EP2010137A1

EP2010137A1 - Use of galactose c-glycoside derivatives as protective agent and/or t lymphocyte activator

Info

Publication number: EP2010137A1
Application number: EP07727851A
Authority: EP
Inventors: Lionel Breton
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2006-04-07
Filing date: 2007-04-05
Publication date: 2009-01-07
Also published as: WO2007116021A1; CN101466350A; FR2899468B1; FR2899468A1; US20090325890A1

Abstract

The invention relates to the use of at least one galactose C-glycoside derivative of general formula (I) as protective agent and/or as activity or proliferation promoter for T-lymphocyte cells of the gamma-delta type (γδT cells) in a composition comprising a cosmetically or pharmaceutically acceptable medium. The composition is of application in promoting skin tissue repair, rebalancing epidermal proliferation and differentiation disorders occurring on lack of sleep, improving appearance of the hair and limiting hair loss.

Description

Use of galactose-derived C-glycosides as a protective agent and / or activator of γδT lymphocytes

The present invention relates to the use of at least one C-glycoside derivative of galactose of general formula (I)

as a protective and / or stimulating agent for the activity and / or proliferation of gamma-delta T cell lymphocyte cells (γδT cells) in a composition containing a cosmetically or pharmaceutically acceptable medium. The composition will find applications to promote the tissue repair of the skin, to rebalance epidermal proliferation and differentiation disorders that appear with lack of sleep, to improve the appearance of the hair and limit hair loss.

Human skin consists of a superficial compartment, the epidermis and a deep compartment, the dermis. The epidermis is composed mainly of three types of cells which are keratinocytes (majority), melanocytes and Langerhans cells. Each of these cell types contributes, by its own functions, to the essential role played in the body by the skin, in particular the protective role of the body against external aggressions. The dermis provides the epidermis with a solid support. It is also its nurturing element. It consists mainly of fibroblasts and an extracellular matrix composed mainly of collagen, elastin and a fundamental substance. There are also leucocytes, mast cells and tissue macrophages. Finally, the dermis is crossed by blood vessels and nerve fibers.

The skin constitutes a barrier against external aggressions, in particular chemical, mechanical, and as such a number of reactions of defense against the environment (climate, ultraviolet rays, tobacco, pollution ...) and / or xenobiotics (as for example some drugs) occur at its level. In healthy subjects, cells damaged by external aggressions are eliminated by the skin's immune system. However, for example when lack of sleep, the immune system is immunocompromised and can not play its role in monitoring the skin.

Human lymphocytes are characterized by a receptor for a specific antigen (TCR, T cell receptor). 95% of the lymphocyte population consists of lymphocytes whose T-cell antigen receptors are transmembrane hetero-dimers composed of an alpha and beta (αβT) chain. Only 5% of lymphocytes express gamma and delta chains (γδT), this population was highlighted by Tonegawa et al. in 1984.

ΓδT lymphocytes are mainly located in the blood (for the Vδ2 subtype) and in the epidermis and the mucous membranes (for the resident Vδ1 subtype). They express the CD3 receptors and TCR gamma-delta receptors (respectively with two variable regions depending on their circulating localization: Vγ9Vδ2 or resident: Vγ9Vδ1) and are often CD4 (-) CD8 (-), their activation is not restricted. major histocompatibility complex (MHC) and are attributed a role of cellular homeostasis. The gamma chain is encoded by chromosome 7 and the delta chain by the 14th. ΓδT lymphocytes constitute a T lymphocyte population whose analysis of the structural characteristics has modified the knowledge on the interactions between the T cell and its antigen. The importance of the immunoregulatory functions exerted by these cells opens new perspectives in the understanding of the mechanisms that contribute to the maintenance of the homeostasis of the immune system. ΓδT lymphocytes seem to intervene very early in the regulation of innate immunity.

Recent work demonstrates that these specific T cells play an important role in epidermal homeostasis (Nature Immunology, 6.1 2005, 73-76). Indeed, the γδT lymphocytes of the skin and / or mucous membranes induce the secretion and the release of IGFI in the skin and the release of IGFI by the keratinocytes leads to a control of the epidermal homeostasis in particular, the balance between proliferation and differentiation of epidermal cells.

