WO2008004164A2 - Cosmetic and/or dermatological composition combining a c-glycoside derivative and a desquamating agent - Google Patents

Cosmetic and/or dermatological composition combining a c-glycoside derivative and a desquamating agent Download PDF

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Publication number
WO2008004164A2
WO2008004164A2 PCT/IB2007/052526 IB2007052526W WO2008004164A2 WO 2008004164 A2 WO2008004164 A2 WO 2008004164A2 IB 2007052526 W IB2007052526 W IB 2007052526W WO 2008004164 A2 WO2008004164 A2 WO 2008004164A2
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Prior art keywords
skin
acid
composition
fucopyranoside
propan
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PCT/IB2007/052526
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French (fr)
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WO2008004164A3 (en
Inventor
Béatrice Renault
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L'oreal
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Priority claimed from FR0606035A external-priority patent/FR2903009B1/en
Application filed by L'oreal filed Critical L'oreal
Publication of WO2008004164A2 publication Critical patent/WO2008004164A2/en
Publication of WO2008004164A3 publication Critical patent/WO2008004164A3/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/602Glycosides, e.g. rutin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/08Anti-ageing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/006Antidandruff preparations

Definitions

  • Cosmetic and/or dermatological composition combining a C-glycoside derivative and a desquamating agent
  • the present invention relates to a cosmetic and/or dermatological composition that is useful especially for promoting desquamation of the skin and/or the scalp and/or for stimulating epidermal renewal, comprising a combination of at least one desquamating agent in a content ranging from 0.001% to 95% by weight relative to the total weight of the composition and of at least one C-glycoside derivative as defined below.
  • keratin materials and/or fibres are understood to denote, for example, the skin, mucous membranes, the scalp, the eyelashes, the eyebrows and the hair.
  • skin is understood in its broad sense to be the skin and semi- mucous membranes (lips). Desquamation is a natural phenomenon associated with the fact that the epidermis, which constitutes the upper layer of the skin, is in constant regeneration.
  • the epidermis consists of several layers of cells, the deepest of which is the basal layer consisting of undifferentiated cells. Over time, these cells differentiate and migrate towards the surface of the epidermis, forming the various layers thereof, until they form at the surface of the epidermis the corneocytes, which are dead cells that become removed by desquamation. This surface loss is compensated for by the migration of cells from the basal layer to the surface of the epidermis. This constitutes a perpetual renewal of the skin. Forced removal of the horny layer accelerates the renewal and makes it possible to combat ageing. At the same time, these cells continue their differentiation, the final stage of which is the corneocyte. Corneocytes are in effect dead cells that constitute the last layer of the epidermis, i.e. the outermost layer also known as the stratum corneum.
  • the desquamation process may be impaired by exogenous factors (e.g.: UV radiation, pollution, allergens or pathogens) and/or endogenous factors (e.g.: hormonal changes, age, etc.) and especially lead to a slowing-down of epidermal renewal and consequently to ageing of the skin and/or thickening of the horny layer (e.g.: formation of calluses), and/or desquamative disorders of aesthetic type (e.g.: dandruff, squamae, etc.) or of pathological type (e.g.: xerosis, ichthyosis, psoriasis or atopic dermatitis).
  • exogenous factors e.g.: UV radiation, pollution, allergens or pathogens
  • endogenous factors e.g.: hormonal changes, age, etc.
  • desquamative disorders of aesthetic type e.g.: dandruff, squamae, etc.
  • ageing of the skin resulting from intrinsic or extrinsic factors, it is generally reflected by the appearance of wrinkles and fine lines, by yellowing of the skin, which develops a weathered appearance accompanied by the appearance of pigmentation marks, by deorganization of the elastin and collagen fibres, resulting in a loss of elasticity, suppleness and firmness, or by the appearance of telangiectasias.
  • Some of these signs of ageing are more particularly associated with intrinsic or physiological ageing, i.e. "normal” age-related or chronobio logical ageing, whereas others are more specific for extrinsic ageing, i.e. ageing caused in general by the environment; this may more particularly be photo-ageing due to exposure to sunlight, to light or to any other radiation.
  • the changes in the skin caused by intrinsic ageing are the consequence of a genetically programmed senescence involving endogenous factors.
  • This intrinsic ageing especially causes a slowing-down in the renewal of the skin cells, which is reflected essentially by the appearance of clinical impairments such as a reduction in the subcutaneous adipose tissue and the appearance of fine lines or wrinkles, and by histopathological changes such as an increase in the number and thickness of elastic fibres, a loss of vertical fibres from the elastic tissue membrane, and the presence of large, irregular fibroblasts in the cells of this elastic tissue.
  • extrinsic ageing results in clinical impairments such as large wrinkles and formation of a flaccid, tanned skin, and histopathological changes such as an excessive accumulation of elastic matter in the upper dermis and degeneration of the collagen fibres.
  • the invention is especially focused on intrinsic or physiological ageing and also extrinsic ageing.
  • agents for combating ageing of the skin are known in the prior art, among which are antioxidants, agents for promoting the proliferation and/or differentiation of dermal and/or epidermal cells, agents for stimulating the expression of dermal or epidermal macromolecules, that is to say as many agents as there are cellular or molecular targets in the skin for preventing and/or reducing the manifold effects of ageing of the skin.
  • patent US-A-4 603 146 describes the use of retinoic acid and derivatives thereof in cosmetic compositions, for combating ageing of the skin. Desquamating agents are also added to these agents for combating ageing of the skin.
  • the desquamating agents act by facilitating the removal of the dead cells located at the surface of the horny layer of the epidermis. This "desquamating" property is also referred to, often incorrectly, as a keratolytic property. Unfortunately, certain desquamating compounds may also have, when they are used at high concentration, side effects such as cutaneous discomfort.
  • C-Glycoside derivatives are especially described in document WO 02/051 828 for their properties on the synthesis of glycosaminoglycans (GAGs) and in particular for improving the moisturization and suppleness of the skin.
  • GAGs glycosaminoglycans
  • the invention relates to a cosmetic and/or dermatological composition
  • a cosmetic and/or dermatological composition comprising, in a physiologically acceptable medium: from 0.001% to 95% by weight, relative to the total weight of the composition, of at least one desquamating agent, and at least one C-glycoside derivative corresponding to the general formula (I) below:
  • - R denotes a linear Ci -C 4 and especially C 1 -C 3 alkyl radical, optionally substituted with -OH, -COOH or -COOR" 2 , R" 2 being a saturated Ci-C 4 alkyl radical, especially ethyl;
  • S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units and in particular up to 6 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 hydroxy 1 group, and optionally one or more optionally protected amine f ⁇ mction(s); and
  • X represents a group chosen from -CO-, -CH(OH)-, -CH(NH 2 )-, -CH(NHCH 2 CH 2 CH 2 OH)-, -CH(NHPh)- and -CH(CH 3 )-, and more particularly a -CO-, -CH(OH)- or -CH(NH 2 )- group, and preferentially a -CH(OH)- group;
  • the bond S-CH 2 -X represents a bond of C-anomeric nature, which may be ⁇ or ⁇ , and also the cosmetically acceptable salts thereof, the solvates thereof such as hydrates, and the isomers thereof.
  • a subject of the invention is the cosmetic use of at least one composition according to the invention for promoting desquamating of the skin and/or the scalp and/or for stimulating epidermal renewal, and especially for preventing, attenuating and/or combating the signs of ageing of the skin, for improving the appearance and/or texture of the skin and/or the scalp, and especially for improving the radiance and homogeneity of the complexion and/or for making the skin smooth, reducing the surface irregularities and the skin's microrelief, promoting the cleansing action and the removal of dead cells at the surface of the body, promoting the removal of dandruff, combating imperfections of greasy skin, improving the staying power of makeup and/or improving the result of treating the skin with stratum corneum colorants such as dihydroxyacetone (DHA).
  • DHA dihydroxyacetone
  • the invention also relates to the use of at least one desquamating agent in combination with at least one C-glycoside derivative according to the invention for the preparation of a composition for treating certain skin pathologies associated with abnormal desquamation, such as xerosis, ichthyosis, psoriasis and atopic dermatitis.
  • a subject of the invention is also a cosmetic treatment process for the non- therapeutic care of the skin and/or the scalp, characterized in that it comprises the simultaneous or sequential application to the skin, via at least one composition, of at least one C-glycoside derivative and of at least one desquamating agent according to the invention.
  • the cosmetic treatment process according to the invention may comprise at least one step that consists in applying a cosmetic composition according to the present invention to the skin and/or the scalp.
  • the cosmetic treatment process for the non-therapeutic care of the skin and/or the scalp according to the invention is more particularly a process for promoting the desquamation of the skin and/or the scalp, and/or for stimulating epidermal renewal, and especially for preventing, attenuating and/or combating the signs of ageing of the skin, for improving the appearance and/or texture of the skin and/or the scalp, and especially for improving the radiance and homogeneity of the complexion and/or for making the skin smooth, for reducing the surface irregularities and the skin's microrelief, for promoting the cleansing action and the removal of dead cells at the surface of the body, for promoting the removal of dandruff, for improving the staying power of makeup and/or for improving the result of treating the skin with stratum corneum colorants such as dihydroxy acetone (DHA).
  • DHA dihydroxy acetone
  • the C-glycoside derivative and the desquamating agent may be conditioned in two different compositions.
  • the improvement in the staying power of makeup and/or of skin colouring treatments with DHA results from the fact that the skin and/or the scalp may be prepared before the abovementioned makeup and/or colouring operations by the application of a composition according to the invention, which will promote the result of a simultaneous or subsequent treatment with a makeup agent and/or a colouring agent.
  • signal of ageing of the skin means any change in the outer appearance of the skin and/or in its texture due to chronological or photo-induced ageing, for instance wrinkles, fine lines, wizened skin, flaccid skin, thinned skin and lack of elasticity or tonus of the skin.
  • the pro-desquamating activity is effectively sought mainly in the field of "anti- ageing" compositions, i.e. compositions for combating the cutaneous signs caused by ageing and/or photo-ageing.
  • the combination used according to the present invention may also find applications in attenuating surface irregularities of the skin and in improving the skin's microrelief, in particular attenuating actinic lentigo and acne or chickenpox scars, and unblocking skin pores; treating dry skin and acne-prone greasy skin. As regards greasy skin, this is often associated with a desquamation defect, and with a thick skin grain.
  • the excess sebum may serve as a support for the anarchic growth of saprophytic bacterial flora (in particular Propionibacterium acnes and Pityrosporum ovale), and cause the appearance of comedones and/or acne scars.
  • saprophytic bacterial flora in particular Propionibacterium acnes and Pityrosporum ovale
  • acne scars are another cutaneous sign of greasy skin that may advantageously be combated by means of the use of at least one composition according to the present invention.
  • the combination of a desquamating agent and of a C-glycoside derivative or the composition according to the invention may be applied to any area of skin or of its appendages, especially of the face, the neckline or the hands, or the lips, in order to attenuate the visible and/or tactile irregularities of the skin, for example for attenuating scars and for making the surface smooth and/or removing dead skin, especially from the lips.
  • the C-glycoside derivative and the desquamating agent that are the subject of the combination according to the invention may be conditioned in two different compositions and applied simultaneously or sequentially.
  • composition comprising the C-glycoside may be applied to prepare the skin for the subsequent application of the desquamating agent.
  • the combination and the compositions in accordance with the invention make it possible to promote desquamation of the skin and/or to stimulate epidermal renewal and thus, more particularly, to treat skin and/or scalp pathologies that are characterized by the production of a thickened horny layer and/or by abnormal desquamation.
  • the present invention also relates to the use of the combination or of a composition according to the invention for the preparation of a composition for treating skin and/or scalp pathologies characterized by the production of a thickened horny layer and/or by abnormal desquamation.
