FR3030508A1 - 1-PHENYL (3,4-DISUBSTITUTED) 2-PHENYL (3,5-DISUBSTITUTED) ETHYLENE COMPOUNDS AND THEIR USE - Google Patents

Abstract

The present invention relates to the cosmetic use, in a composition containing a physiologically acceptable medium, of at least one compound of formula (I): in which the groups R1, R2, R3 and R4 are as defined in the description, and the isomers, salts and solvates of the compound of formula (I), to protect the skin from oxidative stress, in particular caused by exposure to UV radiation.

Description

The present invention relates to the field of photoprotective cosmetic compositions, or photoprotective products, and more particularly to compounds used as antioxidants. The present invention relates to the use of 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene compounds and their use in particular for protecting the skin and its appendages from the oxidative stress caused by a exposure to UV radiation, that is to say especially the skin, including the skin of the scalp. It relates to compositions containing, in a physiologically acceptable medium, at least one compound 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene.

Keratinous materials, and in particular the skin and its integuments, are daily exposed to sunlight. However, it is known that prolonged and / or repeated exposure of keratin materials, and in particular of the skin, to this polychromatic light is likely to induce cutaneous disorders or even superficial damage.

This is in particular due to the formation of free radicals, reactive oxygen species such as O 2 and H 0, which can damage DNA, certain lipids and / or proteins, and more generally, which induce cellular aging. These reactive species disrupt biological mechanisms by inducing oxidative stress. This contributes to the development and acceleration of cellular degeneration.

The production of reactive oxygen species thus causes damage to DNA, proteins and / or lipids, and contributes to the acceleration of aging of the cells of the skin and / or its annexes. In particular, the effects of oxidative stress affect the cellular respiration and result in an acceleration of the aging of the skin, accompanied in particular by a, the early formation of wrinkles or fine lines, a loss of softness, flexibility and elasticity of the skin. Thus, UV radiation induces a phenomenon called "photo-aging" of the skin and / or its integuments, which includes as symptoms the appearance of wrinkles / fine lines, a loss of radiance and a loss of firmness. appearance of a roughness of the skin.

The effects of oxidative stress are also manifested by a decrease in the vigor of the hair and / or a deterioration of the appearance of these, in particular the hair can have a dull aspect.

Antioxidants are used in cosmetics to fight free radicals. The role of antioxidants is to capture and neutralize free radicals by converting them into subspecies, safe for keratin materials. Antioxidants can therefore be used in various fields such as anti-aging cosmetics, protection against oxidative stress and in particular that caused by exposure to the sun. Many antioxidants are already known. These include vitamin E (alpha tocopherols and isomers), vitamin C (ascorbic acid) and its derivatives, carotenoids, aminoindoles, melatonin, ubiquinone, coenzyme Q, green tea, thiols and their derivatives (Glutathione, N-acetylcysteine), procyanidolic oligomers (OPC), flavonoids, catechins including epicatechin and its gallic derivatives, polyphenols such as tyrosol, hydroxytyrosol, sesamol, carnosol, gamma orizanol, acids such as dihydrolipoic acid, uric acid, ferulic acid, caffeic acid, rosemarinic acid, carnosic acid.

However, there is a need to identify novel compounds having antioxidant properties, which make it possible in particular to protect keratinous substances (especially the skin of the scalp and / or the integuments) of individuals against the harmful effects of oxidative stress. induced by the sun's rays. We therefore understand the need for products that reduce or even inhibit the phenomenon of oxidative stress following the exposure of the skin, including the scalp, UV. In this respect, the Applicant has shown, surprisingly and unexpectedly, that certain compounds of 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene have the property of preventing or at least of to reduce the production of reactive oxygen species which is induced by the exposure of the skin cells to UV radiation, and thus to protect the skin, the scalp and the integuments such as hair, eyelashes and nails, from oxidative stress, particularly caused by exposure to UV radiation. The present invention relates to the cosmetic use, in a composition containing a physiologically acceptable medium, of at least one 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene compound such as defined herein, or a salt or solvate or optical isomer, stereoisomer, or diastereoisomer of said compound, to protect the skin, including the scalp, from oxidative stress caused by exposure to UV radiation.

In particular, the 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene defined in the present description can be used to cosmetically treat the skin, including the scalp, against oxidative stress caused by exposure to UV radiation.

By "prevention" or "prevention" is meant according to the invention the fact of reducing the risk of occurrence or slowing the occurrence of a given phenomenon, namely, according to the present invention, the cutaneous signs of photoaging. The invention also relates to a composition comprising, in a physiologically acceptable medium, at least one 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene compound of formula (I) as defined in this description. A composition according to the invention, namely intended for the implementation of the invention, may be a cosmetic composition, and may therefore comprise a physiologically acceptable medium. The composition used according to the invention may be administered in particular topically or orally, preferably topically. Preferably, a composition according to the invention, when it is present within a composition, is formulated in a physiologically acceptable medium. When the composition is to be administered topically, such a medium is considered physiologically acceptable when it does not generate tingling, tightness or redness unacceptable to the user. By "physiologically acceptable medium" is meant a medium that is compatible with all keratin materials such as the skin, the scalp, the nails, the mucous membranes, the eyes and the hair, or any other cutaneous zone of the body. A physiologically acceptable medium is preferably a cosmetically or dermatologically acceptable medium, with no color or unpleasant appearance, and which is perfectly compatible with the route of administration considered. Advantageously, a composition suitable for the invention comprising a 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene compound of formula (I) according to the invention is intended for administration by topical route.

The invention also relates to a method for the cosmetic treatment of oxidative stress caused by exposure of the skin to UV radiation, including the scalp, characterized by the fact that it is applied to the skin, and / or for example on the scalp, a cosmetic composition comprising an effective amount of at least one 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene compound of formula (I) as defined in description, or a salt or solvate or optical isomer, stereoisomer, or diastereoisomer of said compound. Certain compounds of 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene of formula (I), the use of which is defined in the present description are known.

