Verfahren zur Herstellung neuer diarylsubstituierter sek. aliphatischer Amine

The invention comprises compounds of the general formula in which R is a hydrogen atom or a methyl group and non-toxic acid addition salts thereof. These compounds may be made by the following methods:-(a) by reacting a ketone of formula in which R1 and R2 are hydrogen atoms or hydroxy-protecting groups and R3 is H or an amine-protecting group, with a reducing agent, removing the protecting groups where necessary and, if desired, converting the product with an acid to an acid addition salt; or (b) by reacting a compound of formula under reducing conditions with a compound of formula The ketonic compound used as starting material in (a) above may be prepared (i) by reacting a bromoketone of formula with an amine of formula in which R4 and R5 are hydrogen or hydroxy-protecting groups and R6 is hydrogen or an amine protecting group, and where necessary converting the groups R4, R5 and R6 to hydrogen or (ii) by reacting an amine of formula.. under reducing conditions with a compound of formula The above novel hydroxy amines possess broncho-spasmolytic activity. They may be used in association with a pharmaceutical carrier or excipient and administered orally, parenterally or by the nose. For oral administration the compositions may take the form of powders, suspensions, tablets or capsules. Conventional tabletting excipients, e.g. lactose, potato and maize starches, talc, gelatin, stearic acid, silicic acid and magnesium stearate, may be used. For parenteral administration the carrier may be, for example, pyrogen-free water, an aqueous solution of polyvinylpyrrolidone or arachis oil. For administration to the nose the compositions are conveniently in the form of a drop or spray solution.