Carboxyalkyl- or tetrazolyl:alkyl-hydroxyalkyl-cyclohexenone derivs.

In a process for the prodn. of new cyclohexenone derivs. of formula (I): (where R1 is H or CH3; R2 is 5-8C alkyl or p-Z-phenethyl (Z=H, F or Cl); m is 5 or 6; and Z is 1H-tetrazol-5-yl or a group -COR3 in which R3 is OH, lower alkoxy or amino), a methoxybenzene deriv. of formula (II) is reduced and (I; X=COOH) thus obtained is opt. converted into an acceptable salt by treatment with an inorganic organic base. (I) obtd. as above may be isomerised to give cpds. of formula (Ia): (I) and (Ia) have u terine-stimulant and hypotensive activity. They have a uterotonic effect in vitro at a concn. of 1-10 mg/l and on the uterus in situ at doses of 40-2000 mu g/kg. (I) and (Ia) are partic. suitable for the treatment of essential hypertension, for inducing labour, for eliminating a retained foetus, for terminating pregnancy, and for inducing menstruation. Dosage for larger mammals is 10-500 mg/day.Specific cpds. (I) include dl-4-(6-carboxyhexyl)-3-(3-hydroxyoctyl)-3-cyclohexen-1-one. In an example, this is prepared by redn. of dl-1-(6-carboxyhexyl)-2-(3-hydroxyoctyl)-4-methoxybenzene with lithium in liquid ammonia in the presence of t-butanol.