Carbodiimide crosslinking of functionalized polyethylene glycols

• US 7,910,129 B2
• Filed: 12/06/2006
• Issued: 03/22/2011
• Est. Priority Date: 12/06/2005
• Status: Active Grant

• Current Assignee: Covidien LP (Medtronic Plc)
• Original Assignee: Tyco Healthcare Group LP (Medtronic Plc)
• Inventors: Roby, Mark S., Kennedy, John, Hadba, Ahmad R.
• Primary Examiner(s): Hartley; Michael G
• Assistant Examiner(s): DICKINSON, PAUL W
• Application Number:
  US11/635,344
• Publication Number:
  US 20070148128A1
• Time in Patent Office: 1,567 Days
• Field of Search: None
• US Class Current: 424/443
• CPC Class Codes: A61K 31/74 Synthetic polymeric materials
• CPC Class Codes: A61L 24/0042 Materials resorbable by the body
• CPC Class Codes: A61L 24/043 Mixtures of macromolecular materials
• CPC Class Codes: C08G 65/329 with organic compounds
• CPC Class Codes: C08G 65/332 containing carboxyl groups, or halides, or esters thereof
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C08L 71/02 Polyalkylene oxides
• CPC Class Codes: C08L 79/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
• CPC Class Codes: C08L 79/08 Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors

Abstract

A synthetic composition is provided which includes an acid-functional polymer having at least one pendant acid group, an amine-functional polymer having at least one pendant amine group, and a coupling agent. The synthetic composition can be used in human and animal medical applications as an adhesive or sealant.

Claims

1. A synthetic absorbable macromer composition comprising:

an acid-functional polymer of formula (I);

2. A synthetic absorbable macromer composition as in claim 1, wherein R₁ comprises a polyethylene glycol.

3. A synthetic absorbable macromer composition as in claim 2, wherein the polyethylene glycol is selected from the group consisting of di-functional materials, tri-functional materials, tetra-functional materials and combinations thereof.

4. A synthetic absorbable macromer composition as in claim 1, wherein the acid-functional polymer further comprises at least one hydrolytically degradable component.

5. A synthetic absorbable macromer composition as in claim 1, wherein the acid-functional polymer further comprises at least one enzymatically degradable linkage.

6. A synthetic absorbable macromer composition as in claim 1, wherein the acid-functional polymer further comprises a non-functionalized amino acid selected from the group consisting of asparagine, glutamine, serine, threonine, tyrosine, glycine, alanine, valine, leucine, isoleucine, proline, phenylalanine, methionine, tryptophan, cysteine, and combinations thereof.

7. A synthetic absorbable macromer composition as in claim 1, wherein the acid-functional polymer is present in a range from about 20% to about 80% by weight of the synthetic absorbable macromer composition.

8. A synthetic absorbable macromer composition as in claim 1, wherein the amine-functional polymer is a polyamino acid selected from the group consisting of polylysine, polyornithine, polycysteine, polyarginine, polyhistidine, and combinations thereof.

9. A synthetic absorbable macromer composition as in claim 1, wherein the amine-functional polymer comprises a compound of formula (II):

10. A synthetic absorbable macromer composition of claim 9 wherein R₂ is a polyethylene glycol.

11. A synthetic absorbable macromer composition as in claim 10, wherein the polyethylene glycol is selected from the group consisting of di-functional materials, tri-functional materials, tetra-functional materials and combinations thereof.

12. A synthetic absorbable macromer composition as in claim 10, wherein the polyethylene glycol is terminated with amine end groups selected from a group consisting of primary amines, secondary amines, and combinations thereof.

13. A synthetic absorbable macromer composition as in claim 9, wherein the amine-functional polymer further comprises a non-functionalized amino acid selected from the group consisting of asparagine, glutamine, serine, threonine, tyrosine, glycine, alanine, valine, leucine, isoleucine, proline, phenylalanine, methionine, tryptophan, cysteine, and combinations thereof.

14. A synthetic absorbable macromer composition as in claim 9, wherein the amine-functional polymer further comprises at least one hydrolytically degradable component.

15. A synthetic absorbable macromer composition as in claim 9, wherein the amine-functional polymer further comprises at least one enzymatically degradable linkage.

16. An synthetic absorbable macromer composition as in claim 1, wherein the amine-functional polymer is present in a range from about 80% to about 20% by weight of the total synthetic absorbable macromer composition.

17. A synthetic absorbable macromer composition as in claim 1, wherein the carbodiimide is 1-ethyl -3(3-dimethyl-amino propyl)-carbodiimide hydrochloride.

18. An adhesive for wound closure comprising the synthetic absorbable macromer composition of claim 1.

19. A sealant for use in a medical application comprising the synthetic absorbable macromer composition of claim 1.

20. A method for closing a wound comprising:

applying the synthetic absorbable macromer composition of claim 1 to said wound; and

allowing the synthetic absorbable macromer composition to set thereby closing said wound.

21. The method of claim 20 wherein the wound is a surgical incision.

22. A method for filling a void in animal tissue comprising:

applying the synthetic absorbable macromer composition of claim 1 to said void; and

allowing the synthetic absorbable macromer composition to set thereby filling said void.

23. A method for adhering a medical device to a surface of animal tissue comprising the steps of:

applying the synthetic absorbable macromer composition of claim 1 to said device, said surface or both;

bringing the device, synthetic absorbable macromer composition and surface into contact with each other; and

allowing the synthetic absorbable macromer composition to set thereby adhering the device and surface to each other.

24. The method of claim 23 wherein said medical device is an implant.