# US 11,992,576 B2 · Embolic compositions and methods

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- Number: US 11,992,576 B2
- Document ID: US11992576B2
- Status: Granted
- Kind: B2
- Application number: 17/342,945
- Filed: 2021-06-09
- Published: 2021-12-09
- Granted: 2024-05-28
- Earliest claimed: 2020-06-09
- Assignees: Arsenal Medical, Inc.
- Applicants: Arsenal Medical, Inc.
- Inventors: Jeffrey Groom; Craig Wiltsey; Quynh Pham; Nikhita Mansukhani; Courtney Guertin; Lee Core; Upma Sharma
- Web page: https://patentgrep.com/patent/US11992576B2

## CPC

- A61L 24/06: obtained by reactions only involving carbon-to-carbon unsaturated bonds {(A61L24/043, A61L24/046 take precedence)}
- A61K 47/02: Inorganic compounds
- A61K 47/34: 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)
- A61K 49/04: X-ray contrast preparations
- A61K 49/0409: {Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is not a halogenated organic compound}
- A61L 24/0021: {Plasticisers}
- A61L 24/02: containing inorganic materials
- A61L 24/043: {Mixtures of macromolecular materials}
- A61L 24/046: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds (A61L24/043 takes precedence)}
- C08L 83/04: Polysiloxanes
- A61L 2400/06: Flowable or injectable implant compositions
- A61L 2430/36: for embolization or occlusion, e.g. vaso-occlusive compositions or devices
- 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)
- 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)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The present disclosure pertains to crosslinkable compositions and systems as well as methods for forming crosslinked compositions in situ, including the use of the same for embolizing vasculature including the neurovasculature within a patient, among many other uses.

## Claims

### Claim 1

A kit for forming crosslinkable compositions for vascular embolization, said kit comprising:
(a) a first fluid composition comprising a first polysiloxane having two or more unsaturated groups and a first imaging agent,
(b) a second fluid composition that comprises a first hydride material having two or more hydride groups and a second imaging agent which is the same or different from the first imaging agent,
(c) a dry composition comprising a first silica filler and optionally a second silica filler which is the same or different from the first silica filler, and
wherein the first fluid composition, second fluid composition, and dry composition are stable, and when mixed, form a crosslinkable composition having the first and second imaging agents substantially evenly dispersed in the crosslinkable composition; and
wherein the crosslinkable composition cures into a solid when injected into a target vessel and occludes the target vessel.

### Claim 2 (depends on 1)

The kit of claim 1, further comprising one or more components for mixing the first fluid composition, the second fluid composition, and the dry composition to form a crosslinkable composition and for delivering the crosslinkable composition to a target site within a body.

### Claim 3 (depends on 2)

The kit of claim 2, wherein the component for delivering the crosslinkable composition is a catheter.

### Claim 4 (depends on 1)

The kit of claim 1, wherein the dry composition is mixed into the fluid compositions at the time of use to form a composition.

### Claim 5 (depends on 1)

The kit of claim 1, wherein the first and second imaging agents comprise metal oxides.

### Claim 6 (depends on 1)

The kit of claim 1, wherein the first and second imaging agents comprise bismuth trioxide.

### Claim 7 (depends on 1)

The kit of claim 1, wherein the first and second imaging agent are of a size ranging from 10 nm to 20 μm.

### Claim 8 (depends on 1)

The kit of claim 1, wherein once formed, the crosslinkable composition is injectable by hand.

### Claim 9 (depends on 1)

The kit of claim 1, wherein the first silica filler and the second silica filler, if present, is hydrophobic.

### Claim 10 (depends on 1)

The kit of claim 1, wherein the first and the second silica filler, if present, are the same.

### Claim 11 (depends on 9)

The kit of claim 9, wherein the first and the second silica filler, if present, are fumed silica.

### Claim 12 (depends on 1)

The kit of claim 1, wherein at least one of the first and second fluid compositions comprises a catalyst for catalyzing a reaction between the unsaturated groups and the hydride groups, or the kit further comprises a third and/or fourth fluid composition comprising a catalyst for catalyzing a reaction between the unsaturated groups and the hydride groups.

