GB932965A - Cyclohexane and cyclohexene dicarbamates and therapeutic compositions containing them - Google Patents

Abstract

The invention comprises dicarbamates having the general formulae I and II <FORM:0932965/IV(a)/1> <FORM:0932965/IV(a)/2> wherein R1 is hydrogen or methyl and R2 is C1-3 alkyl, and includes also compounds of the above formulae containing additionally a methyl group substituted in the cyclohexane or cyclohexene rings; several processes for preparing these compounds; and therapeutic compositions containing the carbamates. In the examples: (1) 1,1-bis-(hydroxymethyl)- cyclohexane di-(N-methylcarbamate) is prepared from the corresponding diol by reacting first with phosgene to give the dichloroformate which is then reacted with methylamine; (2) the compound of formula III <FORM:0932965/IV(a)/3> is prepared by reacting the corresponding diol with diethyl carbonate to give the cyclic carbonate, which is reacted with ispropylamine and the mono-isopropyl carbamate thus obtained reacted with (a) phosgene then (b) ammonia; (3) and (4) compounds of formulae IV <FORM:0932965/IV(a)/4> and V <FORM:0932965/IV(a)/5> are prepared by reactions analogous to those in Example (2), the starting material for (4) being obtained from the starting material for (3) by hydrogenation. In another procedure, the bis-hydroxymethyl-cyclohexane or -cyclohexene may be reacted directly with N-methyl substituted urethane in the presence of a catalyst such as aluminium isopropoxide. According to the second Provisional Specifications, 4,4-bis(hydroxymethyl)- 5-methylcyclohexene is prepared from crotonaldehyde, butadiene and formaldehyde, and hydrogenated to yield 1,1-bis-(hydroxymethyl)-2-methylcyclohexane. According to the same Provisional Specification, the dicarbamates may contain up to three methyl substituents and/or a methylene bridge in or across the cyclohexane or cyclohexene rings, and R1 may be C1-3 alkyl. The above dicarbamates may be combined with solid diluents such as starch, gelatin, magnesium stearate or alginic acid in the form of tablets, pills or capsules, or dissolved in an alcohol or glycol to make an injectable solution; the resulting therapeutic compositions have anti-convulsant and tranquillising properties.