NO852076L - Fremgangsmaate ved fremstilling av kinolinkarboksylsyrederivater. - Google Patents
Fremgangsmaate ved fremstilling av kinolinkarboksylsyrederivater.Info
- Publication number
- NO852076L NO852076L NO852076A NO852076A NO852076L NO 852076 L NO852076 L NO 852076L NO 852076 A NO852076 A NO 852076A NO 852076 A NO852076 A NO 852076A NO 852076 L NO852076 L NO 852076L
- Authority
- NO
- Norway
- Prior art keywords
- chloro
- water
- concentrated
- acid
- title compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 54
- 239000002253 acid Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 20
- 239000005457 ice water Substances 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 6
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- NUBFPWXUKJGZNA-UHFFFAOYSA-N ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(Cl)C(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 NUBFPWXUKJGZNA-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- -1 for example Chemical class 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
- 239000003208 petroleum Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- AMVKEEYBJIRRGV-UHFFFAOYSA-N 2,3,4-trichloro-1-fluoro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(F)=C(Cl)C(Cl)=C1Cl AMVKEEYBJIRRGV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000192125 Firmicutes Species 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 229960003405 ciprofloxacin Drugs 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- QHMLKJCHGKGKDP-UHFFFAOYSA-N 2,3,4-trichloro-5-fluoroaniline Chemical compound NC1=CC(F)=C(Cl)C(Cl)=C1Cl QHMLKJCHGKGKDP-UHFFFAOYSA-N 0.000 description 2
- OKRWBTOWNXSEKG-UHFFFAOYSA-N 2,3,4-trichloro-5-fluorobenzonitrile Chemical compound FC1=CC(C#N)=C(Cl)C(Cl)=C1Cl OKRWBTOWNXSEKG-UHFFFAOYSA-N 0.000 description 2
- QPLHELABGKHHRL-UHFFFAOYSA-N 2,3-dichloro-4-fluoro-6-nitroaniline Chemical compound NC1=C(Cl)C(Cl)=C(F)C=C1[N+]([O-])=O QPLHELABGKHHRL-UHFFFAOYSA-N 0.000 description 2
- CPVMPAHLYNHPHY-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-3,4-difluoro-6-nitroaniline Chemical compound [O-][N+](=O)C1=CC(F)=C(F)C(Cl)=C1NC1CC1 CPVMPAHLYNHPHY-UHFFFAOYSA-N 0.000 description 2
- QNBDAPZLQYFUIX-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-3,4-difluoroaniline Chemical compound ClC1=C(F)C(F)=CC=C1NC1CC1 QNBDAPZLQYFUIX-UHFFFAOYSA-N 0.000 description 2
- BMRPNIIBXSCMHX-UHFFFAOYSA-N 3-chloro-1,2,4-trifluoro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(F)=C(F)C(Cl)=C1F BMRPNIIBXSCMHX-UHFFFAOYSA-N 0.000 description 2
- XGIMFAMVOLVNPP-UHFFFAOYSA-N 3-chloro-2,4,5-trifluorobenzamide Chemical compound NC(=O)C1=CC(F)=C(F)C(Cl)=C1F XGIMFAMVOLVNPP-UHFFFAOYSA-N 0.000 description 2
- KBESHLYCSZINAJ-UHFFFAOYSA-N 3-chloro-2,4,5-trifluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C(Cl)=C1F KBESHLYCSZINAJ-UHFFFAOYSA-N 0.000 description 2
- BRANJOPEMMWETD-UHFFFAOYSA-N 3-chloro-2,4,5-trifluorobenzonitrile Chemical compound FC1=CC(C#N)=C(F)C(Cl)=C1F BRANJOPEMMWETD-UHFFFAOYSA-N 0.000 description 2
- IEDMMCZBIKXEJP-UHFFFAOYSA-N 3-chloro-2,4,5-trifluorobenzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=C(F)C(Cl)=C1F IEDMMCZBIKXEJP-UHFFFAOYSA-N 0.000 description 2
- VRJKEIWZSOHDOH-UHFFFAOYSA-N 5-chloro-4-fluoro-2-nitroaniline Chemical compound NC1=CC(Cl)=C(F)C=C1[N+]([O-])=O VRJKEIWZSOHDOH-UHFFFAOYSA-N 0.000 description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
