WO2019129823A1

WO2019129823A1 - Use of fucose derivatives as deodorants

Info

Publication number: WO2019129823A1
Application number: PCT/EP2018/097041
Authority: WO
Inventors: Maria Dalko; Ségolène ADAM DE BEAUMAIS; Audrey Gueniche
Original assignee: L'oreal
Priority date: 2017-12-29
Filing date: 2018-12-27
Publication date: 2019-07-04
Also published as: FR3076216A1; FR3076216B1

Abstract

The present invention relates to the use of at least one compound of formula (I) below: (I) R1 denotes i) a monosaccharide radical; ii) an oligosaccharide radical; iii) a cycloalkyl radical substituted with at least one substituent OR; or iv) a C1-C6 alkyl radical comprising at least one substituent OR; R is a hydrogen atom or a protective group for hydroxyl functions; and also the solvates thereof and the optical and/or geometric isomers thereof, including enantiomers and diastereoisomers, and the racemates thereof, alone or as a mixture, for treating body odor, in particular unpleasant armpit odor. The present invention also relates to a deodorant and/or antiperspirant topical composition comprising, as deodorant active agent, at least one compound of formula (I) as defined above and at least one additional deodorant active agent other than the compounds of formula (I) and/or at least one antiperspirant active agent.

Description

USE OF FUCOSE DERIVATIVES AS DEODORANTS

The present invention relates to the use of fucose derivatives as deodorants.

The present invention also relates to a method for treating body odor, in particular armpit odor, using at least one fucose derivative. The present invention also relates to a cosmetic composition containing at least one fucose derivative and an antiperspirant and/or an additional deodorant active agent, and also to the use of such compounds for treating body odor, in particular armpit odor.

In the cosmetics field, it is well known to use, by topical application, deodorant products containing active substances of deodorant type and/or of antiperspirant type for reducing or even eliminating body odor. This body odor, in particular armpit odor, is generally unpleasant.

Deodorant active agents thus have the function of reducing or preventing the formation of these unpleasant odors.

Moreover, antiperspirant substances have the effect of limiting the flow of sweat, and are generally constituted of aluminum salts.

Deodorant substances generally destroy the resident bacterial flora. Among these substances, the ones most commonly used are triclosan (2,4,4'-trichloro-2'- hydroxydiphenyl ether) and famesol, which have the drawback of substantially modifying the ecology of the flora of the skin. There are also substances that reduce bacterial growth. Among these substances, mention may be made of transition-metal-chelating agents such as EDTA or DPTA. These materials deprive the medium of the metals necessary for bacterial growth.

The destruction of the resident bacterial flora can promote the multiplication of opportunistic bacteria capable of causing an infection, a fortiori on areas from which the hair has been removed, such as the armpits. Furthermore, certain bacteria present in the natural flora of the skin, such as Staphylococcus epidermidis, are known to have a beneficial effect on the skin by contributing in particular to their regeneration (Seminars in Immunology 2013, 25, 370- 377, Sci. Transl. Med. 2017, 9, 1-11).

There is thus a need to identify new deodorant active agents that can be integrated into a topical cosmetic formulation making it possible to treat unpleasant body odor, in particular associated with human perspiration, and in particular armpit odor, but which are, moreover, such that they do not totally eradicate the bacterial micro flora of the skin, in particular the armpit bacterial microflora.

The object of the present invention is especially to meet these needs.

The aim of the present invention is to provide derivatives which make it possible to treat unpleasant body odor associated with human perspiration, such as armpit odor.

One of the aims of the present invention is also to provide derivatives which have a deodorant activity, for reducing odors, in particular in human beings, and more particularly for combating body odor, such as armpit odor, especially in the form of compositions, in particular topical compositions. Fucose derivatives, derived in particular from maternal milk, are known, as in WO

2012/158517, as prebiotic agents which promote the intestinal microbial flora. These prebiotic agents are administered in oral compositions in order to promote probiotic bacterial growth in the face of pathogenic microorganisms. Similarly, it is known practice to apply compositions comprising fucose derivatives for preventing and treating bacterial and fungal infections of the skin and of the mucus membranes of the sex organs in EP 2 815 757. Moreover, these same fucose derivatives are used according to EP 2 656 862 in disposable absorbent items, in particular in diapers, for preventing skin disorders, such as skin irritation, caused by the diaper rubbing against the skin. Finally, it is known practice, in EP 3 067 040 to use mixtures of monosaccharides and oligosaccharides such as fucosyllactose for countering the aging process, and in particular skin aging.

On the other hand, to the knowledge of the inventors, it has never been proposed to use fucose derivatives for the purpose of acting against body odor. The inventors have discovered, surprisingly, that compounds of formula (I) detailed hereinafter, alone or as a mixture, exhibit good deodorant efficiency and can be easily formulated in a product intended to reduce body odor, and in particular armpit odor, alone or optionally in combination with antiperspirants and/or conventional additional deodorant active agents, other than the compounds of the invention, without the drawbacks mentioned above.

The compounds of formula (I) according to the invention advantageously have a deodorant activity, making it possible to treat unpleasant body odor associated with human perspiration, such as armpit odor. Thus, according to a first subject, a subject of the invention is the use of at least one compound of formula (I) as defined below, and also the solvates thereof and the optical and/or geometric isomers thereof, including enantiomers and diastereoisomers, and the racemates thereof, alone or as a mixture, for treating body odor, in particular unpleasant armpit odor. A subject of the present invention is also the use of at least one compound of formula

(I) as defined below, and also the solvates thereof and the optical and/or geometric isomers thereof, including enantiomers and diastereoisomers, and the racemates thereof, alone or as a mixture, as a deodorant for treating body odor, preferably armpit odor.

