Radiopaque polymers

Patent metadata

Field	Value
Publication number	US-10350295-B2
Application number	US-201414916477-A
Country	US
Kind code	B2
Filing date	Sep 5, 2014
Priority date	Sep 6, 2013
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

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

First claim

The invention claimed is:

1. A cross linked hydrogel polymer comprising polyvinyl alcohol (PVA) comprising 1,3-diol groups that are acetalised with a radiopaque species, according to the general formula I:

wherein X is a group of the formula:

wherein:
Z is a linking group bonded to the cyclic acetal, or is absent, such that the phenyl group is bonded to the cyclic acetal, if Z is present, then Z is C 1-6 alkylene, C 1-6 alkoxylene or C 1-6 alkoxyalkylene,
Hal is 1,2,3 or 4 covalently attached iodines.

2. A crosslinked hydrogel polymer according to claim 1 wherein the polymer comprises greater than 20% iodine by dry weight.

3. A crosslinked hydrogel polymer according to claim 1 wherein the polymer is in the form of microparticles or microspheres.

4. A crosslinked hydrogel polymer according to claim 3 wherein the polymer is in the form of microspheres with a mean diameter size range of from 10 to 2000μm.

5. A crosslinked hydrogel polymer according to claim 1 wherein the polymer has a net charge at pH 7.4.

6. A composition comprising a crosslinked hydrogel polymer according to claim 1 and a therapeutic agent wherein the therapeutic agent is absorbed into the polymer matrix.

7. A composition according to claim 6 wherein the therapeutic agent is electrostatically held in the hydrogel polymer and elutes from the polymer in electrolytic media.

8. A crosslinked hydrogel polymer according to claim 1 wherein the phenyl group is substituted by 3 or 4 iodines.

9. A crosslinked hydrogel polymer according to claim 1 wherein the polymer comprises greater than 30% iodine by dry weight.

10. A crosslinked hydrogel polymer according to claim 9 wherein the polymer comprises from 30% to 50% iodine by dry weight.

11. A crosslinked hydrogel polymer according to claim 1 wherein Z is a methylene or ethylene group or is a group (CH 2 ) p —O—(CH 2 ) q — wherein q is 0, 1 or 2 and p is 1 or 2 or is absent.

12. A crosslinked hydrogel polymer according to claim 1 wherein, Z is —(CH 2 ) 2 O(CH 2 ) 2 —, —CH 2 OCH 2 —, —(CH 2 ) 2 O—, —CH 2 O— or is absent.

13. A crosslinked hydrogel polymer according to claim 1 wherein Hal is 3 or 4 iodines.

14. A crosslinked hydrogel polymer according to claim 1 wherein Hal is 2,3,5 triiodo, 2,4,6 triiodo or 2,3,4,6 tetraiodo.

15. A crosslinked hydrogel polymer according to claim 1 wherein the polymer comprises greater than 10% iodine by dry weight.

16. A crosslinked hydrogel polymer comprising PVA and comprising 1,3-diol groups of the PVA that are acetalised with a radiopaque species, such that the hydrogel polymer comprises groups according to the general formula I:

wherein X is an iodinated aryl group.

17. A crosslinked hydrogel polymer according to claim 16 wherein X is an iodinated phenyl group.

18. A crosslinked hydrogel polymer comprising PVA and comprising 1,3-diol groups of the PVA that are acetalised with a radiopaque species, such that the hydrogel polymer comprises groups according to any of the general formulas Ia to Ie

19. A crosslinked hydrogel polymer according to claim 1 in which the polymer is a homopolymer of PVA, a copolymer of PVA or a graft polymer of PVA.

20. A crosslinked hydrogel polymer according to claim 16 in which the polymer is a homopolymer of PVA, a copolymer of PVA or a graft polymer of PVA.

21. A crosslinked hydrogel polymer according to claim 18 in which the polymer is a homopolymer of PVA, a copolymer of PVA or a graft polymer of PVA.

Assignees

• Biocompatibles Uk Ltd

Inventors

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

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P9/00

  Drugs for disorders of the cardiovascular system · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61P1/16

  for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics · 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