Polymerization of Multifunctional Azides, and Polymers Therefrom

• US 20110065809A1
• Filed: 09/15/2009
• Published: 03/17/2011
• Est. Priority Date: 09/15/2009
• Status: Abandoned Application

• Current Assignee: Medtronic Incorporated (Medtronic Plc)
• Original Assignee: Medtronic Incorporated (Medtronic Plc)
• Inventors: Luo, Lian Leon, Benz, Michael Eric, Munie, Metasebia T.
• Application Number:
  US12/560,240
• Publication Number:
  US 20110065809A1
• Time in Patent Office: Days
• US Class Current: 514/772.7
• CPC Class Codes: A61K 47/16 containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
• CPC Class Codes: A61K 47/18 Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
• CPC Class Codes: A61K 47/34 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers A61K47/10 takes precedence
• CPC Class Codes: A61K 9/0024 Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue compositions for intravenous administration, normal injectable solutions or dispersions for, e.g. subcutaneous administration A61K9/0019; brain implants A61K9/0085; (coated) prostheses, catheters or stents A61L
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C08L 71/02 Polyalkylene oxides

Abstract

Methods for preparing polymers from multifunctional azides and multifunctional azide-reactants are described in the present disclosure. Exemplary multifunctional azide-reactants include multifunctional alkynes and/or multifunctional α-phosphine esters. In certain embodiments, such polymers can be prepared in vivo. Such polymers can be useful in a wide variety of biomedical applications.

Claims

1. A method of preparing a polymer in a tissue, the method comprising:

introducing at least one multifunctional azide into the tissue;

introducing at least one multifunctional azide-reactant into the tissue; and

allowing the at least one multifunctional azide and the at least one multifunctional azide-reactant to react ex vivo and/or in vivo under conditions effective to form the polymer.

8. The method of claim 1 wherein the at least one multifunctional azide comprises at least one azide of the formula N₃—

R¹—

N₃, wherein R¹ represents an organic group.

9. The method of claim 8 wherein R¹ comprises a polyether.

10. The method of claim 9 wherein the polyether is a poly(ethylene glycol).

11. The method of claim 10 wherein the at least one azide is a diazide of the formula (Formula I):

12. The method of claim 1 wherein the at least one multifunctional azide-reactant comprises at least one multifunctional alkyne.

19. The method of claim 12 wherein the at least one multifunctional alkyne comprises a multifunctional terminal alkyne.

22. The method of claim 19 wherein the multifunctional terminal alkyne is an alkyne of the formula N—

(R²—

C≡

CH)₃, wherein each R² independently represents an organic group.

23. The method of claim 22 wherein each R² independently represents an organic moiety.

24. The method of claim 23 wherein the multifunctional terminal alkyne is a trialkyne of the formula (Formula II):

2-7. -7. (canceled)

13-18. -18. (canceled)

20. (canceled)

21. (canceled)

25-54. -54. (canceled)

55. A medical device comprising at least one polymer comprising at least two repeat units of the formula (Formula III):

56. The medical device of claim 55 wherein the at least one polymer is not a hydrogel.

57. The medical device of claim 55 wherein the at least one polymer is substantially biostable.

58. The medical device of claim 55 wherein the at least one polymer is biodegradable.

59. The medical device of claim 58 wherein the at least one polymer does not comprise ester groups.

60. The medical device of claim 55 wherein the at least one polymer is a copolymer.

61. The medical device of claim 55 wherein the device further comprises at least one biologically active agent.

62. The medical device of claim 61 wherein the at least one biologically active agent is at least partially disposed in the at least one polymer.

63. A composition comprising:

at least one biologically active agent; and

at least one polytriazole comprising at least two repeat units of the formula (Formula III);

64. The composition of claim 63 wherein the composition is a pharmaceutical composition.

65-108. -108. (canceled)