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WO2012080994A2 - Ester d'aminoacide n-acylé comme agent adoucissant - Google Patents

Ester d'aminoacide n-acylé comme agent adoucissant Download PDF

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Publication number
WO2012080994A2
WO2012080994A2 PCT/IB2011/055773 IB2011055773W WO2012080994A2 WO 2012080994 A2 WO2012080994 A2 WO 2012080994A2 IB 2011055773 W IB2011055773 W IB 2011055773W WO 2012080994 A2 WO2012080994 A2 WO 2012080994A2
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WO
WIPO (PCT)
Prior art keywords
skin
compound
scalp
cosmetic
composition
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Application number
PCT/IB2011/055773
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English (en)
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WO2012080994A3 (fr
Inventor
Francine Baldo
Original Assignee
L'oreal
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Publication date
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Publication of WO2012080994A2 publication Critical patent/WO2012080994A2/fr
Publication of WO2012080994A3 publication Critical patent/WO2012080994A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/004—Aftersun preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/75—Anti-irritant

Definitions

  • a subject-matter of the present invention is the cosmetic use of an N-acylated amino acid ester of formula (A) defined below as soothing agent.
  • the present invention also relates to an N-acylated amino acid ester of formula (A) defined below for the use thereof in a cosmetic composition.
  • a cosmetic composition can be intended in particular to prevent and/or treat at least one of the uncomfortable cutaneous reactions defined below.
  • the present invention also relates to an N-acylated amino acid ester of formula (A) defined below as dermatological agent for the prevention and/or treatment of skin disorders comprising an inflammatory component and to the use of such a compound in a dermatological composition intended to prevent and/or treat the skin disorders comprising an inflammatory component which are defined below.
  • the present invention relates to a nontherapeutic cosmetic method for soothing the skin and/or scalp, comprising at least one stage of application, to the skin and/or scalp, of a composition comprising at least one N-acylated amino acid ester of formula (A) defined below.
  • Cutaneous irritation or uncomfortable cutaneous reactions can be brought about by an exogenous stress, of chemical origin, for example xenobiotics, antigens, allergens, cosmetic products, compounds capable of provoking irritation of the skin, or peeling products; of environmental origin (temperature, climate, UV radiation, atmospheric pollution, in particular heavy metals, ozone, cigarette smoke, and the like) or of mechanical origin (rubbing actions, shearing actions, cleaning, and the like) , and by any stress of endogenous origin, such as disorders involving an inflammatory and/or hormonal mechanism affecting the skin, mucous membranes, scalp and/or hair.
  • an exogenous stress of chemical origin, for example xenobiotics, antigens, allergens, cosmetic products, compounds capable of provoking irritation of the skin, or peeling products
  • environmental origin temperature, climate, UV radiation, atmospheric pollution, in particular heavy metals, ozone, cigarette smoke, and the like
  • mechanical origin rubbing actions, shearing actions, cleaning, and the like
  • cosmetic compositions comprising, for example, keratoylitic and/or desquamating active principles for combating ageing and in particular exfoliating active principles and/or active principles which promote cell replacement, such as a-hydroxy acids (in particular lactic acid, glycolic acid or citric acid) , ⁇ -hydroxy acids (in particular salicylic acid) or retinoids (in particular retinoic acids, all-trans- or 13-cis-retinol, adapalene, and the like) .
  • active principles for combating ageing and in particular exfoliating active principles and/or active principles which promote cell replacement
  • active principles which promote cell replacement
  • a-hydroxy acids in particular lactic acid, glycolic acid or citric acid
  • ⁇ -hydroxy acids in particular salicylic acid
  • retinoids in particular retinoic acids, all-trans- or 13-cis-retinol, adapalene, and the like
  • a cosmetic or dermatological composition such as, for example, preservatives, surfactants, fragrances, solvents or propellants
  • the intensity or the seriousness of the cutaneous irritation discussed above may vary according to different criteria, such as skin and/or scalp which has been weakened and/or already damaged, reactive skin or skin affected by rosacea, indeed even irritable skin, and from the viewpoint of the degree of exogenous or endogenous stress.
