IP Library Granted Patent US 8,119,112
Granted Patent B2
US 8,119,112 · App. 12/203,384 · Granted Feb 21, 2012

Ophthalmic compositions with an amphoteric surfactant and hyaluronic acid

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Quick Facts
Patent No.
US 8,119,112
App. No.
12/203,384
Granted
Feb 21, 2012
Kind
B2
Abstract

Ophthalmic compositions that comprise 0.1 ppm to 10 ppm of a cationic antimicrobial component selected from the group consisting of biguanides, polymeric biguanides, quaternium ammonium compounds and any one mixture thereof; 0.005 wt. % to 0.15 wt. % of hyaluronic acid; and 0.01 wt. % to 1.0 wt. % of an amphoteric surfactant of general formula I wherein R 1 is R or —(CH 2 ) n —NHC(O)R, wherein R is a C 8 -C 16 alkyl optionally substituted with hydroxyl and n is 2, 3 or 4; R 2 and R 3 are each independently selected from methyl, ethyl, propyl or iso-propyl; and R 4 is a C 2 -C 8 alkylene optionally substituted with hydroxyl. The invention is also direct to the use of the ophthalmic compositions to clean and disinfect contact lenses, and in particular, soft, silicone hydrogel contact lenses.

Claims (25)

1. An aqueous contact lens cleaning and disinfecting solution composition comprising:

0.8 ppm to 1.6 ppm of poly(hexamethylene biguanide);

0.5 ppm to 2 ppm α-[4-tris(2-hydroxyethyl)-ammonium chloride-2-butenyl]poly[1-dimethyl ammonium chloride-2-butenyl]-ω-tris(2-hydroxyethyl)ammonium chloride;

0.005 wt. % to 0.015 wt. % hyaluronic acid;

0.01 wt. % to 0.6 wt. % of a sulfobetaine of general formula I

wherein R 1 is a C 8 -C 16 alkyl optionally substituted with at least one hydroxyl; R 2 and R 3 are each methyl; and R 4 is a C 2 -C 4 alkylene optionally substituted with one hydroxyl;

a boric acid/borate buffer;

a nonionic surfactant selected from poloxamer, poloxamine or any combination thereof; and

sodium chloride, potassium chloride or any combination thereof.

2. The ophthalmic composition of claim 1 wherein the nonionic surfactant is poloxamine with an HLB value from 13 to 28.

3. The ophthalmic composition of claim 1 wherein R 1 is a straight, saturated C 10 alkyl.

4. A method of cleaning and disinfecting a contact lens, the method comprising soaking the contact lens in the ophthalmic composition of claim 1 for at least two hours.

5. The method of claim 4 further comprising inserting the cleaned and disinfected contact lens into the eye without rinsing the lens after soaking.

6. The composition of claim 1 further comprising dexpanthenol, sorbitol, glycolic acid, 2-amino-2-methyl-1,3-propanediol or any mixture thereof.

7. The composition of claim 1 further comprising citrate, citric acid or a mixture thereof.

8. The composition of claim 1 further comprising propylene glycol, hydroxypropyl guar or myristamidopropyl dimethylamine.

9. The composition of claim 1 further comprising hydroxypropylmethyl cellulose.

10. An aqueous contact lens care solution composition comprising:

1 ppm to 1.3 ppm of poly(hexamethylene biguanide);

1 ppm α-[4-tris(2-hydroxyethyl)-ammonium chloride-2-butenyl]poly[1-dimethyl ammonium chloride-2-butenyl]-ω-tris(2-hydroxyethyl)ammonium chloride;

0.008 wt. % to 0.015 wt. % hyaluronic acid; and

a borate buffer system component selected from the group consisting of boric acid and borate.

11. The solution of claim 10 further comprising a nonionic surfactant selected from poloxamer, poloxamine or any combination thereof; and

sodium chloride, potassium chloride or any combination thereof.

12. A method of cleaning and disinfecting a contact lens, the method comprising soaking the contact lens in the ophthalmic composition of claim 10 for at least two hours.

