# US 11,026,944 B2 · Compositions and methods for treating insomnia

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- Number: US 11,026,944 B2
- Document ID: US11026944B2
- Status: Granted
- Kind: B2
- Application number: 16/819,341
- Filed: 2020-03-16
- Published: 2020-08-27
- Granted: 2021-06-08
- Earliest claimed: 2014-10-23
- Assignees: Eisai R&D Management Co., Ltd.
- Applicants: Eisai R&D Management Co., Ltd.
- Inventors: Margaret Moline; Gina Pastino; Yurie Akimoto; Yasuhiro Zaima; Nobuya Suzuki; Nobuo Yoshida
- Web page: https://patentgrep.com/patent/US11026944B2

## CPC

- A61K 31/506: not condensed and containing further heterocyclic rings
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 9/2018: {Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates}
- A61K 9/2054: {Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose}
- A61K 9/48: Preparations in capsules, e.g. of gelatin, of chocolate {(A61K9/0004 takes precedence; bite capsules A61K9/0056)}
- A61K 9/4858: {Organic compounds}
- A61K 9/4866: {Organic macromolecular compounds}
- A61P 25/20: Hypnotics; Sedatives
- 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

In the present invention, compound such as (1R,2S)-2-(((2,4-dimethylpyrimidin-5-yl)oxy)methyl)-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl) cyclopropanecarboxamide have been found to be potent orexin receptor antagonists, and may be useful in the treatment of sleep disorders such as insomnia, as well as for other therapeutic uses.

## Claims

### Claim 1

A dosage form comprising a therapeutically effective amount of compound A, wherein said therapeutically effective amount is a single daily dose ranging from about 2.5 mg to about 10 mg, wherein said dosage form provides a dissolution rate of 85% or more in a dissolution medium (0.1 mol/L hydrochloric acid containing 0.5% polysorbate 80, 900 mL, 37±0.5° C.) within 30 minutes from the onset of a dissolution study using Apparatus 2 (Paddle Apparatus, paddle speed; 75 rpm) according to the procedure for immediate-release dosage form in 6.10 Dissolution test of JP16 or <711>Dissolution of USP37, wherein said compound A is (1R,2S)-2-(((2,4-dimethylpyrimidin-5-yl)oxy)methyl)-2-(3-fluorophenyl)-N-(5-fluoropyridine-2-yl)cyclopropanecarboxamide represented by the following formula:

### Claim 2 (depends on 1)

The dosage form of claim 1, wherein said dosage form provides a dissolution rate of 85% or more in a dissolution medium (0.1 mol/L hydrochloric acid, 900 mL, 37±0.5° C.) within 15 minutes from the onset of a dissolution study using Apparatus 2 (Paddle Apparatus, paddle speed; 50 rpm) according to the procedure for immediate-release dosage form in 6.10 Dissolution test of JP16 or <711>Dissolution of USP37.

### Claim 3 (depends on 1)

The dosage form of claim 1, wherein said dosage form comprises lactose as a pharmaceutically acceptable excipient.

### Claim 4 (depends on 1)

The dosage form of claim 1, wherein said dosage form comprises low-substituted hydroxypropyl cellulose as a pharmaceutically acceptable excipient.

### Claim 5 (depends on 1)

The dosage form of claim 1, wherein said dosage form comprises lactose and low-substituted hydroxypropyl cellulose as pharmaceutically acceptable excipients.