# US 11,027,043 B1 · Crosslinked gels comprising polyalkyleneimines, and their uses as medical devices

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,027,043 B1
- Document ID: US11027043B1
- Status: Granted
- Kind: B1
- Application number: 16/894,107
- Filed: 2020-06-05
- Granted: 2021-06-08
- Earliest claimed: 2006-01-11
- Assignees: HyperBranch Medical Technology, Inc.
- Applicants: HyperBranch Medical Technology, Inc.
- Inventors: Kenneth E. Stockman; Michael A. Carnahan; Keith R. D'Alessio; Mark W. Grinstaff
- Web page: https://patentgrep.com/patent/US11027043B1

## CPC

- A61L 26/0019: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds}
- A61K 31/785: Polymers containing nitrogen
- A61K 31/787: containing heterocyclic rings having nitrogen as a ring hetero atom
- A61L 24/0031: {Hydrogels or hydrocolloids}
- A61L 24/0036: {Porous materials, e.g. foams or sponges}
- 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)}
- A61L 26/0052: {Mixtures of macromolecular compounds}
- A61L 26/008: {Hydrogels or hydrocolloids}
- A61L 26/0085: {Porous materials, e.g. foams or sponges}
- A61L 27/18: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 27/26: Mixtures of macromolecular compounds
- A61L 27/52: Hydrogels or hydrocolloids
- A61L 27/56: Porous materials, {e.g. foams or sponges}
- A61B 2017/0065: {the implement being an adhesive}
- A61B 2017/00951: {adhesive}
- A61K 51/1279: {Plasters, bandages, dressings, patches or adhesives}
- A61L 24/00: Surgical adhesives or cements; Adhesives for colostomy 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)
- A61B: DIAGNOSIS; SURGERY; IDENTIFICATION (usefulness limited to only animals A61D)

## Abstract

One aspect of the present invention generally relates to methods of sealing a wound or tissue plane or filling a void splace. In a preferred embodiment, the wound is an ophthalmic, pleural or dural wound. In certain instances, the compositions used to seal the wound or tissue plane comprises a polyalkyleneimine. In a preferred embodiment, the polyalkyleneimine is polyethyleneimine. Treatment of the polyethyleneimine with a cross-linking reagent causes the polyethyleneimine polymers to polymerize forming a seal. In certain instances, the cross-linking reagent is a polyethylene glycol having reactive terminal groups. In certain instances, the reactive terminal groups are activated esters, such as N-hydroxy succinimide ester. In certain instances, the reactive terminal groups are isocyanates. In certain instances, the polyethyleneimine has a lysine, cysteine, isocysteine or other nucleophilic group attached to the periphery of the polymer. In certain instances, the polyethyleneimine is mixed with a second polymer, such as a polyethylene glycol containing nucleophilic groups. In certain instances, the compositions used to seal the wound or tissue plane are formed by reacting a polyalkyleneimine bearing electrophilic groups with a cross-linking reagent containing nucleophilic groups. In certain instances, the electrophilic groups on the polyalkyleneimine are activated esters, such as N-hydroxy succinimide ester. In certain instances, the compositions used to seal the wound or tissue plane are formed by reacting a polyalkyleneimine bearing photopolymerizable groups with ultraviolet or visibile light. Compositions used to seal the wound which contain PEI or a derivative of PEI are found to adhere tightly to the tissue. Other aspects of the present invention relate to methods of filling a void of a patient or adhering tissue. In certain instances, the methods use a polyalkyleneimine. In a preferred embodiment, the polyalkyleneimine is polyethyleneimine. Another aspect of the present invention relates to a polymeric composition formed by exposing a polyalkyleneimine to an activated polyalkylene glycol. In certain instances, the composition is attached to mammalian tissue.

## Claims

### Claim 1

A method of treating a patient, comprising the steps of:
exposing an effective amount of polyethyleneimine (PEI) to an activated polyethylene glycol represented by the following formula III to form an adhesive composition; and
applying said adhesive composition to a tissue of the patient,
wherein formula III is represented by:
B(R1-III)2
wherein B is
wherein R2-III is H, v is 2, and w is 15 to 90,
wherein R1-III is
wherein R5-III is H, R6-III is C1 to C4 alkyl, and A1-III is optionally substituted phenyl radical.