Particles

• US 9,907,880 B2
• Filed: 03/25/2016
• Issued: 03/06/2018
• Est. Priority Date: 03/26/2015
• Status: Active Grant

• Current Assignee: Microvention Incorporated (Terumo Corporation)
• Original Assignee: Microvention Incorporated (Terumo Corporation)
• Inventors: Cruise, Gregory M., Plotkin, Steve, Wu, Xinping
• Primary Examiner(s): HARLAN, ROBERT D
• Application Number:
  US15/081,648
• Publication Number:
  US 20160279282A1
• Time in Patent Office: 711 Days
• CPC Class Codes: A61L 24/001 Use of materials characterised by their function or physical properties
• CPC Class Codes: A61L 24/06 obtained by reactions only involving carbon-to-carbon unsaturated bonds A61L24/043, A61L24/046 take precedence
• CPC Class Codes: A61L 2430/36 for embolization or occlusion, e.g. vaso-occlusive compositions or devices artificial blood vessels A61L27/507
• CPC Class Codes: C08F 222/385 Monomers containing two or more (meth)acrylamide groups, e.g. N,N'-methylenebisacrylamide
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 33/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C08L 33/26 Homopolymers or copolymers of acrylamide or methacrylamide

Abstract

Embolic particles are described comprising a treated polymer particle. The particles are reaction products of a prepolymer solution including at least one polyether macromer and an appropriate monomer. The treated polymer particles can have a first diameter that is smaller than a second diameter, wherein the second diameter is achieved when the treated polymer particle is subjected to a physiological condition. Methods of making and using these polymer particles are also described.

Claims

1. An embolic composition comprising:

embolic particles including a reaction product of a prepolymer solution including at least one macromer and at least one monomer,

wherein the at least one macromer is poly(ethylene glycol) diacrylamide, poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, poly(ethylene glycol) dimethacrylamide, or a combination thereof,

wherein the embolic particles include acidic groups that are treated with an acidic solution to form treated embolic particles,

wherein the treated embolic particles have a first diameter and a second diameter, and wherein the second diameter is larger than the first diameter when the treated polymer particle is subjected to a physiological condition, and

wherein the embolic particles are substantially spherical, and

wherein the first diameter is between about 50 μ

m and about 1,500 μ

m.

2. The embolic composition of claim 1, wherein the first diameter is between about 400 μ

m and about 1,500 μ

m.

3. The embolic composition of claim 2, wherein the first diameter is smaller than a diameter of a microcatheter.

4. The embolic composition of claim 1, wherein the second diameter is between about 80 μ

m and about 3,600 μ

m.

5. The embolic composition of claim 4, wherein the second diameter is larger than a diameter of a microcatheter.

6. The embolic composition of claim 1, wherein the at least one monomer includes ionic groups.

7. The embolic composition of claim 6, wherein the monomer containing ionic groups is sodium acrylate.

8. The embolic composition of claim 6, wherein the prepolymer solution further includes a biodegradable crosslinker having a structure:

9. The embolic composition of claim 1, wherein the embolic particles further include a visualization agent having a structure:

10. The embolic composition of claim 1, wherein the physiological condition is physiological pH.

11. A method of making polymer particles comprising:

treating polymer particles formed by reacting a prepolymer solution including at least one macromer, an acrylic monomer, and an initiator in non-solvent to form treated polymer particles;

wherein the treated polymer particle has a first diameter and a second diameter, wherein the second diameter is larger than the first diameter when the treated polymer particle is subjected to a physiological condition,

wherein the at least one macromer is poly(ethylene glycol) diacrylamide, poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, poly(ethylene glycol) dimethacrylamide, or a combination thereof,

wherein the embolic particles are substantially spherical, and

wherein the first diameter is between about 50 μ

m and about 1,500 μ

m.

12. The method of claim 11, wherein the non-solvent is a mineral oil, hexane, or water.

13. The method of claim 11, wherein the initiator is ammonium persulfate, tetramethylethylene diamine, or a combination thereof.

14. The method of claim 11, wherein the first diameter is smaller than the diameter of a microcatheter.

15. The method of claim 11, wherein the second diameter is between about 80 μ

m and about 3,600 μ

m.

16. The method of claim 15, wherein the second diameter is larger than the diameter of the microcatheter.

17. The method of claim 11, wherein the treating is acid treating and the monomer containing ionic groups is sodium acrylate or the treating is base treating and the monomer containing ionic groups includes amino groups.