Polymer particles

• US 10,118,980 B1
• Filed: 05/24/2017
• Issued: 11/06/2018
• Est. Priority Date: 11/08/2013
• Status: Active Grant

• Current Assignee: Terumo Corporation
• Original Assignee: Terumo Corporation
• Inventors: Plotkin, Steve, Cruise, Gregory M., Keeley, Edward Michael, Yu, Renee, Harris, Clayton
• Primary Examiner(s): Kiliman, Leszek B
• Application Number:
  US15/604,529
• Publication Number:
  US 20180298133A1
• Time in Patent Office: 531 Days
• Field of Search: 428402
• CPC Class Codes: A61K 31/704 attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin digitoxin A61K31/7048
• CPC Class Codes: A61K 47/32 Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers , poly(meth)acrylates, or polyvinyl pyrrolidone
• CPC Class Codes: A61K 9/0019 Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner non-active ingredients are additionally classified in A61K47/00
• CPC Class Codes: A61K 9/146 with organic macromolecular compounds
• CPC Class Codes: A61K 9/5026 obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
• CPC Class Codes: A61L 2300/418 Agents promoting blood coagulation, blood-clotting agents, embolising agents
• CPC Class Codes: A61L 24/0015 Medicaments; Biocides
• 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: C08F 16/06 Polyvinyl alcohol ; Vinyl alcohol
• CPC Class Codes: C08F 20/28 containing no aromatic rings in the alcohol moiety
• CPC Class Codes: C08F 20/38 Esters containing sulfur
• CPC Class Codes: C08F 20/56 Acrylamide; Methacrylamide
• CPC Class Codes: C08F 22/385 Monomers containing two or more (meth)acrylamide groups, e.g. N,N'-methylenebisacrylamide
• CPC Class Codes: C08F 220/10 Esters
• CPC Class Codes: C08F 220/20 of polyhydric alcohols or phenols , e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
• CPC Class Codes: C08F 220/28 containing no aromatic rings in the alcohol moiety
• CPC Class Codes: C08F 220/282 and containing two or more oxygen atoms
• CPC Class Codes: C08F 220/38 Esters containing sulfur
• CPC Class Codes: C08F 220/382 and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate
• CPC Class Codes: C08F 290/062 Polyethers
• CPC Class Codes: C08G 65/33324 : acyclic
• CPC Class Codes: Y10T 428/2982 : Particulate matter [e.g., sphere, flake, etc.]

Abstract

Polymer particle embolics and methods of making same are described. The particle embolics can be used as embolization agents.

Claims

1. A polymer particle comprising:

at least one derivatized poly(ethylene glycol) macromer, poly(propylene glycol) macromer, poly(tetramethylene oxide) macromer, or a combination thereof at a concentration of between about 15% w/w and about 50% w/w; and

at least one monomer including glycerol monomethacrylate, amino ethyl methacrylate, 3-sulfopropyl acrylate, amino propyl methacrylamide, or a combination thereof, wherein the monomer is not n-isopropyl acrylamide,

wherein the polymer particle is spherical and has a diameter less than about 1,200 μ

m.

2. The polymer particle of claim 1, wherein the polymer particle has a diameter between about 40 μ

m and about 1,200 μ

m.

3. The polymer particle of claim 1, further comprising at least one additional monomer that is not n-isopropyl acrylamide.

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

5. The polymer particle of claim 1, wherein the at least one monomer is glycerol monomethacrylate at a concentration of about 68% w/w.

6. The polymer particle of claim 1, wherein the at least one monomer is 3-sulfopropyl acrylate at a concentration of about 59% w/w.

7. The polymer particle of claim 1, wherein the at least one monomer is amino propyl methacrylamide at a concentration of about 1% w/w.

8. The polymer particle of claim 1, wherein the at least one monomer is amino ethyl methacrylate at a concentration of about 3% w/w.

9. The polymer particle of claim 1, wherein the at least one derivatized poly(ethylene glycol) macromer is poly(ethylene glycol) diacrylamide, poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, poly(ethylene glycol) dimethacrylamide, or a combination thereof.

10. The polymer particle of claim 1, wherein the at least one derivatized poly(ethylene glycol) macromer is poly(ethylene glycol) diacrylamide 10,000.

11. A polymer particle comprising:

at least one derivatized poly(ethylene glycol) macromer, poly(propylene glycol) macromer, poly(tetramethylene oxide) macromer, or a combination thereof at a concentration of between about 15% w/w and about 50% w/w, wherein the at least one derivatized poly(ethylene glycol) macromer is poly(ethylene glycol) diacrylamide, poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, poly(ethylene glycol) dimethacrylamide, or a combination thereof; and

at least one monomer that is not n-isopropyl acrylamide,

wherein the polymer particle is spherical and has a diameter less than about 1,200 μ

m.

12. The polymer particle of claim 11, wherein the polymer particle has a diameter between about 40 μ

m and about 1,200 μ

m.

13. The polymer particle of claim 11, further comprising at least one additional monomer that is not n-isopropyl acrylamide.

14. The polymer particle of claim 11, wherein the at least one monomer includes a functional group, wherein the functional group is acrylate, acrylamide, methacrylate, or methacrylamide.

15. The polymer particle of claim 11, wherein the at least one monomer is glycerol monomethacrylate, amino ethyl methacrylate, 3-sulfopropyl acrylate, amino propyl methacrylamide, or a combination thereof.

16. The polymer particle of claim 15, wherein the at least one monomer is glycerol monomethacrylate at a concentration of about 68% w/w.

17. The polymer particle of claim 15, wherein the at least one monomer is 3-sulfopropyl acrylate at a concentration of about 59% w/w.

18. The polymer particle of claim 16, wherein the at east one monomer is amino propyl methacrylamide at a concentration of about 1% w/w.

19. The polymer particle of claim 15, wherein the at least one monomer is amino ethyl methacrylate at a concentration of about 3% w/w.

20. The polymer particle of claim 11, wherein the at least one derivatized poly(ethylene glycol) macromer is poly(ethylene glycol) diacrylamide 10,000.