Granted Patent B2

US 12,734,255 · App. 16/346,920 · Granted Sep 15, 2026

Inventors: Stephen D. Goodrich (Boulder, CO); Jeffrey P. Castleberry (Boulder, CO)

Assignee: Embolization, Inc.

A61K49/0442A61K49/0447A61L27/16A61L27/50A61L29/041A61L29/18A61L31/048A61L31/18A61P41/00A61L2430/06

Abstract

Claims (77)

1 . A crosslinked polymer network comprising:

a) a plurality of first repeating units comprising a first reagent, the first reagent defined by the formula FX1a, FX1b, FX1c or FX1d:

wherein:

X is Br or I;

m is an integer selected from the range of 1 to 5;

each R 11 is, independently, a substituted or unsubstituted C 6 -C 20 alkylene group;

each L 11 is, independently, a single bond, —(CH 2 ) j —, —(HCCH) j —, —O—, —S—, —SO—, —SO 2 —, —SO 3 —, —OSO 2 —, —NR 12 , —CO—, —COO—, —OCO—, —OCOO—, —CONR 13 —, —NR 14 CO—, —OCONR 15 —, —NR 16 COO—, —NR 17 CONR 18 —, —SiO(Z 1 )(Z 2 )—, or —Si[SiO(Z 1 )(Z 2 )] n —,

wherein Z 1 is given by the formula L 1 (T 1 ) p and Z 2 is given by the formula L 2 (T 2 ) q , and

wherein each of L 1 and L 2 are, independently, a single bond, a polyvalent alkane radical having from 1 to 36 carbon atoms, a polyvalent heteroalkane radical having from 1 to 36 carbon atoms and including —O— or —C(O)O—, a polyvalent aryl radical having from 1 to 36 carbon atoms, or a polyvalent heteroaryl radical having from 1 to 36 carbon atoms and including —O— or —C(O)O—, and

wherein each of T 1 and T 2 are, independently, a polymerizable group having a terminal (meth)acrylate, (meth)acrylamide or styryl group, and

wherein n is an integer selected from the range of 1-10;

each Ar 11 is, independently, an iodine- or bromine-containing C 5 -C 36 aryl group containing one or more rings, or an iodine- or bromine-containing C 5 -C 36 heteroaryl group containing one or more rings; and

wherein each of R 12 -R 18 is, independently, hydrogen or a C 1 -C 10 alkyl group and each j is, independently, an integer selected from the range of 1 to 10;

b) a plurality of second repeating units comprising a second reagent, the second reagent defined by the formula Z 3 a X 1 c Si d O e Z 4 b ;

wherein:

Z 3 is given by the formula L 3 (T 3 ) p and Z 4 is given by the formula L 4 (T 4 ) q ,

wherein each of L 3 and L 4 are, independently, a single bond, a polyvalent alkane radical having from 1 to 36 carbon atoms, a polyvalent heteroalkane radical having from 1 to 36 carbon atoms and including —O— or —C(O)O—, a polyvalent aryl radical having from 1 to 36 carbon atoms, or a polyvalent heteroaryl radical having from 1 to 36 carbon atoms and including —O— or —C(O)O—,

wherein each of T 3 and T 4 are, independently, a polymerizable group having a terminal (meth)acrylate, (meth)acrylamide, or styryl group;

each X 1 is, independently, an alkyl group, a (meth)acrylate group, a (meth)acrylamide group, or a styryl group having 1 to 36 carbon atoms;

each a, b and d are, independently, integers selected from the range of 1 to 10 and each c and e are, independently, integers selected from the range of 1 to 20; and

p and q are each, independently, an integer selected from the range of 1 to 9; and

c) a plurality of third repeating units comprising a third reagent, the third reagent comprising at least three terminal (meth)acrylate, (meth)acrylamide, or styryl groups.

2 . The crosslinked polymer network of claim 1 , wherein Ar 11 is an iodine containing C 6 aryl group with 3 to 5 iodine atoms attached directly to the ring.