Certain other compounds of 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene of formula (I), the use of which is defined in the present description, are novel compounds which have been specially formulated for the purpose of carrying out the invention. Thus, the present invention also relates to certain compounds of 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene of formula (I) defined in the present description, which compounds, to the knowledge of the applicant, have not been described in the state of the art. Also, the present invention provides processes for the preparation of the 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene compounds of formula (I), the use of which is defined herein. description, including 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene compounds of formula (I) new. Compounds of 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene used according to the invention As previously stated in a general manner, the invention relates to the cosmetic use, in a composition containing a physiologically acceptable medium, of at least one compound of formula (I): OR 3 OR 4 (I) in which: R 1 signifies a hydrogen, a hydroxyl, a linear or branched, saturated or unsaturated C 1 -C 6 alkoxy or a benzyloxy R2 means: a hydroxyl, a linear or branched, saturated or unsaturated C1-C6 alkoxy, optionally substituted by a carboxyl, a linear or branched C1-C6 alkylcarbonyloxy, saturated or unsaturated, non-conjugated with the carbonyl, the alkylcarbonyloxy being optionally substituted by: (i) the group NR'R ", with R 'and R" which stand, independently of one another, a hydrogen, a benzyl, a linear or branched C1-C6 alkyl, saturated or unsaturated, linear or branched C1-C6 alkylcarbonyl saturated or unsaturated, linear or branched, saturated or unsaturated C1-C6 alkyloxycarbonyl, benzyloxycarbonyl; or (ii) the group OR ", with R" which means hydrogen, benzyl, linear or branched, saturated or unsaturated C1-C6 alkyl, linear or branched C1-C6 alkylcarbonyl, saturated or unsaturated, alkyloxycarbonyl linear or branched, saturated or unsaturated C1-C6 benzyloxycarbonyl; (iii) NHR-, with R "which means hydrogen, a linear or branched, saturated or unsaturated, C1-C6 alkylcarbonyl, non-conjugated with carbonyl, a linear or branched C1-C6 alkylsulfonyl, saturated or unsaturated, non-conjugated with the sulfonyl, - R3 and R4, which are identical, mean hydrogen, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear or branched C1-C6 alkyloxycarbonyl, saturated or unsaturated, it being understood that: - when R1 means a hydrogen, an alkoxy or a benzyloxy, then R2 R3 and R4 can not simultaneously include an alkyl group, it being understood that this condition does not apply when R2 is a group comprising a carboxyl, - when R1 and R3 and R4 which both mean hydrogen, then R2 is different from hydroxyl, methoxy, acetoxy or acetamino, - when R1 is hydrogen and R2 is hydroxy then R3 and R4 are different of a methyl group, and - when R1 signifies e is hydroxy and R3 and R4 both mean hydrogen, then R2 is other than hydroxy or methoxy, as are the isomers, salts and solvates of the compound of formula (I) to protect the skin oxidative stress caused by exposure to UV radiation. For the purposes of the invention, an alkyl group is a linear or branched saturated aliphatic group. C1-C6alkyl is an alkyl group having 1 to 6 carbon atoms, i.e. the alkyl group may comprise 1, 2, 3, 4, 5 or 6 carbon atoms. As examples of alkyl groups, mention may be made of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl and hexyl groups. Within the meaning of the invention, an alkoxy is a -O-alkyl group where the alkyl group is as defined above. C1-C6 alkoxy is a -O-alkyl group wherein the alkyl group comprises 1 to 6 carbon atoms, i.e. the alkyl group may comprise 1, 2, 3, 4, 5 or 6 carbon atoms. C1-C6 alkoxy includes methoxy, ethoxy, propoxy, butoxy, pentoxy and hexyloxy groups. Within the meaning of the invention, an alkylcarbonyloxy group is a group of formula (X1): ## STR2 ## in which "Alk" signifies an alkyl group as defined above. For the purposes of the invention, an alkylcarbonyl group is a group of formula (X2): ## STR5 ## in which "Alk" denotes an alkyl group as defined above. For the purposes of the invention, a benzyloxycarbonyl group is a group of formula (X3): o) (X3). Within the meaning of the invention, a sulfate group is a group of formula (X4): ## STR2 ## Within the meaning of the invention, a sulfate salt includes a sodium salt, a potassium salt, a lithium salt, a magnesium salt and a calcium salt. Within the meaning of the invention, an alkylsulfonyl group is a group of formula (X5): ## STR2 ## in which "Alk" signifies an alkyl group, as defined above. Within the meaning of the invention, an alkoxycarbonyl group is a group of formula (X6) 0 ALK-O * (X6), in which the group "Alk-O" means an alkoxy group as defined above. Preferably, the isomers according to the invention are stereoisomers, in particular enantiomers, diastereoisomers, as well as their mixtures, including racemic mixtures. Acceptable solvates of the compounds of formula (I) 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. According to a first variant of a compound of formula (I), or a salt or a solvate or an optical, stereoisomeric or diastereoisomeric isomer, according to the invention: R 1 represents a linear or branched C 1 -C 6 alkoxy, saturated or unsaturated, or benzyloxy; R2 is hydroxyl, linear or branched C1-C6 alkoxy, saturated or unsaturated, optionally substituted with carboxyl, linear or branched C1-C6 alkylcarbonyloxy, saturated or unsaturated, non-conjugated with the carbonyl, the alkylcarbonyloxy being optionally substituted with (i) the group NR'R ", with R 'and R" which signify, independently of each other, a hydrogen, a benzyl, a C 1 -C 4 alkyl -C6 linear or branched, saturated or unsaturated, linear or branched, saturated or unsaturated C1-C6 alkylcarbonyl, linear or branched C1-C6 alkyloxycarbonyl, saturated or unsaturated, benzyloxycarbonyl; or (ii) the group OR ", with R" which means hydrogen, benzyl, linear or branched, saturated or unsaturated C1-C6 alkyl, linear or branched C1-C6 alkylcarbonyl, saturated or unsaturated, linear or branched, saturated or unsaturated C1-C6 alkyloxycarbonyl, benzyloxycarbonyl; (iii) NHR-, with R "which means hydrogen, a linear or branched, saturated or unsaturated C 1 -C 6 alkylcarbonyl, non-conjugated with carbonyl, a linear or branched C 1 -C 6 alkylsulfonyl, saturated or unsaturated, non-conjugated with the sulfonyl, - R3 and R4, which are identical, mean hydrogen, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear or branched C1-C6 alkyloxycarbonyl, saturated or unsaturated, it being understood that: - when R1 is alkoxy or benzyloxy, then R2 and R3 can not simultaneously include an alkyl group.In some embodiments, this condition does not apply when R2 contains a carboxyl-substituted group, according to this first variant of the compounds of the formula (I), the compounds for which: R 1 is a linear or branched, saturated or unsaturated C 1 -C 6 alkoxy or a benzyloxy, preferably a saturated linear C 1 -C 4 alkoxy, and preferably, methoxy, - R2 is hydroxyl, - R3 and R4, which are the same, mean a linear or branched, saturated or unsaturated C1-C6 alkyl, preferably a saturated linear C1-C4 alkyl, and preferably most preferably a methyl ,. A particularly preferred compound of this first variant is the following compound A: (A) According to a second variant of a compound of formula (I), or a salt or a solvate or an optical isomer, stereoisomer, or diastereoisomer, according to Invention: R1 is hydrogen, R2 is: linear or branched C1-C6 alkoxy, saturated or unsaturated, optionally substituted with carboxyl, linear or branched C1-C6 alkylcarbonyloxy, saturated or unsaturated, non-conjugated with the carbonyl, the alkylcarbonyloxy being optionally substituted with: (i) the group NR'R ", with R 'and R" which signify, independently of one another, a hydrogen, a benzyl, a C1-alkyl -C6 linear or branched, saturated or unsaturated, a linear or branched, saturated or unsaturated C1-C6 alkylcarbonyl, a linear or branched C1-C6 alkyloxycarbonyl, saturated or unsaturated, a benzyloxycarbonyl; or (ii) the group OR ", with R- which means a hydrogen, a benzyl, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear or branched C1-C6 alkylcarbonyl, saturated or unsaturated, an alkyloxycarbonyl C1-C6 linear or branched, saturated or unsaturated, benzyloxycarbonyl; (iii) NHR-, with R "which means hydrogen, a linear or branched, saturated or unsaturated C1-C6 alkylcarbonyl, unconjugated with carbonyl, a C1-C6 linear or branched, saturated or unsaturated alkylsulfonyl, non-conjugated with the sulfonyl, - R3 and R4, which are identical, means hydrogen, linear or branched C1-C6 alkyl, saturated or unsaturated, linear C1-C6 alkyloxycarbonyl or branched, saturated or unsaturated, it being understood that: - when R3 and R4 both signify hydrogen, then R2 is different from an acetylamino group. According to this second variant of the compounds of formula (I), a first family of compounds of formula (I) are those for which: - R1 means a hydrogen, - R2 means NHR-, with R "which means a hydrogen, an alkylcarbonyl C2-C6 linear or branched, saturated or unsaturated, non-conjugated with carbonyl, a linear or branched, saturated or unsaturated C1-C6 alkylsulfonyl, non-conjugated with the sulfonyl, preferably R "meaning hydrogen, - R3 and R4 mean both a hydrogen. A particularly preferred compound of this second variant is the following compound B: HO NH 2 OH (B) According to this second variant of the compounds of formula (I), a second family of compounds of formula (I) are those for which: means hydrogen, - R2 means: linear or branched, saturated, carboxyl-substituted C1-C6 alkoxy, linear or branched C1-C6 alkylcarbonyloxy, saturated, alkylcarbonyloxy being substituted with: (i) NR group "R", with R 'and R "which mean, independently of one another, a hydrogen, a benzyl, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear C1-C6 alkylcarbonyl or branched, saturated or unsaturated, linear or branched, saturated or unsaturated C1-C6 alkyloxycarbonyl, benzyloxycarbonyl; or (ii) the group OR ", with R" which means hydrogen, benzyl, linear or branched, saturated or unsaturated C1-C6 alkyl, linear or branched C1-C6 alkylcarbonyl, saturated or unsaturated, alkyloxycarbonyl linear or branched C1-C6, saturated or unsaturated, benzyloxycarbonyl; (iii) the group NHR-, with R "which signifies hydrogen, a linear or branched, saturated or unsaturated C 1 -C 6 alkylcarbonyl, non-conjugated with the carbonyl, preferably saturated linear C 1 -C 4, more preferentially an acetyl, or else R "means a linear or branched, saturated or unsaturated C1-C6 alkylsulfonyl, non-conjugated with sulfonyl, preferably saturated linear C1-C4, more preferably a methylsulfonil, - R3 and R4, which are identical, mean an alkyl linear or branched C1-C6 saturated, preferably a linear or branched C1-C4 alkyl, saturated, more preferably a methyl. In certain embodiments of this second family of compounds of formula (I) belonging to this second variant, R 2 is linear, saturated C 1 -C 4 alkoxy substituted by a carboxyl.