A subject of the invention is also a process for cosmetic and non-therapeutic treatment of keratin materials for combating body odor, characterized in that it comprises at least one step of topical application of at least one compound of formula (I) as defined below and also the solvates thereof and the optical and/or geometric isomers thereof, including enantiomers and diastereoisomers, and the racemates thereof, alone or as a mixture, or of a composition containing same, in particular under the armpits. A subject of the invention is also a topical, preferably cosmetic, in particular deodorant and where appropriate antiperspirant, composition comprising, as deodorant active agent, at least one compound of formula (I) and also the solvates thereof and the optical and/or geometric isomers thereof, including enantiomers and diastereoisomers, and the racemates thereof, alone or as a mixture, and at least one additional deodorant active agent other than the compounds of formula (I) and/or at least one antiperspirant active agent.

Against all expectations, the inventors have discovered that the fucose derivatives of formula (I) according to the invention have good efficiency against unpleasant body odor, and in particular against armpit odor. Indeed, and as has been demonstrated in the examples hereinafter, the compounds of formula (I) according to the invention make it possible to reduce the power and intensity of the bad odor caused by sweat.

The compounds of formula (I) according to the invention also have the advantage that they do not irritate the skin nor do they interfere with the sweat flow. Furthermore, the inventors have noted, unexpectedly, that these compounds of formula (I) make it possible to preserve the cutaneous bacterial microflora of the keratin materials to which they are applied, in particular the bacterial micro flora of the armpits. As such, the compounds of formula (I) according to the invention do not have antimicrobial, and in particular antibacterial, properties against the cutaneous bacterial microflora of the keratin materials, in particular of the armpits.

What is more, given their natural product specificity, the derivatives of formula (I) are, as opposed to the conventional deodorant active agents, in accordance with consumer expectations.

Furthermore, as emerges from the examples hereinafter, the compounds of formula (I) prove to be compatible with other deodorant active agents and/or antiperspirant active agents which are conventional, and their respective efficiencies are not impaired. What is more, the presence of the compounds according to the invention in combination with these conventional active agents makes it possible to obtain an efficiency that is at least as high.

COMPOUNDS OF FORMULA (11 The invention thus describes at least one compound of formula (I) as a deodorant active agent in the form of a composition, preferably a topical composition, and also the use of such a compound of formula (I) for treating unpleasant body odor especially associated with perspiration, and in particular armpit odor, alone or in combination with an additional deodorant compound and/or an antiperspirant active agent.

Said compounds correspond to formula (I) below:

in which

- Ri denotes

i) an optionally aminated and/or methylated monosaccharide radical;

ii) an optionally aminated and/or methylated oligosaccharide radical, preferably an oligosaccharide radical comprising between 2 and 5 monosaccharides, such as an optionally aminated and/or methylated disaccharide radical;

iii) a cycloalkyl radical substituted with at least one substituent OR; or

iv) a Ci-C₆ alkyl radical comprising at least one substituent OR;

- R is a hydrogen atom or a protective group for hydroxyl functions, in particular an acetyl radical or a benzyl radical;

and also the solvates thereof and the optical and/or geometric isomers thereof, including enantiomers and diastereoisomers, and the racemates thereof, alone or in a mixture.

According to one particular embodiment of the invention, the compound of formula (I) is in the stereochemical configuration below:

For the purposes of the present invention, unless otherwise indicated, an “ oligosaccharide” denotes a polysaccharide sugar which is a polymer constituted of several optionally aminated and/or methylated monosaccharides, typically from 2 to 10, or even from 2 to 5, which are linked to one another by O-saccharide bonds, said polymers being constituted of optionally aminated and/or methylated monosaccharide units, said monosaccharide units comprising at least 5 carbon atoms, preferably 6, the monosaccharide units being in particular linked to one another by a (alpha) or b (beta) anomeric 1,4 or 1,6 linkage, it being possible for each saccharide unit to be in the L or D, preferably L, configuration and to be in the form of solvates such as hydrates.

They are more particularly polymers formed from a certain number of monosaccharides having the general formula: -[C_x(l¾0)_y)]_n- with x being an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is between 5 and 7 inclusive, preferably x = 6, and y an integer which represents x-l, and n is an integer greater than or equal to 2, particularly between 2 and 5 inclusive, more particularly n = 2, and more preferentially“ oligosaccharide radical” denotes a lactose radical or else a disaccharide radical comprising a glucose unit and a galactose unit or else a disaccharide radical comprising two glucose units, it being possible for each glucose or galactose unit to be optionally aminated and/or methylated.