The skin undergoes a constant remodeling, some of these transformations observed over time, are in particular, the result of a modification of the natural secretion of the body into hormones (growth hormones, prolactin, estrogen, etc.) and growth factors (TGFα and TGFβ, EGF, IGF ...).

The role of these hormones and / or growth factors is all the more important as over time their release and impact on the target tissues decrease, the tissue growth stabilizes, while the matrix degradation amplifies, is no longer compensated by the regenerating action of these hormonal factors and / or growth.

Among these growth factors, IGFs (Insulin Growth Factors) play a major role. These factors were discovered during the exploration of the mechanism of action of growth hormone GH (Growth Hormone), which stimulates the growth of all tissues, including skin. Growth hormone (GH) consists of 191 amino acids linked in a specific sequence and is secreted by the anterior part of the pituitary gland, this secretion can be enhanced by physical exercise as well as by other factors. The biological role of GH is fundamental, not only for the growth of a young organism, but also for the maintenance of its integrity in adulthood. GH acts on the peripheral organs and the brain either directly or indirectly by stimulating the synthesis of growth factors, such as insulin-like growth factors (IGF I and II) or epidermal growth factor (EGF) or that of their receptors. The direct action of GH is of the anti-insulin type by promoting lipolysis in the adipose tissue.

Through I ¹ IGF-I, GH stimulates the incorporation of amino acids in proteins, the growth of cartilage and bone (linear growth) and cell proliferation of many organs, including the skin.

Growth hormone and other somatotropic hormones, such as somatomedin C (or IGF1) are able to maintain its youthful appearance in the body. They intervene, indeed, in the management of its metabolism, determining not only the final size of the adult body but giving again, volume, tone and firmness to the organs and tissues, particularly to the muscles. In fact, growth hormone is involved in everything that provides a good self-image and a positive mind. It strengthens the body and makes the back straighter, developing the muscles of the shoulders and pelvis. It also decreases fat, especially in the belly, increases libido and sexual energy, regrowth and hair coloring, as well as elasticity of the skin. In a way that may be less apparent but equally beneficial, its effects can be seen in better resistance to effort, less prolonged sleep and more profitable, balanced blood pressure, better visual, auditory and cerebral acuity.

In all mammals studied, including humans, GH is pulsatile secretion and this character is a determining factor for a large number of biological effects of the hormone.

The causes of age-related GH decline are poorly understood. In men, from puberty, we observe a decrease in the secretion of GH of the order of 10% every ten years. During aging, loss of muscle mass, accumulation of adipose tissue, bone demineralization, loss of tissue regeneration capacity are concomitant with decreased GH secretion. The latter favors an increased catabolism and anabolism ratio, thus leading to a situation of imbalance that worsens the effects of aging. Additional factors, such as age-related weight gain or obesity, steroid hormone levels, lack of sleep, or some level of tissue resistance to GH may also be important .

At the same time, there is a notable decrease in the quality of sleep with age (decrease in slow wave sleep, paradoxical sleep and increase in waking periods and duration interrupting sleep phases). The first phenomenon of aging is a marked decline in deep sleep (SWS), which can occur as early as age 36 and is replaced by lighter sleep. The transition from midlife to late age is then associated with a decrease in the amount of sleep and duration of the paradoxical phase (rapid eye movement or REM) and deep sleep (non-REM). Statistics show that the population affected by sleep disorders totals 93 million in North America, Europe and Japan.

It is conceivable that lack of sleep or age-related decline in sleep quality contributes to hormonal changes and their metabolic consequences. Indeed, pharmacological treatments tending to increase slow-wave sleep also cause an increase in the secretion of GH.

Growth hormone deficiency results in physical symptoms: loss of hair, fine hair, thinned lips and jawbone, dehydrated skin, belly during, fat pads in the knees ... and psychological symptoms: permanent fatigue, difficulty controlling emotions, exhaustion after physical exertion, low self-esteem, depression ...

