# US 11,439,626 B2 · Controlled release formulations of riluzole and their uses

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- Number: US 11,439,626 B2
- Document ID: US11439626B2
- Status: Granted
- Kind: B2
- Application number: 17/026,181
- Filed: 2020-09-19
- Published: 2021-03-25
- Granted: 2022-09-13
- Earliest claimed: 2019-09-20
- Assignees: Icahn School of Medicine at Mount Sinai
- Applicants: Icahn School of Medicine at Mount Sinai
- Inventors: Ana Pereira
- Web page: https://patentgrep.com/patent/US11439626B2

## CPC

- A61K 31/428: condensed with carbocyclic rings
- A61K 9/0004: {Osmotic delivery systems; Sustained release driven by osmosis, thermal energy or gas}
- A61K 9/0065: {Forms with gastric retention, e.g. floating on gastric juice, adhering to gastric mucosa, expanding to prevent passage through the pylorus}
- A61K 9/1676: {having a drug-free core with discrete complete coating layer containing drug (adsorbates of liquid drug formulations on inert powders without simultaneous granulation step A61K9/141; with further drug-free outer coating A61K9/5078; drug conjugated to non-active particles A61K47/6921)}
- A61K 9/2031: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers}
- A61K 9/2054: {Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose}
- A61K 9/5078: {with drug-free core}
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/22: Anxiolytics
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61K 9/5026: {obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates}
- A61K 9/5042: {Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose}
- 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

Disclosed herein are controlled release compositions comprising riluzole and the uses thereof.

## Claims

### Claim 1

A pharmaceutical composition comprising from about 75 mg up to about 300 mg of a compound selected from the group consisting of: riluzole; N-methyl-2-(methylamino)-N-(2-oxo-2-((6-(trifluoromethoxy)benzo[d]thiazol-2-yl)amino)ethyl)acetamide; 2-(ethylamino)-N-methyl-N-(2-oxo-2-((6-(trifluoromethoxy)benzo[d]thiazol-2-yl)amino)ethyl)acetamide; 2-(isopropylamino)-N-methyl-N-(2-oxo-2-((6-(trifluoromethoxy)benzo[d]thia-zol-2-yl)amino)ethyl)acetamide; 2-(tert-butylamino)-N-methyl-N-(2-oxo-2-((6-(trifluoromethoxy)benzo[d]thi-azol-2-yl)amino)ethyl)acetamide; or a pharmaceutically acceptable salt thereof, wherein the pharmaceutical composition provides a Cmax at steady state of less than about 0.3 mcg/mL for at least about 24 hours.

### Claim 2 (depends on 1)

A pharmaceutical composition of claim 1, wherein the pharmaceutical composition comprises riluzole and provides a Cmin at steady state of at least about 0.04 mcg/mL for at least about 24 hours.

### Claim 3 (depends on 2)

A pharmaceutical composition of claim 2, wherein the pharmaceutical composition comprises riluzole and provides an AUC at steady state of from about 1.5 mcg*h/mL to about 4 mcg*h/mL for at least about 24 hours.

### Claim 4 (depends on 3)

The pharmaceutical composition of claim 3, wherein the AUC at steady state is about 2.5 mcg*h/mL at least about 24 hours.

### Claim 5 (depends on 1)

The pharmaceutical composition of claim 1, wherein the pharmaceutical composition is formulated to be administered once a day.

### Claim 6 (depends on 2)

The pharmaceutical composition of claim 2, wherein the pharmaceutical composition is formulated to be administered once a day.

### Claim 7 (depends on 3)

The pharmaceutical composition of claim 3, wherein the pharmaceutical composition is formulated to be administered once a day.

### Claim 8 (depends on 1)

The pharmaceutical composition of claim 1, wherein the pharmaceutical composition is formulated to be taken without food.

### Claim 9 (depends on 3)

The pharmaceutical composition of claim 3, wherein the pharmaceutical composition is formulated to be taken without food.

### Claim 10 (depends on 1)

The pharmaceutical composition of claim 1, wherein the pharmaceutical composition is formulated to reduce liver toxicity compared to 50 mg of an immediate release form of riluzole given twice a day.

### Claim 11 (depends on 3)

The pharmaceutical composition of claim 3, wherein the pharmaceutical composition is formulated to reduce liver toxicity compared to 50 mg of an immediate release form of riluzole given twice a day.

### Claim 12 (depends on 1)

A method of treating Alzheimer's disease, amyotrophic lateral sclerosis, obsessive compulsive disorder, or spinocerebellar ataxia, comprising administering to a subject in need thereof a composition of claim 1.

### Claim 13 (depends on 3)

A method of treating Alzheimer's disease, amyotrophic lateral sclerosis, obsessive compulsive disorder, or spinocerebellar ataxia, comprising administering to a subject in need thereof a composition of claim 3.

### Claim 14 (depends on 5)

A method of treating Alzheimer's disease, amyotrophic lateral sclerosis, obsessive compulsive disorder, or spinocerebellar ataxia, comprising administering to a subject in need thereof a composition of claim 5.

### Claim 15 (depends on 7)

A method of treating Alzheimer's disease, amyotrophic lateral sclerosis, obsessive compulsive disorder, or spinocerebellar ataxia, comprising administering to a subject in need thereof a composition of claim 7.

### Claim 16 (depends on 15)

The method of claim 15, wherein the composition comprises about 100 to about 125 mg of riluzole.

### Claim 17 (depends on 16)

The method of claim 16, wherein the subject is suffering from Alzheimer's disease.

### Claim 18 (depends on 16)

The method of claim 16, wherein the subject is suffering from amyotrophic lateral sclerosis.

### Claim 19 (depends on 16)

The method of claim 16, wherein the subject is suffering from obsessive compulsive disorder.

### Claim 20 (depends on 16)

The method of claim 16, wherein the subject is suffering from spinocerebellar ataxia.