OPHTHALMIC DEVICES FOR DELIVERY OF HYDROPHOBIC COMFORT AGENTS

• US 20100140114A1
• Filed: 12/03/2009
• Published: 06/10/2010
• Est. Priority Date: 12/05/2008
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Nelson, Jared, Winterton, Lynn Cook, Pruitt, John Dallas
• Granted Patent: US 10,155,349 B2
• Time in Patent Office: Days
• US Class Current: 206/5.100
• CPC Class Codes: A61K 9/0051 Ocular inserts, ocular implants
• CPC Class Codes: B29D 11/00067 Hydrating contact lenses
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The invention relates to a soft hydrogel contact lens, especially a silicone hydrogel contact lens, which has a capability of delivering a hydrophobic comfort agent into the eye of a wearer. The hydrophobic comfort agent includes without limitation a monoglyceride, a diglyceride, a triglyceride, a glycolipid, a glyceroglycolipid, a sphingolipid, a sphingo-glycolipid, a phospholipid, a fatty acid, a fatty alcohol, a hydrocarbon having a C₁₂-C₂₈ chain in length, a mineral oil, a silicone oil, or a mixture thereof. It can be released from the soft hydrogel contact lens into the eye of a wearer when being worn so as to strengthen and stabilize the tear film lipid layer and alleviate the dryness of the eye.

Claims

1. A soft hydrogel contact lens, comprising:

a polymeric matrix and a hydrophobic comfort agent which is not covalently linked to the polymer matrix but distributed therein, wherein the polymeric matrix comprises hydrophobic units derived from a silicone-containing monomer or macromer and/or a hydrophobic monomer and hydrophilic units derived from a hydrophilic monomer or macromer,

wherein the hydrophobic comfort agent comprises a phospholipid, a monoglyceride, a diglyceride, a triglyceride, a glycolipid, a glyceroglycolipid, a sphingolipid, a sphingo-glycolipid, a fatty acid, a fatty alcohol, a hydrocarbon having a C₁₂-C₂₈ chain in length, or a mixture thereof,

wherein the soft contact lens is characterized by its capability of gradually releasing the hydrophobic comfort agent from the polymer matrix into the eye of a wearer when being worn.

2. The soft hydrogel contact lens of claim 1, wherein the soft hydrogel contact lens has at least one property selected from the group consisting of an oxygen permeability of at least about 40 barrers, an elastic modulus of from about 0.2 MPa to about 2.0 MPa, an Ionoflux Diffusion Coefficient, D, of at least about 1.5×

10<sup>−

6</sup> mm²/min, a water content of from about 15% to about 70%, a surface hydrophilicity characterized by having an averaged water contact angle of about 90 degrees or less, and combination thereof.

3. The soft hydrogel contact lens of claim 2, wherein the hydrophobic comfort agent is a phospholipid.

4. The soft hydrogel contact lens of claim 2, wherein the hydrophobic comfort agent is a monoglyceride, a diglyceride, a triglyceride, or mixture thereof.

5. The soft hydrogel contact lens of claim 2, wherein the hydrophobic comfort agent is a glycolipid, a glyceroglycolipid, or a mixture thereof.

6. The soft hydrogel contact lens of claim 2, wherein the hydrophobic comfort agent is a sphingolipid, a sphingo-glycolipid, or a mixture thereof.

7. The soft hydrogel contact lens of claim 2, wherein the hydrophobic comfort agent is a fatty acid, a fatty alcohol, a hydrocarbon having a C₁₂-C₂₈ chain in length, or a mixture thereof.

8. The soft hydrogel contact lens of claim 2, wherein the soft hydrogel contact lens further comprises a non-crosslinkable hydrophilic polymer as a leachable wetting agent.

9. The soft hydrogel contact lens of claim 8, wherein the non-crosslinkable hydrophilic polymer is:

a polyvinylalcohol;

polyethylene oxide;

a polyethylene-polypropylene block copolymer;

a polyamide;

a polyimide;

a polylactone;

polyvinylpyrrolidone;

a copolymer of N-vinylpyrrolidone and one or more hydrophilic vinylic monomers;

a homopolymer of acrylamide or methacrylamide;

a copolymer of acrylamide or methacrylamide with one or more hydrophilic vinylic monomers;

a homopolymer of N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, or N-vinyl-N-methyl acetamide;

a copolymer of N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, or N-vinyl-N-methyl acetamide with one or more hydrophilic vinylic monomers, and a mixture thereof.

10. An ophthalmic product, comprising:

a sealed package which include a packaging solution and a soft hydrogel contact lens, wherein the hydrogel contact lens comprises a polymer matrix and a hydrophobic comfort agent which is not covalently linked to the polymer matrix but distributed therein,

wherein the polymeric matrix comprises hydrophobic units derived from a silicone-containing monomer or macromer and/or a hydrophobic monomer and hydrophilic units derived from a hydrophilic monomer or macromer,

wherein the hydrophobic comfort agent comprises a monoglyceride, a diglyceride, a triglyceride, a glycolipid, a glyceroglycolipid, a sphingolipid, a sphingo-glycolipid, a phospholipid, a fatty acid, a fatty alcohol, a hydrocarbon having a C₁₂-C₂₈ chain in length, a mineral oil, a silicone oil, or a mixture thereof,

wherein the soft contact lens has a capability of gradually releasing the hydrophobic comfort agent during wear over at least about 4 hours after storing in the packaging solution for at least about one month.

11. The ophthalmic product of claim 10, wherein the soft hydrogel contact lens has at least one property selected from the group consisting of an oxygen permeability of at least about 40 barrers, an elastic modulus of from about 0.2 MPa to about 2.0 MPa, an Ionoflux Diffusion Coefficient, D, of at least about 1.5×

10<sup>−

6</sup> mm²/min, a water content of from about 15% to about 70%, a surface hydrophilicity characterized by having an averaged water contact angle of about 90 degrees or less, and combination thereof.