The levels of growth hormone circulating in the blood stimulate the production, from the liver, of another hormone, NGF1 (insulin like growth factor 1), whose role as a mediator allows the growth hormone to develop its positive effects. Measurement of IGFI, also called Somatomedin C, is considered safer than that of GH, virtually undetectable in humans. The liver is the most important site for producing IGFs, but many cells are able to produce IGFs. Two types are classically described: IGF1 and IGF2. These are two peptides whose amino acid sequence is similar to that of insulin, hence their name. There are two receptors for IGFI and NGF2, respectively. The NGF1 receptor has a shared affinity with insulin. This is not the case for the NGF2 receiver. With aging, the rate of IGFs decreases to stabilize in adulthood: it is somatopause (D. Radman "Effects of human growth hormone in men over 60 years old", N. Engl J. Med 1990, July 323 (1): 1-6).

It is known in the state of the art that IGFI alone stimulates the proliferation of keratinocytes (Neely EK - Insulin-like growth factors are mitogenic for human keratinocytes and squamous cell carcimona - J Invest Dermatol 1991 Jan; 96 (1) : 104-10). With regard to fibroblasts, it is also known that IGFI stimulates the synthesis of GAGs, and the synthesis of collagen. In addition, studies have shown a significant participation of IGFs in healing. Finally, a study conducted in vivo in humans has shown that a percutaneous treatment with IGF1 for a month resulted in an argumentation of cutaneous thickness.

It has also been shown that the decrease in IGFI expression is associated with increased hair loss (Tang et al, 2003, J. Am Dermatol Acad, Aug; 49 (2): 229-33).

The Applicant has demonstrated that galactose-derived C-glycoside compounds of general formula (I) stimulates and / or protects γδT cells and that thus this extract can induce the secretion and release of IGFI in the skin. This control of the release of IGFI by keratinocytes contributes to the maintenance of epidermal homeostasis which regulates in particular the equilibrium between proliferation and differentiation of epidermal cells.

Thus, according to a first of its objects, the present invention relates to the use of at least one compound of general formula (I):

in which,

X represents a group chosen from: -CO-, -CH (NR ₁ R ₂ ) -, -CHR ¹ -, -C (= CHR ') -; R represents an alkyl, perfluoroalkyl, linear or branched hydrofluoroalkyl chain, saturated or unsaturated, a cycloalkyl, cycloperfluoroalkyl or cyclohydrofluoroalkyl ring, comprising from 1 to 18 carbon atoms, a phenyl radical, said chain, said ring or said radical possibly being interrupted by one or more heteroatoms selected from oxygen, sulfur, nitrogen, silicon, and optionally substituted with at least one radical selected from -OR'i, -SR ' ¹ _! -NR ¹¹¹ ^ ₂ , -COOR " ₂ , -CONHR '" ₂ , -CN, halogen, perfluoroalkyl, hydrofluoroalkyl and / or at least one optionally substituted cycloalkyl, aryl, heterocyclic radical;

R ', R ₁ , R ₂ , which are identical or different, have the same definition as that given for R, and may also represent a hydrogen and a hydroxyl radical; - R ' ₂ , R'" ₂ , identical or different, represent a hydrogen atom, a radical chosen from a linear or branched, saturated or unsaturated alkyl, hydroxyl, perfluoroalkyl and / or hydrofluoroalkyl radical, comprising from 1 to 20 carbon atoms; R'i, R "i, R" _2, R '"i, identical or different, represent a hydrogen atom, a radical chosen from a linear or branched alkyl, perfluoroalkyl and / or hydrofluoroalkyl radical, saturated or unsaturated, comprising from 1 to 20 carbon atoms; with the following restrictions:

- R'2 and R '"1 can not be simultaneously a hydroxyl;

- R1 and R2 can not be simultaneously a hydroxyl radical; to maintain and / or restore the balance between proliferation and differentiation of epidermal cells.

Compounds of general formula (I) will be preferred as defined above such as:

R represents an alkyl chain, linear or branched, saturated or unsaturated, a cycloalkyl ring, comprising from 1 to 10 carbon atoms, a phenyl radical, said chain, said ring or said radical possibly being substituted by at least one radical chosen from -OR ¹ ,, -NR " ¹ , ^, -COOR" ₂ , -CONHR '"₂; R '_2>R' ^M 2, identical or different, represent a hydrogen atom, a radical chosen from a linear or branched, saturated or unsaturated, hydroxyl, hydroxyl radical comprising from 1 to 8 carbon atoms;

R'i, R "i, R ^M 2, R"'i, which are identical or different, represent a hydrogen atom, a radical chosen from a linear or branched, saturated or unsaturated alkyl radical comprising from 1 to 8 carbon atoms, carbon.

