Poly(orthoester) polymers, and methods of making and using same

• US 7,875,697 B2
• Filed: 06/29/2007
• Issued: 01/25/2011
• Est. Priority Date: 06/29/2006
• Status: Expired due to Fees

• Current Assignee: Medtronic Incorporated (Medtronic Plc)
• Original Assignee: Medtronic Incorporated (Medtronic Plc)
• Inventors: Alkatout, Julie A., Sparer, Randall V., Benz, Michael Eric
• Primary Examiner(s): Eashoo; Mark
• Assistant Examiner(s): Heincer; Liam J
• Application Number:
  US11/824,504
• Publication Number:
  US 20080033140A1
• Time in Patent Office: 1,306 Days
• Field of Search: 528/392, 528/406
• US Class Current: 528/392
• CPC Class Codes: C08G 63/664 derived from hydroxy carboxylic acids
• CPC Class Codes: C08G 64/183 containing polyether sequences
• CPC Class Codes: C08G 65/34 from hydroxy compounds or their metallic derivatives C08G65/26 takes precedence

Abstract

Poly(orthoester) polymers, and methods of making and using such poly(orthoester) polymers are provided. The poly(orthoester) polymers can be useful for applications including, for example, medical devices and pharmaceutical compositions. In a preferred embodiment, the poly(orthoester) polymers are biodegradable.

Claims

1. A polymer comprising two or more repeat units selected from the group consisting of:

a repeat unit of the formula (Formula VI);

2. The polymer of claim 1 wherein the repeat unit of the formula (Formula VI) is represented by Formula VIa:

3. The polymer of claim 2 wherein each R¹⁹ represents hydrogen and each R⁹ independently represents hydrogen or methyl.

4. The polymer of claim 1 wherein the polymer further comprises repeat units selected from the group consisting of crosslinkable repeat units, crosslinked repeat units, repeat units having imagable groups, repeat units having latent reactive sites, and combinations thereof.

5. The polymer of claim 1 wherein the polymer further comprises repeat units selected from the group consisting of alpha-hydroxy alkanoates, beta-hydroxy alkanoates, gamma-hydroxy alkanoates, delta-hydroxy alkanoates, epsilon-hydroxy alkanoates, gylcols, carbonates, acetals, urethane-containing groups, carbamate-containing groups, and combinations thereof.

6. The polymer of claim 1 wherein the polymer is a copolymer.

7. The polymer of claim 2 wherein the copolymer is selected from the group consisting of random copolymers, alternating copolymers, block copolymers, graft copolymers, and combinations thereof.

8. The polymer of claim 7 wherein the copolymer is a block copolymer, and at least one block of the block copolymer is a poly(orthoester) block comprising the two or more repeat units selected from the group consisting of repeat units of Formula VI, repeat units of Formula VII, and combinations thereof.

9. The polymer of claim 8 wherein at least one other block of the block copolymer is a block comprising repeat units selected from the group consisting of alpha-hydroxy alkanoates, beta-hydroxy alkanoates, gamma-hydroxy alkanoates, delta-hydroxy alkanoates, epsilon-hydroxy alkanoates, carbonates, acetals, urethane-containing groups, carbamate-containing groups, and combinations thereof.

10. The polymer of claim 8 wherein at least one other block of the block copolymer is a polyketal block.

11. The polymer of claim 8 wherein at least one other block of the block copolymer is a poly(alkyleneglycol) block comprising alkylene glycol repeat units.

12. The polymer of claim 1 wherein the polymer is biodegradable.

13. The polymer of claim 1 wherein the polymer is a tissue bulking agent, a tissue replacement agent, a tissue repair agent, a surgical void filler, an agent used to prevent surgical adhesions, or a combination thereof.

14. A polymer comprising two or more repeat units selected from the group consisting of:

a repeat unit of the formula (Formula VI);

15. The polymer of claim 14 wherein the repeat unit of the formula (Formula VI) is represented by Formula VIa:

16. The polymer of claim 15 wherein each R¹⁹ represents hydrogen and each R⁹ independently represents hydrogen or methyl.

17. The polymer of claim 14 wherein the polymer further comprises repeat units selected from the group consisting of crosslinkable repeat units, crosslinked repeat units, repeat units having imagable groups, repeat units having latent reactive sites, and combinations thereof.

18. The polymer of claim 14 wherein the polymer further comprises repeat units selected from the group consisting of alpha-hydroxy alkanoates, beta-hydroxy alkanoates, gamma-hydroxy alkanoates, delta-hydroxy alkanoates, epsilon-hydroxy alkanoates, gylcols, carbonates, acetals, urethane-containing groups, carbamate-containing groups, and combinations thereof.

19. The polymer of claim 14 wherein the polymer is a copolymer.

20. The polymer of claim 19 wherein the copolymer is selected from the group consisting of random copolymers, alternating copolymers, block copolymers, graft copolymers, and combinations thereof.

21. The polymer of claim 20 wherein the copolymer is a block copolymer, and at least one block of the block copolymer is a poly(orthoester) block comprising the two or more repeat units selected from the group consisting of repeat units of Formula VI, repeat units of Formula VII, and combinations thereof.

22. The polymer of claim 21 wherein at least one other block of the block copolymer is a block comprising repeat units selected from the group consisting of alpha-hydroxy alkanoates, beta-hydroxy alkanoates, gamma-hydroxy alkanoates, delta-hydroxy alkanoates, epsilon-hydroxy alkanoates, carbonates, acetals, urethane-containing groups, carbamate-containing groups, and combinations thereof.

23. The polymer of claim 18 wherein at least one other block of the block copolymer is a polyketal block.

24. The polymer of claim 21 wherein at least one other block of the block copolymer is a poly(alkyleneglycol) block comprising alkylene glycol repeat units.

25. The polymer of claim 14 wherein the polymer is biodegradable.

26. The polymer of claim 14 wherein the polymer is a tissue bulking agent, a tissue replacement agent, a tissue repair agent, a surgical void filler, an agent used to prevent surgical adhesions, or a combination thereof.