CA1218067A - 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazino- quinoline-3-carboxylic acids, a process for their preparation and antibacterial agents containing these compounds - Google Patents
1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazino- quinoline-3-carboxylic acids, a process for their preparation and antibacterial agents containing these compoundsInfo
- Publication number
- CA1218067A CA1218067A CA000409435A CA409435A CA1218067A CA 1218067 A CA1218067 A CA 1218067A CA 000409435 A CA000409435 A CA 000409435A CA 409435 A CA409435 A CA 409435A CA 1218067 A CA1218067 A CA 1218067A
- Authority
- CA
- Canada
- Prior art keywords
- fluoro
- ethyl
- process according
- dihydro
- oxo
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 37
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical class C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 title claims abstract 6
- 238000002360 preparation method Methods 0.000 title description 5
- 239000003242 anti bacterial agent Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
- 239000003085 diluting agent Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 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 claims description 13
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 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 claims description 10
- 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 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000012312 sodium hydride Substances 0.000 claims description 6
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 6
- 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 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 3
- 150000004885 piperazines Chemical class 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- TXJIOKSSHCOKKH-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 TXJIOKSSHCOKKH-UHFFFAOYSA-N 0.000 claims 2
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 claims 1
- SPFYMRJSYKOXGV-UHFFFAOYSA-N Baytril Chemical compound C1CN(CC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SPFYMRJSYKOXGV-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 23
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- 239000003814 drug Substances 0.000 description 14
- 239000008194 pharmaceutical composition Substances 0.000 description 13
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- 239000002904 solvent Substances 0.000 description 13
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- -1 hexamethyl-phosphoric acid Chemical compound 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
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- 230000000844 anti-bacterial effect Effects 0.000 description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
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- 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 2
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- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 150000005827 chlorofluoro hydrocarbons Chemical class 0.000 description 1
- 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 1
- 239000004927 clay Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 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 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 239000010642 eucalyptus oil Substances 0.000 description 1
- 229940044949 eucalyptus oil Drugs 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000010470 malonic ester synthesis reaction Methods 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Fodder In General (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000617148A CA1341371C (en) | 1981-10-29 | 1982-08-13 | Alkyl 2-(2,4-dichloro-5-fluorobenzol)-3-ethoxy-acrylates and process for their preparation |
| CA000508436A CA1237431A (en) | 1981-10-29 | 1986-05-05 | 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-chloro- quinoline-3-carboxylic acid, esters and process for their preparation |
| CA000508435A CA1272210A (en) | 1981-10-29 | 1986-05-05 | Alkyl 2,4-dichloro-5-fluorobenzoyl-acetates and process for their preparation |
| CA000615913A CA1322334C (en) | 1981-10-29 | 1990-10-26 | 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazino- quinoline-3-carboxylic acid- containing compositions and uses thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813142854 DE3142854A1 (de) | 1981-10-29 | 1981-10-29 | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-piperazino-chinolin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DEP3142854.1 | 1981-11-29 |