12. The ophthalmic product of claim 11, wherein the hydrophobic comfort agent is a phospholipid.

13. The ophthalmic product of claim 11, wherein the hydrophobic comfort agent is a monoglyceride, a diglyceride, a triglyceride, or mixture thereof.

14. The ophthalmic product of claim 11, wherein the hydrophobic comfort agent is a glycolipid, a glyceroglycolipid, or a mixture thereof.

15. The ophthalmic product of claim 11, wherein the hydrophobic comfort agent is a sphingolipid, a sphingo-glycolipid, or a mixture thereof.

16. The ophthalmic product of claim 11, wherein the hydrophobic comfort agent is a fatty acid, a fatty alcohol, a hydrocarbon having a C₁₂-C₂₈ chain in length, or a mixture thereof.

17. The ophthalmic product of claim 11, wherein the soft hydrogel contact lens further comprises a non-crosslinkable hydrophilic polymer as leachable wetting agent, wherein the non-crosslinkable hydrophilic polymer is:

a polyvinylalcohol;

polyethylene oxide;

a polyethylene-polypropylene block copolymer;

a polyamide;

a polyimide;

a polylactone;

polyvinylpyrrolidone;

a copolymer of N-vinylpyrrolidone and one or more hydrophilic vinylic monomers;

a homopolymer of acrylamide or methacrylamide;

a copolymer of acrylamide or methacrylamide with one or more hydrophilic vinylic monomers;

a homopolymer of N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, or N-vinyl-N-methyl acetamide;

a copolymer of N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, or N-vinyl-N-methyl acetamide with one or more hydrophilic vinylic monomers, and a mixture thereof.

18. The ophthalmic product of claim 11, wherein the packaging solution comprises from about 0.01% to about 5% by weight of a viscosity-enhancing polymer, wherein the viscosity-enhancing polymer is a water soluble cellulose ether, a water-soluble polyvinylalcohol, a poly(ethylene oxide) having a molecular weight of from about 2000 to about 10,000,000 daltons, a polyvinylpyrrolidone with a molecular weight of from about 30,000 daltons to about 1,000,000 daltons, a copolymer of vinylpyrrolidone with one or more hydrophilic monomers, or a mixture thereof, wherein the water-soluble cellulose ether is methyl cellulose (MC), ethyl cellulose, hydroxymethylcellulose, hydroxyethyl cellulose (HEC), hydroxypropylcellulose (H PC), hydroxypropylmethyl cellulose (HPMC), or a mixture thereof.

19. A process for making a soft contact lens capable of gradually delivering a hydrophobic comfort agent during wearing of the contact lens, comprising the steps of:

a) dipping a soft hydrogel contact lens in a solution containing a hydrophobic comfort agent and an organic solvent miscible with water, wherein the soft hydrogel contact lens comprises a polymer matrix including hydrophobic units derived from a silicone-containing monomer or macromer and/or a hydrophobic monomer and hydrophilic units derived from a hydrophilic monomer or macromer, wherein the hydrophobic comfort agent comprises a monoglyceride, a diglyceride, a triglyceride, a glycolipid, a glyceroglycolipid, a sphingolipid, a sphingo-glycolipid, a phospholipid, a fatty acid, a fatty alcohol, a hydrocarbon having a C₁₂-C₂₈ chain in length, a mineral oil, a silicone oil, or a mixture thereof, wherein the organic solvent swells the soft hydrogel contact so as to allow the hydrophobic comfort agent to be penetrate and incorporate into the polymer matrix of the soft hydrogel contact lens;

b) hydrating the soft hydrogel contact lens having the comfort agent distributed therein in water or a buffered aqueous solution; and

c) placing and sealing the hydrated soft hydrogel contact lens in a lens package containing a lens packaging solution,

wherein the soft contact lens is characterized by its capability of gradually releasing the hydrophobic comfort agent from the polymer matrix into the eye of a wearer when being worn.

20. A method for making a soft hydrogel contact lens capable of gradually delivering a hydrophobic comfort agent during wearing of the contact lens, comprising the steps of:

a) obtaining a fluid prepolymer composition comprising a first organic solvent, an actinically-crosslinkable lens-forming material, and a hydrophobic comfort agent, wherein the actinically-crosslinkable lens-forming material comprises actinincally-crosslinkable groups and can be polymerized thermally or actinically to form the polymer matrix of the soft contact lens, wherein the actinically-crosslinkable lens-forming material comprises monomer, macromer, and/or prepolymer, wherein the hydrophobic comfort agent is free of any actinically-crosslinkable group and comprises a monoglyceride, a diglyceride, a triglyceride, a glycolipid, a glyceroglycolipid, a sphingolipid, a sphingo-glycolipid, a phospholipid, a fatty acid, a fatty alcohol, a hydrocarbon having a C₁₂-C₂₈ chain in length, a mineral oil, a silicone oil, or a mixture thereof;

b) introducing an amount of the fluid prepolymer composition in a mold for making a contact lens;

c) polymerizing the actinically-crosslinkable prepolymer in the mold to form the soft hydrogel contact lens with the hydrophobic comfort agent being not covalently linked to the polymer matrix but being distributed therein in a substantially uniform manner;

d) hydrating the resultant soft hydrogel contact lens in water or an aqueous solution to replace the first organic solvent with water or the aqueous solution;

e) packaging the hydrated soft contact lens in a container containing a packaging solution; and

f) sterilizing the soft contact lens in the package, wherein the sterilized soft contact lens is capable of gradually releasing the hydrophobic comfort agent during wear, provided that the method is free of any extraction step with a second organic solvent.