3 . The crosslinked polymer network of claim 1 , wherein R 11 is a C 6 -C 24 alkylene group.

4 . The crosslinked polymer network of claim 1 , wherein said first reagent is defined by the formula FX2:

wherein r is an integer selected from the range of 2 to 18.

5 . The crosslinked polymer network of claim 1 , wherein said third reagent is defined by the formula FX3:

wherein:

R 10 is C, N, O, a substituted or unsubstituted C 2 -C 36 multivalent alkane radical, or a substituted or unsubstituted C 2 -C 36 alkylene;

each of L 9 and L 10 are, independently, a single bond, a polyvalent straight or branched C 2 -C 12 alkane radical, a polyvalent straight or branched C 2 -C 12 heteroalkane radical including —O— or —C(O)O—, —(CH 2 ) n —, —(HCCH) n —, —O—, —S—, —SO—, —SO 2 —, —SO 3 —, —OSO 2 —, —NR 3 —, —CO—, —COO—, —OCO—, —OCOO—, —CONR 4 —, —NR 5 CO—, —OCONR 6 —, —NR 7 COO—, or —NR 8 CONR 9 , wherein each of R 3 -R 9 is, independently, hydrogen or C 1 -C 10 alkyl, and each n is, independently, an integer selected from 1 to 10;

each T 9 and each T 10 are, independently, a polymerizable group having a terminal (meth)acrylate, (meth)acrylamide or styryl group; and

w and v are each, independently, integers from 1 to 9.

6 . The crosslinked polymer network of claim 5 , wherein:

R 10 is O;

each T 9 and each T 10 are (meth)acrylate; and

w and v are each, independently, integers from 1 to 6.

7 . The crosslinked polymer network of claim 1 , wherein said second reagent is defined by the formula FX5a:

wherein A 1 is Si or is defined by the formula FX5b, FX5c, FX5d, FX5e or FX5f:

wherein:

each X 1 is, independently, an alkyl group, a (meth)acrylate group, a (meth)acrylamide group, or a styryl group having 1 to 36 carbon atoms;

each n is, independently, selected from the range of 1 to 10;

each of p and q are, independently, integers from 1 to 9;

each L 3 and L 4 is, independently, a single bond, C, N, O, a polyvalent alkane radical having from 1 to 36 carbon atoms, a polyvalent heteroalkane radical having from 1 to 36 carbon atoms and including —O— or —C(O)O—, a polyvalent aryl radical having from 1 to 36 carbon atoms, or a polyvalent heteroaryl radical having from 1 to 36 carbon atoms and including —O— or —C(O)O—, a straight or branched C 2 -C 12 alkylene group, a straight or branched C 2 -C 12 oxyalkylene group, a straight or branched C 2 -C 12 carboxyalkylene group, a straight or branched C 2 -C 12 oxyarylene group, or a straight or branched C 2 -C 12 carboxyarylene group; and

each T 3 and T 4 is, independently, a polymerizable group having a terminal(meth)acrylate, (meth)acrylamide, or styryl group.

8 . The crosslinked polymer network of claim 7 , wherein said second reagent is defined by the formula FX5g:

wherein n selected from the range of 1 to 10.

9 . The crosslinked polymer network of claim 1 , wherein said crosslinked polymer network has greater than or equal to 15 wt % of said first reagent, said crosslinked polymer network has less than or equal to 85 wt % of said second reagent, said crosslinked polymer network has less than or equal to 85 wt % of said third reagent, or a combination thereof.

10 . The crosslinked polymer network of claim 1 , wherein said crosslinked polymer network comprises between 80 to 90 wt % of said first reagent, 1 to 10 wt % of said second reagent, and 5 to 15 wt % of said third reagent.

11 . A radiopaque polymer device for medical application, comprising a polymer composition according to claim 1 , optionally comprising a fiber, a coil or a mesh.