  • the combination of at least one desquamating agent and of at least one C-glycoside derivative or of a composition according to the invention makes it possible to promote the desquamation of the skin and/or the scalp and/or to stimulate epidermal renewal and may thus be used for the preparation of a dermatological composition for treating the abovementioned skin pathologies that are characterized by the production of a thickened horny layer and/or by abnormal desquamation.
  • the composition according to the present invention finds another application in the field of chemical peeling treatments. The combination according to the invention is thus advantageous in peeling compositions.
  • Peeling treatments are a well-known means for improving the appearance and/or texture of the skin and/or the scalp, and especially for improving the radiance and homogeneity of the complexion and/or for reducing the visible and/or tactile irregularities of the skin, and in particular for improving the surface appearance of the skin, for attenuating actinic lentigo and acne or chickenpox scars, and also for preventing, attenuating or combating the signs of ageing of the skin, and especially for smoothing out skin texture irregularities, such as wrinkles and fine lines. They have the effect of removing a surface portion of the skin to be treated
  • a subject of the invention is thus a cosmestic process for treating the visible and/or tactile irregularities of human skin, comprising the steps consisting in: a) applying topically to the skin a composition according to the present invention, b) leaving the composition in contact with the skin for a period of between 5 minutes and 6 hours and preferably between 5 minutes and 30 minutes, and c) removing the composition by rinsing.
  • the invention relates to a cosmetic process for promoting the desquamation of the skin and/or mucous membranes, comprising at least one step (i) of preparing the skin for peeling, which consists in applying to the areas to be treated at least one C-glycoside derivative as defined hereinbelow, at least at a concentration below that resulting from desquamation, and (ii) a subsequent step comprising application of at least one desquamating agent at a concentration suitable for causing desquamation. A step for removing the desquamating agent(s) by rinsing will then be performed.
  • step (i) may be repeated with increasing concentrations of C-glycoside derivative.
  • concentrations will be adapted by a person skilled in the art as a function of the desired effect and of the envisaged number of applications, but will generally be less than 10%. It will be possible, for example, to use a first concentration of about 2%, followed by one or more successive applications with a concentration of about 4%, and then 6% or 8% by weight.
  • This process is more particularly intended for preventing, attenuating and/or combating the signs of ageing of the skin, and especially for attenuating wrinkles and fine lines, and for improving the appearance and/or texture of the skin, in particular for improving the homogeneity of the complexion and/or for making the skin smooth, and especially for attenuating actinic lentigo or acne or chickenpox scars, and/or for deblocking the skin pores.
  • the term "desquamating agent” means any compound capable of acting: either directly on desquamation by promoting exfoliation, such as: saturated and unsaturated monocarboxylic acids, saturated and unsaturated dicarboxylic acids, saturated and unsaturated tricarboxylic acids; ⁇ -hydroxy acids and ⁇ -hydroxy acids of monocarboxylic acids; ⁇ -hydroxy acids and ⁇ -hydroxy acids of dicarboxylic acids; ⁇ -hydroxy acids and ⁇ -hydroxy acids of tricarboxylic acids; keto acids, ⁇ -keto acids or ⁇ -keto acids of polycarboxylic acids, of polyhydroxymonocarboxylic acids, of polyhydroxydicarboxylic acids or of polyhydroxytricarboxylic acids; and (3-hydroxy- 2-pentylcyclopentyl)acetic acid.
  • Preferred ⁇ -hydroxy acids include: gly colic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid.
  • Preferred ⁇ -hydroxy acids are chosen from: salicylic acid and derivatives thereof, in particular 5-n-octanoylsalicylic acid.
  • exfo Hants include: pyruvic acid, gluconic acid, glucuronic acid, oxalic acid, malonic acid, succinic acid, acetic acid, gentisic acid, cinnamic acid, azelaic acid; phenol, resorcinol; urea and derivatives thereof; oligofucoses as in patent EP 0 218 200; jasmonic acid and derivatives thereof as in patent applications EP 1 333 022 and EP 1 333 021; trichloroacetic acid; retinoids such as retinol or retinoic acid; adapalene; the extract of Saphora japonica; resveratrol; and also salts and derivatives thereof, such as the cis or trans forms, racemic mixtures and the dextrorotatory or laevorotatory forms of the abovementioned agents.
  • corneodesmosomes or on the enzymes involved in the desquamation or degradation of corneodesmosomes, such as glycosidases, stratum corneum chymotryptic enzyme (SCCE) or even other proteases (trypsin, chymotrypsin-like).
  • SCCE stratum corneum chymotryptic enzyme
  • trypsin, chymotrypsin-like enzymes involved in the desquamation or degradation of corneodesmosomes, such as glycosidases, stratum corneum chymotryptic enzyme (SCCE) or even other proteases (trypsin, chymotrypsin-like).
  • mineral salt chelating agents such as EDTA; N-acyl-N,N',N'-ethylenediaminetriacetic acid; amino sulfonic compounds and in particular (N-2-hydroxyethylpiperazine-N- 2-ethane)sulfonic acid (HEPES); 2-oxothiazolidine-4-carboxylic acid (procysteine) deriavtives; derivatives of ⁇ -amino acids of glycine type (as described in EP 0 852 949, and also sodium methyl glycine diacetate sold by BASF under the trade name TRILON M ® ); honey; sugar derivatives such as O-octanoyl-6-D-maltose, O-linoleyl-6-D- glucose and N-acetylglucosamine.
  • mineral salt chelating agents such as EDTA; N-acyl-N,N',N'-ethylenediaminetriacetic acid; amino sulfonic compounds and in
  • desquamating agents that may be used in the composition according to the invention, mention may be made of extracts of laminaria such as Laminaria saccharina and Laminaria ochrolenca, glyceryl trilactate, siliceous salicylate derivatives as in patent EP 0 796 861, 5-acylsalicylic acid salts, active agents with effects on transglutaminase as in patent EP 0 899 330, and an extract of Ficus opuntia indica blossom, such as Exfolactive ® from Silab.
  • laminaria such as Laminaria saccharina and Laminaria ochrolenca
  • glyceryl trilactate siliceous salicylate derivatives
  • 5-acylsalicylic acid salts active agents with effects on transglutaminase as in patent EP 0 899 330
  • an extract of Ficus opuntia indica blossom such as Exfolactive ® from Silab.
  • Preferred desquamating agents include ⁇ -hydroxy acids, such as 5-n-octanoylsalicylic acid; urea and derivatives thereof; glycolic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid; (N-2 hydroxyethylpiperazine-N- 2-ethane)sulfonic acid (HEPES); the extract of Saphora japonica; honey; N-acetylglucosamine; 2-oxothiazolidine-4-carboxylic acid (procysteine) derivatives, and mixtures thereof.
  • ⁇ -hydroxy acids such as 5-n-octanoylsalicylic acid; urea and derivatives thereof; glycolic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid; (N-2 hydroxyethylpiperazine-N- 2-ethane)sulfonic acid (HEPES); the extract of Saphora japonica; honey; N-acetyl
  • a desquamating agent chosen from glycolic acid, 5-n-octanoylsalicylic acid, (N-2-hydroxyethylpiperazine-N-2-ethane)sulfonic acid (HEPES) and 2-oxothiazolidine-4-carboxylic acid (procysteine) derivatives, and mixtures thereof, will be used in the composition of the invention.
  • a person skilled in the art will be able to define the necessary amount of desquamating agent present in the combination according to the invention in order to obtain the desired effect on the skin.
  • the desquamating agent may be in a content ranging from 0.001% to 95% by weight relative to the total weight of the composition, in particular from 0.01% to 30% by weight relative to the total weight of the composition and preferentially from 0.01% to 10% by weight relative to the total weight of the composition.
  • the composition may especially contain from
  • At least 10% by weight, in particular more than 20% by weight, especially from 21% to 50% and preferably from 21% to 30% by weight of desquamating agent, relative to the total weight of the composition, will be used in the peeling compositions.
  • C-GLYCOSIDE DERIVATIVES A C-glycoside derivative that is suitable for use in the invention is a compound of general formula (I) below:
  • - R denotes a linear Ci -C 4 and especially C 1 -C 3 alkyl radical, optionally substituted with -OH, -COOH or -COOR" 2 , R" 2 being a saturated Ci-C 4 alkyl radical, especially ethyl;
  • - S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units and in particular up to 6 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 hydroxy 1 group, and optionally one or more optionally protected amine function(s); and
  • X represents a group chosen from -CO-, -CH(OH)-, -CH(NH 2 )-, -CH(NHCH 2 CH 2 CH 2 OH)-, -CH(NHPh)- and -CH(CH 3 )-, and more particularly a -CO-, -CH(OH)- or -CH(NH 2 )- group, and preferentially a -CH(OH)- group;
  • the bond S-CH 2 -X represents a bond of C-anomeric nature, which may be ⁇ or ⁇ , and also the cosmetically acceptable salts thereof, the solvates thereof such as hydrates, and the isomers thereof.
  • alkyl groups that are suitable for use in the invention, mention may be made especially of methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, isobutyl, sec- butyl, pentyl, n-hexyl, cyclopropyl, cyclopentyl, cyclohexyl and allyl groups.
  • a monosaccharide of the invention may be chosen from D- glucose, D-galactose, D-mannose, D-xylose, D-lyxose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D- glucosamine and N-acetyl-D-galactosamine, and advantageously denotes D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D-xylose.
  • a polysaccharide of the invention containing up to 6 sugar units may be chosen from D-maltose, D-lactose, D-cellobiose, D-maltotriose, a disaccharide combining a uronic acid chosen from D-iduronic acid and D-glucuronic acid with a hexosamine chosen from D-galactosamine, D-glucosamine, N-acetyl-D- galactosamine and N-acetyl-D-glucosamine, an oligosaccharide containing at least one xylose advantageously chosen from xylobiose, methyl- ⁇ -xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and especially xylobiose, which is composed of two xylose molecules linked via a 1-4 bond.
  • S may represent a monosaccharide chosen from D-glucose, D-xylose, L-fucose, D-galactose and D-maltose, especially D-xylose.
  • R denotes an unsubstituted linear Ci -C 4 and especially Ci-C 2 alkyl radical, in particular ethyl;
  • S represents a monosaccharide as described above; especially D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, in particular D-xylose;
  • X represents a group chosen from -CO-, -CH(OH)- and -CH(NH 2 )- and preferentially a CH(OH)- group.
  • the salts that are acceptable for the non-therapeutic use of the compounds described in the present invention comprise conventional non-toxic salts of the said compounds such as those formed from organic or inorganic acids.
  • examples that may be mentioned include the salts of mineral acids, such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydriodic acid, phosphoric acid or boric acid.
  • neutralization of the acid group(s) may be performed with a mineral base, such as LiOH, NaOH, KOH, Ca(OH) 2 , NH 4 OH, Mg(OH) 2 or Zn(OH) 2 ; or with an organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine.
  • a mineral base such as LiOH, NaOH, KOH, Ca(OH) 2 , NH 4 OH, Mg(OH) 2 or Zn(OH) 2
  • organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine.
  • This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and/or oxygen atoms and may thus comprise, for example, one or more alcohol functions; mention may be made especially of amino-2-methyl-2-propanol, triethanolamine, dimethylamino-2-propanol or 2-amino-2-(hydroxymethyl)-l,3-propanediol. Mention may also be made of lysine or
  • solvates that are acceptable for the compounds described in the present invention comprise conventional solvates such as those formed during the final step of preparation of the said compounds due to the presence of solvents. Examples that may be mentioned include the solvates due to the presence of water or of linear or branched alcohols, for instance ethanol or isopropanol.
  • solvates due to the presence of water or of linear or branched alcohols for instance ethanol or isopropanol.
