FR2906245A1 - New hydroxyl diamides useful as skin moisturizer for non-therapeutic care and/or makeup of the skin, for the treatment of dry skin - Google Patents

Abstract

Hydroxyl diamides (I) and their salts, optical isomers and solvates, are new. Hydroxyl diamides (I) of formula (R3O-CH2-CH(OR2)-CH(OR2)-C(O)-N(R1)-L-N(R1)-C(O)-CH(OR2)-CH(OR2)-CH2-OR3), and their salts, optical isomers and solvates, are new. R1H, 1-8C linear alkyl or 3-8C branched alkyl, preferably H; either R2H or 1-6C linear alkyl, preferably H; or 2R2isopropylidene; R3H; and L : divalent hydrocarbon i.e. 2-6C linear, 3-6C branched or 5-8C cyclic, comprising OH group, preferably 1-3 OH groups, preferably -CH2-CHOH-CH2-, -CH2-CHOH-CHOH-CH2 or hexane moieties of formula (II) or (III). An independent claim is included for a composition comprising (I) in a medium. [Image].

Description

The present invention relates to novel hydroxyl diamides

  useful in the field of skin care and especially as a moisturizing agent of the skin, as well as cosmetic or dermatological compositions containing them.

  The Stratum Corneum, which forms the interface with the external desiccant environment, has the particular function of delaying the excessive loss of water from the deeper layers of the epidermis. The Stratum Corneum also protects against mechanical aggression and the passage of chemicals and foreign microorganisms. It is also the first defense against UV radiation.

  The Stratum Corneum, 10 m thick, consists of vertically stacked corneocytes surrounded by a matrix of lipid-enriched membranes. Thus, it is a two-compartment system that can be compared to a brick wall, consisting of anucleate cells (bricks) and intercellular lamellar membranes (cement). Urea is one of the ingredients widely used in moisturizing formulas. However, it can significantly alter the skin barrier by increasing the Water Insensitive Loss (PIE), which significantly decreases the barrier function of the Stratum Corneum. Glycerol, another reference active ingredient in this field, has the disadvantage of making the formulations sticky when used at high concentration. There is therefore a need to find alternative solutions in the field of hydration of the skin. The inventors have discovered that certain amides of general formula (I) described below are good moisturizing agents and have a beneficial effect in terms of elasticity of Stratum Corneum. Thus, the subject of the present invention is novel compounds of the following general formula (I): ## STR2 ## in which: R 1 represents a hydrogen atom or a linear C 1 -C 8 alkyl radical; or branched C3-C8; R2 represents a hydrogen atom or a linear (C1-C6) saturated alkyl radical, the 2 adjacent R2 groups may together form an isopropylidene group; R3 represents a hydrogen atom; L represents a divalent linear C 2 -C 6 or branched C 3 -C 6 or cyclic C 5 -C 8 hydrocarbon group and comprising at least one -OH group, in particular from 1 to 3 OH groups; and their salts, optical isomers and solvates. The subject of the present invention is also a composition, in particular a cosmetic or dermatological composition, comprising in a physiologically acceptable medium a compound of formula (I) as described above. The present invention also relates to a cosmetic treatment method for the non-therapeutic care and / or make-up of the skin, characterized in that it comprises the application to the skin of a cosmetic composition comprising, in a physiological medium, 20, a compound of formula (I) as defined above. The invention further relates to the cosmetic use of a compound of general formula (I) as described above as a moisturizing agent of the skin.

