BIOCOMPATIBLE POLYCAPROLACTONE FUMARATE FORMULATIONS

• US 20140099278A1
• Filed: 04/04/2012
• Published: 04/10/2014
• Est. Priority Date: 04/08/2011
• Status: Active Grant

• Current Assignee: Mayo Foundation For Medical Education And Research (Mayo Clinic)
• Original Assignee: Mayo Foundation For Medical Education And Research (Mayo Clinic)
• Inventors: Runge, Michael Brett, Yaszemski, Michael J.
• Granted Patent: US 10,426,867 B2
• Time in Patent Office: Days
• US Class Current: 424/78.17
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/26 Mixtures of macromolecular compounds
• CPC Class Codes: C08G 63/08 Lactones or lactides
• CPC Class Codes: C08G 63/60 derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence

Abstract

A polycaprolactone fumarate polymer useful as a matrix material for a biocompatible scaffold for tissue engineering applications is disclosed. The polycaprolactone fumarate polymer can be prepared by reacting caprolactone with an alkane polyol to prepare a polycaprolactone precursor, and then reacting the polycaprolactone precursor with fumaric acid or a salt thereof to prepare the polycaprolactone fumarate polymer. The use of an alkane diol, such as 1,2-propanediol, provides a linear polycaprolactone diol precursor. The use of an alkane triol, such as glycerol, provides a branched polycaprolactone triol precursor. The biocompatible polycaprolactone fumarate formulation releases no diethylene glycol or other undesirable byproducts during degradation.

Claims

1. A polymer having the Formula (I)

H-A₁-B-A₂-C-A₁-B-A₂-H 

 

(I)

wherein

A₁ is

5. The polymer of claim 1 wherein the polymer has a number average molecular weight in the range of 5,000 to 15,000 g mol⁻

1.

7. A crosslinkable, biodegradable material comprising:

the polymer of claim 1; and

a free radical initiator.

8. The material of claim 7 wherein:

the material does not include a crosslinking agent.

9. A scaffold for tissue regeneration, the scaffold comprising:

a biodegradable matrix comprising the polymer of claim 1.

10. The scaffold of claim 9 wherein:

diethylene glycol is not released during hydrolysis of the scaffold.

25. A scaffold for tissue regeneration, the scaffold comprising:

a blend of the polymer of claim 1 and

a polymer having the Formula (II)

26. The scaffold of claim 25 wherein:

the polymer of claim 1 comprises 20 wt. % to 80 wt % of the scaffold, and

the polymer of Formula (II) comprises 20 wt. % to 80 wt % of the scaffold.

2. (canceled)

3. (canceled)

4. (canceled)

6. (canceled)

11. (canceled)

12. (canceled)

13. A polymer having the Formula (II)

17. The polymer of claim 13 wherein the polymer has a number average molecular weight in the range of 5,000 to 15,000 g mol⁻

1.

19. A crosslinkable, biodegradable material comprising:

the polymer of claim 13; and

a free radical initiator.

20. The material of claim 19 wherein:

the material does not include a crosslinking agent.

21. A scaffold for tissue regeneration, the scaffold comprising:

a biodegradable matrix comprising the polymer of claim 13.

22. The scaffold of claim 21 wherein:

diethylene glycol is not released during hydrolysis of the scaffold.

14. (canceled)

15. (canceled)

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18. (canceled)

23. (canceled)

24. (canceled)

27. (canceled)

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31. (canceled)

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35. (canceled)

36. A polymer prepared by a process comprising:

(a) reacting caprolactone with an alkane polyol to prepare a polycaprolactone precursor; and

(b) reacting the polycaprolactone precursor with fumaric acid or a salt thereof.

37. The polymer of claim 36 wherein:

step (b) comprises reacting the polycaprolactone precursor with fumaryl chloride.

38. The polymer of claim 36 wherein:

the alkane polyol is selected from the group consisting of C₂-C₅ alkane polyols.

44. The polymer of claim 36 wherein:

the polycaprolactone precursor has a number average molecular weight in the range of 1,000 to 5,000 g mol<sup>−

1</sup>.

47. The polymer of claim 36 wherein:

the polymer is prepared by a process involving two separate reactions, wherein the polycaprolactone precursor is isolated.

48. The polymer of claim 36 wherein:

both the polycaprolactone precursor and the polymer are prepared in one reaction vessel without isolation of the polycaprolactone precursor.

39. (canceled)

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46. (canceled)