Process for obtaining norelgestromin in different relations of isomers E and Z

Abstract

The present invention is related to an oxime of the 13β-ethyl-17α-hydroxi-18,19-dinorpregn-4-en-20-in-3-o (norelgestromin) of Formula I with a relation of isomers E/Z between 1.3 and 1.6 and the method of producing the oxime.

1 - 11 . (canceled)  
     
     
         12 . An oxime of the 13β-ethyl-17α-hydroxy-18,19-dinorpregna-4-en-20-yn-3-one (norelgestromin) of Formula I, wherein the oxime of formula I includes isomers E/Z and has a purity between 99.2 to 99.8%.  
     
     
         13 . An oxime of the 13β-ethyl-17α-hydroxi-18,19-dinorpregn-4-en-20-in-3-o (norelgestromin) of Formula I with a relation of isomers E/Z between 1.4-1.6 
       
         
           
           
               
               
           
         
       
     
     
         14 . The oxime according to  claim 13  wherein the purity is 99.8%.  
     
     
         15 . The oxime of  claim 13  wherein the relation of isomers E/Z is 1.4 and having a purity of 99.2%  
       
         
           
           
               
               
           
         
       
     
     
         16 . The isomer E of norelgestromin according to  claim 15  having a purity of 96%.  
     
     
         17 . Norelgestromin with a relation of isomers E/Z between 1.3 to 1.6, when prepared according a process comprising:  
       
         
           
           
               
               
           
         
         a) producing hydroxylamine by adding an acetate salt to a hydroxylamine salt in a solvent medium;  
         b) adding levonorgestrel to the solution of step a to produce an oxime;  
         c) adding an acid to modify the acidity of the solution of step b; and  
         d) adding a base to neutralize the solution.  
       
     
     
         18 . A pharmaceutical composition comprising: 
 an oxime of the 13β-ethyl-17α-hydroxi-18,19-dinorpregn-4-en-20-in-3-one (norelgestromin) of Formula I with a relation of isomers E/Z of 1.6 and a purity of 99.8%