHFFFAOYSA-N 0.000 description 1
- PNXKXTZGEHOPPT-UHFFFAOYSA-N 1-cyclopropyl-7-[4-(3-methoxy-3-oxopropyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CCC(=O)OC)CCN1C1=CC=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1 PNXKXTZGEHOPPT-UHFFFAOYSA-N 0.000 description 1
- DNISXBONLKEEDY-UHFFFAOYSA-N 1-cyclopropyl-7-[4-(3-methoxy-3-oxopropyl)piperazin-1-yl]-6-nitro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CCC(=O)OC)CCN1C(C(=C1)[N+]([O-])=O)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 DNISXBONLKEEDY-UHFFFAOYSA-N 0.000 description 1
- WUIJTQZXUURFQU-UHFFFAOYSA-N 1-methylsulfonylethene Chemical compound CS(=O)(=O)C=C WUIJTQZXUURFQU-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- BONFTDXNVIOQBZ-UHFFFAOYSA-N 2,4,5-trichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC(Cl)=C(Cl)C=C1Cl BONFTDXNVIOQBZ-UHFFFAOYSA-N 0.000 description 1
- KZCWJHUTTSVCRO-UHFFFAOYSA-N 2,4-dichloro-5-fluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(Cl)C=C1Cl KZCWJHUTTSVCRO-UHFFFAOYSA-N 0.000 description 1
- MRJWZKHVENHUJA-UHFFFAOYSA-N 2,4-dichloro-5-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=C(Cl)C=C1Cl MRJWZKHVENHUJA-UHFFFAOYSA-N 0.000 description 1
- CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 description 1
- OEICGMPRFOJHKO-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedinitrile Chemical compound CCOC=C(C#N)C#N OEICGMPRFOJHKO-UHFFFAOYSA-N 0.000 description 1
- HOZLOOPIXHWKCI-UHFFFAOYSA-N 2-chloro-n-methylacetamide Chemical compound CNC(=O)CCl HOZLOOPIXHWKCI-UHFFFAOYSA-N 0.000 description 1
- IKXRITWWKPLPOD-UHFFFAOYSA-N 2-chloro-n-pentylacetamide Chemical compound CCCCCNC(=O)CCl IKXRITWWKPLPOD-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- LFJJGHGXHXXDFT-UHFFFAOYSA-N 3-bromooxolan-2-one Chemical compound BrC1CCOC1=O LFJJGHGXHXXDFT-UHFFFAOYSA-N 0.000 description 1
- XEMFXXTZCZDAPK-UHFFFAOYSA-N 6,7-dichloro-1-cyclopropyl-3,4-dioxo-2H-quinoline-2-carboxylic acid Chemical compound ClC=1C=C2C(C(C(N(C2=CC=1Cl)C1CC1)C(=O)O)=O)=O XEMFXXTZCZDAPK-UHFFFAOYSA-N 0.000 description 1
- CHURZHSQTKITHE-UHFFFAOYSA-N 6-chloro-1-cyclopropyl-7-[4-(3-methoxy-3-oxopropyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CCC(=O)OC)CCN1C(C(=C1)Cl)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 CHURZHSQTKITHE-UHFFFAOYSA-N 0.000 description 1
- XWWKSLXUVZVGSP-UHFFFAOYSA-N 6-chlorohexanoic acid Chemical compound OC(=O)CCCCCCl XWWKSLXUVZVGSP-UHFFFAOYSA-N 0.000 description 1
- QLNRMVVVUGNPBE-UHFFFAOYSA-N 7-[4-(2-amino-2-oxoethyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CC(=O)N)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 QLNRMVVVUGNPBE-UHFFFAOYSA-N 0.000 description 1
- BOYYKDBJMULELA-UHFFFAOYSA-N 7-[4-(2-carboxypropyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CC(C)C(O)=O)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 BOYYKDBJMULELA-UHFFFAOYSA-N 0.000 description 1
- ZUZPSELKKNIRSP-UHFFFAOYSA-N 7-[4-(2-cyanoethyl)-3-methylpiperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CCC#N)C(C)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 ZUZPSELKKNIRSP-UHFFFAOYSA-N 0.000 description 1
