# US 11,433,162 B2 · Meniscal repair adhesive

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- Number: US 11,433,162 B2
- Document ID: US11433162B2
- Status: Granted
- Kind: B2
- Application number: 17/079,624
- Filed: 2020-10-26
- Published: 2021-02-11
- Granted: 2022-09-06
- Earliest claimed: 2015-08-31
- Assignees: Arthrex, Inc.
- Applicants: Arthrex, Inc.
- Inventors: Dottie M. Clower; Eric J. Beckman; Bradd N. Picone
- Web page: https://patentgrep.com/patent/US11433162B2

## CPC

- A61L 27/18: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 24/046: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds (A61L24/043 takes precedence)}
- C08L 83/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08L 91/00: Compositions of oils, fats or waxes; Compositions of derivatives thereof
- A61L 2400/06: Flowable or injectable implant compositions
- A61L 2430/06: for cartilage reconstruction, e.g. meniscus
- A61L 2430/10: for reconstruction of tendons or ligaments
- 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)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

A composition that includes (a) a prepolymer having at least one free isocyanate group that is capable of bonding to tissue and that cures in vivo upon exposure to water to form a polymer having a compressive modulus between 1.9 and 14.4 MPa and a tensile modulus between 5.0 and 30, and (b) an oil that is miscible in the prepolymer, the oil being selected from the group consisting of silicone oils, mineral oil, vegetable oils, and combinations thereof. The composition retains its integrity when delivered in an aqueous medium.

## Claims

### Claim 1

A composition comprising:
(a) a siloxane prepolymer having at least one free isocyanate group that is capable of bonding to tissue and that cures in vivo upon exposure to water to form a polymer having a compressive modulus between 1.9 and 14.4 MPa and a tensile modulus between 5.0 and 30, and
(b) an oil that is miscible in the siloxane prepolymer, the oil being selected from the group consisting of silicone oils, mineral oil, vegetable oils, and combinations thereof, wherein the composition retains its integrity when delivered in an aqueous medium.

### Claim 2 (depends on 1)

A composition according to claim 1 wherein the siloxane prepolymer has the formula:
where n is 1 to 10; x and y, independently, are 2 to 10; R1, R2, R3, R5, and R6, independently, are selected from the group consisting of hydroxyl groups; straight chain, branched, or cyclic C1-C6 alkyl groups that may be substituted with one or more isocyanate groups; straight chain, branched, or cyclic C1-C6 fluorinated alkyl groups that may be substituted with one or more isocyanate groups; and combinations thereof; R4 is selected from the group consisting of —NCO, —SH, —OH, R7N+X—; R7 is a straight chain, branched, or cyclic C1-C6 alkyl group; and X is selected from the group consisting of F, Cl, Br, and I, with the proviso that at least one of R1, R2, R3, R4, R5 and R6 includes an isocyanate group.

### Claim 3 (depends on 1)

A composition according to claim 1 wherein the siloxane prepolymer comprises the reaction product of an alkoxy silane and an isocyanate-functional organosilane.

### Claim 4 (depends on 3)

A composition according to claim 3 wherein the alkoxy silane has the formula: (R1R2R3)—Si—CH2—Z, where (i) Z is an —OH, —SH, —NCO, or —NHR4 group, (ii) R4 is a hydrogen, an alkyl group, or an aryl group, (iii) each R1, R2, and R3, independently, is H, an alkoxy group, an alkyl group, a heteroalkyl group other than an alkoxy group, an aryl group, or a heteroaryl group, with the proviso that at least two of R1, R2, and R3 are alkoxy groups.

### Claim 5 (depends on 3)

A composition according to claim 3 wherein the isocyanate-functional organosilane has at least one free isocyanate group and at least one terminal silane group having the formula: (R5R6R7)—Si— where each R5, R6, and R7, independently, is H, an alkoxy group, an alkyl group, a heteroalkyl group other than an alkoxy group, an aryl group, or a heteroaryl group.

### Claim 6 (depends on 1)

A composition according to claim 1 wherein the siloxane prepolymer comprises the reaction product of a polyisocyanate and an active hydrogen component selected from the group consisting of polyols, polyamines, polythiols, polycarboxylic acids, and combinations thereof.

### Claim 7 (depends on 1)

A composition according to claim 1 wherein the siloxane prepolymer comprises the reaction product of (a) a polyisocyanate, (b) an active hydrogen component selected from the group consisting of polyols, polyamines, polythiols, polycarboxylic acids, and combinations thereof, and (c) an ionic salt or amino acid component having an average hydroxyl or amino functionality, or combination thereof, of at least 1.

### Claim 8 (depends on 6)

A composition according to claim 6 wherein the active hydrogen components is selected from the group consisting of glycerol, di-glycerol, erythritol, pentaerythritol, arabitol, fucitol, ribitol, sorbitol, mannitol, and combinations, hydroxyalkyl derivatives, and esters thereof.

### Claim 9 (depends on 6)

A composition according to claim 6 wherein the active hydrogen components is selected from the group consisting of hydroxyalkyl derivatives of C3-C10 carboxylic or dicarboxylic acids, and hydroxyalkyl derivatives of C3-C10 hydrocarbons.

### Claim 10 (depends on 6)

A composition according to claim 6 wherein the active hydrogen components is a hydroxyalkyl amine, a di-, tri-, or tetra-alkylene glycol, or combination thereof.

### Claim 11 (depends on 6)

A composition according to claim 6 wherein the active hydrogen components is a polyamine or polyetheramide.

### Claim 12 (depends on 1)

A composition according to claim 1 wherein the composition comprises at least two different prepolymers.

### Claim 13 (depends on 1)

A composition according to claim 1 wherein the oil comprises a silicone oil.

### Claim 14 (depends on 13)

A composition according to claim 13 wherein the silicone oil is selected from the group consisting of polydimethylsiloxane, simethicone, and combinations thereof.

### Claim 15 (depends on 1)

A composition according to claim 1 wherein the tissue is selected from the group consisting of meniscal tissue, cartilage, tendons, and combinations thereof.

### Claim 16 (depends on 1)

A method of repairing a defect in meniscal tissue comprising delivering a composition according to claim 1 to the knee joint in an aqueous environment in the area of the meniscal defect, and allowing the composition to cure and bond to the meniscal tissue.