More particularly, the compounds of general formula (I) as defined above are further preferred such that: X represents a group chosen from: -CO-, -CH (NR ₁ R ₂ ) -, -CHR ';

R represents an alkyl chain, linear or branched, saturated or unsaturated, a cycloalkyl ring, comprising 1 to 10 carbon atoms, a phenyl radical.

The C-glycoside compounds which can be used according to the invention represent a sub-family of the C-glycoside derivatives described in EP 1 345 919, they can be prepared according to the process described in this document.

Among the C-glycoside derivatives of formula (I) used according to the invention, the following are particularly preferred: 1- (C-β-D-galactopyranosyl) propan-2-one;

Compound 2. phenyl-2- (C-β-D-galactopyranosyl) -1-hydroxy-ethane;

Compound 3. 1- (C-β-D-galactopyranosyl) -undecan-2-one;

Compound 4. 1- [2- (3-Hydroxypropylamino) propyl] -C-β-D-galactopyranose;

Compound 5. 3-methyl-4- (C-β-D-galactopyranosyl) -2-butenoic acid ethyl ester

Compound 6. Ethyl (2E) -3-methyl-4 - [(2S, 3R, 4R, 5R, 6R) -3,4,5-trihydroxy-6

(Hydroxymethyl) tetrahydro-2H-pyran-2-yl] but-2-enoate.

The use of a protector and / or stimulator of γδT lymphocytes of the skin and / or mucous membranes leads to the increased release of IGFI by epidermal cells and promotes the physiological proliferation of keratinocytes and / or decreases epidermal differentiation.

Given that the release of IGFI is dependent on the secretion of GH and prolactin and that these hormones are released pulsatile during the sleep phase and only during the sleep phase (it s' alternates between waking / sleeping and not alternating day / night), the present invention also relates to the cosmetic use of at least one compound of general formula (I) for mimicking the effect of sleep on renewal epidermal cell or to either supplement the effect of sleep on the skin during a normal rest or, to supplement the dysfunction of skin epidermal functions that may occur during a lack of sleep. The use according to the invention will thus more specifically aim to mimic the effects of sleep on epidermal cellular renewal to prevent and / or correct the cutaneous effects characteristic of lack of sleep and / or to stimulate the skin during the absence of sleep and induce the renewal of epidermal cells. Thus, the use according to the invention makes it possible to prevent and / or treat the cutaneous manifestations generated by the slowing down of the renewal of the cells, thus leads to the cellular regeneration of the epidermis and improves the appearance of the surface of the skin. The consequences of this activity is that the use of a compound of general formula (I) according to the invention on a subject in lack of sleep makes it possible more particularly to treat drawn and / or hollow lines, to even out the complexion.

According to a second subject, the present invention relates to a cosmetic treatment method for erasing the cutaneous signs of fatigue by stimulating the regeneration of epidermal cells, characterized in that it comprises the application to the face of at least one compound of general formula (I).

The use of at least one compound of general formula (I) also makes it possible to prevent and / or treat hair disorders such as a change in the density, the quantity or the quality of the hair, as a consequence, for example, of slowing down, stopping growth or falling hair follicles.

Thus according to another of its subject, the present invention relates to the use of at least one compound of general formula (I) for preventing the thinning of the keratinous fiber and / or inducing the growth of hair and / or hair to induce regrowth of hair or denser hair.

Also, the invention also relates to the use of at least one compound of general formula (I) as an agent for inducing and / or stimulating the growth of keratin fibers, human hair or hairs, in particular human and / or braking their fall and / or increase their density.

By increasing the density of the keratinous fibers, and in particular the capillary density, it is intended to increase the number of keratin fibers, in particular the hair, per cm ² of skin such as the scalp. Thus, another use according to the invention relates to hair treatment compositions (shampoo, lotion, masks, etc.) for limiting and / or preventing hair loss and thus treating alopecia of any nature whatsoever and / or promote the growth of healthy hair.