  • the more or less high concentration of (a) susceptible compound (s) may provoke irritation of the skin and/or scalp or will have an impact on the intensity of the cutaneous irritation.
  • the present invention relates to cutaneous reactions which are expressed in the form of types of discomfort experienced on the skin and/or scalp by the user.
  • the discomfort can typically be red blotches, itching, feelings of heat and/or burning, tingling sensations, or tightness.
  • Cosmetic treatments make it possible to overcome these types of discomfort. These types of discomfort can be experienced after stress of mechanical or environmental origin, in particular after shaving the skin (beard, legs) , during a sudden fall in temperature, after a peeling operation, microabrasion or microdermabrasion, or also cleaning the skin and/or scalp.
  • the present invention relates to other visible skin signs which may also appear, or skin disorders, advantageously requiring this type of dermatological treatment.
  • Mention may in particularly be made, among these visible skin signs or skin disorders, of dry patches, oedema and/or pimples, inflammatory erythema, pruritus, psoriasis, cutaneous atopy, atopic dermatitis, urticaria, contact dermatitis, eczema, seborrhoeic dermatitis, acne and inflammatory hyperpigmentation or also irritable cutaneous reactions.
  • the physiological endogenous stress causing the skin disorders can, for example, be related to the abnormal production of proinflammatory mediators
  • cutaneous irritation employs a cascade of reactions which, by the recruitment of infiltrating blood cells (neutrophils, macrophages, and the like) and the substances which they release (cytokines, lymphokines, chemokines, and the like) , give rise to the persistent irritating process which is characterized mainly by irritation of the skin or involution of the hair bulb and its matrix environment when located on the scalp.
  • infiltrating blood cells neutrils, macrophages, and the like
  • cytokines, lymphokines, chemokines, and the like give rise to the persistent irritating process which is characterized mainly by irritation of the skin or involution of the hair bulb and its matrix environment when located on the scalp.
  • N-lauroylsarcosinate demonstrate properties which justify in particular the advantage thereof in incorporating them in soothing cosmetic compositions with the aim of preventing and/or treating uncomfortable cutaneous reactions, and in incorporating them in dermatological compositions with the aim of treating skin inflammation and/or irritation, on the other hand.
  • cosmetic care or dermatological treatment will be favoured according to the nature and the source of the cutaneous reaction.
  • N-acylated amino acid esters of formula (A) have already been taken advantage of as emollients in the formulation of cosmetic compositions intended for the care of the skin.
  • solubilizing agents for some molecules which easily crystallize, such as certain imidopercarboxylic acid derivatives, such as described in Application FR 0 852 018.
  • the present invention is targeted at protecting, according to a first aspect, the cosmetic use of a compound of formula (A) :
  • n is an integer equal to 0, 1 or 2
  • R' i represents a linear or branched C5 to C 21 alkyl or alkenyl radical
  • R' 2 represents a hydrogen atom or a Ci to C3 alkyl group
  • R' 3 represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group and a linear or branched C3 or C4 alkyl chain
  • R' 4 represents a linear or branched Ci to C 10 alkyl radical, a linear or branched C 2 to C 10 alkenyl radical or a sterol residue, and
  • the part -N (R' 2 ) CH (R' 3 ) (CH 2 ) n (CO) - is chosen from the following amino acids: valine, leucine, isoleucine, serine, threonine, proline, hydroxyproline, ⁇ -alanine, aminobutyric acid, aminocaproic acid, sarcosine or N-methyl- ⁇ -alanine,
  • the present invention is also targeted at protecting the cosmetic use of such a compound of formula (A) in accordance with the invention, the said compound being intended to prevent and/or treat uncomfortable cutaneous reactions of the skin and/or scalp.
  • These cutaneous reactions can be chosen in particular from red blotches, itching, feelings of heat and/or burning, tingling and tightness .
  • the compound of formula (A) in accordance with the invention can be employed in a cosmetic composition.
  • it can be employed in combination with at least one compound capable of provoking irritation of the skin and/or scalp .
