US 11,702,498 B2
Radiopaque polymers
Andrew Lennard Lewis, Farnham (GB); Hugh Britton, Gillingham (GB); Yiqing Tang, Guildford (GB); Jonathan Vince, Hampshire (GB); Koorosh Ashrafi, Purley (GB); and Damien Guegan, Fontaine (FR)
Assigned to Biocompatibles UK Limited
Appl. No. 17/252,560
Filed by BIOCOMPATIBLES UK LIMITED, Farnham (GB)
PCT Filed Jun. 26, 2019, PCT No. PCT/IB2019/055382
§ 371(c)(1), (2) Date Dec. 15, 2020,
PCT Pub. No. WO2020/003147, PCT Pub. Date Jan. 2, 2020.
Claims priority of application No. 1810777 (GB), filed on Jun. 29, 2018; and application No. 1810788 (GB), filed on Jun. 29, 2018.
Prior Publication US 2021/0277162 A1, Sep. 9, 2021
Int. Cl. C08F 261/04 (2006.01); A61K 9/00 (2006.01); A61K 9/16 (2006.01); A61K 49/04 (2006.01); A61L 24/00 (2006.01); A61L 24/04 (2006.01); C08G 67/00 (2006.01)
CPC C08F 261/04 (2013.01) [A61K 9/0024 (2013.01); A61K 9/1635 (2013.01); A61K 49/0442 (2013.01); A61L 24/001 (2013.01); A61L 24/0015 (2013.01); A61L 24/046 (2013.01); C08G 67/00 (2013.01); A61L 2400/06 (2013.01); A61L 2430/36 (2013.01)] 17 Claims
 
1. A radiopaque microsphere comprising a hydrophilic polymer comprising pendent groups of the formula I:

OG Complex Work Unit Chemistry
wherein:
W is independently selected from —OH, —COOH, —SO3H, —OPO3H, —O—(C1-4 alkyl), —O—(C1-4 alkyl)OH, —O—(C1-4 alkyl)R2, —O—(C2H5O)qR1—(C═O)—O—C1-4 alkyl and —O—(C═O)C1-4 alkyl; or a group —BZ; wherein —OH, COOH, O—PO3H and SO3H maybe in the form of a pharmaceutically acceptable salt;
wherein:
B is a bond, or a straight branched alkanediyl, oxyalkylene, alkylene oxaalkylene, or alkylene group, optionally containing one or more fluorine substituents;
Z is an ammonium, phosphonium, or sulphonium phosphate or phosphonate ester zwitterionic group;
X is either a bond or a linking group having 1 to 8 carbons and optionally 1 to 4 heteroatoms selected from O, N and S;
G is a coupling group through which the group of the formula I is coupled to the polymer and is selected from 1,3 dioxolane and 1,3 dioxane;
R1 is H or C1-4 alkyl;
R2 is —COOH, —SO3H, or —OPO3H2
q is an integer from 1 to 4;
n is an integer from 1 to 4;
p is an integer from 1 to 3; and
n+p is from 2 to 5; and
wherein —COOH, —OPO3H2 and —SO3H as well as phenolic —OH may be in the form of a pharmaceutically acceptable salt.