Process for manufacturing oxycodone

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C546S045000

Reexamination Certificate

active

06864370

ABSTRACT:
Oxycodone is manufactured in high yields and with a high purity using codeine or a salt of codeine as the starting material. The manufacturing process involves the following steps:(a) codeine or a codeine salt (e.g., codeine phosphate) is converted into the intermediate N-carboalkoxy- or N-carboaryloxynorcodeine,(b) the intermediate N-carboalkoxy- or N-carboaryloxynorcodeine resulting from step (a) is oxidized to yield the intermediate N-carboalkoxy- or N-carboaryloxynorcodeinone;(c) the intermediate N-carboalkoxy- or N-carboaryloxynorcodeinone resulting from step (b) is enolized with a base and the resultant enolate is thereafter methylated to yield the intermediate N-carboalkoxy- or N-carboaryloxynorthebaine;(d) the intermediate N-carboalkoxy- or N-carboaryloxynorthebaine resulting from step (c) is reduce to yield thebaine;(e) the thebaine resulting from step (d) is oxidized to yield the intermediate 14-hydroxycodeinone; and(f) the intermediate 14-hydroxycodeinone resulting from step (e) is hydrogenated to yield oxycodone.

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Journal of Medicinal Chemistry, vol. 17 (1974), 1117.

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