Amphiphilic block copolymers and their use

• US 20060134177A1
• Filed: 12/20/2005
• Published: 06/22/2006
• Est. Priority Date: 12/20/2004
• Status: Active Grant

• Current Assignee: Amo Groningen B.V (Johnson & Johnson)
• Original Assignee: Amo Groningen B.V (Johnson & Johnson)
• Inventors: Haitjema, Hendrik Jan, Norrby, Sverker, Liu, Yan, Terwee, Thom, Hilborn, Jons Gunnar
• Granted Patent: US 7,847,025 B2
• Time in Patent Office: Days
• US Class Current: 424/427
• CPC Class Codes: A61K 31/695 Silicon compounds
• CPC Class Codes: A61L 24/046 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L24/043 takes precedence
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: Y10S 623/926 Synthetic

Abstract

The present invention relates to amphiphilic block copolymers comprising at least one block of hydrophilic units and at least one block of hydrophobic units, wherein at least one hydrophobic block contains siloxane units. The present invention may be particularly useful as a tissue adhesive or as a coating for an intraocular lens (IOL). As an IOL coating, copolymers according to the invention may be used, for example, to promote tissue adhesion for the prevention of posterior capsule opacification.

Claims

1. A coating composition for adhering an implant to a biological tissue comprising an amphiphilic block copolymer having at least one block of hydrophilic units and at least one block of hydrophobic units characterized in that said at least one hydrophobic block contains siloxane units.

2. The composition according to claim 1, characterized in that said siloxane units comprises a copolymer having the formula:

3. The composition according claim 2, characterized in that said hydrophobic copolymer is a terpolymer in which R₁, R₂ and R₆ are methyl, R₃ and R₄ are phenyl and R₅ is trifluorpropyl.

4. The composition according to claim 3, characterized in that the terpolymers have terminal amino groups.

5. The composition according to any one of claim 1, characterized in that said at least one block of hydrophilic units comprises a polymer selected from the group consisting of poly(vinyl alcohol), poly(ethylene glycol), poly(hydroxyethyl methacrylate), polyacrylamide, poly(N-vinyl-pyrrolidone), polyacrylic acid, poly(methacrylic acid), poly(maleic anhydride) and polymaleic acid.

6. The composition according to claim 5, characterized in that said at least one block of hydrophilic units are poly(ethylene glycol).

7. The composition according to claim 1, characterized in that said at least one hydrophilic block comprises terminal or lateral functional groups.

8. The composition according to claim 7 wherein said terminal or lateral groups are selected from functional groups which are water stable and which capable of reacting with nucleophilic groups, preferably amino-groups.

9. The composition according to claim 7, wherein said terminal or lateral functional groups are selected from the group consisting of isocyanates, isothiocyanates, acrylates, maleinates, N-hydroxysuccimide esters and cyanoacrylates.

10. The composition according to claim 9, wherein said terminally functional groups are selected from isothiocyanates.

11. The composition according to claim 1, wherein said at least one hydrophilic block is formed from a precursor with the structure

12. The composition according to claim 1, wherein said amphiphilic block copolymer is an isothiocyanate terminated poly(ethylene glycol)-b-polysiloxane having the formula:

13. The composition according to claim 1 characterized in that said composition is an ophthalmic composition.

14. The composition according to claim 1 characterized in that said composition is an aqueous emulsion.

15. An amphiphilic block copolymer comprising at least one block of hydrophilic units and at least one block of hydrophobic units characterized in that said at least one hydrophobic block contains siloxane units and said at least one hydrophilic block comprises terminal or lateral functional groups.

16. The amphiphilic block copolymer according to claim 15, characterized in that said siloxane units comprises a copolymer having the formula:

17. The amphiphilic block copolymer according claim 16, characterized in that said hydrophobic copolymer is a terpolymer in which R₁, R₂ and R₆ are methyl, R₃ and R₄ are phenyl and R₅ is trifluorpropyl.

18. The amphiphilic block copolymer according to claim 17, characterized in that the terpolymers have terminal amino groups.

19. The amphiphilic block copolymer according to claim 15, characterized in that said at least one block of hydrophilic units comprises a polymer selected from the group consisting of poly(vinyl alcohol), poly(ethylene glycol), poly(hydroxyethyl methacrylate), polyacrylamide, poly(N-vinyl-pyrrolidone), polyacrylic acid, poly(methacrylic acid), poly(maleic anhydride) and polymaleic acid.

20. The amphiphilic block copolymer according to claim 19, characterized in that said at least one block of hydrophilic units are poly(ethylene glycol).

21. The amphiphilic block copolymer according to claim 15, wherein said terminal or lateral groups are selected from functional groups which are water stable and which capable of reacting with nucleophilic groups, preferably amino-groups.

22. The amphiphilic block copolymer according to claim 21, wherein said terminal or lateral functional groups are selected from the group consisting of isocyanates, isothiocyanates, acrylates, maleinates, N-hydroxysuccimide esters and cyanoacrylates.

23. The amphiphilic block copolymer according to claim 22, wherein said terminally functional groups are selected from isothiocyanates.

24. The amphiphilic block copolymer according to claim 15, wherein said at least one hydrophilic block is formed from a precursor with the structure

25. The amphiphilic block copolymer according to claim 15, wherein said amphiphilic block copolymer is an isothiocyanate terminated poly(ethylene glycol)-b-polysiloxane having the formula:

26. An ophthalmic lens at least partially coated with a coating composition comprising an amphiphilic block copolymer having at least one block of hydrophilic units and at least one block of hydrophobic units characterized in that said at least one hydrophobic block contains siloxane units.

27. The ophthalmic lens according to claim 26 being an intraocular lens.

28. The ophthalmic lens according to claim 27 having its posterior side coated with said coating composition.

29. The ophthalmic lens according to claim 27, comprising a toric lens.

30. A method for providing a connection between a tissue surface and an implant or drug delivery device, comprising applying a composition between the tissue surface and the implant or drug delivery device, wherein the composition comprises an amphiphilic block copolymer having at least one block of hydrophilic units and at least one block of hydrophobic units characterized in that said at least one hydrophobic block contains siloxane units.

31. The method of claim 30, wherein the implant is a breast implant.

32. A method for reducing secondary cataract characterized in that a composition is injected into the capsular bag of an eye, wherein the composition comprises an amphiphilic block copolymer having at least one block of hydrophilic units and at least one block of hydrophobic units characterized in that said at least one hydrophobic block contains siloxane units.

33. A method according to claim 32 characterized in that it comprises the following steps:

a. removal of the natural lens;

b. injection of the composition; and

c. injection of a intraocular lens.

34. A joint structure characterized in that said structure comprises amphiphilic block copolymers in which at least one hydrophilic block interacts with the tissue surface and in which at least one hydrophobic block comprises hydrophobic polymers capable of interacting with an implant whereby a laminate comprising the tissue surface, amphiphilic copolymers and the implant is obtained.

35. The joint structure according to claim 34, wherein the joint structure is configured to form a connection between an implant and a tissue surface.