IP Library Granted Patent US 9,884,050
Granted Patent B1
US 9,884,050 · App. 15/676,356 · Granted Feb 6, 2018

Inhibition of crystal growth of roflumilast

Inventor: David W. Osborne (Fort Collins, CO)
Assignee: Arcutis, Inc.
A61K31/44A61K9/0014A61K9/145A61K45/06A61K47/10C09K15/06
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Quick Facts
Patent No.
US 9,884,050
App. No.
15/676,356
Granted
Feb 6, 2018
Kind
B1
Abstract

Roflumilast crystals have been shown to increase in size during storage. The size of the roflumilast crystals can affect the bioavailability and efficacy of a pharmaceutical composition. The growth of roflumilast crystals can be inhibited during storage by including hexylene glycol in the composition. The resulting composition has improved bioavailability and efficacy and can be used to inhibit phosphodiesterase 4 in a patient in need of such treatment.

Claims (31)

1. A pharmaceutical composition comprising roflumilast and hexylene glycol.

2. The pharmaceutical composition according to claim 1 , wherein said hexylene glycol is in an amount sufficient to inhibit roflumilast crystal growth or changes in particle size.

3. The pharmaceutical composition according to claim 1 , wherein said hexylene glycol is in an amount of 0.1-20% w/w.

4. The pharmaceutical composition according to claim 1 , wherein said roflumilast is in an amount of 0.005-2% w/w.

5. The pharmaceutical composition according to claim 1 , further comprising pharmaceutically acceptable fillers, carriers and/or excipients.

6. The pharmaceutical composition according to claim 1 , further comprising diethylene glycol monoethyl ether.

7. The pharmaceutical composition according to claim 5 , wherein said pharmaceutically acceptable fillers, carriers and/or excipients are suitable for topical administration.

8. The pharmaceutical composition according to claim 1 , wherein said composition is in the form of an emulsion, suspension, gel, spray, oil, ointment, fatty ointment, cream, paste, foam, transdermal patch or solution.

9. The pharmaceutical composition according to claim 1 , comprising roflumilast, white petrolatum, isopropyl palmitate, cetearyl alcohol, dicetyl phosphate, ceteth-10 phosphate, hexylene glycol, diethylene glycol monoethyl ether, methylparaben, propylparaben, and purified water.

10. The pharmaceutical composition according to claim 9 , comprising the following components:

roflumilast

 0.5% w/w

white petrolatum

10.0% w/w

isopropyl palmitate

 5.0% w/w

cetearyl alcohol, dicetyl phosphate,

10.0% w/w

and ceteth-10 phosphate

hexylene glycol

 2.0% w/w

diethylene glycol monoethyl ether

25.0% w/w

methylparaben

 0.2% w/w

propylparaben

0.05% w/w, and

purified water

q.s. ad 100 (47.25%).

11. The pharmaceutical composition according to claim 3 , wherein said hexylene glycol is in an amount of 0.25-8% w/w.

12. The pharmaceutical composition according to claim 11 , wherein said hexylene glycol is in an amount of 0.5-2% w/w.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2024
From: OSBORNE, DAVID W.
To: ARCUTIS, INC.
Reel/Frame 066560/0442 →
SECURITY INTEREST Recorded Dec 22, 2021
From: ARCUTIS BIOTHERAPEUTICS, INC.
To: SLR INVESTMENT CORP., AS AGENT
Reel/Frame 058463/0187 →
CHANGE OF NAME Recorded Aug 31, 2021
From: ARCUTIS, INC.
To: ARCUTIS BIOTHERAPEUTICS, INC.
Reel/Frame 057394/0812 →
Continuity (1)
Division 15616409 · Jun 7, 2017