For the purposes of the present invention, unless otherwise indicated, an“ optionally aminated monosaccharide or oligosaccharide radical” is intended to mean that said radical is optionally substituted with one or more amino group(s) NRaRb, i.e. that, optionally, at least one of the hydroxyl groups of at least one saccharide unit is replaced with an NRaRb group, with Ra and Rb, which may be identical or different, representing i) a hydrogen atom, ii) an aryl(Ci-C₄)alkyl group such as benzyl, iii) a radical -C(Y)-(Y')p- R’a with Y and Y’, which may be identical or different, representing an oxygen or sulfur atom or -N(R'b)-, preferably oxygen, p = 0 or 1, preferably 0; and R'a and R'b represent i) or ii) of Ra and Rb defined above, and in particular R'a denoting a (Ci-C₆)alkyl group such as methyl. In other words, at least one saccharide unit is deoxylated on at least one position of said unit. For the purposes of the present invention, unless otherwise indicated, an“ optionally methylated monosaccharide or oligosaccharide radical” is intended to mean that at least one of the hydroxyl groups for at least one saccharide unit is substituted with a methyl. In other words, at least one of the hydroxyl groups thus becomes an -OCH₃. Typically, a 1- methylglucose group may be used, in the context of the present invention, as a monosaccharide radical.

Preferably, Ra and Rb represent a hydrogen atom or a (Ci-C₄)alkylcarbonyl group, in particular an acetyl.

Preferably, the monosaccharide or oligosaccharide radical is linked to the rest of the molecule by a bond between the Ci carbon atom of one of the sugars of said monosaccharide or polysaccharide radical, this bond possibly being a or b anomeric.

The term“ protective group for the hydroxyl function” is known by those skilled in the art, in particular in the two books“Protective Groups in Organic Synthesis”, T. W. Greene, John Willey & Sons ed., NY, 1981, pp.193-217; and“Protecting Groups”, P. Kocienski, Thieme, 3rd ed., 2005.

In particular, the protective group for the hydroxyl function is chosen from:

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

- (di)aryl(Ci-C₄)alkyl or triaryl(Ci-C₄)alkyl which is optionally substituted, such as 9- anthracenylmethyl, phenylmethyl(benzyl), diphenylmethyl or triphenylmethyl optionally substituted with one or more groups in particular chosen from halogen, (Ci-C₄)alkyl, (Ci- C₄)alkoxy, such as methoxy, hydroxyl, (Ci-C₄)alkylcarbonyl, (di)(Ci-C₄)(alkyl)amino such as dimethylamino; preferably benzyl;

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

- ReRfRgSi- with Re, Rf, and Rg, which may be identical or different, representing a (Ci- C₆)alkyl group, an optionally substituted aryl group, an optionally substituted (di)aryl(Ci-

C₄)alkyl group, an optionally substituted triaryl(Ci-C₄)alkyl group, such as benzyl, in particular chosen from trimethylsilyl or TMS, triethylsilyl, isopropyldimethylsilyl, tert- butyldimethylsilyl or TBDMS, (triphenylmethyl)dimethylsilyl, t-butyldiphenylsilyl, methyldiisopropylsilyl, methyl(di-t-butyl)silyl, tribenzylsilyl, tri-p-xylylsilyl, triisopropylsilyl, triphenylsilyl;

- or else two contiguous hydroxyl groups can be protected with an alkylene group *- C(Rl)(Rm)-(C(Rk)(Rj))q-* as drawn below:

with Rj, Rk, Rl, and Rm, which may be identical or different, representing a hydrogen atom or a (Ci-C₄)alkyl, (poly)halo(Ci-C₄)alkyl, optionally substituted aryl such as phenyl, aryl(Ci-C₄)alkyl such as benzyl, (poly)halo(Ci-C₄)alkoxy, (Ci-C₄)alkoxy, halogen, (di)(Ci- C₄)(alkyl)amino or hydroxyl group, or else two Rj and Rk and/or Rl, and Rm groups form, together with the carbon atom which bears them, an oxo group or a (hetero)cycloalkyl such as cyclohexyl or cyclopropyl; q is 0, 1, 2 or 3, preferably *-C(Rl)(Rm)-(C(Rk)(Rj))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 ethoxymethy lene .

More particularly, the protective group for the hydroxyl function is chosen from acetyl or benzyl.

For the purposes of the present invention and unless otherwise indicated:

- the expression“alkyl” denotes a linear or branched radical containing from 1 to 6 carbon atoms, in particular from 1 to 4 carbon atoms, for example methyl, ethyl, n-propyl, isopropyl, butyl, n-pentyl, n-hexyl;

- the term“( Cx-Cy) alkyl” denotes an alkyl radical as defined previously, said alkyl radical comprising x to y carbon atoms; - the expression“ cycloalkyl” denotes a 5- to lO-membered monocyclic or bicyclic, preferably monocyclic, fused or non-fused hydrocarbon-based group which is saturated or contains one or more ethylenic unsaturations, which is non-aromatic, this cycloalkyl possibly being substituted with one or more radicals, which may be identical or different, chosen from alkyl, hydroxyalkyl and alkoxy radicals. Preferentially, according to the present invention, the cycloalkyl is saturated and comprises from 5 to 8 ring members, in particular 5 or 6 and more preferentially is chosen from cyclopentyl and cyclohexyl;

- the expression“a/ least one” is equivalent to“one or more” and can in particular denote from 1 to 8, in particular from 1 to 6, especially from 1 to 5, or even from 1 to 3; - the expression " inclusive " for a range of concentrations means that the limits of the range are included in the defined interval;

- the expression“ isomer” denotes the optical isomers, the geometric isomers and also the tautomers of the compounds of formula (I); and

- the expression“ solvate” denotes the various forms that a compound of formula (I) can take depending on the solvent which contains it, by interacting with the molecules of this solvent so as to form interactions of ion-dipole type, hydrogen bonds or van der Waals bonds; the acceptable solvates of the compounds used in the present invention comprise conventional solvates such as those formed during the final 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.