Advantageously, the compounds of formula (I) described above have the following stereochemistry: OR2 R1 R1 OR2 NL ~ N = (R) (R) OR3 OR2OOR2 (I ') The term alkyl, in the context of the The present invention means a linear or branched, saturated, cyclic or non-cyclic hydrocarbon chain. Among the alkyl groups which are suitable for carrying out the invention, mention may especially be made of the methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, -CH 2 -t-butyl and pentyl groups. hexyl, heptyl, octyl. The salts of the compounds described in the present invention include conventional non-toxic salts of said compounds such as those formed from organic or inorganic acids. By way of example, mention may be made of the salts of mineral acids, such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid and boric acid. Mention may also be made of organic acid salts, which may comprise one or more carboxylic acid, sulphonic acid or phosphonoic acid groups. It may be linear, branched or cyclic aliphatic acids or aromatic acids. These acids may furthermore comprise one or more heteroatoms chosen from O and N, for example in the form of hydroxyl groups. These include propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid. The solvates acceptable for the non-therapeutic use of the compounds described in the present invention include conventional solvates such as those formed in the last step of preparing said compounds due to the presence of solvents. By way of example, mention may be made of solvates due to the presence of water or of linear or branched alcohols, such as ethanol or isopropanol. The preferred compounds of formula (I) are those for which: R1, R2 and R3 denote a hydrogen atom; L denotes a divalent radical chosen from: ## STR1 ## As preferred compounds of formula (I), the following compounds may be mentioned: Compound Structure Name (2 R, 3 R, 2'R, 3'R) -N, N '- (2- 1 OH OH 1,3-hydroxypropane diyl) bis (2,3,4 Ho HN Y OH trihydroxybutanamide) oH oOH ## STR5 ## OH 2H, (2R, 3R, 2'R, 3'R) -N, N '- [(1R, 3S, 4R, 6S) -H-OH OH 4,5,6-Trihydroxycyclohexane -1,3-Phenol OH diol] bis (2,3,4-trihydroxybutanamide) OH- (2R, 3R, 2'R, 3'R) -N, N '- [ (2S, 3S) -2,3-HOOHOH dihydroxybutane-1,4-diyl] bis (2,3,4-tetrahydroxybutanamide) (2R, 3R, 2'R, 3'R) -N, N'-OH OH -10H [(1R, 3S, 4R, 6S) -2,4,5,6-HOOH tetrahydroxycyclohexane-1,3 The compound of formula (I) for which R 2 = R 3 = H (1-diethyl] bis (2,3,4-trihydroxybutanamide) is particularly preferred. compounds Ia) can be obtained by reacting the methyl ester ee threonic acid or erythronic acid (A) (these two compounds are distinguished according to the configuration of asymmetric carbons) with a diamine H (R1) NLN (R1) H, especially in ethanol or acetonitrile, to a temperature of about 60 C.

The compounds of formula (I) in which the 2 groups taken together form an isopropylidene group and R 3 = H (compounds 1b) can be prepared by reacting the methyl ester of threonic or erythronic acid (A) with the acetone to form the isopropylidene derivative (B) which, by reacting with a H (R 1) NLN (R 1) H diamine, especially in ethanol or acetonitrile, at a temperature of about 60 ° C, leads to compound (lb). ## STR1 ## ## STR2 ## According to another embodiment of synthesis (Scheme II) ), the compounds of formula (I) for which R 2 = R 3 = H (compounds Ia) can be prepared by mixing, especially at a temperature of between 0 and 100 ° C., D-erythronolactone (C) and a diamine H ( R1) NL-N (R1) H, without solvent or in a polar solvent, protic or aprotic, such as water, ethanol, methanol or acetonitrile. Compounds of formula (I) in which both R 2 groups taken together form isopropylidene and R 3 = H (compounds 1b) can be prepared by reacting D-erythronolactone (D) isopropylidene (known compound CAS No. 25581 -41-3) with a diamine H (R1) NLN (R1) H, especially in a polar solvent, protic or aprotic, or apolar (for example dichloromethane), at a temperature between 30 and 60 C.

