FR3073145A1 - PROCESS FOR TREATING KERATINIC MATERIALS FROM DERIVATIVES OF ACIDIC ESTERS OR AMIDES C-GLYCOSIDES AND THE COSMETIC COMPOSITION CONTAINING THEM - Google Patents

Abstract

The present invention relates to a process for the cosmetic treatment of keratinous substances, in particular the skin, comprising the application on said keratin materials such as the skin, of a composition comprising a compound (I) with R as defined in the description and S * a mono or polysaccharide. The invention relates in particular to the non-therapeutic cosmetic use of at least one compound of formula (I) as defined below as a whitening, lightening and / or depigmenting agent for keratinous substances, in particular the skin.

Description

PROCESS FOR THE TREATMENT OF KERATINIC MATERIALS FROM DERIVATIVES OF ACIDIC C-GLYCOSIDES, ESTERS OR AMIDES, AND THE COSMETIC COMPOSITION CONTAINING THEM

The present invention relates to the field of cosmetic products, more particularly intended for the care of keratin materials, in particular for the care of the skin of the face and / or the body.

The invention relates to C-glycoside compounds containing an acid, ester or amide group, a cosmetic composition comprising them, a method of preparation, the use of said C-glycosides for the treatment of keratinous substances and in particular the skin; and a method for treating keratin materials using said C-glycosides.

More particularly, the present invention aims to propose the use of a new active agent for effectively depigmenting and / or lightening, or even bleaching, keratin materials, in particular the skin of the face and / or the body and / or improving the complexion, in particular its homogeneity and its luster.

The color of human keratin materials, especially human skin, is mainly determined by the nature and concentration of a pigment, melanin.

The mechanism of melanogenesis, that is to say the mechanism of formation of melanin, is particularly complex and schematically involves the following main stages:

Tyrosine -> Dopa -> Dopaquinone -> Dopachrome -> Melanin

More specifically, tyrosinase is the essential enzyme that regulates the first stages of the synthesis of pheomelanin and eumelanin which are the two types of melanin.

The pigmentation of the skin of the face and / or the body, and more particularly the pigmentation of the skin, is a function of various factors such as environmental factors linked to the seasons of the year, and the origin of the individual.

In addition, at different periods of their life, some people see appearing on their skin and more particularly on the hands, darker and / or more colored spots, giving the skin a heterogeneity. These spots, classified among the unattractive benign pigment changes, are also due to a high concentration of melanin in the skin.

Many processes, mainly for cosmetic purposes, have therefore been developed in an attempt to eliminate or reduce the presence of these unsightly benign pigmentary changes. The elimination or reduction of the presence of these alterations is usually based on the application of depigmenting treatments, based on the reduction of melanin synthesis activity in melanocytes. The depigmenting molecules are to be distinguished from the anti-pigmenting molecules which limit the action of the stresses responsible for pigmentation due for example to ultraviolet radiation.

More precisely, a molecule is recognized as depigmenting if, in particular, it interferes with one of the stages of the biosynthesis of melanin either by inhibiting one of the enzymes involved in melanogenesis, or by intercalating as a structural analogue of one of the chemical compounds of the melanin synthesis chain, which chain can then be blocked and thus ensure depigmentation.

One of the main avenues explored to date is based on the inhibition of tyrosinase. The purpose of these treatments is to decrease or even stop the synthesis of pigment.

The main known depigmenting substances are hydroquinone and its derivatives, in particular its ethers such as monomethyl ether and monoethyl ether of hydroquinone, kojic acid, arbutin, etc.

However, there are major drawbacks linked to the use of the abovementioned depigmenting agents. Indeed, the depigmenting substances can present in particular a certain instability, a low efficiency at low concentration, a biological activity affecting other functions, etc.

For example, with regard to hydroquinone and its derivatives, although these compounds have a certain effectiveness, they are unfortunately not free from side effects, which can make their use delicate or even dangerous. Thus, the use of harmless topical depigmenting substances exhibiting good efficacy is very particularly sought in order to effectively depigment and / or lighten, or even whiten keratin materials, in particular the skin, and / or to prevent, reduce and / or treat an alteration in the complexion of the skin or the tint of the semimucous membranes, that is to say in particular to improve the uniformity of the complexion and / or to revive the radiance of the complexion.

There therefore remains the need for a new whitening agent for keratin materials, in particular for the skin, which also makes it possible in particular to improve the uniformity of the complexion and revive the radiance of the complexion, with an action as effective as those known, not having their drawbacks, that is to say which is stable, easily formulated including in aqueous compositions, and / or effective even at low concentration.

In this regard, the applicant company has surprisingly and unexpectedly discovered that certain C-glycoside compounds with a specific acid, ester or amide group exhibited good depigmenting activity of keratinous substances as well as an action making it possible to prevent, reduce and / or treat an alteration in the complexion of the skin or the tint of the semi-mucous membranes, that is to say in particular an activity which makes it possible to improve the uniformity of the complexion and to revive the radiance of the complexion, even at low concentration.

A first object of the invention is a method for treating keratin materials, in particular the skin, for depigmenting, lightening and / or bleaching keratin materials, in particular the skin of the face and / or the body, and / or for preventing , reduce and / or treat an alteration in the complexion of the skin or the tint of the semi-mucous membranes using at least one compound of formula (I), or at least one cosmetic composition comprising at least one compound of formula (I) , said formula (I) being the following formula:

(l) as well as their solvates such as hydrates, their optical, geometric isomers, tautomers and their base or acid salts, organic or inorganic, formula (I) in which:

- S * denotes a monosaccharide sugar radical or denotes a polysaccharide sugar radical comprising from 2 to 5 saccharide unit (s), each saccharide unit (the saccharide unit in the case of a monosaccharide or each saccharide unit in the case of polysaccharides) comprising one or more hydroxy groups optionally substituted with a radical R 'chosen from:

i) (Ci-Ce) alkyl; or ii) an acetyl radical;

said monosaccharide or polysaccharide radical which cannot comprise an (hemi) acetal or (hemi) aminal function;

said monosaccharide or polysaccharide radical which may also comprise one or more amino groups NRbR _c with Rb and R _c , identical or different, representing a hydrogen atom, or an acetyl group, or a group protecting the amino function such as ( Ci-C6) alkyl (thio) carbonyl;

said mono or polysaccharide radical being linked to the rest of the molecule by a bond between the carbon atom Ci of one of the sugars of said mono or polysaccharide radical, this bond possibly being anomeric a or β;

- R represents a group chosen from:

i) hydroxy; this hydroxy can be in the alcoholate 0 form; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), sodium (Na ⁺ ), potassium ( K ⁺ ), magnesium (Mg ²⁺ ), calcium (Ca ²⁺ ), or ammonium; (when R is in the alcoholate form, it forms with the carbonyl in the alpha position a carboxylate function COO; M ⁺ with M ⁺ as defined above) ii) (Ci-Cis) alkoxy, saturated or unsaturated;

iii) optionally substituted aryloxy such as phenyloxy or phenoxy;

iv) optionally substituted aryl (C1-C6) alkoxy such as benzyloxy;

v) a radical (B1)

(B1) in which:

• Ri and R _o independently of one another denote a hydrogen atom or a methyl radical, it being understood that Ri and R _o cannot simultaneously denote a methyl radical;

• w = 1 to 10, limits included; or iv) amino -NR1R2 with Ri and R2, independent of each other, representing:

o - for Ri:

i) a hydrogen atom;

ii) a group (Ci-Cwjalkyle;

iii) a (C2-C18) alkenyl group;

iv) an aryl (Ci-C4) alkyl group optionally substituted in particular by at least one hydroxy and / or (Ci-C4) saturated or unsaturated alkoxy group; or

v) an optionally substituted aryl or hereroaryl radical;

o - for R2:

i) a hydrogen atom;

ii) an (Ci-Cis) alkyl group;

iii) a (C2-Cis) alkenyl group;

iv) an aryl (Ci-C4) alkyl group optionally substituted in particular by at least one hydroxy and / or (Ci-C4) saturated or unsaturated alkoxy group;

v) an optionally substituted aryl or hereroaryl radical;

vi) a radical (ΒΊ):

in which :

Rh and Rk independently of one another denote a hydrogen atom or a methyl radical, it being understood that Rh and Rk cannot simultaneously denote a methyl radical;

- y = 1 to 10, limits included; or vii) a radical (B’2):

in which :

- i = 0 or 1;

R4 represents a hydrogen atom or R4 is chosen from the radicals (a1) to (a32) described below:

Me

(A13)

Me (a18)

(a19) (a20)

(A21)

(A22)

O

(a23) (a24) (325)

(a27) (a28) (a29) (a30)

Me (a32)

Or R4 can form with Ri and the nitrogen atom which carries Ri, a saturated heterocycle of formula A1, A2ouA3:

Rô means

i) a hydroxy radical -OH;

ii) an alcoholate -O; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), or an alkaline cation such as Na ⁺ , K ⁺ , or an alkaline earth cation such as Mg ²⁺ , Ca ²⁺ ), or an ammonium cation;

iii) a saturated or unsaturated (Ci-Ce) alkoxy radical;

iv) a radical -NRfR _g with Rf and R _g , identical or different, representing a hydrogen atom, or a (Ci-Ce) alkyl group;

- Or Ri and R ₂ form with the nitrogen atom to which they are attached a heterocycloalkyl, optionally substituted such as piperazino, piperidino, or morpholino.

The asterix "*" denotes the point of attachment of the radical with the rest of the compound.

The present invention also relates to the cosmetic use of at least one compound of formula (I) as well as its solvates such as hydrates, its optical, geometric isomers, tautomers and / or its cosmetically acceptable salts, as active for depigmenting, lightening and / or bleaching keratinous materials, in particular the skin of the face and / or body, and / or to prevent, reduce and / or treat an alteration in the complexion of the skin or the tint of the semi-mucous membranes .

The inventors have in fact demonstrated that the above-mentioned compounds of formula (I) as defined in the present invention exhibit a depigmenting, lightening or even whitening activity of keratin materials, in particular of the skin. More particularly, it has been shown, as detailed in the experimental part below, that these compounds of formula (I) reduce the synthesis of melanin.

In particular, according to this first aspect, the present invention aims to protect the cosmetic use of at least one compound of formula (I) as defined in the present invention or one of its solvates such as hydrates, its isomers optical, geometric, tautomeric and / or cosmetically acceptable salts thereof, for the treatment of at least one unsightly benign pigmentary change.

According to this first aspect also, the present invention relates to the cosmetic use of at least one compound of formula (I) as defined in the present invention or one of its solvates such as hydrates, its optical, geometric isomers, tautomers and / or its cosmetically acceptable salts to improve the uniformity of the complexion and / or revive the radiance of the complexion.

Preferably, the present invention relates to the cosmetic use of at least one compound of formula (IIIa), (llb), (Ile), (Ilia), (IIIb), (IIIc), (IIId), and / or ( llle) as defined in the present invention below, preferably at least one compound chosen from compounds 1 to 5, as well as their solvates such as hydrates, their optical, geometric isomers, tautomers and / or their cosmetically salts acceptable, to improve the uniformity of the complexion and / or revive the radiance of the complexion.

The compounds of formula (I) as defined in the present invention or one of their cosmetically acceptable salts are not, to date, known to be used for depigmenting, lightening or even bleaching keratin materials, in particular the skin, nor to improve the uniformity of the complexion, nor to revive the radiance of the complexion.

The present invention also aims to protect a non-therapeutic cosmetic treatment process for depigmentation, lightening and / or bleaching of keratin materials, in particular the skin of the face and / or the body and / or prevention, reduction and / or for treatment of an alteration in the complexion of the skin or in the tint of the semi-mucous membranes comprising at least one step consisting in applying to said keratin materials and in particular the skin of the face and / or of the body at least one composition comprising at least at least one compound of formula (I) or one of its solvates such as hydrates, its optical, geometric isomers, tautomers and / or its cosmetically acceptable salts as defined in the present invention.

In a particular embodiment, the present invention also aims to protect a non-therapeutic cosmetic treatment process for depigmentation, lightening and / or bleaching of keratin materials, in particular the skin of the face and / or the body and / or prevention, reduction and / or treatment of an alteration of the complexion of the skin or the tint of the semi-mucous membranes comprising at least one step consisting in applying keratin materials and in particular the skin of the face and / or body at least one composition comprising at least one compound of formula (lia), (llb), (Ile), (Ilia), (lllb), (lllc), (llld), and / or (llle) as defined in the present invention below, preferably at least one compound chosen from compounds 5, as well as their solvates such as hydrates, their optical, geometric isomers, tautomers and / or their cosmetically acceptable salts.

For the purposes of the present invention, the term "prevent" or "prevention" means reducing, at least in part, the risk of occurrence of a given phenomenon, ie in the present invention an alteration of the skin tone or the color of the semi-mucous membranes.

The subject of the invention is also new compounds of formula (I) as defined below, as well as their solvates such as hydrates, their optical, geometric isomers, tautomers and / or their cosmetically acceptable salts, in particular and their basic or acid salts, organic or mineral

The invention also relates to a method of cosmetic treatment of keratin materials, in particular of the skin, comprising the application to said materials, comprising a cosmetic composition comprising at least one compound of formula (I), or in particular at least one compound of formula (lia), (llb), (Ile), (Ilia), (lllb), (IIle), (IlId), and / or (Ille) described below.

