IP Library › Granted Patent US 9,662,300
Granted Patent B2
US 9,662,300 · App. 14/095,593 · Granted May 30, 2017

Solid naproxen concentrates and related dosage forms

Inventors: EmadEldin M. Hassan (Parkton, MD); Sridhar Gumudavelli (Cockeysville, MD)
Assignee: Pharmaceutics International, Inc.
A61K9/4833A61K9/1617A61K9/1688A61K9/4866A61K31/192
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Quick Facts
Patent No.
US 9,662,300
App. No.
14/095,593
Granted
May 30, 2017
Kind
B2
Abstract

The invention provides a composition consisting essentially of a solid naproxen concentrate, wherein the solid naproxen concentrate comprises (a) a solid naproxen free acid and (b) a solid naproxen alkali salt, and wherein at least 90% of the weight of the solid naproxen concentrate is naproxen free acid and naproxen alkali salt, as well methods of producing such a solid naproxen concentrate.

Claims (26)

1. A pharmaceutical composition consisting essentially of a solid naproxen concentrate, wherein the solid naproxen concentrate consists of (a) a solid naproxen free acid, (b) a solid naproxen alkali salt, and (c) at least one acidic substance selected from the group consisting of lactic acid, gluconic acid, citric acid, tartaric acid, hydrochloric acid, phosphoric acid, nitric acid, sulfuric acid, maleic acid, monosodium citrate, disodium citrate, potassium citrate, monosodium tartrate, disodium tartrate, potassium tartrate, aspartic acid, carboxy-methylcellulose, acrylic polymers, methacrylic polymers, and mixtures thereof, wherein at least 90% of the weight of the solid naproxen concentrate is naproxen free acid and naproxen alkali salt, and wherein the solid naproxen concentrate does not comprise one or more binders.

2. The composition of claim 1 , wherein at least 92% of the weight of the solid naproxen concentrate is naproxen free acid and naproxen alkali salt.

3. The composition of claim 1 , wherein at least 95% of the weight of the solid naproxen concentrate is naproxen free acid and naproxen alkali salt.

4. The composition of claim 1 , wherein at least 97% of the weight of the solid naproxen concentrate is naproxen free acid and naproxen alkali salt.

5. The composition of claim 1 , wherein the composition is a hard shell capsule, soft gelatin capsule, liquid suspension, liquid solution, or tablet.

6. The composition of claim 5 , wherein the composition is a tablet.

7. The composition of claim 6 , equivalent to about 200 to about 1000 mg naproxen per tablet.

8. The composition of claim 1 , wherein the solid naproxen alkali salt is selected from the group consisting of naproxen sodium salt, naproxen potassium salt, naproxen ammonium salt, and mixtures thereof.

9. A pharmaceutical formulation comprising (a) a solid naproxen concentrate, wherein the solid naproxen concentrate consists of a solid naproxen free acid, a solid naproxen alkali salt, and at least one acidic substance selected from the group consisting of lactic acid, gluconic acid, citric acid, tartaric acid, hydrochloric acid, phosphoric acid, nitric acid, sulfuric acid, maleic acid, monosodium citrate, disodium citrate, potassium citrate, monosodium tartrate, disodium tartrate, potassium tartrate, aspartic acid, carboxy-methylcellulose, acrylic polymers, methacrylic polymers, and mixtures thereof, wherein at least 90% of the weight of the solid naproxen concentrate is naproxen free acid and naproxen alkali salt, and wherein the solid naproxen concentrate does not comprise one or more binders; and (b) a pharmaceutically acceptable carrier.

10. The composition of claim 9 , wherein at least 92% of the weight of the solid naproxen concentrate is naproxen free acid and naproxen alkali salt.

11. The composition of claim 9 , wherein at least 95% of the weight of the solid naproxen concentrate is naproxen free acid and naproxen alkali salt.

12. The composition of claim 9 , wherein at least 97% of the weight of the solid naproxen concentrate is naproxen free acid and naproxen alkali salt.

13. The composition of claim 9 , wherein the composition is a hard shell capsule, soft gelatin capsule, liquid suspension, liquid solution, or tablet.

14. The composition of claim 13 , wherein the composition is a tablet.

15. The composition of claim 14 , equivalent to about 200 to about 1000 mg naproxen per tablet.

16. The composition of claim 9 , wherein the solid naproxen alkali salt is selected from the group consisting of naproxen sodium salt, naproxen potassium salt, naproxen ammonium salt, and mixtures thereof.