The synthetic modes of Scheme II make it possible to prepare compounds with R, R stereochemistry of the two asymmetric carbons. R1 R1 H1NLNuH HCOOH solvent, TCC acetone R1 OH N = (R) cR) OH OH OH R1 R1 H1 W .., L ,, NùH solvent, TC lb D Diagram II The compounds of formula (I) for which R2 = alkyl and R3 = H (compounds Ic) can be prepared by reacting D-erythronolactone (C) with an alkyl halide R2-X (X being an iodine, bromine or chlorine) in the presence of a strong base (such as sodium hydride) in an anhydrous solvent (for example tetrahydrofuran), especially at a temperature between 0 C and 40 C, to obtain the intermediate E The latter then reacts with a H (R 1) NLN (R 1) H diamine, without solvent or in a polar, protic or aprotic solvent, such as, for example, water, ethanol, methanol or acetonitrile, in particular at a temperature between 0 and 100 C. R1 R1 1) NaHHiN ~ L ~ NùH OR2 R1 R1 O R2 THF TC çOO cR> ~ N cR> the ~ N H0 ~ 4 ~ R> ~ L (R) OH 2 R2-X R20 OR2 OR2 OO OR2 solvent, TCE Schem The present invention also relates to a composition comprising, in a physiologically acceptable medium, a compound of formula (I) as described above. The composition is in particular a cosmetic or dermatological composition.

These cosmetic compositions in which the compounds (I) can be used are useful for the non-therapeutic care and / or the make-up of the skin. They are particularly useful for moisturizing the skin. They can show their effectiveness as a non-therapeutic skin care treatment, namely as a preventive measure. They can also be used as a non-therapeutic treatment of the skin after a manifestation of disorders of skin hydration. In this second case, this manifestation of disorders of the hydration of the skin is preferably independent of irritation caused by contacting the skin with a bleaching agent, in particular chlorine bleaching agent, for example based on hypochlorite.

Finally, the cosmetic compositions of the invention are preferably formulated under non-alkaline conditions, even more preferably at a pH close to that of the skin, for example at a pH of between 5 and 6. The compounds of formula (I) may be present in the cosmetic compositions in amounts ranging from 0.01 to 20%, preferably from 0.01 to 15% and even more preferably from 0.1 to 10% by weight relative to total weight of the cosmetic composition. The compositions used according to the invention contain a physiologically acceptable medium, that is to say, compatible with cutaneous tissues such as the skin and the scalp. This physiologically acceptable medium may more particularly consist of water and optionally of a physiologically acceptable organic solvent chosen, for example, from lower alcohols containing from 1 to 8 carbon atoms and in particular from 1 to 10 carbon atoms. 6 carbon atoms, such as ethanol, isopropanol, propanol, butanol; polyethylene glycols having from 6 to 80 ethylene oxide units and polyols such as propylene glycol, isoprene glycol, butylene glycol, glycerine and sorbitol.

The compositions according to the invention may be in any of the galenical forms conventionally used for topical application and especially in the form of aqueous, hydroalcoholic, oil-in-water (O / W) or water-in-oil (E) solutions. / H) or multiple (triple: W / H / E or H / E / H), aqueous gels, or dispersions of a fatty phase in an aqueous phase using spherules, these spherules being polymeric nanoparticles such as nanospheres and nanocapsules or lipid vesicles of ionic and / or nonionic type (liposomes, niosomes, oleosomes). These compositions are prepared according to the usual methods. In addition, the compositions used according to the invention may be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste or a mousse. They may optionally be applied to the skin in the form of an aerosol. They may also be in solid form, for example in the form of a stick.

