IP Library › Granted Patent US 8,809,307
Granted Patent B2
US 8,809,307 · App. 13/287,176 · Granted Aug 19, 2014

Pharmaceutical formulations containing corticosteroids for topical administration

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,809,307
App. No.
13/287,176
Granted
Aug 19, 2014
Kind
B2
Abstract

The potency of a topical corticosteroid in a pharmaceutical formulation is maintained even when the concentration of the corticosteroid is substantially reduced by providing the corticosteroid in a formulation containing a liquid oil component that includes a dicarboxylic acid ester and/or a monocarboxylic acid ester.

Claims (28)

1. A pharmaceutical composition for topical application to the skin of an individual comprising halobetasol propionate at a concentration of 0.04% or less and a liquid oil component comprising one or more dicarboxylic acid esters, wherein the dicarboxylic acid esters are selected from diethyl sebacate, diisopropyl adipate, and dibutyl sebacate and wherein at least 25% of the halobetasol propionate is solubilized in the liquid oil component at 22° C.

2. The pharmaceutical composition of claim 1 wherein the concentration of the halobetasol propionate is 0.025% or less.

3. The pharmaceutical composition of claim 2 wherein the concentration of the halobetasol propionate is 0.01% or less.

4. The pharmaceutical composition of claim 1 wherein the concentration of the liquid oil component is sufficient to dissolve the amount of halobetasol propionate in the composition at a temperature of 22° C.±2° C.

5. The pharmaceutical composition of claim 4 wherein the concentration of the liquid oil component is between 1.5 and 3 tunes that required to completely solubilize the amount of halobetasol propionate in the composition at a temperature of 22° C.±2° C.

6. The pharmaceutical composition of claim 5 wherein the concentration of the liquid oil component is between 1.75 and 2.75 times that required to completely solubilize the amount of halobetasol propionate in the composition at a temperature of 22° C.±2° C.

7. The pharmaceutical composition of claim 1 wherein the concentration of the esters in the liquid oil component is at least 30% of the concentration of the liquid oil component in the composition.

8. The pharmaceutical composition of claim 7 wherein the concentration of the esters in the liquid oil component is at least 50% of the concentration of the liquid oil component in the composition.

9. The pharmaceutical composition of claim 8 wherein the concentration of the esters in the liquid oil component is at least 70% of the concentration of the liquid oil component in the composition.

10. The pharmaceutical composition of claim 9 wherein the concentration of the esters in the liquid oil component is at least 90% of the concentration of the liquid oil component in the composition.

11. The pharmaceutical composition of claim 10 wherein the concentration of the esters in the liquid oil component is 100% of the concentration of the liquid oil component in the composition.

12. The pharmaceutical composition of claim 1 wherein the dicarboxylic acid ester is diethyl sebacate.

13. The pharmaceutical formulation of claim 1 wherein the halobetasol propionate is at a concentration of 0.025% or less, the liquid oil component comprises diethyl sebacate, and wherein at least 50% of the halobetasol propionate is solubilized in the liquid oil component at room temperature.

14. The pharmaceutical formulation of claim 13 wherein the concentration of the liquid oil component is between 1.5 and 3 times that required to completely solubilize the amount of halobetasol propionate in the composition at a temperature of 22° C.±2° C.

15. A method for treating a disorder of the skin that is amenable to treatment with a topical corticosteroid comprising providing a pharmaceutical composition of claim 1 and applying an amount to the skin that is effective in ameliorating the signs or symptoms of the disorder.

16. A method for treating a disorder of the skin that is amenable to treatment with a topical corticosteroid comprising providing a pharmaceutical composition of claim 4 and applying an amount to the skin that is effective in ameliorating the signs or symptoms of the disorder.

17. A method for treating a disorder of the skin that is amenable to treatment with a topical corticosteroid comprising providing a pharmaceutical composition of claim 13 and applying an amount to the skin that is effective in ameliorating the signs or symptoms of the disorder.

18. The pharmaceutical composition of claim wherein the concentration of the halobetasol propionate is 0.035%.

19. The pharmaceutical composition of claim 1 , wherein the liquid, oil component further comprises light mineral oil.

20. The pharmaceutical composition of claim 19 , wherein the liquid oil component comprises diethyl sebacate and light mineral oil.

21. The pharmaceutical composition of claim 1 , wherein the liquid oil component comprises diethyl sebacate and isopropyl myristate.

22. A pharmaceutical composition for topical application to the skin of an individual comprising halobetasol propionate at a concentration of 0.04% or less and a liquid oil component comprising one or more dicarboxylic acid esters, wherein the dicarboxylic acid esters are selected from diethyl sebacate, diisopropyl adipate, and dibutyl sebacate and wherein the concentration of the liquid oil component is between 1.5 and 3 times that required to completely solubilize the amount of halobetasol propionate in the composition at a temperature of 22° C.±2° C.

23. The pharmaceutical composition of claim 22 , wherein the concentration of the esters in the liquid oil component is at least 30% of the concentration of the liquid oil component in the composition.