For the purposes of the present invention, the term “keratin materials” means the skin and its annexes.

By "skin" is meant the entire skin of the body, including the scalp, mucous membranes and semi-mucous membranes.

By "appendages of the skin" is meant the hairs, the eyelashes, the hair, and the nails. More particularly, the skin of the décolleté, the neck and the face, the hands, the armpits and in particular the skin of the face are considered in the present invention.

According to another particular mode of the invention, the composition is intended for topical administration on keratin materials such as the skin.

Preferably the hydroxy radicals of the radical S * are not substituted or are all substituted by the same group R ’as defined above, in particular by an acetyl group.

Preferably the optional amino group (s) NRbRc of the radical S * denote (s) N H Rb with Rb denoting all a hydrogen atom or all an acetyl group.

Preferably, the hydroxyl radicals of the radical S * are not substituted, the optional amino group (s) NRbRc of the radical S * denote (s) NHRb with Rb denoting all a hydrogen atom or all an acetyl group.

Within the meaning of the present invention, and unless a different indication is given:

saturated or unsaturated rings, optionally condensed, can also be optionally substituted;

the “alkyl” radicals are hydrocarbon radicals, saturated, linear or branched, generally C1-C18, particularly C1-C15, as C1-C14 alkyl group, mention may in particular be made of methyl, ethyl, isopropyl, n- propyl, n-butyl, t-butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl and n-tetradecyl;

the “alkenyl” or “alkenyl” radicals are hydrocarbon radicals, linear or branched, C 2 -C 18 unsaturated; preferably comprising one or more double bonds, conjugated or not, such as ethylene, propylene, butylene, pentylene, methyl-2-propylene, prenyl and decylene;

the “aryl” radicals are mono or polycyclic carbon radicals, condensed or not, preferably comprising from 6 to 30 carbon atoms and of which at least one ring is aromatic; preferably the aryl radicals are chosen from phenyl, biphenyl, naphthyl, indenyl, anthracenyl, and tetrahydronaphthyl and more particularly aryl denotes phenyl;

the “alkoxy” or “alkoxy” radicals are alkyl-oxy radicals with alkyl as defined above, the alkyl part of the alkoxy is generally C1-C18, preferably C1-C10, more preferably C1-C6, such as methoxy, ethoxy, propoxy and butoxy, when unsaturated is mentioned this implies that the alkoxy group can represent an alkenyl-oxy group with alkenyl as defined above;

the “cycloalkyl” radicals are C4-C8 cycloalkyl radicals, preferably the cyclopentyl and cyclohexyl radicals; the cycloalkyl radicals can be cycloalkyl radicals substituted, in particular by alkyl, alkoxy, carboxylic acid, hydroxy, amine and ketone groups;

the “heterocycloalkyl” radicals are heterocyclic radicals comprising from 4 to 8 members, saturated or partially unsaturated, non-aromatic, which comprises from 1 to 3 heteroatom in particular chosen from oxygen, sulfur and nitrogen, preferably morpholino radicals, piperazino and piperidino; the heterocycloalkyl radicals can be radicals substituted, in particular by alkyl, alkoxy, carboxylic acid, hydroxy, amine and ketone groups;

the “aryl” or “heteroaryl” radicals can be substituted by at least one atom or group carried by at least one carbon atom, chosen from:

i) (Ci-Cio) alkyl, preferably Ci-Cs, optionally substituted by one or more radicals chosen from hydroxy radicals, (Ci-C4) optionally unsaturated alkoxy, (poly) hydroxy-C2-C4 alkoxy, acylamino, amino substituted by two identical or different C1-C4 alkyl radicals, optionally carrying at least one hydroxy group or, the two radicals being able to form, with the nitrogen atom to which they are attached, a heterocycle comprising from 5 to 7-membered, preferably 5 or 6-membered, saturated or unsaturated, optionally substituted, optionally comprising another heteroatom identical or different from nitrogen;

ii) halogen;

iii) hydroxy;

iv) C1-C4 alkoxy;

v) C1-C10 alkoxycarbonyl;

vi) C2-C4 (poly) hydroxyalkoxy;

vii) C2-C4 alkylcarbonyloxy, preferably -O-acetyl or acetyloxy;

viii) 5- or 6-membered heterocycloalkyl;

ix) 5 or 6-membered heteroaryl, and optionally substituted by a (C1-C4) alkyl radical, preferably methyl;

x) amino substituted by one or two identical or different C1-C6 alkyl radicals optionally carrying at least: a) a hydroxy group, b) amino optionally substituted by one or two optionally substituted C1-C3 alkyl radicals, said alkyl radicals being able to form, with the nitrogen atom to which they are attached, a heterocycle comprising from 5 to 7 members, saturated or unsaturated optionally substituted optionally comprising at least one other heteroatom different or not from nitrogen, c) a group quaternary ammonium -N ⁺ R'R ”R '”, Q' for which R ', R ”, R'”, identical or different represent a hydrogen atom, or a C1-C4 alkyl group; and Q 'represents the anionic counterion such as the halide, d) a heteroaryl radical with 5 or 6 members, and optionally substituted by a (C1-C4) alkyl radical, preferably methyl;

xi) acylamino (-N (R) -C (O) -R ') in which the radical R is a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxy group and the radical R 'is a C1-C2 alkyl radical;

xii) carbamoyl ((R) 2N-C (O) -) in which the radicals R, which may or may not be identical, represent a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxy group;

xiii) alkylsulfonylamino (R'S (O) 2-N (R) -) in which the radical R represents a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxy group and the radical R 'represents a C1-C4 alkyl radical, a phenyl radical;

xiv) aminosulfonyl ((R) 2N-S (O) 2-) in which the radicals R, which may or may not be identical, represent a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxy group, xv) carboxy in acid or salified form (preferably with an alkali metal or ammonium, substituted or not);

xvi) cyano;

xvii) benzyloxycarbonyl;

xviii) polyhaloalkyl, preferably trifluoromethyl;

xix) a phenylcarbonyloxy group optionally substituted by one or more hydroxy groups; and xx) a phenyl group optionally substituted by one or more hydroxy groups;

the “heteroaryl” radicals are radicals comprising in at least one ring one or more heteroatoms particularly chosen from O, N and S, preferably O or N, optionally substituted by in particular one or more alkyl, alkoxy, carboxy, hydroxy, amine groups or ketone, and at least one cycle of which is aromatic. These rings can contain one or more oxo groups on the heteroaryl carbon atoms; among the heterocyclic radicals which can be used, mention may in particular be made of furyl, pyrannyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, thienyl, pyrimidinyl groups; optionally, the heterocyclic groups are condensed groups such as benzofurannyl, chromenyl, xanthenyl, indolyl, isoindolyl, quinolyl, isoquinolyl, chromannyl, isochromannyl, indolinyl, isoindolinyl, coumarinyl, isocoumarinyl, these groups possibly being substituted, in particular by one or several OH groups;

the “protective group” or “PG” of the “hydroxy” or “amino” function is known to a person skilled in the art, the two works “Protective Groups in Organic Synthesis”, TW Greene, John Willey & Sons ed ., NY, 1981, pp. 193217; "Protecting Groups", P. Kocienski, Thieme, 3 ^rd ed., 2005.

In particular, the protective group is chosen from:

(C1-C6) alkyl (thio) carbonyl such as formyl, acetyl or t-butylcarbonyl;

(di) (tri) halo (Ci-C6) alkyl (thio) carbonyl such as trifluoroacethyl (TFA);

(Ci-C6) alkoxy (thio) carbonyl such as methoxycarbonyl, ethoxycarbonyl, isobutyloxycarbonyl, t-butyloxycarbonyl (BOC), vinyloxycarbonyl, allyloxycarbonyl;

(di) (tri) halo (Ci-C6) alkoxy (thio) carbonyl such as 2,2,2-trichloroethylcarbonyl;

(C1-C6) alkylthio-thiocarbonyl;

(Di) (tri) halo (Ci-C6) alkylthio-thiocarbonyl;

(di) (C1-C6) (alkyl) aminocarbonyl;

(Di) (Ci-C6) (alkyl) aminothiocarbonyl;

arylcarbonyl optionally substituted as phenylcarbonyl, 2,4,6-trimethylphenylcarbonyl;

optionally substituted aryloxycarbonyl such as p-nitrophenoxy-carbonyl;

aryl (Ci-C6) optionally substituted alkoxycarbonyl such as benzyloxycarbonyl or Cbz, p-methoxy-benzyloxycarbonyl, 3,4-dimethoxybenzyl-oxycarbonyl, o-nitrobenzyloxycarbonyl, p-nitrobenzyl-oxycarbonyl, 2-bromobenzyloxycarbonyl (2-bromo) and 2-chlorobenzyl-oxycarbonyl (2-chloroZ), 4-nitrobenzyloxycarbonyl (nitro-Z), heteroaryl (C1-C6) alkoxycarbonyl such as 9-fluorenylmethoxycarbonyl (FMOC) or nicotinoyl;

(di) (C1-C6) (alkyl) aminocarbonyl such as dimethylaminocarbonyl;

(C1-C6) (alkyl) arylaminocarbonyl;

carboxy;

optionally substituted aryl such as phenyl, dibenzosuberyl, or 1,3,5cycloheptatrienyl;

optionally substituted heteroaryl; including in particular the cationic or non-cationic heteroaryl, comprising from 1 to 4 following heteroatoms:

i) 5-, 6- or 7-membered monocyclics such as furanyl or furyl, pyrrolyl or pyrryl, thiophenyl or thienyl, pyrazolyl, oxazolyl, oxazolium, isoxazolyl, isoxazolium, thiazolyl, thiazolium, isothiazolyl, isothiazolium, 1,2,4-triazol 1,2,4-triazolium,

1.2.3- triazolyl, 1,2,3-triazolium, 1,2,4-oxazolyle, 1,2,4-oxazolium, 1,2,4-thiadiazolyle,

1.2.4- thiadiazolium, pyrylium, thiopyridyl, pyridinium, pyrimidinyl, pyrimidinium, pyrazinyl, pyrazinium, pyridazinyl, pyridazinium, triazinyl, triazinium, tetrazinyl, tetrazinium, azepine, azepinium, azepinazinepinazinepinazinepinazinepinazinepinazin, epinephinyl, epinephinyl, epinephine, epinephine

ii) 8 to 11-membered bicyclics such as indolyl, indolinium, benzoimidazolyl, benzoimidazolium, benzoxazolyl, benzoxazolium, dihydrobenzoxazolinyl, benzothiazolyl, benzothiazolium, pyridoimidazolyl, pyridoimidazolium, thienocycloheptadienyl groups, or thienocycloheptadienic groups) C1-C4) alkyl as methyl, or polyhalo (C1-C4) alkyl as trifluoromethyl;

iii) or following tricyclic ABC:

in which the two rings A, C optionally comprise a heteroatom, and the ring B is a 5, 6 or 7-membered ring, particularly 6-membered and contains at least one heteroatom such as pypéridyle, pyranyl;

optionally substituted heterocycloalkyl, optionally cationic, the heterocycloalkyl group represents in particular a saturated or partially saturated monocyclic group with 5, 6 or 7 members comprising from 1 to 4 heteroatoms chosen from oxygen, sulfur and nitrogen, such as di / tetrahydrofuranyl , di / tetrahydrothiophenyl, di / tetrahydropyrrolyl, di / tetrahydropyranyl, di / tetra / hexahydrothiopyranyl, dihydropyridyl, piperazinyl, piperidinyl, tetramethylpiperidinyl, morpholinyl, di / tetra / hexahydroetyrin groups tetra / hexahydroazin C1-C4) alkyl, oxo or thioxo preferably tetrahydropyranyl TH P; where the heterocycle represents the following grouping:

/

Andans which R ' ^c , R' ^d , R ' ^e , R' ^f , R ' ⁹ and R' ^h , identical or different represent a hydrogen atom or a group (Ci-C4) alkyl, or then two group R ' ⁹ with R' ^h , and / or R ' ^e with Reform an oxo or thioxo group, or else R' ⁹ with R ' ^e together form a cycloalkyl; and v represents an integer inclusive between 1 and 3; preferably R ' ^c to R' ^h represent a hydrogen atom; and An ^- represents a counterion;

isothiouronium -C (NR ' ^c R' ^d ) = N ⁺ R ' ^e R'^f; An ^- with R ' ^c , R' ^d , R ' ^e and R' ^f , identical or different, represent a hydrogen atom or a (CiC4) alkyl group; preferably R ' ^c to R' ^f represent a hydrogen atom; and An ^- represents a counterion;

isothiourea -C (NR ' ^c R' ^d ) = NR '^e; with R ' ^c , R' ^d and R ' ^e as defined above;

(di) aryl (Ci-C4) alkyl or triaryl (Ci-C4) optionally substituted alkyl such as 9-anthracenyl-methyl, phenylmethyl (benzyl), diphenylmethyl or triphenylmethyl optionally substituted by one or more groups chosen in particular from halogen, (Ci -C4) alkyl, (Ci-C4) alkoxy such as methoxy, hydroxy, (Ci-C4) alkylcarbonyl, (di) (Ci-C4) (alkyl) amino such as dimethylamino, nitro;

