# US 11,896,607 B2 · Anionically charged chitosan

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

- Number: US 11,896,607 B2
- Document ID: US11896607B2
- Status: Granted
- Kind: B2
- Application number: 16/767,572
- Filed: 2018-11-09
- Published: 2020-12-17
- Granted: 2024-02-13
- Earliest claimed: 2017-11-28
- Assignees: KiOmed Pharma
- Applicants: KiOmed Pharma
- Inventors: Mickaël Chausson; Pierre Douette; Sandrine Emilia Gautier; Philippe Vaesen; Houtaï Choumane; Guillermo Rocasalbas
- Web page: https://patentgrep.com/patent/US11896607B2

## CPC

- A61K 31/722: Chitin, chitosan
- A61K 8/736: {Chitin; Chitosan; Derivatives thereof}
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 31/728: Hyaluronic acid
- A61L 27/20: Polysaccharides
- A61Q 19/00: Preparations for care of the skin
- C08B 37/003: {Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof}
- C08L 5/08: Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
- A61K 47/36: Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K 2800/91: Injection
- A61L 2400/06: Flowable or injectable implant compositions
- A61L 2430/06: for cartilage reconstruction, e.g. meniscus
- A61L 2430/24: for joint reconstruction
- 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)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The present invention relates to a carboxyalkyl chitosan having a zeta potential, measured at pH 7.5, that is less than or equal to −20 mV, compositions comprising same, a process for manufacturing same, and various applications thereof, in particular in the field of therapy, rheumatology, ophthalmology, esthetic medicine, plastic surgery, internal surgery, dermatology or cosmetics.

## Claims

### Claim 1

A method of therapeutic treatment for osteoarthritis or repairing a cartilage defect, said method comprising administering a carboxyalkyl chitosan to a subject in need thereof, wherein said carboxyalkyl chitosan is administered via injection into the synovial fluid or via implantation in the cartilage, wherein said carboxyalkyl chitosan comprises glucosamine units, N-acetyl-glucosamine units, and glucosamine units substituted by a carboxyalkyl group, wherein the carboxyalkyl chitosan is N,O-carboxyalkyl chitosan and has:
a zeta potential, measured at pH 7.5, that is lower than or equal to −18 mV;
a degree of acetylation in a range of about 40% to about 80%, expressed at the number of moles of N-acetyl-glucosamine units relative to the number of moles of total units; and
a degree of substitution by the carboxyalkyl group that is greater than 70% expressed as the number of moles of the substituent carboxyalkyl group relative to the number of moles of total units, and
wherein the carboxyalkyl chitosan is water-soluble at a pH less than 3.5 and at a physiological pH and is sufficiently pure and suitable for providing a non-opalescent aqueous solution for injection, implantation, or instillation to a human or animal subject.

### Claim 2 (depends on 1)

The method of claim 1, wherein said carboxyl chitosan has having a zeta potential, measured at pH 7.5, that is less than or equal to −20 mV.

### Claim 3 (depends on 1)

The method of claim 1, wherein the degree of substitution by the carboxyalkyl group is greater than 70% and no greater than 200% expressed as the number of moles of the substituent carboxyalkyl group relative to the number of moles of total units.

### Claim 4 (depends on 1)

The method of claim 1, wherein the chitosan is derived from the group consisting of Basidiomycetes, mycelium of Ascomycetes, and a mixture thereof.

### Claim 5 (depends on 1)

The method of claim 1, wherein the carboxyalkyl chitosan is suitable for providing a transparent aqueous solution.

### Claim 6 (depends on 1)

The method of claim 1, wherein the carboxyalkyl chitosan is sterilized.

### Claim 7 (depends on 1)

The method of claim 1, wherein said carboxyalkyl chitosan is comprised in an injectable composition.

### Claim 8 (depends on 1)

The method of claim 1, wherein said carboxyalkyl chitosan is comprised in an aqueous solution.

### Claim 9 (depends on 8)

The method of claim 8, wherein said aqueous solution further comprises hyaluronic acid or sodium hyaluronate, either crosslinked or not crosslinked by covalent bonds.

### Claim 10 (depends on 8)

The method of claim 8, wherein said aqueous solution further comprises a reducing sugar.

### Claim 11 (depends on 8)

The method of claim 8, wherein said aqueous solution is comprised in a medical device.

### Claim 12 (depends on 1)

The method of claim 1, wherein said carboxyalkyl chitosan is comprised in a pharmaceutical composition.

### Claim 13 (depends on 12)

The method of claim 12, wherein said pharmaceutical composition further comprises hyaluronic acid or sodium hyaluronate, either crosslinked or not crosslinked by covalent bonds.

### Claim 14 (depends on 12)

The method of claim 12, wherein said pharmaceutical composition is selected from the group consisting of: an injectable pharmaceutical composition suitable for delivery via an injectable medical device, an implantable pharmaceutical composition suitable for delivery via an implantable medical device, and a pharmaceutical composition suitable for instillation via a instillation medical device.

### Claim 15 (depends on 1)

The method of claim 1, wherein the carboxyalkyl chitosan is instilled or injected via an intra-articular route.

### Claim 16 (depends on 1)

The method of claim 1, wherein said carboxyalkyl chitosan is water-soluble at a pH in a range of 3.1 to 9.

### Claim 17 (depends on 7)

The method of claim 7, wherein the carboxyalkyl chitosan is water-soluble at least in the pH range of 3.1 to 9.

### Claim 18 (depends on 8)

The method of claim 8, wherein said carboxyalkyl chitosan is soluble at a pH in a range of 3.1 to 9.

### Claim 19 (depends on 18)

The method of claim 18, wherein said aqueous solution further comprises hyaluronic acid or sodium hyaluronate, either crosslinked or not crosslinked by covalent bonds.

### Claim 20 (depends on 11)

The method of claim 11, wherein said carboxyalkyl chitosan is soluble at a pH in a range of 3.1 to 9.

### Claim 21 (depends on 12)

The method of claim 12, wherein said carboxyalkyl chitosan is soluble at a pH in a range of 3.1 to 9.

### Claim 22 (depends on 2)

The method of claim 2, wherein said carboxyalkyl chitosan is soluble at a pH in a range of 3.1 to 9.

### Claim 23 (depends on 22)

The method of claim 22, wherein said carboxyalkyl chitosan is administered via injection into the synovial fluid after mixing with blood.

### Claim 24 (depends on 22)

The method of claim 22, wherein said carboxyalkyl chitosan is administered via implantation into the cartilage.