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Details for Patent: 9,314,461

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Details for Patent: 9,314,461

Title:Oral formulations and lipophilic salts of methylnaltrexone
Abstract: The present invention provides compositions comprising methylnaltrexone or a salt thereof, and compositions and formulations thereof, for oral administration.
Inventor(s): Shah; Syed M. (Delray Beach, FL), Diorio; Christopher Richard (Campbell Hall, NY), Ehrnsperger; Eric C. (New City, NY), Meng; Xu (San Diego, CA), Al Shareffi; Kadum A. (Greensboro, NC), Cohen; Jonathan Marc (N/A)
Assignee: Wyeth, LLC (Madison, NJ)
Filing Date:Jul 31, 2013
Application Number:13/956,050
Claims:1. A pharmaceutical composition for oral administration comprising a solid dosage of (i) methylnaltrexone, or a pharmaceutically acceptable salt thereof, and (ii) and an amphiphilic pharmaceutically acceptable excipient comprising a saturated or unsaturated, branched or unbranched, cyclic or acyclic C.sub.4-30 aliphatic group that is optionally substituted, wherein when the methylnaltrexone, or the pharmaceutically acceptable salt thereof, and the amphiphilic pharmaceutically acceptable excipient are in solution, the apparent octanol/water partition coefficient for methylnaltrexone is at least 0.25 at a pH between 1 and 4.

2. The pharmaceutical composition according to claim 1, wherein the amphiphilic pharmaceutically acceptable excipient has a pK.sub.a of 3 or less.

3. The pharmaceutical composition according to claim 1, wherein the amphiphilic pharmaceutically acceptable excipient comprises a sulfate (-OSO.sub.3.sup.-) group.

4. The pharmaceutical composition according to claim 1, wherein the amphiphilic pharmaceutically acceptable excipient comprises an acyclic C.sub.4-30 aliphatic group that is optionally substituted.

5. The pharmaceutical composition according to claim 1, wherein the amphiphilic pharmaceutically acceptable excipient comprises a saturated, unbranched, acyclic, unsubstituted C.sub.4-30 alkyl group.

6. The pharmaceutical composition according to claim 1, wherein the amphiphilic pharmaceutically acceptable excipient comprises a saturated, unbranched, acyclic, unsubstituted C.sub.7-15 alkyl group.

7. The pharmaceutical composition according to claim 1, wherein the amphiphilic pharmaceutically acceptable excipient comprises a C.sub.12 n-alkyl group.

8. The pharmaceutical composition according to claim 1, wherein the amphiphilic pharmaceutically acceptable excipient is sodium dodecyl sulfate (SDS).

9. The pharmaceutical composition of claim 1, further comprising a disintegrant.

10. The pharmaceutical composition of claim 9, wherein at least 50% of the composition dissolves in a dissolution apparatus with paddles at 100 rpm in 900 mL of 0.1 N HCl at 37.degree. C. within about 15 minutes.

11. The composition of claim 10, wherein at least 75% of the composition dissolves in a dissolution apparatus with paddles at 100 rpm in 900 mL of 0.1 N HCl at 37.degree. C. within about 15 minutes.

12. The composition according to claim 1, wherein the apparent octanol/water partition coefficient is at least 1.

13. The composition according to claim 12, wherein the apparent octanol/water partition coefficient is at least 10.

14. The composition according to claim 13, wherein the apparent octanol/water partition coefficient is at least 20.

15. The composition according to claim 1, wherein the amphiphilic pharmaceutically acceptable excipient is an anionic surfactant.

16. The composition according to claim 9, wherein the disintegrant is an effervescent disintegrant.

17. The composition according to claim 16, wherein the disintegrant is a bicarbonate.

18. The composition according to claim 1, wherein the composition is a tablet.

19. The composition according to claim 1, wherein the composition is a tablet comprising at least one or more of a binder, a chelating agent, a wetting agent, a lubricant, a non-functional coating, or an antioxidant, and combinations thereof.

20. The composition according to claim 19, wherein the composition comprises a chelating agent.

21. The composition according to claim 20, wherein the chelating agent is a salt of EDTA.

22. The composition according to claim 21, wherein the chelating agent is calcium EDTA disodium.

23. The composition according to claim 19, wherein the composition comprises a lubricant.

24. The composition according to claim 23, wherein the lubricant is magnesium stearate.

25. The composition according to claim 24, wherein the composition comprises an antioxidant.

26. The composition according to claim 25, wherein the antioxidant is ascorbic acid.

27. The composition according to claim 19, wherein the antioxidant is ascorbic acid.

28. A pharmaceutical composition for oral administration comprising a solid dosage of a compound of formula (I): ##STR00006## wherein A.sup.- is an anion of the amphiphilic pharmaceutically acceptable excipient comprising a saturated or unsaturated, branched or unbranched, cyclic or acyclic C.sub.4-30 aliphatic group that is optionally substituted, wherein when the compound of formula I is in solution, the apparent octanol/water partition coefficient is at least 0.25 at a pH between 1 and 4.

29. The pharmaceutical composition of claim 1, wherein the methylnaltrexone, or a pharmaceutically acceptable salt thereof, and the amphiphilic pharmaceutically acceptable excipient form an ion pair when dissolved in solution.

30. The pharmaceutical composition of claim 1, wherein the composition comprises from about 5% to about 80% amphiphilic pharmaceutically acceptable excipient, based upon the total weight of the composition.

31. The pharmaceutical composition of claim 1, wherein the composition comprises about 7% to about 75% methylnaltrexone, based upon total weight of the composition.

32. The composition according to claim 1, wherein the apparent octanol/water partition coefficient is at least 30.

33. The composition according to claim 16, wherein the disintegrant is sodium bicarbonate.

34. The composition according to claim 19, wherein the composition comprises: (a) about 7% to about 75% of methylnaltrexone bromide, based upon total weight of the composition; (b) about 5% to about 80% of the amphiphilic pharmaceutically acceptable excipient, based upon total weight of the composition; (c) about 0.01% to about 5% of a chelating agent, based upon total weight of the composition; (d) about 1% to about 25% of a wetting agent, based upon total weight of the composition; (e) about 5% to about 90% of a binder, based upon total weight of the composition; (f) about 1% to about 25% of a disintegrant, based upon total weight of the composition; (g) about 0.1% to about 7% of a lubricant, based upon total weight of the composition; and optionally (h) about 0.01% to about 5% of an antioxidant, based upon the total weight of the composition.

35. The composition according to claim 34, wherein the binder comprises microcrystalline cellulose and silicified microcrystalline cellulose.

36. The composition according to claim 34, wherein the disintegrant is crospovidone.

37. The composition according to claim 34, wherein the chelating agent is calcium EDTA.

38. The composition according to claim 34, wherein the wetting agent is polysorbate 80.

39. The composition according to claim 34, wherein the lubricant is magnesium stearate.

40. The composition according to claim 34, wherein the antioxidant is ascorbic acid.
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