It is understood that, for the compounds of formula (I) as defined above, when Ri represents a monosaccharide radical, it may be in pyranose form (the sugar heterocycle which forms it is 6-membered) or furanose form (the sugar heterocycle which forms it is 5- membered).

When Ri represents an oligosaccharide radical, it preferentially comprises the sequence of 2 to 5 identical or different saccharide units which may be in furanose or pyranose form. In the context of the present invention, the monosaccharide may be a galactose, a glucosamine, a glucose, a 2-acetamidoglucose or a l-methyl-2-acetamidoglucose.

In the context of the present invention, the oligosaccharide may be a disaccharide which results from the linking of a saccharide unit in furanose form and of a unit in pyranose form or the linking of a saccharide unit in pyranose form and of a unit in furanose form or else from the linking of two saccharide units in pyranose form, such as lactose, as a disaccharide radical comprising a glucose unit and a galactose unit or else as a disaccharide radical comprising two glucose units, it being possible for each glucose or galactose unit to optionally be aminated and/or methylated as described above. Whether it is a monosaccharide or oligosaccharide radical, each saccharide unit may be in the levorotatory L form or the dextrorotatory D form, and in a or b anomeric form.

In the context of the invention, unless otherwise mentioned, the term“ skin” is intended to mean human skin, for example facial or body skin, in particular the skin of the hands, the feet, the armpits or the scalp. In the context of the invention, the term“ body odor” is intended to mean for example armpit odor or foot odor.

According to one particular embodiment of the invention, R denotes a hydrogen atom, an acetyl radical or a benzeyl radical, preferably a hydrogen atom.

According to one particular embodiment, Ri denotes an optionally aminated and/or methylated monosaccharide radical as defined above, in particular chosen from an optionally aminated and/or methylated glucose, glucosamine, galactose and galactosamine radical, and even more particularly from an N-acetylglucosamine (or 2-acetamidoglucose ou 2-acetamido-2-deoxyglucose) radical, a galactose radical and a l-methyl-N- acetylglucosamine (or l-methyl-2-acetamidoglucose or l-methyl-2-aectamido-2- deoxyglucose) radical.

According to another embodiment of the invention, Ri denotes an optionally aminated and/or methylated, preferably aminated, monosaccharide radical, more preferentially an N-acetylglucosamine radical, more preferentially an N-acetyl-D- glucosamine radical, a(l 3)-linked to the rest of the molecule of formula (I).

According to one particular embodiment, Ri denotes an optionally aminated and/or methylated oligosaccharide radical as defined above, preferably an optionally aminated and/or methylated oligosaccharide radical comprising between 2 and 5 monosaccharides, in particular a disaccharide comprising optionally aminated and/or methylated galactose and/or optionally aminated and/or methylated glucose, said disaccharide preferably being optionally aminated lactose, a disaccharide comprising a galactose and a glucose which are independently optionally aminated and/or methylated or a disaccharide comprising two glucoses which are independently optionally aminated and/or methylated, even more preferably being lactose.

According to another embodiment of the invention, Ri denotes a disaccharide radical, preferably lactose (D-galactopyranosyl-P(l 4)D-glucopyranose) a(l 2)-linked to the rest of the molecule of formula (I). According to one preferred embodiment of the invention, the compounds of formula

(I) are chosen from the compounds (a) to (g) below and also the solvates thereof and the optical and/or geometric isomers thereof, including enantiomers and diastereoisomers, and the racemates thereof, alone or in a mixture:

According to one particularly preferred embodiment, the compound of formula (I) is 2'-0-fucosyllactose of formula (a) (or Fuc-a- 1 ,2-Gal-P- 1 ,4-Glc) and also the solvates thereof

Compounds of formula (I) according to the invention are currently available on the market, in particular under the names 2-O-fucosyllactose, 2’-fucosyllactose, 2’-a-L- fucosyllactose or 3’-0- a-L-fucosyllactose.

A compound according to the invention may be used in a cosmetic composition. Such a cosmetic composition may comprise a content of compound of formula (I) as defined above, ranging from 0.1% to 20% by weight, better still ranging from 0.2% to 15% by weight, even better still ranging from 0.5% to 10% by weight, relative to the total weight of the composition. According to a particular embodiment, a cosmetic composition according to the invention may comprise a content of compound of formula (I) ranging from 0.6% to 5% by weight, preferably from 0.7% to 1% by weight relative to the total weight of the composition.

DEODORANT AND/OR ANTIPERSPIRANT ACTIVE AGENTS

A subject of the invention is a composition comprising at least one compound of formula (I) and at least one additional deodorant active agent distinct from a compound of formula (I) and/or at least one antiperspirant.

In particular, a composition according to the invention comprises a content of additional deodorant active agent and/or of antiperspirant active agents that may range from 0.001% to 30% by weight, preferably that may range from 0.01% to 20% by weight, better still that may range from 0.02% to 15% by weight, relative to the total weight of the composition.

Thus, according to one embodiment variant, the composition according to the invention contains one or more additional deodorant active agents other than the compounds of formula (I) according to the invention. The term " deodorant active agent " refers to any substance that is capable of masking, absorbing, improving and/or reducing the unpleasant odor resulting from the decomposition of human sweat by bacteria.