(di) heteroaryl (Ci-C4) akyl or triheteroaryl (Ci-C4) akyl optionally substituted, the heteroaryl group is in particular, cationic or not, monocyclic, comprising 5 or 6 members and from 1 to 4 heteroatoms chosen from nitrogen, oxygen and sulfur, such as the pyrrolyl, furanyl, thiophenyl, pyridyl, pyridyl N-oxide groups such as 4-pyridyl or 2-pyridyl-Nooxide, pyrylium, pyridinium, triazinyl, optionally substituted by one or more groups such that particularly methyl alkyl, advantageously the (di) heteroaryl (C1-C4) akyl is (di) heteroarylmethyl or (di) heteroarylethyl;

CR ¹ R ² R ³ with R ¹ , R ² and R ³ identical or different, representing a halogen atom such as (tri) (di) halo (Ci-C4) alkyl such as 2,2,2-trichloroethyl or a group chosen from:

- (C1-C4) alkyl such as methyl;

- (Ci-C4) alkoxy;

- optionally substituted aryl such as phenyl optionally substituted by one or more groups such as (Ci-C4) alkyl, (Ci-C4) alkoxy, hydroxy;

- optionally substituted heteroaryl such as thiophenyl, furanyl, pyrrolyl, pyranyl, pyridyl, optionally substituted by a (CiC4) alkyl group;

- P (Z ¹ ) R ' ¹ R' ² R ' ³ with R' ¹ , and R ' ² identical or different represent a hydroxy group, (Ci-C4) alkoxy or alkyl, R' ³ represents a hydroxy group or ( C1-C4) alkoxy, and Z ¹ represents an oxygen or sulfur atom;

(C2-Ce) alkylene in particular allyl H2C = CH-CH2-;

optionally substituted arylsulfonyl such as p-toluenesulfonyl (Tos);

sterically hindered cycloalkyl such as the adamantyl group;

sterically hindered cycloalkyloxy (thio) carbonyl such as 1-adamantyloxycarbonyl (Adoc) or 1- (adamantyl) -1-methylethoxy-carbonyl (Adpoc);

(Ci-C4) alkoxy (Ci-C4) optionally substituted alkyl such as methoxymethyl (MOM), ethoxyethyl (EOM) and isobutoxymethyl;

(tri) (di) halo (C1-C4) alkyl such as 2,2,2-trichloroethyl;

ReRrRgSi- with R _e , Rf, and R _g , identical or different, representing a group (Ci-Ce) alkyl, optionally substituted aryl, (di) aryl (Ci-C4) optionally substituted alkyl, triaryl (Ci-C4) alkyl optionally substituted, such as benzyl, in particular chosen from trimethylsilyl or TMS, triethylsilyl, isopropylidimethylsilyl, terbutyldimethylsilyl or TBDMS, (triphenylmethyl) dimethylsilyl, t-butyldiphenylsilyl, methyldiisopropylsilyl, methyl-di-silyl, di-tylilyl) xylylsilyl, triisopropylsilyl, triphenylsilyl;

or then two contiguous hydroxy groups can be protected by an alkylene group * -C (R ') (R ^m ) - (C (R ^k ) (R ^j )) q- * as drawn below:

with R ^j , R ^k , R ¹ , and R ^m , identical or different, representing a hydrogen atom or a (Ci-C4) alkyl, (poly) halo (Ci-C4) alkyl, optionally substituted aryl group such as phenyl, aryl (Ci-C4) alkyl such as benzyl, (poly) halo (Ci-C4) alkoxy, (Ci-C4) alkoxy, halogen, (di) (Ci-C4) (alkyl) amino, hydroxy, or so two groups R ^j and R ^k and / or R ¹ , and R ^m form together with the carbon atom which carry them an oxo group or a (hetero) clycloalkyl such as cyclohexyl or cyclopropyl; q is 0, 1,2 or 3, preferably * -C (R ') (R ^m ) - (C (R ^k ) (R ^j )) q- * represents a methylene, ethylene, propylene, dimethylmethylene, * - C (CH3) 2- * or diphenylmethylene * -C (Ph) 2- *, cyclopentylidene, cyclohexylidene, cycloheptylidene, benzylidene, p-methoxybenzylidene, 2,4-dimethoxybenzylidene, methoxymethylene and ethoxymethylene;

The asterix "*" denotes the point of attachment of the radical with the rest of the compound.

In the context of the present invention, the sugar radicals, whether it is a monosaccharide or a polysaccharide radical, do not contain an acetal group, a hemiacetal group, an aminal group or a hemiaminal group;

Acceptable solvates for the compounds used 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 (hydrates) or of linear or branched alcohols such as ethanol or isopropanol.

The salts of the compounds (I) which comprise at least one acid function can be chosen from metal salts, for example aluminum (Al ³⁺ ), zinc (Zn ²⁺ ), manganese (Mn ²⁺ ) or copper (Cu ²⁺ ), alkaline salts, for example lithium (Li ⁺ ), sodium (Na ⁺ ) or potassium (K ⁺ ), or alkaline earth, for example calcium (Ca ²⁺ ) or magnesium (Mg ²⁺ ). It can also be ammonium derivatives of formula NHY or organic salts such as ammoniums of formula Y3NIT, NY3 denoting an organic amine, the radicals Y being identical or different, two or three radicals Y being able to form a ring in pairs with the nitrogen atom which carries them or NY3 can designate an aromatic amine. The organic amines are for example alkylamines, such as for example methylamine, dimethylamine, trimethylamine, triethylamine or ethylamine, or hydroxyalkylamines, such as for example 2-hydroxyethylamine, bis (2-hydroxyethyl) amine or tri- (2-hydroxyethyl) amine, or cycloalkylamines, such as for example bicyclohexylamine or glucamine, piperidine, or pyridines and the like, for example collidine, quinine or quinoline, or basic amino acids, such as, for example, lysine or arginine;

The salts of the compounds of formula (I) which comprise at least one amine function can be salts of organic acid such as citric acid, lactic acid, tartaric acid, aspartic acid, glutamic acid, acetic acid, formic acid, acid trifluoroacetic, hydrochloric acid, glycolic acid, or malic acid.

In the case where the compounds according to the invention are in the form of a salt, the cations are of course found in an amount ensuring the electroneutrality of the compounds of formula (I).

The salts of the compounds of formula (I) which contain at least one acid function can be advantageously chosen from the metal salts Cu ²⁺ , Mn ²⁺ and Zn ²⁺ , the alkaline salts Li ⁺ , Na ⁺ and K ⁺ and the salts alkaline earth Ca ²⁺ and Mg ²⁺ .

According to another variant, the salts of the compounds of formula (I) according to the invention which comprise at least one acid function can be advantageously chosen from ammoniums, preferably from the amino acid salts of basic character such as for example lysine or arginine or from the salts of diethanolamine or triethanolamine.

Preferably, the compounds (I) which comprise at least one acid function are in the form of sodium salts Na ⁺ .

Preferably, the compounds (I) which comprise at least one acid function are in the form of potassium salts K ⁺ .

Preferably, the compounds (I) which comprise at least one acid function are in the form of calcium salts Ca ²⁺ .

According to a particular embodiment of the invention, the compounds of formula (I) are such that, R represents a hydroxy radical or an alcoholate radical 0; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), sodium (Na ⁺ ), potassium ( K ⁺ ), magnesium (Mg ²⁺ ), calcium (Ca ²⁺ ), or ammonium.

As an example of compounds of formula (I) according to this embodiment, mention may be made in particular of the following compound as well as its salts, isomers, solvates:

compound S * = D-Glucose 1 O Chiral I OH

According to another particular embodiment of the invention, the compounds of formula (I) are such that, R represents an (Ci-Cis) alkoxy group, preferably saturated, more preferably a (Ci-Ce) alkoxy group, in particular ethoxy.

According to another particular embodiment of the invention, the compounds of formula (I) are such that, taken together or separately, R represents a radical (B1):

(B1) where:

• Ri and R _o independently of one another denote a hydrogen atom or a methyl radical, it being understood that Ri and R _o cannot simultaneously denote a methyl radical;

• w = 1 to 10, preferably from 1 to 5, more preferably from 1 to 3, limits included.

According to another particular embodiment of the invention, the compounds of formula (I) are such that, taken together or separately, R represents an amino group -NR1R2 with Ri and R2, independent of each other, representing:

i) a hydrogen atom;

ii) an (Ci-Cis) alkyl group; preferably (Ci-Cwjalkyle such as (Ci-C4) alkyl and / or (Cs-Cwjalkyle;

iii) or Ri and R2 form with the nitrogen atom to which they are attached a heterocycloalkyl, optionally substituted such as piperazino, piperidino, or morpholino.

According to this embodiment, preferably Ri and R2, independent of each other, represent:

i) a hydrogen atom;

ii) an (Ci-Cis) alkyl group; preferably (C 1 -C 18 alkyl and in particular a methyl or n-tetradecyl radical.

According to a first form of this embodiment Ri and R2 are identical and chosen from

i) a hydrogen atom;

ii) an (Ci-Cis) alkyl group; preferably (Ci-C4) alkyl and in particular a methyl radical.

As an example of a compound of formula (I) according to this embodiment, mention may be made, for example, of the compounds below, as well as their salts, isomers or solvates:

compound S * = D-xylose 3 Chiral Me n_ / ^N 'Me II 0 ho' OH compound S * = L-rhamnose 4 Chiral Me \ Me ,, - z ^N Me ΗΟ ^Χ γ ^ζ ^ ΌΗ ÔH

According to a second form of this variant, Ri denotes a hydrogen atom and R2 denotes a (Ci-Ci8) alkyl group; preferably (C 1 -C 6 alkyl) and in particular a (C 8 -C 16) alkyl radical such as n-tetradecyl.

As an example of a compound of formula (I) according to this embodiment, mention may be made, for example, of compound 5 below, as well as its salts, isomers or solvates:

compound

S * = D-xylo-furanose

According to another particular embodiment of the invention, the compounds of formula (I) are such that, taken together or separately, R represents an amino group -NR1R2 with Ri and R ₂ , independent of each other, representing:

o for Ri:

i) a hydrogen atom; or ii) a (Ci-Cis) alkyl group; preferably (C1-C4) alkyl; more preferably methyl;

preferably Ri represents a hydrogen atom;

o for R2:

a radical (ΒΊ) such as:

in which :

Rh and Rk independently of one another denote a hydrogen atom or a methyl radical, it being understood that Rh and Rk cannot simultaneously denote a methyl radical;

- y = 1 to 10, preferably from 1 to 5, more preferably from 1 to 3, limits included.

According to another particular embodiment of the invention, the compounds of formula (I) are such that, taken together or separately, R represents an amino group -NR1R2 with Ri and R ₂ , independent of each other, representing:

o for Ri:

i) a hydrogen atom; or ii) a (Ci-Cis) alkyl group; preferably (C1-C4) alkyl; more preferably methyl;

preferably Ri represents a hydrogen atom;

o for R2:

a radical (B’2):

in which :

- i = 0 or 1;

- R ₄ represents a hydrogen atom or R ₄ is chosen from the radicals (a1) to (a32) described below:

Me

(A13)

Me (a18)

OH

(A19)

Me ^^ O (a20)

(A21)

(A22)

(a23) (a24) (325)

Me

(a27) (a28)

Me (a32)

Or R ₄ can also form, with Ri and the nitrogen atom which carries Ri, a saturated heterocycle of formula A1, A2 or A3:

Rô means

i) a hydroxy radical -OH;

ii) an alcoholate -O; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), or an alkaline cation such as Na ⁺ , K ⁺ , or an alkaline earth cation such as Mg ²⁺ , Ca ²⁺ ), or an ammonium cation;

iii) a saturated or unsaturated (Ci-Ce) alkoxy radical; or iv) a radical -NRfR _g with Rf and R _g , identical or different, representing a hydrogen atom, or a (Ci-Ce) alkyl group.

According to another particular embodiment of the invention, the compounds of formula (I) are such that, taken together or separately, R represents an amino group -NR1R2 with Ri and R2, independent of each other, representing:

o for Ri:

i) a hydrogen atom;

ii) an (Ci-Cis) alkyl group; preferably (C1-C4) alkyl; more preferably methyl;

and preferably Ri represents a hydrogen atom;

o for R2:

i) an optionally substituted aryl or heteroaryl radical, in particular an optionally substituted phenyl radical;

iii) an optionally substituted heteroaryl radical;

iv) an aryl (C1-C4) -alkyl radical, in particular a phenyl-C1-C4) alkyl radical and preferably R2 denotes an optionally substituted phenyl radical.

According to another particular embodiment of the invention, the compounds of formula (I) are such that, taken together or separately, R represents an optionally substituted aryloxy group, in particular an optionally substituted phenoxy group.

According to another particular embodiment of the invention, the compounds of formula (I) are such that, taken together or separately, R represents an optionally substituted aryl (C1-C6) - alkoxy group such as an optionally substituted benzyloxy group.

It is understood that for the compounds of formula (I) as defined above when S * represents a monosaccharide radical then it may be in pyranose form (the sugar heterocycle which constitutes it is 6-membered) or furanose (the heterocycle sugar which constitutes it is 5-membered); and when S * represents a poly5 saccharide radical it comprises the chain of 2 to 5 saccharide units identical or different between them which can be in furanose or pyranose form. Preferably when S * represents a polysaccharide radical, the polysaccharide is a disaccharide which results from the chain of 2 pyranose units or the chain of a saccharide unit in furanose form and of a unit in pyranose form or the chain a saccharide unit in pyranose form and a unit in furanose form; whether for the monosaccharide or polysaccharide radical, each saccharide unit can be in the levorotatory L or dextrorotatory form, and in the anomeric form a or β.