  • the ones that are most particularly considered are:
  • C-glycoside derivatives that are more particularly suitable for use in the invention, mention may be made especially of the following derivatives: C- ⁇ -D-xylopyranoside-n-propan-2-one,
  • C- ⁇ -D-xylopyranoside-2-hydroxypropane or C- ⁇ -D-xylopyranoside-2-hydroxypropane, and better still C- ⁇ -D-xylopyranoside- 2-hydroxypropane may advantageously be used for the preparation of a composition according to the invention.
  • the C-glycoside derivative may be
  • C- ⁇ -D-xylopyranoside-2-hydroxypropane which is in the form of a solution containing 30% by weight of active material in a water/propylene glycol mixture (60%/40% by weight) such as the product sold by CHIMEX under the trade name "Mexoryl SBB®".
  • a C-glycoside derivative corresponding to formula (I) may be used alone or as a mixture with other C-glycoside derivatives and in any proportion.
  • a C-glycoside derivative that is suitable for use in the invention may especially be obtained via the synthetic method described in document WO 02/051 828.
  • the amount of C-glycoside derivative to be used in a composition according to the invention depends on the desired cosmetic or therapeutic effect, and may thus vary within a wide range.
  • a composition according to the invention may comprise a C-glycoside derivative in a proportion of about from 0.0001% to about 25% by weight of active material relative to the total weight of the composition, in particular from about 0.001% to about 10% by weight of active material and more particularly from about 0.05% to about 5% by weight of C-glycoside derivative active material relative to the total weight of the composition.
  • the same contents may be envisaged in the corresponding compositions. It is also possible to use larger contents to further improve the desired desquamating effect and/or to reduce the content of desquamating agent in the combination according to the invention.
  • the mass ratio between the desquamating agent and the C-glycoside derivative may vary as a function of the intended galenical formulations and/or of the intended uses.
  • the mass ratio may especially range from 0.0004 to 900, or even from 0.004 to
  • 600 preferably from 0.01 to 300 and even more preferentially from 0.01 to 150, or even from 0.01 to 100.
  • the mass ratio between the desquamating agent and the C-glycoside derivative may especially range from 0.01 to 100, preferably from 0.01 to 60, more preferentially from 0.01 to 30 and even more preferentially from 0.01 to 10, from 0.01 to 5, or even from 0.02 to 2.
  • the mass ratio between the desquamating agent and the C-glycoside derivative may especially range from 1 to 300, preferably from 2 to 150 and even more preferentially from 2 to 100, or even from 2 to 50.
  • composition according to the present invention may also comprise at least one additional cosmetic and/or dermatological agent for improving the appearance and/or comfort of the skin and/or the scalp.
  • This additional agent may especially be an anti-ageing and/or anti-wrinkle agent.
  • the anti-ageing and/or anti-wrinkle agent may especially be chosen from: - an anti-glycation agent, such as an extract of blueberry (Vaccinium angustifolium), for example the product sold under the name "Blueberry Herbasol Extract PG" by the company Cosmetochem, an extract of black tea such as Kombuchka from Sederma, or lipoic acid or thioctic acid such as Nutralip® from Labochim; an NO-synthase inhibitor, such as extracts of Ginkgo biloba, of Vitis vinifera or of Olea europaea; an agent acting on dermal or epidermal macromolecules and/or preventing their degradation, such as extracts of Centella asiatica, asiaticosides and derivatives; ascorbic acid and derivatives thereof; synthetic peptides such as iamin, biopeptide CL or palmitoyl pentapeptide sold
  • additional anti-ageing agents are generally present in the cosmetic compositions at contents ranging from 0.01% to 20% by weight relative to the total weight of the composition, preferably from 0.01% to 10% by weight relative to the total weight of the composition and even more preferentially from 0.01% to 1% by weight relative to the total weight of the composition.
  • the invention thus also relates to a composition
  • a composition comprising: at least one C-glycoside derivative, at least one desquamating agent chosen from 5-n-octanoylsalicylic acid, (N-2-hydroxyethylpiperazine-N-2-ethane)sulfonic acid (HEPES), or an EDTA derivative, and mixtures thereof; and - at least one additional anti-ageing agent, and preferably at least two anti- ageing agents chosen from adenosine, an extract of malt, an extract of Padina pavonica, an extract of soybean and an extract of wild yam, and mixtures thereof.
  • HEPES N-2-hydroxyethylpiperazine-N-2-ethane)sulfonic acid
  • compositions according to the invention comprise a physiologically acceptable medium.
  • physiologically acceptable medium is intended to denote a medium which is compatible with human keratin materials and/or fibres, for instance, in a non-limiting manner, the skin, mucous membranes, the nails, the scalp and/or the hair.
  • This physiologically acceptable medium comprises water, optionally as a mixture with one or more organic solvents such as Ci-Cs alcohols, especially ethanol, isopropanol, tert-butanol or n-butanol, polyols, for instance glycerol, propylene glycol or butylene glycol and polyol ethers.
  • the compositions according to the invention may be a cosmetic or dermato logical composition and may thus comprise a cosmetically or pharmaceutically acceptable medium.
  • the composition may also comprise a fatty phase, which may comprise oils, gums or waxes usually used in the field of application under consideration.
  • oils or waxes that may be used in the invention, mention may be made of mineral oils (liquid petroleum jelly), plant oils (liquid fraction of shea butter, sunflower oil, apricot oil, rice bran oil, etc), animal oils (perhydrosqualene), synthetic oils (purcellin oil), silicone oils or waxes (cyclomethicone or dimethicone) and fluoro oils (perfluoropolyethers), beeswax, carnauba wax, paraffin wax, shea butter or hydrogenated jojoba oil.
  • Fatty alcohols cetyl alcohol, stearyl alcohol, etc
  • fatty acids stearic acid, etc
  • the proportion of the fatty phase may range from 5% to 80% by weight and preferably from 5% to 50% by weight relative to the total weight of the composition.
  • the oils, waxes, emulsifiers and coemulsifiers used in the composition in emulsion form are chosen from those conventionally used in cosmetics.
  • the emulsifier and the coemulsif ⁇ er are present in the composition in a proportion ranging from 0.3% to 30% by weight and preferably from 0.5 to 20% by weight relative to the total weight of the composition.
  • the emulsion may also contain lipid vesicles.
  • the fatty phase may represent more than 90% of the total weight of the composition.
  • the composition may also contain adjuvants that are common in the field under consideration, such as surfactants, emulsifiers, hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic additives, preserving agents, antioxidants, solvents, fragrances, fillers, screening agents, odour absorbers and dyestuffs, and other cosmetic or pharmaceutical active agents.
  • the amounts of these various adjuvants are those conventionally used in cosmetics, for example from 0.01% to 10% of the total weight of the composition.
  • these adjuvants may be introduced into the fatty phase, into the aqueous phase and/or into lipid spherules.
  • surfactants examples that may be mentioned include glyceryl stearate, polysorbate 60 and the mixture of PEG-6/PEG-32/glycol stearate sold under the name TefoseR 63 by the company Gattefosse; PEG stearate derivatives and sugar derivatives.
  • hydrophilic gelling agents that may be used in the invention, mention may be made of carboxyvinyl polymers (carbomer), acrylic copolymers such as acrylate/alkyl acrylate copolymers, polyacrylamides, polysaccharides such as hydroxypropylcellulose, natural gums and clays, and lipophilic gelling agents that may be mentioned include modified clays, for instance bentones, metal salts of fatty acids, for instance aluminium stearates, and hydrophobic silica, ethylcellulose or polyethylene.
  • the composition may be in any conceivable galenical form.
  • the composition may especially be in the form of an aqueous, alcoholic, aqueous-alcoholic or oily solution; a dispersion of the lotion or serum type; a water-in-oil, oil-in-water or multiple emulsion; a suspension; microcapsules or microparticles; vesicular dispersions of ionic and/or non- ionic type; an aqueous or oily lotion or a lotion in serum form; a mousse or a solid preparation, for example in stick form; an aerosol composition also comprising a pressurized propellant or in the form of a patch.
  • the composition according to the invention may be in the form of a haircare composition, especially a shampoo, a hairsetting lotion, a medicated lotion, a styling cream or gel, a dye composition, especially for oxidation dyeing, a hair restructuring lotion, a permanent-waving composition (especially a composition for the first stage of a permanent-waving operation), a lotion or gel for preventing hair loss, or an antiparasitic shampoo.
  • a haircare composition especially a shampoo, a hairsetting lotion, a medicated lotion, a styling cream or gel, a dye composition, especially for oxidation dyeing, a hair restructuring lotion, a permanent-waving composition (especially a composition for the first stage of a permanent-waving operation), a lotion or gel for preventing hair loss, or an antiparasitic shampoo.
  • a cleansing, protective, treating or care composition for the face, the hands, the feet, the major anatomical folds or the body
  • a cleansing, protective, treating or care composition for the face, the hands, the feet, the major anatomical folds or the body
  • a body or facial makeup composition such as a foundation
  • a bath composition for example, a deodorizing composition comprising, for example, a bactericidal agent; an aftershave composition; a hair-removing composition; an insect-repelling composition; a pain-relief composition; a composition for treating certain skin diseases, for instance eczema, rosacea, psoriasis, lichens or severe pruritus.
  • the composition according to the invention may also be in any of the galenical forms mentioned above, provided that it can be removed easily by rinsing, and especially in the form of an aqueous gel or an aqueous or aqueous-alcoholic solution. It may be applied via any means allowing uniform distribution and especially using cotton wool, a cotton tip, a brush, a gauze, a spatula or a pad, or alternatively by spraying, and may be removed by rinsing with water or using a mild detergent. According to one preferred embodiment of the invention, the composition intended for chemical peeling contains a continuous aqueous phase.
  • a subject of the present invention is also a composition for caring for the skin and/or the scalp, characterized in that the desquamating agent is chosen from ⁇ -hydroxy acids such as 5-n-octanoylsalicylic acid; urea and derivatives thereof; gly colic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid; (N-2-hydroxyethylpiperazine- N-2-ethane)sulfonic acid (HEPES); an extract of Saphora japonica; honey; N-acetylglucosamine and 2-oxothiazolidine-4-carboxylic acid (procysteine) derivatives, and extracts of laminaire such as Laminaria saccharina and Laminaria ochrolenca.
  • ⁇ -hydroxy acids such as 5-n-octanoylsalicylic acid; urea and derivatives thereof; gly colic acid, citric acid, lactic acid, tartaric acid, malic acid
  • a subject of the present invention is a peeling composition, characterized in that the desquamating agent is present in a content of greater than 20% by weight, for example ranging from 21% by weight to 70% by weight, especially from 21% to 50% and even more preferentially from 21% to 30% by weight relative to the total weight of the composition.
  • the C-glycoside derivative used is C- ⁇ -D-xylopyranoside-2-hydroxypropane, sold under the name MEXORYL ® by Chimex. It is in the form of a solution containing 30% by weight of active material in a 60/40 water/1, 2-propanediol mixture.
  • Example 1 Evaluation on reconstructed skin of the desquamating effect of a mixture between a desquamating agent and a C-glycoside derivative
  • the test uses a model of reconstructed skin: it consists in evaluating, by counting with a microscope, the number of corneocytes released after application of the desquamating product or of the desquamating mixture to be tested.
  • test products After culturing models of reconstructed skin, the test products are applied topically at various concentrations ranging from 0.01% to 50% to evaluate a dose effect.
  • the test products are: glycolic acid at concentrations ranging from 1% to 70% by weight of active material;
  • C- ⁇ -D-xylopyranoside-2-hydroxypropane as a solution at 30% by weight in a 60/40 water/propylene glycol mixture used at concentrations ranging from 0.01% to 10% by weight of active material; a mixture of 5-n-octanoylsalicylic acid and of C- ⁇ -D-xylopyranoside- 2-hydroxypropane as a solution at 30% by weight in a 60/40 water/propylene glycol mixture.