The cosmetic use according to the invention of compound of general formula (I) can be carried out using a cosmetic composition for the care and / or makeup of keratinous fibers.

The invention also applies to keratinous fibers of mammals of the animal species (dog, horse or cat for example).

The human keratinous fibers to which the invention applies are in particular the hair, the eyebrows, the eyelashes, the beard and mustache hairs. More specifically, the invention is applicable to human hair and / or eyelashes.

The subject of the present invention is also a process for the cosmetic treatment of human keratinous fibers and / or the skin from which said fibers, including the scalp, emerge, intended in particular to stimulate the growth of human keratinous fibers such as the hair and the cilia of being human and / or curbing their fall, characterized in that it consists in applying to the human keratin fibers and / or the skin from which said fibers emerge, a cosmetic composition comprising an effective amount of at least one compound of general formula (I), to leave it in contact with the keratinous fibers and / or the skin from which said fibers emerge, and possibly to rinse the keratinous fibers and / or said skin. This treatment method has the characteristics of a cosmetic process insofar as it makes it possible to improve the esthetics of the keratinous fibers and in particular the hair and the eyelashes by giving them a greater vigor and an improved appearance. In addition, it can be used daily for several months, without a medical prescription. More specifically, the subject of the present invention is a process for the cosmetic care of human hair and / or scalp, with a view to improving their state and / or their appearance, characterized in that it consists in applying to the hair and or or the scalp, a cosmetic composition comprising at least one compound of general formula (I), to leave it in contact with the hair and / or the scalp, and possibly to rinse the hair and / or the scalp.

The subject of the invention is also a process for the cosmetic care and / or makeup of these human eyelashes, with a view to improving their state and / or their appearance, characterized in that it consists of applying a mascara composition comprising at least one compound of general formula (I) and leaving it in contact with the eyelashes. This mascara composition can be applied alone or as an undercoat of a conventional pigmented mascara and removed as a conventional pigmented mascara.

The compositions used according to the invention can be administered orally, enterally or else topically, preferable topical administration.

In the case of oral administration, the compositions may be in any suitable form such as an oral solution, capsules, dragee, soft or hard capsule, tablets to swallow or chewable, granules to dissolve, syrup, solid or liquid food ...

The composition may also be in the galenical forms conventionally used for topical application and especially in the form of lotion or serum-type dispersions, of liquid or semi-liquid consistency emulsions of the milk type, obtained by dispersion of a fatty phase. in an aqueous phase (O / W) or conversely (W / O), or suspensions or emulsions of soft, semi-solid or solid consistency of the cream or gel type, or multiple emulsions (W / O / W or H / E / H), microemulsions, nanoemulsions, vesicular dispersions of ionic and / or nonionic type, or wax / aqueous phase dispersions. These compositions are prepared according to the usual methods. It may also be in the form of a transdermal system allowing active or passive release of the active (s) by transdermy, for example patch or gel patch (hydrogel).

The composition used according to the invention may thus constitute a composition for treating or caring for the skin (including the scalp), keratin fibers (hair, eyelashes, eyebrows), nails or lips, or a protective composition. solar or artificial tanning, or a cleanser or makeup remover of the skin, hair, eyebrows or eyelashes, a deodorant product or a perfume compound. It is then generally not colored or weakly colored, and it may optionally contain cosmetic or dermatological active ingredients. It can then be used as a skin or lip care base (lip balms, protecting the lips from cold and / or sun and / or wind) as a day or night care cream for the skin of the skin. face and / or body. It may, in addition, be in the form of shampoo treatment or not, dye or not, and conditioner. The composition used according to the invention may also constitute a colored cosmetic composition and in particular a makeup composition for the skin, keratinous fibers (hair or eyelashes) and / or mucous membranes, in particular a foundation, a blush, a makeup with cheeks or eyes, a concealer compound in a stick, a lipstick or a lip gloss, optionally having care or treatment properties. Preferably, it may be a colored makeup composition (beige or green) intended to correct the color of the complexion.

Depending on the purpose of the composition used according to the invention, it may also include active agents which will be chosen by those skilled in the art so that they do not harm the effect of the compounds according to the invention.