According to a preferred embodiment, the sugar radical S * represents a monosaccharide radical of which the heterocycle which constitutes it contains 4 or 5 carbon atoms, of formula S * ’below:

R _a representing a hydrogen atom, a (Ci-C4) alkyl group such as methyl or a (poly) hydroxy (Ci-C4) alkyl group such as hydroxymethyl or dihydroxy-1,2-ethyl, the hydroxy function (s) of the poly) hydroxy (Ci-C4) alkyl group being substituted by A as defined below;

it being understood that the radical R _a is in position Cs if the sugar motif is in pyranose form or in C4 if it is in furanose form;

Rb representing a hydrogen atom or a (Ci-C4) alkyl group preferably hydrogen;

R _c representing a hydrogen atom, or a group protecting the amine function such as Rd-C (O) -, identical in the case of several hydroxyl functions, with Rd representing a (Ci-C4) alkyl group, preferably R _c representing an acetyl group CH3-C (O) -,

R _e represents a hydrogen atom or a group -CH2-OA;

A representing a hydrogen atom, a (Ci-C6) alkyl group, or a hydroxy protecting group such as Rd-C (O) - as defined above and in particular acetyl CH3-C (O) -, or else when n is greater than or equal to 2 and two groups A-0 are contiguous then two groups A can together form a chain (Ci-Ce) alkylene, linear or branched;

preferably all the protecting groups of A are identical;

n is 1.2 or 3 and m is 0 or 1.

According to a particular form of the invention, m is zero.

According to another preferred embodiment, the sugar radical S * represents a polysaccharide radical consisting of 2 to 5 saccharide units, in particular 2 to 3, and preferably 2 saccharide units, linked together via an oxygen atom (oxy ) in 1-> 4 (Ci of a saccharide unit -> C4 of the other saccharide unit) or 1-> 3 (Ci 5 of a saccharide unit -> C3 of the other saccharide unit) or 1-> 6 (Ci of a saccharide unit -> C6 of the other saccharide unit) in which each saccharide unit consists of a heterocycle comprising 4 or 5 carbon atoms, of formula S * ”below:

Formula S * ”in which p and q represent integers inclusive between 0 and 4 with p + q inclusive between 1 and 4, particularly between 1 and 2, preferably p + q = 1; R _a , identical or different, are as defined above, Rb, identical or different, are as defined above, R _c , identical or different, are as defined above, R _e , identical or different, are as defined previously, A identical or different, are as previously defined, m, identical or different, are as previously defined, n, identical or different, are as previously defined; it being understood that the two sugar patterns between the hooks q and p can be interchanged, ie represent the following sequence:

According to a preferred variant of the invention, the compounds of formula (I) are such that:

- S * represents a monosaccharide sugar radical, in pyranose or furanose form, said monosaccharide being chosen from: glucose, galactose, mannose, xylose, lyxose, fucose, arabinose, rhamnose, quinovose, fructose, sorbose, talose, N-acetylglucosamine, N-acetylgalactosamine, glucosamine, galactosamine; or S * represents a disaccharide chosen from: lactose, maltulose, palatinose, lactulose, tonsillosis, turanose, cellobiose, isomaltose, rutinose, maltose, preferably S * represents a sugar radical chosen among glucose, galactose, mannose, xylose, rhamnose, frustose, sorbose, N-acetylglucosamine, N-acetylgalactosamine, glucosamine, galactosamine, lactose, cellobiose, and maltose, and preferably chosen from glucose, xylose and rhamnose ;

said radical S * comprising one or more radicals -OR _S and optionally one or two radicals -NHR ' _S , said mono or disaccharide radical being linked to the rest of the molecule by a bond between the carbon atom C ¹ of the sugar or d 'one of the sugars and this bond can be anomeric a or β;

- R represents:

i) a hydroxy radical; may be in carboxylate O form; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), sodium (Na ⁺ ), potassium ( K ⁺ ), magnesium (Mg ²⁺ ), calcium (Ca ²⁺ ), or ammonium;

ii) an (Ci-Cis) alkoxy group, preferably (C ₂ -C6) alkoxy such as ethoxy;

iii) a (C ₂ -C 18) alkenyloxy radical, preferably (C ₂ -C 6) alkenyloxy such as prenyloxy;

iv) an optionally substituted aryloxy radical such as phenyloxy or phenoxy;

v) an aryl (Ci-Ce) alkoxy radical optionally substituted in particular by at least one hydroxy and / or (Ci-C4) saturated or unsaturated alkoxy group, in particular an aryl (Ci-C4) alkoxy radical such as benzyloxy;

v) a radical such as:

or :

• Ri and R _o independently of one another denote a hydrogen atom or a methyl radical, it being understood that Ri and R _o cannot simultaneously denote a methyl radical;

• w = 1 to 10, preferably 1 to 5, preferably 1 to 3, limits included;

vi) an amino radical -NR1R2 with Ri and R ₂ , independent of each other, representing: o for Ri:

- a hydrogen atom;

a saturated or unsaturated (Ci-Cis) alkyl group, preferably saturated and more preferably saturated with C1-C6 such as methyl;

o for R2:

- a hydrogen atom;

a saturated or unsaturated (Ci-Cis) alkyl group, preferably saturated and more preferably saturated with C1-C6 such as methyl;

- an aryl (Ci-C4) alkyl group optionally substituted in particular by at least one hydroxy and / or (Ci-C4) saturated or unsaturated alkoxy group;

- an aryl or hereroaryl radical, optionally substituted, preferably by one or more groups, identical or different, (Ci-Ce) alkyl, hydroxy, C1-C4 alkoxy, C1-C6 alkoxycarbonyl, or carboxy;

- a radical such as:

or :

• Rh and Rk independently of one another denote a hydrogen atom or a methyl radical, it being understood that Rh and Rk cannot simultaneously denote a methyl radical;

• y = 1 to 10, preferably 1 to 5, preferably 1 to 3;

- a radical such as:

or :

- i = 0 or 1;

FA represents a hydrogen atom or a radical R4 chosen from the radicals (a1) to (a32) described below:

h ₂ n

NH

Me ^ (a1)

Me

(A13)

Me (a 18)

(a 19) (a20) _(a2 i) (a22)

O

(a23) (a24) ( ^a25 )

Me

(a27) (a28) (a29) (a30)

OH

ΜβΆ (a31)

Me (a32)

R4 can also form, with Ri and the nitrogen atom which carries Ri, a saturated heterocycle of formula A1, or A2 or A3:

Rô means

i) a hydroxy radical -OH;

ii) an alcoholate -O; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), or an alkaline cation such as Na ⁺ , K ⁺ , or an alkaline earth cation such as Mg ²⁺ , Ca ²⁺ ), or an ammonium cation;

iii) a saturated or unsaturated (Ci-Ce) alkoxy radical;

iv) a radical -NRfR _g with Rf and R _g , identical or different, representing a hydrogen atom, or a (Ci-Ce) alkyl group.

or Ri and R2 form with the nitrogen atom to which they are attached a heterocycloalkyl, optionally substituted such as piperazino, piperidino, or morpholino.

- R _s represents a hydrogen atom or a methyl radical or an acetyl radical, said radicals R _s being preferably all identical and preferably denoting a hydrogen atom or an acetyl radical;

- R ' _s represents a radical chosen from a hydrogen atom or an acetyl radical.

More preferably, the compounds of formula (I) are chosen from the compounds of formulas (I '), (I ”), (I” ”), (a), (l” a), (l ”” a) and (l'b) following:

(l'b) as well as their solvates such as hydrates, their optical, geometric isomers, tautomers and their base or acid salts, organic or inorganic,

Formulas (I ’), (I”), (I ””), (a), (l ”a), (l” ”a) and (I'b) in which:

- R is as defined above, preferably represents a group:

i) hydroxy; this hydroxy can be in the alcoholate 0 form; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), sodium (Na ⁺ ), potassium ( K ⁺ ), magnesium (Mg ²⁺ ), calcium (Ca ²⁺ ), or ammonium; (when R is in alcoholate form, it forms with the carbonyl in the alpha position a carboxylate function COO; M ⁺ with M ⁺ as defined above) ii) (Ci-Cis) alkoxy; preferably C1-C4 alkoxy and more preferably ethoxy;

iii) amino -NR’iR’2 with R’1 and R’2, independent of each other, representing:

o for R’1:

i) a hydrogen atom;

ii) an (Ci-Cis) alkyl group, preferably (Ci-Ce) alkyl, preferably methyl;

o for R’2:

i) a hydrogen atom;

ii) an (Ci-Cis) alkyl group;

iii) a radical such as:

O where: j = 0 or 1;

R ' ₄ represents a hydrogen atom or R' ₄ is chosen from the radicals (a1) to (a32) described below:

(A2)

Me ^ (a1)

Me

(A13)

Me (a18)

(A21)

(A22)

O

(a23) (a24) (a25)

Me OH

(327) (a28) (a29) (a30) (a31)

Me (a32)

R ' ₄ can also form with R'i and the nitrogen which carries R'i a saturated heterocycle, of formula A1, or A2 or A3:

R® denotes

i) a hydroxy radical -OH;

ii) an alcoholate -O; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), or an alkaline cation such as Na ⁺ , K ⁺ , or an alkaline earth cation such as Mg ²⁺ , Ca ²⁺ , or an ammonium cation;

iii) a saturated or unsaturated (Ci-Ce) alkoxy radical;

iv) a radical -NRfR _g with Rf and R _g , identical or different, representing a hydrogen atom, or a (Ci-Ce) alkyl group.

And preferably R® represents a hydroxy radical, an alcoholate -O; M ⁺ , a saturated alkoxy (CiCe) radical, in particular methoxy or ethoxy, or an amino radical NH 2.

or else R’1 and R® form, with the nitrogen atom to which they are attached, a heterocycloalkyl, optionally substituted such as piperazino, piperidino, or morpholino.

- R ”is as defined above, preferably represents a hydrogen atom or an acetyl radical, and preferably a hydrogen atom;

- R ’” represents a hydrogen atom, or a (Ci-Ce) alkyl group, or a group

-CH2-OR "with R" as defined above in particular hydrogen or an acetyl radical, and preferably a hydrogen atom. Preferably R "represents a hydrogen atom, or a (Ci-C) alkyl group such as methyl, or a group -CH2OR" with R "denoting a hydrogen atom or an acetyl radical.

According to a particular embodiment, the compounds of the invention are of formula (I ’). By way of example of a compound of formula (I ’), mention may be made of the compounds 2, 3 and 4 described above, as well as their salts, solvates and isomers.

According to another particular embodiment of the invention, the compounds of the invention are of formula (I ”).

According to another particular embodiment of the invention, the compounds of the invention are of formula (I "").

According to another particular embodiment of the invention, the compounds of the invention are of formula (a). According to another particular embodiment of the invention, the compounds of the invention are of formula (l ”a). According to another particular embodiment of the invention, the compounds of the invention are of formula (1 ”).

According to another particular embodiment of the invention, the compounds of the invention are of formula (I'b). By way of example of a compound of formula (b), mention may be made of compound 5 described above, as well as its salts, solvates and isomers.

According to a particular embodiment, S * and S * 'represent a monosaccharide chosen from glucose, galactose, mannose, xylose, lyxose, fucose, arabinose, rhamnose, ribose, deoxy-ribose, quinovose, fructose, sorbose, talose, threose, erythrose, N-acetylglucosamine, N-acetylgalactosamine, glucosamine, galactosamine.

In particular, S * and S * 'represent a monosaccharide chosen from D-glucose, D-galactose, D-mannose, D-xylose, L-xylose, D-lyxose, L-lyxose, L-fucose, L-arabinose, D-arabinose, L-rhamnose, L-ribose, D-ribose, 2-deoxyD-ribose, 2-deoxy-L-ribose, D-quinovose, D-fructose, L-sorbose, D-talose, D-threose, D-erythrose, L-threose, L-erythrose, N-acetyl-D-glucosamine, N-acetyl- D- galactosamine, D-glucosamine, D-galactosamine. Preferably, S denotes a monosaccharide chosen from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose, L-fucose, L-arabinose, L-rhamnose, D -ribose, 2-deoxyD-ribose, D-quinovose, D-fructose, L-sorbose, D-talose, D-threose, Derythrose, N-acetyl-D-glucosamine, N- acetyl- D-galactosamine, D-glucosamine, D-galactosamine.

Advantageously, S * and S * ’represent a monosaccharide chosen from glucose, xylose, rhamnose, mannose and galactose or a disaccharide chosen from lactose, maltose and cellobiose. In particular, S * denotes a monosaccharide chosen from D-glucose, D-xylose, L-rhamnose, D-mannose, D-galactose or a disaccharide chosen from D-lactose, D-maltose and D-cellobiose .

Preferably, S * and S * ’represent a sugar chosen from glucose, xylose, rhamnose and lactose. More particularly, S * and S * ’denote a sugar chosen from D-glucose, D-xylose, L-rhamnose and D-lactose. Preferably, S * and S * ’denote glucose, rhamnose or xylose. In particular, S * and S * ’denote Dglucose, L-rhamnose or D-xylose.

According to another particular embodiment, S * and S * ”represent a polysaccharide and in particular a disaccharide chosen from lactose, maltulose, palatinose, lactulose, tonsillosis, turanose, cellobiose, isomaltose, rutinose, maltose.