  • the negative blank consists of an equivalent volume of MiIIiQ water.
  • the positive blank is a 30% glycolic acid solution. Each condition is treated in triplicate.
  • the corneocytes released after the treatment are counted on glass slides.
  • AM active material The cream is applied daily to the skin of the face and/or the neck.
  • compositions are obtained that are pleasant to apply and that have desquamating properties, without, however, causing the user any sensations of stinging, tautness or heating.

Abstract

The present invention relates to a cosmetic and/or dermatological composition comprising, in a physiologically acceptable medium: from 0.001% to 95% by weight, relative to the total weight of the composition, of at least one desquamating agent, and at least one C-glycoside derivative.

Description

Cosmetic and/or dermatological composition combining a C-glycoside derivative and a desquamating agent
The present invention relates to a cosmetic and/or dermatological composition that is useful especially for promoting desquamation of the skin and/or the scalp and/or for stimulating epidermal renewal, comprising a combination of at least one desquamating agent in a content ranging from 0.001% to 95% by weight relative to the total weight of the composition and of at least one C-glycoside derivative as defined below.
It may especially be a composition for caring for and/or making up keratin materials and/or fibres. For the purposes of the invention, the term "keratin materials and/or fibres" is understood to denote, for example, the skin, mucous membranes, the scalp, the eyelashes, the eyebrows and the hair.
The term "skin" is understood in its broad sense to be the skin and semi- mucous membranes (lips). Desquamation is a natural phenomenon associated with the fact that the epidermis, which constitutes the upper layer of the skin, is in constant regeneration.
The epidermis consists of several layers of cells, the deepest of which is the basal layer consisting of undifferentiated cells. Over time, these cells differentiate and migrate towards the surface of the epidermis, forming the various layers thereof, until they form at the surface of the epidermis the corneocytes, which are dead cells that become removed by desquamation. This surface loss is compensated for by the migration of cells from the basal layer to the surface of the epidermis. This constitutes a perpetual renewal of the skin. Forced removal of the horny layer accelerates the renewal and makes it possible to combat ageing. At the same time, these cells continue their differentiation, the final stage of which is the corneocyte. Corneocytes are in effect dead cells that constitute the last layer of the epidermis, i.e. the outermost layer also known as the stratum corneum.
It is known that the desquamation process may be impaired by exogenous factors (e.g.: UV radiation, pollution, allergens or pathogens) and/or endogenous factors (e.g.: hormonal changes, age, etc.) and especially lead to a slowing-down of epidermal renewal and consequently to ageing of the skin and/or thickening of the horny layer (e.g.: formation of calluses), and/or desquamative disorders of aesthetic type (e.g.: dandruff, squamae, etc.) or of pathological type (e.g.: xerosis, ichthyosis, psoriasis or atopic dermatitis).
As more particularly regards ageing of the skin, resulting from intrinsic or extrinsic factors, it is generally reflected by the appearance of wrinkles and fine lines, by yellowing of the skin, which develops a weathered appearance accompanied by the appearance of pigmentation marks, by deorganization of the elastin and collagen fibres, resulting in a loss of elasticity, suppleness and firmness, or by the appearance of telangiectasias.
Some of these signs of ageing are more particularly associated with intrinsic or physiological ageing, i.e. "normal" age-related or chronobio logical ageing, whereas others are more specific for extrinsic ageing, i.e. ageing caused in general by the environment; this may more particularly be photo-ageing due to exposure to sunlight, to light or to any other radiation.
The changes in the skin caused by intrinsic ageing are the consequence of a genetically programmed senescence involving endogenous factors. This intrinsic ageing especially causes a slowing-down in the renewal of the skin cells, which is reflected essentially by the appearance of clinical impairments such as a reduction in the subcutaneous adipose tissue and the appearance of fine lines or wrinkles, and by histopathological changes such as an increase in the number and thickness of elastic fibres, a loss of vertical fibres from the elastic tissue membrane, and the presence of large, irregular fibroblasts in the cells of this elastic tissue.
In contrast, extrinsic ageing results in clinical impairments such as large wrinkles and formation of a flaccid, tanned skin, and histopathological changes such as an excessive accumulation of elastic matter in the upper dermis and degeneration of the collagen fibres.
The invention is especially focused on intrinsic or physiological ageing and also extrinsic ageing.
Various agents for combating ageing of the skin are known in the prior art, among which are antioxidants, agents for promoting the proliferation and/or differentiation of dermal and/or epidermal cells, agents for stimulating the expression of dermal or epidermal macromolecules, that is to say as many agents as there are cellular or molecular targets in the skin for preventing and/or reducing the manifold effects of ageing of the skin. Thus, patent US-A-4 603 146 describes the use of retinoic acid and derivatives thereof in cosmetic compositions, for combating ageing of the skin. Desquamating agents are also added to these agents for combating ageing of the skin. In general, the desquamating agents act by facilitating the removal of the dead cells located at the surface of the horny layer of the epidermis. This "desquamating" property is also referred to, often incorrectly, as a keratolytic property. Unfortunately, certain desquamating compounds may also have, when they are used at high concentration, side effects such as cutaneous discomfort.
There is thus a need to find alternative solutions, for example to find means for using the said desquamating agents at lower doses to reduce these side effects.
The inventors have discovered, surprisingly, that certain C-glycoside derivatives allow the desquamating action of the desquamating agents to be reinforced.
C-Glycoside derivatives are especially described in document WO 02/051 828 for their properties on the synthesis of glycosaminoglycans (GAGs) and in particular for improving the moisturization and suppleness of the skin.
Thus, according to one of these aspects, the invention relates to a cosmetic and/or dermatological composition comprising, in a physiologically acceptable medium: from 0.001% to 95% by weight, relative to the total weight of the composition, of at least one desquamating agent, and at least one C-glycoside derivative corresponding to the general formula (I) below:
X-R
S (I) in which: - R denotes a linear Ci -C4 and especially C1-C3 alkyl radical, optionally substituted with -OH, -COOH or -COOR"2, R"2 being a saturated Ci-C4 alkyl radical, especially ethyl;
S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units and in particular up to 6 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 hydroxy 1 group, and optionally one or more optionally protected amine fϊmction(s); and
X represents a group chosen from -CO-, -CH(OH)-, -CH(NH2)-, -CH(NHCH2CH2CH2OH)-, -CH(NHPh)- and -CH(CH3)-, and more particularly a -CO-, -CH(OH)- or -CH(NH2)- group, and preferentially a -CH(OH)- group; - the bond S-CH2-X represents a bond of C-anomeric nature, which may be α or β, and also the cosmetically acceptable salts thereof, the solvates thereof such as hydrates, and the isomers thereof.
According to another of its aspects, a subject of the invention is the cosmetic use of at least one composition according to the invention for promoting desquamating of the skin and/or the scalp and/or for stimulating epidermal renewal, and especially for preventing, attenuating and/or combating the signs of ageing of the skin, for improving the appearance and/or texture of the skin and/or the scalp, and especially for improving the radiance and homogeneity of the complexion and/or for making the skin smooth, reducing the surface irregularities and the skin's microrelief, promoting the cleansing action and the removal of dead cells at the surface of the body, promoting the removal of dandruff, combating imperfections of greasy skin, improving the staying power of makeup and/or improving the result of treating the skin with stratum corneum colorants such as dihydroxyacetone (DHA). The invention also relates to the use of at least one desquamating agent in combination with at least one C-glycoside derivative according to the invention for the preparation of a composition for treating certain skin pathologies associated with abnormal desquamation, such as xerosis, ichthyosis, psoriasis and atopic dermatitis.
A subject of the invention is also a cosmetic treatment process for the non- therapeutic care of the skin and/or the scalp, characterized in that it comprises the simultaneous or sequential application to the skin, via at least one composition, of at least one C-glycoside derivative and of at least one desquamating agent according to the invention.
The cosmetic treatment process according to the invention may comprise at least one step that consists in applying a cosmetic composition according to the present invention to the skin and/or the scalp.
The cosmetic treatment process for the non-therapeutic care of the skin and/or the scalp according to the invention is more particularly a process for promoting the desquamation of the skin and/or the scalp, and/or for stimulating epidermal renewal, and especially for preventing, attenuating and/or combating the signs of ageing of the skin, for improving the appearance and/or texture of the skin and/or the scalp, and especially for improving the radiance and homogeneity of the complexion and/or for making the skin smooth, for reducing the surface irregularities and the skin's microrelief, for promoting the cleansing action and the removal of dead cells at the surface of the body, for promoting the removal of dandruff, for improving the staying power of makeup and/or for improving the result of treating the skin with stratum corneum colorants such as dihydroxy acetone (DHA).
In the process according to the invention, the C-glycoside derivative and the desquamating agent may be conditioned in two different compositions.
The improvement in the staying power of makeup and/or of skin colouring treatments with DHA results from the fact that the skin and/or the scalp may be prepared before the abovementioned makeup and/or colouring operations by the application of a composition according to the invention, which will promote the result of a simultaneous or subsequent treatment with a makeup agent and/or a colouring agent.
The term "sign of ageing of the skin" means any change in the outer appearance of the skin and/or in its texture due to chronological or photo-induced ageing, for instance wrinkles, fine lines, wizened skin, flaccid skin, thinned skin and lack of elasticity or tonus of the skin.
The pro-desquamating activity is effectively sought mainly in the field of "anti- ageing" compositions, i.e. compositions for combating the cutaneous signs caused by ageing and/or photo-ageing. However, the combination used according to the present invention may also find applications in attenuating surface irregularities of the skin and in improving the skin's microrelief, in particular attenuating actinic lentigo and acne or chickenpox scars, and unblocking skin pores; treating dry skin and acne-prone greasy skin. As regards greasy skin, this is often associated with a desquamation defect, and with a thick skin grain. Furthermore, the excess sebum may serve as a support for the anarchic growth of saprophytic bacterial flora (in particular Propionibacterium acnes and Pityrosporum ovale), and cause the appearance of comedones and/or acne scars. These acne scars are another cutaneous sign of greasy skin that may advantageously be combated by means of the use of at least one composition according to the present invention.
In the context of the present invention, it is understood that all the abovementioned complaints are covered by the expression "improving the appearance and/or texture of the skin and/or the scalp" and also by the more particular expression
"improving the radiance and homogeneity of the complexion and/or improving the skin's microrelief.
For the implementation of this process, the combination of a desquamating agent and of a C-glycoside derivative or the composition according to the invention may be applied to any area of skin or of its appendages, especially of the face, the neckline or the hands, or the lips, in order to attenuate the visible and/or tactile irregularities of the skin, for example for attenuating scars and for making the surface smooth and/or removing dead skin, especially from the lips.
According to one particular embodiment, the C-glycoside derivative and the desquamating agent that are the subject of the combination according to the invention may be conditioned in two different compositions and applied simultaneously or sequentially.
By way of example, the composition comprising the C-glycoside may be applied to prepare the skin for the subsequent application of the desquamating agent.
In addition, many skin pathologies are characterized by the production of a thickened horny layer and by abnormal desquamation, i.e. hyperkeratosis. This may occur on any anatomical region of skin and in very varied clinical contexts. Its physiopathological substratum and its cause are varied.
Advantageously, the combination and the compositions in accordance with the invention make it possible to promote desquamation of the skin and/or to stimulate epidermal renewal and thus, more particularly, to treat skin and/or scalp pathologies that are characterized by the production of a thickened horny layer and/or by abnormal desquamation.
Consequently, according to another of its aspects, the present invention also relates to the use of the combination or of a composition according to the invention for the preparation of a composition for treating skin and/or scalp pathologies characterized by the production of a thickened horny layer and/or by abnormal desquamation.
