Medical device coatings

1. A coating comprising polyethylene glycol and at least one polyphenolic polymer, wherein the polyethylene glycol is selected from the group consisting of PEG-3350, PEG-1000, and PEG-400.

2. The coating of claim 1 , wherein the polyphenolic polymer is selected from the group consisting of tyrosine-derived polyarylates, linear polyesteramides, dihydroxybenzoate polymers, and resorcinol-derived polymers.

3. The coating of claim 2 , wherein the tyrosine-derived polyarylate comprises monomer units having the formula:

wherein R 1 is CH═CH or (CH 2 ) n ;

n is an integer ranging from 0 to 18;

Y is selected from the group consisting of C 1 -C 18 alkylamino, —OR′, —NHCH 2 CO 2 R′, —NH(CH 2 ) q OR′, —NH(CH 2 CH 2 O) p R′, —NH(CH 2 CH 2 CH 2 O) p R′,

q is an integer ranging from 0 to 4;

p is an integer ranging from 1 to 5000;

R′ is independently selected from the group consisting of H, C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 8 -C 14 alkylaryl, benzyl, and substituted benzyl;

R 2 is independently selected from the group consisting of a divalent, linear or branched, substituted or unsubstituted alkylene, alkenylene, alkynylene, arylene, alkylarylene, alkyl ether or aryl ether moiety having from 1 to 30 carbon atoms; —(R s ) q O((CR 3 R 4 ) r O) s (R 5 ) q —; and —(R 5 ) q CO 2 ((CR 3 R 4 ) r O) s CO(R 5 ) q —,

R 3 and R 4 are independently selected from the group consisting of hydrogen and a linear or branched, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms; and

R 5 is independently a linear or branched, lower alkylene or lower alkenylene group.

4. The coating of claim 2 , wherein the linear polyesteramide comprises monomer units having the formula:

wherein R is —(CR 3 R 4 ) a — or —CR 3 ═CR 4 —;

R 1 is selected from the group consisting of hydrogen and a saturated or unsaturated alkyl, aryl, alkylaryl or alkyl ether having from 1 to 20 carbon atoms; or —(R 5 ) q O((CR 3 R 4 ) r O) s —R 6 ;

R 2 is independently selected from the group consisting of a divalent, linear or branched, substituted or unsubstituted alkylene, alkenylene, alkynylene, arylene, alkylarylene, alkyl ether or aryl ether moiety having from 1 to 30 carbon atoms; —(R 5 ) q O((CR 3 R 4 ) r O) s (R 5 ) q , and —(R 5 ) q CO 2 ((CR 3 R 4 ) r O) s CO(R 5 ) q ;

R 3 and R 4 are independently selected from the group consisting of hydrogen and a linear or branched, substituted or unsubstituted alkyl group having between 1 and 10 carbon atoms;

R 5 is independently a linear or branched, lower alkylene or lower alkenylene group;

R 6 is independently selected from the group consisting of a linear or branched, substituted or unsubstituted, saturated or unsaturated lower alkyl;

the aromatic ring has from zero to four Z 1 substituents, each of which is independently selected from the group consisting of halide, lower alkyl, alkoxy, nitro, alkyl ether, a protected hydroxyl group, a protected amino group and a protected carboxylic acid group;

Y is selected from

a is 0 to 10;

q is independently 1 to 4;

r is independently 1 to 4; and

s is independently 1 to 5000.

5. The coating of claim 2 , wherein the dihydroxybenzoate polymer comprises monomer units having the formula:

wherein

A is selected from the group consisting of C(O), C(O)—R 1 —C(O), C(═N), C(O)—NH—R 1 —NH—C(O) or C(S);

W is O, NH or S

R is selected from the group consisting of hydrogen, an ester or amide protecting group, a leaving group, a linear or branched, substituted or unsubstituted, alkyl, alkenyl, alkynyl, aryl, alkylaryl, alkoxyether, heteroaryl, heteroalkyl or cycloalkyl group having from 1 to 30 carbon atoms, (R 2 ) r O((CR 3 R 4 ) a (O) s (R 2 ) r , a sugar, a pharmaceutically-active compound, and a biologically-active compound, wherein each a is independently 1 to 4, each b is independently 0 or 1, r is independently 1 to 4, and each s is independently 1 to 5000;