According to a particular embodiment, the radical S * and S * ”represent a polysaccharide and in particular a disaccharide chosen from D-lactose, maltulose, palatinose, lactulose, tonsillosis, D-turanose, D- cellobiose, isomaltose, rutinose, D-maltose.

According to another particular embodiment, R represents an amino group -NR'iR'2 with R'1 and R ' ₂ , independent of each other, representing:

o for R’1: a hydrogen atom or a (Ci-Cis) alkyl group, preferably (C1Ce) alkyl, preferably a methyl;

o for R ' ₂ : a radical such as:

R '

or :

j = 0 or 1; preferably j = 0;

R’4 represents a hydrogen atom when j = 1, and in the other cases (ie when j = 0), R’4 is chosen from the radicals described below:

R’4 can also form with R’i and the nitrogen which carries R \ an alipsaturated heterocycle of formula A1, or A2 or A3:

R’6 designates

i) a hydroxy radical -OH;

ii) an alcoholate -O; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), or an alkaline cation such as Na ⁺ , K ⁺ , or an alkaline earth cation such as Mg ²⁺ , Ca ²⁺ , or an ammonium cation;

iii) a saturated alkoxy (Ci-Ce) radical, preferably methoxy or ethoxy;

iv) an amino radical -NH2.

According to another particular embodiment, R represents an amino group -NR’iR’2 with R’1 and R’2, independent of each other, representing:

o for R’i: a hydrogen atom or a (Ci-Cw) alkyl group, preferably (Ci-Ce) alkyl, preferably methyl;

o for R ' ₂ : a hydrogen atom or a (Ci-Ci6) alkyl group, preferably a methyl or an n-tetradecyl;

- R ”is as defined above, preferably represents a hydrogen atom or an acetyl radical, and preferably a hydrogen atom;

- R ’” represents a hydrogen atom, or a (Ci-C6) alkyl group, or a group

-CH2-OR "with R" as defined above in particular hydrogen or an acetyl radical, and preferably a hydrogen atom. Preferably R "represents a hydrogen atom, or a (Ci-C) alkyl group such as methyl, or a group -CH2OR" with R "denoting a hydrogen atom or an acetyl radical.

According to this embodiment, according to a first variant, R’1 and R’2 are identical.

According to a second variant of this embodiment, R’1 and R’2 are different and preferably R’1 denotes a hydrogen atom.

According to another particular embodiment, R represents a hydroxy group, this hydroxy can be in the alcoholate O form; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), sodium (Na ⁺ ), potassium ( K ⁺ ), magnesium (Mg ²⁺ ), calcium (Ca ²⁺ ), or ammonium; (when R is in alcoholate form, it forms with the carbonyl in the alpha position a carboxylate function COO; M ⁺ with M ⁺ as defined above)

- R ”is as defined above, preferably represents a hydrogen atom or an acetyl radical, and preferably a hydrogen atom;

- R ’” represents a hydrogen atom, or a (Ci-C6) alkyl group, or a group

-CH2-OR "with R" as defined above in particular hydrogen or an acetyl radical, and preferably a hydrogen atom. Preferably R "represents a hydrogen atom, or a (Ci-C) alkyl group such as methyl, or a group -CH2OR" with R "denoting a hydrogen atom or an acetyl radical.

The subject of the invention is also the new compounds of formula (IIa), as well as their solvates and / or isomers and / or salts for which:

(Ha)

With:

- S * i denotes a monosaccharide sugar radical chosen from: D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose, L-fucose, L-arabinose, D- arabinose, L-rhamnose, D-quinovose, D-fructose, L-sorbose, D-talose, N-acetyl-D-glucosamine, N-acetyl-D-galactosamine, D-glucosamine, D-galactosamine;

the saccharide unit comprising one or more hydroxyl groups optionally substituted (s) by a radical R _'is selected from:

i) (Ci-Ce) alkyl; or ii) an acetyl radical;

said monosaccharide radical not being able to comprise an (hemi) acetal or (hemi) aminal function;

said monosaccharide radical being linked to the rest of the molecule by a bond between the carbon atom Ci of said monosaccharide radical, this bond possibly being anomeric a or β;

- R’3 represents a group chosen from:

i) a hydrogen atom; ii) (Ci-Cis) alkyl, saturated or unsaturated;

iii) optionally substituted aryl such as phenyl;

iv) optionally substituted aryl (Ci-Ce) alkyl such as benzyl;

Being heard that :

- when S * i denotes a D-glucose, R'3 cannot be methyl or ethyl, and R'3 is different from a hydrogen atom when all of its hydroxy groups are substituted by an acetyl group (R ' _a = acetyl);

- When S * i denotes a D-xylose, R’3 cannot be a methyl or a (Ci5-Cie) alkyl;

- when S * i denotes a D-galactose, R'3 cannot be hydrogen, and R'3 is different from methyl or ethyl when all of its hydroxy groups are substituted by an acetyl group (R ' _a = acetyl );

- when S * i denotes a D-mannose, R’3 cannot be hydrogen or methyl;

- when S * i denotes an L-rhamnose, R’3 is different from a hydrogen atom or a methyl group when all of its hydroxy groups are substituted by an acetyl group (R’a = acetyl);

- when S * i denotes an L-fucose, R’3 cannot be hydrogen;

- when S * i denotes a D-arabinose, R’3 cannot be methyl;

- when S * i denotes a D-talose, R'3 is different from a hydrogen atom when all of its hydroxy groups are substituted by an acetyl group (R ' _a = acetyl);

- when S * i denotes an N-acetyl-D-glucosamine, R'3 cannot be an ethyl, and R'3 is different from a hydrogen atom when all of its hydroxy groups are substituted by an acetyl group ( R ' _a = acetyl);

- the compounds of formulas (IIa) have a molar mass of less than 800 Da and do not comprise more than 3 cycles in total.

When R'3 denotes a hydrogen atom, as mentioned above, the corresponding compounds of formula (IIa) can be in the form of salts (carboxylates COO ', M ⁺ , with M ⁺ having the definition mentioned above).

Preferably, S * i denotes a sugar chosen from D-glucose or D-xylose, more preferably D-glucose.

Preferably, the hydroxy groups of S * i are not substituted

Preferably, R’3 represents a hydrogen atom or a (Ci-Cis) alkyl group, preferably saturated, and more preferably a C2-C6 alkyl group, in particular ethyl.

Among the compounds of formula (IIa), mention may in particular be made of compound 2 (and / or its solvates and / or its salts):

compound S * i = D-glucose

The subject of the invention is also the new compounds of formulas (llb), as well as their solvates and / or isomers and / or salts for which:

(Hb)

With:

- S * 2 denotes a monosaccharide sugar radical or denotes a polysaccharide sugar radical comprising 2 saccharide units, each saccharide unit (the saccharide unit in the case of a monosaccharide or each saccharide unit in the case of polysaccharides) comprising one or more groups hydroxy optionally substituted with a radical R'b chosen from:

i) (Ci-Ce) alkyl; or ii) an acetyl radical;

said monosaccharide or polysaccharide radical which cannot comprise an (hemi) acetal or (hemi) aminal function;

said monosaccharide or polysaccharide radical which may also comprise one or more amino groups NRbRc with Rb and R _c , identical or different, representing a hydrogen atom, or an acetyl group, or a group protecting the amino function such as (C2 C6) alkyl (thio) carbonyl;

said mono or polysaccharide radical being linked to the rest of the molecule by a bond between the carbon atom Ci of one of the sugars of said mono or polysaccharide radical, this bond possibly being anomeric a or β;

- R ”3 represents a group chosen from:

i) hydrogen atom; ii) (C2-C14) alkyl, saturated or unsaturated;

Being heard that :

- when S * 2 denotes a monosaccharide, R ”3 cannot be hydrogen or ethyl;

- when S * 2 denotes a monosaccharide in the pyranose form, R ”3 cannot be n-butyl;

- the compounds of formulas (llb) have a molar mass of less than 800 Da and do not comprise more than 3 cycles in total.

When R'3 denotes a hydrogen atom, as mentioned previously, the corresponding compounds of formula (IIb) can be in the form of salts (COO carboxylates; M ⁺ , with M ⁺ having the definition mentioned above).

According to a particular form of the invention, S * 2 denotes a monosaccharide as defined above with the exception of D-glucose, D-galactose, D-mannose, Dxylose, D-lyxose, L-fucose , L-arabinose, D-arabinose, L-rhamnose, D-quinovose, D-fructose, L-sorbose, D-talose, N-acetyl-D-glucosamine, N- acetyl-D-galactosamine, D-glucosamine, and D-galactosamine.

When S * 2 denotes a disaccharide, it is preferably the following disaccharides: lactose, maltulose, palatinose, lactulose, tonsillosis, turanose, cellobiose, isomaltose, rutinose, maltose. More preferably, it is Dlactose, D-maltose or D-cellobiose.

Preferably, the hydroxy groups of S * 2 are not substituted

Preferably, R ”3 represents a hydrogen atom or a (C2-Ce) alkyl group, preferably saturated, in particular ethyl.

The subject of the invention is also the new compounds of formulas (Ile), as well as their solvates and / or isomers and / or salts for which:

(Ile) in which S *, Ri, R _o and w are as defined above.

- S * denotes a monosaccharide sugar radical or denotes a polysaccharide sugar radical comprising from 2 to 3 saccharide unit (s), each saccharide unit (the saccharide unit in the case of a monosaccharide or each saccharide unit in the case of polysaccharides) comprising one or more hydroxy groups optionally substituted with a radical R 'chosen from:

i) (Ci-Ce) alkyl; or ii) an acetyl radical;

said monosaccharide or polysaccharide radical which cannot comprise an (hemi) acetal or (hemi) aminal function;

said monosaccharide or polysaccharide radical which may also comprise one or more amino groups NRbRc with Rb and R _c , identical or different, representing a hydrogen atom, or an acetyl group, or a group protecting the amino function such as (C2 C6) alkyl (thio) carbonyl;

said mono or polysaccharide radical being linked to the rest of the molecule by a bond between the carbon atom Ci of one of the sugars of said mono or polysaccharide radical, this bond possibly being anomeric a or β;

- Ri and R _o independently of one another denote a hydrogen atom or a methyl radical, it being understood that Ri and R _o cannot simultaneously denote a methyl radical;

- w = 1 to 10, terminals included

Being heard that :

The compounds of formulas (Ile) have a molar mass of less than 800 Da and do not comprise more than 3 cycles in total.

Preferably, the hydroxy groups of S * are not substituted and the optional amino groups are free (-NH2) or all substituted by an acetyl group (-COCH ₃ ) (Rb = H and R _c = H or acetyl).

Preferably w is between 1 and 5, more preferably between 1 and 3.

The subject of the invention is also the new compounds of formulas (Ilia), as well as their solvates and / or isomers and / or salts for which:

With:

- S * 3 denotes a monosaccharide sugar radical chosen from: D-xylose, D-fructose, L-sorbose, N-acetyl-D-glucosamine, N-acetyl-D-galactosamine, D-glucosamine, D-galactosamine and in particular D-xylose;

the saccharide unit comprising one or more hydroxy groups optionally substituted by a radical R ′ _c chosen from:

i) (Ci-Ce) alkyl; or ii) an acetyl radical;

said monosaccharide radical not being able to comprise an (hemi) acetal or (hemi) aminal function;

said monosaccharide radical being linked to the rest of the molecule by a bond between the carbon atom Ci of said monosaccharide radical, this bond possibly being anomeric a or β;

- R ”i represents a group chosen from:

i) a hydrogen atom;

ii) an (Ci-Cis) alkyl group;

iii) a (C2-Cis) alkenyl group;

- R ”2 represents a group chosen from:

i) a hydrogen atom;

ii) an (Ci-Cis) alkyl group;

iii) a (C2-Cis) alkenyl group;

iv) an aryl (Ci-C4) alkyl group optionally substituted in particular by at least one hydroxy and / or (Ci-C4) saturated or unsaturated alkoxy group;

v) an optionally substituted aryl or hereroaryl radical;

or R ”i and R” 2 form with the nitrogen atom to which they are attached a heterocycloalkyl, optionally substituted such as piperazino, piperidino, or morpholino.

Being heard that :

The compounds of formulas (Ilia) have a molar mass of less than 800 Da and do not comprise more than 3 cycles in total.

Preferably S * 3 denotes D-xylose.

Preferably, the hydroxy groups of S * 3 are not substituted.

Preferably, R ”i denotes a hydrogen atom or a C1-C4 alkyl group such as in particular a methyl group. Preferably, RA denotes a hydrogen atom or a C1-C16 alkyl group such as in particular a methyl or n-tetradecyl group.