These additional deodorant active agents may be chosen for example from:

- water-soluble zinc salts, for instance zinc pyrrolidonecarboxylate (more commonly known as zinc pidolate), zinc sulfate, zinc chloride, zinc lactate, zinc gluconate and zinc phenolsulfonate;

- bacteriostatic agents or bactericidal agents, such as 2,4,4'-trichloro-2'- hydroxydiphenyl ether (Triclosan), 2,4-dichloro-2'-hydroxydiphenyl ether, 3',4',5'- trichlorosalicylanilide, l-(3',4'-dichlorophenyl)-3-(4'-chlorophenyl)urea (Triclocarban) or 3,7,1 l-trimethyldodeca-2,5,l0-trienol (Famesol);

- quaternary ammonium salts such as cetyltrimethylammonium salts or cetylpyridinium salts;

- chlorhexidine and the salts;

- diglyceryl monocaprate, diglyceryl monolaurate, glyceryl monolaurate; and

- polyhexamethylene biguanide salts.

Generally, these additional deodorant active agents are advantageously present in an amount which is lower than that considered when they are formulated as a single deodorant active agent in a deodorant composition. This reduction may be of about from 1% to 20%.

A composition according to the invention may comprise a content of additional deodorant active agents that may range from 0.01% to 50.0% by weight, and preferably in an amount that may range from 0.1% to 30.0% by weight, relative to the total weight of the composition.

According to another embodiment variant, a composition according to the invention contains at least one or more antiperspirant active agents.

The term "antiperspirant active agent " is intended to mean a compound which, by itself, has the effect of reducing the flow of sweat, of reducing the sensation on the skin of moisture associated with human sweat or of masking human sweat.

These antiperspirant active agents are preferably chosen from aluminum and/or zirconium salts; complexes of zirconium hydroxychloride and of aluminum hydroxychloride with an amino acid, such as those described in patent US-3792068, commonly known as“ZAG complexes”. Such complexes are generally known under the name ZAG (when the amino acid is glycine). ZAG complexes ordinarily have an Al/Zr quotient ranging from about 1.67 to 12.5 and a mctal/Cl quotient ranging from about 0.73 to 1.93. Among these products, mention may be made of aluminum zirconium octachlorohydrex GLY, aluminum zirconium pentachlorohydrex GLY, aluminum zirconium tetrachlorohydrate GLY and aluminum zirconium trichlorohydrate GLY.

Among the aluminum salts that may be mentioned are aluminum chlorohydrate, aluminum chlorohydrex, aluminum chlorohydrex PEG, aluminum chlorohydrex PG, aluminum dichlorohydrate, aluminum dichlorohydrex PEG, aluminum dichlorohydrex PG, aluminum sesquichlorohydrate, aluminum sesquichlorohydrex PEG, aluminum sesquichlorohydrex PG, alum salts, aluminum sulfate, aluminum zirconium octachlorohydrate, aluminum zirconium pentachlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium trichlorohydrate and more particularly the aluminum hydroxy chloride sold by the company Reheis under the name Reach 301 or by the company Guilini Chemie under the name Aloxicoll PF 40. Aluminum and zirconium salts are, for example, the salt sold by the company Reheis under the name Reach AZP- 908-SUF.

According to one preferred embodiment of the invention, the composition comprises at least one antiperspirant active agent, in particular chosen from aluminum salts and/or zirconium salts. In particular, the antiperspirant active agents according to the invention can be chosen from aluminum chloride hexahydrate, aluminum chlorhydroxide or mixtures thereof.

A composition according to the invention may comprise a content of antiperspirant active agents that may range from 0.001% to 50% by weight, preferably that may range from 0.1% to 30% by weight, better still that may range from 0.1% to 20% by weight, relative to the total weight of the composition.

According to one particular embodiment of the invention, the compound(s) of formula (I)/additional deodorant and/or antiperspirant active agent(s) weight ratio ranges from 0.001 to 10, better still ranges from 0.01 to 5.0, even better still ranges from 0.02 to 1.0.

Of course, according to another variant, a composition according to the invention may also comprise the compound(s) of formula (I) as active agent and one or more other compounds in particular as defined below. COMPOSITIONS

The compositions according to the invention may be in any galenical form conventionally used for topical application and especially in the form of aqueous gels, or aqueous or aqueous-alcoholic solutions. By adding a fatty or oily phase, they may also be in the form of dispersions of lotion type, emulsions of liquid or semi-liquid consistency of milk type, obtained by dispersing a fatty phase in an aqueous phase (O/W) or vice versa (W/O), or suspensions or emulsions of soft, semi-solid or solid consistency of the cream or gel type, or alternatively multiple emulsions (W/O/W or O/W/O), microemulsions, vesicular dispersions of ionic and/or nonionic type, or wax/aqueous phase dispersions. The composition according to the invention is formulated in a physiologically acceptable medium. The term“ physiologically acceptable medium” is understood to mean a medium that is compatible with human keratin materials, in the case in point the skin. The physiologically acceptable medium is preferentially a cosmetically or dermatologically acceptable medium, i.e. a medium that has no unpleasant odor, color or appearance, and that does not cause the user any unacceptable discomfort or tautness.

These compositions are prepared according to the usual methods known to those skilled in the art.

A composition according to the invention may comprise at least one aqueous phase, or it may be anhydrous. In the context of the invention, the term " anhydrous composition " is intended to mean a composition containing less than 2% by weight of water, or even less than 0.5% of water, and especially free of water, the water not being added during the preparation of the composition but corresponding to the residual water provided by the mixed ingredients.

