Methods of manufacturing contact lenses for delivery of beneficial agents

• US 9,248,928 B2
• Filed: 12/18/2013
• Issued: 02/02/2016
• Est. Priority Date: 12/21/2012
• Status: Active Grant

• Current Assignee: Coopervision International Limited (The Cooper Cos., Inc.)
• Original Assignee: Coopervision International Holding Company LP (The Cooper Cos., Inc.)
• Inventors: Rogers, Victoria, Luk, Andrew, Back, Arthur, Chen, Charlie
• Primary Examiner(s): Salamon, Peter A
• Application Number:
  US14/109,978
• Publication Number:
  US 20140179825A1
• Time in Patent Office: 776 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: A61K 9/0048 Eye, e.g. artificial tears
• CPC Class Codes: B29D 11/00096 for delivering compositions, e.g. drugs to the eye
• CPC Class Codes: B65B 23/00 Packaging fragile or shock-sensitive articles other than bottles; Unpacking eggs embedding articles in shock-absorbing media B65B55/20
• CPC Class Codes: B65B 25/008 packaging of contact lenses
• CPC Class Codes: C08L 33/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Contact lenses comprising an ionic component are packaged with a beneficial cationic agent in a temperature-sensitive packaging solution and/or a low ionic strength packaging solution.

Claims

1. A method of manufacturing a contact lens, said method comprising:

a) polymerizing a monomer mixture comprising at least one carboxylic-acid containing monomer to form a lens-shaped polymerization product comprising carboxylic acid groups;

b) placing the lens-shaped polymerization product in a package containing a packaging solution comprising a buffer and a beneficial cationic agent, wherein said packaging solution has an osmolality of about 200 to about 400 mOsm/kg, and wherein said packaging solution i) has an ionic strength of less than about 0.1, or ii) is temperature-sensitive, or iii) has an ionic strength of less than about 0.1 and is temperature-sensitive; and

c) sealing and autoclaving the package to provide a sterile packaged contact lens, wherein the beneficial cationic agent ionically binds to the carboxylic acid groups and releases from the contact lens in an in vitro release assay;

wherein at least 50% more of the cationic agent is taken up by the lens compared to an identical contact lens packaged in PBS.

2. The method of claim 1, wherein the carboxylic-acid containing monomer is methacrylic acid.

3. The method of claim 1, wherein the contact lens comprises from about 0.5 to about 2.5% methacrylic acid.

4. The method of claim 3, wherein the methacrylic acid is the only ionic monomer in the monomer mixture.

5. The method of claim 1, wherein the monomer mixture comprises a silicone monomer.

6. The method of claim 1, wherein the monomer mixture comprises 2-hydroxyethyl methacrylate.

7. The method of claim 1, wherein the ionic strength of the packaging solution is less than 0.1.

8. The method of claim 1, wherein the ionic strength of the packaging solution is less than 0.06.

9. The method of claim 1, wherein in the packaging solution comprises a non-electrolyte tonicity adjusting agent.

10. The method of claim 9, wherein the tonicity adjusting agent is sorbitol.

11. The method of claim 1, wherein the packaging solution has an osmolality of about 270 to about 310 mOsm/kg.

12. The method of claim 1, wherein the cationic agent is a polymer.

13. The method of claim 1, wherein the cationic agent is an ophthalmic drug.

14. The method of claim 1, wherein the packaging solution comprises a temperature-sensitive buffer and the cationic agent is autoclave-stable in the packaging solution and is not autoclave-stable in PBS.

15. The method of claim 14, wherein the temperature-sensitive buffer comprises a buffering agent selected from {[tris(hydroxymethyl)methyl]amino}propanesulfonic acid (TAPS), N,N-bis(21-hydroxyethyl)glycine (Bicine), tris(hycroxymethyl)methylamine (TRIS), N-tris(hydroxymethyl)methylglycine (Tricine), [tris(hydroxymethyl)methyl]amino}ethanesulfonic acid (TES), 3-(N-morpholino)propanesulfonic acid (MOPS), and any combination thereof.

16. The method of claim 14, wherein the temperature-sensitive buffer comprises a TRIS buffer.

17. The method of claim 14, wherein the cationic agent comprises a primary amine.

18. The method of claim 14, wherein the cationic agent is epinastine and/or ε

PLL.

19. The method of claim 1, further comprising storing the contact lens after it has been worn by a patient in a multi-purpose contact lens care solution (MPS) that comprises an additional amount of the cationic agent, wherein the storage solution has an osmolality of about 200 to about 400 mOsm/kg and has an ionic strength of less than about 0.1, wherein the additional cationic agent incorporates into the contact lens during the storage.

20. A contact lens made by the method of claim 1.