In certain embodiments of this second family of compounds of formula (I) belonging to this second variant, R2 signifies the group -O-CH 2 -COOH. In certain embodiments of this second family of compounds of formula (I) belonging to this second variant, R2 signifies a saturated, linear or branched C1-C4 alkylcarbonyloxy substituted with NR'R "or OR" groups. In certain embodiments of this second family of compounds of formula (I) belonging to this second variant, R2 denotes a saturated linear or branched C1-C6 alkylcarbonyloxy substituted in the alpha position of the carbonyl by the NR'R "group. In these embodiments, R 'and R "both preferably signify hydrogen. In certain embodiments of this second family of compounds of formula (I) belonging to this second variant, R2 denotes a linear C 1 -C 4 alkylcarbonyloxy. or in branched, saturated, substituted in the alpha position of the carbonyl by the group NR'R '. In these embodiments, R' and R "both mean preferably a hydrogen. In some embodiments of this second family of compounds of Formula (I) belonging to this second variant, R2 signifies a saturated linear or branched C1-C6 alkylcarbonyloxy, the alkylcarbonyloxy being substituted by the group OR ", the group eg OR "being in the beta position of the carbonyl. In these embodiments, R "preferably denotes hydrogen In certain embodiments of this second family of compounds of formula (I) belonging to this second variant, R2 denotes a saturated linear or branched C1-C4 alkylcarbonyloxy, the alkylcarbonyloxy being substituted by the group OR ", the group OR" being in the beta position of the carbonyl In these embodiments, R "preferably means a hydrogen. In certain embodiments of this second family of compounds of formula (I) belonging to this second variant, R2 denotes NHR-, with R "which means a saturated linear C1-C4 alkylcarbonyl, and more preferentially an acetyl. embodiment of this second family of compounds of formula (I) belonging to this second variant, R2 means a saturated linear C1-C4 alkylsulfonyl, and more preferably a methylsulfonyl.