Related Child Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000617148A Division CA1341371C (en) | 1981-10-29 | 1982-08-13 | Alkyl 2-(2,4-dichloro-5-fluorobenzol)-3-ethoxy-acrylates and process for their preparation |
| CA000508435A Division CA1272210A (en) | 1981-10-29 | 1986-05-05 | Alkyl 2,4-dichloro-5-fluorobenzoyl-acetates and process for their preparation |
| CA000615913A Division CA1322334C (en) | 1981-10-29 | 1990-10-26 | 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazino- quinoline-3-carboxylic acid- containing compositions and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1218067A true CA1218067A (en) | 1987-02-17 |
Family
ID=6145081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000409435A Expired CA1218067A (en) | 1981-10-29 | 1982-08-13 | 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazino- quinoline-3-carboxylic acids, a process for their preparation and antibacterial agents containing these compounds |
Country Status (20)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013157018A1 (en) | 2012-04-18 | 2013-10-24 | Indian Institute Of Technology Madras | A process for the preparation of the core structure in quinolone and napthyridone class of antibiotics |
Families Citing this family (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE3248506A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7(alkyl-1-piperazinyl)-3-chinolincarbonsaeuren, 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 |
| 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 |
| US4730000A (en) * | 1984-04-09 | 1988-03-08 | Abbott Laboratories | Quinoline antibacterial compounds |
| US4551456A (en) * | 1983-11-14 | 1985-11-05 | Merck & Co., Inc. | Ophthalmic use of norfloxacin and related antibiotics |
| DE3574380D1 (en) * | 1984-02-17 | 1989-12-28 | Daiichi Seiyaku Co | 1,8-naphthyridine derivatives |
| US4529725A (en) * | 1984-04-26 | 1985-07-16 | Abbott Laboratories | 1-Pyridine substituted quino-benzothiazine |
| US4607032A (en) * | 1984-04-26 | 1986-08-19 | Abbott Laboratories | Quino-benoxazine antibacterial compounds |
| US4533663A (en) * | 1984-04-26 | 1985-08-06 | Abbott Laboratories | Quino-benzothiazine antibacterial compounds |
| US4528285A (en) * | 1984-04-26 | 1985-07-09 | Abbott Laboratories | Methylenedioxy quino-benzothiazine derivatives |
| US4540694A (en) * | 1984-04-26 | 1985-09-10 | Abbott Laboratories | 1-Pyridine substituted quino-benoxazines and antibacterial use |
| US4542133A (en) * | 1984-04-26 | 1985-09-17 | Abbott Laboratories | Methylenedioxy quino-benoxazine derivatives and antibacterial use |
| GB8412094D0 (en) * | 1984-05-11 | 1984-06-20 | Scras | Quinoline derivatives |
| 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 |
| DE3426482A1 (de) * | 1984-07-18 | 1986-01-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von halogenierten aroylessigestern |
| IE58742B1 (en) * | 1984-07-20 | 1993-11-05 | Warner Lambert Co | Substituted-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7h-pyrido[1,2,3-de] [1,4]benzoxauine-6-carboxylic acids; sibstituted-5-amino-6-6fluoro-4-oxo.1,4-dihydroquinoline-3 carboxylic acids; substituted-5-amino-6-fluoro-1,4-dihydro-4-oxo-1.8-naphthyridine-3-carboxylic acids; derivatives thereof; pharmaceutical compositions comprising the compounds; and processes for producing the compounds |
| DE3502935A1 (de) * | 1984-09-29 | 1986-04-10 | Bayer Ag, 5090 Leverkusen | 3-amino-2-benzoyl-acrylsaeurederivate und ein verfahren zu ihrer herstellung |
| FR2574404B1 (fr) * | 1984-12-12 | 1987-04-24 | Provesan Sa | Derives 1-substitues de l'acide 6-fluoro-7-(pyrrol-1-yl)-1,4-dihydro-4-oxoquinoleine-3-carboxylique, leur preparation et leur application en tant que medicaments |
| DE3576335D1 (de) * | 1984-12-14 | 1990-04-12 | Daiichi Seiyaku Co | Chinolincarbonsaeure-derivate. |
| DE3517709A1 (de) * | 1985-01-05 | 1986-07-10 | Bayer Ag | Basische zubereitungen von chinoloncarbonsaeuren |
| JPS61180771A (ja) * | 1985-01-05 | 1986-08-13 | バイエル・アクチエンゲゼルシヤフト | 安定な抗バクテリア剤水溶液 |
| DE3508816A1 (de) * | 1985-01-10 | 1986-07-10 | Bayer Ag, 5090 Leverkusen | 6,7-disubstituierte 1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphtyridin-3-carbonsaeuren |