  • the present invention is also targeted at protecting a nontherapeutic cosmetic method for soothing the skin and/or scalp, comprising at least one stage of application, to the skin and/or scalp, of a composition comprising at least one N-acylated amino acid ester of formula (A) in accordance with the invention.
  • the term "uncomfortable cutaneous reaction” is understood to mean all discomfort of the skin and/or scalp provoked by the types of stress brought to mind above and taking in particular the form of red blotches, itching, feelings of heat and/or burning, tingling or tightness.
  • These uncomfortable cutaneous reactions are advantageously induced by at least one condition chosen from the action of a peeling product, of microabrasion or microdermabrasion, of cleaning the skin and/or scalp, of shaving the skin, of temperature or of climate .
  • the present invention is also targeted at protecting, according to a second aspect, a compound of formula (A) in accordance with the invention as dermatological agent for the prevention and/or treatment of skin disorders comprising an inflammatory component.
  • the compound of formula (A) in accordance with the invention is more particularly of use in combating skin disorders chosen from dry patches, oedema and/or pimples, inflammatory erythema, pruritus, psoriasis, cutaneous atopy, atopic dermatitis, urticaria, contact dermatitis, eczema, seborrhoeic dermatitis, acne and inflammatory hyperpigmentation.
  • the compound of formula (A) in accordance with the invention can be employed in a dermatological composition.
  • it can be employed in combination with at least one compound capable of provoking irritation of the skin and/or scalp.
  • the present invention is furthermore targeted at a compound of formula (A) in accordance with the invention as antiirritant and/or antiinflammatory agent .
  • the present invention is targeted composition, in particular a dermatological composition, comprising a compound of formula (A) in accordance with the invention, intended to treat cutaneous irritation and/or inflammation, in particular of the skin and/or scalp.
  • cutaneous disorder comprising an inflammatory component is understood to mean all manifestations on the skin and/or scalp provoked by inflammatory and/or allergic reactions, whatever the source thereof, which may be given material form by the appearance of dry patches, oedema and/or pimples, inflammatory erythema, pruritus, psoriasis, cutaneous atopy, atopic dermatitis, urticaria, contact dermatitis, eczema, seborrhoeic dermatitis, acne and/or inflammatory hyperpigmentation.
  • compositions intended for irritable and/or allergic skin and/or mucous membranes and/or scalps agents capable of provoking irritation of the skin, such as cosmetic active principles (e.g.: keratolytic and/or desquamating agents) , dermatological active principles (e.g.: retinoids), some surfactants (preservatives, fragrances, solvents, propellants) and their mixtures, provided that the said cosmetic or dermatological compositions comprise at least one N-acylated amino acid ester of formula (A) , preferably isopropyl N-lauroylsarcosinate.
  • cosmetic active principles e.g.: keratolytic and/or desquamating agents
  • dermatological active principles e.g.: retinoids
  • some surfactants preservatives, fragrances, solvents, propellants
  • the said cosmetic or dermatological compositions comprise at least one N-acylated amino acid ester of formula (A) , preferably isopropyl N-lauroyl
  • irritable and/or allergic skin and/or mucous membranes and/or scalps is understood to mean, according to the invention, skin and/or mucous membranes and/or scalps which react to external attacks, sometimes in an exaggerated fashion.
  • Such skin and/or mucous membranes and/or scalps are then more subject to the development of a cutaneous reaction which may involve immunological or inflammatory mechanisms, in contrast to a cutaneous reaction involving mechanisms of neurogenic origin characterizing sensitive skin.
  • to prevent or “prevention” is understood to mean, according to the invention, the fact of reducing the risk of the occurrence or of slowing down the occurrence of a given phenomenon, namely, according to the first aspect of the present invention, the effect of discomfort generated by cutaneous reactions, such as red blotches, itching, feelings of burning, tingling and tightness, or skin disorders comprising an inflammatory component, such as set out above.
  • a composition in accordance with the invention can be a cosmetic or dermatological composition according to the application envisaged and thus comprises a physiologically acceptable medium.