- OJYUKHKKIVRFHR-UHFFFAOYSA-N 7-[4-(3-amino-3-oxopropyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CCC(=O)N)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 OJYUKHKKIVRFHR-UHFFFAOYSA-N 0.000 description 1
- YWMBAFXJBPUREQ-UHFFFAOYSA-N 7-[4-(3-carboxypropyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CCCC(=O)O)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 YWMBAFXJBPUREQ-UHFFFAOYSA-N 0.000 description 1
- OAPXPBVUQRNDHY-UHFFFAOYSA-N 7-[4-(3-cyanopropyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCN(CCCC#N)CC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 OAPXPBVUQRNDHY-UHFFFAOYSA-N 0.000 description 1
- OVAPETPAHYQXTO-UHFFFAOYSA-N 7-[4-(5-carboxypentyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CCCCCC(=O)O)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 OVAPETPAHYQXTO-UHFFFAOYSA-N 0.000 description 1
- SCQOWIWIVGRCFZ-UHFFFAOYSA-N 7-[4-(carboxymethyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CC(=O)O)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SCQOWIWIVGRCFZ-UHFFFAOYSA-N 0.000 description 1
- WDAZQWVNLRZZPJ-UHFFFAOYSA-N 7-[4-(cyanomethyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCN(CC#N)CC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 WDAZQWVNLRZZPJ-UHFFFAOYSA-N 0.000 description 1
- ZHODPMIKGLCZPG-UHFFFAOYSA-N 7-[4-[carboxy(phenyl)methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)N(CC1)CCN1C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=CC=1N2C1CC1 ZHODPMIKGLCZPG-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- 101100202529 Danio rerio scoca gene Proteins 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- ATOXTHWUFDZHBR-UHFFFAOYSA-N I.C12=CC(N3CCN(CCC(=O)OCC=4C=CC=CC=4)CC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 Chemical compound I.C12=CC(N3CCN(CCC(=O)OCC=4C=CC=CC=4)CC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ATOXTHWUFDZHBR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- AIETYZLCQUAHFC-UHFFFAOYSA-N OC(C(C(C1=C2)=O)=CN(CCCCl)C1=CC=C2F)=O Chemical compound OC(C(C(C1=C2)=O)=CN(CCCCl)C1=CC=C2F)=O AIETYZLCQUAHFC-UHFFFAOYSA-N 0.000 description 1
- 101150046895 SCOC gene Proteins 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- OOQHRQQUQCZZHF-UHFFFAOYSA-N benzyl 3-chloropropanoate Chemical compound ClCCC(=O)OCC1=CC=CC=C1 OOQHRQQUQCZZHF-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- KTMGNAIGXYODKQ-UHFFFAOYSA-N ethyl 2-cyano-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C#N)C(=O)OCC KTMGNAIGXYODKQ-UHFFFAOYSA-N 0.000 description 1
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GYQRIAVRKLRQKP-UHFFFAOYSA-N methyl 2-chloro-3-oxobutanoate Chemical compound COC(=O)C(Cl)C(C)=O GYQRIAVRKLRQKP-UHFFFAOYSA-N 0.000 description 1
- JLEJCNOTNLZCHQ-UHFFFAOYSA-N methyl 2-chloropropanoate Chemical compound COC(=O)C(C)Cl JLEJCNOTNLZCHQ-UHFFFAOYSA-N 0.000 description 1
- 229960001180 norfloxacin Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833306772 DE3306772A1 (de) | 1983-02-25 | 1983-02-25 | Chinolonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO840557L true NO840557L (no) | 1984-08-27 |
Family
ID=6191897
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO840557A NO840557L (no) | 1983-02-25 | 1984-02-15 | Kinolonkarboksylsyrer, fremgangsmaate til deres fremstilling samt antibakterielle midler som inneholder disse |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4559342A (el) |