Assignments (22)
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 & 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 →
ASSIGNMENT OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (059913/0548) Recorded Aug 14, 2025
From: CITIBANK, N.A., AS RESIGNING AGENT
To: JPMORGAN CHASE BANK, N.A., AS SUCCESSOR AGENT
Reel/Frame 072469/0091 →
PATENT SECURITY AGREEMENT Recorded Jul 1, 2025
From: BAUSCH & LOMB INCORPORATED; ALDEN OPTICAL LABORATORIES, INC.; BAUSCH + LOMB IRELAND LIMITED
To: CITIBANK, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 071773/0871 →
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 →
PATENT SECURITY AGREEMENT Recorded Oct 4, 2023
From: BAUSCH & LOMB INCORPORATED
To: CITIBANK, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 065120/0086 →
OMNIBUS PATENT SECURITY RELEASE AGREEMENT (REEL/FRAME 043251/0932) Recorded Nov 2, 2022
From: THE BANK OF NEW YORK MELLON
To: BAUSCH & LOMB INCORPORATED; TECHNOLAS PERFECT VISION GMBH
Reel/Frame 061872/0099 →
OMNIBUS PATENT SECURITY RELEASE AGREEMENT (REEL/FRAME 045444/0634) Recorded Nov 2, 2022
From: THE BANK OF NEW YORK MELLON
To: BAUSCH & LOMB INCORPORATED; LABORATOIRE CHAUVIN S.A.S.; TECHNOLAS PERFECT VISION GMBH; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES
Reel/Frame 061872/0295 →
OMNIBUS PATENT SECURITY RELEASE AGREEMENT (REEL/FRAME 048556/0758) Recorded Nov 2, 2022
From: THE BANK OF NEW YORK MELLON
To: BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH COMPANIES INC.; TECHNOLAS PERFECT VISION GMBH; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES
Reel/Frame 061872/0484 →
OMNIBUS PATENT SECURITY RELEASE AGREEMENT (REEL/FRAME 056811/0814) Recorded Nov 2, 2022
From: THE BANK OF NEW YORK MELLON
To: BAUSCH & LOMB INCORPORATED
Reel/Frame 061872/0669 →
OMNIBUS PATENT SECURITY RELEASE AGREEMENT (REEL/FRAME 059121/0001) Recorded Nov 2, 2022
From: THE BANK OF NEW YORK MELLON
To: BAUSCH & LOMB INCORPORATED
Reel/Frame 061873/0001 →
RELEASE OF SECURITY INTEREST IN SPECIFIED PATENTS (REEL/FRAME 034749/0689) Recorded Oct 26, 2022
From: BARCLAYS BANK PLC
To: BAUSCH & LOMB INCORPORATED; UNIVERSITY OF ROCHESTER
Reel/Frame 061778/0146 →
RELEASE OF SECURITY INTEREST IN SPECIFIED PATENTS (REEL/FRAME 045444/0299) Recorded Oct 26, 2022
From: BARCLAYS BANK PLC
To: BAUSCH & LOMB INCORPORATED; TECHNOLAS PERFECT VISION GMBH; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; PF CONSUMER HEALTHCARE 1 LLC; LABORATOIRE CHAUVIN S.A.S.
Reel/Frame 061779/0001 →
RELEASE OF SECURITY INTEREST IN SPECIFIED PATENTS (REEL/FRAME 031156/0508) Recorded Oct 26, 2022
From: BARCLAYS BANK PLC
To: BAUSCH & LOMB INCORPORATED
Reel/Frame 061778/0446 →
PATENT SECURITY AGREEMENT Recorded May 10, 2022
From: BAUSCH & LOMB INCORPORATED
To: CITIBANK, N.A. AS COLLATERAL AGENT
Reel/Frame 059913/0548 →
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 →
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: BAUSCH & LOMB INCORPORATED
To: THE BANK OF NEW YORK MELLON
Reel/Frame 043251/0932 →