Among the compounds of formula (IIa), the new compounds 3 and 5 (and / or their solvates and / or their salts) are more particularly preferred:

compound S * 3 = D-xylose 3 Me <] η Me HO T '' OH OH compound S * 3 = D-xylo-furanose 5 HO OH °

The subject of the invention is also the new compounds of formulas (IIIb), as well as their solvates and / or isomers and / or salts for which:

O (lllb)

With:

- S% denotes a monosaccharide sugar radical or denotes a polysaccharide sugar radical comprising from 2 to 3 saccharide unit (s), each saccharide unit (the saccharide unit in the case of a monosaccharide or each saccharide unit in the case of polysaccharides) comprising one or more hydroxy groups optionally substituted by an R'd radical chosen from:

i) (Ci-Ce) alkyl; or ii) an acetyl radical;

said monosaccharide or polysaccharide radical which cannot comprise an (hemi) acetal or (hemi) aminal function;

said monosaccharide or polysaccharide radical which may also comprise one or more amino groups NRbRc with Rb and R _c , identical or different, representing a hydrogen atom, or an acetyl group, or a group protecting the amino function such as (C2 -C6) alkyl (thio) carbonyl; with the exclusion of monosaccharides of the 5-amino-furanose type;

said mono or polysaccharide radical being linked to the rest of the molecule by a bond between the carbon atom Ci of one of the sugars of said monosaccharide radical, this bond possibly being anomeric a or β;

- R "’ i represents a group chosen from:

i) a hydrogen atom;

ii) an (Ci-Cis) alkyl group;

iii) a (C2-Cis) alkenyl group;

- R ’” 2 represents a group chosen from:

i) a (Ci-Cis) alkyl group; or ii) a (C2-Cis) alkenyl group;

iii) an aryl (Ci-C4) alkyl group optionally substituted in particular by at least one hydroxy and / or (Ci-C4) saturated or unsaturated alkoxy group;

iv) an optionally substituted aryl or hereroaryl radical;

or then R '”i and R” ” ₂ form with the nitrogen atom to which they are attached a heterocycloalkyl, optionally substituted such as piperazino, or morpholino; the piperidine cycle is excluded;

It being understood that, in the case where R "’ i represents a hydrogen atom:

- when S% denotes a D-galactose, R ’” 2 cannot be an alkyl or alkenyl group;

- when S% denotes a monosaccharide, R ’” 2 cannot be a substituted or unsubstituted benzyl group;

- when S% denotes a pyranose-type monosaccharide, R ’” 2 cannot be a substituted or unsubstituted phenyl group, or a 2-benzothiazolyl group, or a 2-benzimidazolyl group;

Being heard that

The compounds of formulas (IIIb) have a molar mass of less than 800 Da and do not comprise more than 3 cycles in total;

And that the following compound is excluded:

When S% denotes a monosaccharide, said monosaccahride is different from Dxylose, D-fructose, L-sorbose, N-acetyl-D-glucosamine, N-acetyl-Dgalactosamine, D-glucosamine, D-galactosamine.

When S% denotes a disaccharide, it is preferably the following disaccharides: lactose, maltulose, palatinose, lactulose, tonsillosis, turanose, cellobiose, isomaltose, rutinose, maltose. More preferably, it is Dlactose, D-maltose or D-cellobiose.

Preferably, the hydroxy groups of S% are not substituted

Preferably, R '”i denotes a hydrogen atom or a C1-C4 alkyl group such as in particular a methyl radical. Preferably, R '”i denotes a methyl group. Preferably, R '” ₂ denotes a hydrogen atom or a C1-C4 alkyl group such as in particular a methyl radical.

Among the compounds of formula (IIIb), mention may be made in particular of the new compound (and / or its solvates and / or its salts):

compound S% = L-rhamnose 4 Me ΗΟ '^ /' Όη ⁰ OH

The subject of the invention is also the new compounds of formulas (IIIll), as well as their solvates and / or isomers and / or salts for which:

O o (lllc)

With:

- S * 3 denotes a monosaccharide sugar radical chosen from: D-xylose, D-fructose, L-sorbose, N-acetyl-D-glucosamine, N-acetyl-D-galactosamine, D-glucosamine, D-galactosamine;

the saccharide unit comprising one or more hydroxy groups optionally substituted by a radical R ′ _c chosen from:

i) (Ci-Ce) alkyl; or ii) an acetyl radical;

said monosaccharide radical not being able to comprise an (hemi) acetal or (hemi) aminal function;

said monosaccharide radical being linked to the rest of the molecule by a bond between the carbon atom Ci of one of the sugars of said monosaccharide radical, this bond possibly being anomeric a or β;

- R ”i represents a group chosen from:

i) a hydrogen atom;

ii) an (Ci-Cis) alkyl group;

iii) a (C2-Cis) alkenyl group;

- i = 0 or 1;

- R4 represents a hydrogen atom or R4 is chosen from the radicals (a1) to (a32) described below:

NH ^H (a2)

H ₂ N (a1)

OH ; Me '' ^ (a6)

Me

(A13)

(A16)

Me (a18)

(a19) (a20)

(A22)

(A23)

(a28) (a29) (a30) (a31) (a32) (a27)

R4 can also form, with R ”i and the nitrogen atom carrying R” i, a saturated heterocycle of formula A1, or A2 or A3:

Rô means

i) a hydroxy radical -OH;

ii) an alcoholate -O; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), or an alkaline cation such as Na ⁺ , K ⁺ , or an alkaline earth cation such as Mg ²⁺ , Ca ²⁺ ), or an ammonium cation;

iii) a saturated or unsaturated (Ci-Ce) alkoxy radical;

iv) a radical -NRfR _g with Rf and R _g , identical or different, representing a hydrogen atom, or a (Ci-Ce) alkyl group.

Being heard that

The compounds of formulas (IIIc) have a molar mass of less than 800 Da and do not comprise more than 3 cycles in total.

Preferably, the hydroxy groups of S * 3 are not substituted

Preferably, R ”i denotes a hydrogen atom or a C1-C4 alkyl group such as in particular a methyl radical. Preferably, R "i denotes a hydrogen atom.

Preferably R6 denotes an ethoxy hydroxyl group, or NH2.

When R6 denotes a hydrogen atom, the corresponding compounds of formula (IIIc) can of course be in the form of salts (carboxylate).

Preferably i = 0 and R4 represents a hydrogen atom or a radical chosen from the following radicals (a1) or (a5) or (a16):

^Me \ HCL * x /

J (a1) (a5)

The subject of the invention is also the new compounds of formulas (IIId), as well as their solvates and / or isomers and / or salts:

(IIId)

With:

- S * denotes a monosaccharide sugar radical or denotes a polysaccharide sugar radical comprising from 2 to 3 saccharide unit (s), each saccharide unit (the saccharide unit in the case of a monosaccharide or each saccharide unit in the case of polysaccharides) comprising one or more hydroxy groups optionally substituted with a radical R 'chosen from:

i) (Ci-Ce) alkyl; or ii) an acetyl radical;

said monosaccharide or polysaccharide radical which cannot comprise an (hemi) acetal or (hemi) aminal function;

said monosaccharide or polysaccharide radical which may also comprise one or more amino groups NRbRc with Rb and R _c , identical or different, representing a hydrogen atom, or an acetyl group, or a group protecting the amino function such as (C2 C6) alkyl (thio) carbonyl;

said mono or polysaccharide radical being linked to the rest of the molecule by a bond between the carbon atom Ci of one of the sugars of said mono or polysaccharide radical, this bond possibly being anomeric a or β;

- R ”i represents a group chosen from:

i) a hydrogen atom;

ii) an (Ci-Cis) alkyl group;

iii) a (C2-Cis) alkenyl group;

- i = 0 or 1;

- R4 represents a hydrogen atom or R4 is chosen from the radicals (a1) to (a32) described below:

Me

(A13)

Me (a18)

(a19) (a20)

(A21)

(A22)

O

(a23) (a24) ( ^a25 )

Me OH

(a27) (a28) (a29) (a30) (a31)

Me (a32)

R4 can also form, with R ”i and the nitrogen atom carrying R” i, a saturated heterocycle of formula A1, or A2 or A3:

Rô means

i) a hydroxy radical -OH;

ii) an alcoholate -O; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), or an alkaline cation such as Na ⁺ , K ⁺ , or an alkaline earth cation such as Mg ²⁺ , Ca ²⁺ , or an ammonium cation;

iii) a saturated or unsaturated (Ci-C6) alkoxy radical;

iv) a radical -NRfR _g with Rf and R _g , identical or different, representing a hydrogen atom, or a (Ci-C6) alkyl group.

It being understood that: in the case where R ”i represents a hydrogen atom and when S * denotes a monosaccharide of pyranose type, Re cannot be a methyl or a hydroxy group;

Being heard that

The compounds of formulas (IIId) have a molar mass of less than 800 Da and do not comprise more than 3 cycles in total;

And that the following compound is excluded:

[1000184-29-1]

IN L-Asparagine, N2- (3,7-anhydro-2-deoxy-D-glycero-L-gluco-octo-

Preferably, the hydroxy groups of S * are not substituted

Preferably, R ”i denotes a hydrogen atom or a C1-C4 alkyl group such as in particular a methyl radical. Preferably, R "i denotes a hydrogen atom.

Preferably R6 denotes an ethoxy hydroxyl group, or NH2.

When R ”6 denotes a hydroxy group, the corresponding compounds of formula (IlId) can of course be in the form of salts (carboxylates).

Preferably i = 0 and R4 represents a hydrogen atom or a radical chosen from the following radicals (a1) or (a5) or (a16):

^Μ θχ.

(a1) (a5) (a 16)

The subject of the invention is also the new compounds of formulas (llle), as well as their solvates and / or isomers and / or salts for which:

(IIIe)

- S * denotes a monosaccharide sugar radical or denotes a polysaccharide sugar radical comprising from 2 to 3 saccharide unit (s), each saccharide unit (the saccharide unit in the case of a monosaccharide or each saccharide unit in the case of polysaccharides) comprising one or more hydroxy groups optionally substituted with a radical R 'chosen from:

i) (Ci-Ce) alkyl; or ii) an acetyl radical;

said monosaccharide or polysaccharide radical which cannot comprise an (hemi) acetal or (hemi) aminal function;

said monosaccharide or polysaccharide radical which may also comprise one or more amino groups NRbRc with Rb and R _c , identical or different, representing a hydrogen atom, or an acetyl group, or a group protecting the amino function such as (C2 C6) alkyl (thio) carbonyl;

said mono or polysaccharide radical being linked to the rest of the molecule by a bond between the carbon atom Ci of one of the sugars of said mono or polysaccharide radical, this bond possibly being anomeric a or β;

- R ”i represents a group chosen from:

i) a hydrogen atom;

ii) an (Ci-Cis) alkyl group;

iii) a (C ₂ -C18) alkenyl group;

- Rh and Rk independently of one another denote a hydrogen atom or a methyl radical, it being understood that Rh and Rk cannot simultaneously denote a methyl radical;

- y = 1 to 10, limits included

Being heard that

The compounds of formulas (llle) have a molar mass of less than 800 Da and do not comprise more than 3 cycles in total.

Preferably, the hydroxy groups of S * are not substituted and the optional amino groups are free (-NH ₂ ) or substituted by an acetyl group (-CO-CH3) (Rb = H and R _c = H or acetyl).

Preferably there is between 1 and 5, more preferably between 1 and 3.

The preferred new compounds are compounds 1 to 5 described above.

Process for the preparation of the compounds of formula (I), in particular of the compounds of formula (lla), (llb), (Ile), (Ilia), (lllb), (Ille), (llld), and / or (llle) , of the invention

Another subject of the invention is the process for the preparation, or process for the chemical synthesis of the compounds of formula (I) as defined above for which A is different from a hydrogen atom on the one hand, and compounds of formula (I) for which A denotes a hydrogen atom and the sugar S * is a monosaccharide in pyranose or furanose form on the other hand, according to the scheme (1) described below.

The compounds of formula (II ¹ ) include certain compounds (carboxylic acids) of the formulas (11a) and (11b). The compounds of formula (II ² ) include certain compounds (esters) of the formulas (11a) and (11b), as well as the compounds of formula (Ile).

The compounds of formula (III ¹ ) include the compounds of formulas (IIIa), (IIIb), (IIIc), (IIId) and (III).

The new compounds of formulas (II ¹ ), (II ² ) and (III ¹ ) can be prepared according to the following scheme (1):

According to this scheme, if in the compound (IV), A denotes a hydrogen atom, the synthesis step 1a must be preceded by a step of protection of the radicals AO = OH of the sugar. In this case, the compounds (II ¹ ), (II ² ), as well as the compounds (III ¹ ) obtained via (II ¹ ) are obtained in the form of protected sugars (A different from H) and the compounds (II ¹ ) , (II ² ), (III ¹ ) correspondents for which A = H are obtained after a deprotection step.

The compounds (III ¹ ) can also be obtained by reaction of a compound (IV) protected or not (A = H or different from H), with a beta-ketoamide (VII) according to step 1b. If (IV) is such that A = H, then in this case (III ¹ ) is such that A = H. If (IV) is such that A is different from H, then (III ¹ ) is such that A different from H and the compound (III ¹ ) for which A = H is obtained after a step of deprotection of the hydroxyls of the sugar.

The synthetic route described in diagram (1) comprises the following steps:

- Step 1a consists in reacting a monosaccharide or a polysaccharide of formula (IV) with Meldrum acid (V), in particular in the presence of an organic base such as a tertiary amine such as triethylamine or diisopropylethylamine .

