IP Library Granted Patent US 12,042,487
Granted Patent B2
US 12,042,487 · App. 18/353,870 · Granted Jul 23, 2024

Method for reducing side effects from administration of phosphodiesterase-4 inhibitors

Inventor: David W. Osborne (Fort Collins, CO)
Assignee: ARCUTIS BIOTHERAPEUTICS, INC.
A61K31/44A61K9/0014A61K9/06A61K9/122A61K47/10A61K47/24A61K45/06
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Quick Facts
Patent No.
US 12,042,487
App. No.
18/353,870
Granted
Jul 23, 2024
Kind
B2
Abstract

A method for altering the PK profile of a pharmaceutical formulation containing a PDE-4 inhibitor, such as roflumilast, to reduce the spike in Cmax. The spike in Cmax is reduced by topically administering the PDE-4 inhibitor in combination with one or more phosphate ester surfactants. Reducing the spike in Cmax will reduce gastrointestinal side effects and result in better patient compliance.

Claims (48)

1. A pharmaceutical composition for topical administration comprising:

(i) roflumilast, wherein the roflumilast is in an amount of 0.05-1% w/w;

(ii) a phosphate ester surfactant blend comprising cetostearyl alcohol, dicetyl phosphate and ceteth-10 phosphate, wherein the phosphate ester surfactant blend is in an amount of 1.0-25% w/w; and

(iii) water;

wherein the C max of roflumilast from the topical composition is reduced relative to an oral roflumilast formulation marketed under the trademark DALIRESP®.

2. The composition of claim 1 , wherein said composition further comprises diethylene glycol monoethyl ether.

3. The composition of claim 1 , wherein said roflumilast is in an amount of 0.3% w/w.

4. The composition of claim 1 , wherein said roflumilast is in an amount of 0.15% w/w.

5. The composition of claim 1 , wherein said roflumilast is in an amount of 0.05% w/w.

6. The composition of claim 1 , wherein said phosphate ester surfactant blend is in an amount sufficient to decrease a slope of the plasma concentration curve of the roflumilast between administration of said composition and Cmax.

7. The composition of claim 1 , wherein the plasma concentration curve of the roflumilast has no spike at C max .

8. The composition of claim 1 , wherein said roflumilast is in an amount of 0.3% w/w, wherein said phosphate ester surfactant blend is in an amount of about 5% to about 15% w/w, and wherein said composition comprises diethylene glycol monoethyl ether in an amount of 10% to 40% w/w.

9. The composition of claim 1 , wherein said roflumilast is in an amount of 0.15% w/w, wherein said phosphate ester surfactant blend is in an amount of about 5% to about 15% w/w, and wherein said composition comprises diethylene glycol monoethyl ether in an amount of 10% to 40% w/w.

10. The composition of claim 1 , wherein said roflumilast is in an amount of 0.05% w/w, wherein said phosphate ester surfactant blend is in an amount of about 5% to about 15% w/w, and wherein said composition comprises diethylene glycol monoethyl ether in an amount of 10% to 40% w/w.

11. A pharmaceutical composition for topical administration comprising:

(i) roflumilast, wherein the roflumilast is in an amount of 0.05-1% w/w;

(ii) a phosphate ester surfactant blend comprising cetostearyl alcohol, dicetyl phosphate and ceteth-10 phosphate, wherein the phosphate ester surfactant blend is in an amount of 1.0-25% w/w;

wherein the peak to trough ratio of roflumilast blood plasma concentration is less than 2 at steady state.

12. The composition of claim 11 , wherein the difference in a trough and an adjacent peak of the plasma concentration curve of the roflumilast at steady state is between about 4% and about 7%.

13. The composition of claim 11 , wherein the plasma concentration of the roflumilast plateaus after C max for 24 hours following administration.

14. The composition of claim 11 , wherein the peak to trough ratio is approximately 1 at steady state.

15. The composition of claim 11 , wherein said phosphate ester surfactant blend is in an amount of 5% to 15% w/w.

16. The composition of claim 15 , wherein said phosphate ester surfactant blend is in an amount of about 10% w/w.

17. The composition of claim 11 , wherein said composition comprises diethylene glycol monoethyl ether.

18. The composition of claim 17 , wherein said diethylene glycol monoethyl ether is in an amount of 10% to 40% w/w.

19. The composition of claim 11 , wherein said roflumilast is in an amount of 0.3% w/w, wherein said phosphate ester surfactant blend is in an amount of about 5% to about 15% w/w, and wherein said composition comprises diethylene glycol monoethyl ether in an amount of 10% to 40% w/w.

20. The composition of claim 11 , wherein said roflumilast is in an amount of 0.15% w/w, wherein said phosphate ester surfactant blend is in an amount of about 5% to about 15% w/w, and wherein said composition comprises diethylene glycol monoethyl ether in an amount of 10% to 40% w/w.

21. The composition of claim 11 , wherein said roflumilast is in an amount of 0.05% w/w, wherein said phosphate ester surfactant blend is in an amount of about 5% to about 15% w/w, and wherein said composition comprises diethylene glycol monoethyl ether in an amount of 10% to 40% w/w.

