Coatings for implantable devices comprising poly(hydroxy-alkanoates) and diacid linkages

• US 8,586,075 B2
• Filed: 11/27/2012
• Issued: 11/19/2013
• Est. Priority Date: 07/30/2004
• Status: Expired due to Fees

• Current Assignee: Abbott Cardiovascular Systems Incorporated (Abbott Laboratories Incorporated)
• Original Assignee: Abbott Cardiovascular Systems Incorporated (Abbott Laboratories Incorporated)
• Inventors: Pacetti, Stephen Dirk, Glauser, Thierry
• Primary Examiner(s): Switzer, Juliet
• Assistant Examiner(s): HELM, CARALYNNE E
• Application Number:
  US13/686,380
• Publication Number:
  US 20130123422A1
• Time in Patent Office: 357 Days
• Field of Search: None
• US Class Current: 424/426
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: C08G 63/66 Polyesters containing oxygen in the form of ether groups C08G63/42, C08G63/58 take precedence
• CPC Class Codes: C09D 167/00 Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain based on polyester-amides C09D177/12; based on polyester-imides C09D179/08; Coating compositions based on derivatives of such polymers

Abstract

Coatings for an implantable medical device and a method of fabricating thereof are disclosed, the coatings include block-polymers comprising at least one poly(hydroxyacid) or poly(hydroxy-alkanoate) block, at least one block of a biologically compatible polymer and at least one type of linking moiety.

Claims

1. A polymer having the formula:

A-X-A-B_n

wherein;

A are poly(hydroxyacid) or poly(hydroxy-alkanoate) blocks;

B are blocks of a biologically compatible polymer;

X is a linking moiety; and

n is an integer between 2 and 700;

wherein the linking moiety is derived from at least one of or any combination of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, brassylic acid, dodecane-1,12-dicarboxylic acid, tridecane-1,13-dicarboxylic acid, thapsic acid, fumaric acid, maleic acid, and 1,3-acetonedicarboxylic acid;

wherein the biologically compatible polymer is poly(L-lysine)-graft-co-poly(ethylene glycol; and

wherein the poly(hydroxyacid) or poly(hydroxy-alkanoate) is one of poly(lactide-co-glycolide);

poly(L-lactide);

poly(D-lactide);

poly(D,L-lactide);

poly(L-lactide-co-glycolide);

poly(D,L-lactide-co-glycolide);

poly(L-lactide-co-caprolactone);

poly(D,L-lactide-co-caprolactone);

poly(L-lactide-co-D,L-lactide);

poly(L-lactide-co-trimethylene carbonate);

poly(D,L-lactide-co-trimethylene carbonate);

poly(L-lactic acid);

poly(D-lactic acid);

poly(D,L-lactic acid);

or a combination thereof.

2. The polymer of claim 1 wherein the poly(hydroxyacid) or poly(hydroxy-alkanoate) is one of poly(L-lactide);

poly(D-lactide);

poly(D,L-lactide);

poly(L-lactide-co-D,L-lactide);

poly(L-lactic acid);

poly(D-lactic acid);

poly(D,L-lactic acid);

or a combination thereof.

3. The polymer of claim 1 wherein the linking moiety is derived from at least one of or any combination of malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, brassylic acid, dodecane-1,12-dicarboxylic acid, tridecane-1,13-dicarboxylic acid, thapsic acid, fumaric acid, maleic acid, and 1,3-acetonedicarboxylic acid.

4. The polymer of claim 1 wherein the linking moiety is derived from at least one of or any combination of glutaric acid, adipic acid, pimelic acid, brassylic acid, dodecane-1,12-dicarboxylic acid, tridecane-1,13-dicarboxylic acid, thapsic acid, fumaric acid, maleic acid, and 1,3-acetonedicarboxylic acid.

5. The polymer of claim 1 wherein each A is a poly(D,L-lactide) block.

6. The polymer of claim 5 wherein n is about 10.

13. A coating made with the polymer of claim 1.

14. A coating made with the polymer of claim 2.

15. A coating made with the polymer of claim 4.

16. A coating made with the polymer of claim 5.

17. A medical device comprising the coating of claim 13.

18. A medical device comprising the coating of claim 14.

19. A medical device comprising the coating of claim 15.

20. A medical device comprising the coating of claim 16.

7. A method of making a polymer comprising:

reacting at least one poly(hydroxyacid) or poly(hydroxy-alkanoate) with at least one chain extending compound that is derived from at least one of or any combination of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, brassylic acid, dodecand-1,12-dicarboxylic acid, tridacane-1,13-dicarboxlic acid, thapsic acid, fumaric acid, maleic acid, and 1,3-acetonedicarboxylic acid, such that an A-X-A block polymer is formed; and

reacting the A-X-A block copolymer with a biologically compatible polymer such that a final block copolymer is formed having the formula;

A-X-A-B_n

wherein A are poly(hydroxyacid) or poly(hydroxy-alkanoate) blocks;

B are blocks of the biologically compatible polymer;

X is a linking moiety that corresponds to the chain extending compound; and

n is an integer between 2 and 700;

wherein the biologically compatible polymer is poly(L-lysine)-graft-co-poly(ethylene glycol); and

wherein the poly(hydroxyacid) or poly(hydroxy-alkanoate) is one of poly(lactide-co-glycolide);

poly(L-lactide);

poly(D-lactide);

poly(D,L-lactide);

poly(L-lactide-co-glycolide);

poly(D,L-lactide-co-glycolide);

poly(L-lactide-co-caprolactone);

poly(D,L-lactide-co-caprolactone);

poly(L-lactide-co-D,L-lactide);

poly(L-lactide-co-trimethylene carbonate);

poly(D,L-lactide-co-trimethylene carbonate);

poly(L-lactic acid);

poly(D-lactic acid);

poly(D,L-lactic acid);

or any combination of these.

8. The method of claim 7 further comprising:

depositing the final block copolymer on a region of an implantable portion of a medical device.

9. The method of claim 8 wherein the medical device is a stent.

10. The method of claim 7 wherein the poly(hydroxyacid) or poly(hydroxy-alkanoate) is one of a poly(lactide), poly(lactic acid), poly(lactide-co-glycolide), or a mixture thereof.

11. The method of claim 7 wherein the chain extending compound is a dicarboxylic acid, di-acid chloride, an anhydride, or a diisocyanate.

12. The method of claim 7 wherein the chain extending compound is one of or any combination of oxalic acid, malonic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, nonane-1,9-dicarboxylic acid, decane-1,10-dicarboxylic acid, brassylic acid, dodecane-1,12-dicarboxylic acid, tridecane-1,13-dicarboxylic acid, thapsic acid, terephthalic acid, fumaric acid, maleic acid, and 1,3-acetonedicarboxylic acid.