IP Library Granted Patent US 10,828,369
Granted Patent B2
US 10,828,369 · App. 16/128,835 · Granted Nov 10, 2020

Compositions and methods for treating diseases of the nail

Inventors: Gareth Winckle (Biot, FR); Gregory T. Fieldson (Morgantown, WV)
Assignee: DOW PHARMACEUTICAL SCIENCES, INC.
A61K47/24A01N43/653A61K9/0012A61K9/0014A61K9/06A61K9/08A61K9/10A61K31/4192A61K31/4196A61K31/454A61K47/10A61K47/14A61K47/18A61K47/22A61K47/34A61K47/44
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Quick Facts
Patent No.
US 10,828,369
App. No.
16/128,835
Granted
Nov 10, 2020
Kind
B2
Abstract

Methods and compositions for treating disorders of the nail and nail bed. Such compositions contain a vehicle in which all components of the composition are dissolved, suspended, dispersed, or emulsified, a non-volatile solvent, a wetting agent, and a pharmaceutically active ingredient that is soluble in the non-volatile solvent and/or a mixture of the vehicle and the non-volatile solvent, which composition has a surface tension of 40 dynes/cm or less and has continuing spreadability, and which composition is effective in treating a disorder of the nail or nail bed.

Claims (23)

1. A pharmaceutical composition for the topical treatment of a disorder of the nail or nail bed comprising:

(2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidine-1-yl)-1-(1H-1,2,4-triazole-1-yl)butane-2-ol in a concentration ranging from 0.0001% (w/w) to 30% (w/w),

ethanol in a concentration ranging from 10% (w/w) to 80% (w/w),

cyclomethicone in a concentration ranging from 1% (w/w) to 40% (w/w),

diisopropyl adipate plus C12-15 alkyl lactate in a combined concentration ranging from 10% (w/w) to 80% (w/w),

wherein the composition is formulated as a solution;

wherein the surface tension of the composition is 40 dynes/cm or less; and

wherein the composition does not comprise a polymeric film forming compound.

2. The pharmaceutical composition of claim 1 , wherein the surface tension of the composition is 30 dynes/cm or less.

3. The pharmaceutical composition of claim 1 , wherein the surface tension of the composition is 25 dynes/cm or less.

4. The pharmaceutical composition of claim 1 , wherein the concentration of (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidine-1-yl)-1-(1H-1,2,4-triazole-1-yl)butane-2-ol ranges from 2% (w/w) to 15% (w/w).

5. The pharmaceutical composition of claim 1 , wherein the concentration of (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidine-1-yl)-1-(1H-1,2,4-triazole-1-yl)butane-2-ol is 10% (w/w).

6. The pharmaceutical composition of claim 1 comprising diisopropyl adipate in a concentration ranging from 8% (w/w) to 15% (w/w), C12-15 alkyl lactate in a concentration ranging from 8% (w/w) to 15% (w/w), and ethanol in a concentration of at least 40% (w/w).

7. The pharmaceutical composition of claim 1 comprising cyclomethicone in a concentration ranging from 2% (w/w) to 15% (w/w).

8. The pharmaceutical composition of claim 7 comprising diisopropyl adipate in a concentration ranging from 8% (w/w) to 15% (w/w), C12-15 alkyl lactate in a concentration ranging from 8% (w/w) to 15% (w/w), and ethanol in a concentration of at least 40% (w/w).

9. The pharmaceutical composition of claim 8 , wherein the concentration of (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidine-1-yl)-1-(1H-1,2,4-triazole-1-yl)butane-2-ol is 10% (w/w).

10. The pharmaceutical composition of claim 1 , further comprising an antioxidant in a concentration ranging from 0.001% (w/w) to 0.5% (w/w).

11. The pharmaceutical composition of claim 10 comprising diisopropyl adipate in a concentration ranging from 8% (w/w) to 15% (w/w), C12-15 alkyl lactate in a concentration ranging from 8% (w/w) to 15% (w/w), and ethanol in a concentration of at least 40% (w/w).

12. The pharmaceutical composition of claim 11 , wherein the concentration of (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidine-1-yl)-1-(1H-1,2,4-triazole-1-yl)butane-2-ol is 10% (w/w).

13. The pharmaceutical composition of claim 1 comprising ethanol in a concentration of at least 15% (w/w).

14. The pharmaceutical composition of claim 1 comprising ethanol in a concentration of at least 25% (w/w).

15. The pharmaceutical composition of claim 14 comprising diisopropyl adipate in a concentration ranging from 8% (w/w) to 15% (w/w), C12-15 alkyl lactate in a concentration ranging from 8% (w/w) to 15% (w/w), and ethanol in a concentration of at least 40% (w/w).

16. The pharmaceutical composition of claim 15 , wherein the concentration of (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidine-1-yl)-1-(1H-1,2,4-triazole-1-yl)butane-2-ol is 10% (w/w).