| EP (1) | EP0117474B1 (el) |
| JP (1) | JPS59157068A (el) |
| KR (1) | KR870000891B1 (el) |
| AR (1) | AR244669A1 (el) |
| AT (1) | ATE23152T1 (el) |
| AU (1) | AU562184B2 (el) |
| CA (1) | CA1216849A (el) |
| DE (2) | DE3306772A1 (el) |
| DK (1) | DK103284A (el) |
| ES (1) | ES8500931A1 (el) |
| FI (1) | FI83955C (el) |
| GR (1) | GR79988B (el) |
| HU (1) | HU192398B (el) |
| IE (1) | IE56924B1 (el) |
| IL (1) | IL71036A (el) |
| NO (1) | NO840557L (el) |
| NZ (1) | NZ207238A (el) |
| PH (3) | PH21906A (el) |
| PT (1) | PT78114B (el) |
| ZA (1) | ZA841375B (el) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3306772A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinolonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3306771A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3308908A1 (de) * | 1983-03-12 | 1984-09-13 | Bayer Ag, 5090 Leverkusen | Bakterizide mittel |
| DE3318145A1 (de) * | 1983-05-18 | 1984-11-22 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-6,8-difluor-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3420798A1 (de) * | 1984-06-04 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | 7-(3-aryl-l-piperazinyl)- sowie 7-(3-cyclohexyl-l-piperazinyl)-3-chinoloncarbonsaeuren |
| DE3504643A1 (de) * | 1985-02-12 | 1986-08-14 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-1,4-dihydro-4-oxo-7-(4-(2-oxo-1,3-dioxol-4-yl-methyl)-1-piperazinyl)-3-chinolin carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| IT1200470B (it) * | 1985-05-10 | 1989-01-18 | Schering Spa | Composti ad attivita' antibatterica,loro preparazione e composizioni farmaceutiche relative |
| ATE72668T1 (de) * | 1985-09-24 | 1992-03-15 | Hoffmann La Roche | Chinolinderivate. |
| EP0224121A3 (en) * | 1985-11-19 | 1987-11-11 | ROTTAPHARM S.p.A. | 7-[4-amino-piperazinyl]- or 7-[4-chloro-piperazinyl]quinolinone derivatives, a process for the preparation thereof and pharmaceutical compositions containing them |
| DE3542002A1 (de) * | 1985-11-28 | 1987-06-04 | Bayer Ag | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7- (1-piperazinyl)-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3705621C2 (de) * | 1986-02-25 | 1997-01-09 | Otsuka Pharma Co Ltd | Heterocyclisch substituierte Chinoloncarbonsäurederivate |
| JPH0811749B2 (ja) * | 1986-03-06 | 1996-02-07 | 富山化学工業株式会社 | 新規なキノリン誘導体およびその塩 |
| DE3902079A1 (de) * | 1988-04-15 | 1989-10-26 | Bayer Ag | I.m. injektionsformen von gyrase-inhibitoren |
| EP0338372A3 (en) * | 1988-04-22 | 1991-10-09 | American Cyanamid Company | Solubilized pro-drugs |
| US5262417A (en) * | 1988-12-06 | 1993-11-16 | The Upjohn Company | Antibacterial quinolone compounds |
| JPH04502317A (ja) * | 1988-12-06 | 1992-04-23 | ジ・アップジョン・カンパニー | 抗菌性キノロン化合物 |
| AU2003285963A1 (en) * | 2002-11-11 | 2004-06-03 | Austria Wirtschaftsservice Gesellschaft M.B.H. | Fluorquinolines labelled with fluorine-18 |
| EP2712911A3 (en) | 2009-06-04 | 2014-08-06 | JX Nippon Oil & Energy Corporation | Lubricant oil composition |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3149104A (en) * | 1961-01-03 | 1964-09-15 | Sterling Drug Inc | 4-hydroxy-7-styryl-1, 8-naphthyridine-3-carboxylic acids and esters |