17. A method of manufacturing a solid naproxen concentrate, wherein at least 90% of the weight of the naproxen concentrate is naproxen free acid and naproxen alkali salt, comprising: (a) mixing a naproxen alkali salt with at least one acidic substance selected from the group consisting of lactic acid, gluconic acid, citric acid, tartaric acid, hydrochloric acid, phosphoric acid, nitric acid, sulfuric acid, maleic acid, monosodium citrate, disodium citrate, potassium citrate, monosodium tartrate, disodium tartrate, potassium tartrate, aspartic acid, carboxy-methylcellulose, acrylic polymers, methacrylic polymers, and mixtures thereof, to form a composition; and (b) optionally drying the composition to produce a solid naproxen concentrate.

18. The method of claim 17 , wherein the at least one acidic substance is in the form of an aqueous or hydro-alcoholic solution.

19. The method of claim 18 , further comprising sieving the composition prior to drying.

20. The method of claim 19 , further comprising adding water or a water-miscible solvent to the composition.

21. The method of claim 19 , further comprising filling the solid naproxen concentrate in hard shell capsules.

22. A method of preparing a soft gelatin capsule formulation comprising: (a) providing a solid naproxen concentrate consisting of a solid naproxen free acid, a solid naproxen alkali salt, and at least one acidic substance selected from the group consisting of lactic acid, gluconic acid, citric acid, tartaric acid, hydrochloric acid, phosphoric acid, nitric acid, sulfuric acid, maleic acid, monosodium citrate, disodium citrate, potassium citrate, monosodium tartrate, disodium tartrate, potassium tartrate, aspartic acid, carboxy-methylcellulose, acrylic polymers, methacrylic polymers, and mixtures thereof, wherein at least 90% of the weight of the solid naproxen concentrate is naproxen free acid and naproxen alkali salt, and wherein the solid naproxen concentrate does not comprise one or more binders; (b) dissolving the solid naproxen concentrate in a soft gelatin capsule vehicle to form a soft gelatin fill; and (c) encapsulating the soft gelatin fill in a soft gelatin capsule; thereby preparing a soft gelatin capsule formulation.

23. The method of claim 22 , wherein the soft gelatin capsule vehicle is polyethylene glycol.

24. A composition consisting essentially of a solid naproxen concentrate, wherein the solid naproxen concentrate consists of (a) a solid naproxen free acid, (b) a solid naproxen alkali salt, and (c) and at least one acidic substance selected from the group consisting of lactic acid, gluconic acid, citric acid, tartaric acid, hydrochloric acid, phosphoric acid, nitric acid, sulfuric acid, maleic acid, monosodium citrate, disodium citrate, potassium citrate, monosodium tartrate, disodium tartrate, potassium tartrate, aspartic acid, carboxy-methylcellulose, acrylic polymers, methacrylic polymers, and mixtures thereof, and wherein at least 90% of the weight of the solid naproxen concentrate is naproxen free acid and naproxen alkali salt, wherein the naproxen free acid is produced from a solid naproxen alkali salt using at least one acidic substance selected from the group consisting of lactic acid, gluconic acid, citric acid, tartaric acid, hydrochloric acid, phosphoric acid, nitric acid, sulfuric acid, maleic acid, monosodium citrate, disodium citrate, potassium citrate, monosodium tartrate, disodium tartrate, potassium tartrate, aspartic acid, carboxy-methylcellulose, acrylic polymers, methacrylic polymers, and mixtures thereof, and wherein the solid naproxen concentrate does not comprise one or more binders.

25. The composition of claim 24 , wherein at least 95% of the weight of the solid naproxen concentrate is naproxen free acid and naproxen alkali salt.

26. The composition of claim 24 wherein the composition is a hard shell capsule, soft gelatin capsule, liquid suspension, liquid solution, or tablet.

Assignments (2)
RELEASE OF SECURITY INTEREST Recorded Nov 18, 2021
From: ATHYRIUM OPPORTUNITIES II ACQUISITION LP
To: PHARMACEUTICS INTERNATIONAL, INC.
Reel/Frame 058155/0054 →
SECURITY INTEREST Recorded Aug 31, 2016
From: PHARMACEUTICS INTERNATIONAL, INC.
To: ATHYRIUM OPPORTUNITIES II ACQUISITION LP
Reel/Frame 039885/0722 →
Continuity (3)
Continuation 13727264 · Dec 26, 2012
Continuation 12547329 · Aug 25, 2009
Related Publication 20140093562A1 · Apr 3, 2014