Radiopaque polymers

Patent metadata

Field	Value
Publication number	US-11957755-B2
Application number	US-202117329891-A
Country	US
Kind code	B2
Filing date	May 25, 2021
Priority date	Sep 6, 2013
Publication date	Apr 16, 2024
Grant date	Apr 16, 2024

Abstract

Radiopaque hydrogels, in particular radiopaque hydrogel microspheres, comprising a polymer having 1,2-dil or 1,3-diol groups acetalized with radiopaque species.

First claim

The invention claimed is:

1. A method of treatment in which a hydrogel is administered into a blood vessel of a patient to embolize said blood vessel, the hydrogel being in the form of microspheres comprising a cross-linked polymer network that comprises polyvinyl alcohol (PVA) or a copolymer of PVA and a radiopaque species comprising one or more covalently bound iodines that are coupled to the PVA or copolymer of PVA through a cyclic acetal group and that provides the microspheres with greater than 15 mg of iodine per ml of microspheres fully hydrated in normal saline as a packed volume wherein the radiopaque species comprises an iodinated aromatic group.

2. The method of claim 1 , wherein the blood vessel is associated with a solid tumor.

3. The method of claim 2 , wherein the solid tumor is hepatocellular carcinoma.

4. A method of treatment in which a composition is administered into a blood vessel of a patient to embolize said blood vessel, the composition comprising (a) hydrogel in the form of microspheres comprising a cross-linked polymer network that comprises polyvinyl alcohol (PVA) or a copolymer of PVA and a radiopaque species comprising one or more covalently bound iodines that are coupled to the PVA or copolymer of PVA through a cyclic acetal group and that provides the microspheres with greater than 15 mg of iodine per ml of microspheres fully hydrated in normal saline as a packed volume and (b) a therapeutic agent, wherein the therapeutic agent is absorbed into the microspheres wherein the radiopaque species comprises an iodinated aromatic group.

5. The method of claim 4 , wherein the blood vessel is associated with a solid tumor.

6. The method of claim 1 , wherein the radiopaque species provides the microspheres with greater than 50 mg of iodine per ml of microspheres fully hydrated in normal saline as a packed volume.

7. The method of claim 1 , wherein the radiopaque species provides the microspheres with greater than 100 mg of iodine per ml of microspheres fully hydrated in normal saline as a packed volume.

8. The method of claim 1 , wherein the hydrogel has a net charge at physiological pH.

9. The method of claim 1 , wherein the radiopaque species comprises an iodinated phenyl group.

10. The method of claim 1 , wherein the microspheres have a mean diameter size range of from 10 to 2000 m.

11. The method of claim 1 , wherein the microspheres have a mean radiopacity of 500HU or greater.

12. The method of claim 4 , wherein the microspheres have a mean diameter size range of from 10 to 2000 μm.

13. The method of claim 4 , wherein the microspheres have a mean radiopacity of 500HU or greater.

14. The method of claim 4 , wherein the hydrogel has a net charge at physiological pH.

15. The method of claim 14 , wherein the therapeutic agent is electrostatically held in the hydrogel and elutes from the hydrogel in electrolytic media.

16. The method of claim 4 , wherein the radiopaque species provides the microspheres with greater than 50 mg of iodine per ml of microspheres fully hydrated in normal saline as a packed volume.

17. The method of claim 4 , wherein the radiopaque species provides the microspheres with greater than 100 mg of iodine per ml of microspheres fully hydrated in normal saline as a packed volume.

18. A method of treatment in which a hydrogel is administered into a blood vessel of a patient to embolize said blood vessel, the hydrogel having a net charge at physiological pH in the form of microspheres having a mean diameter size range of from 10 to 2000 m and comprising a cross-linked polymer network that comprises polyvinyl alcohol (PVA) or a copolymer of PVA and a radiopaque species comprising an iodinated aromatic group that is coupled to the PVA or copolymer of PVA through a cyclic acetal group and that provides the microspheres with greater than 50 mg of iodine per ml of microspheres fully hydrated in normal saline as a packed volume.

Assignees

• Boston Scientific Medical Device Limited

Inventors

• Hohn Stephane
• Lewis Andrew Lennard
• Willis Sean Leo
• Dreher Matthew R
• Ashrafi Koorosh
• Tang Yiqing

Classifications

• A61K47/34 Primary

  Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence) · CPC title

• A61K9/0024

  Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue (compositions for intravenous administration, normal injectable solutions or dispersions for, e.g. subcutaneous administration A61K9/0019; brain implants A61K9/0085; (coated) prostheses, catheters or stents A61L) · CPC title

• A61K31/404

  Indoles, e.g. pindolol · CPC title

• A61K31/41

  having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole · CPC title

• A61K31/44

  Non condensed pyridines; Hydrogenated derivatives thereof · CPC title