CYCLOHEXANE TETROL ESTERS AND THEIR PREPARATION

摘要

1481966 Cyclohexanetetrol esters and their preparation E R SQUIBB & SONS Inc 22 July 1974 [30 July 1973] 32382/74 Heading C2C Novel compounds of the formula or physiologically acceptable addition salts thereof, wherein Y is a radical of the formula -C n H 2n -NR5R6 or of the formula in which n is 1-6, m is 0 or 1 and R5 and R6, which may be the same or different, are hydrogen, alkyl, aralkyl or dialkylaminoalkyl, or R5 and R6 together with the nitrogen atom to which they are attached are pyrrolidino, piperidino or N1-alkyl piperazino, R1, R2, R3 and R4, which may be the same or different, are alkanoyl, haloalkanoyl, 2-, 3- or 4-pyridylcarbonyl, alkenoyl, aroyl, or alkoxycarbonyl of the formula -COR where R is alkyl or an aminoalkanoyl radical of the formula -CO-C p H 2p -NR5R6 where p is 0.3, R7 and R8, which may be the same or different, are hydrogen or alkyl, or R7 and R8 taken together with the carbon atoms bearing substituents 0R1 and OR3 form a cycloalkyl ring, and R9 is hydrogen or a C 1-6 alkyl radical, may be obtained (a) by esterifying a tetrol of the formula in the presence of a strong acid the anion of which does not open an epoxide ring, or (b) by treating a substituted cyclohexadiene of the formula with an acid, the anion of which does not open an epoxide ring, treating the resulting salt with at least 2 equivalents of a peracid, and treating the resulting compound with an acid anhydride in the presence of a strong acid, the anion of which does not open an epoxide ring. The diene starting material may be prepared by the Birch reduction of the corresponding aromatic compound and subsequently converted to the tetrol derivative by reaction with H 2 O 2 and formic acid. The products possess blood pressure lowering properties and may be formulated in a conventional manner.