| DE3501247A1 (de) * | 1985-01-16 | 1986-07-17 | Bayer Ag, 5090 Leverkusen | Aminoacrylsaeure-derivate |
| AT392789B (de) * | 1985-01-23 | 1991-06-10 | Toyama Chemical Co Ltd | Verfahren zur herstellung von 1-substituierten aryl-1,4-dihydro-4-oxonaphthyridinderivaten |
| AT392791B (de) * | 1985-01-23 | 1991-06-10 | Toyama Chemical Co Ltd | Verfahren zur herstellung von 1-substituierten aryl-1,4-dihydro-4-oxonaphthyridinderivaten |
| US4851535A (en) * | 1985-01-23 | 1989-07-25 | Toyama Chemical Co., Ltd. | Nicotinic acid derivatives |
| DE3509546A1 (de) * | 1985-03-16 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | 7-amino-1-(subst.cyclopropyl)-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3608745A1 (de) * | 1985-07-24 | 1987-01-29 | Bayer Ag | Bakterizide zubereitungen zur anwendung auf dem gebiet der veterinaermedizin |
| 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 |
| US4668680A (en) * | 1985-12-12 | 1987-05-26 | Warner-Lambert Company | 5-amino-6,8-difluoroquinolones as antibacterial agents |
| US4687770A (en) * | 1985-12-23 | 1987-08-18 | Abbott Laboratories | Isoxazolo-pyrido-benzoxazine and isothiazolo-pyrido-benzoxazine derivatives |
| US4689325A (en) * | 1985-12-23 | 1987-08-25 | Abbott Laboratories | Isoxazolo-pyrido-phenoxazine and isothiazolo-pyrido-phenoxazine derivatives |
| US4772706A (en) * | 1986-01-13 | 1988-09-20 | Warner-Lambert Company | Process for quinoline-3-carboxylic acid antibacterial agents |
| JPS62246541A (ja) * | 1986-01-20 | 1987-10-27 | Kyorin Pharmaceut Co Ltd | ベンゾイル酢酸エステル誘導体とその製造方法 |
| DE3705621C2 (de) * | 1986-02-25 | 1997-01-09 | Otsuka Pharma Co Ltd | Heterocyclisch substituierte Chinoloncarbonsäurederivate |
| JPS62215572A (ja) * | 1986-03-17 | 1987-09-22 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体 |
| JPS63198664A (ja) * | 1986-03-31 | 1988-08-17 | Sankyo Co Ltd | キノロンカルボン酸誘導体 |
| DE3641312A1 (de) * | 1986-12-03 | 1988-06-09 | Bayer Ag | Verfahren zur herstellung von chinolincarbonsaeuren |
| HU198709B (en) * | 1987-04-08 | 1989-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing quinoline-carboxylic acid derivatives |
| US5563138A (en) * | 1987-04-16 | 1996-10-08 | Otsuka Pharmaceutical Company, Limited | Benzoheterocyclic compounds |
| DE3713672A1 (de) * | 1987-04-24 | 1988-11-17 | Bayer Ag | Verfahren zur herstellung von parenteral verabreichbaren chinoloncarbonsaeuren |
| JP2556330B2 (ja) * | 1987-07-09 | 1996-11-20 | 杏林製薬株式会社 | アニソ−ル誘導体並びにその製造方法 |
| DE3724466A1 (de) * | 1987-07-24 | 1989-02-02 | Bayer Ag | Verfahren zur herstellung von chinoloncarbonsaeuren |
| IL88003A (en) * | 1987-10-16 | 1992-11-15 | Dainippon Pharmaceutical Co | Quinoline derivatives,their preparation and pharmaceutical compositions containing them |
| US5164392A (en) * | 1987-10-16 | 1992-11-17 | Dainippon Pharmaceutical Co., Ltd. | Quinoline derivatives and antibacterial agent containing them |
| EP0342849A3 (en) * | 1988-05-19 | 1990-03-14 | Pfizer Inc. | Intermediates for preparing 1,4-dihydro-4-oxo-quinoline-3-carboxylic acid esters |
| KR910003630B1 (ko) * | 1988-06-17 | 1991-06-07 | 한국과학기술원 | 벤조일 아세틱 에스테르 유도체 및 그 제조방법 |
| GR1000201B (el) * | 1988-06-23 | 1992-03-20 | Tsetis Kleon | Mέ?οδος για την παρασκευή του 1-κυκλοπροπυλο-6-φ?ορο-1,4-διϋδρο-4-οξο-7κινολίνο-3-καρβοξυλικού οξέος δομικού λί?ου παρασκευής των 1-κυκλοπρόπυλο-6-φ?όρο-1,4-διϋδρο-4οξο-7-πιπεράζινο-κινολινο 3καρβοξυλικών οξέων. |
| FI95130C (fi) * | 1988-07-20 | 1995-12-27 | Sankyo Co | Menetelmä lääkeaineena käyttökelpoisten 4-oksokinoliini-3-karboksyylihapon johdannaisten valmistamiseksi |
| US5262417A (en) * | 1988-12-06 | 1993-11-16 | The Upjohn Company | Antibacterial quinolone compounds |
| US5219781A (en) * | 1988-12-08 | 1993-06-15 | Mitsubishi Denki Kabushiki Kaisha | Method for manufacturing semiconductor memory device having a stacked type capacitor |
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| JP2944759B2 (ja) * | 1995-05-24 | 1999-09-06 | アルコン ラボラトリーズ，インコーポレイテッド | 抗菌性組成物 |
| DE19547635A1 (de) * | 1995-12-20 | 1997-06-26 | Bayer Ag | Verfahren zur Herstellung von Cyclopropancarbonsäureamiden |
| DE1135132T1 (de) | 1998-12-04 | 2002-08-22 | Influx, Inc. | Inhibitoren des multidrogentransportes |
