NEW CYCLOALKANOQUINOLONE DERIVATIVES AND THE PREPARATION TNEW CYCLOALKANOQUINOLONE DERIVATIVES AND THE PREPARATION THEREOF HEREOF

1351585 Cycloalkanoquinolones BOEHRINGER MANNHEIM GmbH 17 Jan 1973 [21 Jan 1972] 2422/73 Addition to 1210638 Heading C2C Novel compounds of general Formula I wherein one of R 1 and R 2 is hydrogen and the other, together with R 3 forms an aliphatic bridge of 3 to 5 carbon atoms and X is a chlorine, hydroxy, acetoxy or α-chloroacetoxy group, and pharmacologically compatible salts thereof may be prepared by reacting a compound of general Formula II wherein Y is OH or alkoxy with a compound of formula X-CH 2 CH 2 CH 2 Z in which X is as defined above and Z is a halogen atom or a sulphonic acid radical and, if the product contains an esterified 3 carboxy group, hydrolysing under basic conditions to liberate the carboxy group and, if desired, chemically changing the substitutent X, within the scope of the above definition, in known manner, or forming a salt by reaction with a pharmacologially acceptable base. 1 - [γ - hydroxypropyl] - 1,4 - dihydro - 3- carboxycyclopentano-(h)-quinolene-(4) is prepared by reaction of 3-carbethoxy-4-hydroxyoyolopentano(h)quinoline with 3-ehloropropan-1-ol in the presence of K 2 CO 3 and KI, and is reacted first with p-toluene sulphonic acid chloride to form 1 - [γ - tosylpropyl] - 1,4 - dihydro - 3- carboxycyclopentano(h)quinolinone-(4) which is further reacted with hydrogen chloride to form the 1 - [γ - chloropropyl)-1,4 - dihydro - 3- carboxycyclopentano(h)quinolinone-(4). 1-[γ-Acetoxypropyl]- and 1-[γ-chloroacetoxypropyl] - 1,4 - dihydro - 3 - carboxycyclopentano- (h)quinolinone-(4) are prepared by reaction of the corresponding γ-hydroxypropyl compound with acetyl chloride and chloroacetyl chloride respectively. Pharmaceutical compositions having antimicrobial activity for enteral or parenteral administration comprise a compound of Formula I or pharmacologically acceptable salt thereof together with a solid or liquid pharmaceutical diluent or carrier.