Method of obtaining 3,3-diphenylpropylamines

Abstract

The invention relates to a method of obtaining 3,3-diphenylpropylamines (I), wherein R 1 is H, alkyl, haloalkyl or alkoxyalkyl, R 2 is alkyl, alkoxy, halogen, NO 2 , CN, CHO, which may be free or protected, CH 2 OH or COOR 6 , and R 2 and R 1 are selected independently from H and alkyl or together with the nitrogen to which they are bound form a ring having 3 to 7 members. The inventive method consists in reacting a propylenephenylamine and a disubstituted aromatic hydrocarbon and, if necessary, separating the desired enantiomer or the mixture of enantiomers, and/or converting the compound (I) into a salt. Compounds (I) are muscarinic receptor antagonists which can be used in the treatment of urinary incontinence and other symptoms of urinary bladder hyperactivity. Said compounds include tolterodine.

1 . An acid addition salt of a compound of formula (II) 
       
         
           
           
               
               
           
         
         wherein 
         R 3  and R 4  are selected independently from H and C 1 -C 8  alkyl or together with the nitrogen to which they are bound form a ring having 3 to 7 members, 
         comprising said compound of formula (II) its enantiomers or mixtures therof, or its salts, and an acid. 
       
     
     
         2 . The addition salt according to  claim 1 , wherein said acid is an organic or inorganic acid. 
     
     
         3 . The addition salt according to  claim 1 , selected from hydrochloride, hydrobromide, sulfate, methanesulfonate, phosphate, nitrate, benzoate, citrate, tartrate, fumarate or maleate of the compound of formula (II). 
     
     
         4 . The addition salt according to  claim 1 , wherein R 3  and R 4  are both isopropyl. 
     
     
         5 . The addition salt according to  claim 1 , selected from N,N-diisopropyl-3-phenyl-2-propenamine hydrochloride and N,N-diisopropyl-3-phenyl-2-propenamine hydrobromide.