86483-50-3

The invention relates to 7-amino-1-cyclo-propyl-4-oxo-1, 4-dihydro-naphthyridine (or quinoline)-3-carboxylic acids of Formula I as defined in the specification. Also included in the invention is a process for the preparation of said compounds of Formula I and Ia. Further, the invention includes compositions containing the compounds of Formula I or Ia and the use of said compounds and compositions as antibacterial agents.

Starting with o-halobenzoyl chlorides 4 and open-chain secondary enamines 5, a new synthesis of 4-quinolone-3-carboxylic acids 12 is described.The reaction of 7-haloquinolone-3-carboxylic acids 12a-k with aliphatic amines 14 produces highly active antibacterial 7-aminoquinolone-3-carboxylic acids 15.The main product of the 1-cyclopropyl series, "ciprofloxacin" (15a), is being developed as a broad-spectrum chemotherapeutic agent.

A method of combating plant-pathogenic bacteria, comprising applying to the bacteria or to a bacteria habitat a bactericidally effective amount of a cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid derivative of the formula STR1 in which A represents straight-chain or branched alkylene with 1 to 6 carbon atoms or a >C=CH-- radical, R1 represents alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, carboxyl, optionally substituted carbamoyl, cyano or dialkoxyphosphonyl or alkylsulphonyl with 1 to 4 carbon atoms in the alkyl part, and R2 represents hydrogen, alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, optionally substituted carbamoyl, cyano, chlorine, acetyl, alkyl with 1 to 3 carbon atoms or phenyl, or R1 and R2, together with the carbon atom which they substitute, can also form a 2-oxo-tetrahydrofuryl ring, R3, R4, R5 and R6 can be identical or different and represent hydrogen, methyl, ethyl or n- or i-propyl and X represents hydrogen, halogen or nitro, or an acid addition salt, alkali metal salt, alkaline earth metal salt, heavy metal salt or hydrate thereof. The heavy metal salts are new.

The invention relates to 7-amino-1-cyclo-propyl-4-oxo-1,4-dihydro-naphthyridine (or quinoline)-3-carboxylic acids of Formula I as defined in the specifications. Also included in the invention is a process for the preparation of said compounds of Formula I and Ia. Further, the invention includes compositions containing the compounds of Formula I or Ia and the use of said compounds and compositions as antibacterial agents.

Combating microorganisms, particularly in agriculture, with a 1-cyclopropyl-1,4-dihydro-4-oxo-quinolinecarboxylic acid of the formula STR1 in which R1 is hydrogen, fluorine, chlorine, bromine or nitro, R2 is hydrogen, chlorine, fluorine or the group STR2 particularly a 4-piperazinyl radical, or an acid addition, alkali metal, alkaline earth metal or heavy metal salt thereof which is tolerated by plants, or a hydrate thereof. Some of the compounds are known.

The invention relates to 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(alkyl-1-piperazinyl)quinoline-3-carboxylic acids of Formula (I), processes for their manufacture, compositions containing them and use of said compounds and compositions as antibacterial and/or feedstuff additives.

The invention relates to quinolone carboxylic acids, pharmaceutical compositions containing said quinolone carboxylic acids and the use of said compounds and compositions for treatment of bacterial infection. Also included in the invention are process for the manufacture of the active quinolone carboxylic acids.

The invention relates to quinolone carboxylic acids of the formula (I) as defined herein, pharmaceutical compositions containing said quinolone carboxylic acids and the use of said compounds and compositions for treatment of bacterial infection. Also included in the invention are process for the manufacture of the active quinolone carboxylic acids.