As non-limiting illustrations of these skin and/or scalp disorders associated with deregulation of desquamation, mention may be made, in the context of the present invention, of: xerosis, acne, - hyperkeratosis, psoriasis, atopy, and ichthyosis.
The combination of at least one desquamating agent and of at least one C-glycoside derivative or of a composition according to the invention makes it possible to promote the desquamation of the skin and/or the scalp and/or to stimulate epidermal renewal and may thus be used for the preparation of a dermatological composition for treating the abovementioned skin pathologies that are characterized by the production of a thickened horny layer and/or by abnormal desquamation. Finally, the composition according to the present invention finds another application in the field of chemical peeling treatments. The combination according to the invention is thus advantageous in peeling compositions.
Peeling treatments are a well-known means for improving the appearance and/or texture of the skin and/or the scalp, and especially for improving the radiance and homogeneity of the complexion and/or for reducing the visible and/or tactile irregularities of the skin, and in particular for improving the surface appearance of the skin, for attenuating actinic lentigo and acne or chickenpox scars, and also for preventing, attenuating or combating the signs of ageing of the skin, and especially for smoothing out skin texture irregularities, such as wrinkles and fine lines. They have the effect of removing a surface portion of the skin to be treated
(epidermis and possibly surface layer of the dermis) via chemical methods.
A subject of the invention is thus a cosmestic process for treating the visible and/or tactile irregularities of human skin, comprising the steps consisting in: a) applying topically to the skin a composition according to the present invention, b) leaving the composition in contact with the skin for a period of between 5 minutes and 6 hours and preferably between 5 minutes and 30 minutes, and c) removing the composition by rinsing.
According to an alternative embodiment, the invention relates to a cosmetic process for promoting the desquamation of the skin and/or mucous membranes, comprising at least one step (i) of preparing the skin for peeling, which consists in applying to the areas to be treated at least one C-glycoside derivative as defined hereinbelow, at least at a concentration below that resulting from desquamation, and (ii) a subsequent step comprising application of at least one desquamating agent at a concentration suitable for causing desquamation. A step for removing the desquamating agent(s) by rinsing will then be performed.
Advantageously, step (i) may be repeated with increasing concentrations of C-glycoside derivative. These concentrations will be adapted by a person skilled in the art as a function of the desired effect and of the envisaged number of applications, but will generally be less than 10%. It will be possible, for example, to use a first concentration of about 2%, followed by one or more successive applications with a concentration of about 4%, and then 6% or 8% by weight.
This process is more particularly intended for preventing, attenuating and/or combating the signs of ageing of the skin, and especially for attenuating wrinkles and fine lines, and for improving the appearance and/or texture of the skin, in particular for improving the homogeneity of the complexion and/or for making the skin smooth, and especially for attenuating actinic lentigo or acne or chickenpox scars, and/or for deblocking the skin pores.
DESQUAMATING AGENT The term "desquamating agent" means any compound capable of acting: either directly on desquamation by promoting exfoliation, such as: saturated and unsaturated monocarboxylic acids, saturated and unsaturated dicarboxylic acids, saturated and unsaturated tricarboxylic acids; α-hydroxy acids and β-hydroxy acids of monocarboxylic acids; α-hydroxy acids and β-hydroxy acids of dicarboxylic acids; α-hydroxy acids and β-hydroxy acids of tricarboxylic acids; keto acids, α-keto acids or β-keto acids of polycarboxylic acids, of polyhydroxymonocarboxylic acids, of polyhydroxydicarboxylic acids or of polyhydroxytricarboxylic acids; and (3-hydroxy- 2-pentylcyclopentyl)acetic acid.
Preferred α-hydroxy acids that may be mentioned include: gly colic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid.
Preferred β-hydroxy acids are chosen from: salicylic acid and derivatives thereof, in particular 5-n-octanoylsalicylic acid.
Other exfo Hants that may be mentioned include: pyruvic acid, gluconic acid, glucuronic acid, oxalic acid, malonic acid, succinic acid, acetic acid, gentisic acid, cinnamic acid, azelaic acid; phenol, resorcinol; urea and derivatives thereof; oligofucoses as in patent EP 0 218 200; jasmonic acid and derivatives thereof as in patent applications EP 1 333 022 and EP 1 333 021; trichloroacetic acid; retinoids such as retinol or retinoic acid; adapalene; the extract of Saphora japonica; resveratrol; and also salts and derivatives thereof, such as the cis or trans forms, racemic mixtures and the dextrorotatory or laevorotatory forms of the abovementioned agents.
- or on the enzymes involved in the desquamation or degradation of corneodesmosomes, such as glycosidases, stratum corneum chymotryptic enzyme (SCCE) or even other proteases (trypsin, chymotrypsin-like). Mention may be made especially of mineral salt chelating agents such as EDTA; N-acyl-N,N',N'-ethylenediaminetriacetic acid; amino sulfonic compounds and in particular (N-2-hydroxyethylpiperazine-N- 2-ethane)sulfonic acid (HEPES); 2-oxothiazolidine-4-carboxylic acid (procysteine) deriavtives; derivatives of α-amino acids of glycine type (as described in EP 0 852 949, and also sodium methyl glycine diacetate sold by BASF under the trade name TRILON M®); honey; sugar derivatives such as O-octanoyl-6-D-maltose, O-linoleyl-6-D- glucose and N-acetylglucosamine.
As other desquamating agents that may be used in the composition according to the invention, mention may be made of extracts of laminaria such as Laminaria saccharina and Laminaria ochrolenca, glyceryl trilactate, siliceous salicylate derivatives as in patent EP 0 796 861, 5-acylsalicylic acid salts, active agents with effects on transglutaminase as in patent EP 0 899 330, and an extract of Ficus opuntia indica blossom, such as Exfolactive® from Silab. Preferred desquamating agents that may be mentioned include β-hydroxy acids, such as 5-n-octanoylsalicylic acid; urea and derivatives thereof; glycolic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid; (N-2 hydroxyethylpiperazine-N- 2-ethane)sulfonic acid (HEPES); the extract of Saphora japonica; honey; N-acetylglucosamine; 2-oxothiazolidine-4-carboxylic acid (procysteine) derivatives, and mixtures thereof.
Even more preferentially, a desquamating agent chosen from glycolic acid, 5-n-octanoylsalicylic acid, (N-2-hydroxyethylpiperazine-N-2-ethane)sulfonic acid (HEPES) and 2-oxothiazolidine-4-carboxylic acid (procysteine) derivatives, and mixtures thereof, will be used in the composition of the invention.
A person skilled in the art will be able to define the necessary amount of desquamating agent present in the combination according to the invention in order to obtain the desired effect on the skin.
By way of example, the desquamating agent may be in a content ranging from 0.001% to 95% by weight relative to the total weight of the composition, in particular from 0.01% to 30% by weight relative to the total weight of the composition and preferentially from 0.01% to 10% by weight relative to the total weight of the composition. When the composition has a peeling application, it may especially contain from
0.01% to 90% by weight of desquamating agent(s) relative to the total weight of the composition, and preferably from 1% to 70% by weight relative to the total weight of the composition.
Preferably, at least 10% by weight, in particular more than 20% by weight, especially from 21% to 50% and preferably from 21% to 30% by weight of desquamating agent, relative to the total weight of the composition, will be used in the peeling compositions.
C-GLYCOSIDE DERIVATIVES A C-glycoside derivative that is suitable for use in the invention is a compound of general formula (I) below:
X-R
8^ (D in which:
- R denotes a linear Ci -C4 and especially C1-C3 alkyl radical, optionally substituted with -OH, -COOH or -COOR"2, R"2 being a saturated Ci-C4 alkyl radical, especially ethyl; - S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units and in particular up to 6 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 hydroxy 1 group, and optionally one or more optionally protected amine function(s); and
X represents a group chosen from -CO-, -CH(OH)-, -CH(NH2)-, -CH(NHCH2CH2CH2OH)-, -CH(NHPh)- and -CH(CH3)-, and more particularly a -CO-, -CH(OH)- or -CH(NH2)- group, and preferentially a -CH(OH)- group;
- the bond S-CH2-X represents a bond of C-anomeric nature, which may be α or β, and also the cosmetically acceptable salts thereof, the solvates thereof such as hydrates, and the isomers thereof.
Among the alkyl groups that are suitable for use in the invention, mention may be made especially of methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, isobutyl, sec- butyl, pentyl, n-hexyl, cyclopropyl, cyclopentyl, cyclohexyl and allyl groups.
According to one embodiment of the invention, it is possible to use a C-glycoside derivative corresponding to formula (I) for which S may represent a monosaccharide or a polysaccharide containing up to 6 sugar units, in pyranose and/or furanose form and of L and/or D series, the said monosaccharide or polysaccharide containing at least one hydroxyl function that is mandatorily free and/or optionally one or more amine functions that are mandatorily protected, X and R otherwise retaining all the definitions given above.
Advantageously, a monosaccharide of the invention may be chosen from D- glucose, D-galactose, D-mannose, D-xylose, D-lyxose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D- glucosamine and N-acetyl-D-galactosamine, and advantageously denotes D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D-xylose.
More particularly, a polysaccharide of the invention containing up to 6 sugar units may be chosen from D-maltose, D-lactose, D-cellobiose, D-maltotriose, a disaccharide combining a uronic acid chosen from D-iduronic acid and D-glucuronic acid with a hexosamine chosen from D-galactosamine, D-glucosamine, N-acetyl-D- galactosamine and N-acetyl-D-glucosamine, an oligosaccharide containing at least one xylose advantageously chosen from xylobiose, methyl-β-xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and especially xylobiose, which is composed of two xylose molecules linked via a 1-4 bond.
More particularly, S may represent a monosaccharide chosen from D-glucose, D-xylose, L-fucose, D-galactose and D-maltose, especially D-xylose.
Preferentially, a C-glycoside derivative of formula (I) is used, for which:
R denotes an unsubstituted linear Ci -C4 and especially Ci-C2 alkyl radical, in particular ethyl;
S represents a monosaccharide as described above; especially D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, in particular D-xylose;
X represents a group chosen from -CO-, -CH(OH)- and -CH(NH2)- and preferentially a CH(OH)- group.
The salts that are acceptable for the non-therapeutic use of the compounds described in the present invention comprise conventional non-toxic salts of the said compounds such as those formed from organic or inorganic acids. Examples that may be mentioned include the salts of mineral acids, such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydriodic acid, phosphoric acid or boric acid. Mention may also be made of the salts of organic acids, which may comprise one or more carboxylic, sulfonic or phosphonic groups. They may be linear, branched or cyclic aliphatic acids or alternatively aromatic acids. These acids may also comprise one or more heteroatoms chosen from O and N, for example in the form of hydroxyl groups. Mention may be made especially of propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.
When the compound of formula (I) comprises an acid group, neutralization of the acid group(s) may be performed with a mineral base, such as LiOH, NaOH, KOH, Ca(OH)2, NH4OH, Mg(OH)2 or Zn(OH)2; or with an organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine. This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and/or oxygen atoms and may thus comprise, for example, one or more alcohol functions; mention may be made especially of amino-2-methyl-2-propanol, triethanolamine, dimethylamino-2-propanol or 2-amino-2-(hydroxymethyl)-l,3-propanediol. Mention may also be made of lysine or
3-(dimethylamino)propylamine.
