IP Library Granted Patent US 9,895,359
Granted Patent B1
US 9,895,359 · App. 15/616,409 · Granted Feb 20, 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 9,895,359
App. No.
15/616,409
Granted
Feb 20, 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 patient in need of such treatment.

Claims (45)

1. A method for inhibiting roflumilast crystal growth or changes in particle size in a composition, comprising including hexylene glycol in a composition comprising roflumilast.

2. The method according to claim 1 , wherein said composition comprises suspended roflumilast particles.

3. The method according to claim 2 , wherein changes in the size of the suspended roflumilast particles is inhibited during storage for six weeks at 20-26° C.

4. The method according to claim 1 , wherein said hexylene glycol is added in an amount of 0.1-20% w/w.

5. The method according to claim 4 , wherein said hexylene glycol is added in an amount of 0.5-2% w/w.

6. The method according to claim 1 , wherein said roflumilast composition comprises 0.005-2% roflumilast.

7. The method according to claim 1 , wherein said roflumilast composition is selected from the group consisting of an oil in water emulsion, a thickened aqueous gel, a thickened hydroalcoholic gel, a hydrophilic gel, and a hydrophilic or hydrophobic ointment.

8. The method according to claim 1 , wherein said roflumilast composition further comprises at least one additional component selected from the group consisting of a solvent, moisturizer, surfactant or emulsifier, polymer or thickener, antifoaming agent, preservative, antioxidant, sequestering agent, stabilizer, buffer, pH adjusting solution, skin penetration enhancer, film former, dye, pigment, and fragrance.

9. The method according to claim 1 , wherein said roflumilast composition further comprises an additional active agent selected from the group consisting of anthralin, azathioprine, tacrolimus, coal tar, methotrexate, methoxsalen, salicylic acid, ammonium lactate, urea, hydroxyurea, 5-fluorouracil, propylthouracil, 6-thioguanine, sulfasalazine, mycophenolate mofetil, fumaric acid esters, corticosteroids, corticotropin, vitamin D analogues, acitretin, tazarotene, cyclosporine, resorcinol, colchicine, adalimumab, ustekinumab, infliximab, bronchodialators, and antibiotics.

10. The method according to claim 1 wherein said hexylene glycol is added to said composition prior to storage.

11. The method according to claim 1 , wherein said composition comprises one or more carriers suitable for topical, parenteral or pulmonary administration.

12. The method according to claim 1 , wherein said composition comprises one or more carriers suitable for topical administration.

13. The method according to claim 1 , further comprising adding diethylene glycol monoethyl ether to said composition.

14. The method according to claim 1 , wherein said composition comprises roflumilast, white petrolatum, isopropyl palmitate, cetearyl alcohol, dicetyl phosphate, ceteth-10 phosphate, hexylene glycol, diethylene glycol monoethyl ether, methylparaben, propylparaben, and purified water.

15. The method according to claim 14 , wherein the composition comprises:

roflumilast

0.5%

w/w

white petrolatum

10.0%

w/w

isopropyl palmitate

5.0%

w/w

cetearyl alcohol, dicetyl

10.0%

w/w

phosphate, and

ceteth-10 phosphate

hexylene glycol

2.0%

w/w

diethylene glycol

25.0%

w/w

monoethyl ether

methylparaben

0.2%

w/w

propylparaben

0.05%

w/w, and

purified water

q.s. ad 100 (47.25%).

16. The method according to claim 4 , wherein said hexylene glycol is added in an amount of 0.25-8% w/w.

Assignments (3)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 7, 2017
From: OSBORNE, DAVID W.
To: ARCUTIS, INC.
Reel/Frame 042638/0206 →