Formula (IV) in which A, R _a , Rb, Rc, Re, n, and m as defined above, p 'and q' representing an integer between 0 and 4 inclusive, with p '+ q' which is included inclusive between 0 and 4, in particular between 0 and 2, preferably p '+ q' = 0 or 1, it being understood that the two patterns in square brackets can be interchanged; the compound of formula (IV) being represented in the diagram by:

Step 1 being carried out in particular in a polar aprotic solvent such as DMF or acetonitrile, optionally heating to a temperature between 30 ° C and 100 ° C, in particular at 40-50 ° C, preferably for a duration between 1 h and 7 days, in particular between 2 and 7 days, such as 2 days, to lead to the compound with a sugar motif (VI);

- Step 2 consists in carrying out a hydrolysis of the compound (VI), in particular in an acid medium, and in particular in the presence of a weak organic acid such as acetic acid, which can also serve as solvent, or also in medium acid diluted in aqueous solution such as hydrochloric acid, in a protic polar solvent such as water, optionally heating to a temperature between 30 ° C and 120 ° C, in particular between 80 ° C and 100 ° C, such as 100 ° C, for a period of between 2 h and 24 h, in particular between 2 h and 5 h, to lead to an acidic C-glycoside compound (II ¹ ).

- Step 3 consists in reacting the acid (II ¹ ) either with an alcohol R _r -OH to lead to the ester compounds of formula (II ² ) by esterification, or with an amine RriR ^ NH to lead to the amide compounds of formula (III ¹ ) by N-acylation / amidation.

The first 2 steps are described in particular by Mata et al., Carbohydr. Res. 1990, 201, 223-31; Mata et al., Carbohydr. Res. 1992, 225, 159-61; Kôll et al., J. Carbohydr. Chem. 2000, 19, 1019-47.

Alternatively, in certain cases (in particular when R _r i and R _r 2 are alkyl groups), it may be possible to obtain amide compounds of formula (III ¹ ) directly by a Lubineau type reaction (step 1b) between the monosaccharide or the polysaccharide of formula (IV) and an acetoacetamide compound of formula (VII). The reaction takes place in particular in the presence of an inorganic base such as M + OH-, M + representing a cation, such as NaOH, or preferably a weak base such as (bi) carbonate, in particular with alkali metal (bi) carbonate. , or in the presence of an organic base such as triethylamine or diisopropylethylamine, in particular in a polar protic solvent such as water, optionally heating to a temperature between 30 ° C and 100 ° C, in particular at between 50 ° C and 60 ° C, preferably for a period of between 1 hour and 24 hours, in particular between 2 hours and 5 hours, such as 2 or 3 hours.

The compounds of formula (I) for which A denotes a hydrogen atom and the sugar is in furanose form can also be obtained according to the following scheme (2):

Diagram (2)

This alternative synthetic route includes the following stages:

- Step 1 consists in reacting a monosaccharide or a polysaccharide of formula (IV) with Meldrum's acid (V), in particular in the presence of an organic base such as a tertiary amine such as triethylamine or tert -butylamine. Step 1 being carried out in particular in a polar aprotic solvent such as DM F or acetonitrile, optionally heating to a temperature between 30 ° C and 100 ° C, in particular at 45-49 ° C, preferably for a period of between 1 h and 7 days, in particular between 2 and 7 days, such as 5 days, to lead to a lactone intermediate fused with a sugar motif in furanose form (VIII);

- Step 2a consists in carrying out a hydrolysis of the compound (VIII), in particular in an acid medium, and in particular in an acid medium diluted in aqueous solution such as hydrochloric acid, in a polar protic solvent such as water, optionally heating to a temperature between 30 ° C and 120 ° C, in particular between 80 ° C and 100 ° C, such that

100 ° C, for a period of between 2 h and 24 h, to yield an acidic glycoside compound (II ¹ ) in furanose form. Alternatively, step 2 may also consist in opening the lactone (VIII) in an aqueous basic medium, in particular in the presence of a strong inorganic base such as sodium hydroxide or potassium hydroxide, in a polar protic solvent such as water, at room temperature or optionally heating to a temperature between 30 ° C and 120 ° C, in particular between 80 ° C and 100 ° C, such as 100 ° C, for a period between 2 h and 24 h, to drive to an acidic glycoside compound (II ¹ ) in furanose form;

- Step 2b consists in opening the lactone compound (VIII) with an alcohol Rr-OH, in particular in an acid medium, such as in the presence of hydrochloric acid, in a polar aprotic solvent such as THF, dioxane or DMF (alcohol R _r -OH can itself be used as solvent), possibly heating to a temperature between 30 ° C and 160 ° C, in particular between 80 ° C and 120 ° C, such as 100 ° C , for a period of between 2 h and 24 h, to yield a C-glycoside ester compound (II ² ) in furanose form. Alternatively the lactone (VIII) can be opened by the alcohol R _r OH previously deprotonated by a strong base such as Na or NaH, to form the corresponding alcoholate;

- Step 2c consists in opening the lactone compound (VIII) with an amine RriRrêNH, in a polar aprotic solvent such as THF, dioxane or DMF (the amine RriR ^ NH can itself be used as solvent), optionally heating to a temperature between 30 ° C and 160 ° C, in particular between 80 ° C and 120 ° C, such as 100 ° C, for a period between 2 h and 24 h, to lead to a compound C -glycoside amide (III ¹ ) in furanose form.

All the reagents are obtained by conventional methods known to those skilled in the art. The latter will take care to protect or unprotect according to the synthesis steps. It may be necessary to carry out a step of protecting the hydroxy groups (groups A) and / or the amino groups (group NRbRc) of the sugar unit (IV), before the first step, then to proceed to their possible deprotection after the third step. For example :

The compounds can be obtained from a sugar (IV) with a free OH group (s) or substituted with a C1-C6 alkyl group or with a C1-C6 alkylcarbonyl group, or with an OH protected by a protective group, said protective group being accessible according to the methods described by Peter GM Wuts and Theodora W. Greene, in Greene's Protective Groups in Organic Synthesis, Fourth Edition, Wiley, 2006; processes for the alkylation and acylation of hydroxyls in sugars are known and are described in particular in Durantie, Estelle et al, Chemistry - A European Journal, 18 (26), 8208-8215 (2012).

The sugar (IV) can also contain one or more amino group (s) substituted (s) by the same C1-C6 alkylcarbonyl group, or by a PG such as those described by Peter GM Wuts and Theodora W. Greene, in Greene's Protective Groups in Organic Synthesis, Fourth Edition, Wiley, 2006. The processes for the alkylation or acylation of sugar hydroxyls are known to a person skilled in the art and are described in particular in: Durantie, Estelle et al, Chemistry - A European Journal , 18 (26), 8208-8215 (2012).

The alkylation step of the hydroxy group is generally carried out by treatment with a base, often relatively strong, of NaH type, tBuOK, tBuONa, in the presence of an alkylating agent such as an alkyl halide, in a polar aprotic solvent. such as DMF, NMP, THF, ACN, acetone.

N-acylation methods are also well known to those skilled in the art and consist of reacting the amine with either a reactive derivative of carboxylic acid such as an anhydride or an acid halide (acid chloride ), or a carboxylic acid activated in situ via a coupling agent such as HOBt, EDCI, CDI, DCC, HATU, PyBOP, in the optional presence of an organic base such as DIEA or TEA, or a mineral base such as NaOH, and optionally DMAP in equimolar or catalytic amount, in a polar aprotic solvent such as DCM, THF, DMF, or ACN, or optionally protic like water.

Esterification methods are generally carried out by treating the alcohol with either a reactive carboxylic acid derivative such as an anhydride or an acid halide (acid chloride), or a carboxylic acid activated in situ. via a coupling agent such as HOBt, EDCI, CDI, DCC, optionally in the presence of a base such as pyridine, triethylamine or diisopropylethylamine, sodium acetate, soda, and optionally DMAP in equimolar or catalytic amount , in a polar aprotic solvent such as ACN, pyridine, DCM, THF, acetone, or possibly protic like water. Alternatively, the hydroxy can be treated with a carboxylic acid in an acid medium (APTS, anhydrous HCl, H2SO4), with a device for removing the water formed, such as the presence of a desiccant, such as silica gel. , Na2SO4, MgSO4, P2O5 or a Dean Stark apparatus using a volatile solvent forming an azeotrope with water, such as toluene or cyclohexane.

The present invention also relates to a composition comprising, in a physiologically acceptable medium, at least one compound of formula (I), and in particular at least one compound of formula (IIa), (IIb), (Ile), (Ilia), ( IIIb), (IIle), (IIId), and / or (Ille) and more particularly at least one compound chosen from compounds 2,3, 4 and 5, as described above. The composition is in particular a cosmetic composition.

According to an advantageous form of the invention, the cosmetic composition contains at least one compound of formula (I), and in particular at least one compound of formula (lia), (llb), (Ile), (Ilia), (IIIb) , (IIle), (IIId), and / or (IIle), and more particularly at least one compound chosen from compounds 2, 3, 4, 5 as defined above and at least one additive chosen from a perfume, an agent thickener, surfactant, pigment, dye, preservative.

More particularly, the cosmetic composition according to the invention contains at least one compound chosen from compounds 1 to 5, preferably chosen from compounds 2, 3, 4 and 5 defined above, as well as their solvates such as hydrates, and their salts base or acid, organic or mineral.

The compound of formula (I), and in particular the compounds of formula (IIa), (IIb), (Ile), (Ilia), (IIlb), (IIle), (IIId), and / or (IIle) defined below. before, (each compound of formula (I) if the composition comprises several) may be present in the composition, in an amount which may be between 0.01 and 20% by weight, preferably between 0.1 to 15 % by weight, in particular between 0.5 to 10% by weight, relative to the total weight of the composition.

The composition also comprises a physiologically acceptable medium, which is preferably a cosmetically or pharmaceutically, in particular 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. In particular, the composition is suitable for topical application to the skin and the appendices.

By physiologically acceptable medium is meant a medium compatible with the skin of human beings and the appendices.

The composition according to the invention can then comprise water and / or all the adjuvants usually used in the intended field of application.

Mention may in particular be made of; organic solvents, in particular C1-C6 alcohols and C2-C10 carboxylic acid esters; carbon and / or silicone oils, of mineral, animal and / or vegetable origin; water, waxes, pigments, fillers, dyes, surfactants, emulsifiers, co-emulsifiers; cosmetic or dermatological active ingredients, UV filters, polymers, hydrophilic or lipophilic gelling agents, thickeners, preservatives, perfumes, bactericides, odor absorbers, antioxidants.

These optional adjuvants may be present in the composition in an amount of 0.001 to 80% by weight, in particular 0.1 to 40% by weight, relative to the total weight of the composition.

The composition according to the invention may constitute a makeup composition, or preferably a skin care composition, and in particular a cleansing, protective, treatment or care cream for the face, for the hands, for the feet, for the large anatomical or body folds (for example day creams, night creams, makeup remover creams, foundation creams, sunscreen creams); a fluid foundation, a cleansing milk, a body milk for protection or care, an anti-sun milk; a skin care lotion, gel or foam, such as a cleansing lotion, a hair composition.

The invention is illustrated in more detail by the following nonlimiting examples.

EXAMPLES

Example 1: synthesis of compounds 2, 3, 4 and 5

Compound 2 synthesis

Compound 1_ ([34010-29-2] / [267235-22-3]) is described for example by Mata et al., Carbohydr. Res. 1992, 225, 159-61.

To a solution of compound 1. (3 g, 7.69 mmol) in methanol (50 mL) is added K2CO3 (2.12 g, 15.37 mmol). The reaction mixture is stirred for 16 h at rt, then adjusted to pH 4 with an aqueous solution of 4N HCl. After filtration, the filtrate is evaporated to dryness. The residue is purified by chromatography on silica gel (dichloromethane / MeOH 10: 1) to give compound 2 (white solid, 1 g, Yield = 59%). ¹ H / ¹³ C NMR spectra and mass spectrometry are in agreement with the expected structure.

Compound 3 synthesis

O OH 0 0 HO ' ^L ' Y OH OH El E2 1 U-, O NaOH, H ₂ O ^HO Y oh OH 3

To a solution of D-xylose E1 (1 g, 6.7 mmol) in water (2.0 mL) is added N, Ndimethylacetoacetamide E2 (1.40 mL, 8.0 mmol) drop by drop. Then the soda (1.33 g in water at 30%) is added drop by drop while keeping the temperature below 35 ° C. The reaction mixture is stirred 45 min at 50 ° C, then allowed to return to

your. for 2h30. Butanol (1.52 g) and 37% HCl (1.41 g) are added (pH 1). After addition of ethyl acetate (2.5 mL), the mixture is stirred for 30 min and then allowed to settle. The operation is repeated with the addition of dichloromethane (2.5 mL). The residual aqueous phase is treated with 200 mg of vegetable black, and stirred for 15 min. The product is filtered through celite and rinsed with water. The filtrate obtained is neutralized to pH 10, then concentrated in vacuo. The inorganic salts are precipitated by adding ethanol then filtration and concentration, then again by adding acetone. The filtrate obtained is then purified by chromatography on silica gel (dichloromethane / MeOH 95: 5 to 85:15). The residue obtained is precipitated in dichloromethane, filtered, washed with diisopropyl ether, then recrystallized from ethanol and dried under vacuum to yield compound 3 (white solid, 144 mg, Yield = 10%).

