Pharmaceutical composition of 2-(4-isobutylphenyl) propionic acid

• US 6,727,286 B2
• Filed: 11/02/2001
• Issued: 04/27/2004
• Est. Priority Date: 11/02/2001
• Status: Expired due to Term

• Current Assignee: Cumberland Pharmaceuticals Inc.
• Original Assignee: Cumberland Pharmaceuticals Inc.
• Inventors: Pavliv, Leo
• Primary Examiner(s): Cook, Rebecca
• Application Number:
  US09/985,246
• Publication Number:
  US 20030100612A1
• Time in Patent Office: 907 Days
• Field of Search: 514/565, 514/568, 514/57
• US Class Current: 514/565
• CPC Class Codes: A61K 2300/00 Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
• CPC Class Codes: A61K 31/192 having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid cannabinoids A61K31/658
• CPC Class Codes: A61K 31/198 Alpha-amino acids, e.g. alanine or edetic acid [EDTA] betaine A61K31/205; proline A61K31/401; tryptophan A61K31/405; histidine A61K31/4172; peptides not degraded to individual amino acids A61K38/00
• CPC Class Codes: A61K 9/19 lyophilised , i.e. freeze-dried, solutions or dispersions lyophilised products with subsequent particle size reduction A61K9/14; granules or pellets made by lyphilisation A61K9/1682; solid oral dosage forms made by lyophilisation A61K9/2095; lyophilisation additives A61K47/00

Abstract

The present invention provides a pharmaceutical composition comprising an aqueous solution of arginine and ibuprofen, wherein the molar ratio of arginine to ibuprofen is less than 1:1, as well as a method of making the same. The present invention also provides a method of treating a condition chosen from pain, inflammation, fever, and/or other conditions alleviated by ibuprofen comprising administering a pharmaceutical composition comprising an aqueous solution of arginine and ibuprofen, wherein the molar ratio of arginine to ibuprofen is less than 1:1.

Claims

1. A pharmaceutical composition comprising an aqueous solution of arginine and ibuprofen, wherein the molar ratio of arginine to ibuprofen is less than or equal to 0.97:

1.

2. The pharmaceutical composition of claim 1, wherein the aqueous solution of arginine and ibuprofen has been terminally sterilized.

3. The pharmaceutical composition of claim 1, wherein the aqueous solution of arginine and ibuprofen has been lyophilized.

4. The pharmaceutical composition of claim 1, wherein the ibuprofen is (RS)-Ibuprofen.

5. The pharmaceutical composition of claim 1, wherein the ibuprofen is (S)-Ibuprofen.

6. The pharmaceutical composition of claim 1, wherein the arginine is L-arginine.

7. The pharmaceutical composition of claim 1, wherein the arginine is D-arginine.

8. The pharmaceutical composition of claim 1, wherein the molar ratio of arginine to ibuprofen is from about 0.10:

1 to about 0.97;

1.

9. The pharmaceutical composition of claim 8, wherein the molar ratio of arginine to ibuprofen is 0.92:

1.

10. The pharmaceutical composition of claim 8, wherein the molar ratio of arginine to ibuprofen is 0.60:

1.

11. The pharmaceutical composition of claim 8, wherein the molar ratio of arginine to ibuprofen is 0.97:

1.

39. The pharmaceutical composition of claim 1, the molar ratio of arginine to ibuprofen is from about 0.60:

1 to about 0.97;

1.

40. The pharmaceutical composition of claim 39, wherein said molar ratio is from about 0.92:

1 to about 0.97;

1.

12. A method of making a pharmaceutical composition comprising an aqueous solution of arginine and ibuprofen, the method comprising dissolving arginine in water to form an arginine solution and dissolving ibuprofen in the arginine solution to form the aqueous solution of arginine and ibuprofen, wherein the molar ratio of arginine to ibuprofen is less than or equal to 0.97:

1.

13. The method of claim 12, wherein the molar ratio of arginine to ibuprofen is from about 0.10:

1 to about 0.97;

1.

14. The method of claim 12, wherein the molar ratio of arginine to ibuprofen is 0.92:

1.

15. The method of claim 12, wherein the molar ratio of arginine to ibuprofen is 0.60:

1.

16. The method of claim 12, wherein the molar ratio of arginine to ibuprofen is 0.97:

1.

17. The method of claim 12, further comprising terminally sterilizing the aqueous solution of arginine and ibuprofen.

18. The method of claim 12, further comprising lyophilizing the aqueous solution of arginine and ibuprofen.

19. The method of claim 12, wherein the ibuprofen is (RS)-Ibuprofen.

20. The method of claim 12, wherein the ibuprofen is (S)-Ibuprofen.

21. The method of claim 12, wherein the arginine is L-arginine.

22. The method of claim 12, wherein the arginine is D-arginine.

37. A pharmaceutical composition comprising an aqueous solution of arginine and ibuprofen prepared according to the method of claim 12.

41. The method of claim 12, wherein the molar ratio of arginine to ibuprofen is from about 0.60:

1 to about 0.97;

1.

42. The method of claim 41, wherein the molar ratio of arginine to ibuprofen is from about 0.92:

1 to about 0.97;

1.

23. A method of treating one or more conditions chosen from pain, inflammation, fevers, and, patent ductus arteriosis comprising administering to a patient in need thereof an effective amount of an aqueous solution of arginine and ibuprofen, wherein the molar ratio of arginine to ibuprofen is less than or equal to 0.97:

1.

24. The method of claim 23, wherein the molar ratio of arginine to ibuprofen is from about 0.10:

1 to about 0.97;

1.

25. The method of claim 23, wherein the molar ratio of arginine to ibuprofen is 0.92:

1.

26. The method of claim 23, wherein the molar ratio of arginine to ibuprofen is 0.60:

1.

27. The method of claim 23, wherein the molar ratio of arginine to ibuprofen is 0.97:

1.

28. The method of claim 23, wherein the administration occurs via intravenous injection.

29. The method of claim 23, wherein the administration occurs via intramuscular injection.

30. The method of claim 23, wherein the administration occurs orally.

31. The method of claim 23, wherein the effective amount is from about 100 mg to about 800 mg of ibuprofen.

32. The method of claim 31, wherein the effective amount is about 400 mg of ibuprofen.

33. The method of claim 23, wherein the effective amount is about 7.5 mg/kg of ibuprofen.

34. The method of claim 23, wherein the condition is pain.

35. The method of claim 23, wherein the condition is inflammation.

36. The method of claim 23, wherein the condition is fever.

38. The method of claim 23, wherein the condition is patent ductus arteriosis.

43. The method of claim 23, wherein the molar ratio of arginine to ibuprofen is from about 0.60:

1 to about 0.97;

1.

44. The method of claim 43, wherein the molar ratio of arginine to ibuprofen is from about 0.92:

1 to about 0.97;

1.