# US 10,946,100 B2 · Polymers including active agents

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- Number: US 10,946,100 B2
- Document ID: US10946100B2
- Status: Granted
- Kind: B2
- Application number: 16/250,878
- Filed: 2019-01-17
- Published: 2019-05-23
- Granted: 2021-03-16
- Earliest claimed: 2014-04-29
- Assignees: MicroVention, Inc.
- Applicants: MicroVention, Inc.
- Inventors: Gregory M. Cruise; Clayton G. Harris; Michael J. Constant
- Web page: https://patentgrep.com/patent/US10946100B2

## CPC

- A61K 47/32: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone}
- A61K 9/0092: {Hollow drug-filled fibres, tubes of the core-shell type, coated fibres, coated rods, microtubules or nanotubes}
- A61K 31/7068: having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
- A61K 31/787: containing heterocyclic rings having nitrogen as a ring hetero atom
- A61K 47/58: obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
- A61K 49/04: X-ray contrast preparations
- A61L 31/145: {Hydrogels or hydrocolloids}
- A61L 31/148: {Materials at least partially resorbable by the body}
- A61L 31/16: Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)}
- A61L 31/18: Materials at least partially X-ray or laser opaque
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 35/00: Antineoplastic agents
- C07F 15/0093: {without a metal-carbon linkage}
- C07H 19/06: Pyrimidine radicals
- A61L 2430/36: for embolization or occlusion, e.g. vaso-occlusive compositions or devices
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

Polymers are described herein comprising: a reaction product of a prepolymer solution including at least one macromer and at least one visualization agent; and an active agent electrostatically bound to the polymer filament or chemically bound to the at least one monomer; wherein the polymer filament does not include metallic support members.

## Claims

### Claim 1

A method of forming a therapeutic polymer filament comprising:
reacting a prepolymer solution including:
at least one macromer selected from ethoxylated pentaerythritol, ethoxylated trimethylolpropane, or a combination thereof,
at least one visualization agent, and
a polymerizable pharmaceutical agent having a structure
wherein R1 is
wherein each R2 and R3 can independently be H, CH3, C2-C6 alkyl, C2-C6 substituted with a halogen or other C1-C6 alkyl, NH2, CO2, ON, CF3, F, Cl, Br, I, CCl3, OH, or CH2OH;
n is 1, 2, 3, or 4;
m is 1, 2, 3, or 4;
X1, X2, X3, and X4 are each N or CH; and
X5 is O, CH2, or NH; and
p is 0, 1, 2, 3 or 4
thereby forming the therapeutic polymer filament wherein the polymerizable pharmaceutical agent is chemically bound to the therapeutic polymer filament.

### Claim 2 (depends on 1)

The method of claim 1, further comprising adding at least one crosslinker to the prepolymer solution, wherein the at least one crosslinker includes an ester, a carbonate, a thioester, or a combination thereof.

### Claim 3 (depends on 1)

The method of claim 1, further comprising adding at least one monomer to the prepolymer solution, wherein the at least one monomer is t-butyl acrylamide, 2-hydroxyethyl methacrylate, hydroxyl propyl acrylate, hydroxyl butylacrylate, or a combination thereof.

### Claim 4 (depends on 3)

The method of claim 3, wherein the at least one monomer has a concentration of between about 5% and about 40% w/w of the prepolymer solution.

### Claim 5 (depends on 1)

The method of claim 1, wherein the at least one macromer has a concentration of between about 15% and about 25% w/w of the prepolymer solution or has a molecular weight of between about 100 g/mole and about 5,000 g/mole.

### Claim 6 (depends on 1)

The method of claim 1, wherein the at least one visualization agent is barium, bismuth, tantalum, platinum, gold, iodine-containing molecules, barium sulfate, or a combination thereof.

### Claim 7 (depends on 1)

The method of claim 1, wherein the at least one visualization agent is an iodine-containing molecule.