- 108010054814 DNA Gyrase Proteins 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 102000017033 Porins Human genes 0.000 description 2
- 108010013381 Porins Proteins 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000607715 Serratia marcescens Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000006196 drop Substances 0.000 description 2
- VOLUOOYGRKDBSQ-VURMDHGXSA-N ethyl (z)-2-(3-chloro-2,4,5-trifluorobenzoyl)-3-ethoxyprop-2-enoate Chemical compound CCO\C=C(/C(=O)OCC)C(=O)C1=CC(F)=C(F)C(Cl)=C1F VOLUOOYGRKDBSQ-VURMDHGXSA-N 0.000 description 2
- KISUGMULAAIILF-UHFFFAOYSA-N ethyl 2-(3-chloro-2,4,5-trifluorobenzoyl)-3-(cyclopropylamino)prop-2-enoate Chemical compound C=1C(F)=C(F)C(Cl)=C(F)C=1C(=O)C(C(=O)OCC)=CNC1CC1 KISUGMULAAIILF-UHFFFAOYSA-N 0.000 description 2
- LZMXLCPYJNRWNQ-UHFFFAOYSA-N ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC(F)=C(F)C(Cl)=C1F LZMXLCPYJNRWNQ-UHFFFAOYSA-N 0.000 description 2
- WQJHSSLKRZANNU-UHFFFAOYSA-N ethyl 8-chloro-1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylate Chemical compound C12=C(Cl)C(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 WQJHSSLKRZANNU-UHFFFAOYSA-N 0.000 description 2
- YFVXZHLWTHQSGK-UHFFFAOYSA-N ethyl 8-chloro-1-cyclopropyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylate Chemical compound C12=C(Cl)C(N3CCN(C)CC3)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 YFVXZHLWTHQSGK-UHFFFAOYSA-N 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- NPPKGDIJVVGOAG-UHFFFAOYSA-N n-(2-chloro-3,4-difluoro-6-nitrophenyl)-n-cyclopropylacetamide Chemical compound ClC=1C(F)=C(F)C=C([N+]([O-])=O)C=1N(C(=O)C)C1CC1 NPPKGDIJVVGOAG-UHFFFAOYSA-N 0.000 description 2
- MXDGLNPPGFOABX-UHFFFAOYSA-N n-(2-chloro-3,4-difluorophenyl)-n-cyclopropylacetamide Chemical compound C=1C=C(F)C(F)=C(Cl)C=1N(C(=O)C)C1CC1 MXDGLNPPGFOABX-UHFFFAOYSA-N 0.000 description 2
- ALPHMTFVUKDBGJ-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(F)C(Cl)=C1 ALPHMTFVUKDBGJ-UHFFFAOYSA-N 0.000 description 2
- PFFDKLGOPDBQQD-UHFFFAOYSA-N n-(5-chloro-4-fluoro-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(F)C=C1[N+]([O-])=O PFFDKLGOPDBQQD-UHFFFAOYSA-N 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
- 229960001180 norfloxacin Drugs 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
- 239000012414 tert-butyl nitrite 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 1
- YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 1
- UGQWPWIPFYFCFJ-UHFFFAOYSA-N 8-chloro-1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 UGQWPWIPFYFCFJ-UHFFFAOYSA-N 0.000 description 1
- MGHCMEUPZPAKMY-UHFFFAOYSA-N 8-chloro-1-cyclopropyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1Cl MGHCMEUPZPAKMY-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 238000004617 QSAR study Methods 0.000 description 1
- 241000607714 Serratia sp. Species 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 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
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229940124307 fluoroquinolone Drugs 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment 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
