GB1010572A - Dibenzocycloheptene derivatives - Google Patents

Abstract

The invention comprises dibenzocycloheptene derivatives of the formula <FORM:1010572/C2/1> wherein Z is an ethylene group -CH2CH2- or vinylene group -CH = CH-, R1 and R2 are hydrogen, halogen, e.g. Cl, or C1- 3 alkyl groups R3 is hydrogen, C1- 3 alkyl, e.g. CH3, or aralkyl, e.g. benzyl and R4 is hydrogen, or R3 and R4 together form an alkylene chain of 4 or 5 carbon atoms and Y is hydrogen or a C1- 3 alkyl group, and their preparation by reacting the corresponding carboxylic halide with ammonia or an amine HNR3R4, or in the case where R3 and R4 are both hydrogen, by partially hydrolysing the corresponding nitrile. 5 - Cyano - dibenzocyclohepta - dienes and -trienes are made by reacting the appropriate 5 - chloro - dibenzocycloheptene with a heavy metal cyanide, e.g. silver cyanide. If required, a 5-cyano compound wherein Z = -CH2CH2-may be brominated followed by dehydro-bromination of the resulting bromo compound to give a compound wherein Z is -CH = CH-. 5 - Alkyl - 5 - cyano compounds, i.e. derivatives wherein Y is an alkyl group such as CH3, are made by alkylation of the above compounds in the presence of an alkali-metal amide. Dibenzocyclohepta - diene- and -triene - 5 - carboxylic halides are made by hydrolysing the corresponding nitrile with aqueous sulphuric acid and treating the resulting 5-carboxylic acid with a halogenating agent such as a thionyl or phosphorus halide. The 5-carboxylic acids may also be made by treating the corresponding hydrocarbon with potassium amide or a sodium-naphthalene complex in tetrahydrofuran and reacting the resulting 5-metallo-compound compound with carbon dioxide. 3 - Chloro - dibenzo(a,e)(1,3,5) - cycloheptatrien-5-ol is made by reducing the corresponding 5-ketone with lithium aluminium hydride. 5 - Chlorodibenzo(a,d)(1,4) - cycloheptadiene is made by the action of thionyl chloride or gaseous hydrogen chloride on the 5-hydroxy-dibenzocycloheptadiene. Pharmaceutical preparations active as anti-convulsant agents in pentylenetetrazole or electro-shock therapy, comprise the above compounds of the invention in association with a carrier suitable for administration orally (e.g. as tablets or capsules) or by injection.