Patent ID: 6333433
Filing Date: 2001-12-25
Classification: A61K,C07C,Y10S

Abstract:
A process for the synthesis of novel cationic amphiphiles that facilitate intracellular delivery of biologically active molecules, said amphiphiles represented by the following structural formula (I): ##STR11##wherein:n is an integer between 1 and 3;R.sub.1 independently, represents either a saturated aliphatic group or an unsaturated aliphatic group (from C.sub.8 to C.sub.20);Z represents a methylene (--CH.sub.2 --) group;R.sub.2, independently, represents a long-chain saturated alkyl group (from C.sub.7 to C.sub.19);R.sub.3 is a small allyl group (from C.sub.1 to C.sub.3);X is either a halogen atom or a tosylate group,said process comprising the steps of:(a) coupling an appropriate aliphatic saturated or unsaturated aldehyde with an alkyl amine followed by the reduction of the resulting imine to obtain the corresponding secondary amine;(b) reacting the secondary amine obtained in step (a) with the appropriate hydroxyl-protected hydroxyalkyl halide followed by removal of the hydroxyl protecting group to obtain the corresponding N-hydroxyalkyl group containing tertiary amine, and(c) quaternizing the resulting N-hydroxyalkyl group containing tertiary amine obtained in step (b) with the appropriate alkyl halide or alkyl tosylates in a mixed polar solvent.