Polymeric treatment compositions

Patent metadata

Field	Value
Publication number	US-10828388-B2
Application number	US-201916287797-A
Country	US
Kind code	B2
Filing date	Feb 27, 2019
Priority date	Oct 15, 2012
Publication date	Nov 10, 2020
Grant date	Nov 10, 2020

Abstract

Polymeric compositions are described comprising a biocompatible polymer including a biodegradable linkage to a visualization agent and a non-physiological solution; wherein the biocompatible polymer is soluble in the non-physiological solution and insoluble in a physiological solution. Methods of forming the solutions and polymers are disclosed as well as methods of therapeutic use.

First claim

We claim:

1. An embolic system including:
a container including a formulation comprising a substantially stable polymer dissolved in a non-physiological solution,
wherein the polymer includes a biodegradable linkage to a visualization agent wherein the visualization agent is formed from a monomer having at least one aromatic ring and at least one polymerizable moiety, and wherein the polymer is insoluble in a physiological solution.

2. The embolic system of claim 1 , wherein the container is a vial or a syringe.

3. The embolic system of claim 1 , wherein the biodegradable linkage is Seq. ID 1, Seq. ID 2, Seq. ID 3, Seq. ID 4, Seq. ID 5, Seq. ID 6, Seq. ID 7, Seq. ID 8, Seq. ID 9, Seq. ID 10, Seq. ID 11, Seq. ID 12, Seq. ID 13, an ester, a polyester, or a combination thereof.

4. The embolic system of claim 1 , wherein the monomer having at least one aromatic ring and at least one polymerizable moiety is 2-oxo-2-(1-oxo-1-(1-oxo-1-(2,4,6-triiodophenoxy)propan-2-yloxy)propan-2-y- loxy)ethoxy)ethyl acrylate.

5. The embolic system of claim 1 further comprising a second monomer including at least one hydroxyl group.

6. The embolic system of claim 5 , wherein the monomer is an acrylate.

7. The embolic system of claim 6 , wherein the acrylate is hydroxyethyl methacrylate.

8. The embolic system of claim 1 , wherein the non-physiological solution is a water miscible solvent, dimethyl formamide or dimethyl sulfoxide.

9. The embolic system of claim 1 including a reaction product of between about 75% and about 98% 2-oxo-2-(1-oxo-1-(1-oxo-1-(2,4,6-triiodophenoxy)propan-2-yloxy)propan-2-y- loxy)ethoxy)ethyl acrylate, between about 2% and about 25% hydroxyethyl methacrylate, and less than 1% azobisisobutyronitrile.

10. The embolic system of claim 1 including a reaction product of between about 85% and about 98% 1-((2-(methacryloyloxy)ethoxy)carbonyloxy) ethyl 3,5-diacetamido-2,4,6-triiodobenzoate, between about 2% and about 15% hydroxyethyl methacrylate, and less than 1% azobisisobutyronitrile.

11. The embolic system of claim 1 , wherein substantially stable is where the polymer is greater than 90% intact after about 1 month after an implantation procedure, where the polymer is greater than 60% intact after about 1 year after the implantation procedure, where the polymer is greater than 60% intact after about 5 years after the implantation procedure, where the polymer is greater than 90% intact after about 2 months after the implantation procedure, or where the polymer is greater than 80% intact after about 6 months after the implantation procedure.

12. An embolic system including:
a container including a formulation,
wherein the formulation includes a substantially stable biocompatible polymer comprising a reaction product of:
a first monomer including a polymerizable moiety having a biodegradable linkage to a visualization agent having at least one aromatic ring, wherein the at least one aromatic ring includes a plurality of iodine atoms, and a second monomer including a polymerizable moiety and at least one hydroxyl group; and
a non-physiological solution;

wherein the substantially stable biocompatible polymer is soluble in the non-physiological solution and insoluble in a physiological solution.

13. The embolic system of claim 12 , wherein the container is a vial or a syringe.

14. The embolic system of claim 12 , wherein the biodegradable linkage is Seq. ID 1, Seq. ID 2, Seq. ID 3, Seq. ID 4, Seq. ID 5, Seq. ID 6, Seq. ID 7, Seq. ID 8, Seq. ID 9, Seq. ID 10, Seq. ID 11, Seq. ID 12, Seq. ID 13, an ester, a polyester, ora combination thereof.

15. The embolic system of claim 12 , wherein the first monomer including a polymerizable moiety having a biodegradable linkage to a visualization agent having at least one aromatic ring is 2-oxo-2-(1-oxo-1-(1-oxo-1-(2,4,6-triiodophenoxy)propan-2-yloxy)propan-2-y- loxy)ethoxy)ethyl acrylate.

16. The embolic system of claim 12 , wherein the non-physiological solution is a water miscible solvent, dimethyl formamide or dimethyl sulfoxide.

17. The embolic system of claim 12 , wherein the non-physiological solution has a pH of less than 5 or greater than 8.

18. The embolic system of claim 12 , wherein the substantially stable biocompatible polymer has a concentration of about 1% w/w to about 50% w/w.

19. The embolic system of claim 12 , wherein the reaction product is of between about 75% and about 98% 2-oxo-2-(1-oxo-1-(1-oxo-1-(2,4,6-triiodophenoxy)propan-2-yloxy)propan-2-y- loxy)ethoxy)ethyl acrylate, between about 2% and about 25% hydroxyethyl methacrylate, and less than 1% azobisisobutyronitrile.

20. The embolic system of claim 12 , wherein the reaction product is of between about 85% and about 98% 1-((2-(methacryloyloxy)ethoxy)carbonyloxy)ethyl 3,5-diacetamido-2,4,6-triiodobenzoate, between about 2% and about 15% hydroxyethyl methacrylate, and less than 1% azobisisobutyronitrile.

Assignees

• Microvention Inc

Inventors

• Cruise Gregory M
• Constant Michael J
• Keeley Edward Michael
• Greene Rob
• Harris Clayton

Classifications

• A61K49/12

  Macromolecular compounds · CPC title

• A61L24/0015

  Medicaments; Biocides · CPC title

• A61L24/06 Primary

  obtained by reactions only involving carbon-to-carbon unsaturated bonds {(A61L24/043, A61L24/046 take precedence)} · CPC title

• A61L24/001

  Use of materials characterised by their function or physical properties · CPC title

• A61L2300/44

  Radioisotopes, radionuclides · CPC title