IP Library Granted Patent US 10,959,934
Granted Patent B2
US 10,959,934 · App. 16/453,808 · Granted Mar 30, 2021

Micro- or nanoparticular vesicles comprising crosslinked hyaluronic acid, compositions comprising the same and method for their use in skin care

Inventors: Claire Mallard (Mougins, FR); Yves Rival (Antibes, FR)
Assignee: GALDERMA HOLDING SA
A61K8/735A61K8/14A61K8/37A61Q19/08
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Quick Facts
Patent No.
US 10,959,934
App. No.
16/453,808
Granted
Mar 30, 2021
Kind
B2
Abstract

A micro- or nanoparticular vesicle comprises at least a crosslinked hyaluronic acid (HA), wherein the crosslinked hyaluronic acid is crosslinked by a chemical crosslinking agent, and wherein the degree of modification of said crosslinked hyaluronic acid with said chemical crosslinking agent is less than 1.9 mole %. Also disclosed are a method of manufacturing such vesicles, compositions comprising such vesicles and their uses.

Claims (27)

1. A micro- or nanoparticular vesicle comprising at least a crosslinked hyaluronic acid,

wherein:

(a) the micro- or nanoparticular vesicle is a multilamellar vesicle comprising concentric membranes, comprising at least one non-ionic surfactant of the sucrose ester type, comprising at least one chain arising from a linear or branched, saturated or unsaturated, optionally mono- or polyhydroxylated, C 12 to C 22 fatty acid;

(b) the crosslinked hyaluronic acid is crosslinked by a chemical crosslinking agent; has a degree of modification of the crosslinked hyaluronic acid with the chemical crosslinking agent that is less than 1.9 mole %; and is loaded onto the vesicle and/or into the vesicle at a concentration between 0.01% and 5% (w/w).

2. The micro- or nanoparticular vesicle according to claim 1 , wherein the degree of modification of the crosslinked hyaluronic acid with the chemical crosslinking agent is between 0.1 and 1.9 mole %.

3. The micro- or nanoparticular vesicle according to claim 1 , wherein the degree of modification of the crosslinked hyaluronic acid with the chemical crosslinking agent is about 1.0 mole %.

4. The micro- or nanoparticular vesicle according to claim 1 , wherein the chemical crosslinking agent is a bi- or polyfunctional crosslinking agent comprising two or more glycidyl ether functional groups.

5. The micro- or nanoparticular vesicle according to claim 1 , wherein the crosslinked hyaluronic acid is sodium hyaluronate crosspolymer-2.

6. The micro- or nanoparticular vesicle according to claim 1 , wherein the vesicle is prepared from the mixture of a monoester of polyoxyethylene fatty acids, cholesterol, and free fatty acids.

7. The micro- or nanoparticular vesicle according to claim 1 , wherein the crosslinked hyaluronic acid is loaded onto the vesicle and/or into the vesicle at a concentration of 0.175%, 0.35%, or 0.5% (w/w).

8. The micro- or nanoparticular vesicle according to claim 1 , wherein the crosslinked hyaluronic acid is loaded onto the micro- or nanoparticular vesicle.

9. The micro- or nanoparticular vesicle according to claim 1 , further comprising a non-crosslinked hyaluronic acid, wherein up to 50% by weight of the total hyaluronic acid in the vesicle is non-crosslinked.

10. A composition comprising a micro- or nanoparticular vesicle according to claim 1 , in a physiologically acceptable medium.

11. The composition according to claim 10 , wherein the concentration of the vesicle is between 0.1% and 10% by weight, relative to the total weight of the composition.

12. The composition according to claim 10 , wherein the concentration of the vesicle is about 1%, about 2%, or about 3% by weight, relative to the total weight of the composition.

13. The composition according to claim 10 , wherein the vesicles are cationic vesicles, non-ionic vesicles, or a combination thereof.

14. The composition according to claim 10 , wherein the composition is formulated for topical and/or parenteral application.

15. A method of manufacturing a micro- or nanoparticular vesicle, comprising:

(a) preparing a non-ionic surfactant phase containing the non-ionic surfactants;

(b) preparing an aqueous phase containing the crosslinked hyaluronic acid;

(c) mixing the aqueous phase into the non-ionic surfactant phase with a controlled stirring and heating mode to form a preparation containing the vesicles comprising surfactant bi-layers; and

(d) diluting the preparation containing the vesicles with water;

wherein:

(i) the micro- or nanoparticular vesicle is a multilamellar vesicle comprising concentric membranes, comprising at least one non-ionic surfactant of the sucrose ester type, comprising at least one chain arising from a linear or branched, saturated or unsaturated, optionally mono- or polyhydroxylated, C 12 to C 22 fatty acid;

(ii) the crosslinked hyaluronic acid is crosslinked by a chemical crosslinking agent; has a degree of modification of the crosslinked hyaluronic acid with the chemical crosslinking agent that is less than 1.9 mole %; and is loaded onto the vesicle and/or into the vesicle at a concentration between 0.01% and 5% (w/w).

16. The method according to claim 15 , wherein the crosslinked hyaluronic acid is loaded onto the vesicles.

17. A method of caring for skin or reducing the effects of skin ageing, comprising topically applying a composition according to claim 10 to the skin of a human subject in need thereof.

Assignments (3)
CHANGE OF ADDRESS Recorded Jun 28, 2022
From: GALDERMA HOLDING SA
To: GALDERMA HOLDING SA
Reel/Frame 060541/0374 →
CHANGE OF NAME Recorded Dec 31, 2020
From: NESTLÉ SKIN HEALTH S.A.
To: GALDERMA HOLDING SA
Reel/Frame 054899/0803 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 11, 2020
From: MALLARD, CLAIRE; RIVAL, YVES
To: NESTLÉ SKIN HEALTH S.A.
Reel/Frame 052902/0080 →
Priority Claims (1)
EP 16306846 · Dec 29, 2016 · regional
Continuity (2)
Continuation PCTEP2017084760 · Dec 28, 2017
Related Publication 20190314262A1 · Oct 17, 2019