### Claim 13 (depends on 12)

The kit of claim 12, wherein the first fluid composition comprises the catalyst and the second fluid composition does not comprise a catalyst.

### Claim 14 (depends on 13)

The kit of claim 13, wherein the second fluid composition comprises a second polysiloxane having two or more unsaturated groups, and wherein the second polysiloxane is the same as or different from the first polysiloxane.

### Claim 15 (depends on 12)

The kit of claim 12, wherein the second fluid composition comprises the catalyst and the first fluid composition does not comprise a catalyst.

### Claim 16 (depends on 15)

The kit of claim 15, wherein the first fluid composition comprises a second hydride material having two or more hydride groups, and wherein the second hydride material is the same as or different from the first hydride material.

### Claim 17 (depends on 1)

The kit of claim 1, wherein the crosslinkable composition comprises a total amount of at least 10 wt % of the first and second imaging agent.

### Claim 18 (depends on 1)

The kit of claim 1, wherein the ratio of the volume of the first fluid composition to the volume of the second fluid composition is in the range of from 4:1 to 1:4.

### Claim 19 (depends on 1)

The kit of claim 1, wherein the crosslinkable composition comprises a molar ratio of vinyl groups to hydride groups of ≥0.9:1.

### Claim 20 (depends on 1)

The kit of claim 1, wherein the first polysiloxane is a vinyl-terminated polysiloxane, an acrylate-terminated polysiloxane, or a methylacrylate-terminated polysiloxane.

### Claim 21 (depends on 1)

The kit of claim 1, wherein the first polysiloxane has a weight average molecular weight ranging from 250 Da to 10,000 Da.

### Claim 22 (depends on 1)

The kit of claim 1, wherein the first polysiloxane is a multifunctional polysiloxane hydride having a weight average molecular weight ranging from 300 to 13,000 Da.

### Claim 23 (depends on 1)

The kit of claim 1, wherein the crosslinkable composition contains a catalyst modifier.

### Claim 24 (depends on 1)

The kit of claim 1, wherein the first fluid composition, second fluid composition, dry composition and/or the crosslinkable composition are subjected to terminal sterilization.

### Claim 25

A method comprising
(a) forming a crosslinkable composition for vascular embolization comprising:
annealing a first fluid composition comprising a first polysiloxane having two or more unsaturated groups and a first imaging agent, annealing a second fluid composition comprising a hydride material having two or more hydride groups and a second imaging agent that is the same or different from the first imaging agent, and at the time of use, mixing the first and second fluid compositions with a dry composition comprising a first silica filler and optionally a second silica filler that is the same or different from the first silica filler to form the crosslinkable composition, wherein the first and second imaging agents are substantially evenly dispersed in the crosslinkable composition and
(b) injecting the crosslinkable composition into the vasculature of a patient whereupon the crosslinkable composition crosslinks and forms a solid which occludes a target vessel into which it is injected.

### Claim 26 (depends on 25)

The method of claim 25 wherein the method is a vascular embolization method.

### Claim 27 (depends on 25)

The method of claim 25, wherein method is a method for (1) occlusion of the vasculature for treatment of tumors, (2) pre-surgical embolization of tumors, (3) treatment of chronic subdural hematoma, brain aneurysms, arteriovenous malformations, arteriovenous fistulas, gastrointestinal bleeds, bleeding due to trauma, abdominal aortic aneurysm, intracranial aneurysm, pulmonary aneurysm, or hemorrhage, (4) prostate artery embolization or uterine artery embolization, (5) treatment of visceral aneurysms, varicoceles, or varices, (6) treatment for pelvic congestion, (7) treatment of epistaxis or (8) treatment of endoleaks.

### Claim 28 (depends on 25)

The method of claim 25, wherein the method further comprises identifying a blood vessel that branches into smaller distal vessels and injecting the crosslinkable composition into the blood vessel such that the crosslinkable composition flows into the distal vessels and occludes the distal vessels.

### Claim 29 (depends on 25)

The method of claim 25, wherein the crosslinkable composition is injected into the vasculature or neurovasculature of the patient via a catheter.