IP Library Granted Patent US 10,583,088
Granted Patent B2
US 10,583,088 · App. 16/002,865 · Granted Mar 10, 2020

Pharmaceutical compositions comprising meloxicam

Inventor: Herriot Tabuteau (New York, NY)
Assignee: AXSOME THERAPEUTICS, INC.
A61K9/2059A61K9/2009A61K9/2086A61K31/4196A61K31/5415
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Quick Facts
Patent No.
US 10,583,088
App. No.
16/002,865
Granted
Mar 10, 2020
Kind
B2
Abstract

Disclosed herein are compositions comprising a drug such as a triptan (e.g. rizatriptan) and/or an NSAID (e.g. meloxicam) in combination with a cyclodextrin and/or a carbonate or a bicarbonate. These compositions may be orally administered, for example, to improve the bioavailability, solubility, or pharmacokinetics of the drug for the treatment of conditions such as pain.

Claims (19)

1. A method of dissolving a combination of meloxicam and rizatriptan in a stomach of a human being, comprising orally administering, to the human being, a solid oral dosage form comprising: a complex of meloxicam with a sulfobutyl ether β-cyclodextrin (SBEβCD), 400 mg to 800 mg of a bicarbonate, and rizatriptan, wherein the dosage form has improved dissolution of meloxicam as compared to a reference dosage form containing: 1) the same amount of meloxicam, and 2) no bicarbonate, wherein the improved dissolution of meloxicam is determined by the following test: adding the dosage form or the reference dosage form to 500 mL of a 0.01 N HCl aqueous solution, stirring at 75 revolutions per minute (RPM) with a USP paddle apparatus II at 37° C., and determining the amount of meloxicam dissolved in the 0.01 N HCl aqueous solution after 15 minutes.

2. The method of claim 1 , wherein about 8 mg to about 13 mg of the rizatriptan is present in the dosage form based upon the weight of the rizatriptan in the free base form.

3. The method of claim 2 , wherein the rizatriptan is present in a salt form in an amount that is a molar equivalent to about 10 mg of the rizatriptan in the free base form.

4. The method of claim 3 , wherein the rizatriptan is present as rizatriptan benzoate.

5. The method of claim 1 , wherein the dosage form contains about 15 mg to about 25 mg of meloxicam.

6. The method of claim 5 , wherein the dosage form contains about 20 mg of meloxicam.

7. The method of claim 1 , wherein the dosage form contains about 100 mg to about 175 mg of the SBEβCD.

8. The method of claim 1 , wherein the dosage form contains about 100 mg to about 140 mg of the SBEβCD.

9. The method of claim 1 , wherein the bicarbonate comprises sodium bicarbonate.

10. The method of claim 1 , wherein the dosage form contains about 450 mg to about 550 mg of the bicarbonate.

11. The method of claim 1 , wherein the dosage form contains about 500 mg of sodium bicarbonate.

12. The method of claim 1 , wherein the bicarbonate improves solubility of meloxicam in the dosage form in a greater extent than a carbonate would in a reference dosage form containing: (1) about same amount of meloxicam, (2) an amount of a carbonate that would achieve same pH as the bicarbonate, and (3) no bicarbonate.

13. The method of claim 1 , wherein the dosage form is orally administered to the human being to treat migraine.

14. The method of claim 13 , wherein the human being has had an inadequate response to a prior treatment for migraine.

15. The method of claim 1 , wherein the human being experiences pain relief sooner than would be experienced as a result of orally administering the reference dosage form containing: 1) the same amount of meloxicam, and 2) no bicarbonate.

16. The method of claim 1 , wherein the dosage form has a rizatriptan solubility property that, as a result of adding the dosage form to 500 mL of a 0.01 N HCl aqueous solution, stirring at 75 revolutions per minute (RPM) with a USP paddle apparatus II at 37° C., and determining the amount of rizatriptan dissolved in the 0.01 N HCl aqueous solution after 15 minutes, at least about 50% of the rizatriptan in the dosage form is dissolved in the 0.01 N HCl aqueous solution.

17. The method of claim 1 , wherein the meloxicam and the rizatriptan have a molar ratio of about 1 to about 2.

18. The method of claim 1 , wherein the T max of meloxicam in the dosage form is less than about 2 hours.

19. The method of claim 1 , wherein the T max of meloxicam in the dosage form is less than about 3 hours.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded May 22, 2025
From: HERCULES CAPITAL, INC.
To: AXSOME THERAPEUTICS, INC.
Reel/Frame 071337/0004 →
SECURITY INTEREST Recorded May 9, 2025
From: AXSOME THERAPEUTICS, INC.; AXSOME MALTA LTD.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 071247/0836 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Sep 25, 2020
From: AXSOME THERAPEUTICS, INC.
To: HERCULES CAPITAL, INC., AS AGENT
Reel/Frame 053941/0491 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 10, 2018
From: TABUTEAU, HERRIOT
To: AXSOME THERAPEUTICS, INC.
Reel/Frame 046310/0414 →
Cited By (13)
US 12,472,255 US 12,472,256 US 12,472,257 US 12,472,258 US 12,478,678 US 12,485,176 US 12,544,383 US 12,551,488 US 12,551,489 US 12,611,413 US 12,616,752 US 12,685,736 US 12,691,123