USE OF C-GLYCOSIDE DERIVATIVES AS PRO-DESQUAMATING ACTIVE AGENTS

• US 20100003236A1
• Filed: 06/29/2007
• Published: 01/07/2010
• Est. Priority Date: 07/03/2006
• Status: Active Grant

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Boulle, Christophe, Dalko, Maria, Bernard, Dominique
• Granted Patent: US 9,421,157 B2
• Time in Patent Office: Days
• US Class Current: 424/94.61
• CPC Class Codes: A61K 2800/28 Rubbing or scrubbing compositions; Peeling or abrasive compositions; Containing exfoliants
• CPC Class Codes: A61K 2800/88 Two- or multipart kits
• CPC Class Codes: A61K 8/602 Glycosides, e.g. rutin
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 17/12 Keratolytics, e.g. wart or anti-corn preparations
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 19/008 Preparations for oily skin
• CPC Class Codes: A61Q 5/006 Antidandruff preparations

Abstract

A cosmetic use of at least one C-glycoside derivative in a composition comprising a physiologically acceptable medium, as a cosmetic agent for promoting the desquamation of the skin and/or the scalp and/or for stimulating epidermal renewal.

Claims

1-19. -19. (canceled)

20. A cosmetic method for promoting desquamation of the skin and/or the scalp and/or for stimulating epidermal renewal comprising at least the use as a cosmetic agent of at least one C-glycoside derivative in a composition comprising a physiologically acceptable medium.

21. The method according to claim 20 wherein the said composition is directed towards combating keratosis and imperfections of acne-prone greasy skin, for combating the formation of dandruff, for homogenizing the skin relief, for removing surface roughness to afford a smoothing effect, for reducing surface irregularities and the skin'"'"'s microrelief, for improving the radiance of the complexion, for improving the staying power of makeup, for improving the efficacy of peeling treatments, or for preparing the skin before the application of a self-tanning agent and/or for improving the result of a skin treatment with stratum corneum colorants.

23. The method according to claim 20, wherein the composition is intended for preventing and/or treating skin and/or scalp disorders linked to deregulation of desquamation associated with the production of a thick horny layer and/or with abnormal desquamation.

24. The method according to claim 20, wherein the said composition is directed towards preventing and/or treating xerosis, acne, hyperkeratosis, psoriasis, atopy, ichthyosis and certain benign or malignant tumour lesions.

25. The method according to claim 20, in which the C-glycoside derivative corresponds to the general formula (I) below:

in which;

R represents;

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

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

the hydrocarbon-based chain constituting the said radicals possibly being,

where appropriate, interrupted with 1, 2, 3 or more heteroatoms chosen from;

an oxygen,

a sulfur,

a nitrogen, and

a silicon,

and possibly being optionally substituted with at least one radical chosen from;

—

OR₄,

—

SR₄,

—

NR₄R₅,

—

COOR₄,

—

CONHR₄,

—

CN,

a halogen atom,

a C₁-C₆ hydrofluoroalkyl or perfluoroalkyl radical, and/or

a C₃-C₈ cycloalkyl radical,

with R₄ and R₅ possibly representing, independently of each other, a hydrogen atom or a saturated C₁-C₃₀ or unsaturated C₂-C₃₀ linear—

, or a saturated or unsaturated, branched or cyclic C₃-C₃₀ alkyl, perfluoroalkyl or hydrofluoroalkyl radical;

or a C₆-C₁₀ aryl radical,

X represents a radical chosen from the groups;

with R₁, R₂ and R₃ representing, independently of each other, a hydrogen atom or a radical R, with R as defined above, and R′

₁ represents a hydrogen atom, an —

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

S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in pyranose and/or furanose form and of L and/or D series, the said mono- or polysaccharide possibly being substituted with a mandatorily free hydroxyl group, and optionally one or more optionally protected amine function(s), and

the bond S—

CH₂—

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

and also the cosmetically acceptable salts thereof, the solvates thereof and the isomers thereof.

26. The method according to claim 25, in which S represents a monosaccharide chosen from D-glucose, D-xylose, L-fucose, D-galactose and D-maltose.

27. The method according to claim 25, in which X represents a group chosen from —

CO—

, —

CH(OH)— and

—

CH(NH₂)—

.

28. The method according to claim 25, in which R denotes a linear C₁-C₄ radical, optionally substituted with —

OH, —

COOH or —

COOR″

₂, R″

₂ being a saturated C₁-C₄ alkyl radical.

29. The method according to claim 20, 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,

one exogenous protease and/or glycosidase and/or lipase,

one active agent for improving epidermal differentiation, and/or

one anti-seborrhoeic agent.

22. A method for preventing and/or treating signs associated with desquamation disorders comprising the use of at least one C-glycoside derivative.

33. Cosmetic treatment process for promoting desquamation and/or stimulating epidermal renewal, comprising at least the application to the skin and/or the scalp of a composition comprising, in a physiologically acceptable medium, at least one C-glycoside derivative.

34. Cosmetic treatment process for promoting the radiance of the complexion and/or for reducing surface irregularities of the skin and/or mucous membranes, comprising at least the application to the skin or the mucous membranes of at least one C-glycoside derivative, or a composition containing it.

35. Cosmetic process for treating keratin materials, consisting in applying at least two components:

a first component comprising at least one C-glycoside derivative or a composition containing it,

a second component comprising at least one agent chosen from proteases, lipases and glycosidases,

these two components being applied simultaneously, in combination or sequentially to the skin, mucous membranes or the scalp.

36. A method to promote regular desquamation of reconstructed skin comprising at least the use of at least one C-glycoside derivative.