IP Library Granted Patent US 11,813,284
Granted Patent B2
US 11,813,284 · App. 14/910,207 · Granted Nov 14, 2023

Topical compositions and methods of using the same

Inventors: Ryan Doxey (Raleigh, NC); Jian Bao (Cary, NC)
Assignee: Novan, Inc.
A61K33/00A61K8/042A61K8/25A61K8/345A61K8/898A61K9/0014A61K9/06A61K9/10A61K9/107A61K47/02A61K47/10A61K47/12A61K47/14A61K47/32A61K47/38A61K47/44A61K47/52A61K47/59A61Q17/005A61Q19/00A61K2800/22
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Quick Facts
Patent No.
US 11,813,284
App. No.
14/910,207
Granted
Nov 14, 2023
Kind
B2
Abstract

The present invention generally relates to topical compositions and methods of using the same. A preferred topical pharmaceutical composition comprises a nitric oxide-releasing active pharmaceutical ingredient in admixture with a hydrophilic composition and a hydrophobic composition wherein the nitric oxide-releasing active pharmaceutical ingredient comprises a nitric oxide-releasing compound having a diazeniumdiolate functional group.

Claims (43)

1. A topical pharmaceutical composition comprising a hydrophobic composition in admixture with a hydrophilic composition,

wherein the hydrophobic composition comprises a nitric oxide-releasing co-condensed silica particle having a diazeniumdiolate functional group, a hydrophobic base, and an amphiphilic compound;

wherein the hydrophilic composition is an aqueous hydrogel having a pH in a range of about 4 to about 5 and the hydrogel comprises a buffer; and

wherein a ratio of the hydrophilic composition to the hydrophobic composition in the topical pharmaceutical composition is 4:1 or less.

2. The topical pharmaceutical composition of claim 1 , wherein the hydrophilic composition comprises a phosphate buffer.

3. The topical pharmaceutical composition of claim 1 , wherein the hydrophilic composition further comprises cellulose or a pharmaceutically acceptable salt thereof, chitosan, an acrylic acid polymer, or any combination thereof.

4. The topical pharmaceutical composition of claim 1 , wherein the hydrophilic composition further comprises a polyhydric alcohol.

5. The topical pharmaceutical composition of claim 1 , wherein the topical pharmaceutical composition is self-emulsifying.

6. The topical pharmaceutical composition of claim 1 , wherein the hydrophilic composition has a viscosity of about 5000 cP to about 100,000 cP.

7. The topical pharmaceutical composition of claim 1 , wherein the hydrophobic composition comprises:

nitric oxide-releasing co-condensed silica particles at a concentration from 0.1% to 30% by weight of the hydrophobic composition;

the hydrophobic base at a concentration from 65% to 95% by weight of the hydrophobic composition; and

the amphiphilic compound at a concentration from 2% to 10% by weight of the hydrophobic composition.

8. The topical pharmaceutical composition of claim 1 , wherein the topical pharmaceutical composition has a pH of about 3 to about 9.

9. The topical composition of claim 1 , wherein the hydrophobic base comprises mineral oil.

10. A kit comprising:

a hydrophilic composition, wherein the hydrophilic composition is an aqueous hydrogel having a pH in a range of about 4 to about 5 and the hydrogel comprises a buffer; and

a hydrophobic composition comprising an active pharmaceutical ingredient, a hydrophobic base; and an amphiphilic compound, wherein the active pharmaceutical ingredient comprises a nitric oxide-releasing co-condensed silica particle having a diazeniumdiolate functional group,

wherein a ratio of the hydrophilic composition to the hydrophobic composition in the kit is 4:1 or less.

11. The kit of claim 10 , wherein the hydrophilic composition further comprises:

a cellulose or a pharmaceutically acceptable salt thereof;

a polyhydric alcohol; and

water.

12. The kit of claim 10 , wherein the hydrophobic base comprises mineral oil.

13. The kit of claim 10 , wherein the hydrophilic composition and the hydrophobic composition are separately stored.

14. A method of stably storing a diazeniumdiolate modified macromolecule in a hydrophobic composition and releasing nitric oxide from the diazeniumdiolate modified macromolecule, the method comprising:

admixing the hydrophobic composition with a hydrophilic composition to form an admixture,

wherein the hydrophobic composition comprises a nitric oxide-releasing co-condensed silica particle having a diazeniumdiolate functional group, a hydrophobic base, and an amphiphilic compound,

wherein the hydrophilic composition is an aqueous hydrogel having a pH in a range of about 4 to about 5 and the hydrogel comprises a buffer, and

wherein a ratio of the hydrophilic composition to the hydrophobic composition in the admixture is 4:1 or less.

15. The topical pharmaceutical composition of claim 1 , wherein the buffer comprises acetic acid and an acetate.

16. The topical pharmaceutical composition of claim 1 , wherein the admixture has a pH in a range of about 4 to about 6.5.

17. The topical pharmaceutical composition of claim 1 , wherein the admixture has a pH in a range of about 4.5 to about 5.5.

18. The topical pharmaceutical composition of claim 1 , wherein the hydrogel maintains the pH of the admixture in a range of about 4 to about 6.5 for about 24 hours after combination.

19. The topical pharmaceutical composition of claim 1 , wherein the topical pharmaceutical composition has a single phase.

20. The topical pharmaceutical composition of claim 1 , wherein the amphiphilic compound comprises polyethylene glycol (PEG) caprylic/capric glyceride.

21. The topical pharmaceutical composition of claim 1 , wherein the nitric oxide-releasing compound in the hydrophobic composition is dispersed in an oil phase.

22. The topical pharmaceutical composition of claim 1 , wherein the hydrophilic composition comprises a phosphate buffer, and wherein the topical pharmaceutical composition is continuous.

23. The kit of claim 10 , wherein the hydrophobic composition comprises:

nitric oxide-releasing co-condensed silica particles at a concentration from 0.1% to 30% by weight of the hydrophobic composition;

the hydrophobic base at a concentration from 65% to 95% by weight of the hydrophobic composition; and

the amphiphilic compound at a concentration from 2% to 10% by weight of the hydrophobic composition.

24. The kit of claim 23 , wherein the hydrophobic base comprises mineral oil.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 30, 2025
From: LNHC, INC.
To: LIGAND PHARMACEUTICALS INCORPORATED
Reel/Frame 071481/0040 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 18, 2024
From: NOVAN, INC.
To: LNHC, INC.
Reel/Frame 066350/0942 →
SECURITY INTEREST Recorded Oct 18, 2023
From: CYDEX PHARMACEUTICALS, INC.; LIGAND PHARMACEUTICALS INCORPORATED; METABASIS THERAPEUTICS, INC.; PFENEX INC.
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 065271/0025 →