In certain preferred embodiments of this second family of compounds of formula (I) belonging to this second variant, R3 and R4 are identical and mean a linear or branched C1-C4 alkyl, saturated, and are more preferably a methyl. Particularly preferred compounds of formula (I) are the compounds of formulas C, D, E, F, G and H described below and their salts. ## STR2 ## The compounds of formula (I) are also preferred. The present invention also relates to a compound of formula (I): ## STR2 ## Ta): R2 OR3 OR4 (Ta) in which: R2 is: linear or branched, saturated or unsaturated, C1-C6 alkoxy substituted by carboxyl, linear or branched C1-C6 alkylcarbonyloxy, saturated or unsaturated, not conjugated with the carbonyl, the alkylcarbonyloxy being substituted with: (i) the group NR'R ", with R 'and R" which stand, independently of one another, a hydrogen, a benzyl, a C1-alkyl -C6 linear or branched, saturated or unsaturated, a linear or branched, saturated or unsaturated C1-C6 alkylcarbonyl, a linear or branched C1-C6 alkyloxycarbonyl, saturated or unsaturated, a benzyloxycarbonyl; or (ii) the group OR ", with R" which means hydrogen, benzyl, linear or branched, saturated or unsaturated C1-C6 alkyl, linear or branched C1-C6 alkylcarbonyl, saturated or unsaturated, alkyloxycarbonyl linear or branched, saturated or unsaturated C1-C6 benzyloxycarbonyl; - R3 and R4, which are identical, mean a hydrogen, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear or branched C1-C6 alkyloxycarbonyl, saturated or unsaturated, it being understood that: - when R2 signifies a corresponding alkylcarbonyloxy to a seryl residue (with the free amino group), then R3 and R4 are both different from a methyl, - when R2 signifies 0- (CH2) 2 -COOH or O- (CH2) 5 -COOH, then R3 and R4 are both different from hydrogen, - when R2 signifies one of the following groups (A), (B) or (C): (B), * -O CO2H * -C) VCO2H (A) , then R3 and R4 are both different from hydrogen or methyl. in which: - R5 is a hydroxyl, a linear or branched, saturated or unsaturated C1-C6 alkoxy, or a benzyloxy; - R6 is: a hydroxyl, a linear or branched, saturated or unsaturated, optionally substituted C1-C6 alkoxy; by carboxyl, a linear or branched, saturated or unsaturated C 1 -C 6 alkylcarbonyloxy, non-conjugated with the carbonyl, the alkylcarbonyloxy being optionally substituted with: (i) the group NR'R ", with R 'and R" which signify , independently of one another, hydrogen, benzyl, linear or branched, saturated or unsaturated C1-C6 alkyl, linear or branched C1-C6 alkylcarbonyl, saturated or unsaturated, C1-C6 alkyloxycarbonyl linear or branched, saturated or unsaturated, benzyloxycarbonyl; or (ii) the group OR ", with R" which means hydrogen, benzyl, linear or branched, saturated or unsaturated C1-C6 alkyl, linear or branched C1-C6 alkylcarbonyl, saturated or unsaturated, alkyloxycarbonyl linear or branched, saturated or unsaturated C1-C6 benzyloxycarbonyl; (iii) NHR-, with R "which means hydrogen, a linear or branched, saturated or unsaturated C 1 -C 6 alkylcarbonyl, non-conjugated with carbonyl, a linear or branched C 1 -C 6 alkylsulfonyl, saturated or unsaturated, non-conjugated with the sulfonyl, - R7 and R8, which are identical, mean a hydrogen, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear or branched, saturated or unsaturated C1-C6 alkyloxycarbonyl, it being understood that: the present invention also relates to a compound of formula (Ib): R6 OR7 R5 OR8 - when R5 is alkoxy or benzyloxy, then R6, R and / R8 can not simultaneously include an alkyl group (does not apply when R6 contains substitution with a carboxyl), - when R5 is hydroxy or methoxy and R7 and R8 are both hydrogen or methyl, then R6 is different from hydroxy and methoxy, - when R5 and R6 mean both hydroxy, then R7 and R8 are all the two different ones of n-propyl, - when R5 is methoxy and R6 is acetoxy, then R7 and R8 are both different from methyl, - when R5 is ethoxy and R6 is hydroxy, then R7 and R8 are both different from hydrogen or methyl, - when R5 and R6 both mean linear hexyloxy, then R7 and R8 are both different from hydrogen.

The compounds of formula (I) may be obtained by those skilled in the art, in particular by synthesis according to the usual methods known to those skilled in the art. The compounds of formula (I) can in particular be obtained by the methods specified in the present description. The compounds of formula (I), alone or as a mixture, and the composition comprising them may be used for topical application to the skin, including on the scalp. The amount of compounds of formula (I) that can be used in the context of the invention obviously depends on the desired effect and must be an amount effective to reduce or even inhibit the oxidative stress caused by exposure to UV radiation.

By way of example, the amount of compound of formula (I) may vary, for example, from 0.001% to 30% by weight, preferably from 0.01% to 10% by weight, in particular from 0.5% to 5% by weight. weight, relative to the total weight of the composition. The composition according to the invention is especially intended for topical application; it also comprises a physiologically acceptable medium, that is to say, compatible with the skin including the scalp, mucous membranes, nails, hair, eyelashes, eyebrows and / or eyes. The composition may then comprise all the constituents usually employed in the intended application.

There may be mentioned water, solvents, oils of mineral, animal and / or vegetable origin, waxes, pigments, fillers, surfactants, cosmetic actives and even polymers.

Composition, in particular a cosmetic composition The present invention also relates to a composition, especially a cosmetic composition, comprising, in a physiologically acceptable medium, at least one compound chosen from the compound of formula (I), and the compounds of formula (Ta) and (Ib) as defined herein. above and / or isomers and / or solvates of said compounds.

By "physiologically acceptable medium" is meant an environment compatible with keratin materials of human beings such as skin, mucous membranes, nails, scalp and / or hair. Thus, the physiologically acceptable medium is in particular a cosmetically or dermatologically acceptable medium, that is to say without odor, color or unpleasant appearance, and which does not generate tingling, tightness or redness unacceptable to the user. A composition according to the invention is particularly suitable for topical application to a keratinous material and in particular the skin and the scalp. Thus, it can be used as a skin care product, for example as a protective cream, treatment or treatment for the face, for the hands or for the body, as body protection or skincare milk, scalp or mucous membranes, or more particularly as a daily photoprotection product, sun protection or after-sun protection. The compositions according to the invention may also constitute products for the make-up of the skin and / or the hair, for example by incorporating pigments therein to constitute, in particular, foundations, makeup bases. The invention also relates to a cosmetic composition comprising, in a physiologically acceptable medium, at least one compound chosen from the compound of formula (I), (Ta) or (Ib) as defined in the present description.

In certain embodiments of this cosmetic composition, the compound of formula (I), (Ta) or (Ib) is present, alone or as a mixture, in an amount of between 0.001% and 30% by weight, preferably between 0 , 01% and 10% by weight, especially between 0.5% and 5% by weight, relative to the total weight of the composition.

In some embodiments of this cosmetic composition, the physiologically acceptable medium comprises at least one cosmetic adjuvant selected from water; organic solvents, especially C2-C6 alcohols and C2-C10 carboxylic acid esters; hydrocarbon oils, silicone oils, fluorinated oils, waxes, pigments, fillers, dyes, surfactants, emulsifiers, cosmetic or dermatological active agents, UV filters, film-forming polymers, hydrophilic or lipophilic gelling agents, thickeners, preservatives, perfumes, bactericides, odor absorbers and antioxidants. In some embodiments of this cosmetic composition, it is in the form of a protective composition against oxidative stress caused by exposure of the skin and / or its integuments to UV radiation. Fatty phase Preferably, a composition according to the invention may comprise at least one fatty phase. For the purposes of the invention, the fatty phase includes any liquid fatty substances, generally oils, or solids, such as waxes or pasty compounds present in said composition. This fatty phase contains at least one non-volatile oil and in particular at least 40% by weight of non-volatile oil (s) as described below. The term "oil" means any fatty substance in liquid form at ambient temperature (25 ° C.) and at atmospheric pressure. The oil or oils may be present in a proportion of 0.1 to 50% by weight, in particular at least 5 to 40% by weight, relative to the total weight of the cosmetic composition according to the invention. The volatile or non-volatile oils may be hydrocarbon oils, in particular of animal or vegetable origin, synthetic oils, silicone oils, fluorinated oils, or mixtures thereof. For the purposes of the present invention, the term "silicone oil" means an oil comprising at least one silicon atom, and in particular at least one Si-O group.

The term "hydrocarbon-based oil" means an oil containing mainly hydrogen and carbon atoms and optionally oxygen, nitrogen, sulfur and / or phosphorus atoms.

