CA1159454A - Derives de l'acide quinoleine-carboxylique et procede de preparation - Google Patents
Derives de l'acide quinoleine-carboxylique et procede de preparationInfo
- Publication number
- CA1159454A CA1159454A CA000358778A CA358778A CA1159454A CA 1159454 A CA1159454 A CA 1159454A CA 000358778 A CA000358778 A CA 000358778A CA 358778 A CA358778 A CA 358778A CA 1159454 A CA1159454 A CA 1159454A
- Authority
- CA
- Canada
- Prior art keywords
- dihydro
- ethyl
- carboxylic acid
- oxo
- piperazinyl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 20
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 6
- 150000004677 hydrates Chemical class 0.000 claims description 13
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- -1 N-methyl piperazinyl Chemical group 0.000 claims description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- YHRXPOLYCUTZAM-UHFFFAOYSA-N 1-ethyl-6,8-difluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 YHRXPOLYCUTZAM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- FKKUVCHFRDLBHN-UHFFFAOYSA-N 1-ethyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(F)C(F)=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 FKKUVCHFRDLBHN-UHFFFAOYSA-N 0.000 claims description 3
- JECVRHKBOILJLN-UHFFFAOYSA-N 8-chloro-1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound ClC=1C(=C(C=C2C(C(=CN(C12)CC)C(=O)O)=O)F)N1CCN(CC1)C JECVRHKBOILJLN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- GHHJVASDDBUKCH-UHFFFAOYSA-N 8-chloro-1-ethyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(F)C(Cl)=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 GHHJVASDDBUKCH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- MWCNXHXLMUQHCC-UHFFFAOYSA-N 8-chloro-1-ethyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound ClC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 MWCNXHXLMUQHCC-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229960005141 piperazine Drugs 0.000 claims 2
- RAOISAYCLQDOND-UHFFFAOYSA-N 1-ethyl-6,8-difluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C)CC1 RAOISAYCLQDOND-UHFFFAOYSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000000844 anti-bacterial effect Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- KASNWJJVSFNDJM-UHFFFAOYSA-N 1-azatricyclo[7.3.1.05,13]trideca-3,5,7,9(13),10-pentaene-3-carboxylic acid Chemical compound C1=CCN2CC(C(=O)O)=CC3=CC=CC1=C32 KASNWJJVSFNDJM-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 229940060037 fluorine Drugs 0.000 description 5
- 235000019000 fluorine Nutrition 0.000 description 5
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 230000003389 potentiating effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- CEKODOXMQSFDIZ-UHFFFAOYSA-N 5,6-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline Chemical compound FC1=CC=C2NC(C)CCC2=C1F CEKODOXMQSFDIZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000008098 formaldehyde solution Substances 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 description 3
- 229960000210 nalidixic acid Drugs 0.000 description 3
- JOHZPMXAZQZXHR-UHFFFAOYSA-N pipemidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCNCC1 JOHZPMXAZQZXHR-UHFFFAOYSA-N 0.000 description 3
- 229960001732 pipemidic acid Drugs 0.000 description 3
- 229940093956 potassium carbonate Drugs 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BUTIDJREEDINSI-UHFFFAOYSA-N 2-bromo-4,5-difluoroaniline Chemical compound NC1=CC(F)=C(F)C=C1Br BUTIDJREEDINSI-UHFFFAOYSA-N 0.000 description 2