| US3590036A (en) * | 1968-11-18 | 1971-06-29 | George Y Lesher | Naphthyridine-3-carboxylic acids,their derivatives and preparation thereof |
| US4017622A (en) * | 1972-12-18 | 1977-04-12 | Dainippon Pharmaceutical Co., Ltd. | Piperazine derivatives |
| SE444566B (sv) * | 1977-09-20 | 1986-04-21 | Bellon Labor Sa Roger | 7-dialkylamin-6-halogen-4-oxo-1,4-dihydrokinolin-3-karboxylsyra, forfarande for framstellning derav och farmaceutiskt preparat derav |
| DE2808070A1 (de) * | 1978-02-24 | 1979-08-30 | Bayer Ag | Verfahren zur herstellung von 4-pyridon-3-carbonsaeuren und/oder deren derivaten |
| JPS5845426B2 (ja) * | 1978-09-29 | 1983-10-08 | 杏林製薬株式会社 | 置換キノリンカルボン酸誘導体 |
| DE3142854A1 (de) * | 1981-10-29 | 1983-05-11 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-piperazino-chinolin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3033157A1 (de) * | 1980-09-03 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| EP0090424B1 (en) * | 1982-03-31 | 1986-05-28 | Sterling Drug Inc. | New quinolone compounds and preparation thereof |
| DE3248505A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7(4- (oxoalkyl)-1-piperazinyl/-3-chinolincarbonsaeuren und ihre derivate, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3306771A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3306772A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinolonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
-
1983
- 1983-02-25 DE DE19833306772 patent/DE3306772A1/de not_active Withdrawn
-
1984
- 1984-02-03 US US06/576,596 patent/US4559342A/en not_active Expired - Lifetime
- 1984-02-08 AU AU24283/84A patent/AU562184B2/en not_active Ceased
- 1984-02-13 DE DE8484101443T patent/DE3461087D1/de not_active Expired
- 1984-02-13 EP EP84101443A patent/EP0117474B1/de not_active Expired
- 1984-02-13 AT AT84101443T patent/ATE23152T1/de not_active IP Right Cessation
- 1984-02-15 PT PT78114A patent/PT78114B/pt not_active IP Right Cessation
- 1984-02-15 NO NO840557A patent/NO840557L/no unknown
- 1984-02-21 PH PH30274A patent/PH21906A/en unknown
- 1984-02-22 NZ NZ207238A patent/NZ207238A/en unknown
- 1984-02-22 IL IL71036A patent/IL71036A/xx not_active IP Right Cessation
- 1984-02-22 JP JP59030467A patent/JPS59157068A/ja active Granted
- 1984-02-23 CA CA000448123A patent/CA1216849A/en not_active Expired
- 1984-02-23 GR GR73903A patent/GR79988B/el unknown
- 1984-02-23 FI FI840747A patent/FI83955C/fi not_active IP Right Cessation
- 1984-02-24 ZA ZA841375A patent/ZA841375B/xx unknown
- 1984-02-24 DK DK103284A patent/DK103284A/da not_active Application Discontinuation
- 1984-02-24 ES ES530045A patent/ES8500931A1/es not_active Expired
- 1984-02-24 IE IE443/84A patent/IE56924B1/en not_active IP Right Cessation
- 1984-02-24 HU HU84749A patent/HU192398B/hu not_active IP Right Cessation
- 1984-02-24 KR KR1019840000914A patent/KR870000891B1/ko not_active IP Right Cessation
-
1985
- 1985-07-09 PH PH32498A patent/PH22443A/en unknown
- 1985-07-09 PH PH32499A patent/PH23079A/en unknown
-
1986
