GB1074082A - Dibenzocycloheptene compounds - Google Patents

Abstract

The invention comprises compounds of the formulae I, II, III, IV and V wherein each of R and R1 represents a C1- 6 alkyl radical or R and R1 are joined to represent, together with the N atom to which they are attached, a 1-piperidyl, 1 - pyrrolidinyl, 1 - morpholinyl or 1 - (C1- 4 alkyl) - 4 - piperazinyl ring, each of X and X1 represents a hydrogen or halogen atom or a C1- 6 alkyl, C2- 6 alkenyl, trifluoromethyl, hydroxyl, C1- 4 alkoxy, mercapto, C1- 4 alkylmercapto, C1- 4 alkylsulphonyl, sulphamoyl, C1- 4 alkylsulphamoyl or C2- 8 dialkylsulphamoyl radical, Ac represents an acyl radical and each of R11 and R111 represents a hydrogen atom or an alkyl, aryl or aralkyl group, and non-toxic salts of compounds of the Formulae I and II; the process wherein compounds of Formulae VI or VII are reacted with a Grignard reagent of the Formula HalMgCH2CH2CH2 NRR1, where Hal represents a halogen atom, the Grignard adducts hydrolysed and the resulting 5 - hydroxy - 5 - (3 - tertiary aminopropyl) derivatives dehydrated to give compounds of the Formulae III or V respectively which may be hydrolysed to give a compound of the Formula I; the preparation of compounds of the Formula I by treating compounds of the Formula VIII with osmium tetroxide in a dry, inert solvent and hydrolysing the resulting osmic esters; the preparation of compounds of the Formula II by reacting a compound of the Formula III or a compound of the Formula V, wherein each of R and R1 represents a C1- 6 alky radical, with a haloformate and hydrolysing the resulting urethane, or by reacting a compound of the Formula III, wherein each of R and R1 represents a C1- 6 alkyl group, with a cyanogen halide and hydrolysing the resulting product. <FORM:1074082/C2/1> <FORM:1074082/C2/2> <FORM:1074082/C2/3> <FORM:1074082/C2/4> <FORM:1074082/C2/5> <FORM:1074082/C2/6> <FORM:1074082/C2/7> <FORM:1074082/C2/8> Compounds of the Formula IV may be prepared by reacting a compound of the Formula III, wherein each of R and R1 represents a C1- 6 alkyl radical, with a haloformate or cyanogen halide and hydrolysing the resultant product in a basic medium. Therapeutic compositions with anti-depressant properties, in the forms of tablets, powders, sustained release pellets, solutions or suspensions for oral and parenteral application, comprise compounds of the Formulae I and II or their non-toxic salts, or compounds of the Formulae III, IV and V, with an inert pharmaceutical diluent, carrier or coating.