IP Library Granted Patent US 12,115,142
Granted Patent B2
US 12,115,142 · App. 18/537,318 · Granted Oct 15, 2024

Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics

Inventors: Jordan Dubow (Lyons, FR); Hervé Guillard (Villeurbanne, FR); Claire Mégret (Lyons, FR); Jean-François Dubuisson (Lyons, FR)
Assignee: Flamel Ireland Limited
A61K31/22A61K9/14A61K9/1676A61K9/5015A61K9/5026A61K9/5042A61K9/5078A61K9/5084A61K31/19
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Quick Facts
Patent No.
US 12,115,142
App. No.
18/537,318
Granted
Oct 15, 2024
Kind
B2
Abstract

Modified release formulations of gamma-hydroxybutyrate having improved dissolution and pharmacokinetic properties are provided, and therapeutic uses thereof.

Claims (39)

1. A pharmaceutical formulation for the treatment of narcolepsy or a symptom thereof, comprising:

an immediate release portion comprising gamma-hydroxybutyrate;

a modified release portion comprising gamma-hydroxybutyrate, a polymer carrying free carboxylic groups, and a hydrophobic compound having a melting point equal or greater than 40° C., wherein the weight ratio of the hydrophobic compound to the polymer carrying free carboxylic groups is from 0.6 to 2.5; and

an acidifying agent,

wherein the formulation is designed to be administered orally only once nightly, and

wherein the formulation comprises an amount of gamma-hydroxybutyrate equivalent to from 3.0 g to 12 g of sodium oxybate.

2. The pharmaceutical formulation of claim 1 , wherein the weight ratio of the hydrophobic compound to the polymer carrying free carboxylic groups is from 0.6 to 2.33.

3. The pharmaceutical formulation of claim 1 , wherein the weight ratio of the hydrophobic compound to the polymer carrying free carboxylic groups is about 1.5.

4. The pharmaceutical formulation of claim 1 , wherein the modified release portion comprises a pH triggering release from 5.5 up to 6.97.

5. The pharmaceutical formulation of claim 1 , wherein the modified release portion comprises a pH triggering release from 6.5 up to 6.97.

6. The pharmaceutical formulation of claim 1 , further comprising hydrogenated vegetable oil.

7. A pharmaceutical formulation for the treatment of narcolepsy or a symptom thereof, comprising:

an immediate release portion comprising gamma-hydroxybutyrate;

a modified release portion comprising gamma-hydroxybutyrate and a coating, the coating comprising a methacrylic acid copolymer carrying free carboxylic groups having a pH trigger of from 5.5 to 6.97, and a hydrophobic compound having a melting point equal or greater than 40° C., wherein the weight ratio of the hydrophobic compound to the polymer carrying free carboxylic groups is from 0.4 to 4, wherein the coating is from 10 to 50% of the weight of the particles, and wherein the ratio of gamma-hydroxybutyrate in the immediate release portion and the modified release portion is from 10/90 to 65/35; and

an acidifying agent,

wherein the formulation comprises an amount of gamma-hydroxybutyrate equivalent to from 3.0 g to 12 g of sodium oxybate.

8. The pharmaceutical formulation of claim 7 , wherein the coating further comprises hydrogenated vegetable oil.

9. The pharmaceutical formulation of claim 7 , wherein the formulation comprises an amount of gamma-hydroxybutyrate equivalent to 4.5 g of sodium oxybate and achieves a ratio of AUC 8h to AUC inf of 0.83.

10. The pharmaceutical formulation of claim 7 , wherein the formulation comprises an amount of gamma-hydroxybutyrate equivalent to 6.0 g of sodium oxybate and achieves a ratio of AUC 8h to AUC inf of 0.93.

11. The pharmaceutical formulation of claim 7 , wherein the formulation comprises an amount of gamma-hydroxybutyrate equivalent to 7.5 g of sodium oxybate and achieves a ratio of AUC 8h to AUC inf of 0.89.

12. The pharmaceutical formulation of claim 7 , wherein the immediate release portion comprises immediate release particles comprising gamma-hydroxybutyrate, the modified release portion comprises modified release particles comprising gamma-hydroxybutyrate and the coating.

13. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 7.2% to 58.2%.

14. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 11.0% to 52.9%.

15. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 14.9% to 47.8%.

16. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 18.9% to 47.8%.

17. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 23.1% to 47.8%.

18. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 27.4% to 47.8%.

19. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 31.8% to 47.8%.

20. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 31.8% to 52.9%.

21. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 36.4% to 47.8%.

22. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 5.9% to 63.2%.

23. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 9.1% to 58.1%.

24. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 12.4% to 53.1%.

25. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 19.9% to 53.1%.

26. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 19.6% to 53.1%.

27. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 23.4% to 53.1%.

28. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 27.4% to 53.1%.

29. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 27.4% to 58.1%.

30. The pharmaceutical formulation of claim 12 , wherein the weight percentage of the immediate release particles relative to the total weight of immediate release particles and modified release particles ranges from 31.7% to 53.1%.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 27, 2024
From: DUBOW, JORDAN; GUILLARD, HERVÉ; MÉGRET, CLAIRE; DUBUISSON, JEAN-FRANÇOIS
To: FLAMEL IRELAND LIMITED
Reel/Frame 067858/0944 →
Continuity (11)
Continuation 18231581 · Aug 8, 2023
Continuation 18075980 · Dec 6, 2022
Continuation 17497393 · Oct 8, 2021
Continuation In Part 17178117 · Feb 17, 2021
Continuation In Part 16527633 · Jul 31, 2019
Continuation 16281235 · Feb 21, 2019
Continuation 15655924 · Jul 21, 2017
Provisional Application 62474330 · Mar 21, 2017
Provisional Application 62399413 · Sep 25, 2016
Provisional Application 62365812 · Jul 22, 2016
Related Publication 20240180862A1 · Jun 6, 2024
Cited By (10)
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