When the composition used according to the invention comprises an oily phase, it preferably contains at least one oil. It may also contain other fatty substances. As oils that can be used in the composition of the invention, mention may be made, for example, of: hydrocarbon-based oils of animal origin, such as perhydrosqualene; Hydrocarbon oils of plant origin, such as liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms, for example triglycerides of heptanoic or octanoic acids, or else, for example, sunflower, corn or soybean oils. , squash, grape seeds, sesame, hazelnut, apricot, macadamia, arara, castor oil, avocado, triglycerides of caprylic / capric acids such as those sold by Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit Nobel, jojoba oil, shea butter oil; esters and synthetic ethers, in particular of fatty acids, such as the formula oils R1COOR2 and R1OR2 in which R1 represents the residue of a fatty acid containing from 8 to 29 carbon atoms, and R2 represents a hydrocarbon chain, branched or unbranched, containing from 3 to 30 carbon atoms, for example Purcellin oil, isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, octyl-2-dodecyl stearate, octyl-2-dodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate 40, diisostearyl malate, triisocetyl citrate; heptanoates, octanoates, decanoates of fatty alcohols; polyol esters, such as propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters such as pentaerythrityl tetraisostearate; Linear or branched hydrocarbons of mineral or synthetic origin, such as paraffin oils, volatile or not, and their derivatives, petroleum jelly, polydecenes, hydrogenated polyisobutene such as parleam oil; fatty alcohols having from 8 to 26 carbon atoms, such as cetyl alcohol, stearyl alcohol and their mixture (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol and 2-undecylpentadecanol; , oleic alcohol or linoleic alcohol; partially fluorinated hydrocarbon oils and / or silicone oils such as those described in document JP-A-2-295912; silicone oils such as volatile or non-volatile polymethylsiloxanes (PDMS) with a linear or cyclic silicone chain, which are liquid or pasty at room temperature, in particular cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, during or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenyl silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyl trisiloxanes, 2-phenylethyl trimethylsiloxysilicates, and polymethylphenylsiloxanes; - their mixtures. The term "hydrocarbon-based oil" is used in the list of oils mentioned above, any oil predominantly comprising carbon and hydrogen atoms, and optionally ester, ether, fluoro, carboxylic acid and / or alcohol groups. The other fatty substances that may be present in the oily phase are, for example, fatty acids containing from 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; waxes such as lanolin, beeswax, carnauba or candelilla wax, paraffin waxes, lignite waxes or micro-crystalline waxes, ceresin or ozokerite, synthetic waxes such as polyethylene waxes, Fischer-Tropsch waxes; silicone resins such as trifluoromethyl-C1-4-alkyldimethicone and trifluoropropyldimethicone; and silicone elastomers such as the products sold under the names KSG by Shin-Etsu, under the names Trefil, BY29 or EPSX by the company Dow Corning or under the names Gransil by the company Grant Industries. These fatty substances may be chosen in a varied manner by those skilled in the art in order to prepare a composition having the desired properties, for example of consistency or texture. According to a particular embodiment of the invention, the composition according to the invention is a water-in-oil (W / O) or oil-in-water (O / W) emulsion. The proportion of the oily phase of the emulsion can range from 5 to 80% by weight, and preferably from 5 to 50% by weight relative to the total weight of the composition.

The emulsions generally contain at least one emulsifier chosen from amphoteric, anionic, cationic or nonionic emulsifiers, used alone or as a mixture, and optionally a co-emulsifier. The emulsifiers are suitably selected according to the emulsion to be obtained (W / O or O / W). The emulsifier and the coemulsifier are generally 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. . For the W / O emulsions, examples of emulsifiers that may be mentioned include dimethicone copolyols such as the mixture of cyclomethicone and dimethicone copolyol, sold under the name DC 5225 C by Dow Corning, and alkyl dimethicone copolyols such as Laurylmethicone copolyol sold under the name Dow Corning 5200 Formulation Aid by Dow Corning and Cetyl dimethicone copolyol sold under the name Abil EM 908 by the company Goldschmidt. It is also possible to use, as surfactant of W / O emulsions, a crosslinked elastomeric solid organopolysiloxane comprising at least one oxyalkylene group, such as those obtained according to the procedure of Examples 3, 4 and 8 of US Pat. No. 5,412,004. and examples of US-A-5,811,487, including the product of Example 3 (Synthesis Example) of US-A-5,412,004. and such as that sold under the reference KSG 21 by Shin Etsu. For O / W emulsions, mention may be made, for example, as emulsifiers, of nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid and sorbitan esters; oxyalkylenated fatty acid esters (oxyethylenated and / or oxypropylenated); oxyalkylenated fatty alcohol ethers (oxyethylenated and / or oxypropylenated); sugar esters such as sucrose stearate; and mixtures thereof such as the mixture of glyceryl stearate and PEG-40 stearate.

In known manner, the cosmetic or dermatological composition of the invention may also contain adjuvants usual in the cosmetic or dermatological field, such as oils, waxes, thickeners, film-forming polymers, preservatives, perfumes, fillers, UV filters, bactericides, odor absorbers, dyestuffs, cosmetic active ingredients, plant extracts, antioxidants. The amounts of these various adjuvants are those conventionally used in the field under consideration, and for example from 0.01 to 20% of the total weight of the composition. These adjuvants, depending on their nature, can be introduced into the fatty phase and / or into the aqueous phase.