22. A pharmaceutical composition for topical administration comprising:

(i) roflumilast, wherein the roflumilast is in an amount of 0.05-1% w/w;

(ii) at least one phosphate ester surfactant, wherein the total amount of phosphate ester surfactant in the composition is 1.0-25% w/w;

(iii) at least one pharmaceutically acceptable solvent; and

(iv) water,

wherein the C max of the roflumilast from the topical composition is reduced relative to an oral roflumilast formulation marketed under the trademark DALIRESP®; and

wherein said phosphate ester surfactant comprises: potassium cetyl phosphate, potassium C9-15 alkyl phosphate, potassium C11-15 alkyl phosphate, potassium C12-13 alkyl phosphate, potassium C12-14 alkyl phosphate, potassium lauryl phosphate, C8-10 alkyl ethyl phosphate, C9-15 alkyl phosphate, C20-22 alkyl phosphate, castor oil phosphate, ceteth-10 phosphate, ceteth-20 phosphate, ceteth-8 phosphate, cetearyl phosphate, cetyl phosphate, dimethicone PEG-7 phosphate, disodium lauryl phosphate, disodium oleyl phosphate, lauryl phosphate, myristyl phosphate, octyldecyl phosphate, oleth-10 phosphate, oleth-5 phosphate, oleth-3 phosphate, oleyl ethyl phosphate, oleyl phosphate, PEG-26-PPG-30 phosphate, PPG-5 ceteareth-10 phosphate, PPG-5 ceteth-10 phosphate, sodium lauryl phosphate, sodium laureth-4 phosphate, steartyl phosphate, DEA-cetyl phosphate, DEA-oleth-10-phosphate, DEA-oleth-3 phosphate, DEA C8-18 perfluoroalkylethyl phosphate, dicetyl phosphate, dilaureth-10 phosphate, dimyristyl phosphate, dioleyl phosphate, tricetyl phosphate, triceteareth-4 phosphate, trilaureth-4 phosphate, trilauryl phosphate, triolyeyl phosphate, tristearyl phosphate, or a combination thereof.

23. The composition of claim 22 , wherein said pharmaceutically acceptable solvent comprises diethylene glycol monoethyl ether.

24. The composition of claim 23 , wherein said diethylene glycol monoethyl ether is in an amount of 10%-40% w/w.

25. The composition of claim 22 , wherein the plasma concentration curve of the roflumilast has no spike at C max .

26. The composition of claim 22 , wherein said roflumilast is in an amount of 0.05% w/w, 0.15% w/w, or 0.3% w/w, and wherein said composition is a foam or a cream.

27. A pharmaceutical composition for topical administration comprising:

(i) roflumilast, wherein the roflumilast is in an amount of 0.05-1% w/w;

(ii) at least one phosphate ester surfactant, wherein the total amount of phosphate ester surfactant in the composition is 1.0-25% w/w; and

(i at least one pharmaceutically acceptable solvent,

wherein the peak to trough ratio of roflumilast blood plasma concentration is less than 2 at steady state; and

wherein said phosphate ester surfactant comprises: potassium cetyl phosphate, potassium C9-15 alkyl phosphate, potassium C11-15 alkyl phosphate, potassium C12-13 alkyl phosphate, potassium C12-14 alkyl phosphate, potassium lauryl phosphate, C8-10 alkyl ethyl phosphate, C9-15 alkyl phosphate, C20-22 alkyl phosphate, castor oil phosphate, ceteth-10 phosphate, ceteth-20 phosphate, ceteth-8 phosphate, cetearyl phosphate, cetyl phosphate, dimethicone PEG-7 phosphate, disodium lauryl phosphate, disodium oleyl phosphate, lauryl phosphate, myristyl phosphate, octyldecyl phosphate, oleth-10 phosphate, oleth-5 phosphate, oleth-3 phosphate, oleyl ethyl phosphate, oleyl phosphate, PEG-26-PPG-30 phosphate, PPG-5 ceteareth-10 phosphate, PPG-5 ceteth-10 phosphate, sodium lauryl phosphate, sodium laureth-4 phosphate, steartyl phosphate, DEA-cetyl phosphate, DEA-oleth-10-phosphate, DEA-oleth-3 phosphate, DEA C8-18 perfluoroalkylethyl phosphate, dicetyl phosphate, dilaureth-10 phosphate, dimyristyl phosphate, dioleyl phosphate, tricetyl phosphate, triceteareth-4 phosphate, trilaureth-4 phosphate, trilauryl phosphate, triolyeyl phosphate, tristearyl phosphate, or a combination thereof.

28. The composition of claim 27 , wherein said pharmaceutically acceptable solvent comprises diethylene glycol monoethyl ether in an amount of 10%-40% w/w.

29. The composition of claim 28 , wherein said roflumilast is in an amount of 0.05% w/w, 0.15% w/w, or 0.3% w/w, and wherein said composition is a foam or a cream.

30. The composition of claim 27 , wherein the plasma concentration of the roflumilast plateaus after C max for 24 hours following administration.

Assignments (2)
SECURITY INTEREST Recorded Aug 9, 2024
From: ARCUTIS BIOTHERAPEUTICS, INC.
To: SLR INVESTMENT CORP.
Reel/Frame 068236/0418 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 19, 2024
From: OSBORNE, DAVID W.
To: ARCUTIS BIOTHERAPEUTICS, INC.
Reel/Frame 066490/0573 →
Continuity (4)
Continuation 17327236 · May 21, 2021
Continuation 16563435 · Sep 6, 2019
Provisional Application 62768314 · Nov 16, 2018
Related Publication 20240024300A1 · Jan 25, 2024
Cited By (1)
US 12,310,956