IP Library › Granted Patent US 7,981,877
Granted Patent B2
US 7,981,877 · App. 11/432,742 · Granted Jul 19, 2011

Stabilized steroid composition and method for its preparation

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Quick Facts
Patent No.
US 7,981,877
App. No.
11/432,742
Granted
Jul 19, 2011
Kind
B2
Abstract

Stabilized, 17-substituted hydrocortisone containing compositions and methods of manufacture are disclosed. Isomerization of the hydrocortisone component of topical steroid compositions is markedly reduced by including an omega-6 acid component in the form of a free acid or as a compound such as an ester. Specifically disclosed are methods for preventing the isomerization of hydrocortisone 17-butyrate into hydrocortisone 21-butyrate through the use of safflower oil.

Claims (20)

1. A method for inhibiting the isomerization of hydrocortisone 17-butyrate to hydrocortisone 21-butyrate, said method comprising the step of:

disposing said hydrocortisone 17-butyrate in a composition which includes a stabilizer comprising an omega-6 acid or an ester of an omega-6 acid.

2. The method of claim 1 , wherein the stabilizer comprises linoleic acid.

3. The method of claim 1 , wherein the stabilizer comprises a triglyceride which includes an ester of said omega-6 acid.

4. The method of claim 3 , wherein said triglyceride comprises safflower oil.

5. The method of claim 1 , wherein the step of adding said stabilizer further comprises adding said stabilizer in an amount so that the omega-6 acid component is at least equimolar to a quantity of said hydrocortisone 17-butyrate.

6. The method of claim 5 , wherein the molar amount of the omega-6 acid component is substantially greater than the molar amount of hydrocortisone 17-butyrate.

7. A method for stabilizing a hydrocortisone compound comprising hydrocortisone 17-butyrate, said method comprising the step of:

disposing said hydrocortisone compound in a composition which includes a stabilizer comprising an omega-6 acid or an ester of an omega-6 acid;

wherein the step of adding said stabilizer comprises adding said stabilizer in an amount so that the omega-6 acid component thereof is at least equimolar to a quantity of said hydrocortisone 17-butyrate.

8. The method of claim 7 wherein the stabilizer comprises safflower oil.

9. A stabilized hydrocortisone composition comprising:

17-hydrocortisone butyrate; and

a stabilizer comprising an omega-6 acid or an ester of an omega-6 acid.

10. The composition of claim 9 , wherein said stabilizer is present in an amount so that the omega-6 acid component thereof is at least equimolar with the hydrocortisone 17-butyrate.

11. A stabilized composition comprising:

hydrocortisone 17-butyrate; and

a stabilizer comprising an omega-6 acid or an ester of said omega-6 acid; wherein said stabilizer is present in an amount such that the molar concentration of the omega-6 acid component thereof is greater than the molar concentration of said hydrocortisone butyrate.

12. The composition of claim 11 , wherein said stabilizer comprises safflower oil.

13. The composition of claim 12 , wherein the weight percentage of said safflower oil is at least ten times greater than the weight percentage of said hydrocortisone butyrate.

