Lipids, lipid complexes and use thereof

Abstract

The present invention is related to uses of a composition comprising a pharmaceutically active component and a compound according to formula (I), wherein R 1 and R 2 are each and independently selected from the group comprising alkyl; n is any integer between 1 and 4; R 3 is an acyl selected from the group comprising lysyl, ornithyl, 2,4-diaminobutyryl, histidyl and an acyl moiety according to formula (II), wherein m is any integer from 1 to 3 and Y − is a pharmaceutically acceptable anion.

We claim: 
     
         1 . A method for the synthesis of N-palmityl-oleylamine comprising the following steps:
 providing oleic acid;   providing palmitylamine;   reacting the oleic acid and the palmitylamine to form N-palmityl-oleoylamide; and   reducing the N-palmityl-oleoylamide to N-palmityl-oleylamine,   whereby the oleic acid is at least 90% pure, whereby the percentage is the molar ratio of oleic acid and any fatty acid different from oleic acid.   
     
     
         2 . The method according to  claim 1 , wherein the oleic acid and the palmitylamine are reacted at room temperature. 
     
     
         3 . The method according to  claim 1 , wherein the oleic acid is subject to a pre-treatment prior to reacting it with the palmitylamine, whereby the pre-treatment comprises reacting the oleic acid with ethylchloroformate. 
     
     
         4 . The method according to  claim 1 , wherein the reaction is performed at 0° C. 
     
     
         5 . The method according to  claim 3 , whereby the reaction is further reacted with an acid scavenger. 
     
     
         6 . The method according to  claim 1 , whereby the molar ratio of chloroformic acid ethyl ester, oleic acid, triethylamine and palmitylamine is about 1-1.05:1:1:1-3:1-1.10. 
     
     
         7 . The method according to  claim 1 , wherein the reduction of the N-palmityl-oleoylamide to N-palmity-oleylamine is performed using LiAlH 4 . 
     
     
         8 . The method according to  claim 1 , wherein upon reacting the oleic acid with the palmitylamine, the reaction is washed, precipitated and the precipitate thus obtained optionally re-crystallised. 
     
     
         9 . The method according to  claim 5 , wherein the acid scavenger is selected from the group comprising triethylamine, diisopropylethylamine and pyridine. 
     
     
         10 . The method according to  claim 4 , wherein the reaction is performed at 0° C. under inert gas. 
     
     
         11 . The method according to  claim 3 , wherein the oleic acid is reacted with ethylchloroformate in anhydrous dichloromethane or anhydrous tetrahydrofuran.