In the context of the use according to the invention for preventing and / or treating capillary disorders, the compositions will be for cosmetic use and in particular for topical application to the skin and keratinous fibers, and more especially to the scalp, the hair and eyelashes, they can be in any known galenic forms adapted to the mode of use, for example, those mentioned above.

In particular, the composition for application to the scalp or the hair may be in the form of a hair care lotion, for example a daily or biweekly application, a shampoo or a hair conditioner, in particular Particular application bi-weekly or weekly, a liquid soap or solid daily scalp cleansing, a product shaping the hairstyle (lacquer, product for setting, styling gel) , a masking mask, a cream or a foaming gel for cleaning the hair. It can still be in the form of hair dye or mascara to be applied by brush or comb.

Furthermore, for an application on the eyelashes or the hairs, the composition to which the invention applies may be in the form of a mascara, pigmented or not, to be applied to the brush on the eyelashes or on the hairs beard or mustache.

According to a particular embodiment, the composition according to the invention is in the form of hair cream or lotion, shampoo or hair conditioner, hair mascara or eyelash. According to a particular embodiment of the invention, it is possible to associate with the compound of general formula (I) at least one additional capillary active compound promoting the regrowth and / or limiting the fall of keratinous fibers and in particular the hair.

Said hair active may be chosen from:

anti-seborrheic agents such as certain sulfur amino acids, 13-cis retinoic acid, cyproterone acetate;

agents for controlling squamous conditions of the scalp (films) such as zinc pyrithione, selenium disulphide, climbazole, undecylenic acid, ketoconazole, piroctone olamine (octopirox) or ciclopirocton (ciclopirox);

the active agents stimulating the regrowth and / or promoting the slowing down of the hair loss, it may more particularly be mentioned without limitation:

^* Nicotinic acid esters, especially including tocopheryl nicotinate, benzyl nicotinate and alkyl nicotinates C- | -Cβ as methyl or hexyl nicotinates;

^* Pyrimidine derivatives such as 2,4-diamino-6-piperidinopyrimidine 3-oxide or "Minoxidil" described in the patents US 4,139,619 and US 4,596,812; Aminexil or 2,4 diamino pyrimidine 3 oxide described in WO96 / 09048; ^* Agents both lipoxygenase inhibitors and inducers of cyclooxygenase, or inducers of cyclooxygenase promoting hair regrowth such as those described by the Applicant in European patent application EP 0648488;

antibiotic agents such as macrolides, pyranosides and tetracyclines, and in particular Erythromycin; Cinnarizine, Nimodipine and Nifedipine;

hormones, such as estriol or analogues, or thyroxine and its salts;

antiandrogenic agents, such as oxendolone, spironolactone, diethylstilbestrol and flutamide;

- cromakalim and nicorandil.

The composition according to the invention can be applied to the alopecic areas of the scalp and hair of an individual, and possibly left in contact for several hours and possibly rinsed. EXAMPLE 1 Demonstration of the Induction of the Proliferation of γδT Lymphocytes by the C-glycoside Derivatives of the Invention

The proliferation activity of γδT lymphocytes is tested as follows: human peripheral blood cells are cultured in the presence of an RPMI culture medium supplemented with L-Glutamine (2 mM), penicillin / streptomycin (50μg / 50Ui / ml), and fetal calf serum (10%). The C-glycoside derivatives are added at different concentrations (10 to 0.05mM) as well as phytohemagglutin (PHA at 5 ^* G / ml), a positive control of lymphocyte proliferation. After 3 days of culture the proliferation is revealed by BrdU labeling.

The results obtained are as follows:

The tested derivative has a high capacity for proliferation of human lymphocytes at concentrations greater than or equal to 0.5 mM.

EXAMPLE 2 Compositions According to the Invention

Cleansing lotion for the face

Compound 3 1, 00 Strontium chloride 5.00 Antioxidant 0.05 Isopropanol 40.00 Preservative 0.30 Water qs 100%.

Gel for the facial care

Compound 1 5,00 Vichy thermal water 10,00 Polymer thickening 1,00 Antioxidant 0.05 lsopropanol 40.00

Conservative 0.30

Water qs 100%.

