Low abuk oxycodone, its salts and methods of making same

Abstract

A method of preparing oxycodone includes forming 14-hydroxycodeine by reduction of 14-hydroxycodeinone and rearrangement of the 14-hydroxycodeine to form the oxycodone. During the reduction step, the ketone group of an undesirable contaminant precursor, 8,14-dihydroxy-7,8-dihydrocodeinone, is reduced to a hydroxyl group thus forming a triol. This triol is substantially inert with respect to reforming 14-hydroxycodeinone and can be readily separated from oxycodone.

What is claimed: 
     
         1 . An oxycodone free base composition having less than 25 ppm 14-hydroxycodeinone and less than 2 ppm of 8α,14-dihydroxy-7,8-dihydrocodeinone. 
     
     
         2 . The oxycodone free base composition of  claim 1 , further comprising less than about 1 area percent 6-oxycodol by HPLC. 
     
     
         3 . The oxycodone free base composition of  claim 1 , having less than 10 ppm of 14-hydroxycodeinone. 
     
     
         4 . The oxycodone free base composition of  claim 1 , having less than 5 ppm of 14-hydroxycodeinone. 
     
     
         5 . An oxycodone hydrochloride composition having less than 25 ppm 14-hydroxycodeinone and less than 2 ppm of 8α,14-dihydroxy-7,8-dihydrocodeinone. 
     
     
         6 . The oxycodone hydrochloride composition of  claim 5 , having less than 10 ppm 14-hydroxycodeinone. 
     
     
         7 . The oxycodone hydrochloride composition of  claim 5 , having less than 5 ppm 14-hydroxycodeinone. 
     
     
         8 . The oxycodone hydrochloride composition of  claim 5 , having less than 2 ppm of 14-hydroxycodeinone. 
     
     
         9 . An oxycodone free base composition produced by rearrangement of 14-hydroxycodeine and having less than 25 ppm 14-hydroxycodeinone. 
     
     
         10 . The oxycodone free base composition of  claim 9 , having less than 2 ppm of 8α,14-dihydroxy-7,8-dihydrocodeinone. 
     
     
         11 . The oxycodone free base composition of  claim 10 , having less than 10 ppm of 14-hydroxycodeinone. 
     
     
         12 . The oxycodone free base composition of  claim 10 , having less than 5 ppm of 14-hydroxycodeinone. 
     
     
         13 . An oxycodone free base composition having less than 25 ppm 14-hydroxycodeinone, wherein at least a portion of the composition is derived from a rearrangement of 14-hydroxycodeine. 
     
     
         14 . The composition of  claim 13 , wherein the rearrangement results from contacting 14-hydroxycodeine with a catalyst. 
     
     
         15 . The composition of  claim 14 , wherein the catalyst is a ligand-complexed metal catalyst. 
     
     
         16 . The composition of  claim 15 , wherein the catalyst is Wilkinson's catalyst. 
     
     
         17 . The composition of  claim 15 , wherein the metal is rhodium or ruthenium. 
     
     
         18 . An oxycodone hydrochloride composition having less than 25 ppm 14-hydroxycodeinone and less than 2 ppm of 8α,14-dihydroxy-7,8-dihydrocodeinone, wherein the composition is derived from the oxycodone free base composition of  claim 13 .