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GB830832A - New quinolones and therapeutic compositions containing them - Google Patents

New quinolones and therapeutic compositions containing them

Info

Publication number
GB830832A
GB830832A GB5201/57A GB520157A GB830832A GB 830832 A GB830832 A GB 830832A GB 5201/57 A GB5201/57 A GB 5201/57A GB 520157 A GB520157 A GB 520157A GB 830832 A GB830832 A GB 830832A
Authority
GB
United Kingdom
Prior art keywords
alkyl
quinolones
nitro
carboxy
alkenyl
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
Application number
GB5201/57A
Inventor
Norman Barton
Albert Frederick Crowther
Walter Hepworth
Dora Nellie Richardson
George William Driver
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB5201/57A priority Critical patent/GB830832A/en
Publication of GB830832A publication Critical patent/GB830832A/en
Expired legal-status Critical Current

Links

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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises quinolones (excepting 1-methyl-6-nitro-4-quinolone-3-carboxylic acid and its sodium salt) of the general formula <FORM:0830832/IV (b)/1> (wherein A is a benzene ring bearing one or more substituents, e.g. phenyl, alkyl, trifluormethyl, alkoxy, hydroxy, cyano, nitro, halogen, and acyl, R is alkyl or alkenyl, which may be substituted, R1 is hydrogen or an alkyl radical, and R2 is a carboxy group or a derivative or precursor thereof, viz. salts, esters (e.g. alkyl, cyclohexyl, b -diethylaminoethyl, b -chloroethyl or phenyl esters), thiolesters, the corresponding carbinol and its ethers and esters, formyl, nitrile, and radicals of formula -COR3, where R3 is a hydrocarbon radical, optionally substituted, e.g. by an alkoxycarbonyl group); also processes for their preparation (a) by alkylating (or alkenylating) 4-hydroxy-quinolines of the general formula <FORM:0830832/IV (b)/2> (b) by esterifying quinolones in which R2 is a carboxy group or an esterifying carboxy derivative with an alcohol, thiol or phenol; (c) by acylating quinolones, containing a hydroxy group, e.g. -CH2OH in position 3; (d) by oxidizing quinolones wherein R2 is -CH2OH to the corresponding 3-formyl or 3-carboxy compounds, e.g. with potassium permanganate; (e) by reducing compounds wherein R is alkenyl to give the analogous alkyl compounds; (f) by nitrating quinolones unsubstituted in the 6-position to give the 6-nitro derivatives. 80 detailed examples are given.ALSO:Compositions for the control and treatment of bacterial infections, e.g. Salmonella dublin, comprise quinolones of the general formula <FORM:0830832/VI/1> (other than 1 - methyl - 6 - nitro - 4 - quinolone-3-carboxylic acid and its sodium salt) wherein R is alkyl or alkenyl (optionally substituted), R1 is H or alkyl, R2 is a carboxy group or a derivative or precursor thereof, A is a benzene ring which may be substituted, together with a pharmaceutical carrier or diluent, and optionally another active ingredient, e.g. aureomycin hydrochloride, the calcium salt of phenoxymethylpenicillin and 2-p-aminobenzenesulphonamino - 4 : 6 - dimethylpyrimidine. The compositions may take the form of aqueous and non-aqueous suspensions, dispersible powders, creams, ointments, tablets, pills and pessaries.
GB5201/57A 1957-02-15 1957-02-15 New quinolones and therapeutic compositions containing them Expired GB830832A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB5201/57A GB830832A (en) 1957-02-15 1957-02-15 New quinolones and therapeutic compositions containing them

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5201/57A GB830832A (en) 1957-02-15 1957-02-15 New quinolones and therapeutic compositions containing them

Publications (1)

Publication Number Publication Date
GB830832A true GB830832A (en) 1960-03-23

Family

ID=9791620

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5201/57A Expired GB830832A (en) 1957-02-15 1957-02-15 New quinolones and therapeutic compositions containing them

Country Status (1)

