Granted Patent B2

US 12,390,419 · App. 18/643,086 · Granted Aug 19, 2025

Inventors: Clark Patrick Allphin (Seattle, WA); Edwin Gerard Walsh (Dublin, IE)

Assignee: AXSOME MALTA LTD.

A61K9/2054A61K9/2027A61K9/2059A61K9/2068A61K31/165A61K31/27

Abstract

Claims (30)

1. An immediate release compressed tablet 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;

at least one binder in an amount of 1-5% by weight of the formulation; and

at least one lubricant in an amount of about 0.1-2% by weight of the tablet;

wherein the tablet 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;

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 tablet comprises about 300 mg of (R)-2-amino-3-phenylpropyl carbamate, about 150 mg of (R)-2-amino-3-phenylpropyl carbamate, about 75 mg of (R)-2-amino-3-phenylpropyl carbamate, or about 37.5 mg of (R)-2-amino-3-phenylpropyl carbamate.

2. The immediate release compressed tablet of claim 1 , wherein the tablet 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.

3. The immediate release compressed tablet of claim 1 , wherein the tablet does not comprise a disintegrant.

4. The immediate release compressed tablet of claim 1 , wherein the at least one binder is selected from at least one of hydroxypropyl cellulose, ethylcellulose, hydroxypropyl methylcellulose, polyvinyl alcohol, hydroxyethyl cellulose, povidone, copovidone, pregelatinized starch, dextrin, gelatin, maltodextrin, starch, zein, acacia, alginic acid, carbomers (cross-linked polyacrylates), polymethacrylates, sodium carboxymethylcellulose, guar gum, hydrogenated vegetable oil (type 1), methylcellulose, magnesium aluminum silicate, and sodium alginate.

5. The immediate release compressed tablet of claim 1 , wherein the at least one lubricant is selected from at least one of magnesium stearate, stearic acid, calcium stearate, hydrogenated castor oil, hydrogenated vegetable oil, light mineral oil, magnesium stearate, mineral oil, polyethylene glycol, sodium benzoate, sodium stearyl fumarate, and zinc stearate.

6. The immediate release compressed tablet 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 tablet;

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

magnesium stearate in an amount of about 0.1-2% by weight of the tablet.

7. The immediate release compressed tablet of claim 1 , further comprising a coating.

8. The immediate release compressed tablet of claim 7 , wherein the coating is a color overcoat.

9. The immediate release compressed tablet of claim 1 , wherein the tablet is free of other excipients.

10. The immediate release compressed tablet of claim 7 , wherein the tablet is free of other excipients.

11. The immediate release compressed tablet of claim 1 , wherein the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate is (R)-2-amino-3-phenylpropyl carbamate hydrochloride.

12. The immediate release compressed tablet of claim 1 , comprising hydroxypropyl cellulose in an amount of about 1-3% by weight of the tablet.

13. The immediate release compressed tablet of claim 1 , comprising magnesium stearate in an amount of about 0.1% to about 1.0% by weight of the tablet.

14. 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 an immediate release compressed tablet 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;

at least one binder in an amount of 1-5% by weight of the formulation; and

at least one lubricant in an amount of about 0.1-2% by weight of the tablet;

wherein the tablet 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;

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 tablet comprises about 300 mg of (R)-2-amino-3-phenylpropyl carbamate, about 150 mg of (R)-2-amino-3-phenylpropyl carbamate, about 75 mg of (R)-2-amino-3-phenylpropyl carbamate, or about 37.5 mg of (R)-2-amino-3-phenylpropyl carbamate.

15. The method of claim 14 , wherein the pharmaceutically acceptable salt of (R)-2-amino-3-phenylpropyl carbamate is (R)-2-amino-3-phenylpropyl carbamate hydrochloride.

Assignments (1)

Continuity (7)

References Cited (164)