12 . The radiopaque polymer device of claim 11 , wherein the device provides the function of:

opening an anatomical lumen; or

closing an anatomical lumen, either partially as a valve, or complete lumen occlusion; or

support of an anatomical structure to assist in the therapeutic restoration of an organ, vascular, digestive, excrement, or airway function; or

support of an anatomical structure to assist in therapeutic restoration of an orthopedic, maxiofacial, spinal, or joint function; or

to support homeostasis by covering an area after tissue dissection or resection.

13 . The radiopaque polymer device of claim 11 , for purposes of a diagnostic or therapeutic instrument or device to provide the function of:

a catheter for the purposes of accessing an anatomical location; delivering another device and/or therapeutic agent; or controlling the access or delivery of another device and/or therapeutic agent.

14 . The radiopaque polymer device of claim 11 , having a cylindrical shape with a diameter less than or equal to 0.015 inches.

15 . A crosslinked polymer network comprising:

a) a plurality of first repeating units comprising a first reagent, the first reagent defined by the formula FX1a, FX1b, FX1c or FX1d:

wherein:

X is Br or I;

m is an integer selected from the range of 1 to 5;

each R 11 is, independently, a substituted or unsubstituted C 7 -C 20 alkylene group; each L 11 is independently a single bond, —(CH 2 ) j —, —(HCCH) j —, —O—, —S—, —SO—, —SO 2 —, —SO 3 —, —OSO 2 —, —NR 12 , —CO—, —COO—, —OCO—, —OCOO—, —CONR 13 —, —NR 14 CO—, —OCONR 15 —, —NR 16 COO—, —NR 17 CONR 18 —, —SiO(Z 1 )(Z 2 )—, or —Si[SiO(Z 1 )(Z 2 )] n —,

wherein Z 1 is given by the formula L′(T 1 ) p and Z 2 is given by the formula L 2 (T 2 ) q ,

wherein each of L 1 and L 2 are, independently, a single bond, a polyvalent alkane radical having from 1 to 36 carbon atoms, a polyvalent heteroalkane radical having from 1 to 36 carbon atoms and including —O— or —C(O)O—, a polyvalent aryl radical having from 1 to 36 carbon atoms, or a polyvalent heteroaryl radical having from 1 to 36 carbon atoms and including —O— or —C(O)O—,

wherein each of T 1 and T 2 are, independently, a polymerizable group having a terminal (meth)acrylate, (meth)acrylamide, or styryl group, and n is an integer selected from the range of 1-10;

each Ar 11 is, independently, an iodine- or bromine-containing C 5 -C 36 aryl group containing one or more rings, or an iodine- or bromine-containing C 5 -C 36 heteroaryl group containing one or more rings, wherein each of R 12 -R 18 is, independently, hydrogen or a C 1 -C 10 alkyl group and each j is, independently, an integer selected from the range of 1 to 10;

b) a plurality of second repeating units comprising a second reagent, the second reagent defined by the formula Z 3 a X 1 c Si d O e Z 4 b ;

wherein:

Z 3 is given by the formula L 3 (T 3 ) p and Z 4 is given by the formula L 4 (T 4 ) q ;

wherein each of L 3 and L 4 are, independently, a single bond, a polyvalent alkane radical having from 1 to 36 carbon atoms, a polyvalent heteroalkane radical having from 1 to 36 carbon atoms and including —O— or —C(O)O—, a polyvalent aryl radical having from 1 to 36 carbon atoms, or a polyvalent heteroaryl radical having from 1 to 36 carbon atoms and including —O— or —C(O)O—,

wherein each of T 3 and T 4 are, independently, a polymerizable group having a terminal (meth)acrylate, (meth)acrylamide, or styryl group;

each X 1 is, independently, an alkyl group, a (meth)acrylamide group, or a styryl group having 1 to 36 carbon atoms;

each a, b and d are, independently, integers selected from the range of 1 to 10 and each c and e are, independently, integers selected from the range of 1 to 20; and

p and q are each, independently, an integer selected from the range of 1 to 9; and

c) a plurality of third repeating units, each of the third repeating units comprising at least three terminal (meth)acrylate, (meth)acrylamide, or styryl groups.

Assignments (2)

Continuity (2)

References Cited (23)