Aqueous Phase The composition according to the invention may comprise an aqueous phase. For the purposes of the invention, the aqueous phase includes water and / or at least one water-soluble solvent. The water may be floral water such as cornflower water and / or mineral water such as VITTEL water, LUCAS water or LA ROCHE POSAY water and / or thermal water. By "water-soluble solvent" is meant in the present invention a liquid compound at room temperature and miscible with water (miscibility in water greater than 50% by weight at 25 ° C and atmospheric pressure). According to a particularly preferred embodiment, the aqueous phase of a composition according to the invention comprises at least one lower C2-C8 monoalcohol. Lower monoalcohols which are more particularly suitable for the invention contain from 2 to 8 carbon atoms, in particular from 2 to 6 carbon atoms, and in particular from 2 to 4 carbon atoms, such as ethanol and isopropanol, propanol, butanol. Ethanol and isopropanol, and preferably ethanol, are also particularly suitable for the invention. The emulsion according to the invention may comprise one or more C 2 to C 8 lower monoalcohol in a content of at least 1%, in particular of at least 2%, especially in the proportion of 2 to 10% by weight, relative to the total weight of the composition. In addition to the lower monoalcohol (s) defined previously, this aqueous phase may contain other alcohol (s), in particular polyethylene glycols having from 6 to 80 ethylene oxide units; polyols such as propylene glycol, isoprene glycol, butylene glycol, glycerine, sorbitol, glycol, dipropylene glycol, diethylene glycol, glycol ethers such as alkyl (C1-C4) monoalkyl ethers, or tripropylene glycol, mono-, di- or tri-ethylene glycol, and mixtures thereof. The aqueous phase may also comprise any water-soluble or water-dispersible compound compatible with an aqueous phase such as gelling agents, film-forming polymers, thickeners, surfactants and mixtures thereof.

Preferably, the composition according to the invention is a photoprotective composition used on a daily basis. According to another embodiment, the composition according to the invention is a so-called after-sun composition, which can be used on a daily basis.

The invention also relates to a method of non-therapeutic cosmetic treatment of the skin and / or its integuments, comprising the application on the skin, in particular on the scalp, of the skin. a cosmetic composition as defined in the present description. In some embodiments of the cosmetic treatment method, the composition is applied to mature and / or wrinkled skin. Another subject of the invention is a method of treatment, in particular a cosmetic treatment, of a keratinous material, characterized in that a composition as defined above is applied to the keratin material. For the purposes of the present invention, the term "keratin materials" is intended to denote the skin, the scalp, the mucous membranes, such as the lips, the nails and the keratinous fibers, like the eyelashes, the eyebrows and the hair. . Are particularly considered according to the invention, the parts of the keratin materials most likely to be exposed to sunlight, namely the skin and the lips, more particularly the skin of the face, scalp, neck, hands or legs, and more particularly the skin of the face. Particular embodiments of the methods for synthesizing the compounds of formula (I) Also specified are processes for the preparation of the compounds of formula (I) as defined in the present description. It is specified that the synthetic processes described below are applicable to the preparation of the compounds of formula (I), which includes the preparation of the different variants of the compounds of formula (I) defined in the present description, including the compounds of formula (Ta) and the compounds of formula (Ib). Accordingly, in the synthetic methods described below, (i) the group R1 corresponds to the group R5, (ii) the group R2 corresponds to the group R6, (iii) the group R3 corresponds to the group R7 and (iv) the R4 group corresponds to the group R8 subject to the specific meanings of the groups R5, R6, R7 and R8 for the compounds of formula (Ib). In general, the compounds of formula (I) belonging to the first variant of these compounds, illustrated in particular by compound A, may for example be prepared by the methods described in the article by Roberti et al., (2003, J Med Chem, Vol 46 (16): 3546-3554). In general, the compounds of formula (I) belonging to the first variant of these compounds, especially illustrated by compound B, may, for example, be prepared by the methods described in PCT Application No. WO 2010/046926.

In general, the compounds of formula (I) belonging to the first variant of these compounds, illustrated in particular by compound C, may for example be prepared by the processes described in PCT Application No. WO 2010/046926. The compounds of formula (I) belonging to the second variant of these compounds, especially illustrated by compound D, may for example be prepared by the processes described in PCT Application No. WO 2010/046926. The compounds of formula (I) belonging to the third variant of these compounds, illustrated in particular by compound E, may for example be prepared by the processes described in PCT Application No. WO 2010/046926. The compounds of formula (I) belonging to the fourth variant of these compounds, illustrated in particular by compound F, may, for example, be prepared by the methods described in PCT Application No. WO 2010/046926. The compounds of formula (I) belonging to the fourth variant of these compounds illustrated especially by compound G may for example be prepared by the methods described in PCT application No. WO 2010/046926. The compounds of formula (I) belonging to the fifth variant of these compounds, illustrated in particular by compound H, may, for example, be prepared by the processes described in PCT Application No. WO 2010/046926. The compounds of formula (I) can be obtained in particular by a Wittig-type olefination and its variants, according to the scheme shown in FIG. 1. The possible hydroxyl, amine and acid groups, reagents must be protected, if necessary, beforehand. Adequate protective group, as reviewed by Peter GM Wuts and Theodora W. Greene, in Greene's Protective Groups in Organic Synthesis, Fourth Edition, Wiley, 2006.

Reaction of Wittig or Wittig-Horner The phosphonate derivative can be obtained from the corresponding benzyl halide via conventional procedures. For example, a mixture of benzyl halide (1 eq.) And trimethyl or triethyl phosphite (2 eq.) In a high boiling point apolar solvent such as toluene is heated at 110 ° C. for 4 hours. 16 h. The product is then purified either by distillation or by conventional techniques such as precipitation / recrystallization or silica column chromatography. The phosphonium derivative can be obtained in the same way with triphenylphosphine. Under anhydrous conditions and under an inert atmosphere, a solution of the phosphonate or phosphonium derivative (1-1.3 eq.) In an aprotic polar solvent such as THF is treated at 0 ° C (-78 ° C for phosphonium) with a strong base. (1.1-2 eq) such as sodium hydride (NaH), lithium diisopropylamide (LDA), n-butyl lithium (nBuLi), followed by the dropwise addition of a solution of aldehyde (1 eq.) in the same solvent. Stirring is continued at room temperature overnight, until the aldehyde disappears and then cooled to 0 ° C. Water is added dropwise with stirring, followed by dilute aqueous hydrochloric acid solution. The mixture is then extracted with an organic solvent such as ether, CH 2 Cl 2 or EtOAc. The organic phases are combined, dried and concentrated under reduced pressure. The residue can be purified by silica column chromatography.