Country Link
GB (1) GB830832A (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3472859A (en) * 1966-11-01 1969-10-14 Sterling Drug Inc 1-alkyl-1,4-dihydro-4-oxo-3 quinoline-carboxylic acids and esters
FR2085701A1 (en) * 1970-03-13 1971-12-31 Boehringer Mannheim Gmbh
DE2224090A1 (en) * 1971-05-17 1972-11-30 Sterling Drug Inc., New York, N.Y. (V.St.A.) Substituted quinoline carboxylic acids and esters and processes for their preparation
FR2228488A1 (en) * 1973-05-11 1974-12-06 Ciba Geigy Ag
US4146625A (en) 1976-07-16 1979-03-27 E. I. Du Pont De Nemours And Company Quinolonecarboxylic acids for control of bacterial diseases in plants
EP0028698A1 (en) * 1979-10-05 1981-05-20 Tanabe Seiyaku Co., Ltd. Quinoline compounds, process for their preparation, and pharmaceutical compositions
EP0062001A2 (en) * 1981-03-24 1982-10-06 Ciba-Geigy Ag Acyl quinolinone derivatives, processes for their preparation, pharmaceutical compositions containing them and their use
US4390541A (en) 1980-12-19 1983-06-28 Lilly Industries Limited Quinolone derivatives and their use in a method of controlling an immediate hypersensitivity disease
US4544747A (en) * 1979-02-26 1985-10-01 Otsuka Pharmaceutical Company, Limited Quinoline carboxylic acid derivatives
EP0179239A2 (en) * 1984-09-17 1986-04-30 Sterling Drug Inc. 7-(Pyridinyl)-/-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid having antibacterial activity and preparation thereof
US4780468A (en) * 1987-08-07 1988-10-25 Warner-Lambert Company 8-trifluoromethyl quinolones as antibacterial agents
US4782156A (en) * 1984-07-18 1988-11-01 Bayer Aktiengesellschaft Nitriles of halogenated quinolonecarboxylic acids

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3472859A (en) * 1966-11-01 1969-10-14 Sterling Drug Inc 1-alkyl-1,4-dihydro-4-oxo-3 quinoline-carboxylic acids and esters
FR2085701A1 (en) * 1970-03-13 1971-12-31 Boehringer Mannheim Gmbh
DE2224090A1 (en) * 1971-05-17 1972-11-30 Sterling Drug Inc., New York, N.Y. (V.St.A.) Substituted quinoline carboxylic acids and esters and processes for their preparation
FR2228488A1 (en) * 1973-05-11 1974-12-06 Ciba Geigy Ag
US3960868A (en) * 1973-05-11 1976-06-01 Ciba-Geigy Corporation Derivatives of 6,7 or 8 cycloalkyl 4-oxo quinoline 3 carboxylic acid
US4146625A (en) 1976-07-16 1979-03-27 E. I. Du Pont De Nemours And Company Quinolonecarboxylic acids for control of bacterial diseases in plants
US4544747A (en) * 1979-02-26 1985-10-01 Otsuka Pharmaceutical Company, Limited Quinoline carboxylic acid derivatives
EP0028698A1 (en) * 1979-10-05 1981-05-20 Tanabe Seiyaku Co., Ltd. Quinoline compounds, process for their preparation, and pharmaceutical compositions
US4327101A (en) 1979-10-05 1982-04-27 Tanabe Seikaku Co., Ltd. Quinoline compound useful as antibacterial agents in warm-blooded animals
US4390541A (en) 1980-12-19 1983-06-28 Lilly Industries Limited Quinolone derivatives and their use in a method of controlling an immediate hypersensitivity disease
EP0062001A2 (en) * 1981-03-24 1982-10-06 Ciba-Geigy Ag Acyl quinolinone derivatives, processes for their preparation, pharmaceutical compositions containing them and their use
US4476132A (en) * 1981-03-24 1984-10-09 Ciba-Geigy Corporation Acylquinolinone derivatives, and antiallergic preparations and methods of inhibiting allergic reactions using them
EP0062001B1 (en) * 1981-03-24 1987-05-27 Ciba-Geigy Ag Acyl quinolinone derivatives, processes for their preparation, pharmaceutical compositions containing them and their use
US4782156A (en) * 1984-07-18 1988-11-01 Bayer Aktiengesellschaft Nitriles of halogenated quinolonecarboxylic acids
EP0179239A2 (en) * 1984-09-17 1986-04-30 Sterling Drug Inc. 7-(Pyridinyl)-/-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid having antibacterial activity and preparation thereof
EP0179239A3 (en) * 1984-09-17 1986-08-13 Sterling Drug Inc. 7-(pyridinyl)-/-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid having antibacterial activity and preparation thereof
US4780468A (en) * 1987-08-07 1988-10-25 Warner-Lambert Company 8-trifluoromethyl quinolones as antibacterial agents

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