- UQKAMONIMDBCIM-UHFFFAOYSA-N 5,6-difluoro-2-methylquinoline Chemical compound FC1=C(F)C=CC2=NC(C)=CC=C21 UQKAMONIMDBCIM-UHFFFAOYSA-N 0.000 description 2
- FXSJUFKGSLCTKW-UHFFFAOYSA-N 8-bromo-4-chloro-5,6-difluoro-2-methylquinoline Chemical compound BrC=1C=C(C(=C2C(=CC(=NC12)C)Cl)F)F FXSJUFKGSLCTKW-UHFFFAOYSA-N 0.000 description 2
- SLQILVJIQAIJGP-UHFFFAOYSA-N 8-bromo-5,6-difluoro-2-methyl-1H-quinolin-4-one Chemical compound BrC=1C=C(C(=C2C(=CC(=NC12)C)O)F)F SLQILVJIQAIJGP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000607715 Serratia marcescens Species 0.000 description 2
- 239000004280 Sodium formate Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- ONQDAESGZUODFI-UHFFFAOYSA-N ethyl 6,7,8-trifluoro-4-oxo-1h-quinoline-3-carboxylate Chemical compound FC1=C(F)C=C2C(=O)C(C(=O)OCC)=CNC2=C1F ONQDAESGZUODFI-UHFFFAOYSA-N 0.000 description 2
- ZGRIMGHOFDEZLG-UHFFFAOYSA-N ethyl 8-chloro-6,7-difluoro-4-oxo-1H-quinoline-3-carboxylate Chemical compound C(C)OC(=O)C1=CNC2=C(C(=C(C=C2C1=O)F)F)Cl ZGRIMGHOFDEZLG-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
- 235000019254 sodium formate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- LJTUWMSADLDOBG-UHFFFAOYSA-N 1-ethyl-6,8-difluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 LJTUWMSADLDOBG-UHFFFAOYSA-N 0.000 description 1
- WRDGNXCXTDDYBZ-UHFFFAOYSA-N 2,3,4-trifluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1F WRDGNXCXTDDYBZ-UHFFFAOYSA-N 0.000 description 1
- UKKFELITTUIEND-UHFFFAOYSA-N 2-chloro-3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1Cl UKKFELITTUIEND-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- VZNNMTNTTIQWLL-UHFFFAOYSA-N 6,7,8-trifluoro-1h-quinolin-2-one Chemical compound C1=CC(=O)NC2=C1C=C(F)C(F)=C2F VZNNMTNTTIQWLL-UHFFFAOYSA-N 0.000 description 1
- URJLZNXCWLEREY-UHFFFAOYSA-N 6,7-difluoro-4-oxo-1h-quinoline-3-carboxylic acid Chemical compound FC1=C(F)C=C2C(=O)C(C(=O)O)=CNC2=C1 URJLZNXCWLEREY-UHFFFAOYSA-N 0.000 description 1
- FBQWOQWRZBZQDO-UHFFFAOYSA-N 8-chloro-1-ethyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.ClC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 FBQWOQWRZBZQDO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- ABQYZRZVRIPTPI-UHFFFAOYSA-N miloxacin Chemical compound C1=C2N(OC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 ABQYZRZVRIPTPI-UHFFFAOYSA-N 0.000 description 1
- 229950007835 miloxacin Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- RCIMBBZXSXFZBV-UHFFFAOYSA-N piromidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCCC1 RCIMBBZXSXFZBV-UHFFFAOYSA-N 0.000 description 1
- 229960004444 piromidic acid Drugs 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- KVROVDQWRUAIID-UHFFFAOYSA-N quinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(C(=O)O)=CN=C21 KVROVDQWRUAIID-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached 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
- 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
- C07D215/18—Halogen atoms or nitro radicals
-
- 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
-
- 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
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54-106776 | 1979-08-22 | ||
| JP10677679A JPS5630964A (en) | 1979-08-22 | 1979-08-22 | Novel substituted quinolinecarboxylic acid and its preparation |