Steps for introducing specific substituents The groups that are incompatible with the key formation reactions of the target compounds will have to be introduced at a later stage according to the standard procedures. Similarly, if the reagents are not commercial, the substituents will have to be introduced on the corresponding phenolic derivatives, before or after the coupling step according to the chemical compatibility. Alkylationibenzylation of phenols OH base weak alkylating agent RX Scheme 1 The phenolic derivative to be substituted (1 eq./phenol) in an aprotic polar solvent such as DMF or DMSO is deprotonated by addition of a weak base (1-2 eq. ) such as OR potassium carbonate or cesium carbonate. The reaction mixture is stirred at 0-80 ° C and the alkylating agent RX (1-2 eq) is added dropwise. For example, the alkylating agent is an alkyl halide and preferably an alkyl iodide, or bromide or benzyl iodide. Stirring is continued for 1-96 h. The reaction mixture is diluted by adding a saturated aqueous solution of NH 4 Cl and extracted using an organic solvent such as ethyl acetate. The organic phases are combined, dried and concentrated under reduced pressure. The residue can be purified by silica column chromatography. Acylation of Phenols or Amines or a Substituted Phenol or Amine (1 eq.) And an Organic Base such as Triethylamine, Diisopropylethylamine or Pyridine (1.2) 2 eq.), In an aprotic polar solvent such as dichloromethane, acetone, acetonitrile or THF at 0 ° C., is treated dropwise with a solution of the acid chloride or with corresponding anhydride (1.1-1.5 eq.) in the same solvent. The reaction mixture is stirred at room temperature for 2-18 h and then diluted with water. After decantation and phase separation, the organic phase is washed with a saturated solution of NaCl, dried and concentrated under reduced pressure. The residue is purified by chromatography on a silica column. When it comes to the esterification of phenol with an amino acid (the amine group of which is protected by an adequate protective group), a coupling reaction is favored: FIG. 3 OR4 HO x, yNHPG X, NHPG agent R2 coupling RI 21.

To a solution of phenol (1 eq.) In an aprotic polar solvent such as dichloromethane, a coupling agent such as PyBop, HOBt / DCC or HOBt / EDCI (1 eq.), And DMAP (0.1 eq. ) at 0 ° C. After stirring for 30 minutes, the amino acid (1 eq.) Diluted in the same solvent is slowly added at 0 ° C. The reaction mixture is stirred for 4-18 h while returning to t.a. The product is then obtained after the washing, extraction and purification steps. Carbonation of phenols OH OR RO CI RO 0 OR Figure 4 Similar procedure as for acylation using chloroformate or alkyl dicarbonate (1.1-2 eq). Sulfonylation of amines NH2 base CkR H \\ N'R 00 \\ 00 Scheme 5 Similar procedure as for acylation using a sulfonyl chloride (1.1 eq.). Sulfation of phenols The sulphate group is introduced in the last step from the phenol precursor: 20 OH CISO 3 H, Et 3 N 7 --- OSO 3 H R 1 R 1 OR 4 OR 4 Scheme 6 To a solution of phenol (1 eq) in an aprotic polar solvent such as dichloromethane is added an organic base such as triethylamine (3 eq.) Chlorosulphonic acid (1.1 eq.) Is added to the solution at 0 ° C, and stirring is continued at t. at. during 2-18 h. The solvent is evaporated, and the residue is purified by chromatography on a silica column.

Precursors of the aniline groups The amine function can be obtained after reduction of a nitro precursor (commercial when R = H), via the usual procedures using zinc in a strong acid medium, SnCl 2 or else by catalytic hydrogenation.

Throughout the description, including the claims, the phrase "having one" should be understood as being synonymous with "having at least one", unless the opposite is specified. Expressions "between ... and ..." and "ranging from ..." must be understood as inclusive terms, unless otherwise specified.

The present invention is further illustrated, but not limited to, by the following examples. EXAMPLES Example 1 Synthesis of compounds A, B, C, D, E, F, G and H Compound A, for example synthesized according to the article by Roberti et al., (2003, J Med Chem, Vol 46 (16) : 3546-3554). Compound B synthesized for example according to: WO 2010046926, 2010, Preparation of novel stilbene analogs Compound C Synthesized for example according to: WO 2010046926, 2010, Preparation of novel stilbene analogs Compound D Synthesized for example according to: WO 2010046926, 2010, Preparation of novel stilbene analogs Compound E Synthesized for example according to: WO 2010046926, 2010, Preparation of novel stilbene analogs Compound F Synthesized for example according to: WO 2010046926, 2010, Preparation of novel stilbene analogs Compound G Synthesized for example according to: WO 2010046926, 2010, Preparation of novel stilbene analogs Compound H synthesized for example according to: WO 2010046926, 2010, Preparation of novel stilbene analogs Example 2: Activity of the compounds of formula (I) A. Materials and Methods Principle Evaluation of the reduction of the production of ROS (reactive species of oxygen) in HaCaT keratinocytes, detected by the Dihydrorhodamine 123 (DHR123) probe, induced by a UVA exposure after 24 hours of incubation in the presence of the samples. Procedure Keratinocytes from the HaCaT cell line in a monolayer are placed in the presence of a solution of the compounds at different concentrations (0.4-200 μM) in the medium. After 24 h of incubation, the cells are exposed to UVA and then incubated with the DHR123 probe for 1 h. The fluorescence of the probe is then measured. A viability test is performed in parallel to rule out the cytotoxic compounds. The positive control used is vitamin C. 500 jaM of vitamin C correspond to 100% of photoprotection.

The dose-effect curves make it possible to calculate the effective dose EC50 = product concentration allowing 50% protection. B. Results The results are shown in Table 1 below. Table 1 EC50 compound A 35 uIVI B 69 uIVI C 45 uIVI D 13.5 uIVI E 40 uIVI F 2.2 uIVI G 15 uIVI H 26 uIVI Thus the compounds of formula (I) are capable on a cell test at micromolar doses, to prevent formation of reactive species induced by UVA exposure. In a cosmetic formulation, these compounds are therefore effective for delaying / lessening the deleterious effects of oxidative stress in the skin due to UV exposure, the signs of which can be expressed in the long term by, a loosening of the cutaneous tissues and a loss of tone (firmness) of the skin, the appearance of wrinkles and furrows, a rough and yellowish appearance of the skin, a heterogeneity of the complexion, or the appearance of telangiectasia (blood vessels). EXAMPLE 5 Composition Example According to the Invention The percentages of compounds indicated in Table 2 are percentages by weight relative to the total weight of the composition comprising them.

Table 2 Ingredient Quantity (% by weight) Compound A 1% Glycerin 12% POLYACRYLAMIDE 40% MA (SEPIGEL 305 from SEPPIC) 1% Preservatives qs Perfume qs Water qs 100% The above composition, applied topically to the skin allows fight against the signs of aging oxidative stress in the skin due to UV exposure, such as wrinkles and fine lines, or withered skin, soft and / or thinned. The same type of results is obtained by replacing the compound A with one of the compounds B, C, D, E, F, G or H.10.