The compounds of formula (I) may be combined with one another, or with other additional skin hydrating agents different from the compounds of formula (I) described above and / or with at least one other cosmetic active ingredient.

For such an additional cosmetic active ingredient, active agents acting on the barrier function of the skin, the active agents promoting the hydration of the skin and the desquamating agents may be mentioned.

By desquamating agent is meant any compound capable of acting: either directly on desquamation by promoting exfoliation, such as 13-hydroxy acids, in particular salicylic acid and its derivatives (including n-octanoyl acid). 5-salicylic); α-hydroxy acids, such as glycolic, citric, lactic, tartaric, malic or mandelic acids; urea; gentisic acid; oligofucoses; cinnamic acid; Saphora japonica extract; resveratrol; 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 of the chelating agents for mineral salts: EDTA; N-acyl-N, N ', N', ethylene diaminetriacetic acid; Aminosulfonic compounds and in particular N- (2-hydroxyethyl) piperazine-N'-2-ethanesulfonic acid (HEPES); 2-oxothiazolidine-4-carboxylic acid derivatives (procysteine); glycine-type alpha amino acid derivatives (as described in EP-0 852 949, as well as the sodium methyl glycine diacetate marketed by BASF under the trade name TRILON M); honey 20; sugar derivatives such as O-octanoyl-6-D-maltose and N-acetyl glucosamine. Among the active agents acting on the barrier function of the skin, or promoting the hydration of the skin, mention may be made of: either the compounds acting on the barrier function, with a view to maintaining the hydration of the stratum corneum, or the compounds occlusives, in particular ceramides, sphingoid-based compounds, lecithins, glycosphingolipids, phospholipids, cholesterol and its derivatives, phytosterols (stigmasterol, 13-sitosterol, campesterol), essential fatty acids, 1-2 diacylglycerol 4-chromanone, pentacyclic triterpenes such as ursolic acid, petrolatum and lanolin; Or the compounds directly increasing the water content of the stratum corneum, such as thralose and its derivatives, hyaluronic acid and its derivatives, glycerol, pentanediol, sodium pidolate, serine, xylitol, lactate sodium, glycerol polyacrylate, ectoin and its derivatives, chitosan, oligo- and polysaccharides, cyclic carbonates, N-lauroyl pyrrolidone carboxylic acid, and Na-benzoyl-L-arginine; Or the compounds activating the sebaceous glands such as steroid derivatives (including DHEA) and vitamin D and its derivatives. The composition may be presented as a non-therapeutic care product and / or makeup, and also a lip balm. The composition according to the invention may contain a cosmetic ingredient chosen from oils, waxes, thickeners, film-forming polymers, preservatives, perfumes, fillers, UV filters, bactericides, odor absorbers, dyestuffs, cosmetic active agents, plant extracts, antioxidants, surfactants. Finally, a subject of the invention is a cosmetic treatment method for the non-therapeutic and / or for the make-up of the skin, characterized in that it comprises the application to the skin of at least one cosmetic composition or dermatological composition according to the present invention comprising at least one compound of formula (I) as defined above or a mixture thereof in all proportions.

Among the makeup-type applications that the cosmetic treatment process may consider, there may be mentioned foundations, blushers, eyeshadows, concealer and body make-up. The invention relates ultimately to the use of a compound of formula (I) as defined above for the preparation of a dermatological composition intended for the hydration of the skin and more particularly to the treatment of drought skin or treating dry skin. The following examples illustrate the invention without limiting its scope.