### Claim 8

A method of forming a therapeutic polymer filament comprising:
reacting a prepolymer solution including:
at least one macromer selected from poly(ethylene glycol), poly(propylene glycol), poly(tetramethylene oxide), ethoxylated pentaerythritol, ethoxylated trimethylolpropane, poly(vinyl alcohol), or a combination thereof, and
a polymerizable pharmaceutical agent having a structure
wherein R1 is
wherein each R2 and R3 can independently be H, CH3, C2-C6 alkyl, C2-C6 substituted with a halogen or other C1-C6 alkyl, NH2; CO2, ON, CF3, F, Cl; Br, I, CCl3, OH, or CH2OH;
n is 1, 2, 3, or 4;
m is 1, 2, 3, or 4;
X1, X2, X3, and X4 are each N or CH; and
X5 is O, CH2, or NH; and
p is 0, 1, 2, 3 or 4
thereby forming the therapeutic polymer filament wherein the polymerizable pharmaceutical agent is chemically bound to the therapeutic polymer filament.

### Claim 9 (depends on 8)

The method of claim 8, further comprising adding at least one monomer to the prepolymer solution, wherein the at least one monomer is t-butyl acrylamide, 2-hydroxyethyl methacrylate, hydroxyl propyl acrylate, hydroxyl butylacrylate, or a combination thereof.

### Claim 10 (depends on 9)

The method of claim 9, wherein the at least one monomer has a concentration of between about 5% and about 40% w/w of the prepolymer solution.

### Claim 11 (depends on 8)

The method of claim 8, wherein the at least one macromer has a concentration of between about 15% and about 25% w/w of the prepolymer solution or has a molecular weight of between about 100 g/mole and about 5,000 g/mole.

### Claim 12 (depends on 8)

The method of claim 8, further comprising at least one visualization agent in the prepolymer solution.

### Claim 13 (depends on 12)

The method of claim 12, wherein the at least one visualization agent is barium, bismuth, tantalum, platinum, gold, iodine-containing molecules, barium sulfate, or a combination thereof.

### Claim 14 (depends on 12)

The method of claim 12, wherein the at least one visualization agent is an iodine-containing molecule.

### Claim 15 (depends on 8)

The method of claim 8, further comprising at least one crosslinker, wherein the at least one crosslinker includes an ester, a carbonate, a thioester, or a combination thereof.

### Claim 16

A method of forming a therapeutic polymer filament comprising:
reacting a prepolymer solution including:
at least one macromer selected from polyethylene glycol), poly(propylene glycol), poly(tetramethylene oxide), ethoxylated pentaerythritol, ethoxylated trimethylolpropane, poly(vinyl alcohol), or a combination thereof, and
a polymerizable pharmaceutical agent having a structure
thereby forming the therapeutic polymer filament wherein the polymerizable pharmaceutical agent is chemically bound to the therapeutic polymer filament.

### Claim 17 (depends on 16)

The method of claim 16, further comprising adding at least one monomer to the prepolymer solution, wherein the at least one monomer is t-butyl acrylamide, 2-hydroxyethyl methacrylate, hydroxyl propyl acrylate, hydroxyl butylacrylate, or a combination thereof.

### Claim 18 (depends on 17)

The method of claim 17, wherein the at least one monomer has a concentration of between about 5% and about 40% w/w of the prepolymer solution.

### Claim 19 (depends on 16)

The method of claim 16, wherein the at least one macromer has a concentration of between about 15% and about 25% w/w of the prepolymer solution or has a molecular weight of between about 100 g/mole and about 5,000 g/mole.

### Claim 20 (depends on 16)

The method of claim 16, further comprising at least one visualization agent in the prepolymer solution.

### Claim 21 (depends on 20)

The method of claim 20, wherein the at least one visualization agent is barium, bismuth, tantalum, platinum, gold, iodine-containing molecules, barium sulfate, or a combination thereof.

### Claim 22 (depends on 20)

The method of claim 20, wherein the at least one visualization agent is an iodine-containing molecule.

### Claim 23 (depends on 16)

The method of claim 16, further comprising at least one crosslinker, wherein the at least one crosslinker includes an ester, a carbonate, a thioester, or a combination thereof.