| BE2/58706A BE884824A (fr) | 1979-08-22 | 1980-08-19 | Derives de l'acide quinoleine-carboxylique et procede pour leur preparation |
| BE2059018 | 1981-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1159454A true CA1159454A (fr) | 1983-12-27 |
Family
ID=27159608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000358778A Expired CA1159454A (fr) | 1979-08-22 | 1980-08-21 | Derives de l'acide quinoleine-carboxylique et procede de preparation |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5630964A (fr) |
| AU (1) | AU533141B2 (fr) |
| BE (2) | BE884824A (fr) |
| CA (1) | CA1159454A (fr) |
| CH (1) | CH645641A5 (fr) |
| DE (1) | DE3031767C3 (fr) |
| ES (1) | ES8104233A1 (fr) |
| FR (1) | FR2463771A1 (fr) |
| GB (1) | GB2057440B (fr) |
| HK (1) | HK98486A (fr) |
| HU (1) | HU184817B (fr) |
| IT (1) | IT1132392B (fr) |
| MY (1) | MY8700155A (fr) |
| SE (1) | SE440353B (fr) |
| SG (1) | SG71386G (fr) |
| SU (2) | SU978727A3 (fr) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4416884A (en) * | 1978-04-12 | 1983-11-22 | Otsuka Pharmaceutical Co., Ltd. | Piperazinylbenzoheterocyclic compounds |
| NO156828C (no) * | 1980-11-10 | 1987-12-02 | Otsuka Pharma Co Ltd | Analogifremgangsm te for fremstilling av antibakterielt virksomme benzoheterocykliske forbindelser. |
| JPS57176987A (en) * | 1981-04-24 | 1982-10-30 | Otsuka Pharmaceut Co Ltd | Pyrrolo(3,2,1-ij)quinoline-5-carboxylic acid derivative |
| SE440354B (sv) * | 1981-02-19 | 1985-07-29 | Kyorin Seiyaku Kk | Kinolinkarboxylsyraderivat |
| JPS58105965A (ja) * | 1981-12-15 | 1983-06-24 | Nippon Shinyaku Co Ltd | 置換キノリンカルボン酸誘導体 |
| US4472406A (en) * | 1982-11-12 | 1984-09-18 | Riker Laboratories, Inc. | Antimicrobial 6,7-dihydro-8-(imidazol-1-yl)-5-methyl-1-oxo-1H,5H-benzo [ij]quinolizine-2-carboxylic acids and derivatives |
| US4472405A (en) * | 1982-11-12 | 1984-09-18 | Riker Laboratories, Inc. | Antimicrobial 6,7-dihydro-5,8-dimethyl-9 fluoro-1-oxo-1H, 5H-benzo (ij) quinolizine-2-carboxylic acid and derivatives |
| JPS59128383A (ja) * | 1982-12-29 | 1984-07-24 | Kanebo Ltd | 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 |
| JPS59155381A (ja) * | 1983-02-22 | 1984-09-04 | Kyorin Pharmaceut Co Ltd | ベンゾキノリジンカルボン酸誘導体及びその製造法 |
| 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 |
| JPS59195842U (ja) * | 1983-06-13 | 1984-12-26 | クラリオン株式会社 | ラジオ受信機 |
| AU553415B2 (en) * | 1983-09-19 | 1986-07-17 | Abbott Japan Co., Ltd. | 6-fluoro-1-4-dihydro-4-oxo-7-substituted piperazinyl- quinoline-3-carboxylic acids |
| US4571396A (en) * | 1984-04-16 | 1986-02-18 | Warner-Lambert Company | Antibacterial agents |
| GB8412094D0 (en) * | 1984-05-11 | 1984-06-20 | Scras | Quinoline derivatives |
| US5468861A (en) * | 1984-06-04 | 1995-11-21 | Bayer Aktiengesellschaft | 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and alkyl esters thereof |
| 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 |
| US4550103A (en) * | 1984-07-20 | 1985-10-29 | Warner-Lambert Company | Antibacterial 1-oxo-benzoquinolizine-2-carboxylic acids |
| US4550104A (en) * | 1984-07-20 | 1985-10-29 | Warner-Lambert Company | Antibacterial thiazolo-quinolines and thiazolo-naphthyridines |
| JPS61118370A (ja) * | 1985-10-30 | 1986-06-05 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸とその製造方法 |
