IP Library Granted Patent US 11,998,639
Granted Patent B2
US 11,998,639 · App. 17/929,396 · Granted Jun 4, 2024

Formulations of (R)-2-amino-3-phenylpropyl carbamate

Inventors: Clark Patrick Allphin (Seattle, WA); Edwin Gerard Walsh (Contarf, IE)
Assignee: AXSOME MALTA LTD.
A61K9/2054A61K9/2027A61K9/2059A61K9/2068A61K31/165A61K31/27
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,998,639
App. No.
17/929,396
Granted
Jun 4, 2024
Kind
B2
Abstract

The present invention relates to immediate release formulations of (R)-2-amino-3-phenylpropyl carbamate and methods of using the same to treat disorders.

Claims (31)

1. A solid pharmaceutical formulation for oral delivery of (R)-2-amino-3-phenylpropyl carbamate, comprising:

a pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate in an amount of about 90-98% by weight of the formulation;

hydroxypropyl cellulose in an amount of 1-5% by weight of the formulation; and

magnesium stearate in an amount of about 0.1-2% by weight of the formulation;

wherein the formulation releases at least 85% of the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate contained therein within a period of less than 15 minutes after administration of the formulation to a subject; and

wherein the formulation exhibits substantially identical dissolution rates of the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate at pH 1.2, pH 4.5, and pH 6.8; and

wherein the formulation does not comprise a disintegrant.

2. The solid pharmaceutical formulation of claim 1 , wherein the pharmaceutical formulation is a tablet.

3. The solid pharmaceutical formulation of claim 1 , wherein the formulation releases at least 95% of the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate contained therein within a period of less than 15 minutes after administration of the formulation to a subject.

4. The solid pharmaceutical formulation of claim 1 , further comprising a coating.

5. The solid pharmaceutical formulation of claim 4 , wherein the coating is a color overcoat.

6. The solid pharmaceutical formulation of claim 1 , wherein the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate is (R)-2-amino-3-phenylpropyl carbamate hydrochloride.

7. The solid pharmaceutical formulation of claim 1 , wherein the formulation comprises about 300 mg of the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate.

8. The solid pharmaceutical formulation of claim 1 , wherein the formulation comprises about 150 mg of the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate.

9. The solid pharmaceutical formulation of claim 1 , wherein the formulation comprises about 75 mg of the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate.

10. The solid pharmaceutical formulation of claim 1 , wherein the formulation comprises about 37.5 mg of the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate.

11. The solid pharmaceutical formulation of claim 1 , comprising a pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate in an amount of about 90-98% by weight of the formulation and a total weight of between about 30 to about 300 mg.

12. The solid pharmaceutical formulation of claim 1 , comprising hydroxypropyl cellulose in an amount of about 1% to about 3% by weight of the formulation.

13. The solid pharmaceutical formulation of claim 1 , comprising magnesium stearate in an amount of about 0.1% to about 1.0% by weight of the formulation.

14. The solid pharmaceutical formulation of claim 1 , comprising hydroxypropyl cellulose in an amount of about 2% by weight of the formulation.

15. The solid pharmaceutical formulation of claim 1 , comprising magnesium stearate in an amount of about 0.5% by weight of the formulation.

16. A method of treating narcolepsy, cataplexy, excessive daytime sleepiness, drug addiction, sexual dysfunction, fatigue, fibromyalgia, attention deficit/hyperactivity disorder, restless legs syndrome, depression, bipolar disorder, or obesity in a subject in need thereof, or promoting smoking cessation in a subject in need thereof, comprising administering to the subject solid pharmaceutical formulation for oral delivery of (R)-2-amino-3-phenylpropyl carbamate, the formulation comprising:

a pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate in an amount of about 90-98% by weight of the formulation;

hydroxypropyl cellulose in an amount of 1-5% by weight of the formulation; and

magnesium stearate in an amount of about 0.1-2% by weight of the formulation;

wherein the formulation releases at least 85% of the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate contained therein within a period of less than 15 minutes after administration of the formulation to a subject; and

wherein the formulation exhibits substantially identical dissolution rates of the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate at pH 1.2, pH 4.5, and pH 6.8; and

wherein the formulation does not comprise a disintegrant.

17. The method claim 16 , wherein the pharmaceutical formulation is a tablet.

18. The method claim 16 , wherein the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate is (R)-2-amino-3-phenylpropyl carbamate hydrochloride.

19. The method of claim 16 , wherein the formulation comprises between about 30 and about 300 mg of the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate.

Assignments (2)
SECURITY INTEREST Recorded May 9, 2025
From: AXSOME THERAPEUTICS, INC.; AXSOME MALTA LTD.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 071247/0836 →
SECURITY INTEREST Recorded Sep 9, 2024
From: AXSOME MALTA LTD
To: HERCULES CAPITAL, INC.
Reel/Frame 068900/0023 →