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

• US 8,357,391 B2
• Filed: 07/30/2004
• Issued: 01/22/2013
• Est. Priority Date: 07/30/2004
• Status: Expired due to Fees

• Current Assignee: Advanced Cardiovascular Systems Incorporated (Abbott Laboratories)
• Original Assignee: Advanced Cardiovascular Systems Incorporated (Abbott Laboratories)
• Inventors: Pacetti, Stephen D., Glauser, Thierry
• Primary Examiner(s): Switzer, Juliet
• Assistant Examiner(s): HELM, CARALYNNE E
• Application Number:
  US10/902,982
• Publication Number:
  US 20060034888A1
• Time in Patent Office: 3,098 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 including block-polymers comprising at least one poly(hydroxyacid) or poly(hydroxy-alkanoate) block, at least one block of a biologically compatible polymer and a linking moiety.

Claims

1. A polymer having the formula

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 any combination of these.

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 A are poly(D,L-lactide) blocks.

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 a biologically compatible polymer such that an A-B-A block copolymer is formed;

reacting the A-B-A block copolymer 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, dodecane-1,12-dicarboxylic acid, tridecane-1,13-dicarboxylic acid, thapsic acid, fumaric acid, maleic acid, and 1,3-acetonedicarboxylic acid such that a final block copolymer is formed having the formula

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 poly(L-lactide);

poly(D-lactide);

poly(D,L-lactide);

poly(L-lactic acid);

poly(D,L-lactic acid);

poly(D,L-lactic acid);

poly(lactide-co-glycolide);

or their mixtures.

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

12. The method of claim 11 wherein the chain extending compound is a dicarboxylic acid and the dicarboxylic acid is at least 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.