Example 1: Preparation of (2R, 3R, 2'R, 3'R) -N, N '- (2-hydroxypropane-1,3-diyl) bis (2,3,4-trihydroxybutanam ide) OOHH H ~ In a 25 ml bicolar topped with a condenser, 6 ml of ethanol, 350 mg of D-erythronolactone (CAS 15667-21-7) and then 150 mg were sequentially introduced. 1,3-diamino-2-hydroxypropane. The reaction medium was stirred and heated to 60 ° C. and followed by thin layer chromatography (85/15 CH 2 Cl 2 / MeOH). After addition of water, the reaction medium was passed over DOWEX 50WX8 resin (hydrogen form 100-200 mesh from Dow Cemical and in particular sold by Sigma-Aldrich) and then filtered. After concentration, the desired compound was obtained as a colorless oil with a yield of 83%. NMR (1H, 13C, DMSO d6): The spectra obtained are in agreement with the proposed structure.

40 Elemental analysis: Theoretical Theoretical 0.5 mole Measured water C / OH / ON / 0 0 / OL '/ OH / ON / 0 0 / OL' / OH / ON% O 40.55 / 6.8 / 44.1 38.4 / 7 / 8.1 38.4 / 7.1 8.6 / / 46.4 / 7.9 / 46.1 OH OH OH 2906245 Example 2: Preparation of (2R, 3R, 2 R, 3'R) -N, N '- [(1 R, 3S, 4R, 6S) -4,5,6-trihydroxycyclohexane-1,3-diyl] bis (2,3,4-trihydroxybutanamide) 12 The synthesis is carried out in the same manner as for Example 1 using 2-10 deoxystreptamine. Example 3: Preparation of (2R, 3R, 2'R, 3'R) -N, N '- [(2S, 3S) -2,3-dihydroxybutane-1,4-diyl] bis (2,3, 4-Trihydroxybutanamide) The synthesis is carried out in the same manner as for Example 1 using the (4s.5s) -4.5-20 di (aminomethyl) -2,2-dimethyldioxolane Example 4: Preparation of (2R, 3R, 2'R, 3'R) -N, N '- [(1R, 3S, 4R, 6S) -2,4,5,6-tetrahydroxycyclohexane-1, 3-diyl] bis (2,3,4-trihydroxybutanamide) The synthesis is carried out in the same way as in Example 1 using streptamine Example 5 Cosmetic Formulations Example 5.1 Cream of skin care A skin care cream composition comprising the following ingredients is prepared: 2906245 13 PHASE A Glyceryl stearate (and) PEG-100 stearate: 2.00 g Dimyristyl tartrate (and) cetearyl alcohol (and) C12- 1.50 g pareth-7 (and) PPG-25 laureth-25: Cyclohexasiloxane 5.00 g Stearyl alcohol 1.00 g PHASE B Water: QSP 100 g Pentasodium ethylene diamine tetramethylene 0.05 g phosphate: Ammonium Polyacryldimethyltauramide: 0.40 g Xanthan gum: 0.20 g PHASE C compound 1 5.00 g Glycerin 1.50 g Adenosine 0.10 g Water 3.00 g Procedure - The phase B is heated to about 75 C and incorporates Ammonium Polyacryldimethyltauramide; it is stirred until a homogeneous gel is obtained. Phase A is heated to about 75 ° C. The emulsion is made by incorporating phase A into phase B. At 40 ° -45 ° C., phase C is incorporated and stirring is maintained until cooling. full. Example 5.2 Skin Care Cream A skin care composition is prepared comprising the following ingredients: (2R, 3R, 2'R, 3'R) -N, N '- (2-hydroxypropane-1, 3-diyl) bis (2,3,4-trihydroxybutanamide) - Compound 1 3.0 0/0 Glycerol monostearate 0.8 0/0 Cetyl alcohol 2.0 0/0 Stearyl alcohol 5.0 0/0 20 - Polyoxyethylene (20 EO) stearate 3.0 0/0 Crosslinked acrylic acid (CARBOPOL 941) 0.3 0/0 Caprylic / capric triglycerides 12.0 0/0 Preservatives qs 5 2906245 Water qs 100.0% Cosmetic formulations exemplified on the skin show a good effect of hydration of the skin. Example 6: Evaluation of hydration potential A test was carried out to evaluate the hydration potential of the compounds of the invention which are formulated in a 3% aqueous solution. the Dermometer, a mechanical measure of the plasticizing effect (described by J de Rigal, JL Leveque, International Journal of Cosmetic Science, 1982, 247-260), The tests carried out were carried out under standard conditions on stratum corneum in an enclosure regulated in temperature and humidity (T = 30 C and HR = 75%). The elastic modulus measurements are performed on each control sample and then 2 hours and 20 hours after application of the treatment. The relative variation of the modulus makes it possible to appreciate the plasticizing effect of the asset on the Stratum Corneum.

