IP Library Granted Patent US 11,116,855
Granted Patent B2
US 11,116,855 · App. 16/381,628 · Granted Sep 14, 2021

Radiopaque monomers, polymers, microspheres, and methods related thereto

Inventor: Philippe Reb (Themericourt, FR)
Assignee: Biosphere Medical, Inc.
A61K49/1818A61K9/0019A61K9/1635A61K31/704A61K47/02A61K49/048A61K49/0438A61K49/0442A61K49/126A61K49/1854C07C231/08C08F220/58C08F222/385
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Quick Facts
Patent No.
US 11,116,855
App. No.
16/381,628
Granted
Sep 14, 2021
Kind
B2
Abstract

Radiopaque monomers, polymers, and microspheres are disclosed herein. Methods of using the radiopaque monomers, polymers, and microspheres are disclosed herein. Methods of manufacturing radiopaque monomers, polymers, and microspheres are disclosed herein.

Claims (29)

1. A method of manufacturing a microsphere, comprising:

obtaining a solution comprising one or more monomers, wherein the one or more monomers comprises a first monomer having a structure according to Formula Ib:

polymerizing the one or more monomers to form a polymer; and

isolating a microsphere comprising the polymer, wherein the microsphere comprises a diameter of between about 10 microns and about 2000 microns, and wherein the microsphere is non-resorbable within a body of a patient such that a location of the microsphere can be detected more than about 48 hours after injection into the body of the patient.

2. The method of claim 1 , wherein the solution further comprises a second monomer selected from an acrylamide, an acrylic, an acrylate, or a methacrylate monomer.

3. The method of claim 1 , wherein the solution further comprises an acrylamide monomer.

4. The method of claim 3 , wherein the solution comprises at least one of N-[Tris(hydroxymethyl)methyl]acrylamide or N,N′-Methylenebis(acrylamide).

5. The method of claim 1 , further comprising:

cross-linking the polymer.

6. The method of claim 1 , wherein the microsphere further comprises a magnetic agent.

7. The method of claim 1 , wherein the microsphere further comprise a therapeutic agent.

8. The method of claim 1 , wherein the microsphere is non-resorbable within the body of the patient such that the location of the microsphere can be detected more than about a week after injection into the body of the patient.

9. A method of manufacturing a microsphere, comprising:

obtaining a monomer solution, wherein the monomer solution comprises:

a first monomer having a structure according to Formula Ib:

a second monomer selected from at least one of an acrylamide, an acrylic, an acrylate, or a methacrylate monomer;

polymerizing at least the first monomer and the second monomer to form a polymer, wherein a vinyl moiety of the monomer of Formula Ib is incorporated into a backbone of the polymer; and

isolating a microsphere comprising the polymer, wherein the microsphere comprises a diameter of between about 10 microns and about 2000 microns, and wherein the microsphere is non-resorbable within a body of a patient such that a location of the microsphere can be detected more than about 48 hours after injection into the body of the patient.

10. The method of claim 9 , wherein the second monomer comprises an acrylamide monomer.

11. The method of claim 10 , wherein the second monomer comprises at least one of N-[Tris(hydroxymethyl)methyl]acrylamide or N,N′-Methylenebis(acrylamide).

12. The method of claim 9 , wherein the microsphere further comprise a therapeutic agent.

13. The method of claim 9 , wherein the microsphere is non-resorbable within the body of the patient such that the location of the microsphere can be detected more than about a week after injection into the body of the patient.

14. A method of manufacturing a microsphere, comprising:

obtaining a monomer solution, wherein the monomer solution comprises:

a first monomer having a structure according to Formula Ib:

 and

an acrylamide monomer;

polymerizing at least the first monomer and the acrylamide monomer to form a polymer, wherein a vinyl moiety of the monomer of Formula Ib is incorporated into a backbone of the polymer; and

isolating a microsphere comprising the polymer, wherein the microsphere comprises a diameter of between about 10 microns and about 2000 microns, and wherein the microsphere is non-resorbable within a body of a patient such that a location of the microsphere can be detected more than about 48 hours after injection into the body of the patient.

Assignments (2)
SECURITY INTEREST Recorded Jan 5, 2021
From: BIOSPHERE MEDICAL, INC.
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 054814/0229 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 11, 2019
From: REB, PHILIPPE
To: BIOSPHERE MEDICAL, INC.
Reel/Frame 048862/0172 →
Continuity (3)
Continuation 14992580 · Jan 11, 2016
Provisional Application 62102384 · Jan 12, 2015
Related Publication 20190231908A1 · Aug 1, 2019