Polymeric treatment compositions

• US 9,655,989 B2
• Filed: 06/10/2015
• Issued: 05/23/2017
• Est. Priority Date: 10/15/2012
• Status: Active Grant

• Current Assignee: Microvention Incorporated (Terumo Corporation)
• Original Assignee: Microvention Incorporated (Terumo Corporation)
• Inventors: Cruise, Gregory M., Constant, Michael J., Keeley, Edward Michael, Greene, Rob, Harris, Clayton
• Primary Examiner(s): Yoon, Tae H
• Application Number:
  US14/736,145
• Publication Number:
  US 20160243273A1
• Time in Patent Office: 713 Days
• Field of Search: 523117, 523105, 528182
• CPC Class Codes: A61K 49/0442 Polymeric X-ray contrast-enhancing agent comprising a halogenated group
• CPC Class Codes: A61K 49/12 Macromolecular compounds
• CPC Class Codes: A61L 2300/44 Radioisotopes, radionuclides
• CPC Class Codes: A61L 24/001 Use of materials characterised by their function or physical properties
• 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: A61L 2400/06 Flowable or injectable implant compositions
• CPC Class Codes: A61L 2430/36 for embolization or occlusion, e.g. vaso-occlusive compositions or devices
• CPC Class Codes: A61P 7/04 Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
• CPC Class Codes: A61P 9/00 Drugs for disorders of the cardiovascular system
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 33/26 Homopolymers or copolymers of acrylamide or methacrylamide

Abstract

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

Claims

1. A polymer including:

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,

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

wherein substantially stable is where the polymer is greater than 90% intact after about 1 month after an implantation procedure.

2. The polymer 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, or Seq. ID 13.

3. The polymer of claim 1, wherein the biodegradable linkage is an ester or a polyester.

4. The polymer of claim 1, wherein a monomer included in the polymer is 2-oxo-2-(1-oxo-1-(1-oxo-1-(2,4,6-triiodophenoxy)propan-2-yloxy)propan-2-yloxy)ethoxy)ethyl acrylate.

5. The polymer of claim 1 including a monomer including at least one hydroxyl group.

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

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

8. The polymer of claim 1, wherein the non-physiological solution is dimethyl formamide.

9. The polymer of claim 1, wherein the non-physiological solution is dimethyl sulfoxide.

10. The polymer 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-yloxy)ethoxy)ethyl acrylate, between about 2% and about 25% hydroxyethyl methacrylate, and less than 1% azobisisobutyronitrile.

11. The polymer 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.

12. The polymer of claim 1, wherein substantially stable is where the polymer is greater than 60% intact after about 1 year after the implantation procedure.

13. The polymer of claim 1, wherein substantially stable is where the polymer is greater than 60% intact after about 5 years after the implantation procedure.

14. The polymer of claim 1, wherein substantially stable is where the polymer is greater than 90% intact after about 2 months after the implantation procedure.

15. The polymer of claim 1, wherein substantially stable is where the polymer is greater than 80% intact after about 6 months after the implantation procedure.