The solvates that are acceptable for the compounds described in the present invention comprise conventional solvates such as those formed during the final step of preparation of the said compounds due to the presence of solvents. Examples that may be mentioned include the solvates due to the presence of water or of linear or branched alcohols, for instance ethanol or isopropanol. Among the C-glycoside derivatives of formula (I) used according to the invention, the ones that are most particularly considered are:
1. C-β-D-xylopyranoside-n-propan-2-one;
2. C-α-D-xylopyranoside-n-propan-2-one;
3. l-[2-(3-hydroxypropylamino)propyl]-C-β -D-xylopyranose; 4. l-[2-(3-hydroxypropylamino)propyl]-C-α-D-xylopyranose;
5. C-β-D-xylopyranoside-2-hydroxypropane;
6. C-α-D-xylopyranoside-2-hydroxypropane;
7. C-β-D-xylopyranoside-2-aminopropane;
8. C-α-D-xylopyranoside-2-aminopropane; 9. C-β-D-xylopyranoside-2-phenylaminopropane;
10. C-α-D-xylopyranoside-2-phenylaminopropane;
11. ethyl 3-methyl-4-(C-β-D-xylopyranoside)butyrate;
12. ethyl 3-methyl-4-(C-CC-D-xylopyranoside)butyrate;
13. 6-(C-β-D-xylopyranoside)-5-ketohexanoic acid; 14. 6-(C-α-D-xylopyranoside)-5-ketohexanoic acid;
15. 6-(C-β-D-xylopyranoside)-5-hydroxyhexanoic acid;
16. 6-(C-α-D-xylopyranoside)-5-hydroxyhexanoic acid;
17. 6-(C-β-D-xylopyranoside)-5-aminohexanoic acid;
18. 6-(C-α-D-xylopyranoside)-5-aminohexanoic acid; 19. 6-(C-β-D-xylopyranoside)-5-phenylaminohexanoic acid;
20. 6-(C-α-D-xylopyranoside)-5-phenylaminohexanoic acid;
21. 1 -(C-β-D-xylopyranoside)hexane-2,6-diol;
22. 1 -(C-α-D-xylopyranoside)hexane-2,6-diol;
23. 5-(C-β-D-xylopyranoside)-4-ketopentanoic acid; 24. 5-(C-α-D-xylopyranoside)-4-ketopentanoic acid;
25. 5-(C-β-D-xylopyranoside)-4-hydroxypentanoic acid; 26. 5-(C-α-D-xylopyranoside)-4-hydroxypentanoic acid;
27. 5-(C-β-D-xylopyranoside)-4-aminopentanoic acid;
28. 5-(C-α-D-xylopyranoside)-4-aminopentanoic acid;
29. 5-(C-β-D-xylopyranoside)-4-phenylaminopentanoic acid; 30. 5-(C-α-D-xylopyranoside)-4-phenylaminopentanoic acid;
31. 1 -(C-β-D-xylopyranoside)pentane-2,5-diol;
32. 1 -(C-α-D-xylopyranoside)pentane-2,5-diol;
33. 1 -(C-β-D-fucopyranoside)propan-2-one;
34. 1 -(C-α-D-fucopyranoside)propan-2-one; 35. l-(C-β-L-fucopyranoside)propan-2-one;
36. 1 -(C-α-L-fucopyranoside)propan-2-one;
37. 1 -(C-β-D-fucopyranoside)-2-hydroxypropane;
38. 1 -(C-α-D-fucopyranoside)-2-hydroxypropane;
39. 1 -(C-β-L-fucopyranoside)-2-hydroxypropane; 40. l-(C-α-L-fucopyranoside)-2-hydroxypropane;
41. 1 -(C-β-D-fucopyranoside)-2-aminopropane;
42. 1 -(C-α-D-fucopyranoside)-2-aminopropane;
43. 1 -(C-β-L-fucopyranoside)-2-aminopropane;
44. 1 -(C-α-L-fucopyranoside)-2-aminopropane; 45. l-(C-β-D-fucopyranoside)-2-phenylaminopropane;
46. 1 -(C-α-D-fucopyranoside)-2-phenylaminopropane;
47. 1 -(C-β-L-fucopyranoside)-2-phenylaminopropane;
48. 1 -(C-α-L-fucopyranoside)-2-phenylaminopropane;
49. ethyl 3-methyl-4-(C-β-D-fucopyranoside)butyrate; 50. ethyl 3-methyl-4-(C-α-D-fucopyranoside)butyrate;
51. ethyl 3-methyl-4-(C-β-L-fucopyranoside)butyrate;
52. ethyl 3-methyl-4-(C-α-L-fucopyranoside)butyrate;
53. 6-(C-β-D-fucopyranoside)-5-ketohexanoic acid;
54. 6-(C-α-D-fucopyranoside)-5-ketohexanoic acid; 55. 6-(C-β-L-fucopyranoside)-5-ketohexanoic acid; 56. 6-(C-α-L-fucopyranoside)-5-ketohexanoic acid;
57. 6-(C-β-D-fucopyranoside)-5-hydroxyhexanoic acid;
58. 6-(C-α-D-fucopyranoside)-5-hydroxyhexanoic acid;
59. 6-(C-β-L-fucopyranoside)-5-hydroxyhexanoic acid; 60. 6-(C-α-L-fucopyranoside)-5-hydroxyhexanoic acid;
61. 6-(C-β-D-fucopyranoside)-5-aminohexanoic acid;
62. 6-(C-α-D-fucopyranoside)-5-aminohexanoic acid;
63. 6-(C-β-L-fucopyranoside)-5-aminohexanoic acid;
64. 6-(C-α-L-fucopyranoside)-5-aminohexanoic acid; 65. l-(C-β-D-fucopyranoside)hexane-2,6-diol;
66. l-(C-α-D-fucopyranoside)hexane-2,6-diol;
67. l-(C-β-L-fucopyranoside)hexane-2,6-diol;
68. l-(C-α-L-fucopyranoside)hexane-2,6-diol;
69. 5-(C-β-D-fucopyranoside)-4-ketopentanoic acid; 70. 5-(C-α-D-fucopyranoside)-4-ketopentanoic acid;
71. 5-(C-β-L-fucopyranoside)-4-ketopentanoic acid;
72. 5-(C-α-L-fucopyranoside)-4-ketopentanoic acid;
73. 5-(C-β-D-fucopyranoside)-4-hydroxypentanoic acid;
74. 5-(C-α-D-fucopyranoside)-4-hydroxypentanoic acid; 75. 5-(C-β-L-fucopyranoside)-4-hydroxypentanoic acid;
76. 5-(C-α-L-fucopyranoside)-4-hydroxypentanoic acid;
77. 5-(C-β-D-fucopyranoside)-4-aminopentanoic acid;
78. 5-(C-α-D-fucopyranoside)-4-aminopentanoic acid
79. 5-(C-β-L-fucopyranoside)-4-aminopentanoic acid; 80. 5-(C-α-L-fucopyranoside)-4-aminopentanoic acid;
81. l-(C-β-D-fucopyranoside)pentane-2,5-diol;
82. l-(C-α-D-fucopyranoside)pentane-2,5-diol;
83. l-(C-β-L-fucopyranoside)pentane-2,5-diol;
84. l-(C-α-L-fucopyranoside)pentane-2,5-diol; 85. l-(C-β-D-glucopyranosyl)-2-hydroxypropane; 86. 1 -(C-α-D-glucopyranosyl)-2-hydroxypropane;
87. 1 -(C-β-D-glucopyranosyl)-2-aminopropane;
88. l-(C-α-D-glucopyranosyl)-2-aminopropane;
89. 1 -(C-β-D-glucopyranosyl)-2-phenylaminopropane; 90. l-(C-α-D-glucopyranosyl)-2-phenylaminopropane;
91. ethyl 3-methyl-4-(C-β-D-glucopyranosyl)butyrate;
92. ethyl 3-methyl-4-(C-α-D-glucopyranosyl)butyrate;
93. 6-(C-β-D-glucopyranosyl)-5-ketohexanoic acid;
94. 6-(C-α-D-glucopyranosyl)-5-ketohexanoic acid; 95. 6-(C-β-D-glucopyranosyl)-5-hydroxyhexanoic acid;
96. 6-(C-α-D-glucopyranosyl)-5-hydroxyhexanoic acid;
97. 6-(C-β-D-glucopyranosyl)-5-aminohexanoic acid;
98. 6-(C-α-D-glucopyranosyl)-5-aminohexanoic acid;
99. 6-(C-β-D-glucopyranosyl)-5-phenylaminohexanoic acid; 100. 6-(C-α-D-glucopyranosyl)-5-phenylaminohexanoic acid;
101. 1 -(C-β-D-glucopyranosyl)hexane-2,6-diol;
102. 1 -(C-α-D-glucopyranosyl)hexane-2,6-diol;
103. 6-(C-β-D-glucopyranosyl)-5-ketopentanoic acid;
104. 6-(C-α-D-glucopyranosyl)-5-ketopentanoic acid; 105. 6-(C-β-D-glucopyranosyl)-5-hydroxypentanoic acid;
106. 6-(C-α-D-glucopyranosyl)-5-hydroxypentanoic acid;
107. 6-(C-β-D-glucopyranosyl)-5-aminopentanoic acid;
108. 6-(C-α-D-glucopyranosyl)-5-hydroxypentanoic acid;
109. 6-(C-β-D-glucopyranosyl)-5-phenylaminopentanoic acid; 110. 6-(C-α-D-glucopyranosyl)-5-phenylaminopentanoic acid;
111. 1 -(C-β-D-glucopyranosyl)pentane-2,5-diol;
112. l-(C-α-D-glucopyranosyl)pentane-2,5-diol;
113. 1 -(C-β-D-galactopyranosyl)-2-hydroxypropane;
114. l-(C-α-D-galactopyranosyl)-2-hydroxypropane; 115. l-(C-β-D-galactopyranosyl)-2-aminopropane; 116. 1 -(C-α-D-galactopyranosyl)-2-aminopropane;
117. 1 -(C-β-D-galactopyranosyl)-2-phenylaminopropane;
118. 1 -(C-α-D-galactopyranosyl)-2-phenylaminopropane;
119. ethyl 3-methyl-4-(β-D-galactopyranosyl)butyrate; 120. ethyl 3-methyl-4-(α-D-galactopyranosyl)butyrate;
121. 6-(C-β-D-galactopyranosyl)-5-ketohexanoic acid;
122. 6-(C-α-D-galactopyranosyl)-5-ketohexanoic acid;
123. 6-(C-β-D-galactopyranosyl)-5-hydroxyhexanoic acid;
124. 6-(C-α-D-galactopyranosyl)-5-hydroxyhexanoic acid; 125. 6-(C-β-D-galactopyranosyl)-5-aminohexanoic acid;
126. 6-(C-α-D-galactopyranosyl)-5-aminohexanoic acid;
127. 6-(C-β-D-galactopyranosyl)-5-phenylaminohexanoic acid;
128. 6-(C-α-D-galactopyranosyl)-5-phenylaminohexanoic acid;
129. l-(C-β-D-galactopyranosyl)hexane-2,6-diol; 130. l-(C-α-D-galactopyranosyl)hexane-2,6-diol;
131. 6-(C-β-D-galactopyranosyl)-5-ketopentanoic acid;
132. 6-(C-α-D-galactopyranosyl)-5-ketopentanoic acid;
133. 6-(C-β-D-galactopyranosyl)-5-hydroxypentanoic acid;
134. 6-(C-α-D-galactopyranosyl)-5-hydroxypentanoic acid; 135. 6-(C-β-D-galactopyranosyl)-5-aminopentanoic acid;
136. 6-(C-α-D-galactopyranosyl)-5-aminopentanoic acid;
137. 6-(C-β-D-galactopyranosyl)-5-phenylaminopentanoic acid;
138. 6-(C-α-D-galactopyranosyl)-5-phenylaminopentanoic acid;
139. 1 -(C-β-D-galactopyranosyl)pentane-2,6-diol; 140. l-(C-α-D-galactopyranosyl)pentane-2,6-diol;
141. l-(C-β-D-flιcofuranosyl)propan-2-one;
142. l-(C-α-D-flιcofuranosyl)propan-2-one;
143. l-(C-β-L-flιcofuranosyl)propan-2-one;
144. l-(C-α-L-flιcofuranosyl)propan-2-one; 145. 3'-(acetamido-C-β-D-glucopyranosyl)propane-2'-one; 146. 3 '-(acetamido-C-α-D-glucopyranosyl)propane-2'-one;
147. l-(acetamido-C-β-D-glucopyranosyl)-2-hydroxylpropane;
148. 1 -(acetamido-C-β-D-glucopyranosyl^-aminopropane;
149. l^acetamido-C-β-D-glucopyranosyl^-phenylaminopropane; 150. l-(acetamido-C-α-D-glucopyranosyl)-2-phenylaminopropane;
151. ethyl 3-methyl-4-(acetamido-C-β-D-glucopyranosyl)butyrate;
152. ethyl 3-methyl-4-(acetamido-C-α-D-glucopyranosyl)butyrate;
153. 6-(acetamido-C-β-D-glucopyranosyl)-5-ketohexanoic acid;
154. 6-(acetamido-C-α-D-glucopyranosyl)-5-ketohexanoic acid; 155. 6-(acetamido-C-β-D-glucopyranosyl)-5-hydroxyhexanoic acid;
156. 6-(acetamido-C-α-D-glucopyranosyl)-5-hydroxyhexanoic acid;
157. 6-(acetamido-C-β-D-glucopyranosyl)-5-aminohexanoic acid;
158. 6-(acetamido-C-α-D-glucopyranosyl)-5-aminohexanoic acid;
159. 6-(acetamido-C-β-D-glucopyranosyl)-5-phenylaminohexanoic acid; 160. 6-(acetamido-C-α-D-glucopyranosyl)-5-phenylaminohexanoic acid;
161. 1 -(acetamido-C-β-D-glucopyranosyl)hexane-2,6-diol;
162. 1 -(acetamido-C-α-D-glucopyranosyl)hexane-2,6-diol;
163. 6-(acetamido-C-β-D-glucopyranosyl)-5-ketopentanoic acid;
164. 6-(acetamido-C-α-D-glucopyranosyl)-5-ketopentanoic acid; 165. 6-(acetamido-C-β-D-glucopyranosyl)-5-hydroxypentanoic acid;
166. 6-(acetamido-C-α-D-glucopyranosyl)-5-hydroxypentanoic acid;
167. 6-(acetamido-C-β-D-glucopyranosyl)-5-aminopentanoic acid;
168. 6-(acetamido-C-α-D-glucopyranosyl)-5-aminopentanoic acid;
169. 6-(acetamido-C-β-D-glucopyranosyl)-5-phenylaminopentanoic acid; 170. 6-(acetamido-C-α-D-glucopyranosyl)-5-phenylaminopentanoic acid;
171. 1 -(acetamido-C-β-D-glucopyranosyl)pentane-2,5-diol;
172. 1 -(acetamido-C-α-D-glucopyranosyl)pentane-2,5-diol.
