GB969518A - Tetrahydrodibenzocyclo-octene derivatives - Google Patents

Abstract

The invention comprises tetrahydrodibenzo [a, d] cyclooctene derivatives of the general formula <FORM:0969518/C1/1> (wherein A represents an alkylene group containing 2 to 6 carbon atoms, B represents an alkylamino or dialkylamino group, on a saturated mononuclear 5- or 6-membered heterocyclic group attached to A through a nitrogen atom, which heterocyclic group may carry alkyl substituents and-when alkyl substituted-contains at most 12 carbon atoms, or A and B taken together represent a 3-tropanyl or 3-pseudo-tropanyl radical, the word "alkyl" being defined as an alkyl group containing at most 6 carbon atoms) and their acid addition salts, by heating a compound of formula <FORM:0969518/C1/2> with a compound of formula Y-A-B, wherein one of X and Y represents a halogen atom and the other an -O-alkali metal group, or X represents a halogen atom or hydroxyl group and Y represents a hydroxyl group, preferably (when X=halogen and Y=OH) in the presence of an acid-binding agent or (when X=Y=OH), a dehydrating agent. The starting materials may be prepared as follows:- The g -lactone of 2-(1-hydroxy -3- phenylpropyl) benzoic acid (prepared by condensing o-carboxy-acetophenone with benzaldehyde and hydrogenating the resulting 2-cinnamoylbenzoic acid) is reacted with red phosphorus and HI to give 2-(3-phenylpropyl)-benzoic acid which is cyclised to 5, 10, 11, 12-tetrahydrodibenzo [a, d] cycloocten -5- one by direct treatment with P2O5 or first converted to the acid chloride which is then cyclised using AlCl3. The ketone is reduced using LiAlH4 to give 5, 10, 11, 12-tetrahydrodibenzo [a, d] cyclo-octen-5- ol which may be converted to the corresponding halide or to its alkali metal derivative. Pharmaceutical preparations comprise the compounds of the invention in association with a pharmacologically acceptable carrier. They have antiallergic, anticholinergic, psychotropic and analgesic activity, and may take the form of tablets, pills, capsules, solutions, suspensions, emulsions, syrups or elixirs.