Dihydroxybenzhydrylidene cycloalkanes and derivatives thereof

摘要

The invention comprises compounds of formula where R is a saturated straight or branched-chained alkylene radical of 3 to 8 carbon atoms, and R1 and R2 are similar or dissimilar and are hydrogen, alkyl radicals of 1 to 6 carbon atoms, alkenyl radicals of 2 to 6 carbon atoms, phenyl-alkyl radicals in which the alkyl radical contains 1 to 3 carbon atoms, saturated or unsaturated, straight or branched chain alkane carbonyl radicals of 1 to 18 carbon atoms which may be substituted by free carboxyl groups or carboxyl groups converted to salts, esters or amides, cyclopentane or cyclohexane carbonyl radicals, or radicals of carbonic, sulphuric or phosphoric acids. The compounds are prepared by forming a double bond by removing a compound R3-R4 from a compound of formula where R, R1 and R2 are as above and one of R3 and R4 is hydrogen and the other OH or an ester thereof. The compounds of Formula II are prepared (a) by reacting a Grignard reagent of formula where X is halogen and R6 is the same as R2 but is not hydrogen or an acid radical, with a ketone of formula where R5 is the same as R1 but is not an acid radical; (b) by reacting a p, p1-dihydroxybenzophenone or alkylated derivative thereof, with a Grignard reagent of formula where X is halogen; (c) by reacting an ester of formula where R7 is a residue of an alcohol, with a Grignard reagent of formula VI; (d) by reacting a ketone of formula with an organo-metallic compound, e.g. a lithium compound of formula Compound II is converted to Compound I by heating in a vacuum. Compounds of Formula I where R1 and R2 are alkyl groups may be hydrolysed to the dihydroxy compounds, and these may be mono- or diesterified, mono- or di-etherified, or mono-esterified and mono-etherified. Compounds esterified with polybasic acids may have the free acid radicals converted to salts, esters or amides. Examples are given. Ketones of Formula III above are prepared by reacting an acid of formula or the corresponding chloride with phenol or a phenylalkyl ether, or by oxidation of an alcohol of formula Compounds of formula where R1 and R2 are as above, are prepared by reacting phenyllithium with the corresponding compound containing a hydrogen atom in place of the lithium atom. Therapeutic compositions contain the compounds of Formula I together with sugar, starch, gelatin, magnesium stearate, emulsifying agent, corn oil, propylene glycol, polyethylene glycol and water-soluble gum. Examples are given.