Substituted triphenyl-carbinols and a process for the manufacture thereof

摘要

The invention comprises substituted triphenyl carbinols of the general formula: wherein n is a whole number of from 1 to 7, D is a dialkylamino group in which the alkyl groups may be joined (directly or through an oxygen sulphur or nitrogen atom) to form a five or six membered ring, each R is an optional alkyl, alkylsulphonyl, alkylthio, alkoxy, dialkylamino group in which the alkyl group or each of the alkyl groups contain up to four carbon atoms or a hydroxy, esterified hydroxy, halogeno or D-(CH2)n-O-group (D and n having the aforementioned significance) and the broken lines denote bonds leading to optional groups, salts thereof, pharmaceutical compositions thereof, and a process for the manufacture thereof by condensing in a Grignard or alkali-metal reaction either a substituted or unsubstituted benzoic acid ester in which the substitution if any consists of one or two of the groups R (except that any hydroxyl groups must be protected) or a substituted or unsubstituted benzophenone in which the substitution if any consists of one or two groups R in one or both nuclei, with a substituted or unsubstituted phenyl halide in which the substitution consists of one or two of the groups R, at least one of the nuclei present in the starting materials containing the group D-(CH2)n-O- in the p-position as set forth above as its substituent or one of its substituents, hydrolysing the condensation product, esterifying any hydroxy group or groups present in the hydrolysis product if desired, and, also if desired, converting the product into a salt. The phenyl groups of the starting compounds may be substituted by up to five of the groups methyl, ethyl isopropyl, methyl sulphonyl, ethylsulphonyl, methyl mercapto, ethyl mercapto, methoxy, ethoxy, dimethylamino, diethylamino, acetoxy or propionoxy and the N,N-disubstituted amino alkoxy substitution in the starting compounds may be N,N-disubstituted-aminoethoxy or N,N-disubstituted aminopropoxy or both. p-Hydroxy-p1-methyl-benzophenone is obtained by warming paratoluic acid phenyl ester in nitrobenzene with aluminium chloride and hydrolysing. p-Morpholinoethoxyp1-methyl-benzophen one is obtained by reacting p-hydroxy-p1methyl-benzophenone with morpholino ethyl chloride. By a similar procedure there may be obtained p-piperidinoethoxy-p1-methyl benzophenone, pdiethylaminoethoxyp1-methoxybenzophenone, p-dimethylamino-ethoxyp1-methoxybenzophenone, p,p1-bisdiethylaminoethoxy benzophenone and p-diethylamino-propoxyp1-methyl-benzophenone. Pharmaceutical preparations containing the compounds of the formula above, and having cholesterol lowering activity are administered enterally or parenterally as tablets, troches, suppositories, capsules, solutions, suspensions or emulsions.