Polymer particles

Patent metadata

Field	Value
Publication number	US-9803043-B2
Application number	US-201615369213-A
Country	US
Kind code	B2
Filing date	Dec 5, 2016
Priority date	Sep 19, 2013
Publication date	Oct 31, 2017
Grant date	Oct 31, 2017

Abstract

Biodegradable, cross-linked polymer particle embolics and methods of making the same are described. The particle embolics can be used as embolization agents.

First claim

We claim:

1. A polymer particle comprising:
at least one monomer including at least one functional group; and

at least one crosslinker;
wherein the polymer particle has a spherical diameter between about 40 μm and about 1,200 μm and is susceptible to degradation through hydrolysis or enzymatic action, and wherein the degradation provides less than about 10% of the polymer particle intact after about 5 days.

2. The polymer particle of claim 1 , wherein the polymer particle has a spherical diameter between about 75 μm and about 1,200 μm.

3. The polymer particle of claim 1 , wherein the at least one functional group is acrylate, acrylamide, methacrylate, or methacrylamide.

4. The polymer particle of claim 1 , wherein the at least one monomer includes an ionizable functional group.

5. The polymer particle of claim 4 , wherein the ionizable functional group is basic or acidic.

6. The polymer particle of claim 1 , wherein the at least one crosslinker includes at least two functional groups.

7. The polymer particle of claim 1 , wherein the crosslinker includes at least one linkage susceptible to degradation through hydrolysis or enzymatic action.

8. The polymer particle of claim 7 , wherein the crosslinker is bis-glycidyl amino alcohol,

wherein a, b, c, d, e, and f are each independently 1-20.

9. The polymer particle of claim 7 , wherein the at least one linkage is an ester, a thioester, a carbonate, a peptide cleavable by matrix metalloproteinases, a peptide cleavable by matrix collagenases, a peptide cleavable by matrix elastases, a peptide cleavable by matrix cathepsins, or a combination thereof.

10. The polymer particle of claim 9 , including a second crosslinker including a second linkage selected from an ester, a thioester, a carbonate, a peptide cleavable by matrix metalloproteinases, a peptide cleavable by matrix collagenases, a peptide cleavable by matrix elastases, and a peptide cleavable by matrix cathepsins.

11. The polymer particle of claim 1 , wherein the at least one monomer is dimethylacrylamide and the at least one crosslinker is bis-glycidyl amino alcohol.

12. The polymer particle of claim 1 , wherein the at least one monomer is acrylamide and the at least one crosslinker is bi-functionalized methacryloyl-Ala-Pro-Gly-Leu-AEE-methacrylate.

13. A method of making a polymer particle comprising:
reacting a prepolymer solution including at least one monomer including at least one functional group, at least one crosslinker susceptible to degradation through hydrolysis or enzymatic action, and an initiator in an oil; and
forming the polymer particle, wherein the polymer particle has a spherical diameter between about 40 μm and about 1,200 μm, and wherein the degradation provides less than about 10% of the polymer particle intact after about 5 days.

14. The method of claim 13 , wherein the oil is mineral oil.

15. The method of claim 13 , wherein the initiator is N,N,N′,N′-tetramethylethylenediamine.

16. The method of claim 13 , wherein the polymer particle has a circularity of at least about 0.90.

17. The method of claim 13 , wherein the at least one crosslinker is bis-glycidyl amino alcohol,

wherein a, b, c, d, e, and f are each independently 1-20.

18. The method of claim 13 , wherein the polymer particle is substantially degraded within about 6 months of implantation.

19. The method of claim 13 , wherein the at least one monomer is acrylamide and the at least one crosslinker is bis-glycidyl amino alcohol.

20. The method of claim 13 , wherein the at least one monomer is acrylamide and the at least one crosslinker is bi-functionalized methacryloyl-Ala-Pro-Gly-Leu-AEE-methacrylate.

Assignees

• Terumo Corp

Inventors

• Cruise Gregory M
• Hincapie Gloria
• Harris Clayton

Classifications

• C08F222/408

  substituted imides comprising other heteroatoms · CPC title

• C08F220/56

  Acrylamide; Methacrylamide · CPC title

• C08L2201/06

  Biodegradable · CPC title

• C08L33/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title

• C08K5/16

  Nitrogen-containing compounds {(C08K5/0091 takes precedence)} · CPC title