As non-limiting illustrations of C-glycoside derivatives that are more particularly suitable for use in the invention, mention may be made especially of the following derivatives: 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, - l-(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, - l-(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-hydroxylpropane,
1 -(C-α-D-glucopyranosyl)-2-hydroxylpropane, - l-(C-β-D-galactopyranosyl)-2-hydroxylpropane,
1 -(C-α-D-galactopyranosyl)-2-hydroxylpropane
1 -(C-β-D-fucofuranosyl)propan-2-one,
1 -(C-α-D-fucofuranosyl)propan-2-one
1 -(C-β-L-fucofuranosyl)propan-2-one, - l-(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.
According to one embodiment, C-β-D-xylopyranoside-2-hydroxypropane or C-α-D-xylopyranoside-2-hydroxypropane, and better still C-β-D-xylopyranoside- 2-hydroxypropane, may advantageously be used for the preparation of a composition according to the invention. According to one particular embodiment, the C-glycoside derivative may be
C-β-D-xylopyranoside-2-hydroxypropane, which is in the form of a solution containing 30% by weight of active material in a water/propylene glycol mixture (60%/40% by weight) such as the product sold by CHIMEX under the trade name "Mexoryl SBB®".
Needless to say, according to the invention, a C-glycoside derivative corresponding to formula (I) may be used alone or as a mixture with other C-glycoside derivatives and in any proportion.
A C-glycoside derivative that is suitable for use in the invention may especially be obtained via the synthetic method described in document WO 02/051 828.
The amount of C-glycoside derivative to be used in a composition according to the invention depends on the desired cosmetic or therapeutic effect, and may thus vary within a wide range.
A person skilled in the art can readily determine the appropriate amounts, on the basis of his general knowledge.
A composition according to the invention may comprise a C-glycoside derivative in a proportion of about from 0.0001% to about 25% by weight of active material relative to the total weight of the composition, in particular from about 0.001% to about 10% by weight of active material and more particularly from about 0.05% to about 5% by weight of C-glycoside derivative active material relative to the total weight of the composition.
For use in peeling, the same contents may be envisaged in the corresponding compositions. It is also possible to use larger contents to further improve the desired desquamating effect and/or to reduce the content of desquamating agent in the combination according to the invention.
The mass ratio between the desquamating agent and the C-glycoside derivative may vary as a function of the intended galenical formulations and/or of the intended uses. The mass ratio may especially range from 0.0004 to 900, or even from 0.004 to
600, preferably from 0.01 to 300 and even more preferentially from 0.01 to 150, or even from 0.01 to 100.
In particular, in anti-ageing compositions, the mass ratio between the desquamating agent and the C-glycoside derivative may especially range from 0.01 to 100, preferably from 0.01 to 60, more preferentially from 0.01 to 30 and even more preferentially from 0.01 to 10, from 0.01 to 5, or even from 0.02 to 2.
In peeling compositions, the mass ratio between the desquamating agent and the C-glycoside derivative may especially range from 1 to 300, preferably from 2 to 150 and even more preferentially from 2 to 100, or even from 2 to 50.
ADDITIONAL AGENT The composition according to the present invention may also comprise at least one additional cosmetic and/or dermatological agent for improving the appearance and/or comfort of the skin and/or the scalp.
This additional agent may especially be an anti-ageing and/or anti-wrinkle agent. The anti-ageing and/or anti-wrinkle agent may especially be chosen from: - an anti-glycation agent, such as an extract of blueberry (Vaccinium angustifolium), for example the product sold under the name "Blueberry Herbasol Extract PG" by the company Cosmetochem, an extract of black tea such as Kombuchka from Sederma, or lipoic acid or thioctic acid such as Nutralip® from Labochim; an NO-synthase inhibitor, such as extracts of Ginkgo biloba, of Vitis vinifera or of Olea europaea; an agent acting on dermal or epidermal macromolecules and/or preventing their degradation, such as extracts of Centella asiatica, asiaticosides and derivatives; ascorbic acid and derivatives thereof; synthetic peptides such as iamin, biopeptide CL or palmitoyl pentapeptide sold by the company Sederma under the trade name Matrixil®; the malt extract sold by the company Coletica under the trade name Collalift®; lycopene; the extract of Saccharomyces cerevisiae available especially from the company SILAB under the trade name Firmalift® or from the company LSN under the trade name Cytovitin®; or on the inhibition of elastin degradation such as the peptide extract of Pisum sativum seeds sold by the company LSN under the trade name Parelastyl®; the N-acylamino amide compounds described in patent application WO 01/94381 such as {2-[acetyl-(3-trifluoromethylphenyl)amino]-3-methylbutyryl- amino} acetic acid, also known as N-[N-acetyl, N'-(3-trifluoromethyl)phenyl valyl] glycine or N-acetyl-N-[3-(trifluoromethyl)phenyl]valylglycine or acetyl trifluoromethyl phenyl valylglycine, or an ester thereof with a Ci-C6 alcohol; an extract of rice peptides such as Colhibin® from Pentapharm, the extract of the brown alga Padina pavonica sold by the company Alban Mϋller under the trade name HSP3®; an extract of Laminaria ochroleuca, such as Laminaϊne® from Secma; the extract of lupin sold by the company Silab under the trade name Structurine®; the extract of beech tree Fagus sylvatica buds sold by the company Gattefosse under the trade name Gatuline® RC; a pentapeptide extract of Voandzeia substerranea, such as the product sold by the company Laboratoires Serobiologiques under the trade name Filladyn LS 9397®; - an agent for modulating cell differentiation or proliferation, and especially keratinocyte differentiation and/or fibroblast or keratinocyte proliferation, such as a soybean extract (hydrolysed soybean proteins) such as Ridulisse® from Silab or 1 ,3,5-trimethoxybenzene (phloroglucinol): a muscle relaxant and/or dermo-decontracting agent, such as magnesium gluconate, manganese gluconate and other salts, alverine citrate and salts thereof, glycine, an extract of Iris pallida, a hexapeptide (Argeriline R from Lipotec) or sapogenins, for instance those from wild yam, and the carbonyl amines described in patent application EP 1 484 052, and adenosine; an agent especially having a dermo-contracting role. These additional anti-ageing agents are generally present in the cosmetic compositions at contents ranging from 0.01% to 20% by weight relative to the total weight of the composition, preferably from 0.01% to 10% by weight relative to the total weight of the composition and even more preferentially from 0.01% to 1% by weight relative to the total weight of the composition. The invention thus also relates to a composition comprising: at least one C-glycoside derivative, at least one desquamating agent chosen from 5-n-octanoylsalicylic acid, (N-2-hydroxyethylpiperazine-N-2-ethane)sulfonic acid (HEPES), or an EDTA derivative, and mixtures thereof; and - at least one additional anti-ageing agent, and preferably at least two anti- ageing agents chosen from adenosine, an extract of malt, an extract of Padina pavonica, an extract of soybean and an extract of wild yam, and mixtures thereof.
The compositions according to the invention comprise a physiologically acceptable medium. The term "physiologically acceptable medium" is intended to denote a medium which is compatible with human keratin materials and/or fibres, for instance, in a non-limiting manner, the skin, mucous membranes, the nails, the scalp and/or the hair. This physiologically acceptable medium comprises water, optionally as a mixture with one or more organic solvents such as Ci-Cs alcohols, especially ethanol, isopropanol, tert-butanol or n-butanol, polyols, for instance glycerol, propylene glycol or butylene glycol and polyol ethers. The compositions according to the invention may be a cosmetic or dermato logical composition and may thus comprise a cosmetically or pharmaceutically acceptable medium.
The composition may also comprise a fatty phase, which may comprise oils, gums or waxes usually used in the field of application under consideration. As oils or waxes that may be used in the invention, mention may be made of mineral oils (liquid petroleum jelly), plant oils (liquid fraction of shea butter, sunflower oil, apricot oil, rice bran oil, etc), animal oils (perhydrosqualene), synthetic oils (purcellin oil), silicone oils or waxes (cyclomethicone or dimethicone) and fluoro oils (perfluoropolyethers), beeswax, carnauba wax, paraffin wax, shea butter or hydrogenated jojoba oil. Fatty alcohols (cetyl alcohol, stearyl alcohol, etc) and fatty acids (stearic acid, etc) may be added to these oils.
When the composition is an emulsion, the proportion of the fatty phase may range from 5% to 80% by weight and preferably from 5% to 50% by weight relative to the total weight of the composition. The oils, waxes, emulsifiers and coemulsifiers used in the composition in emulsion form are chosen from those conventionally used in cosmetics. The emulsifier and the coemulsifϊer are present in the composition in a proportion ranging from 0.3% to 30% by weight and preferably from 0.5 to 20% by weight relative to the total weight of the composition. The emulsion may also contain lipid vesicles.