According to another particular form of the invention, the compositions according to the invention may be solid, in particular in wand or stick form.

In the context of the invention, the term " solid composition " is intended to mean that the measurement of the maximum force measured by texturometry during the penetration of a probe into the sample of formulation must be at least equal to 0.25 newton, in particular at least equal to 0.30 newton and especially at least equal to 0.35 newton, assessed under precise measurement conditions as follows.

The formulations are poured hot into jars 4 cm in diameter and 3 cm deep. Cooling is performed at ambient temperature. The hardness of the formulations produced is measured after an interval of 24 hours. The jars containing the samples are characterized in texturometry using a texturometer such as the machine sold by the company Rheo TA- XT2, according to the following protocol: a stainless-steel ball probe 5 mm in diameter is brought into contact with the sample at a speed of 1 mm/s. The measurement system detects the interface with the sample, with a detection threshold equal to 0.005 newton. The probe penetrates 0.3 mm into the sample, at a speed of 0.1 mm/s. The measuring machine records the change in force measured in compression over time, during the penetration phase. The hardness of the sample corresponds to the average of the maximum force values detected during penetration, over at least three measurements.

Aqueous phase According to another advantageous variant, the composition comprises at least one aqueous phase. The aqueous phase content in the composition may be between 0% and 98.0% by weight, relative to the total weight of the composition.

The compositions according to the invention may comprise at least one aqueous phase. They are especially formulated as aqueous lotions or as water-in-oil or oil-in-water emulsions or multiple emulsions (oil-in-water-in-oil or water-in-oil-in-water emulsions) (such emulsions are known and described for example by C. Fox in“Cosmetics and Toiletries” - November 1986 - Vol 101 - pages 101-112).

The aqueous phase of said compositions may contain water and generally other water-soluble or water-miscible solvents. The water-soluble or water-miscible solvents may comprise short-chain, for example Ci-C₄, monoalcohols such as ethanol or isopropanol; diols or polyols, for instance ethylene glycol, 1 ,2-propylene glycol, 1,3- butylene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, le 2- ethoxyethanol, diethylene glycol mo no methyl ether, triethylene glycol mo no methyl ether and sorbitol. More particularly, propylene glycol, glycerol and propane- 1 ,3-diol will be used.

When the composition is in emulsion form, it generally contains, depending on the nature of the emulsion, one or more emulsifying surfactants. The total amount of emulsifiers will preferably be included in a content of active material ranging from 1% to 8% by weight and more particularly from 2% to 6% by weight relative to the total weight of the composition.

Fatty phase

The compositions according to the invention may contain at least one water- immiscible organic liquid phase, known as a fatty phase. This phase generally comprises one or more hydrophobic compounds which render said phase water-immiscible. Said phase is liquid (in the absence of structuring agent) at ambient temperature (20-25°C). Preferentially, the water-immiscible organic liquid phase in accordance with the invention generally comprises at least one volatile oil and/or nonvolatile oil and optionally at least one structuring agent.

The term“ /7” is intended to mean a fatty substance that is liquid at ambient temperature (25°C) and atmospheric pressure (760 mmHg, i.e. l.05xl0⁵ Pa). The oil may be volatile or nonvolatile.

For the purposes of the invention, the term " volatile oil " is intended to mean an oil that is capable of evaporating on contact with the skin in less than one hour, at ambient temperature and atmospheric pressure. The volatile oils of the invention are volatile cosmetic oils which are liquid at ambient temperature, having a non-zero vapor pressure, at ambient temperature and atmospheric pressure, ranging in particular from 0.13 Pa to 40 000 Pa (10³ to 300 mmHg), in particular ranging from 1.3 Pa to 13 000 Pa (0.01 to 100 mmHg) and more particularly ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mmHg).

The term“ nonvolatile oil” is intended to mean an oil that remains on the skin at ambient temperature and atmospheric pressure for at least several hours, and that especially has a vapor pressure of less than 10 ³ mmHg (0.13 Pa). The oil may be chosen from any physiologically acceptable oil and in particular cosmetically acceptable oil, especially mineral, animal, plant or synthetic oils; in particular volatile or nonvolatile hydrocarbon-based oils and/or silicone oils and/or fluoro oils, and mixtures thereof. More precisely, the term“ hydrocarbon-based oil” is intended to mean an oil mainly comprising carbon and hydrogen atoms and optionally one or more functions chosen from hydroxyl, ester, ether and carboxylic functions. Generally, the oil has a viscosity of from 0.5 to 100 000 mPa.s, preferably from 50 to 50 000 mPa.s and more preferably from 100 to 300 000 mPa.s. As examples of volatile oils that may be used in the invention, mention may be made of:

- volatile hydrocarbon-based oils chosen from hydrocarbon-based oils containing from 8 to 16 carbon atoms, and especially CVCV, isoalkanes of petroleum origin (also known as isoparaffins), for instance isododecane (also known as 2, 2, 4,4,6- pentamethylheptane), isodecane and isohexadecane, for example the oils sold under the trade names Isopar or Permethyl, branched CVCV, esters and isohexyl neopentanoate, and mixtures thereof.

- volatile silicones, for instance linear or cyclic volatile silicone oils, especially those with a viscosity of < 8 centistokes (8 x l0 ⁶ m²/s), and especially having from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms, and mixtures thereof.

