COMPOSITION COMPRISING AT LEAST ONE C-GLYCOSIDE DERIVATIVE AND AT LEAST ONE HYALURONIC ACID AND ITS COSMETIC USE

• US 20090075935A1
• Filed: 08/15/2008
• Published: 03/19/2009
• Est. Priority Date: 07/03/2006
• Status: Abandoned Application

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: LABOUREAU, Julien, BISSEY, Laure, SAUSSAY, Sophie, SENEE, Jerome
• Application Number:
  US12/192,698
• Publication Number:
  US 20090075935A1
• Time in Patent Office: Days
• US Class Current: 514/54
• CPC Class Codes: A61K 8/602 Glycosides, e.g. rutin
• CPC Class Codes: A61K 8/735 Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
• CPC Class Codes: A61Q 19/08 Anti-ageing preparations

Abstract

The present invention relates to a topical cosmetic and/or dermatological composition comprising, in a physiologically acceptable medium, at least one hyaluronic acid or a derivative thereof and at least one C-glycoside derivative.

Claims

1-22. -22. (canceled)

23. A topical cosmetic and/or dermatological composition comprising, in a physiologically acceptable medium, at least one hyaluronic acid or a derivative thereof and at least one C-glycoside derivative.

24. The composition as claimed in claim 23, in which the hyaluronic acid or a derivative thereof has a molecular weight of between 50 000 and 5 000 000 Da.

25. The composition as claimed in claim 23 in which the hyaluronic acid or a derivative thereof has a molecular weight of between 100 000 and 5 000 000 Da.

26. The composition as claimed in claim 23 in which the hyaluronic acid or a derivative thereof has a molecular weight of between 400 000 and 5 000 000 Da.

27. The composition as claimed in claim 23, in which the hyaluronic acid or a derivative thereof is present at a content of between 0.001% and 20% by weight, of active material of hyaluronic acid or a derivative thereof, relative to the total weight of the composition.

28. The composition as claimed in claim 23, in which the hyaluronic acid or a derivative thereof is present at a content of between 0.01% and 10% by weight, of active material of hyaluronic acid or a derivative thereof, relative to the total weight of the composition.

29. The composition as claimed in claim 23, in which the hyaluronic acid or a derivative thereof is present at a content of between 0.01% and 5% by weight, of active material of hyaluronic acid or a derivative thereof, relative to the total weight of the composition.

30. The composition as claimed in claim 23, in which the C-glycoside derivative corresponds to general formula (I) below:

in which;

R represents;

a C₁ to C₂₀, saturated or C₂ to C₂₀, unsaturated, linear alkyl radical, or a C₃ to C₂₀, saturated or unsaturated, branched or cyclic alkyl radical;

a C₁ to C₂₀, saturated or C₂ to C₂₀, unsaturated, linear, or C₃ to C₂₀, saturated or unsaturated, branched or cyclic, hydrofluoro- or perfluoroalkyl radical;

it being possible for the hydrocarbon-based chain constituting said radicals to be, where appropriate, interrupted with 1, 2, 3 or more heteroatoms chosen from;

an oxygen,

a sulfur,

a nitrogen, and

a silicon,

and it being possible for it to be optionally substituted with at least one radical chosen from;

—

OR₄,

—

SR₄,

—

NR₄R₅,

—

COOR₄,

—

CONHR₄,

—

CN,

a halogen atom,

a C₁ to C₆ hydrofluoro- or perfluoroalkyl radical and/or

a C₃ to C₈ cycloalkyl radical,

with R₄ and R₅ possibly representing, independently of one another, a hydrogen atom, or a C₁ to C₃₀, saturated or C₂ to C₃₀, unsaturated, linear, or C₃ to C₃₀, saturated or unsaturated, branched or cyclic, alkyl, perfluoroalkyl or hydrofluoroalkyl radical;

or a C₆ to C₁₀ aryl radical,

X represents a radical chosen from the groups;

with R₁, R₇ and R₃ representing, independently of one another, a hydrogen atom, or a radical R, with R as defined above, and R′

¹ representing a hydrogen atom, an —

OH group or a radical R as defined above, R₁ also possibly denoting a C₆ to C₁₀ aryl radical;

S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in pyranose and/or furanose form of the L and/or D series, it being possible for said monosaccharide or polysaccharide to be substituted with a hydroxyl group which is necessarily free, and optionally one or more optionally protected amine function(s), and

the S—

CH₂—

X bond represents a bond of C-anomeric nature which may be a or P,

and also the cosmetically acceptable salts thereof, the solvates thereof, such as hydrates, and the isomers thereof.

31. The composition as claimed in claim 30, in which S represents a monosaccharide chosen from D-glucose, D-xylose, L-fucose, D-galactose and D-maltose.

32. The composition as claimed in claim 31, in which X represents a group chosen from —

CO—

, —

CH(OH)— and

—

CH(NH₂)—

.

33. The composition as claimed in claim 32, in which R denotes a C₁-C₄, in particular C₁-C₃, linear radical optionally substituted with —

OH, —

COOH or —

COOR″

₂, R″

2 being a C₁-C₄ saturated alkyl radical.