Table 1: Dermometer Measurements: Relative Variation of the Stratum Corneum Modulus of Elasticity at 30 C and 75% Relative Humidity at 2 and 20 Hours after Application of the Assets Product (Mean Standard Deviation) 2H 20H Products tested at 3% in water OH OH HO, OH OH O OH -35 + / 8% -40 +/- 15% Compound 1 Control products in water Pure water -5 11% - 6 12% Urea -72 9% -83 7% Glycerol -41 12% -51 15% 25 The average and the standard deviation were calculated on 10 stratum corneum samples Compound 1 has a plasticizing effect This test shows that the compounds according to the invention have different moisturizing profiles by plasticizing the Stratum Corneum.

Claims (11)

  1. Compound of formula (I): OR2 R1 R1 OR2 R3ON L NOR3 in which: R1 represents a hydrogen atom or a linear C1-C8 or branched C3-C8 alkyl radical; R2 represents an atom of hydrogen or a linear saturated alkyl radical (C1-C6), the 2 adjacent groups R2 may together form an isopropyl-15-dene group; - R3 represents a hydrogen atom; L represents a divalent linear C2-C6 or branched C3-20 C6 or cyclic C5-C8 hydrocarbon group and comprising at least one -OH group, in particular from 1 to 3 OH groups; and their salts, optical isomers and solvates. 25   2. Compounds according to the preceding claim, characterized in that: - R1, R2 and R3 denote a hydrogen atom; L denotes a divalent radical chosen from: ## STR2 ## and their salts, optical isomers and solvates.   3. Compounds according to any one of the preceding claims, characterized in that they are chosen from: - (2R, 3R, 2'R, 3'R) -N, N '- (2-hydroxypropane- 1,3-diyl) bis (2,3,4-trihydroxybutanamide); (2R, 3R, 2'R, 3'R) -N, N '- [(2S, 3S) -2,3-dihydroxybutane-1,4-diyl] -bis- (2,3,4-trihydroxybutanamide) ); (2R, 3R, 2'R, 3'R) -N, N '- [(1 R, 3S, 4R, 6S) -4,5,6-trihydroxycyclohexane-1,3-diyl] -bis- (2,3,4-trihydroxybutanamide); (2R, 3R, 2'R, 3'R) -N, N '- [(1R, 3S, 4R, 6S) -2,4,5,6-tetrahydroxycyclohexane-1,3-diyl] - bis- (2,3,4-trihydroxybutanamide).   4. Compounds according to any one of the preceding claims, characterized in that it is (2R, 3R, 2'R, 3'R) -N, N '- (2-hydroxypropane-1,3-diyl) bis (2,3,4-trihydroxybutanamide).   5. Composition comprising in a physiologically acceptable medium, a compound of formula (I) according to any one of the preceding claims.   6. Composition according to the preceding claim, characterized in that it further contains an additional skin moisturizing agent different from the compounds of formula (I) and / or at least one active agent selected from the active agents acting on the barrier function of skin, skin-promoting active ingredients and desquamating agents.   7. Composition according to any one of claims 5 and 6, characterized in that it constitutes a cosmetic or dermatological composition.   8. Cosmetic treatment process for the non-therapeutic and / or make-up care of the skin, characterized in that it comprises the application to the skin of at least one composition according to any one of Claims 5 to 7. .   9. Method according to the preceding claim, characterized in that it is a method of moisturizing the skin.   10. Use of a compound of formula (I) as defined in any one of claims 1 to 4 for the preparation of a dermatological composition intended for the hydration of the skin and more particularly to the treatment of cutaneous dryness or the treatment of dry skin.   11. Cosmetic use of a compound of formula (I) according to any one of claims 1 to 4 as a moisturizing agent of the skin. 16 25 35 40