GB969028A - - Google Patents

Abstract

969,028. Tetrahydrodibenzazocine derivatives. KONINKLIJKE PHARMACEUTISCHE FABRIEKEN V/H BROCADES-STHEEMAN & PHARMACIA N.V. April 26, 1962 [April 27, 1961], No. 15360/61. Heading C2C. The invention comprises: tetrahydrodibenzazocines of the general formula: and their non-toxic acid addition salts, wherein A represents an alkylene group of up to 5 carbon atoms and B represents an alkylamino or dialkylamino group or a saturated mononuclear 5- or 6-membered heterocyclic group linked to A through a nitrogen atom, which group may carry alkyl substituents and when so substituted contains at most 12 carbon atoms ("alkyl" being defined as an alkyl group of not more than 6 carbon atoms); the preparation of these compounds by reacting a compound of the general formula: (wherein Hal represents a halogen atom) with a compound H-B; and the combination of the foregoing process with the preparation of the starting material by reacting 5,6,11,12-tetrahydrodibenz(b, f)azocine with a dihalide of the formula: preferably in the presence of an acid-binding agent. According to the Provisional Specification, 5,6,11,12-tetrahydrodibenz(b, f)azocine may be reacted directly with a compound of the formula: to produce the desired products in a single step. 5, 6, 11, 12-Tetrahydrodibenz (b, f)azocine is prepared by reacting 10, 11-dihydro -5H- dibenzo(a, d) cyclohepten -5- one with an acid addition salt of hydroxylamine and reducing (e.g. with Li Al H 4 ) the resulting oxime or the 5, 6, 11, 12-tetrahydrodibenz (b f) azocin -6- one obtained by Beckmann rearrangement thereof. (When the oxime is reduced, the Beckmann transformation takes place simultaneously). 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.