# US 10,500,225 B2 · Injectable composition; method for preparing said composition; use of said composition

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- Number: US 10,500,225 B2
- Document ID: US10500225B2
- Status: Granted
- Kind: B2
- Application number: 15/781,485
- Filed: 2016-09-26
- Published: 2018-11-08
- Granted: 2019-12-10
- Earliest claimed: 2015-12-07
- Assignees: Kh Medtech SáRl
- Applicants: Kh Medtech Sarl
- Inventors: Benedicte Vincente Tauzin
- Web page: https://patentgrep.com/patent/US10500225B2

## CPC

- A61K 31/728: Hyaluronic acid
- 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 9/127: Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K 31/19: Carboxylic acids, e.g. valproic acid (salicylic acid A61K31/60)
- A61K 31/20: having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61L 2/04: Heat (radiation A61L2/08)
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 41/00: Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
- B65B 3/003: {Filling medical containers such as ampoules, vials, syringes or the like}
- B65B 55/02: Sterilising, e.g. of complete packages
- A61L 2103/05: Living organisms or biological materials
- A61L 2103/23: {Containers other than laboratory or medical, e.g. bottles or mail}
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- B65B: MACHINES, APPARATUS OR DEVICES FOR, OR METHODS OF, PACKAGING ARTICLES OR MATERIALS; UNPACKING (bundling and pressing devices for cigars A24C1/44; devices for tensioning and securing binders adapted to be supported by the article or articles to be bound B25B25/00; applying closure members to bottles, jars or similar containers B67B1/00-B67B6/00; concurrent cleaning, filling and closing of bottles B67C7/00; emptying bottles, jars, cans, casks, barrels or similar containers B67C9/00)

## Abstract

The present invention concerns a novel, sterile and injectable aqueous composition, that is heat-sterilised, comprising at least crosslinked hyaluronic acid, or one of the salts of same, and one or more fatty acids, characterised in that the mass proportion of water is greater than 51% of the total mass, the mass proportion of fatty acid is less than 45% of the total mass, the viscoelasticity properties are such that the ratio G″/G′ at 0.7 Hz is less than 0.70; a method for preparing said composition; and the use of said composition for aesthetic and therapeutic applications.

## Claims

### Claim 1

A sterile injectable hydrogel composition, sterilized by autoclaving, comprising at least cross-linked hyaluronic acid, or a salt thereof, and one or more fatty acids, wherein:
a) the mass proportion of water is greater than 51% of the total mass;
b) the mass proportion of fatty acid is less than 18% of the total mass and the total concentration of fatty acid is greater than 0.0001 mg/ml; and
c) the viscoelastic properties are such that the ratio G″/G′ at 0.7 Hz is less than 0.70, wherein the fatty acid molecules are dispersed in the hydrogel of said cross-linked hyaluronic acid in a homogeneous manner.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the hyaluronic acid or a salt thereof is sodium hyaluronate.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the hyaluronic acid or a salt thereof is cross-linked using a bi- or poly-functional cross-linker.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the hyaluronic acid or a salt thereof is cross-linked using 1,4-butanediol diglycidyl ether (BDDE).

### Claim 5 (depends on 1)

The composition of claim 1, wherein the total concentration of hyaluronic acid or a salt thereof is between 9 and 30 mg/ml.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the mass proportion of water is greater than 80% of the total mass.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the mass proportion of water is greater than 85% of the total mass.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the fatty acid(s) is/are selected from the group consisting of butyric acid, caproic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid, palmitoleic acid, oleic acid, linoleic acid, alpha-linoleic acid and arachidonic acid.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the total concentration of fatty acid is greater than 0.1 mg/ml.

### Claim 10 (depends on 1)

The composition of claim 1, wherein the composition contains liposomes or niosomes.

### Claim 11 (depends on 1)

The composition of claim 1, wherein at least a portion of the fatty acids is contained in liposomes or niosomes.

### Claim 12 (depends on 1)

The composition of claim 1, wherein the viscoelastic properties are such that the ratio G″/G′ at 0.7 Hz is less than 0.45.

### Claim 13 (depends on 1)

A method for preparing a sterile injectable hydrogel composition of claim 1, comprising at least cross-linked hyaluronic acid, or a salt thereof, and one or more fatty acids, the method comprising at least the following successive steps:
a) preparation of a hydrogel based on cross-linked hyaluronic acid, or a salt thereof;
b) addition of the fatty acid(s) to the hydrogel with a mixing operation, such that the fatty acid molecules are dispersed in the hydrogel of said cross-linked hyaluronic acid, in a homogeneous or relatively homogeneous manner; and
c) sterilization.

### Claim 14 (depends on 13)

The method for preparing a sterile injectable hydrogel composition comprising at least cross-linked hyaluronic acid, or a salt thereof, and one or more fatty acids, of claim 13, the method comprising at least the following successive steps:
preparation of an aqueous solution of hyaluronic acid;
cross-linking of the hyaluronic acid;
purification of the hydrogel;
addition of one or more fatty acids with a mixing operation;
packaging in syringes; and
sterilization.

### Claim 15 (depends on 1)

A method of aesthetically or therapeutically treating a patient comprising the administration of a composition of claim 1 to a patient in need of aesthetic or therapeutic treatment.

### Claim 16 (depends on 1)

The composition of claim 1, wherein the fatty acid is oleic acid.