Process for preparing morphinan-6-one products with low levels of α,β-unsaturated ketone compounds

• US 8,871,779 B2
• Filed: 03/02/2007
• Issued: 10/28/2014
• Est. Priority Date: 03/02/2006
• Status: Active Grant

• Current Assignee: SpecGx LLC (Mallinckrodt plc)
• Original Assignee: Mallinckrodt LLC (Mallinckrodt plc)
• Inventors: Buehler, Henry J., Dummitt, William E., Mannino, Anthony, Aubuchon, Dennis C., Gu, Hong
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US11/915,606
• Publication Number:
  US 20080312442A1
• Time in Patent Office: 2,797 Days
• Field of Search: 546/45, 546/44, 514/282
• US Class Current: 514/282
• CPC Class Codes: A61K 31/485 Morphinan derivatives, e.g. morphine, codeine
• CPC Class Codes: C07D 489/08 Oxygen atom

Abstract

The present invention generally relates to processes for preparing highly pure morphinan-6-one products. The processes involve reducing the concentration of α,β-unsaturated ketone compounds present as impurities in morphinan 6 one products or reaction mixtures including morphinan 6 one compounds by treatment with a sulfur-containing compound. (A)

Claims

1. A hydrochloride salt of oxymorphone comprising less than 0.001% of 14-hydroxymorphinone.

2. The hydrochloride salt of claim 1 comprising less than 0.0005% of 14-hydroxymorphinone.

3. A pharmaceutical acceptable form comprising the oxymorphone hydrochloride according to claim 1.

4. A hydrochloride salt of a morphinan-6-one compound corresponding to Formula (2):

5. The hydrochloride salt of claim 4 comprising less than 0.0005% of 14-hydroxymorphinone.

6. A pharmaceutical formulation comprising the oxymorphone hydrochloride according to claim 4.