End-capped polymers and compositions containing such compounds

• US 20030175322A1
• Filed: 12/20/2002
• Published: 09/18/2003
• Est. Priority Date: 12/21/2001
• Status: Active Grant

• Current Assignee: Isotis Orthobiologics, Inc. (Orthofix Medical Inc.)
• Original Assignee: Isotis Orthobiologics, Inc. (Orthofix Medical Inc.)
• Inventors: Kay, John F., Eisch, John J.
• Granted Patent: US 7,241,813 B2
• Time in Patent Office: Days
• US Class Current: 424/423
• CPC Class Codes: C08G 2650/04 End-capping
• CPC Class Codes: C08G 2650/58 Ethylene oxide or propylene oxide copolymers, e.g. pluronics
• CPC Class Codes: C08G 65/32 Polymers modified by chemical after-treatment
• CPC Class Codes: C08G 65/322 containing hydrogen
• CPC Class Codes: C08G 65/323 containing halogens
• CPC Class Codes: C08G 65/328 containing other elements
• CPC Class Codes: C08G 65/337 containing other elements organic compounds containing halogens only as halides of a carboxyl group C08G65/332

Abstract

End-capped polymers, methods for making those end-capped polymers and compositions containing those end-capped polymers are disclosed. One of the disclosed end-capped copolymers has the formula:

and may be combined with demineralized bone particles to form a tissue repair composition.

Claims

1. A compound having the formula:

2. The compound of claim 1, wherein a is about 101 and b is about 56.

3. A method of making a compound having the formula

4. The method of claim 3, wherein a is about 101 and b is about 56.

5. The method of claim 5, wherein the hydrogens of the hydroxyl end groups are replaced by methyl groups by (i) contacting the compound defined in step (a) with butyllithium or lithium aluminum hydride and (ii) contacting the product of step (i) with methyl iodide.

6. The method of claim 5, wherein essentially all of the compound provided in step (a) is converted to a polymer of the formula:

7. The method of claim 6, wherein a is about 101 and b is about 56.

8. A composition comprising:

(i) demineralized bone particles, and

(ii) a compound of the formula

9. The composition according to claim 8, wherein the compound defined in part (ii) is dispersed in water.

10. The composition according to claim 9, wherein the dispersion of the compound defined in part (ii) in water exhibits reverse phase behavior.

11. The composition according to claim 8, wherein the composition is a tissue repair composition.

12. The composition according to claim 8, wherein the composition further comprises collagen, gelatin, BMPs, bone mineral, hydroxyapatite, tricalcium phosphate, biphasic calcium phosphate, calcium sulfate, biological glasses, a natural polymer or a synthetic polymers.

13. A method of making an end-capped polymer comprising

(i) providing a compound of the formula

(ii) replacing one or both of the hydrogens of the hydroxyl end groups with a hydrocarbon group.

14. The method of claim 13, wherein the hydrocarbon group is a methyl group.

16. The method of claim 13, wherein the hydrogens of both hydroxyl end groups are replaced with hydrocarbon groups.