Claims (3)

REVENDICATIONS1. Cosmetic use, in a composition containing a physiologically acceptable medium, of at least one compound of formula (I): R 2 R 1 OR 4 in which: R 1 represents a hydrogen, a hydroxyl or a linear or branched C 1 -C 6 alkoxy, saturated or unsaturated, or benzyloxy, - R2 means: hydroxyl, linear or branched, saturated or unsaturated C1-C6 alkoxy optionally substituted with carboxyl, linear or branched C1-C6 linear or branched alkylcarbonyloxy, saturated or unsaturated, non-conjugated with the carbonyl, the alkylcarbonyloxy being optionally substituted by: (i) the group NR'R ", with R 'and R" which signify, independently of one another, a hydrogen, a benzyl, a C1 alkyl -C6 linear or branched, saturated or unsaturated, a linear or branched, saturated or unsaturated C1-C6 alkylcarbonyl, a linear or branched C1-C6 alkyloxycarbonyl, saturated or unsaturated, a benzyloxycarbonyl; or (ii) the group OR ', with R "which means a hydrogen, a benzyl, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear or branched C1-C6 alkylcarbonyl, saturated or unsaturated, an alkyloxycarbonyl saturated or unsaturated, linear or branched C1-C6, benzyloxycarbonyl; NfiR '", with R"' which means hydrogen, linear or branched C1-C6 alkylcarbonyl, saturated or unsaturated, non-conjugated with carbonyl, alkylsulfonyl C1-C6 linear or branched, saturated, unsaturated, non-conjugated with the sulfonyl, - R3 and R4, identical, means hydrogen, linear or branched, saturated or unsaturated C1-C6 alkyl, linear C1-C6 allcyloxycarbonyl or when branched, saturated or unsaturated, with the proviso that: - when R 1 is hydrogen, alkoxy or benzyloxy, then R2 and R3 can not simultaneously include an alkyl group, which condition does not apply when R2 is a group comprising a carboxyl, - when R1 and R3 both mean hydrogen, then R2 is different from hydroxyl, methoxy, acetoxy or acetamino, - when R1 is hydrogen and R2 is hydroxy then R3 and R4 are different of an ethyl group, and - when R 1 is hydroxy and R 3 and R 4 both mean hydrogen, then R 2 is other than hydroxy or methoxy, as well as optical isomers, stereoisomers, and / or diastereoisomers, salts and solvates of the compound of formula (I) for protecting the skin from oxidative stress caused by UV radiation exposure. 2. Use according to claim 1, the compound of formula (1) being characterized - R1 represents a linear or branched, saturated or unsaturated C1-C6 alkoxy, or in that: benzyloxy, R2 means: a hydroxyl, a linear or branched, saturated or unsaturated C1-C6 alkoxy, optionally substituted by carboxyl, a linear or branched C1-C6 alkylcarbonyloxy, saturated or unsaturated, non-conjugated with the carbonyl, the alkylcarbonyloxy being optionally substituted by (i) the bleR "group, with R 'and R" which mean, independently of one another, a hydrogen, a benzyl, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear C1-C6 alkylcarbonyl or branched, saturated or unsaturated, linear or branched, saturated or unsaturated C1-C6 alkyloxycarbonyl, benzyloxycarbonyl; or (ii) the group OR ", with R" which means a hydrogen, a benzyl, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear or branched C1-C6 alkylcarbonyl, saturated or unsaturated, an alkyloxycarbonyl linear or branched, saturated or unsaturated C1-C6 benzyloxycarbonyl; (iii) ', with R' which signifies hydrogen, a linear or branched, saturated or unsaturated C 1 -C 6 alkylcarbonyl, non-conjugated with E-carbonyl, a linear or branched, saturated or unsaturated, non-conjugated C1-C6 alkylsulfonyl; with the sulfonyl, - R3 and R4, which are identical, mean a hydrogen, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear or branched, saturated or unsaturated C1-C6 alkyloxycarbonyl, it being understood that: - when RI means alkoxy or benzyloxy, then R2, R3 and R4 can not simultaneously include an alkyl group, this condition not being applicable when RZ is a carboxyl-substituted group. 3. Use according to claim 2. the compound of formula (I) being characterized in that: - Ri means a linear or branched, saturated or unsaturated C1-C6 alkoxy or benzyloxy. preferably a saturated linear C1-C4 alkoxy, and most preferably a methoxy, - R2 means a hydroxyl, - R3 and R4, identical, mean a linear or branched, saturated or unsaturated C1-C6 alkyl of preferably a saturated linear C1-C4 alkyl, and most preferably a methyl, 4. Use according to claim 1, the compound of formula (I) being characterized in that: - R1 means a hydrogen, - R2 means : a linear or branched, saturated or unsaturated C1-C6 alkoxy optionally substituted by a carboxyl, a linear or branched C1-C6 alkkycarbonyloxy, saturated or unsaturated, non-conjugated with the carbonyl, the alkylcarbonyloxy being optionally substituted with: i) the group NR'R ", with R 'and R" which mean. independently of one another, a hydrogen. a benzyl, a linear or branched C1-C6 alkyl, saturated or unsaturated, a linear or branched, saturated or unsaturated C1-C6 alkylcarbonyl, a linear or branched C1-C6 alkyloxycarbonyl, saturated or unsaturated, a benzyloxycarbonyl; or (ii) the group OR ", with R" which means a hydrogen, a benzyl, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear or branched, saturated or unsaturated C 1 -C 6 alkylcarbonyl, an alkyloxycarbonyl linear or branched, saturated or unsaturated C1-C6 benzyloxycarbonyl; (iii) NIIR '", with R" meaning hydrogen, a linear or branched, saturated or unsaturated C1-C6 alkylcarbonyl, non-conjugated with carbonyl, a linear or branched C1-C6 alkylsulfonyl, saturated or unsaturated, not conjugated with 8ulfonyi. R 3 and R 4, which are identical, denote hydrogen, a linear or branched, saturated or unsaturated C 1 -C 6 alkyl radical, a linear or branched C 1 -C 6 alkyloxycarbonyl, saturated or unsaturated, it being understood that when R 3 and R 4 signify all both a hydrogen, then R2 is different from an acetylamino group. 5. Use according to claim 4, the compound of formula CO being characterized in that: R1 means a hydrogen, R2 means: MIR "1, with R" "which means a hydrogen, a linear or branched C2-C6 alkylcarbonyl , saturated or unsaturated, non-conjugated with carbonyl, a linear, branched, saturated or unsaturated C 1 -C 6 alkylsulfonyl, non-conjugated with sulfonyl, R "being preferably hydrogen, - R 3 and R 4 both mean hydrogen. 6. Use according to claim 4, the compound of formula (I) being characterized in that: - R1 means a hydrogen, - R2 means: a linear or branched, saturated, substituted by a carboxyl, C1-C6 alkylcarbonyloxy linear or branched C1-C6, saturated, the alkylcarbonyloxy being substituted by: (i) the group NR'R ", with R 'and R" which signify, independently of one another, a hydrogen, a benzyl , a linear or branched C1-C6 alkyl, saturated or unsaturated, alkyl linear or branched, saturated or unsaturated C1-C6 arbonyl, linear or branched, saturated or unsaturated C1-C6 alkyloxycarbanyl, benzyloxycarbonyl; with R 'and R "which preferably signify hydrogen, or (ii) the group OR", with R "which signifies a hydrogen, a benzyl, a linear or branched C1-C6 alkyl, saturated or unsaturated, an alkylcarbonyl C1-C6 linear or branched, saturated or unsaturated, a linear or branched, saturated or unsaturated C1-C6 alkyloxycarbonyl, a benzyloxycarbonyl R '"which preferably means a hydrogen, (iii) the group NBR'", with R "which is hydrogen, a linear or branched, saturated or unsaturated C 1 -C 6 alkylcarbonyl, non-conjugated with the carbonyl, preferably saturated linear C 1 -C 4, more preferably acetyl, or R 1 is linear C 1 -C 6 alkylsultenyl; branched, saturated or unsaturated, non-conjugated with sulfonyl, preferably saturated linear Cl-C4, more preferably methylsulfonil, - R3 and R4, identical, means a linear or branched C1-C6 alkyl, saturated, preferably an alkyl in C1-C4 linear o branched, saturated, more preferably a methyl. 