IP Library Granted Patent US 11,026,898
Granted Patent B2
US 11,026,898 · App. 16/518,338 · Granted Jun 8, 2021

Eutectic formulations of cyclobenzaprine hydrochloride

Inventors: Seth Lederman (South Dartmouth, MA); Marino Nebuloni (Rho, IT)
Assignee: Tonix Pharma Holdings Limited
A61K31/135A61K9/1623A61K9/2018A61P21/00A61P21/02A61P25/00A61P25/04A61P25/08A61P25/20A61P25/22A61P25/24
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Quick Facts
Patent No.
US 11,026,898
App. No.
16/518,338
Granted
Jun 8, 2021
Kind
B2
Abstract

The present invention relates to pharmaceutical compositions and methods of manufacturing the same, comprising a eutectic of Cyclobenzaprine HCl and mannitol.

Claims (23)

1. A pharmaceutical composition comprising a eutectic of δ-mannitol and Cyclobenzaprine HCl, wherein the eutectic comprises 65%±2% Cyclobenzaprine HCl and 35%±2% δ-mannitol by weight.

2. The pharmaceutical composition of claim 1 , wherein the Cyclobenzaprine HCl is micronized Cyclobenzaprine HCl.

3. The pharmaceutical composition of claim 1 , further comprising a basifying agent.

4. The pharmaceutical composition of claim 3 , wherein the basifying agent is K 2 HPO 4 , Na 2 HPO 4 , or anhydrous trisodium citrate.

5. The pharmaceutical composition of claim 1 , wherein said composition comprises granules.

6. The pharmaceutical composition of claim 5 , wherein said granules comprise Cyclobenzaprine HCl and δ mannitol.

7. A method of manufacturing the pharmaceutical composition of claim 1 , comprising mixing Cyclobenzaprine HCl and mannitol in the presence of a solvent.

8. The method of claim 7 , wherein the mannitol is β mannitol or δ mannitol.

9. The method of claim 7 , wherein said mixing is wet granulation mixing.

10. The method of claim 7 , wherein the solvent is water, an alcohol or a mixture thereof.

11. The method of claim 10 , wherein said alcohol is methanol or ethanol.

12. The method of claim 9 , further comprising drying the mixture after said wet granulation.

13. The method of claim 12 , wherein said wet granulation and drying are repeated one or more times.

14. The method of claim 9 , further comprising crystallizing the Cyclobenzaprine HCl-mannitol mixture after said wet granulation.

15. The method of claim 14 , wherein said wet granulation and crystallization are repeated one or more times.

16. A method of manufacturing the pharmaceutical composition of claim 1 comprising fluid bed drying a mixture of Cyclobenzaprine HCl, mannitol, and a solvent.

17. The method of claim 16 , wherein the mannitol is β mannitol or δ mannitol.

18. The method of claim 16 , wherein the solvent is water, an alcohol or a mixture thereof.

19. The method of claim 18 , wherein the alcohol is methanol or ethanol.

20. The method of claim 16 , wherein the Cyclobenzaprine HCl is dissolved in the solvent and sprayed onto β mannitol particles inside a fluid bed dryer.

21. The pharmaceutical composition of claim 1 , wherein the δ-mannitol eutectic melts at 134° C.±3° C.

22. The method of claim 7 , wherein Cyclobenzaprine HCl is mixed with β mannitol.

23. The method of claim 22 , wherein the β mannitol converts to δ mannitol.

Assignments (5)
NOVATION AGREEMENT Recorded Jul 8, 2024
From: TONIX PHARMA HOLDINGS LIMITED
To: TONIX PHARMA LIMITED
Reel/Frame 068217/0592 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 22, 2019
From: NEBULONI, MARINO
To: REDOX SRL
Reel/Frame 049822/0015 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 22, 2019
From: TONIX PHARMACEUTICALS, INC.
To: TONIX PHARMA HOLDINGS LIMITED
Reel/Frame 049822/0044 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 22, 2019
From: REDOX SRL
To: TONIX PHARMACEUTICALS, INC.
Reel/Frame 049825/0623 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 22, 2019
From: LEDERMAN, SETH
To: TONIX PHARMACEUTICALS, INC
Reel/Frame 049825/0637 →
Continuity (3)
Continuation 15511287
Provisional Application 62052238 · Sep 18, 2014
Related Publication 20190336458A1 · Nov 7, 2019