# US 11,439,597 B2 · Formulations of (R)-2-amino-3-phenylpropyl carbamate

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,439,597 B2
- Document ID: US11439597B2
- Status: Granted
- Kind: B2
- Application number: 17/154,336
- Filed: 2021-01-21
- Published: 2021-07-08
- Granted: 2022-09-13
- 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/US11439597B2

## 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 (APC) consisting of
i) a pharmaceutically acceptable salt of APC containing 75 mg of APC;
ii) a binder in an amount not exceeding 5% by weight of the formulation;
iii) a lubricant in an amount of about 0.1-2% by weight of the formulation; and
iv) an optional coating;
wherein the formulation releases at least 85% of the pharmaceutically acceptable salt of APC in less than 15 minutes after oral administration of the formulation to a subject; and wherein the formulation exhibits substantially identical dissolution rates of the pharmaceutically acceptable salt of APC at pH 1.2, pH 4.5, and pH 6.8;
wherein the binder is selected from hydroxypropyl cellulose, hydroxypropyl methylcellulose, and povidone; and
wherein the lubricant is selected from magnesium stearate, calcium stearate, and sodium stearyl fumarate.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

The solid pharmaceutical formulation of claim 1, wherein
(R)-2-amino-3-phenylpropyl carbamate or a pharmaceutically acceptable salt thereof is in an amount of about 90-98% by weight of the formulation;
hydroxypropyl cellulose is in an amount of about 1-5% by weight of the formulation; and
magnesium stearate is in an amount of about 0.1-2% by weight of the formulation.

### Claim 6 (depends on 1)

The solid pharmaceutical formulation of claim 1, wherein
(R)-2-amino-3-phenylpropyl carbamate or a pharmaceutically acceptable salt thereof is in an amount of about 90-98% by weight of the formulation;
hydroxypropyl cellulose is in an amount of about 2% by weight of the formulation; and
magnesium stearate is in an amount of about 0.5% by weight of the formulation.

### Claim 7 (depends on 1)

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

### Claim 8 (depends on 1)

The solid pharmaceutical formulation of claim 1, wherein the coating is present.

### Claim 9 (depends on 8)

The solid pharmaceutical formulation of claim 8, wherein the coating is a color overcoat.

### Claim 10

A solid pharmaceutical formulation for oral delivery of (R)-2-amino-3-phenylpropyl carbamate (APC) consisting of
i) a pharmaceutically acceptable salt of APC containing 150 mg of APC;
ii) a binder in an amount of about 1-5% by weight of the formulation;
iii) a lubricant in an amount of about 0.1-2% by weight of the formulation; and
iv) an optional coating;
wherein the formulation releases at least 85% of the pharmaceutically acceptable salt of APC in less than 15 minutes after oral administration of the formulation to a subject; and wherein the formulation exhibits substantially identical dissolution rates of the pharmaceutically acceptable salt of APC at pH 1.2, pH 4.5, and pH 6.8;
wherein the binder is selected from hydroxypropyl cellulose, hydroxypropyl methylcellulose, and povidone:
wherein the lubricant is selected from magnesium stearate, calcium stearate, and sodium stearyl fumarate, and sodium stearyl fumarate.

### Claim 11 (depends on 10)

The solid pharmaceutical formulation claim 10, wherein the formulation releases at least 95% of the (R)-2-amino-3-phenylpropyl carbamate or a pharmaceutically acceptable salt thereof contained therein within a period of less than 15 minutes after administration of the formulation to a subject.

### Claim 12 (depends on 10)

The solid pharmaceutical formulation of claim 10, wherein hydroxypropyl cellulose is in an amount of about 1-3% by weight of the formulation.

### Claim 13 (depends on 10)

The solid pharmaceutical formulation of claim 10, wherein magnesium stearate is in an amount of about 0% to about 1.0% by weight of the formulation.

### Claim 14 (depends on 10)

The solid pharmaceutical formulation of claim 10, wherein
(R)-2-amino-3-phenylpropyl carbamate or a pharmaceutically acceptable salt thereof is in an amount of about 90-98% by weight of the formulation;
hydroxypropyl cellulose is in an amount of about 1-5% by weight of the formulation; and
magnesium stearate is in an amount of about 0.1-2% by weight of the formulation.

### Claim 15 (depends on 10)

The solid pharmaceutical formulation of claim 10, wherein
(R)-2-amino-3-phenylpropyl carbamate or a pharmaceutically acceptable salt thereof is in an amount of about 90-98% by weight of the formulation;
hydroxypropyl cellulose is in an amount of about 2% by weight of the formulation; and
magnesium stearate is in an amount of about 0.5% by weight of the formulation.

### Claim 16 (depends on 10)

The solid pharmaceutical formulation of claim 10, wherein the (R)-2-amino-3-phenylpropyl carbamate or a pharmaceutically acceptable salt thereof is (R)-2-amino-3-phenylpropyl carbamate hydrochloride.

### Claim 17 (depends on 10)

The solid pharmaceutical formulation of claim 10, wherein the coating is present.

### Claim 18 (depends on 10)

The solid pharmaceutical formulation of claim 10, wherein the coating is a color overcoat.