Compound 4 synthesis

o o

E2 I

NaOH, H ₂ O

To a solution of L-rhamnose E3 (1 g, 5.5 mmol) in N, N-dimethylacetoacetamide E2 (2.40 mL, 13.7 mmol) is added sodium hydroxide (35% in water, 0.45 mL). The reaction mixture is stirred for 1 hour at 60 ° C., then allowed to return to r.t. and diluted with water. The mixture is stirred for 30 min with a DOWEX 500WX2-200 acid resin and then filtered. The aqueous phase is extracted 4 times with dichloromethane, then concentrated in vacuo. The residue is purified by chromatography on silica gel (EtOAc / MeOH 9: 1). The product obtained is dissolved in water, washed once with dichloromethane (DCM), purified in animal black and then filtered through celite. The filtrate is washed twice with DCM and the aqueous phase is concentrated in vacuo. After adding ethanol, the precipitate formed is filtered, then the filtrate is evaporated to dryness to yield compound 4 (dark green solid, 223 mg, Yield = 18%).

Compound 5 synthesis

n-tetradecyl

Compound E4 is prepared according to P. Kôll et al., J. Carbohydr. Chem. 2000, 19 (8), 101947.

Lactone E4 (253 mg, 1.44 mmol) is added to the n-tetradecylamine (1.54 g, 7.20 mmol) liquefied at 50 ° C. The reaction mixture is heated at 76 ° C for 4 h. After returning to r.t., the mixture solidifies. It is taken up in ethyl acetate, then the solid is filtered and washed with ethyl acetate. The operation is repeated 2 times. A white powder is obtained with a yield of 45%.

Example 2: Demonstration of the depigmenting effect of compounds of formula (I) suitable for the invention

Protocol

Efficacy has been demonstrated on the basis of the following test:

The measurement of the depigmenting activity (reduction in the production of melanin) of compounds of formula (I) was carried out by assaying normal human melanocytes in vitro as follows.

First, normal human melanocytes are cultured and distributed in a multi-well plate. After 24 hours, the culture medium was replaced by a medium containing the compounds of formula (I) to be evaluated. The cells were incubated 72 hours before the measurement of the final optical density which measures the quantity of melanin produced by the melanocytes. The measurement was calibrated and the compounds were tested at 100 μΜ. .

Different test campaigns have been carried out and the results are collated in the following tables.

Results

The results of the test are summarized in Table 1 below.

Table 1

% depigmentation at 100 μΜ compound Campaign 1 Campaign 2 Campaign 3 1 24% 2 29% 4 15%

From these results, it appears that the compounds of formula (I) at low concentration have depigmenting properties.

Example 3 Composition according to the invention

A depigmenting gel for the skin is prepared. It includes the following ingredients (% by weight relative to the total weight of the composition):

ingredients % by weight relative to the total weight of the composition Compound 2 3 Carbomer (sold under the name Carbopol® 981 by the company Lubrizol) 1 conservative qs water qs 100

The composition according to the invention applied to the skin makes it possible to homogenize the complexion, in particular to remove dark spots.

Claims (9)

1. Process for the treatment of non-therapeutic keratin materials, for depigmenting, lightening and / or bleaching keratin materials, in particular the skin of the face and / or the body, and / or for preventing, reducing and / or treating a change in skin tone the skin or the color of the semi-mucous membranes using at least one compound of formula (I), or at least one cosmetic composition comprising at least one compound of formula (I) as well as its solvates such as hydrates, its isomers optical, geometric, tautomers and its base or acid salts, organic or mineral: (l) in which: - S * denotes a monosaccharide sugar radical or denotes a polysaccharide sugar radical comprising from 2 to 5 saccharide unit (s), each saccharide unit (the saccharide unit in the case of a monosaccharide or each saccharide unit in the case of polysaccharides) comprising one or more hydroxy groups optionally substituted with a radical R 'chosen from: i) (Ci-Ce) alkyl; or ii) an acetyl radical; said monosaccharide or polysaccharide radical which cannot comprise an (hemi) acetal or (hemi) aminal function; said monosaccharide or polysaccharide radical which can also comprise one or more amino groups NRbRc with Rb and R _c , identical or different, representing a hydrogen atom, or an acetyl group, or a group protecting the amino function such as (Ci C6) alkyl (thio) carbonyl; said mono or polysaccharide radical being linked to the rest of the molecule by a bond between the carbon atom Ci of one of the sugars of said mono or polysaccharide radical, this bond possibly being anomeric a or β; - R represents a group chosen from: i) hydroxy; this hydroxy can be in the alcoholate 0 form; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), sodium (Na ⁺ ), potassium ( K ⁺ ), magnesium (Mg ²⁺ ), calcium (Ca ²⁺ ), or ammonium; (when R is in the alcoholate form, it forms with the carbonyl in the alpha position a carboxylate function COO; M ⁺ with M ⁺ as defined above) ii) (Ci-Cis) alkoxy, saturated or unsaturated; iii) optionally substituted aryloxy such as phenyloxy or phenoxy; iv) optionally substituted aryl (Ci-Ce) alkoxy such as benzyloxy; v) a radical (B1) (B1) in which: • Ri and R _o independently of one another denote a hydrogen atom or a methyl radical, it being understood that Ri and R _o cannot simultaneously denote a methyl radical; • w = 1 to 10, limits included; or iv) amino -NR1R2 with Ri and R2, independent of each other, representing: o - for Ri: i) a hydrogen atom; ii) an (Ci-Cis) alkyl group; iii) a (C2-Cis) alkenyl group; iv) an aryl (Ci-C4) alkyl group optionally substituted in particular by at least one hydroxy and / or (Ci-C4) saturated or unsaturated alkoxy group; or v) an optionally substituted aryl or hereroaryl radical; o - for R2: i) a hydrogen atom; ii) an (Ci-Cis) alkyl group; iii) a (C2-Cis) alkenyl group; iv) an aryl (Ci-C4) alkyl group optionally substituted in particular by at least one hydroxy and / or (Ci-C4) saturated or unsaturated alkoxy group; v) an optionally substituted aryl or hereroaryl radical; vi) a radical (ΒΊ): in which : Rh and Rk independently of one another denote a hydrogen atom or a methyl radical, it being understood that Rh and Rk cannot simultaneously denote a methyl radical; - y = 1 to 10, limits included; or vii) a radical (B’2): in which: - i = 0 or 1; R4 represents a hydrogen atom or R4 is chosen from the radicals (a1) to (a32) described below: Me (a13) Me (a18) (a19) (a20) (a21) (a22) O (a23) (a24) (a25) (a27) (a28) (a29) (a30) Me (a32) Or R4 can form with Ri and the nitrogen atom which carries Ri, a saturated heterocycle of formula A1, A2 or A3: Rô means i) a hydroxy radical -OH; ii) an alcoholate -O; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), or an alkaline cation such as Na ⁺ , K ⁺ , or an alkaline earth cation such as Mg ²⁺ , Ca ²⁺ ), or an ammonium cation; iii) a saturated or unsaturated (Ci-C6) alkoxy radical; iv) a radical -NRfR _g with Rf and R _g , identical or different, representing a hydrogen atom, or a (Ci-C6) alkyl group; - or Ri and R2 form with the nitrogen atom to which they are attached a heterocycloalkyl, optionally substituted such as piperazino, piperidino, or morpholino. 2. Method according to the preceding claim in which the compound (s) of formula (I) comprises (s) a sugar radical S * which represents a monosaccharide radical chosen from glucose, galactose, mannose, xylose, rhamnose, frustose, sorbose , N-acetylglucosamine, N-acetylgalactosamine, glucosamine, galactosamine, lactose, cellobiose, and maltose, preferably chosen from glucose, xylose, and rhamnose. 3. Method according to any one of claims 1 or 2 wherein the compound of formula (I) is chosen from the compounds of formulas (I '), (I ”), (!” ”), (A) , (l ”a), (l” ”a) and (l'b) following: (l'b) as well as their solvates such as hydrates, their optical, geometric isomers, tautomers and their base or acid salts, organic or inorganic, Formulas (I ’), (I”), (I ””), (a), (l ”a), (l” ”a) and (I'b) in which: - R is as defined above, preferably represents a group: i) hydroxy; this hydroxy can be in the alcoholate 0 form; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), sodium (Na ⁺ ), potassium ( K ⁺ ), magnesium (Mg ²⁺ ), calcium (Ca ²⁺ ), or ammonium; (when R is in alcoholate form, it forms with the carbonyl in the alpha position a carboxylate function COO; M ⁺ with M ⁺ as defined above) ii) (Ci-Cis) alkoxy; preferably C1-C4 alkoxy and more preferably ethoxy; iii) amino -NR’iR’2 with R’1 and R’2, independent of each other, representing: o for R’1: i) a hydrogen atom; ii) an (Ci-Cis) alkyl group, preferably (Ci-Ce) alkyl, preferably methyl; o for R’2: i) a hydrogen atom; ii) an (Ci-Cis) alkyl group; iii) a radical such as: O where: j = 0 or 1; R’4 represents a hydrogen atom or R’4 is chosen from the radicals (a1) to (a32) described below: (A2) Me ^ (a1) Me (a13) Me (a18) (a21) (a22) O (a23) (a24) (a25) Me OH (a27) (a28) (a29) (a30) (a31) Me (a32) R’4 can also form with R’1 and the nitrogen which carries R’1 a saturated heterocycle, of formula A1, or A2 or A3: R’6 designates i) a hydroxy radical -OH; ii) an alcoholate -O; M ⁺ with M ⁺ representing a cation such as zinc (Zn ²⁺ ), manganese (Mn ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ , Fe ³⁺ ), or an alkaline cation such as Na ⁺ , K ⁺ , or an alkaline earth cation such as Mg ²⁺ , Ca ²⁺ , or an ammonium cation; iii) a saturated or unsaturated (Ci-Ce) alkoxy radical; iv) a radical -NRfR _g with Rf and R _g , identical or different, representing a hydrogen atom, or a (Ci-Ce) alkyl group. And preferably R ^ represents a hydroxy radical, an alcoholate -O; M ⁺ , a saturated alkoxy (CiCe) radical, in particular methoxy or ethoxy, or an amino radical NH 2. or else R’1 and R’2 form with the nitrogen atom to which they are attached a heterocycloalkyl, optionally substituted such as piperazino, piperidino, or morpholino. - R ”is as defined above, preferably represents a hydrogen atom or an acetyl radical, and preferably a hydrogen atom; - R ’” represents a hydrogen atom, or a (Ci-Ce) alkyl group, or a group -CH2-OR "with R" as defined above in particular hydrogen or an acetyl radical, and preferably a hydrogen atom. Preferably R "represents a hydrogen atom, or a (Ci-C) alkyl group such as methyl, or a group -CH2OR" with R "denoting a hydrogen atom or an acetyl radical. 4. Method according to any one of claims 1, 2 or 3 in which the compound (s) of formula (I) is (are) chosen (s) from the following compounds, as well as its salts, isomers, solvates: compound S * = D-Glucose 1 O Chiral / ^ o I OH AoXV ⁰ compound S * = D-xylose 3 Chiral Me ° Χ ^ Χ ^{/ Ν Μ} θ 1 1 o ho 'γ' ^ 'ΌΗ OH compound S * = L-rhamnose 4 Chiral Me \ Me ,, - z ^N Me HO ^^ f OH ÔH compound S * = D-xylo-furanose 5 HO ^ P ..... HO OH ° ^^ '' X ^ -x 5. Compound of formula (I'b) as defined in claim 3 which is: compound S * = D-xylo-furanose 5 ..... HO OH ° ^^ '' X ^ -x 6. Use of compound (I) as defined in any one of claims 1 to 4 preferably at least one compound of formula (I) chosen from compounds 1 to 5 as defined in claim 4 as a whitening, lightening agent and / or depigmenting keratin materials, in particular the skin 7. Composition comprising, in a physiologically acceptable medium, at least one compound of formula (I) as defined in any one of claims 1 to 4, preferably at least one compound of formula (I) chosen from compounds 1 to 5 as defined in claim 4 8. Cosmetic treatment method according to any one of claims 1 to 4 for non-depigmentation, lightening and / or bleaching of keratin materials, in particular the skin of the face and / or the body, and / or prevention , reduction and / or treatment of an alteration in the complexion of the skin or the tint of the semi-mucous membranes comprising at least one step consisting in applying to the skin of the face and / or of the body at least one composition comprising at least a compound of formula (I) as defined according to any one of claims 1 to 5. 9. Process for the synthesis of the compounds of formula (I) as defined in claim 1 or 2 and of the compounds of formula (l'b) as defined in claim 3 and for which A denotes a hydrogen atom and the sugar is in furanose form according to the following diagram (2): Diagram (2) comprising the following stages: - step 1: reaction of a monosaccharide or a polysaccharide of formula (IV) with Meldrum acid (V), in particular in the presence of an organic base such as a tertiary amine such as triethylamine or tert -butylamine to lead to a lactone intermediate fused with a sugar motif in the form of furanose (VIII); 5 - step 2a: hydrolysis of the compound (VIII), in particular in an acid medium to lead to an acidic C-glycoside compound (II ¹ ) in furanose form or opening of the lactone (VIII) in an aqueous basic medium to lead to a compound C -acid glycoside (II ¹ ) in furanose form; step 2b: opening of the lactone compound (VIII) with an alcohol R _r -OH to lead to a compound C-glycoside ester (II ² ) in furanose form or opening of the lactone (VIII) with alcohol R _r - OH previously deprotonated with a strong base such as Na or NaH, to form the corresponding alcoholate; - step 2c: opening of the lactone compound (VIII) with an amine RriR ^ NH to lead to a compound C-glycoside amide (III ¹ ) in furanose form.