Biocompatible polycaprolactone fumarate formulations

• US 10,426,867 B2
• Filed: 04/04/2012
• Issued: 10/01/2019
• 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.
• Primary Examiner(s): Falkowitz, Anna R
• Application Number:
  US14/009,987
• Publication Number:
  US 20140099278A1
• Time in Patent Office: 2,736 Days
• 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 scaffold for tissue regeneration, the scaffold comprising:

a blend of a polymer having the Formula (I)

H-A₁-B-A₂-C-A₁-B-A₂-H 

 

(I)

wherein

A₁ is

2. The scaffold of claim 1 wherein:

the polymer of Formula (I) comprises 40 wt. % to 60 wt % of the scaffold, and

the polymer of Formula (II) comprises 40 wt. % to 60 wt % of the scaffold.

3. The scaffold of claim 1 wherein:

in the polymer of Formula (I), X is methylethylene.

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

1.

5. The scaffold of claim 1 wherein:

in the polymer of Formula (II), X is propanetriyl.

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

1.

7. The scaffold of claim 1 wherein:

the scaffold maintains its geometrical structure and dimensions throughout an autoclave sterilization process, and

the scaffold maintains mechanical properties within an order of magnitude during the autoclave sterilization process.

8. The scaffold of claim 1 wherein:

diethylene glycol is not released during hydrolysis of the scaffold.

9. The scaffold of claim 1 wherein:

the scaffold has a fracture stress in a range of 2 to 8 MPa.

10. The scaffold of claim 1 wherein:

the scaffold has a tensile modulus in a range of 20 to 80 MPa.