# US 11,896,573 B2 · Pharmaceutical compositions and pharmacokinetics of a gamma-hydroxybutyric acid derivative

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- Number: US 11,896,573 B2
- Document ID: US11896573B2
- Status: Granted
- Kind: B2
- Application number: 17/383,253
- Filed: 2021-07-22
- Published: 2022-01-27
- Granted: 2024-02-13
- Earliest claimed: 2020-07-24
- Assignees: Xwpharma Ltd.
- Applicants: Xwpharma Ltd.
- Inventors: William W. Xiang; Jia-Ning Xiang; Daniel M. Canafax
- Web page: https://patentgrep.com/patent/US11896573B2

## CPC

- A61K 31/223: of alpha-aminoacids
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 9/0095: {Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches (A61K9/0007 takes precedence; eatable gels or foams A61K9/0056; oral mucosa adhesive forms A61K9/006)}
- A61K 9/08: Solutions {(composition of solutions A61K47/00)}
- A61K 9/5005: {Wall or coating material}
- A61K 9/5042: {Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose}
- A61K 9/5084: {Mixtures of one or more drugs in different galenical forms, at least one of which being granules, microcapsules or (coated) microparticles according to A61K9/16 or A61K9/50, e.g. for obtaining a specific release pattern or for combining different drugs (tablets containing such a mixture A61K9/2077)}
- A61K 31/19: Carboxylic acids, e.g. valproic acid (salicylic acid A61K31/60)
- A61K 47/12: Carboxylic acids; Salts or anhydrides thereof
- A61K 47/26: Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
- A61P 25/00: Drugs for disorders of the nervous system
- 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

Pharmaceutical compositions of 4-((L-valyl)oxy)butanoic acid and the pharmacokinetics of 4-((L-valyl)oxy)butanoic acid and γ-hydroxybutyric acid following oral administration of the pharmaceutical compositions to healthy subjects are disclosed.

## Claims

### Claim 1

A pharmaceutical composition in a form of an aqueous solution comprising:
from 82 wt % to 92 wt % of 4-((L-valyl)oxy)butanoic acid; and
from 5 wt % to 9 wt % of malic acid, wherein
wt % is based on the total weight of non-aqueous constituents of the aqueous solution; and
the aqueous solution has a pH from 4.0 to 5.0.

### Claim 2 (depends on 1)

The pharmaceutical composition of claim 1, wherein the aqueous solution has a concentration of 4-((L-valyl)oxy)butanoic acid of from 80 mg/mL to 120 mg/mL.

### Claim 3 (depends on 1)

The pharmaceutical composition of claim 1, wherein the aqueous solution comprises from 2 gm to 20 gm of 4-((L-valyl)oxy)butanoic acid.

### Claim 4 (depends on 1)

The pharmaceutical composition of claim 1, wherein the aqueous solution comprises from 6.5 gm to 8.5 gm of 4-((L-valyl)oxy)butanoic acid.

### Claim 5 (depends on 1)

The pharmaceutical composition of claim 1, wherein the aqueous solution further comprises:
from 3 wt % to 7 wt % of a sweetening agent; and
from 0.2 wt % to 0.6 wt % of a flavoring agent;
wherein wt % is based on the total weight of the non-aqueous constituents of the aqueous solution.

### Claim 6 (depends on 1)

The pharmaceutical composition of claim 1, wherein the aqueous solution comprises:
from 84 wt % to 90 wt % of 4-((L-valyl)oxy)butanoic acid; from 6 wt % to 8 wt % of malic acid;
from 4 wt % to 6 wt % of sucralose; and
from 0.3 wt % to 0.5 wt % of flavoring;
wherein wt % is based on the total weight of the non-aqueous constituents in the aqueous solution.

### Claim 7 (depends on 1)

The pharmaceutical composition of claim 1, wherein the aqueous solution comprises coated granules comprising 4-((L-valyl)oxy)butanoic acid.

### Claim 8 (depends on 1)

A method of providing a therapeutically effective amount of γ-hydroxybutyric acid in the plasma of a patient comprising orally administering to a patient in need thereof the pharmaceutical composition of claim 1.

### Claim 9 (depends on 8)

The method of claim 8, wherein the pharmaceutical composition comprises from 2 gm to 20 gm of 4-((L-valyl)oxy)butanoic acid.

### Claim 10 (depends on 1)

A method of treating a disease in a patient in need thereof comprising orally administering the pharmaceutical composition of claim 1 to the patient, wherein the disease is selected from narcolepsy, excessive daytime sleepiness, cataplexy, excessive daytime sleepiness associated with narcolepsy, excessive daytime sleepiness associated with Parkinson's disease, excessive daytime sleepiness associated with multiple sclerosis, cataplexy associated with narcolepsy, fatigue, fatigue associated with Parkinson's disease, fatigue associated with multiple sclerosis, and fibromyalgia.

### Claim 11 (depends on 10)

The method of claim 10, wherein administering comprises administering once per day or twice per day.