R 1 is independently selected from the group consisting of a divalent, linear or branched, substituted or unsubstituted alkyl, alkenyl, aryl, alkylaryl, alkylene oxide or arylene oxide moiety having from 1 to 30 carbon atoms, (R 2 ) r O((CR 3 R 4 ) a (O) s (R 2 ) r , or (R 2 ) r CO 2 ((CR 3 R 4 ) a (O) s CO(R 2 ) r , where each a is independently 1 to 4, each r is independently 1 to 4 and s is 1 to 5000;

R 2 is independently a linear or branched lower alkyl group; and

R 3 and R 4 are independently selected from the group consisting of hydrogen and a linear or branched lower alkyl group.

6. The coating of claim 2 , wherein the resorcinol-derived polymer comprises monomer units having the formula:

wherein

A is selected from the group consisting of C(O), C(O)—R 1 —C(O), C(═N), C(O)—NH—R 1 —NH—C(O) or C(S);

R is selected from the group consisting of hydrogen, halo, a linear or branched, substituted or unsubstituted, alkyl, alkenyl, alkynyl, aryl, alkylaryl, alkoxyether, heteroaryl, heteroalkyl or cycloalkyl group having from 1 to 30 carbon atoms, (R 2 ) b C(O)OR 2 , (R 2 ) r O((CR 3 R 4 ) a (O) s (R 2 ) r , a sugar, a pharmaceutically-active compound, and a biologically-active compound, wherein each a is independently 1 to 4, each b is independently 1 to 4, r is independently 1 to 4, and each s is independently 1 to 5000;

each R is independently selected from the group consisting of a divalent, linear or branched, substituted or unsubstituted alkyl, alkenyl, alkylene oxide or arylene oxide moiety having from 1 to 30 carbon atoms, (R 2 ) r O((CR 3 R 4 ) a O) s (R 2 ) r , or (R 2 ) r CO 2 ((CR 3 R 4 ) a (O) s CO(R 2 ) r , where each a is independently 1 to 4, each r is independently 1 to 4 and s is 1 to 5000;

R 2 is independently a linear or branched lower alkyl; and

R 3 and R 4 are independently hydrogen or linear or branched lower alkyl group.

7. The coating of claim 1 , wherein the polyethylene glycol is a poloxamer.

8. The coating of claim 1 , wherein the polyethylene glycol comprises at least one terminal group blocked with a methyl ether.

9. The coating of claim 1 , wherein the polyethylene glycol is a block copolymer comprising polyoxyethylene and polyoxypropylene units.

10. The coating of claim 3 , wherein the tyrosine-derived polyarylate comprises a member of the P22 family.

11. The coating of claim 10 , wherein the coating further comprises at least one antimicrobial ingredient.

12. The coating of claim 11 , wherein the antimicrobial ingredient is selected from the group consisting of minocycline, rifampin, and mixtures thereof.

13. The coating of claim 12 , wherein the PEG is PEG-400.

14. The coating of claim 10 , wherein the tyrosine-derived polyarylate has a percentage of free acid ranging from about 10% to about 30%.

15. The coating of claim 11 , wherein the percentage of free acid is about 27.5%.

16. The coating of claim 1 , further comprising about 20% to about 70% of at least one drug, based on the combined weight of the drug, polyethylene glycol and polyphenolic polymer.

17. The coating of claim 16 , wherein the at least one drug is selected from the group consisting of antimicrobial agents, anesthetics, analgesics, anti-inflammatory agents, anti-scarring agents, anti-fibrotic agents and leukotriene inhibitors.

18. The coating of claim 17 , wherein the at least one drug is an antimicrobial agent selected from the group consisting of antibiotics, antiseptics, and disinfectants.

