IP Library Granted Patent US 10,925,689
Granted Patent B2
US 10,925,689 · App. 15/324,526 · Granted Feb 23, 2021

Nitric oxide releasing nail coating compositions, nitric oxide releasing nail coatings, and methods of using the same

Inventors: Ryan Doxey (Raleigh, NC); Yong Zhang (Cary, NC)
Assignee: Novan, Inc.
A61C3/02A61K8/19A61K8/25A61K8/731A61K8/8182A61K9/0014A61K9/06A61K9/7015A61K31/695A61K33/00A61K47/10A61K47/32A61K47/38A61P31/10A61K2800/22A61K2800/88A61K2800/884
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Quick Facts
Patent No.
US 10,925,689
App. No.
15/324,526
Granted
Feb 23, 2021
Kind
B2
Abstract

The present invention relates to nitric oxide (NO)-releasing nail coating compositions, NO-releasing coatings, and methods of using the same, for example, to treat fungal infections of a nail. It is noted that aspects described with respect to one embodiment may be incorporated in different embodiments although not specifically described relative thereto. Provided according to embodiments of the invention are nitric oxide (NO)-releasing nail coating compositions and/or coatings.

Claims (34)

1. A nitric oxide (NO)-releasing nail coating composition comprising NO-releasing co-condensed silica at a concentration in a range of about 0.1% to about 70% by weight percent of the composition;

at least one hydrophilic polymer at a concentration in a range of about 1% to about 15% by weight percent of the composition;

at least one film-forming polymer at a concentration in a range of about 1% to about 25% by weight percent of the composition, the at least one film-forming polymer selected from the group consisting of nitrocellulose, methyl vinyl ether/maleic acid copolymer, vinyl pyrrolidone/vinyl acetate copolymer, poly N-vinylacetamide/sodium acrylate copolymer, ethyl cellulose, methacrylate polymer, methacrylate copolymer, and cellulose acetate; and

an organic solvent at a concentration in a range of about 30% to about 98% by weight percent of the composition,

wherein the composition forms a lacquer when dried or cured, wherein the lacquer allows moisture penetration sufficient to release at least a portion of the NO from the NO-releasing co-condensed silica, and

wherein the NO-releasing co-condensed silica is in the form of particles that are suspended in the composition.

2. The NO-releasing nail coating composition of claim 1 , wherein the NO-releasing co-condensed silica comprises diazeniumdiolate functional groups.

3. The NO-releasing nail coating composition of claim 1 , wherein the at least one film-forming polymer comprises at least one of nitrocellulose, ethyl cellulose and cellulose acetate.

4. The NO-releasing nail coating composition of claim 1 , wherein the at least one organic solvent comprises at least one solvent selected from the group consisting of acetone, ethyl acetate, ethyl alcohol, denatured alcohol, isopropyl alcohol, and any combination thereof.

5. The NO-releasing nail coating composition of claim 1 , wherein the at least one hydrophilic polymer comprises polyvinylpyrolidone polymer (PVP) and/or copolymers thereof.

6. The NO-releasing nail coating composition of claim 1 , further comprising one or more additive(s), optionally wherein each of the one or more additive(s) is present in an amount of about 0.01% to about 20% by weight of the composition.

7. The NO-releasing nail coating composition of claim 1 , wherein the at least one hydrophilic polymer is present in the composition at a concentration in a range from about 1% to about 10% by weight percent of the composition; the at least one film-forming polymer is present in the composition at a concentration in a range from about 1% to about 10% by weight percent of the composition; and the organic solvent is present in the composition at a concentration in a range from about 75% to about 98% by weight percent of the composition.

8. The NO-releasing nail coating composition of claim 1 , wherein the NO storage of the composition is in a range from about 1 nmol NO/mg to about 2.5 μmol NO/mg.

9. The NO-releasing nail coating composition of claim 1 , wherein the NO-releasing nail coating composition has a shelf life in a range from about 12 to about 104 weeks.

10. The NO-releasing nail coating composition of claim 1 , wherein the NO-releasing nail coating composition has a useful life in a range from about 60 to about 730 days.

11. The NO-releasing nail coating composition of claim 1 , wherein the NO-releasing co-condensed silica is diazeniumdiolate-functionalized co-condensed silica and the diazeniumdiolate-functionalized co-condensed silica is present in the composition at a concentration in a range of about 0.1% to about 25% by weight of the composition;

wherein the at least one hydrophilic polymer is PVP and/or a copolymer thereof and the PVP and/or copolymer thereof is present in the composition at a concentration in a range of about 1% to about 10% by weight of the composition;

wherein the at least one film-forming polymer is ethyl cellulose and the ethyl cellulose is present in the composition at a concentration in a range of about 1% to about 10% by weight of the composition; and

the organic solvent is present in the composition at a concentration in a range of about 75% to about 97.9% by weight of the composition.

12. The NO-releasing nail coating composition of claim 1 , wherein, after application to a nail of a subject, NO is released in an amount of about 0.05% to about 20% by weight of the composition.

13. A two component NO-releasing nail coating system comprising:

a first composition comprising the NO-releasing nail coating composition of claim 1 ; and

a second composition comprising a proton source.

14. The two component NO-releasing nail coating system of claim 13 , wherein the NO-releasing co-condensed silica is present in the composition at a concentration in a range of about 0.1% to about 50% by weight percent of the composition.

15. The two component NO-releasing nail coating system of claim 13 , wherein the second composition is in the form of a hydrogel, optionally wherein the second composition is provided in and/or on a substrate.

16. A kit comprising:

a first composition comprising the NO-releasing nail coating composition of claim 1 ; and

a second composition comprising a proton source.

17. The kit of claim 16 , wherein the first composition and the second composition are separately stored.

18. The NO-releasing nail coating composition of claim 1 , wherein the at least one hydrophilic polymer is selected from the group consisting of hydroxypropyl methyl cellulose, hydroxypropyl cellulose, methylcellulose, polyvinylpyrrolidone polymers, polyvinylpyrrolidone copolymers, sodium carboxy methylcellulose, and polyvinyl alcohol.

19. A method of treating a fungal infection of a nail of a subject comprising:

contacting the nail with the NO-releasing nail coating composition of claim 1 for a time sufficient to treat the fungal infection.

20. A method of improving the appearance of a nail of a subject comprising:

topically applying the NO-releasing nail coating composition of claim 1 to said nail of said subject, thereby improving the appearance of said nail.

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 →