# US 11,998,639 B2 · Formulations of (R)-2-amino-3-phenylpropyl carbamate

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- Number: US 11,998,639 B2
- Document ID: US11998639B2
- Status: Granted
- Kind: B2
- Application number: 17/929,396
- Filed: 2022-09-02
- Published: 2023-03-16
- Granted: 2024-06-04
- Earliest claimed: 2016-09-06
- Assignees: Axsome Malta Ltd.
- Applicants: Axsome Malta Ltd.
- Inventors: Clark Patrick Allphin; Edwin Gerard Walsh
- Web page: https://patentgrep.com/patent/US11998639B2

## CPC

- A61K 9/2054: {Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose}
- A61K 9/2013: {Organic compounds, e.g. phospholipids, fats}
- A61K 9/2018: {Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates}
- A61K 9/2027: {obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates}
- A61K 9/2059: {Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin}
- A61K 9/2068: {Compounds of unknown constitution, e.g. material from plants or animals (oils, fats, waxes, shellac A61K9/2013)}
- A61K 31/165: having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K 31/27: of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 21/00: Drugs for disorders of the muscular or neuromuscular system
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/14: for treating abnormal movements, e.g. chorea, dyskinesia
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/24: Antidepressants
- A61P 25/30: for treating abuse or dependence
- A61P 25/34: Tobacco-abuse
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## 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

### Claim 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.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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.

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 4)

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

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 1)

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.

### Claim 8 (depends on 1)

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.

### Claim 9 (depends on 1)

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.

### Claim 10 (depends on 1)

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.

### Claim 11 (depends on 1)

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.

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 1)

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.

### Claim 14 (depends on 1)

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

### Claim 15 (depends on 1)

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

### Claim 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.

### Claim 17 (depends on 16)

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

### Claim 18 (depends on 16)

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

### Claim 19 (depends on 16)

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.