| ZA859283B (en) * | 1984-12-06 | 1987-07-29 | Pfizer | Substituted dihydroquinolone carboxylic acids and anti-bacterial compositions containing them |
| JPS61143363A (ja) * | 1984-12-17 | 1986-07-01 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体の製造方法 |
| JPS61143364A (ja) * | 1984-12-17 | 1986-07-01 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体の製造方法 |
| JPS61205258A (ja) * | 1985-03-08 | 1986-09-11 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体及びその製造方法 |
| AU5427286A (en) * | 1985-03-08 | 1986-09-11 | Kyorin Pharmaceutical Co. Ltd. | 7-(1-pyrrolidinyl)-3-quinolinecarboxylic acid derivatives |
| ATE77373T1 (de) * | 1985-03-21 | 1992-07-15 | Kyorin Seiyaku Kk | Verfahren zur herstellung von chinolinsaeurederivaten. |
| GB8512143D0 (en) * | 1985-05-14 | 1985-06-19 | Beecham Group Plc | Method of treatment |
| US4686221A (en) * | 1985-10-01 | 1987-08-11 | Kanebo, Ltd. | Quinolinecarboxylic acid compounds and antimicrobial agent containing the same |
| JPS62228063A (ja) * | 1985-12-27 | 1987-10-06 | Sankyo Co Ltd | キノリンカルボン酸誘導体 |
| JPH0753715B2 (ja) * | 1986-02-25 | 1995-06-07 | 大塚製薬株式会社 | ベンゾヘテロ環化合物 |
| DE3705621C2 (de) * | 1986-02-25 | 1997-01-09 | Otsuka Pharma Co Ltd | Heterocyclisch substituierte Chinoloncarbonsäurederivate |
| JPS62205060A (ja) * | 1986-03-04 | 1987-09-09 | Kyorin Pharmaceut Co Ltd | ８位置換キノロンカルボン酸誘導体 |
| JPS62215572A (ja) * | 1986-03-17 | 1987-09-22 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体 |
| ZA874696B (en) * | 1986-07-03 | 1988-01-04 | F. Hoffmann-La Roche & Co. Aktiengesellschaft | Acyl derivatives |
| US5563138A (en) * | 1987-04-16 | 1996-10-08 | 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 |
| JPS6483068A (en) * | 1987-09-25 | 1989-03-28 | Otsuka Pharma Co Ltd | Production of benzo-heterocyclic compound |
| JPH01175936A (ja) * | 1987-12-28 | 1989-07-12 | Kyorin Pharmaceut Co Ltd | ６．８−ジフルオロ−１−（２−フルオロエチル）−１，４−ジヒドロ−７−（４−メチル−１−ピペラジニル）−４−オキソ−３−キノリンカルボン酸を有効成分とする錠剤 |
| JP2526128B2 (ja) * | 1988-08-08 | 1996-08-21 | エスエス製薬株式会社 | キノロンカルボン酸誘導体 |
| US5185337A (en) * | 1989-03-29 | 1993-02-09 | Otsuka Pharmaceutical Co., Ltd. | Pyrroloquinoline derivatives and pharmaceutical compositions for antimicrobial use |
| CA2058424A1 (fr) * | 1989-07-21 | 1991-01-22 | Akihiro Shibata | Derives d'acide quinoleinecarboxylique |
| FR2655545B1 (fr) | 1989-12-11 | 1994-06-10 | Rhone Poulenc Sante | Nouvelle application therapeutique des derives des fluoroquinolones. |
| FR2656611B1 (fr) * | 1990-01-04 | 1992-05-07 | Hoechst France | Nouvelles quinolones, leurs sels, utiles comme agents antimicrobiens, procede de preparation et leur application a titre de medicaments et compositions les renfermant. |
| FR2673426B1 (fr) * | 1991-03-01 | 1993-07-16 | Bouchara Sa | Nouvelles quinolones, leur procede de preparation et les compositions en refermant. |
| FR2675144B1 (fr) * | 1991-04-10 | 1995-06-16 | Bouchara Sa | Nouvelles quinolones difluorees - leur procede de preparation et les compositions pharmaceutiques en renfermant. |
| US5532239A (en) * | 1993-08-02 | 1996-07-02 | Assistance Publique - Hopitaux De Paris | Therapeutic application of fluoroquinolone derivatives |
| US5731440A (en) * | 1994-03-01 | 1998-03-24 | Ishihara Sangyo Kaisha Ltd. | Intermediates for producing 5,7-dichloro-4-hydroxyquinoline |
| SE9904108D0 (sv) | 1999-11-15 | 1999-11-15 | New Pharma Research Ab | Nya föreningar |
