# US 12,005,052 B2 · Topical roflumilast formulation having improved delivery and plasma half-life

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- Number: US 12,005,052 B2
- Document ID: US12005052B2
- Status: Granted
- Kind: B2
- Application number: 18/353,869
- Filed: 2023-07-17
- Published: 2023-11-16
- Granted: 2024-06-11
- Earliest claimed: 2017-06-07
- Assignees: Arcutis Biotherapeutics, Inc.
- Applicants: ARCUTIS BIOTHERAPEUTICS, Inc.
- Inventors: David W. Osborne
- Web page: https://patentgrep.com/patent/US12005052B2

## CPC

- A61K 31/44: Non condensed pyridines; Hydrogenated derivatives thereof
- 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 9/10: Dispersions; Emulsions
- A61K 9/107: Emulsions {; Emulsion preconcentrates; Micelles (composition of emulsions A61K47/00)}
- A61K 9/12: Aerosols; Foams {(A61K9/0043, A61K9/0056, A61K9/006, A61K9/0073 take precedence; spray-films A61K9/7015)}
- A61K 9/122: {Foams; Dry foams (edible foams A61K9/0056)}
- A61K 9/7015: {Drug-containing film-forming compositions, e.g. spray-on}
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61K 47/06: Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- A61K 47/24: containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
- A61P 17/06: Antipsoriatics
- 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 is directed to methods for improving the therapeutic outcome of treatment with roflumilast. The therapeutic outcome is improved by consistent delivery and/or a longer plasma half-life of a topically administered roflumilast composition. The roflumilast composition preferably includes dicetyl phosphate, ceteth-10 phosphate, diethylene glycol I monoethyl ether, and/or hexylene glycol.

## Claims

### Claim 1

A pharmaceutical composition for topical administration comprising:
(i) roflumilast, wherein the roflumilast is in an amount of 0.05-1.0% w/w;
(ii) water;
(iii) diethylene glycol monoethyl ether; and
(iv) an emulsifier blend comprising cetostearyl alcohol, dicetyl phosphate and ceteth-10 phosphate;
wherein the plasma half-life of the roflumilast is between 3 and 5 days after topical administration of the composition.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein said composition comprises about 10% w/w of said emulsifier blend.

### Claim 3 (depends on 1)

The composition according to claim 1, wherein said composition comprises about 25% w/w diethylene glycol monoethyl ether.

### Claim 4 (depends on 1)

The composition according to claim 1, wherein said composition comprises w/w roflumilast.

### Claim 5 (depends on 4)

The composition according to claim 4, wherein said composition comprises about 10% w/w of said emulsifier blend.

### Claim 6 (depends on 4)

The composition according to claim 4, wherein said composition comprises about 25% diethylene glycol monoethyl ether.

### Claim 7

A pharmaceutical composition for topical administration comprising:
(i) roflumilast in an amount of 0.05-1.0% w/w;
(ii) water qs ad 100% w/w;
(iii) diethylene glycol monoethyl ether in an amount of 10-30% w/w; and
(iv) an emulsifier blend comprising cetostearyl alcohol, dicetyl phosphate and ceteth-10 phosphate in an amount of 1.0-25% w/w;
wherein the composition is a foam or cream.

### Claim 8 (depends on 7)

The composition according to claim 7, wherein said composition is a foam, and wherein said composition comprises 25% w/w diethylene glycol monoethyl ether, 2% w/w emulsifier blend, white petrolatum, and isopropyl palmitate.

### Claim 9 (depends on 7)

The composition according to claim 7, wherein said composition is a cream, and wherein said composition comprises 25% w/w diethylene glycol monoethyl ether, 10% w/w emulsifier blend, 10.0% w/w white petrolatum, and 5.0% w/w isopropyl palmitate.