As volatile silicone oils that may be used in the invention, mention may be made especially of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane and dodecamethylpentasiloxane, and mixtures thereof.

As examples of nonvolatile oils that may be used in the invention, mention may be made of: hydrocarbon-based plant oils such as liquid triglycerides of fatty acids having 4 to 24 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or else wheatgerm oil, olive oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, alfalfa oil, poppy oil, pumpkin oil, marrow oil, blackcurrant oil, sunflower oil, com oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit Nobel, jojoba oil; linear or branched hydrocarbons, of mineral or synthetic origin, such as liquid paraffins and derivatives thereof, petroleum jelly, polydecenes, polybutenes, hydrogenated polyisobutene such as Parleam, or squalane; synthetic ethers containing from 10 to 40 carbon atoms, such as dipentyl ether; synthetic esters, especially of fatty acids such as the oils of formula R'C’OOR² in which R¹ represents a linear or branched higher fatty acid residue comprising from 1 to 40 carbon atoms and R² represents a hydrocarbon-based chain, which is especially branched, containing from 1 to 40 carbon atoms with R¹ + R² > 10, for instance isononyl isononanoate, isopropyl myristate, isopropyl palmitate or Ci₂ to Ci₅ alkyl benzoate, fatty alcohols that are liquid at ambient temperature, with a branched and/or unsaturated carbon-based chain having from 12 to 26 carbon atoms, such as octyldodecanol; silicone oils, for instance nonvolatile linear polydimethylsiloxanes (PDMSs) (dimethicones) or cyclic polydimethylsiloxanes (PDMSs) (cyclomethicones); polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, which are pendant or at the end of a silicone chain, these groups containing from 2 to 24 carbon atoms; phenyl silicones, for instance phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenyl siloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes and 2- phenylethyl trimethylsiloxy silicates, and mixtures thereof.

According to one particular embodiment, the composition according to the invention comprises at least one fatty phase. Thus, the fatty phase content in the composition may be between 0% and 98.0% by weight, relative to the total weight of the composition. The composition according to the invention may also contain one or more additional compounds, such as active agents, preservatives, antioxidants, complexing agents, fragrances, colorants, natural extracts, lightening agents, vitamins, urea, caffeine, depigmenting agents, beta-hydroxy acids such as salicylic acid and derivatives thereof, alpha- hydroxy acids such as lactic acid and glycolic acid, emollients and humectants, such as ethoxylated methyl glucosides and ethoxylated acylated methyl glucosides, organic and inorganic screening agents, or mixtures thereof.

It may also contain a water-dispersible agent, such as clays, polymers, pigments, aluminum oxides, silicates, talc, magnesium silicates, titanium dioxide, zinc oxide or mixtures thereof. The compositions according to the invention may optionally be packaged in an aerosol and may be in the roll-on, stick, aerosol or spray form.

The pharmaceutical formula is of course suitable for the packaging mode selected.

In the case of a stick, a solid formulation is preferred. In the case of roll-ons, aerosols and sprays, lipophilic formulae are preferred. For example, the compositions in the form of vaporizable fluid lotions are applied to the skin in the form of fine particles by means of pressurizing devices.

Throughout the description, including the claims, the expression "comprising a" should be understood as being synonymous with " comprising at least one", unless otherwise specified. The expressions " between ... and..." and "ranging from... to..." should be understood as being inclusive of the limits, unless otherwise specified. In the description and the examples below, the percentages are percentages by weight, unless otherwise indicated. The percentages are thus given by weight relative to the total weight of the composition. The ingredients are mixed in the order and under conditions that are readily determined by those skilled in the art.

APPLICATION EXAMPLES

A) Study of anti-odor effects (on incubated sweat)

The deodorant activity of the compounds according to the invention was evaluated in the ex- vivo olfactory evaluation test, on incubated sweat. The compound used according to the invention is 2'-0-fucosyllactose (CAS:

41263-94-9) which is sold by Carbosynth under the reference OF06739 or compound of formula (a) as defined above. This compound was evaluated in a pool of fresh sweat.

The samples were prepared in 10 ml screw-top headspace vials; they were incubated at 35°C for 24 h with stirring. A sample of sweat with 1 mg of anhydrous aluminum hydroxychloride (ACH) in 1 ml of sweat (i.e. 0.1% corresponding to 0.1 g/lOO ml) is incubated so as to serve as a positive reference (with a smell that is not very unpleasant) and a sample of sweat alone is incubated so as to serve as a negative reference (with an unpleasant smell).

The samples, after incubation, are subject to a blind olfactory evaluation by a panel of six individuals on the headspace vials. The incubated samples of sweat containing ACH and of sweat alone are evaluated at the same time so as to serve respectively as negative and positive references.

Two parameters are evaluated:

reduction of the sweat odor intensity (% relative to the sweat alone control), - overall power of the odor with 0 for not very powerful and 10 for very powerful. Table I below gives the results of the evaluations carried out by a panel of 6 individuals. The values in the table correspond to the mean of the values obtained for the 6 panelists.

Table I:

Conclusion

A significant decrease (p=0,045) in the unpleasant smell, both in terms of intensity and in terms of power of the odor, is noted with 2'-0-fucosyllactose compared with the negative reference, which is incubated sweat alone.

B) Formulations

The following formulations were prepared according to the invention: Aqueous formulation 1 :

Formulation 1 produces a deodorant effect. Aqueous formulation 2:

Formulation 2 produces a deodorant effect.

