IP Library Granted Patent US 8,563,571
Granted Patent B2
US 8,563,571 · App. 13/187,854 · Granted Oct 22, 2013

Crystalline forms of oxymorphone hydrochloride

Inventors: Karen S. Gushurst (West Lafayette, IN); Leonard J. Chyall (Lafayette, IN); Lien H. Koztecki (Indianapolis, IN); Brenton Skylar Wolfe (West Lafayette, IN)
Assignee: Noramco, Inc.
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Quick Facts
Patent No.
US 8,563,571
App. No.
13/187,854
Granted
Oct 22, 2013
Kind
B2
Abstract

The present invention is directed to crystalline forms of oxymorphone hydrochloride.

Claims (56)

1. A form of oxymorphone HCl selected from the group consisting of Form B, Form C, Form D, Form F, Form G, Form H, Form J, Form K, Form L and Form M; wherein:

Form B has pXRD °2θ peaks at about 7.98, about 9.85, about 10.68, about 11.55 and about 14.70;

Form C has pXRD °2θ peaks at about 7.83 and about 12.31;

Form D has pXRD °2θ peaks at about 6.96, about 10.55, about 12.34 and about 15.03;

Form F has pXRD °2θ peaks at about 9.78, about 10.71, about 11.06 and about 12.03;

Form G has pXRD °2θ peaks at about 8.12, about 9.88, about 13.27 and about 13.79;

Form H has pXRD °2θ peaks at about 6.60, about 7.91 and about 11.30;

Form J has pXRD °2θ peaks at about 5.19, about 5.50, about 6.02 and about 11.07;

Form K has pXRD °2θ peaks at about 8.08, about 12.48 and about 12.89;

Form L has pXRD °2θ peaks at about 9.58, about 10.20 and about 12.56; and

Form M has pXRD °2θ peaks at about 5.70, about 11.44 and about 13.47.

2. A form of oxymorphone HCl selected from the group consisting of Form B, Form C, Form D, Form F, Form G, Form H, Form J, Form K, Form L and Form M; wherein:

Form B has pXRD °2θ peaks at 7.98, 9.85, 10.68, 11.55, 14.04 and 14.70;

Form C has pXRD °2θ peaks at 7.83, 10.74, 11.64, 12.31, 14.23 and 15.44;

Form D has pXRD °2θ peaks at 6.96, 10.55, 11.74, 12.3415.03 and 1538;

Form F has pXRD °2θ peaks at 9.78, 10.71, 12.03, 12.86, 13.58 and 16.49;

Form G has pXRD °2θ peaks at 8.12, 9.88, 11.82, 12.34, 13.27 and 13.79;

Form H has pXRD °2θ peaks at 6.60, 7.91, 8.36, 10.40, 11.30 and 11.96;

Form J has pXRD °2θ peaks at 5.19, 5.50, 6.02, 7.78, 8.37, 10.38, 11.07, 11.90, 12.07 and 12.76;

Form K has pXRD °2θ peaks at 8.08, 12.48, 12.89, 15.73, 16.22 and 18.12;

Form L has pXRD °2θ peaks at 9.58, 9.89, 10.20, 11.24, 12.56 and 15.22; and

Form M has pXRD °2θ peaks at 5.70, 11.44, 2.92, 13.06, 13.47 and 14.14.

3. A form of oxymorphone HCl selected from the group consisting of Form B, Form C, Form D, Form F, Form G, Form H, Form J, Form K, Form L and Form M; wherein:

Form B has pXRD °28 peaks at 7.98, 10.68, 11.55, 14.70, 16.18, 17.19 and 19.12;

Form C has pXRD °2θ peaks at 7.83, 10.74, 11.64, 12.31, 14.23, 15.44, 16.20, 17.62 and 17.97;

Form D has pXRD °2θ peaks at 6.96, 10.55, 11.74, 12.34, 15.03, 15.86, 16.07, 17.35, 17.59 and 19.76;

Form F has pXRD °2θ peaks at 9.78, 10.71, 11.06, 12.03, 16.73 and 19.75;

Form G has pXRD °2θ peaks at 8.12, 13.27, 13.79, 15.80 and 16.18;

Form H has pXRD °2θ peaks at 8.36, 11.30, 11.96, 13.20, 15.9, 18.02 and 19.99;

Form J has pXRD °2θ peaks at 5.19, 5.50, 6.02, 7.78, 8.37, 10.38, 11.07, 11.90, 12.07, 12.76, 15.50 and 16.57;

Form K has pXRD °2θ peaks at 8.08, 12.48, 12.89, 15.73, 16.22, 18.12, 19.05 and 20.51;

Form L has pXRD °2θ peaks at 9.58, 9.89, 10.20, 11.24, 16.33, 19.10 and 19.23; and

Form M has pXRD °2θ peaks at 12.92, 13.06, 13.47, 14.14 and 17.30.

4. A form of oxymorphone HCl as in claim 1 , wherein, as measured by Differential Scanning calorimetry (DSC):

Form B is characterized by an endotherm at about 126° C.;

Form D is characterized by an endotherm at about 163° C.;

Form J is characterized by a first endotherm at about 154° C. and a second endotherm at about 164° C.; and

Form M is characterized by an endotherm at about 183° C.

5. A form of oxymorphone HCl as in claim 1 , which is about 90% to about 100% pure.

6. A form of oxymorphone HCl as in claim 1 , which is about 98% to about 100% pure.

7. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a form of oxymorphone HCl as in claim 1 .

8. A pharmaceutical composition made by mixing a form of oxymorphone HCl as in claim 1 and a pharmaceutically acceptable carrier.

9. A process for making a pharmaceutical composition comprising mixing a form of oxymorphone HCl as in claim 1 and a pharmaceutically acceptable carrier.

10. A method of providing an analgesic effect, comprising administering to a subject in need thereof, a therapeutically effective amount of a form of oxymorphone HCl as in claim 1 .

11. A form of oxymorphone HCl as in claim 2 , which is about 90% to about 100% pure.

12. A form of oxymorphone HCl as in claim 2 , which is about 98% to about 100% pure.

13. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a form of oxymorphone HCl as in claim 2 .

14. A pharmaceutical composition made by mixing a form of oxymorphone HCl as in claim 2 and a pharmaceutically acceptable carrier.

15. A process for making a pharmaceutical composition comprising mixing a form of oxymorphone HCl as in claim 2 and a pharmaceutically acceptable carrier.

16. A method of providing an analgesic effect, comprising administering to a subject in need thereof, a therapeutically effective amount of a form of oxymorphone HCl as in claim 2 .

17. A form of oxymorphone HCl as in claim 4 , which is about 90% to about 100% pure.

18. A form of oxymorphone HCl as in claim 4 , which is about 98% to about 100% pure.

19. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a form of oxymorphone HCl as in claim 4 .

20. A pharmaceutical composition made by mixing a form of oxymorphone HCl as in claim 4 and a pharmaceutically acceptable carrier.

21. A process for making a pharmaceutical composition comprising mixing a form of oxymorphone HCl as in claim 4 and a pharmaceutically acceptable carrier.

22. A method of providing an analgesic effect, comprising administering to a subject in need thereof, a therapeutically effective amount of a form of oxymorphone HCl as in claim 4 .

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded May 1, 2026
From: CERBERUS BUSINESS FINANCE, LLC
To: NORAMCO, LLC (FORMERLY KNOWN AS NORAMCO, INC.)
Reel/Frame 074545/0583 →
ENTITY CONVERSION Recorded Feb 6, 2020
From: NORAMCO, INC.
To: NORAMCO, LLC
Reel/Frame 051839/0179 →
ASSIGNMENT FOR SECURITY - - PATENTS Recorded Jul 1, 2016
From: NORAMCO, INC.
To: CERBERUS BUSINESS FINANCE, LLC, AS COLLATERAL AGENT
Reel/Frame 039231/0090 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 3, 2012
From: GUSHURST, KAREN S.; CHYALL, LEONARD J; KOZTECKI, LIEN H.; WOLFE, BRENTON SKYLAR
To: NORAMCO, INC.
Reel/Frame 028066/0575 →
Continuity (2)
Provisional Application 61366690 · Jul 22, 2010
Related Publication 20120022093A1 · Jan 26, 2012