7. Compound of formula (Ia): ORs OR4 (la) in which: R2 is: a linear or branched, saturated or unsaturated C1-C6 alkoxy substituted by a carboxyl, a linear or branched C1-C6 alkylcarbonyloxy, saturated or unsaturated, non-conjugated with the carbonyl, the alkylcarbonyloxy being substituted by: (i) the group NR'R ", with R 'and R" which signify, independently of one another, a hydrogen, a benzyl , a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear or branched, saturated or unsaturated C1-C6 alkylcarbonyl, a linear or branched, saturated or unsaturated C1-C6 alkyloxycarbonyl, a benzyloxycarbonyl or (ii) the OR "group, with R" which means hydrogen, benzyl, linear or branched, saturated or unsaturated C1-C6 alkyl, linear or branched, saturated or unsaturated C1-C6 alkylcarbonyl, linear C1-C6 alkyloxycarbonyl or branched, saturated, or unsaturated, a benzyloxycarbonyl, - R3 and R4 are identical and mean, u hydrogen, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear or branched, saturated or unsaturated C1-C6 alkyloxycarbonyl, it being understood that: when R2 signifies an alkylcarbonyloxy corresponding to a seryl residue (with the group free amino), then R3 and R4 are both different from methyl, - when R2 is O- (C112) 2-000H or O- (CH2) 5-00014, then R3 and R4 are both different from hydrogen, - when RZ is one of the following groups (A), (B) or (C) O CO2H then R3 and R4 are both different from hydrogen or methyl, as well as the isomers , the salts and the solvates of the compound of formula (Ia). 8. Compound of formula (Fo): ## STR5 ## wherein: R5 denotes a hydroxyl, a linear C1-C6 alkoxy; or branched, saturated or unsaturated, or a beazyloxy, - R6 means: a hydroxyl, a linear or branched, saturated or unsaturated C1-C6 alkoxy, optionally substituted by a carboxyl a linear or branched, saturated or unsaturated C1-C6 alkylcarbonyloxy, non-conjugated with the carbonyl, the alkylcarbonyloxy being optionally substituted by: (i) the group NR'R ", with R 'and R" which independently signify one of the other, hydrogen, benzyl, linear or branched, saturated or unsaturated C1-C6 alkyl, linear or branched, saturated or unsaturated C1-C6 alkylcarbonyl, linear or branched C1-C6 alkyloxycarbonyl saturated or unsaturated benzyloxycarbonyl; or (ii) the group OR ", with R" which means a hydrogen, a benzyl, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear or branched C1-C6 alkylcarbonyl, saturated or unsaturated, an alkyloxycarbonyl linear or branched, saturated or unsaturated C 1 -C 5 benzyloxycarbonyl; (iii) Nlem, with R "which signifies hydrogen, a linear or branched, saturated or unsaturated C1-C4 alkylcarbonyl, non-conjugated with carbonyl, a linear or branched, saturated or unsaturated C1-C6 alkylsulfonyl, non-conjugated with the identical sulfonyl, R7 and R8, signify a hydrogen, a linear or branched, saturated or unsaturated C1-C6 alkyl, a linear or branched C1-C6 alkyloxycarbonyl, saturated or unsaturated, it being understood that: - when R5 means alkoxy or benzyloxy, then R6, R7 and R8 can not simultaneously include an alkyl group (does not apply when R6 contains a carboxyl substitution), when R5 is hydroxy or methoxy and R7 and R8 are all both hydrogen or methyl, then R6 is different from hydroxy and methoxy, - when R5 and R6 both mean hydroxy, then R7 and R8 are both different from n-propyl; when R5 means a methoxy and Re means an aoe toxy, then R7 and R8 are both different from methyl, - when R5 is ethoxy and Rg is hydroxy then R7 and R8 are both different from hydrogen or methyl, - when R5 and R6 both mean a linear hexyloxy, so R7 and R8 are both different from hydrogen. as well as the isomers, the salts and the solvates of the compound of formula (I) 9. Cosmetic composition comprising, in a physiologically acceptable medium, at least one compound chosen from the compound of formula (1) as defined in one of the Claims 1 to 6, the compound of formula (la) as defined in claim 7 and the compound of formula (lb) as defined in claim 8. The cosmetic composition of claim 9, wherein the compound of formula (I), (Ia) or (Ib) is present, alone or as a mixture, in an amount of between 0.001% and 30% by weight, preferably between 0.01% and 10% by weight, in particular between 0.5 % and 5% by weight, relative to the total weight of the composition. 11. Composition according to one of claims 9 and 10, wherein the physiologically acceptable medium comprises at least one cosmetic adjuvant selected from water; organic solvents, especially C2-C6 alcohols and C2-C10 carboxylic acid esters; hydrocarbon oils, silicone oils, fluorinated oils, waxes, pigments, fillers, dyes, surfactants, emulsifiers, cosmetic or dermatological active agents, UV filters, filamentary polymers, hydrophilic or lipophilic gelling agents, thickeners, preservatives, perfumes, bactericides, odor absorbers and antioxidants. 12. Composition according to one of claims 9 to 11, being in the form of a protective composition against oxidative stress caused by exposure of the skin or scalp to UV radiation. 13. Cosmetic use, in a composition containing a physiologically acceptable medium, of at least one 1-phenyl (3,4-diisubstituted 2-phenyl (3,5-disubstituted) ethylene compound as defined in one of claims 1 to 6 or a salt or solvate of said compound to protect the skin, including the scalp, from oxidative stress caused by UV radiation exposure .14 A method of non-therapeutic cosmetic treatment of the skin, comprising applying to the skin skin of a cosmetic composition as defined in any one of claims 9 to 12. 15. A method according to the preceding claim wherein the composition is applied to a mature skin and / or wrinkled 16. Non-therapeutic use of a cosmetic composition as defined in one of claims 9 to 12, for protecting the skin from oxidative stress caused by exposure of the skin or scalp to UV radiation. for protecting the skin from oxidative stress caused by exposure of the skin or scalp to UV radiation, comprising at least one step of topical application to the skin or scalp of a composition as defined in one of Claims 10 to 12. 18. Cosmetic treatment method for oxidative stress "caused by exposure of the skin to UV radiation, including the scalp, characterized by the fact that it is applied to the skin, for example on the scalp, a cosmetic composition comprising an effective amount of at least one 1-phenyl (3,4-disubstituted), 2-phenyl (3,5-disubstituted) ethylene compound of formula W as defined in one of Claims 1 to 6.