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- XKGUKYPCHPHAJL-UHFFFAOYSA-N methanetetracarbonitrile Chemical compound N#CC(C#N)(C#N)C#N XKGUKYPCHPHAJL-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910001577 potassium mineral Inorganic materials 0.000 description 1
- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60046216A JPS61205258A (ja) | 1985-03-08 | 1985-03-08 | キノロンカルボン酸誘導体及びその製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO852076L true NO852076L (no) | 1986-09-09 |
Family
ID=12740905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO852076A NO852076L (no) | 1985-03-08 | 1985-05-23 | Fremgangsmaate ved fremstilling av kinolinkarboksylsyrederivater. |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0195841A1 (xx) |
| JP (1) | JPS61205258A (xx) |
| KR (1) | KR860007244A (xx) |
| CN (1) | CN1010778B (xx) |
| AU (1) | AU4282985A (xx) |
| DK (1) | DK241585A (xx) |
| ES (1) | ES8606330A1 (xx) |
| FI (1) | FI852172L (xx) |
| GR (1) | GR851299B (xx) |
| HU (1) | HU194865B (xx) |
| MX (1) | MX159506A (xx) |
| NO (1) | NO852076L (xx) |
| NZ (1) | NZ212239A (xx) |
| PH (1) | PH20703A (xx) |
| PT (1) | PT80546B (xx) |
| ZA (1) | ZA853954B (xx) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3420743A1 (de) * | 1984-06-04 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-6,8-dihalogen-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| US4977154A (en) * | 1985-12-12 | 1990-12-11 | Warner-Lambert Company | 5-amino and 5-hydroxy-6-fluoroquinolones as antibacterial agents |
| US4668680A (en) * | 1985-12-12 | 1987-05-26 | Warner-Lambert Company | 5-amino-6,8-difluoroquinolones as antibacterial agents |
| DE3705621C2 (de) * | 1986-02-25 | 1997-01-09 | Otsuka Pharma Co Ltd | Heterocyclisch substituierte Chinoloncarbonsäurederivate |
| DE3635218A1 (de) * | 1986-10-16 | 1988-04-21 | Bayer Ag | 7-amino-1-cyclopropyl-8-chlor-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3641312A1 (de) * | 1986-12-03 | 1988-06-09 | Bayer Ag | Verfahren zur herstellung von chinolincarbonsaeuren |
| US5591744A (en) * | 1987-04-16 | 1997-01-07 | Otsuka Pharmaceutical Company, Limited | Benzoheterocyclic compounds |
| US4851418A (en) * | 1987-08-21 | 1989-07-25 | Warner-Lambert Company | Naphthyridine antibacterial agents containing an α-amino acid in the side chain of the 7-substituent |
| HUP0100051A3 (en) * | 1997-09-15 | 2002-08-28 | Procter & Gamble | Antimicrobial quinolones, their compositions and uses |
| MXPA02007667A (es) | 2000-02-09 | 2003-04-14 | Daiichi Seiyaku Co | Agentes antibacterianos antiacidos-resistentes que contienen acidos piridoncarboxilicos como el ingrediente activo. |
| KR101084521B1 (ko) | 2006-03-28 | 2011-11-18 | 워너 칠콧 컴퍼니 엘엘씨 | 퀴놀론 중간체를 제조하기 위한 커플링 방법 |
| MX2008012328A (es) | 2006-03-28 | 2008-10-09 | Procter & Gamble | Sales de malato, y polimorfos de acido (3s,5s)-7-[3-amino-5-metil- piperidinil]-1-ciclopropil-1,4-dihidro-8-metoxi-4-oxo-3-quinolinc arboxilico. |
| CN103709100A (zh) * | 2013-12-31 | 2014-04-09 | 南京工业大学 | 一种8-氯代喹诺酮衍生物的制备方法 |
| CN114790133B (zh) * | 2021-01-26 | 2024-06-18 | 江苏中旗科技股份有限公司 | 一种以2-氯-4-氨基苯腈为原料合成2-氯-4-氟苯甲酸的方法 |
| CN114790139B (zh) * | 2021-01-26 | 2024-06-18 | 江苏中旗科技股份有限公司 | 一种以2-氯-4-氨基溴苯为原料合成2-氯-4-氟苯甲酸的方法 |