- 1986-06-03 AR AR86304202A patent/AR244669A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| EP0117474B1 (de) | 1986-10-29 |
| ES530045A0 (es) | 1984-11-01 |
| CA1216849A (en) | 1987-01-20 |
| DK103284A (da) | 1984-08-26 |
| KR870000891B1 (ko) | 1987-05-02 |
| US4559342A (en) | 1985-12-17 |
| FI83955B (fi) | 1991-06-14 |
| AU2428384A (en) | 1984-08-30 |
| IL71036A0 (en) | 1984-05-31 |
| HU192398B (en) | 1987-06-29 |
| ES8500931A1 (es) | 1984-11-01 |
| PH22443A (en) | 1988-09-12 |
| IE840443L (en) | 1984-08-25 |
| KR840008013A (ko) | 1984-12-12 |
| FI840747A (fi) | 1984-08-26 |
| IE56924B1 (en) | 1992-01-29 |
| ZA841375B (en) | 1984-10-31 |
| FI83955C (fi) | 1991-09-25 |
| DE3306772A1 (de) | 1984-08-30 |
| PH21906A (en) | 1988-04-08 |
| PT78114A (en) | 1984-03-01 |
| EP0117474A1 (de) | 1984-09-05 |
| IL71036A (en) | 1987-12-31 |
| AU562184B2 (en) | 1987-06-04 |
| ATE23152T1 (de) | 1986-11-15 |
| PT78114B (en) | 1986-04-30 |
| JPH0430391B2 (el) | 1992-05-21 |
| DK103284D0 (da) | 1984-02-24 |
| GR79988B (el) | 1984-10-31 |
| AR244669A1 (es) | 1993-11-30 |
| FI840747A0 (fi) | 1984-02-23 |
| DE3461087D1 (en) | 1986-12-04 |
| JPS59157068A (ja) | 1984-09-06 |
| NZ207238A (en) | 1986-05-09 |
| PH23079A (en) | 1989-04-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR870000892B1 (ko) | 퀴놀론카복실산의 제조방법 | |
| NO840557L (no) | Kinolonkarboksylsyrer, fremgangsmaate til deres fremstilling samt antibakterielle midler som inneholder disse | |
| EP0230295B1 (en) | 8-alkoxyquinolonecarboxylic acid and salts thereof excellent in the selective toxicity and process of preparing the same | |
| DK166276B (da) | 7-fluor-1-cyclopropyl-6,8-dihalogen-1,4-dihydro-4-oxo-3-quinolincarboxylsyrer | |
| NO158018B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive 1-cyklopropyl-6-fluor-1,4-dihydro-4-okso-7-piperazino-kinolin-3-karboksylsyrer. | |
| EP0191185B1 (en) | Quinoline-carboxylic acid derivatives | |
| JPH0637490B2 (ja) | キノロンカルボン酸誘導体 | |
| NO170150B (no) | 3-amino-2-benzoyl-akrylsyrederivater og fremgangsmaate forfremstilling av disse | |
| NO178149B (no) | Analogifremgangsmåte for fremstilling av terapeutisk aktive 7-tetrahydro-naftyridin-6-fluor-1,4-dihydro-4-okso-kinolin-3-karboksylsyrer | |
| JP2939280B2 (ja) | フッ素置換メトキシキノロンカルボン酸誘導体 | |
| US5914401A (en) | Methods for the manufacture of quinolone carboxylic acids derivatives and intermediates thereof | |
| JP2005097116A (ja) | キノリンカルボン酸誘導体アルカリ金属塩及びこれを用いたキノリンカルボン酸誘導体の精製法 | |
| KR910003617B1 (ko) | 퀴놀론-및 나프티리돈-카르복실산의 제조방법 | |
| KR870001004B1 (ko) | 퀴놀론 카복실산의 제조방법 | |
| KR870000894B1 (ko) | 퀴놀론 카복실산의 제조방법 | |
| US5578728A (en) | Process for the preparation of a benzo(a)quinolizione derivative | |
| JP4616770B2 (ja) | 選択的なアミノ置換基導入法 | |
| JP2990903B2 (ja) | ４−オキソキノリン−３−カルボン酸類の製造方法 | |
| KR870000893B1 (ko) | 퀴놀론 카복실산의 제조방법 | |
| EP0675880B1 (en) | Quinoline disulfides as intermediates | |
| RU2002744C1 (ru) | Способ получени 1-замещенной 6-фтор-4-оксо-7-(1-пиперазинил)-1,4-дигидрохинолин-3-карбоновой кислоты | |
| JP2716952B2 (ja) | ８−メトキシキノロンカルボン酸誘導体の製造中間体 | |
| JP2556330B2 (ja) | アニソ−ル誘導体並びにその製造方法 | |
| AU2019260015A1 (en) | Process for the hydrolysis of quinolone carboxylic esters | |
| JPH089598B2 (ja) | ４―オキソ―３―キノリンカルボン酸アリルエステル類 |