| US7973022B2 (en) | 2006-02-17 | 2011-07-05 | Idexx Laboratories, Inc. | Fluoroquinolone carboxylic acid salt compositions |
| US20070197548A1 (en) | 2006-02-17 | 2007-08-23 | Murthy Yerramilli V S | Fluoroquinolone compositions |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7101049A (fr) * | 1970-01-28 | 1971-07-30 | ||
| BE793524A (fr) * | 1971-12-30 | 1973-06-29 | Riker Laboratories Inc | Acides benzoquinolizine-carboxyliques et leurs derives |
| US4156726A (en) * | 1974-12-07 | 1979-05-29 | Fisons Limited | 4-Oxo-2-carboxyl quinoline derivatives used as antiallergic compounds |
| JPS53141286A (en) * | 1977-05-16 | 1978-12-08 | Kyorin Seiyaku Kk | Novel substituted quinolinecarboxylic acid |
| JPS54112877A (en) | 1978-02-20 | 1979-09-04 | Sumitomo Chem Co Ltd | Preparation of 1-substituted-1,4-dihydro-4-oxo-3-pyridine carboxylic acid derivatives |
| DE2914258A1 (de) * | 1978-04-12 | 1979-10-25 | Otsuka Pharma Co Ltd | Piperazinylbenzoheterozyklische verbindungen, verfahren zu deren herstellung und mittel, welche diese enthalten |
| AU553415B2 (en) * | 1983-09-19 | 1986-07-17 | Abbott Japan Co., Ltd. | 6-fluoro-1-4-dihydro-4-oxo-7-substituted piperazinyl- quinoline-3-carboxylic acids |
-
1979
- 1979-08-22 JP JP10677679A patent/JPS5630964A/ja active Pending
-
1980
- 1980-08-04 SE SE8005534A patent/SE440353B/sv not_active IP Right Cessation
- 1980-08-06 AU AU61122/80A patent/AU533141B2/en not_active Expired
- 1980-08-11 IT IT24111/80A patent/IT1132392B/it active
- 1980-08-14 CH CH614680A patent/CH645641A5/de not_active IP Right Cessation
- 1980-08-19 ES ES494352A patent/ES8104233A1/es not_active Expired
- 1980-08-19 BE BE2/58706A patent/BE884824A/fr not_active IP Right Cessation
- 1980-08-21 FR FR8018279A patent/FR2463771A1/fr active Granted
- 1980-08-21 HU HU802072A patent/HU184817B/hu unknown
- 1980-08-21 CA CA000358778A patent/CA1159454A/fr not_active Expired
- 1980-08-21 SU SU802968349A patent/SU978727A3/ru active
- 1980-08-22 GB GB8027372A patent/GB2057440B/en not_active Expired
- 1980-08-22 DE DE3031767A patent/DE3031767C3/de not_active Expired - Lifetime
-
1981
- 1981-02-19 BE BE2/59018A patent/BE887574R/fr not_active IP Right Cessation
- 1981-03-03 SU SU813254244A patent/SU1015827A3/ru active
-
1986
- 1986-09-04 SG SG713/86A patent/SG71386G/en unknown
- 1986-12-18 HK HK984/86A patent/HK98486A/xx not_active IP Right Cessation
-
1987
- 1987-12-30 MY MY155/87A patent/MY8700155A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT1132392B (it) | 1986-07-02 |
| DE3031767C2 (fr) | 1994-04-14 |
| SG71386G (en) | 1987-03-27 |
| DE3031767A1 (de) | 1981-03-26 |
| AU6112280A (en) | 1981-02-26 |
| FR2463771A1 (fr) | 1981-02-27 |
| ES494352A0 (es) | 1981-04-16 |
| MY8700155A (en) | 1987-12-31 |
| HK98486A (en) | 1986-12-24 |
| HU184817B (en) | 1984-10-29 |
| SU1015827A3 (ru) | 1983-04-30 |
| AU533141B2 (en) | 1983-11-03 |
| DE3031767C3 (de) | 1994-04-14 |
| SU978727A3 (ru) | 1982-11-30 |
| IT8024111A0 (it) | 1980-08-11 |
| GB2057440A (en) | 1981-04-01 |
| BE884824A (fr) | 1980-12-16 |
| JPS5630964A (en) | 1981-03-28 |
| ES8104233A1 (es) | 1981-04-16 |
| BE887574R (fr) | 1981-06-15 |
| FR2463771B1 (fr) | 1983-04-22 |
| GB2057440B (en) | 1983-10-12 |
| SE8005534L (sv) | 1981-02-23 |
| CH645641A5 (de) | 1984-10-15 |
| SE440353B (sv) | 1985-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |