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Generated: August 17, 2017

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Title: Drug-resin complexes stabilized by chelating agents
Abstract:The invention provides a pharmaceutical composition comprising a drug-resin complex and a chelating agent in which the composition is in the form of a solid or a gel. The invention also provides a method of making such a composition and a method for improving the stability of a pharmaceutical composition.
Inventor(s): Eichman; Martin L. (Fairport, NY)
Assignee: Medeva Pharmaceuticals Manufacturing (Rochester, NY)
Application Number:08/834,359
Patent Claims: 1. A pharmaceutical composition comprising a drug-resin complex and a chelating agent,

wherein the composition is in the form of a solid or a gel,

wherein the chelating agent is present in an amount effective to reduce the amount of degradation of the drug in the drug resin complex by more than 20 percent over twelve months of storage at room temperature relative to an otherwise identical pharmaceutical composition without the chelating agent;

wherein the changing agent is selected from EDTA or a salt of EDTA; and

wherein the drug in the drug-resin complex is selected from dextromethorphan, codeine, morphine, hydrcodone, pseudoephedrine, or phenylpropanolamine.

2. A pharmaceutical composition according to claim 1, wherein the composition is in the form of a solid.

3. A pharmaceutical composition according to claim 1, wherein the resin in the drug-resin complex is a cationic exchange resin.

4. A pharmaceutical composition according to claim 3, wherein the resin is a divinylbenzene sulfonic acid cationic exchange resin.

5. A pharmaceutical composition according to claim 1, wherein the chelating agent is not covalently bound to the drug resin complex.

6. A pharmaceutical composition according to claim 1, wherein the chelating agent is covalently bound to the drug resin complex.

7. A pharmaceutical composition according to claim 1, wherein the chelating agent is present in a concentration of from 0.001 to 10 percent by weight.

8. A pharmaceutical composition according to claim 1, wherein the chelating agent is present in a concentration of from 0.1 to 5 percent by weight.

9. A pharmaceutical composition according to claim 1, wherein the drug-resin complex comprises a diffusion barrier coating.

10. A pharmaceutical composition according to claim 9, wherein the diffusion barrier coating is an enteric coating.

11. A pharmaceutical composition according to claim 1, wherein the drug-resin complex comprises a solvating agent.

12. A pharmaceutical composition according to claim 11, wherein the solvating agent is polyethylene glycol.

13. A pharmaceutical composition according to claim 1, wherein the drug-resin complex comprises a solvating agent and a diffusion barrier coating.

14. A pharmaceutical composition according to claim 1, wherein the pharmaceutical composition is suitable for oral, topical, rectal, vaginal, nasal, or ophthalmic administration.

15. A pharmaceutical composition according to claim 1, wherein the pharmaceutical composition is in the form of a tablet, a capsule, a powder, a lotion, a cream, or a suppository.

16. A pharmaceutical composition according to claim 14, wherein the pharmaceutical composition is suitable for oral administration.

17. A method of making a pharmaceutical composition comprising:

(a) combining a drug and an ion exchange resin in a liquid to form a drug-resin complex;

(b) adding a chelating agent; and

(c) drying the result of step (b) to form a solid or gel pharmaceutical composition,

wherein the chelating agent is present in an amount effective to reduce the amount of degradation of the drug in the drug resin complex by more than 20 percent over twelve months of storage at room temperature relative to an otherwise identical pharmaceutical composition without the chelating agent;

wherein the chelating agent is selected from EDTA or a salt of EDTA; and

wherein the drug in the drug-resin complex is selected from dextromethorphan, codeine, morphine, hydrcodone, pseudoephedrine, or phenylpropanolamine.

18. A method of making a pharmaceutical composition comprising:

(a) combining a drug and an ion exchange resin in a liquid to form a drug-resin complex;

(b) adding a chelating agent;

(c) drying the result of step (b) to form a solid; and

(d) suspending the result of step (c) in an appropriate liquid to form a liquid pharmaceutical composition,

wherein the chelating agent is present in an amount effective to reduce the amount of degradation of the drug in the drug resin complex by more than 20 percent over twelve months of storage at room temperature relative to an otherwise identical pharmaceutical composition without the chelating agents;

wherein the chelation agent is selected from EDTA or a salt of EDTA; and wherein the drug in the drug-resin complex is selected from dextromethorphan, codeine, morphine, hydrcodone, pseudoephedrine, or phenylpropanolamine.

19. A method of making a pharmaceutical composition comprising:

(a) combining a drug and an ion exchange resin in a first liquid to form a drug-resin complex;

(b) drying the result of step (a) to form a solid;

(c) suspending the result of step (b) in an appropriate second liquid, which may be the same or different than the first liquid; and

(d) adding a chelating agent, to form a liquid pharmaceutical composition,

wherein the chelating agent is present in an amount effective to reduce the amount of degradation of the drug in the drug resin complex by more than 20 percent over twelve months of storage at room temperature relative to an otherwise identical pharmaceutical composition without the chelating agent,

wherein the chelating agent is selected from EDTA or a salt of EDTA; and

wherein the drug in the drug-resin complex is selected from dextromethorphan, codeine, morphine, hydrcodone, pseudoephedrine or phenylpropanolamine.

20. A pharmaceutical composition prepared by the process of:

(a) combining a drug and an ion exchange resin in a liquid to form a drug-resin complex;

(b) adding a chelating agent; and

(c) drying the result of step (b) to form a solid or gel pharmaceutical composition,

wherein the chelating agent is present in an amount effective to reduce the amount of degradation of the drug in the drug resin complex by more than 20 percent over twelve months of storage at room temperature relative to an otherwise identical pharmaceutical composition without the chelating agent;

wherein the chelating agent is selected from EDTA or a salt of EDTA; and

wherein the drug in the drug-resin complex is selected from dextromethorphan, codeine, morphine, hydrcodone, pseudephedrine, or phenylpropanolamine.

21. A pharmaceutical composition prepared by the process of:

(a) combining a drug and an ion exchange resin in a liquid to form a drug-resin complex;

(b) adding a chelating agent;

(c) drying the result of step (b) to form a solid; and

(d) suspending the result of step (c) in an appropriate liquid to form a liquid pharmaceutical composition,

wherein the chelating agent is present in an amount effective to reduce the amount of degradation of the drug in the drug resin complex by more than 20 percent over twelve months of storage at room temperature relative to an otherwise identical pharmaceutical composition without the chelating agent;

wherein the chelating element is selected from EDTA or a salt of EDTA; and

wherein the drug in the drug-resin complex is selected from dextromethorphan, codeine, morphine, hydrcodone, pseudoephedrine, or phenylpropanolamine.

22. A pharmaceutical composition prepared by the process of:

(a) combining a drug and an ion exchange resin in a first liquid to form a drug-resin complex;

(b) drying the result of step (a) to form a solid;

(c) suspending the result of step (b) in an appropriate second liquid, which may be the same or different than the first liquid; and

(d) adding a chelating agent, to form a liquid pharmaceutical composition,

wherein the chelating agent is present in an amount effective to reduce the amount of degradation of the drug in the drug resin complex by more than 20 percent over twelve months of storage at room temperature relative to an otherwise identical pharmaceutical composition without the chelating agent;

wherein the chelating agent is selected from EDTA or a salt of EDTA; and

wherein the drug in the drug-resin complex is selected from dextromethorphan, codeine, morphine, hydrcodone, pseudoephedrine, or phenylpropanolamine.

23. A method for improving the stability of a pharmaceutical composition that contains a drug-resin complex comprising adding a chelating agent in an amount effective to reduce the rate of degradation of the drug in the drug-resin complex by more than 20 percent over twelve months of storage at room temperature relative to an otherwise identical pharmaceutical composition without the chelating agent;

wherein the chelating agent is selected from EDTA or a salt of EDTA; and

wherein the drug in the drug-resin complex is selected from dextromethorphan, codeine, morphine, hydrocodone, pseudoephedrine, or phenylpropanolamine.

24. A method according to claim 23, wherein the composition is a solid.

25. A method according to claim 23, wherein the composition is a gel.

26. A method according to claim 23, wherein the composition is a suspension.

27. A method for administering a drug to a patient in need thereof, comprising:

(a) providing a pharmaceutical composition that contains a drug-resin complex that contains the drug;

(b) adding a chelating agent;

(c) storing the combination of step (b); and

(d) subsequently administering the combination of step (b) to the patient,

wherein the chelating agent is present in an amount effective to reduce the amount of degradation of the drug in the drug resin complex by more than 20 percent over twelve months of storage at room temperature relative to an otherwise identical pharmaceutical composition without the chelating agent;

wherein the chelating agent is selected from EDTA or a salt of EDTA; and

wherein the drug in the drug-resin complex is selected from dextromethorphan, codeine, morphine, hydrocodone, pseudoephedrine, or phenylpropanolamine.

28. A pharmaceutical composition according to claim 1, wherein the drug in the drug-resin complex is dextromethorphan.

29. A pharmaceutical composition according to claim 1, wherein the drug in the drug-resin complex is codeine.

30. A method according to claim 17, wherein the drug in the drug-resin complex is dextromethorphan.

31. A method according to claim 17, wherein the drug in the drug-resin complex is codeine.

32. A method according to claim 17, wherein the drug in the drug-resin complex is dextromethorphan.

33. A method according to claim 18, wherein the drug in the drug-resin complex is codeine.

34. A method according to claim 19, wherein the drug in the drug-resin complex is dextromethorphan.

35. A method according to claim 19, wherein the drug in the drug-resin complex is codeine.

36. A method according to claim 23, wherein the drug in the drug-resin complex is dextromethorphan.

37. A method according to claim 23, wherein the drug in the drug-resin complex is codeine.
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