| AU6868700A (en) | 1999-09-02 | 2001-04-10 | Wakunaga Pharmaceutical Co., Ltd | Quinolinecarboxylic acid derivative or its salt |
| SE9904108D0 (sv) | 1999-11-15 | 1999-11-15 | New Pharma Research Ab | Nya föreningar |
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| DE102007004732A1 (de) * | 2007-01-31 | 2008-08-07 | Bayer Healthcare Ag | Enrofloxacin-Hexahydrat |
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| WO2017217441A1 (ja) | 2016-06-15 | 2017-12-21 | 湧永製薬株式会社 | 新規ピリドンカルボン酸誘導体又はその塩 |
| CN113912539B (zh) * | 2021-12-13 | 2022-03-11 | 山东国邦药业有限公司 | 一种环丙羧酸的合成方法 |
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| JPS5188973A (ja) * | 1975-01-29 | 1976-08-04 | Shinkinakinoronkarubonsanjudotainoseiho | |
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| CA1175836A (en) * | 1977-09-20 | 1984-10-09 | Marcel Pesson | Production of 1,4-dihydroquinoline-3-carboxylic acid derivatives |
| JPS5466686A (en) * | 1977-09-20 | 1979-05-29 | Dainippon Pharmaceut Co Ltd | Quinoline-3-carboxylic acid derivative, its preparation, and pharmaceutical composition containig the same |
| DE2808070A1 (de) * | 1978-02-24 | 1979-08-30 | Bayer Ag | Verfahren zur herstellung von 4-pyridon-3-carbonsaeuren und/oder deren derivaten |
| 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 |
| JPS5762259A (en) * | 1980-09-05 | 1982-04-15 | Kyorin Pharmaceut Co Ltd | Preparation of substituted quinolinecarboxylic acid derivative |
| IE52125B1 (en) * | 1980-10-02 | 1987-06-24 | Fox Charles L Jun | 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quino-line carboxylic acid and metal salts thereof useful in burn therapy |
| US4788320A (en) * | 1986-01-20 | 1988-11-29 | Kyorin Pharmaceutical Co., Ltd. | Benzoylacetic acid ester derivatives and process for their preparations |
| US4689423A (en) * | 1986-04-01 | 1987-08-25 | Warner-Lambert Company | Process for the preparation of 2,3,4,5-tetrafluorobenzoyl acetates |
| JPS6356224A (ja) * | 1986-08-27 | 1988-03-10 | 株式会社クボタ | マルチ作業機の覆土装置 |
| CA2017090A1 (en) * | 1990-05-17 | 1991-11-17 | Stephen Dunn | Coating composition |
-
1981
- 1981-10-29 DE DE19813142854 patent/DE3142854A1/de not_active Withdrawn
-
1982
- 1982-07-01 IE IE1606/82A patent/IE53709B1/en not_active IP Right Cessation
- 1982-07-05 NO NO822346A patent/NO158018C/no not_active IP Right Cessation
- 1982-07-06 IL IL66243A patent/IL66243A/xx not_active IP Right Cessation
- 1982-07-07 ZA ZA824829A patent/ZA824829B/xx unknown
- 1982-07-07 DK DK306082A patent/DK160491C/da not_active IP Right Cessation
- 1982-07-08 FI FI822442A patent/FI78689C/fi not_active IP Right Cessation
- 1982-07-09 AU AU85768/82A patent/AU561103B2/en not_active Expired
- 1982-07-16 DD DD82241728A patent/DD202560A5/de unknown
- 1982-07-19 AT AT82106472T patent/ATE23040T1/de not_active IP Right Cessation
- 1982-07-19 EP EP82106472A patent/EP0078362B1/de not_active Expired
- 1982-07-19 DE DE8282106472T patent/DE3273892D1/de not_active Expired
- 1982-07-19 KR KR8203203A patent/KR870000895B1/ko not_active Expired
- 1982-07-29 JP JP57131346A patent/JPS5874667A/ja active Granted
- 1982-08-13 CA CA000409435A patent/CA1218067A/en not_active Expired
- 1982-10-25 GR GR69612A patent/GR77707B/el unknown
- 1982-10-26 NZ NZ202278A patent/NZ202278A/en unknown
- 1982-10-28 HU HU823457A patent/HU187580B/hu unknown
- 1982-10-28 ES ES516921A patent/ES516921A0/es active Granted
- 1982-10-28 PH PH28052A patent/PH18803A/en unknown
-
1987
- 1987-04-09 AU AU71406/87A patent/AU573126B2/en not_active Expired
- 1987-04-09 AU AU71405/87A patent/AU573125B2/en not_active Expired
- 1987-05-25 JP JP62127876A patent/JPS6322075A/ja active Granted
- 1987-05-25 JP JP62127878A patent/JPS6322057A/ja active Granted
- 1987-05-25 JP JP62127877A patent/JPS6322076A/ja active Granted
-
1990
- 1990-08-10 DK DK190890A patent/DK162637C/da not_active IP Right Cessation
-
1991
- 1991-05-27 JP JP3151073A patent/JPH0824536B2/ja not_active Expired - Lifetime
-
1993
- 1993-06-24 LU LU88325C patent/LU88325I2/fr unknown
-
1994
- 1994-12-30 NO NO1994030C patent/NO1994030I1/no unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013157018A1 (en) | 2012-04-18 | 2013-10-24 | Indian Institute Of Technology Madras | A process for the preparation of the core structure in quinolone and napthyridone class of antibiotics |
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