Assignments (30)
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 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 & 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.; BAUSCH HEALTH AMERICAS, INC.
Reel/Frame 073654/0242 →
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 (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 AGREEMENT Recorded Feb 10, 2022
From: 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.; BAUSCH HEALTH AMERICAS, INC.
To: THE BANK OF NEW YORK MELLON
Reel/Frame 059121/0001 →
SECURITY INTEREST Recorded Jun 8, 2021
From: 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.; BAUSCH HEALTH AMERICAS, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 056811/0814 →
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 →
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: PRECISION DERMATOLOGY, INC.
To: THE BANK OF NEW YORK MELLON
Reel/Frame 043041/0864 →
SECURITY AGREEMENT Recorded Jul 6, 2015
From: ECR PHARMACEUTICALS CO., INC.; PRECISION DERMATOLOGY, INC.
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 036091/0257 →
RELEASE OF SECURITY INTEREST Recorded Jul 7, 2014
From: GCI CAPITAL MARKETS, LLC
To: PRECISION DERMATOLOGY, INC.
Reel/Frame 033280/0556 →
CORRECTIVE ASSIGNMENT TO CORRECT THE RELEASE OF SECURED PARTY PREVIOUSLY RECORDED ON REEL 013384 FRAME 0126. ASSIGNOR(S) HEREBY CONFIRMS THE CORRECTION OF DOC DATE FROM 4-25-2012 TO 9-9-2013. Recorded Oct 29, 2013
From: FERNDALE LABORATORIES, INC.
To: PRECISION DERMATOLOGY, INC.
Reel/Frame 031509/0788 →
RELEASE OF SECURITY INTEREST Recorded Sep 27, 2013
From: MIDCAP FUNDING III, LLC
To: PRECISION DERMATOLOGY COMPANY, INC.; ONSET DERMATOLOGICS, LLC; PROSKIN, LLC; PRECISION MD, LLC; TP CREAM SUB, LLC; TP LOTION SUB, LLC
Reel/Frame 031296/0492 →
SECURITY AGREEMENT Recorded Sep 20, 2013
From: PRECISION DERMATOLOGY, INC.
To: GCI CAPITAL MARKETS LLC
Reel/Frame 031249/0011 →
RELEASE OF SECURITY INTEREST Recorded Sep 11, 2013
From: FERNDALE LABORATORIES, INC.
To: PRECISION DERMATOLOGY, INC.
Reel/Frame 031184/0126 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2012
From: TRIAX PHARMACEUTICALS, LLC
To: PRECISION DERMATOLOGY, INC.
Reel/Frame 028828/0598 →
SECURITY AGREEMENT Recorded May 18, 2012
From: PRECISION DERMATOLOGY, INC.; ONSET DERMATOLOGICS, LLC; PROSKIN LLC; PRECISION MD LLC; TP CREAM SUB, LLC; TP LOTION SUB, LLC
To: MIDCAP FUNDING III, LLC
Reel/Frame 028234/0424 →
RELEASE OF SECURITY INTEREST Recorded Apr 26, 2012
From: LAMINAR DIRECT CAPITAL, L.L.C. AS SUCCESSOR IN INTEREST TO LAMINAR DIRECT CAPITAL, L.P.
To: TRIAX PHARMACEUTICALS, LLC
Reel/Frame 028114/0337 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2008
From: PATEL, PRAVIN M.
To: FERNDALE IP, INC.
Reel/Frame 020830/0840 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 5, 2007
From: FERNDALE IP, INC.
To: TRIAX PHARMACEUTICALS, LLC
Reel/Frame 020199/0294 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 3, 2007
From: FERNDALE LABORATORIES, INC.
To: TRIAX PHARMACEUTICALS, LLC
Reel/Frame 020240/0441 →
NOTICE OF GRANT OF SECURITY INTEREST Recorded Sep 25, 2007
From: TRIAX PHARMACEUTICALS, LLC
To: LAMINAR DIRECT CAPITAL L.P., AS COLLATERAL AGENT
Reel/Frame 019870/0970 →
REASSIGNMENT & RELEASE OF SECURITY INTEREST Recorded Sep 21, 2007
From: NATIONAL CITY BANK OF THE MIDWEST
To: FERNDALE IP, INC.
Reel/Frame 019881/0068 →
SECURITY AGREEMENT Recorded Sep 10, 2007
From: TRIAX PHARMACEUTICALS, LLC
To: FERNDALE LABORATORIES, INC.
Reel/Frame 019824/0647 →
SECURITY AGREEMENT Recorded Jul 26, 2006
From: FERNDALE IP, INC.
To: NATIONAL CITY BANK OF THE MIDWEST
Reel/Frame 017996/0505 →