"Sleeping" restorative cream

Compound δ 1, 00

Glycerol stearate 2.00

Polysorbate 60 (Tween 60 sold by the company ICI) 1, 00 stearic acid 1, 40

Triethanolamine 0.70

Carbomer 0.40

Liquid fraction of shea butter 12.00

Perhydrosqualene 12.00 Antioxidant 0.05

Conservative 0.30

Water qs 100%

Wax / Water Mascara - Beeswax 6.00%

- Paraffin wax 13.00%

- Hydrogenated jojoba oil 2.00%

- Water-soluble film-forming polymer 3.00%

Triethanolamine stearate 8.00% - compound 5 1.00%

- Black pigment 5.00%

- Conservative qs

- Water qs 100.00%

This mascara is applied on eyelashes as a classic mascara with a mascara brush.

Claims

1. Use of at least one compound of general formula (I)

in which,

X represents a group chosen from: -CO-, -CH (NR ₁ R ₂ ) -, -CHR ¹ -, -C (= CHR ') -,

R represents a linear or branched, saturated or unsaturated alkyl, perfluoroalkyl, hydrofluoroalkyl chain, a cycloalkyl, cycloperfluoroalkyl or cyclohydrofluoroalkyl ring, comprising from 1 to 18 carbon atoms, a phenyl radical, said chain, said ring or said radical possibly being interrupted; by one or more heteroatoms selected from oxygen, sulfur, nitrogen, silicon, and optionally substituted with at least one radical selected from -OR'i, -SR ' ¹ _! -NR ¹¹¹ ^ ₂ , -COOR " ₂ , -CONHR '" ₂ , -CN, halogen, perfluoroalkyl, hydrofluoroalkyl and / or at least one optionally substituted cycloalkyl, aryl, heterocyclic radical; - R ', R ₁ , R ₂ , identical or different have the same definition as that given for R, and may also represent a hydrogen and a hydroxyl radical; R ' ₂ , R'" ₂ , which may be identical or different, represent a hydrogen atom, a radical chosen from a linear or branched, saturated or unsaturated alkyl, hydroxyl, perfluoroalkyl and / or hydrofluoroalkyl radical comprising from 1 to 20 atoms carbon, R'i, R "i, R" _2, R '"i, identical or different, represent a hydrogen atom, a radical selected from a linear or branched alkyl, perfluoroalkyl and / or hydrofluoroalkyl, saturated or unsaturated, comprising from 1 to 20 carbon atoms; with the following restrictions:

- R'2 and R''1 can not be simultaneously a hydroxyl - R1 and R2 can not be simultaneously a hydroxyl radical, to maintain and / or restore the balance between proliferation and differentiation of epidermal cells.

2. Use according to claim 1, characterized in that the compounds of formula (I) are such that:

X represents a group chosen from: -CO-, -CH (NR ₁ R ₂ ) -, -CHR'-, -C (= CH R ") -; R represents a linear or branched, saturated or unsaturated alkyl, perfluoroalkyl, hydrofluoroalkyl chain, a cycloalkyl, cycloperfluoroalkyl or cyclohydrofluoroalkyl ring, comprising from 1 to 14 carbon atoms, a phenyl or benzyl radical, the said chain, said ring or said radical being optionally being interrupted by one or more hetero atoms selected from oxygen, sulfur, nitrogen, silicon, and optionally substituted by at least one radical selected from -OR'i, -SFT ₁ , -NR ¹ ", ^ , -COOFT ₂ , -CONHFT ₂ , -CN, halogen, perfluoroalkyl, hydrofluoroalkyl and / or at least one optionally substituted cycloalkyl, aryl, heterocyclic radical; R ', R ₁ , R ₂ , which are identical or different, have the same definition as R, and may also represent a hydrogen and a hydroxyl radical;

R "has the same definition as R, and may also represent a hydroxyl radical; R ' ₂ , R'" ₂ , which may be identical or different, represent a hydrogen atom, a radical chosen from an alkyl, hydroxyl, perfluoroalkyl and / or or linear or branched, saturated or unsaturated hydrofluoroalkyl, comprising from 1 to 14 carbon atoms;

R'i, R "i, R" _2, R "'i, identical or different, represent a hydrogen atom, a radical chosen from a linear or branched, saturated or unsaturated alkyl, perfluoroalkyl and / or hydrofluoroalkyl radical, comprising from 1 to 14 carbon atoms, with the limitations (i) R1 and R2 can not be simultaneously a hydroxyl radical, (ii) R'2 and R '"1 can not be simultaneously a hydroxyl radical and (iii) when R is alkyl with 2 or 3 carbon atoms, then R can not be substituted with a -COOR " _{2 group} .