Assignments (18)
U.S. PATENT SECURITY AGREEMENT Recorded Nov 25, 2025
From: BAUSCH HEALTH IRELAND LIMITED
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 073715/0375 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH HEALTH IRELAND LIMITED; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMA POLAND SPOLKA Z ORGANICZONA ODPOWIEDZIALNOSCIA; VALEANT SP. Z.O.O.
Reel/Frame 073637/0222 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; BAUSCH HEALTH IRELAND LIMITED; SOLTA MEDICAL IRELAND LIMITED
Reel/Frame 073654/0300 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH HEALTH AMERICAS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.
Reel/Frame 073637/0126 →
RELEASE OF SECURITY INTEREST Recorded Apr 8, 2025
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: SOLTA MEDICAL, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH IRELAND LIMITED (F/K/A/ VALEANT PHARMACEUTICALS IRELAND LIMITED); SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD; SANTARUS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; HUMAX PHARMACEUTICAL S.A.; SOLTA MEDICAL IRELAND LIMITED; BAUSCH & LOMB MEXICO, S.A. DE C.V.; BAUSCH+LOMB OPS B.V.; BAUSCH HEALTH AMERICAS, INC.; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH HOLDCO LIMITED; BAUSCH HEALTH MAGYARORSZAG KFT (A/K/A BAUSCH HEALTH HUNGARY LLC); BAUSCH HEALTH POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA (F/K/A VALEANT PHARMA POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA); BAUSCH HEALTH US, LLC; BAUSCH HEALTH, CANADA INC. / SANTE BAUSCH, CANADA INC.; ICN POLFA RZESZOW SPOLKA AKCYJNA (A/K/A ICN POLFA RZESZOW S.A.); ORAPHARMA, INC.; PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA SPOLKA AKCYJNA (A/K/A PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA S.A.); SOLTA MEDICAL DUTCH HOLDINGS B.V.; V-BAC HOLDING CORP.; VRX HOLDCO LLC; 1261229 B.C. LTD.; 1530065 B.C. LTD.
Reel/Frame 070778/0199 →
SECURITY AGREEMENT (FIRST LIEN) Recorded Nov 4, 2022
From: BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH IRELAND LIMITED; SOLTA MEDICAL IRELAND LIMITED
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 061882/0708 →
SECURITY AGREEMENT (SECOND LIEN) Recorded Nov 4, 2022
From: BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH IRELAND LIMITED; SOLTA MEDICAL IRELAND LIMITED
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 062078/0276 →
OMNIBUS PATENT SECURITY RELEASE AGREEMENT (REEL/FRAME 57287/0160) Recorded Nov 2, 2022
From: THE BANK OF NEW YORK MELLON
To: BAUSCH & LOMB INCORPORATED; BAUSCH + LOMB IRELAND LIMITED
Reel/Frame 061874/0539 →
SECURITY AGREEMENT (SECOND LIEN) Recorded Oct 5, 2022
From: BAUSCH HEALTH US, LLC; BAUSCH HEALTH AMERICAS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; SOLTA MEDICAL, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 061606/0468 →
SECURITY AGREEMENT (FIRST LIEN) Recorded Oct 4, 2022
From: BAUSCH HEALTH US, LLC; BAUSCH HEALTH AMERICAS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; SOLTA MEDICAL, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 061595/0066 →
SECURITY INTEREST Recorded Jun 13, 2022
From: BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; BAUSCH HEALTH IRELAND LIMITED; SOLTA MEDICAL IRELAND LIMITED
To: THE BANK OF NEW YORK MELLON
Reel/Frame 060346/0705 →
SECURITY INTEREST Recorded Oct 5, 2021
From: BAUSCH & LOMB IRELAND LIMITED; BAUSCH HEALTH COMPANIES INC.; DR. GERHARD MANN CHEM.-PHARM. FABRIK GMBH; TECHNOLAS PERFECT VISION GMBH
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 057821/0800 →
SECURITY INTEREST Recorded Aug 25, 2021
From: BAUSCH HEALTH IRELAND LIMITED; BAUSCH+LOMB IRELAND LIMITED; SALIX PHARMACEUTICALS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 057287/0160 →
SECURITY INTEREST Recorded Aug 25, 2021
From: BAUSCH HEALTH IRELAND LIMITED; BAUSCH+LOMB IRELAND LIMITED; SALIX PHARMACEUTICALS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 057287/0140 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 2, 2020
From: DOW PHARMACEUTICAL SCIENCES, INC.
To: BAUSCH HEALTH IRELAND LIMITED
Reel/Frame 054571/0413 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 19, 2019
From: WINCKLE, GARETH; FIELDSON, GREGORY T.
To: DOW PHARMACEUTICAL SCIENCES, INC.
Reel/Frame 050436/0947 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jul 3, 2019
From: BAUSCH HEALTH IRELAND LIMITED; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT PHARMACEUTICALS LUXEMBOURG S.À R.L.; VALEANT PHARMA POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA; VALEANT SP. Z O. O.
To: THE BANK OF NEW YORK MELLON, AS COLLATERAL AGENT
Reel/Frame 049672/0652 →
SECURITY INTEREST Recorded Mar 11, 2019
From: BAUSCH HEALTH AMERICAS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 048556/0758 →