# US 2014/0154204 A1 · Silane-containing moisture-curable tissue sealant

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- Number: US 2014/0154204 A1
- Document ID: US20140154204A1
- Status: Published application
- Kind: A1
- Application number: 13/693,218
- Filed: 2012-12-04
- Published: 2014-06-05
- Earliest claimed: 2012-12-04
- Assignees: Cohera Medical, Inc.
- Applicants: Cohera Medical, Inc.
- Inventors: Dottie Clower; Despina Dobbins; Stephanie Kladakis
- Web page: https://patentgrep.com/patent/US20140154204A1

## CPC

- A61K 31/80: Polymers containing hetero atoms not provided for in groups A61K31/755 - A61K31/795
- F04C 2270/0421: Controlled or regulated
- 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)
- F04C: ROTARY-PISTON, OR OSCILLATING-PISTON, POSITIVE-DISPLACEMENT MACHINES FOR LIQUIDS (engines F03C); ROTARY-PISTON, OR OSCILLATING-PISTON, POSITIVE-DISPLACEMENT PUMPS

## Abstract

A tissue sealant that includes the reaction product of (a) a polyol; (b) a polyisocyanate; and (c) an alkoxy silane having the formula: (R1R2R3)—Si—CH2—Z where (i) Z is an —OH, —SH, —NCO, or —NHR4 group, where R4 is hydrogen, an alkyl group, or an aryl group; and (ii) 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, the relative amounts of the polyol, polyisocyanate, and alkoxy silane being selected such that the reaction product comprises free isocyanate groups. The tissue sealant is moisture-curable and biodegradable in a physiological environment.

## Claims

### Claim 1

A tissue sealant comprising the reaction product of:
(a) a polyol;
(b) a polyisocyanate; and
(c) an alkoxy silane having the formula: (R1R2R3)—Si—CH2—Z where:
(i) Z is an —OH, —SH, —NCO, or —NHR4 group, where R4 is hydrogen, an alkyl group, or an aryl group; and
(ii) 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,
wherein the relative amounts of the polyol, polyisocyanate, and alkoxy silane are selected such that the reaction product comprises free isocyanate groups, wherein the tissue sealant is moisture-curable and biodegradable in a physiological environment.

### Claim 2 (depends on 1)

A tissue sealant according to claim 1 further comprising an isocyanate-functional organosilane having 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 3 (depends on 2)

A tissue sealant according to claim 2 wherein the isocyanate-functional organosilane has a molecular weight no greater than 500 g/mole.

### Claim 4 (depends on 2)

A tissue sealant according to claim 2 wherein the isocyanate-functional organosilane has a molecular weight no greater than 300 g/mole.

### Claim 5 (depends on 2)

A tissue sealant according to claim 2 wherein the isocyanate-functional organosilane has the formula: (R5R6R7)—Si—R8—NCO where R8 is a C1-C10 alkyl group.

### Claim 6 (depends on 1)

A tissue sealant according to claim 1 wherein two of R1, R2, and R3 are C1-C6 alkoxy groups.

### Claim 7 (depends on 1)

A tissue sealant according to claim 1 wherein each of R1, R2, and R3 is a C1-C6 alkoxy group.

### Claim 8 (depends on 1)

A tissue sealant according to claim 1 wherein Z is an —NHR4 group.

### Claim 9 (depends on 8)

A tissue sealant according to claim 8 where R4 is a phenyl group.

### Claim 10 (depends on 2)

A tissue sealant according to claim 2 wherein at least one of R5, R6, and R7 is a C1-C6 alkoxy group.

### Claim 11 (depends on 2)

A tissue sealant according to claim 2 wherein each of R5, R6, and R7 is a C1-C6 alkoxy group.

### Claim 12 (depends on 2)

A tissue sealant according to claim 2 wherein each of R5, R6, and R7 is a C1-C6 alkoxy group, and R8 has the formula: —(CH2)n— where n=1−10.

### Claim 13 (depends on 1)

A tissue sealant according to claim 1 wherein the polyol is selected from the group consisting of polyether polyols, polyester polyols, co-polyester polyether polyols, alkoxylated glycerol derivatives, and combinations thereof.

### Claim 14 (depends on 1)

A tissue sealant according to claim 1 wherein the polyisocyanate is selected from the group consisting of lysine diisocyanate and derivatives thereof, lysine triisocyanate and derivatives thereof, and combinations thereof.

### Claim 15 (depends on 1)

A tissue sealant according to claim 1 wherein the tissue sealant comprises the reaction product of the alkoxy silane, the polyisocyanate, and at least two different polyols.

### Claim 16 (depends on 1)

A tissue sealant according to claim 1, wherein the tissue sealant further comprises at least one reagent selected from the group consisting of solvents, diluents, catalysts, coagulents, and combinations thereof.

### Claim 17 (depends on 1)

A tissue sealant according to claim 1, wherein the tissue sealant further comprises a colorant.

### Claim 18 (depends on 17)

A tissue sealant according to claim 17, wherein the colorant comprises beta-carotene.

### Claim 19 (depends on 1)

A method of sealing tissue comprising:
(a) applying a sealant according to claim 1 to a tissue surface; and
(b) curing the sealant to seal the area of tissue to which the sealant was applied.