24. The pharmaceutical composition of claim 22 , wherein the concentration of the esters in the liquid oil component is at least 50% of the concentration of the liquid oil component in the composition.

25. The pharmaceutical composition of claim 22 , wherein the concentration of the esters in the liquid oil component is at least 70% of the concentration of the liquid oil component in the composition.

26. The pharmaceutical composition of claim 22 , wherein the concentration of the esters in the liquid oil component is at least 90% of the concentration of the liquid oil component in the composition.

27. The pharmaceutical composition of claim 22 , wherein the concentration of the esters in the liquid oil component is 100% of the concentration of the liquid oil component in the composition.

28. The pharmaceutical composition of claim 22 , wherein the liquid oil component further comprises light mineral oil.

Assignments (20)
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: ATON PHARMA, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH & LOMB PHARMA HOLDINGS CORP.; COMMONWEALTH LABORATORIES, LLC; DOW PHARMACEUTICAL SCIENCES, INC.; ECR PHARMACEUTICALS CO., INC.; LABORATOIRE CHAUVIN S.A.S.; MEDICIS PHARMACEUTICAL CORPORATION; ONPHARMA INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, LTD.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; SOLTA MEDICAL, INC.; SYNERGETICS USA, INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT CANADA LP; VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS INTERNATIONAL, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA LLC; WIRRA IP PTY LIMITED; VALEANT PHARMA POLAND SP. Z O.O.; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMACEUTICALS IRELAND LIMITED
Reel/Frame 073637/0001 →
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 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 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 (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 →
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 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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 26, 2019
From: DOW PHARMACEUTICALS SCIENCES, INC.
To: BAUSCH HEALTH IRELAND LIMITED
Reel/Frame 049590/0779 →
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 →
SECURITY INTEREST Recorded Feb 26, 2018
From: ATON PHARMA, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH & LOMB PHARMA HOLDINGS CORP.; COMMONWEALTH LABORATORIES, LLC; DOW PHARMACEUTICAL SCIENCES, INC.; ECR PHARMACEUTICALS CO., INC.; LABORATOIRE CHAUVIN S.A.S.; MEDICIS PHARMACEUTICAL CORPORATION; ONPHARMA INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, LTD.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; SOLTA MEDICAL, INC.; SYNERGETICS USA, INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT CANADA LP; VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS INTERNATIONAL, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA LLC; WIRRA IP PTY LIMITED; VALEANT PHARMA POLAND SP. Z O.O.; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMACEUTICALS IRELAND LIMITED
To: THE BANK OF NEW YORK MELLON, AS COLLATERAL AGENT
Reel/Frame 045444/0634 →
SECURITY INTEREST Recorded Feb 26, 2018
From: ATON PHARMA, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH & LOMB PHARMA HOLDINGS CORP.; COMMONWEALTH LABORATORIES, LLC; DOW PHARMACEUTICAL SCIENCES, INC.; ECR PHARMACEUTICALS CO., INC.; LABORATOIRE CHAUVIN S.A.S.; MEDICIS PHARMACEUTICAL CORPORATION; ONPHARMA INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, LTD.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; SOLTA MEDICAL, INC.; SYNERGETICS USA, INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT CANADA LP; VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS INTERNATIONAL, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA LLC; WIRRA IP PTY LIMITED; VALEANT PHARMA POLAND SP. Z O.O.; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMACEUTICALS IRELAND LIMITED
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 045444/0299 →
SECURITY INTEREST Recorded Jul 19, 2017
From: DOW PHARMACEUTICAL SCIENCES, INC.
To: THE BANK OF NEW YORK MELLON
Reel/Frame 043046/0124 →
SECURITY INTEREST Recorded Jul 18, 2016
From: ATON PHARMA, INC.; BAUSCH & LOMB INCORPORATED; BAUSH & LOMB PHARMA HOLDINGS CORP.; DENDREON PHARMACEUTICALS, INC.; DOW PHARMACEUTICAL SCIENCES, INC.; MEDICIS PHARMACEUTICAL CORPORATION; OBAGI MEDICAL PRODUCTS, INC.; OMP, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD; SANTARUS, INC.; SOLTA MEDICAL, INC.; VALEANT CANADA LP, BY ITS GENERAL PARTNER VALEANT CANADA GP LIMITED; VALEANT PHARMACEUTICALS INTERNATIONAL, INC.; VALEANT HOLDINGS IRELAND (AS SUCCESSOR TO VALEANT INTERNATIONAL BERMUDA); VALEANT PHARMACEUTICALS NORTH AMERICA LLC; VALEANT PHARMACEUTICALS IRELAND
To: BARCLAYS BANK PLC
Reel/Frame 039380/0385 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 21, 2011
From: ANGEL, ARTURO; DOW, GORDON
To: DOW PHARMACEUTICAL SCIENCES, INC.
Reel/Frame 027303/0889 →