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US 7,674,800 B2Granted
Oxycodone hydrochloride having less than 25 PPM 14-hydroxycodeinone
AssigneePurdue Pharma L.P.
InventorsRobert Chapman, Lonn S. Rider, Qi Hong, Donald Kyle, Robert Kupper
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Abstract
In certain embodiments the invention is directed to a process for preparing an oxycodone hydrochloride composition having less than 25 ppm of 14-hydroxycodeinone.
Claims81
A process for preparing an oxycodone salt substantially free of 14-hydroxycodeinone, which process comprises steps of:
- (a) preparing a mixture of oxycodone free base, solvent and an acid, the oxycodone free base having an 8α,14-dihydroxy-7,8-dihydrocodeinone component;
- (b) incubating the mixture under conditions suitable to convert the oxycodone free base to an oxycodone salt, wherein said conditions promote an acid catalyzed dehydration consisting of conversion of the 8α,14-dihydroxy-7,8-dihydrocodeinone component to 14-hydroxycodeinone;
- and
- (c) preferentially removing the 14-hydroxycodeinone from the oxycodone salt.
1 more element
An oxycodone hydrochloride composition having less than 25 ppm 14-hydroxycodeinone, the composition prepared by a process comprising:
- preparing a mixture of oxycodone free base, solvent and hydrochloric acid, the oxycodone free base having an 8α,14-dihydroxy-7,8-dihydrocodeinone component,
- incubating the mixture under conditions suitable to convert the oxycodone free base to an oxycodone hydrochloride having more than 100 ppm 14-hydroxycodeinone, wherein said conditions promote an acid catalyzed dehydration of the 8α,14-dihydroxy-7,8-dihydrocodeinone component to 14-hydroxycodeinone, and
- hydrogenating the oxycodone hydrochloride composition having more than 100 ppm 14-hydroxycodeinone until the oxycodone hydrochloride composition contains less than 25 ppm 14-hydroxycodeinone,
- wherein at least a portion of the 14-hydroxycodeinone in the composition having more than 100 ppm 14-hydroxycodeinone was derived from the 8α,14-dihydroxy-7,8-dihydrocodeinone component during the conversion of the oxycodone free base to the oxycodone salt.
1 more element
A process for preparing an oxycodone salt substantially free of 14-hydroxycodeinone, which process comprises steps of:
- (a) preparing a mixture of oxycodone free base, solvent and an acid, the oxycodone free base having an 8α,14-dihydroxy-7,8-dihydrocodeinone component;
- (b) incubating the mixture under conditions suitable to convert the oxycodone free base to an oxycodone salt, wherein said conditions promote an acid catalyzed dehydration whereby the 8α,14-dihydroxy-7,8-dihydrocodeinone component is converted to 14-hydroxycodeinone;
- and
- (c) reducing an amount of 14-hydroxycodeinone in the oxycodone salt formed in step (b) to produce an oxycodone salt composition having less than 25 ppm 14-hydroxycodeinone.
1 more element
Dependencies are inferred from the claim text.