| CN114716373B (zh) * | 2022-04-14 | 2023-01-10 | 内蒙古源宏精细化工有限公司 | 一种加替沙星环合酯的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5630964A (en) * | 1979-08-22 | 1981-03-28 | Kyorin Pharmaceut Co Ltd | Novel substituted quinolinecarboxylic acid and its preparation |
| JPS60123837A (ja) * | 1983-12-09 | 1985-07-02 | Mitsubishi Paper Mills Ltd | ハロゲン化銀写真乳剤 |
| DE3420743A1 (de) * | 1984-06-04 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-6,8-dihalogen-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
-
1985
- 1985-03-08 JP JP60046216A patent/JPS61205258A/ja active Pending
- 1985-05-23 PH PH32303A patent/PH20703A/en unknown
- 1985-05-23 AU AU42829/85A patent/AU4282985A/en not_active Abandoned
- 1985-05-23 HU HU851962A patent/HU194865B/hu not_active IP Right Cessation
- 1985-05-23 NO NO852076A patent/NO852076L/no unknown
- 1985-05-24 ZA ZA853954A patent/ZA853954B/xx unknown
- 1985-05-27 GR GR851299A patent/GR851299B/el unknown
- 1985-05-29 NZ NZ212239A patent/NZ212239A/en unknown
- 1985-05-29 PT PT80546A patent/PT80546B/pt not_active IP Right Cessation
- 1985-05-29 KR KR1019850003710A patent/KR860007244A/ko not_active Application Discontinuation
- 1985-05-29 EP EP85106626A patent/EP0195841A1/en not_active Withdrawn
- 1985-05-30 FI FI852172A patent/FI852172L/fi not_active Application Discontinuation
- 1985-05-30 ES ES543686A patent/ES8606330A1/es not_active Expired
- 1985-05-30 DK DK241585A patent/DK241585A/da not_active Application Discontinuation
- 1985-05-31 MX MX205477A patent/MX159506A/es unknown
- 1985-06-19 CN CN85107319A patent/CN1010778B/zh not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK241585A (da) | 1986-09-09 |
| HU194865B (en) | 1988-03-28 |
| AU4282985A (en) | 1986-09-11 |
| CN1010778B (zh) | 1990-12-12 |
| PH20703A (en) | 1987-03-24 |
| GR851299B (xx) | 1985-11-25 |
| ZA853954B (en) | 1986-01-29 |
| NZ212239A (en) | 1988-02-12 |
| HUT38337A (en) | 1986-05-28 |
| FI852172L (fi) | 1986-09-09 |
| PT80546A (en) | 1985-06-01 |
| JPS61205258A (ja) | 1986-09-11 |
| MX159506A (es) | 1989-06-21 |
| ES8606330A1 (es) | 1986-04-01 |
| KR860007244A (ko) | 1986-10-10 |
| CN85104693A (zh) | 1986-09-03 |
| PT80546B (en) | 1986-12-15 |
| FI852172A0 (fi) | 1985-05-30 |
| EP0195841A1 (en) | 1986-10-01 |
| DK241585D0 (da) | 1985-05-30 |
| ES543686A0 (es) | 1986-04-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0230295B1 (en) | 8-alkoxyquinolonecarboxylic acid and salts thereof excellent in the selective toxicity and process of preparing the same | |
| KR940007305B1 (ko) | 8-위치에서 치환된 퀴놀론카복실산 유도체, 이의 제조방법 및 이를 함유하는 약제학적 조성물 | |
| NO852076L (no) | Fremgangsmaate ved fremstilling av kinolinkarboksylsyrederivater. | |
| KR920006236B1 (ko) | 퀴놀론카복실산 유도체의 제조방법 | |
| JP2520549B2 (ja) | フルオロシクロプロピルアミノアクリル酸エステル誘導体 | |
| JPS611683A (ja) | ７‐（３‐アリール‐１‐ピペラジニル）‐及び７‐（３‐シクロヘキシル‐１‐ピペラジニル）‐３‐キノロンカルボン酸類 | |
| KR930011036B1 (ko) | 퀴놀론카복실산 유도체의 제조방법 | |
| HU195495B (en) | Process for the production of new derivatives of kynolincarbonic acid and medical preparatives containing them | |
| NZ209193A (en) | Substituted tetrazolyl quinolone derivatives and pharmaceutical compositions | |
| EP0216245B1 (en) | Quinolonecarboxylic acid derivatives and process for their preparation | |
| JPS62174055A (ja) | 新規キノリンカルボン酸誘導体および該化合物を有効成分とする抗菌剤 | |
| JPH0680640A (ja) | 選択毒性に優れた８−アルコキシキノロンカルボン酸およびその塩並びにその製造方法 | |
| JPS61118370A (ja) | キノロンカルボン酸とその製造方法 |