19. The coating of claim 17 , wherein the at least one drug is an antibiotic selected from the group consisting of rifampin, minocycline, silver/chlorhexidine, and combinations thereof.

20. The coating of claim 19 , wherein the antibiotic comprises rifampin and minocycline.

21. A medical device comprising the coating of claim 1 .

22. The medical device of claim 21 , wherein the medical device is comprised of a material selected from the group consisting of a metal, an organic material, a natural or synthetic polymer or copolymer, and a material of biological origin.

23. The medical device of claim 21 , wherein a thickness of the coating ranges from 10 μm to about 250 μm.

24. The medical device of claim 21 , wherein a thickness of the coating ranges from 15 μm to about 125 μm.

25. A coating comprising about 10% to about 20% polyethylene glycol and about 80% to about 90% of at least one polyphenolic polymer based on the combined weight of the polyethylene glycol and polyphenolic polymer, wherein the polyethylene glycol is selected from the group consisting of PEG-3350, PEG-1000, and PEG-400.

26. The coating of claim 25 , further comprising at least one drug.

27. The coating of claim 1 , wherein the polyethylene glycol is unmodified.

28. A coating comprising polyethylene glycol and at least one polyphenolic polymer comprising tyrosine-derived polyarylates.

29. The coating of claim 28 , wherein the tyrosine-derived polyarylate comprises monomer units having the formula:

wherein R 1 is CH═CH or (CH 2 ) n ;

n is an integer ranging from 0 to 18;

Y is selected from the group consisting of C 1 -C 18 alkylamino, —OR′, —NHCH 2 CO 2 R′, —NH(CH 2 ) q OR′, —NH(CH 2 CH 2 O) p R′, —NH(CH 2 CH 2 CH 2 O) p R′,

q is an integer ranging from 0 to 4;

p is an integer ranging from 1 to 5000;

R′ is independently selected from the group consisting of H, C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 8 -C 14 alkylaryl, benzyl, and substituted benzyl;

R 2 is independently selected from the group consisting of a divalent, linear or branched, substituted or unsubstituted alkylene, alkenylene, alkynylene, arylene, alkylarylene, alkyl ether or aryl ether moiety having from 1 to 30 carbon atoms; —(R s ) q O((CR 3 R 4 ) r O) s (R 5 ) q —; and —(R 5 ) q CO 2 ((CR 3 R 4 ) r O) s CO(R 5 ) q —;

R 3 and R 4 are independently selected from the group consisting of hydrogen and a linear or branched, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms; and

R 5 is independently a linear or branched, lower alkylene or lower alkenylene group.

30. The coating of claim 28 , wherein the polyethylene glycol is unmodified.

31. The coating of claim 28 , wherein the polyethylene glycol is PEG-1000.

32. The coating of claim 28 , wherein the polyethylene glycol comprises at least one terminal functional group comprising an ether.

33. The coating of claim 28 , wherein the polyethylene glycol comprises nonionic triblock copolymers composed of a central hydrophobic chain of polyoxypropylene flanked by two hydrophilic chains of polyoxyethylene.

34. The coating of claim 28 , wherein the polyethylene glycol comprises block copolymers based on ethylene oxide.

35. The coating of claim 28 , wherein the polyethylene glycol comprises block copolymers based on propylene oxide.

36. The coating of claim 28 , wherein the polyethylene glycol is PEG diacid.

37. The coating of claim 28 , wherein the at least one polyphenolic polymer is P22-27.5.

38. The coating of claim 28 , wherein the polyethylene glycol comprises 0.1 to 25% by weight, based on the combined weight of the at least one polyphenolic polymer and the polyethylene glycol.

39. The coating of claim 28 , wherein the polyethylene glycol comprises 10 to 18% by weight, based on the combined weight of the at least one polyphenolic polymer and the polyethylene glycol.

40. The coating of claim 28 , wherein the polyethylene glycol is a Pluronic copolymer.

41. The coating of claim 40 , wherein the Pluronic copolymer is L44.