3. Use according to claim 1 or 2, characterized in that: - R represents an alkyl chain, linear or branched, saturated or unsaturated, a cycloalkyl ring, comprising from 1 to 10 carbon atoms, a phenyl radical, said chain, said ring or said radical being optionally substituted with at least one radical selected from -OR'-, -NR ¹¹¹ ^ ₂ , -COOR " ₂ , -CONHR '"₂; R ' ₂ , R'" ₂ , which may be identical or different, represent a hydrogen atom, a radical chosen from an alkyl, hydroxyl, linear or branched, saturated or unsaturated radical, comprising

1 to 8 carbon atoms;

R'i, R "i, R" _2, R "'i, identical or different, represent a hydrogen atom, a radical chosen from a linear or branched, saturated or unsaturated alkyl radical comprising from 1 to 8 atoms of carbon.

4. Use according to any one of claims 1 to 3, characterized in that: X represents a group chosen from: -CO-, -CH (NRiR ₂ ) -, -CHR ';

5. Use according to any one of claims 1 to 4, characterized in that the compound of general formula (I) is chosen from: Compound 1. 1- (C-β-D-galactopyranosyl) propan-2-one; Compound 2. phenyl-2- (C-β-D-galactopyranosyl) -1-hydroxy-ethane; Compound 3. 1- (C-β-D-galactopyranosyl) -undecan-2-one; Compound 4. 1- [2- (3-Hydroxypropylamino) propyl] -C-β-D-galactopyranose;

Compound 5. 3-methyl-4- (C-β-D-galactopyranosyl) -2-butenoic acid ethyl ester; Compound 6. Ethyl (2E) -3-methyl-4 - [(2S, 3R, 4R, 5R, 6R) -3,4,5-trihydroxy-6

(Hydroxymethyl) tetrahydro-2H-pyran-2-yl] but-2-enoate.

6. Use according to any one of claims 1 to 5, for mimicking the effects of sleep on epidermal cell renewal.

7. Use according to claim 6 for correcting the cutaneous effects caused by lack of sleep.

8. Use according to claim 6 or 7, for inducing the renewal of epidermal cells.

9. Use according to any one of claims 6 to 8 for inducing cell regeneration of the epidermis.

10. Use according to any one of claims 6 to 9, for improving the appearance of the surface of the skin and / or treating drawn or hollowed lines and / or uniformity of the complexion.

1. Use according to any one of claims 1 to 5, for preventing the thinning of the keratinous fiber and / or inducing the growth of hair and / or hair.

12. Use according to claim 1 1, to induce the regrowth of hair or denser hairs.

13. Use according to any one of claims 1 to 5 for preventing and / or treating hair loss and / or hair.

14. Use according to claim 13 for preventing and / or treating alopecia.

15. Use according to any one of claims 11 to 14, characterized in that the compound or compounds of general formula (I) is associated with at least one active agent selected from the anti-fall agent and / or activator of regrowth. hair and hair.

16. A cosmetic treatment method for erasing the cutaneous signs of fatigue by stimulating the regeneration of epidermal cells, characterized in that it comprises the application to the face of at least one compound of general formula (I) according to one of the following: any of claims 1 to 5.

Process for the cosmetic treatment of human keratinous fibers and / or the skin from which said fibers, including the scalp, emerge, intended to stimulate the growth of human keratin fibers and / or to slow down their fall, characterized in that 'it consists :

to be applied to the human keratinous fibers and / or the skin from which said fibers emerge, a cosmetic composition comprising at least one compound of general formula (I) according to any one of Claims 1 to 5,

to leave it in contact with the keratinous fibers and / or the skin from which the said fibers emerge, and

optionally, rinsing the keratinous fibers and / or said skin.