When the composition is an oily solution or gel, the fatty phase may represent more than 90% of the total weight of the composition. The composition may also contain adjuvants that are common in the field under consideration, such as surfactants, emulsifiers, hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic additives, preserving agents, antioxidants, solvents, fragrances, fillers, screening agents, odour absorbers and dyestuffs, and other cosmetic or pharmaceutical active agents. The amounts of these various adjuvants are those conventionally used in cosmetics, for example from 0.01% to 10% of the total weight of the composition. Depending on their nature, these adjuvants may be introduced into the fatty phase, into the aqueous phase and/or into lipid spherules. As surfactants that may be used, examples that may be mentioned include glyceryl stearate, polysorbate 60 and the mixture of PEG-6/PEG-32/glycol stearate sold under the name TefoseR 63 by the company Gattefosse; PEG stearate derivatives and sugar derivatives. As hydrophilic gelling agents that may be used in the invention, mention may be made of carboxyvinyl polymers (carbomer), acrylic copolymers such as acrylate/alkyl acrylate copolymers, polyacrylamides, polysaccharides such as hydroxypropylcellulose, natural gums and clays, and lipophilic gelling agents that may be mentioned include modified clays, for instance bentones, metal salts of fatty acids, for instance aluminium stearates, and hydrophobic silica, ethylcellulose or polyethylene.
The composition may be in any conceivable galenical form. The composition may especially be in the form of an aqueous, alcoholic, aqueous-alcoholic or oily solution; a dispersion of the lotion or serum type; a water-in-oil, oil-in-water or multiple emulsion; a suspension; microcapsules or microparticles; vesicular dispersions of ionic and/or non- ionic type; an aqueous or oily lotion or a lotion in serum form; a mousse or a solid preparation, for example in stick form; an aerosol composition also comprising a pressurized propellant or in the form of a patch.
The composition according to the invention may be in the form of a haircare composition, especially a shampoo, a hairsetting lotion, a medicated lotion, a styling cream or gel, a dye composition, especially for oxidation dyeing, a hair restructuring lotion, a permanent-waving composition (especially a composition for the first stage of a permanent-waving operation), a lotion or gel for preventing hair loss, or an antiparasitic shampoo.
It may also be in the form of a cleansing, protective, treating or care composition for the face, the hands, the feet, the major anatomical folds or the body (for example a day cream, a night cream, a makeup-removing cream, an antisun composition, a protective or care body milk, an after-sun milk, a skincare lotion, gel or mousse, for instance a cleansing lotion, or an artificial tanning composition); a body or facial makeup composition such as a foundation; a bath composition; a deodorizing composition comprising, for example, a bactericidal agent; an aftershave composition; a hair-removing composition; an insect-repelling composition; a pain-relief composition; a composition for treating certain skin diseases, for instance eczema, rosacea, psoriasis, lichens or severe pruritus.
When the composition according to the invention is intended for a use of peeling type, it may also be in any of the galenical forms mentioned above, provided that it can be removed easily by rinsing, and especially in the form of an aqueous gel or an aqueous or aqueous-alcoholic solution. It may be applied via any means allowing uniform distribution and especially using cotton wool, a cotton tip, a brush, a gauze, a spatula or a pad, or alternatively by spraying, and may be removed by rinsing with water or using a mild detergent. According to one preferred embodiment of the invention, the composition intended for chemical peeling contains a continuous aqueous phase. A subject of the present invention is also a composition for caring for the skin and/or the scalp, characterized in that the desquamating agent is chosen from β-hydroxy acids such as 5-n-octanoylsalicylic acid; urea and derivatives thereof; gly colic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid; (N-2-hydroxyethylpiperazine- N-2-ethane)sulfonic acid (HEPES); an extract of Saphora japonica; honey; N-acetylglucosamine and 2-oxothiazolidine-4-carboxylic acid (procysteine) derivatives, and extracts of laminaire such as Laminaria saccharina and Laminaria ochrolenca.
Finally, a subject of the present invention is a peeling composition, characterized in that the desquamating agent is present in a content of greater than 20% by weight, for example ranging from 21% by weight to 70% by weight, especially from 21% to 50% and even more preferentially from 21% to 30% by weight relative to the total weight of the composition.
The examples that follow illustrate the present invention.
EXAMPLES The C-glycoside derivative used is C-β-D-xylopyranoside-2-hydroxypropane, sold under the name MEXORYL® by Chimex. It is in the form of a solution containing 30% by weight of active material in a 60/40 water/1, 2-propanediol mixture.
Example 1 : Evaluation on reconstructed skin of the desquamating effect of a mixture between a desquamating agent and a C-glycoside derivative
The test uses a model of reconstructed skin: it consists in evaluating, by counting with a microscope, the number of corneocytes released after application of the desquamating product or of the desquamating mixture to be tested.
After culturing models of reconstructed skin, the test products are applied topically at various concentrations ranging from 0.01% to 50% to evaluate a dose effect. The test products are: glycolic acid at concentrations ranging from 1% to 70% by weight of active material;
C-β-D-xylopyranoside-2-hydroxypropane as a solution at 30% by weight in a 60/40 water/propylene glycol mixture used at concentrations ranging from 0.01% to 10% by weight of active material; a mixture of 5-n-octanoylsalicylic acid and of C-β-D-xylopyranoside- 2-hydroxypropane as a solution at 30% by weight in a 60/40 water/propylene glycol mixture.
The negative blank consists of an equivalent volume of MiIIiQ water. The positive blank is a 30% glycolic acid solution. Each condition is treated in triplicate.
Once the action time has elapsed (10 minutes), the corneocytes released after the treatment are counted on glass slides.
The following formulations are prepared according to the standard methods of those skilled in the art.
Example 2: Lotion
Figure imgf000027_0001
AM: active material Example 3: Oil-in-water cream
Figure imgf000028_0001
AM = active material The cream is applied daily to the skin of the face and/or the neck.
Compositions are obtained that are pleasant to apply and that have desquamating properties, without, however, causing the user any sensations of stinging, tautness or heating.

Claims

1. Cosmetic and/or dermatological composition comprising, in a physiologically acceptable medium: from 0.001% to 95% by weight, relative to the total weight of the composition, of at least one desquamating agent, and at least one C-glycoside derivative corresponding to the general formula (I) below:
X-R 0) in which:
R denotes a linear Ci -C4 and especially C1-C3 radical, optionally substituted with -OH, -COOH or -COOR"2, R"2 being a saturated Ci-C4 alkyl radical, especially ethyl; - S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units and in particular up to 6 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 - X represents a group chosen from -CO-, -CH(OH)-, -CH(NH2)-,
-CH(NHCH2CH2CH2OH)-, -CH(NHPh)- and -CH(CH3)-, and more particularly a -CO-,
-CH(OH)- or -CH(NH2)- group, and preferentially a -CH(OH)- group; the bond S-CH2-X represents a bond of C-anomeric nature, which may be α or β, and also the cosmetically acceptable salts thereof, the solvates thereof such as hydrates, and the isomers thereof.
2. Composition according to Claim 1, in which the desquamating agent is chosen from β-hydroxy acids, such as 5-n-octanoylsalicylic acid; urea and derivatives thereof; gly colic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid; (N-2-hydroxyethylpiperazine-N-2-ethane)sulfonic acid; the extract of Saphora japonica; honey; N-acetylglucosamine; 2-oxothiazolidine-4-carboxylic acid derivatives, and mixtures thereof.
3. Composition according to the preceding claim, in which the desquamating agent is chosen from glycolic acid, 5-n-octanoylsalicylic acid, (N-2-hydroxyethylpiperazine-N-2-ethane)sulfonic acid and 2-oxothiazolidine-4-carboxylic acid derivatives, and mixtures thereof.
4. Composition according to any one of the preceding claims, characterized in that it comprises the desquamating agent in a content ranging from 0.001% to 95% by weight relative to the total weight of the composition, in particular from 0.01% to 30% by weight relative to the total weight of the composition and preferentially from 0.01% to 10% by weight relative to the total weight of the composition.
5. Composition according to any one of the preceding claims, in which S represents a monosaccharide chosen from D-glucose, D-xylose, L-fucose, D-galactose and D-maltose, and especially D-xylose.
6. Composition according to any one of the preceding claims, 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, - l-(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, - l-(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-hydroxylpropane,
1 -(C-α-D-glucopyranosyl)-2-hydroxylpropane, - l-(C-β-D-galactopyranosyl)-2-hydroxylpropane,
1 -(C-α-D-galactopyranosyl)-2-hydroxylpropane 1 -(C-β-D-fucofuranosyl)propan-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.
7. Composition according to any one of the preceding claims, in which the
C-glycoside derivative is chosen from C-β-D-xylopyranoside-2-hydroxypropane and C-CC- D-xylopyranoside-2-hydroxypropane, and is more particularly C-β-D-xylopyranoside-2- hydroxypropane.
8. Cosmetic use of at least one composition as defined in any one of Claims 1 to 7, for promoting the desquamation of the skin and/or the scalp and/or for stimulating epidermal renewal.
9. Use according to Claim 8, characterized in that the said composition is intended for preventing, attenuating and/or combating the signs of ageing of the skin, for improving the appearance and/or texture of the skin and/or the scalp, and especially for improving the radiance and homogeneity of the complexion and/or making the skin smooth, for reducing surface irregularities in the skin's microrelief, for promoting the cleansing action and the removal of dead cells at the surface of the body, for promoting the removal of dandruff, for combating imperfections of greasy skin, for improving the staying power of makeup and/or for improving the result of treating the skin with stratum corneum colorants such as dihydroxy acetone.
10. Use of at least one desquamating agent in combination with at least one C-glycoside derivative as defined in any one of Claims 1 to 7, for the preparation of a composition for treating certain skin pathologies associated with abnormal desquamation, such as xerosis, ichthyosis, psoriasis and atopic dermatitis.
11. Cosmetic treatment process for the non-therapeutic care of the skin and/or the scalp, characterized in that it comprises the simultaneous or sequential application to the skin, via at least one composition, of at least one C-glycoside derivative and of at least one desquamating agent as defined in any one of Claims 1 to 7.
12. Process according to Claim 11, comprising at least one step that consists in applying to the skin and/or the scalp a cosmetic composition as defined in any one of Claims 1 to 7.
13. Process according to either of Claims 11 and 12, characterized in that it is a process for preventing, attenuating and/or combating the signs of ageing of the skin, for improving the appearance and/or texture of the skin and/or the scalp, and especially for improving the radiance and homogeneity of the complexion and/or making the skin smooth, for reducing surface irregularities in the skin's microrelief, for promoting the cleansing action and the removal of dead cells at the surface of the body, for promoting the removal of dandruff, for combating imperfections of greasy skin, for improving the staying power of makeup and/or for improving the result of treating the skin with stratum corneum colorants such as dihydroxy acetone.
14. Process according to any one of Claims 11 to 13, in which the C-glycoside derivative and the desquamating agent are conditioned in two different compositions.
15. Cosmetic process for treating visible and/or tactile irregularities of human skin, comprising the steps consisting in: a) applying topically to the skin a composition according to any one of Claims 1 to 7, b) leaving the composition in contact with the skin for a time of between 5 minutes and 6 hours and preferably between 5 minutes and 30 minutes, and c) removing the composition by rinsing.
16. Process according to Claim 15, characterized in that it is intended for preventing, attenuating and/or combating the signs of ageing of the skin, and especially for attenuating wrinkles and fine lines, and for improving the appearance and/or texture of the skin, in particular for improving the homogeneity of the complexion and/or for making the skin smooth, and especially for attenuating actinic lentigo, or acne or chickenpox scars, and/or for unblocking skin pores.
PCT/IB2007/052526 2006-07-03 2007-06-29 Cosmetic and/or dermatological composition combining a c-glycoside derivative and a desquamating agent WO2008004164A2 (en)

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WO2002051828A2 (en) * 2000-12-22 2002-07-04 L'oreal Novel c-glycoside derivatives and use thereof
US20050002889A1 (en) * 2003-04-08 2005-01-06 L'oreal Compositions suitable for topical application to the skin
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