34. The composition as claimed in claim 23, in which the C-glycoside derivative is chosen from:

C-β

-D-xylopyranoside-n-propan-2-one,

C-α

-D-xylopyranoside-n-propan-2-one,

C-β

-D-xylopyranoside-2-hydroxypropane,

C-α

-D-xylopyranoside-2-hydroxypropane,

1-(C-β

-D-fucopyranoside)propan-2-one,

1-(C-α

-D-fucopyranoside)propan-2-one,

1-(C-β

-L-fucopyranoside)propan-2-one,

1-(C-α

-L-fucopyranoside)propan-2-one,

1-(C-β

-D-fucopyranoside)-2-hydroxypropane,

1-(C-α

-D-fucopyranoside)-2-hydroxypropane,

1-(C-β

-L-fucopyranoside)-2-hydroxypropane,

1-(C-α

-L-fucopyranoside)-2-hydroxypropane,

1-(C-β

-D-glucopyranosyl)-2-hydroxypropane,

1-(C-α

-D-glucopyranosyl)-2-hydroxypropane,

1-(C-β

-D-galactopyranosyl)-2-hydroxypropane,

1-(C-α

-D-galactopyranosyl)-2-hydroxypropane,

1-(C-β

-D-fucofuranosylpropan-2-one,

1-(C-α

-D-fucofuranosyl)propan-2-one,

1-(C-β

-L-fucofuranosyl)propan-2-one,

1-(C-α

-L-fucofuranosyl)propan-2-one,

C-β

-D-maltopyranoside-n-propan-2-one,

C-α

-D-maltopyranoside-n-propan-2-one,

C-β

-D-maltopyranoside-2-hydroxypropane,

C-α

-D-maltopyranoside-2-hydroxypropane, isomers thereof and mixtures thereof.

35. The composition as claimed in claim 23, in which the C-glycoside derivative is chosen from C-β

-D-xylopyranoside-2-hydroxypropane and C-α

-D-xylopyranoside-2-hydroxypropane.

36. The composition as claimed in claim 23, wherein the C-glycoside derivative is present at a content ranging from 0.0001% to 25% by weight of active material of C-glycoside derivative, relative to the total weight of the composition.

37. The composition as claimed in claim 23, wherein the C-glycoside derivative is present at a content ranging from 0.001% to 10% by weight of active material of C-glycoside derivative, relative to the total weight of the composition.

38. The composition as claimed in claim 23, wherein the C-glycoside derivative is present at a content ranging from 0.05% to 5% by weight of active material of C-glycoside derivative, relative to the total weight of the composition.

39. The composition as claimed in claim 23, in which the ratio by weight of the hyaluronic acid or a derivative thereof to the C-glycoside derivative ranges between 0.001 and 1000.

40. The composition as claimed in claim 23, in which the ratio by weight of the hyaluronic acid or a derivative thereof to the C-glycoside derivative ranges between 1 and 10.

41. The composition as claimed in claim 23, in which the ratio by weight of the hyaluronic acid or a derivative thereof to the C-glycoside derivative ranges between 2 and 4.

43. Method for using a cosmetic composition as defined in claim 23 for improving and/or reinforcing the barrier function of the skin.

44. Method for using a cosmetic composition as defined in claim 23 for improving and/or reinforcing the protection of the skin against outside attacks.

45. Method for using a cosmetic composition as defined in claim 23 for improving the hydration of the skin and/or its appendages.

46. Method for using a composition as defined in claim 23 for preventing and/or treating the roughness or the microrelief of the skin and/or its appendages and/or for improving the radiance of the complexion and/or for improving the suppleness of the skin and/or its appendages.

47. Method for using a cosmetic composition as defined in claim 23 for smoothing out the signs of skin aging.

48. Method as claimed in the claim 47, wherein the signs of skin aging are chosen from impairment of the viscoelastic or biomechanical properties of the skin, impairment of tissue cohesion, thinning of the skin, the appearance of wrinkles and/or fine lines, the appearance of browning and/or of yellowing of the skin and the appearance of age or senescence or lentigo spots.

42. A cosmetic assembly comprising:

a composition A comprising at least one C-glycoside derivative,

a composition B comprising at least one hyaluronic acid derivative or a derivative thereof.

50. A cosmetic treatment process comprising at least one step of applying composition A as defined in claim 42 to the skin and/or its appendages and at least one step of applying composition B as defined in claim 42 to the skin and/or its appendages.

49. A cosmetic treatment process for improving and/or reinforcing the barrier function and/or the hydration and/or the resistance to outside attacks of the skin and/or its appendages, and/or for combating the signs of skin aging, and wherein an effective amount of at least one C-glycoside derivative and of at least one hyaluronic acid or a derivative thereof is applied to the skin and/or its appendages.

51. Method of using at least one hyaluronic acid or a derivative thereof and of at least one C-glycoside derivative, for the preparation of a topical dermatological composition for improving and/or reinforcing the barrier function of the skin.

52. Method for using at least one hyaluronic acid or a derivative thereof and of at least one C-glycoside derivative, for the preparation of a topical dermatological composition for improving and/or reinforcing the barrier function of damaged skin.

53. Method for using at least one hyaluronic acid or a derivative thereof and of at least one C-glycoside derivative, for the preparation of a topical dermatological composition for improving and/or reinforcing the barrier function of damaged skin requiring tissue repair and/or regeneration.