# US 10,864,274 B2 · Stabilized efinaconazole formulations

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- Number: US 10,864,274 B2
- Document ID: US10864274B2
- Status: Granted
- Kind: B2
- Application number: 16/435,310
- Filed: 2019-06-07
- Published: 2019-11-28
- Granted: 2020-12-15
- Earliest claimed: 2013-10-03
- Assignees: Bausch Health Ireland Limited
- Applicants: Bausch Health Ireland Limited
- Inventors: Varsha Bhatt; Nayan Desai; Radhakrishnan Pillai
- Web page: https://patentgrep.com/patent/US10864274B2

## CPC

- A61K 47/183: {Amino acids, e.g. glycine, EDTA or aspartame}
- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61K 9/06: Ointments; Bases therefor; {Other semi-solid forms, e.g. creams, sticks, gels (composition of ointments, creams or gels A61K47/00)}
- A61K 9/08: Solutions {(composition of solutions A61K47/00)}
- A61K 31/454: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61P 17/00: Drugs for dermatological disorders
- A61P 31/10: Antimycotics
- A61P 35/00: Antineoplastic agents
- A61K 47/12: Carboxylic acids; Salts or anhydrides thereof
- 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 provides compositions containing efinaconazole, butylated hydroxytoluene, a salt of ethylenediaminetetraacetic acid, and optional citric acid. The compositions exhibit stable color profiles and are useful in the treatment of fungal infections.

## Claims

### Claim 1

A method of treating onychomycosis comprising administering a therapeutically effective amount of an efinaconazole composition to the nails of a patient in need of such treatment,
wherein the efinaconazole composition comprises about 8% to about 12% efinaconazole by weight, water, C12-15 alkyl lactate, diisopropyl adipate, cyclomethicone, ethanol, butylated hydroxytoluene (BHT), a salt of ethylenediaminetetraacetic acid (EDTA), and citric acid,
wherein the amount of BHT is in the range of about 0.01% (w/w) to about 2% (w/w),
wherein the amount of the salt of EDTA is in the range of about 0.0001% (w/w) to about 1.5% (w/w),
wherein the amount of citric acid is in the range of about 0.05% (w/w) to about 0.25% (w/w),
wherein the composition is formulated as a solution, and
wherein the amounts of BHT and the salt of EDTA are sufficient to ensure the composition is (i) colorless upon initial formulation and (ii) colorless or pale yellow after storage for three weeks at a temperature of about 40° C.

### Claim 2 (depends on 1)

The method of claim 1, wherein the amount of efinaconazole in the efinaconazole composition is about 10% (w/w).

### Claim 3 (depends on 1)

The method of claim 1, wherein the amount of the salt of EDTA in the efinaconazole composition is in the range of about 0.0001% (w/w) to about 0.0005% (w/w).

### Claim 4 (depends on 3)

The method of claim 3, wherein the amount of the salt of EDTA in the efinaconazole composition is about 0.00025% (w/w) and the amount of BHT is about 0.1% (w/w).

### Claim 5 (depends on 1)

The method of claim 1, wherein the amount of the salt of EDTA in the efinaconazole composition is in the range of about 0.01% (w/w) to about 1% (w/w).

### Claim 6 (depends on 5)

The method of claim 5, wherein the amount of the salt of EDTA in the efinaconazole composition is about 0.1% (w/w) and the amount of BHT is about 0.1% (w/w).

### Claim 7 (depends on 1)

The method of claim 1, wherein the efinaconazole composition comprises from about 0.075% citric acid (w/w) to about 0.15% citric acid (w/w).

### Claim 8 (depends on 1)

The method of claim 1, comprising:
ethanol in an amount ranging from 50% to 70% by weight,
cyclomethicone in an amount ranging from 10% to 15% by weight,
diisopropyl adipate in an amount ranging from 8% to 15% by weight, and
C12-15 alkyl lactate in an amount ranging from 8% to 15% by weight.

### Claim 9 (depends on 8)

The method of claim 8, wherein the amount of the salt of EDTA in the efinaconazole composition is about 0.00025% (w/w) and the amount of BHT is about 0.1% (w/w).

### Claim 10 (depends on 8)

The method of claim 8, wherein the amount of citric acid in the efinaconazole composition is in the range of about 0.075% (w/w) to about 0.15% (w/w).

### Claim 11 (depends on 9)

The method of claim 9, wherein the amount of citric acid in the efinaconazole composition is in the range of about 0.075% (w/w) to about 0.15% (w/w).

### Claim 12 (depends on 1)

The method of claim 1, wherein the color of the efinaconazole composition is determined by visual inspection.

### Claim 13 (depends on 1)

The method of claim 1, wherein the color of the efinaconazole composition is determined by assessing UV-vis absorbance values.

### Claim 14 (depends on 13)

The method of claim 13, wherein after storage for one month at 65° C. the efinaconazole composition exhibits UV-vis absorbance values of 0.4 absorbance units (AU) or less at 400 nm; 0.1 AU or less at 500 nm; and/or 0.1 AU or less at 600 nm.

### Claim 15 (depends on 1)

The method of claim 1, wherein the efinaconazole composition is applied to the nails of the patient for a period of from about one week to about 12 weeks.

### Claim 16 (depends on 1)

The method of claim 1, wherein the efinaconazole composition is applied to the nails of the patient until the disappearance of the onychomycosis.

### Claim 17 (depends on 1)

The method of claim 1, wherein the efinaconazole composition is applied to the nails of the patient once daily.

### Claim 18 (depends on 1)

The method of claim 1, wherein the efinaconazole composition is applied to the nails of the patient twice daily.