The 2'-0-fucosyllactose compound in accordance with the invention is thus compatible with aqueous formulations comprising skin-friendly water-soluble or water- dispersible active agents.

Aqueous formulation 3 :

Formulation 3 produces a deodorant and antiperspirant effect. Aqueous formulation 4:

Formulation 4 produces a deodorant and antiperspirant effect.

The 2'-0-fucosyllactose compound according to the invention is also compatible with formulae comprising other deodorant and/or antiperspirant active agents.

Claims

1. The use of at least one compound of formula (I) below:

in which

- Ri denotes

i) an optionally aminated and/or methylated monosaccharide radical;

iii) a cycloalkyl radical substituted with at least one substituent OR; or

iv) a Ci-C₆ alkyl radical comprising at least one substituent OR;

and also the solvates thereof and the optical and/or geometric isomers thereof, including enantiomers and diastereoisomers, and the racemates thereof, alone or in a mixture, for treating body odor, in particular unpleasant armpit odor.

2. The use as claimed in claim 1, characterized in that Ri denotes an optionally aminated and/or methylated monosaccharide radical, in particular chosen from an optionally aminated and/or methylated glucose, glucosamine, galactose and galactosamine radical.

3. The use as claimed in the preceding claim, characterized in that Ri denotes a monosaccharide radical chosen from an N-acetylglucosamine, a galactose radical and a l-methyl-N-acetyglucosamine radical, in particular an N-acetylglucosamine radical, more preferentially an N-acetyl-D-glucosamine radical a(l 3)-linked to the rest of the molecule of formula (I).

4. The use as claimed in claim 1, characterized in that Ri denotes an optionally aminated and/or methylated oligosaccharide radical, preferably an optionally aminated and/or methylated oligosaccharide radical comprising between 2 and 5 monosaccharides, in particular a disaccharide.

5. The use as claimed in either one of claims 1 and 4, characterized in that Ri denotes a disaccharide comprising optionally aminated and/or methylated galactose and/or optionally aminated and/or methylated glucose, said disaccharide preferably being optionally aminated lactose, a disaccharide comprising a galactose and a glucose which are independently optionally aminated and/or methylated or a disaccharide comprising two glucoses which are independently optionally aminated and/or methylated, even more preferably being lactose.

6. The use as claimed in claim 1 or 5, characterized in that Ri denotes a disaccharide radical, preferably lactose (D-galactopyranosyl-P(l 4)D-glucopyranose) a(l 2)-linked to the rest of the molecule of formula (I).

7. The use as claimed in claim 1, characterized in that the compound of formula (I) is chosen from 2'-fucosyllactose, 2-acetamido-2-deoxy-3-0-(a-L- fucopyranosyl)-D-glucopyranose, 3-fucosyllactose, methyl-2-acetamido-4-0-(2- acetamido-2-deoxy-P-D-glucopyranosyl)-2-deoxy-6-0-(a-L-fucopyranosyl)-P-D- glucopyranoside, 2-0-(a-L-fucopyranosyl)-D-galactopyranose, methyl-2-acetamido-2- deoxy-3-0-(a-L-fucopyranosyl)-P-D-glucopyranoside and methyl-2-acetamido-2-deoxy-3- 0-(a-L-fucopyranosyl)-4-0-(P-D-galactopyranosyl)-P-D-glucopyranoside, and also the solvates thereof and the optical and/or geometric isomers thereof, including enantiomers and diastereoisomers, and the racemates thereof, alone or as a mixture.

8. The use claimed in the preceding claim, characterized in that the compound of formula (I) is 2’-0-fucosyllactose and also the solvates thereof.

9. The use as claimed in any one of the preceding claims, characterized in that the compound of formula (I), and also the solvates thereof and the optical and/or geometric isomers thereof, including enantiomers and diastereoisomers, and the racemates thereof, alone or as a mixture, is (are) used in a cosmetic composition in a content ranging from

0.1% to 20% by weight, better still ranging from 0.2% to 15% by weight, even better still ranging from 0.5% to 10% by weight, relative to the total weight of the composition.

10. A topical, preferably cosmetic, in particular deodorant and where appropriate antiperspirant, composition comprising, as deodorant active agent, at least one compound of formula (I) as defined in any one of claims 1 to 8, and also the solvates thereof and the optical and/or geometric isomers thereof, including enantiomers and diastereoisomers, and the racemates thereof, alone or as a mixture, and at least one additional deodorant active agent other than the compounds of formula (I) and/or at least one antiperspirant active agent.

11. The composition as claimed in claim 10, characterized in that the composition comprises a content of compound(s) of formula (I) ranging from 0.1% to 20% by weight, better still ranging from 0.2% to 15% by weight, even better still ranging from 0.5% to 10% by weight, relative to the total weight of the composition.

12. The competition as claimed in either one of claims 10 and 11, characterized in that the compound(s) of formula (I)/additional deodorant active agent(s) and/or antiperspirant active agent(s) weight ratio ranges from 0.001 to 10, better still ranges from 0.01 to 5, even better still ranges from 0.02 to 1.0.

13. The composition as claimed in any one of claims 10 to 12, characterized in that it comprises at least one antiperspirant active agent, in particular chosen from aluminum and/or zirconium salts, and in particular from aluminum chloride hexahydrate, aluminum chlorhydroxide and mixtures thereof.