  • physiologically acceptable medium is understood to mean a medium compatible with all keratinous substances, such as skin, scalp, nails, mucous membranes, eyes and hair, or any other cutaneous region of the body.
  • a physiologically acceptable medium is preferably a cosmetically or dermatologically acceptable medium, that is to say a medium without unpleasant odour, colour or appearance, which is fully compatible with the administration route under consideration.
  • the term “soothing agent” is understood to mean an agent which helps in reducing the discomfort of the skin and/or scalp, for example by soothing the feelings of itching or by toning down the red blotches, it being possible, for example, for this discomfort to be due to the dehydration thereof or to the application of a mechanical stress (shaving) .
  • N-acylated amino acid ester according to the present invention is advantageously chosen from the N-acylated amino acid esters of formula (A) as defined above .
  • the R'i(CO)- group is an acyl group of an acid preferably chosen from the group formed by capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, linoleic acid, linolenic acid, oleic acid, isostearic acid, 2-ethylhexanoic acid, coconut oil fatty acids and palm kernel oil fatty acids .
  • these fatty acids may exhibit a hydroxyl group .
  • the acid will be an acid chosen from the group formed by capric acid, lauric acid, myristic acid, palmitic acid, stearic acid and behenic acid .
  • It will preferably be lauric acid.
  • the -N (R' 2 ) CH (R' 3 ) (CH 2 ) n (CO) - part of the amino acid ester is chosen from the following amino acids: valine, leucine, isoleucine, serine, threonine, proline, hydroxyproline, ⁇ -alanine, aminobutyric acid, aminocaproic acid, sarcosine or N-methyl-p-alanine .
  • the part of the amino acid esters corresponding to the -OR' 4 group can be obtained from the alcohols chosen from the group formed by methanol, ethanol, propanol, isopropanol , butanol , tert-butanol, isobutanol ,
  • the alcohols will be chosen from the group formed by methanol, ethanol, propanol, isopropanol, butanol, tert-butanol, isobutanol, 3-methyl-l-butanol and 2-methyl-l-butanol, preferably formed by methanol, ethanol, propanol, isopropanol and butanol.
  • the alcohol will be isopropanol.
  • amino acid esters can be obtained in particular from natural sources of amino acids.
  • the amino acids originate from the hydrolysis of natural plant proteins (oats, wheat, soya, palm, coconut) and then necessarily result in mixtures of amino acids which will subsequently have to be esterified and then N-acylated.
  • the preparation of such amino acids is more particularly described in Patent Application FR 2 796 550, which is incorporated here by way of reference .
  • an N-acylated amino acid ester which is particularly suitable in the invention is of formula (A), in which:
  • the R'i(CO)- group is an acyl group of an acid chosen from the group formed by capric acid, lauric acid, myristic acid, palmitic acid, stearic acid and behenic acid, preferably lauric acid,
  • the part of the amino acid esters corresponding to the -OR' 4 group is obtained from the alcohols chosen from the group formed by methanol, ethanol, propanol, isopropanol and butanol, preferably isopropanol.
  • N-acylated amino acid ester more particularly preferred for the use thereof in the present invention is isopropyl N-lauroylsarcosinate of formula (B) :
  • CN 3 CH3 ( B ) such as the product sold under the trade name "Eldew SL-205" by Ajinomoto.
  • the N-acylated amino acid ester can be used in an amount sufficient to produce the desired effect, that is to say in an amount sufficient to sooth the skin and/or scalp or to prevent and/or treat irritation of the skin and/or scalp or an uncomfortable cutaneous reaction induced by any type of stress mentioned above, for example by a compound capable of inducing cutaneous irritation.
  • an N-acylated amino acid ester in accordance with the invention is employed in a content ranging from 0.1% to 25% by weight, preferably from 0.5% to 15% by weight, preferably from 1% to 10% by weight and very preferably from 1% to 5% by weight, with respect to the total weight of the cosmetic composition .
  • an N-acylated amino acid ester in accordance with the invention is employed in a content ranging from 0.1% to 30% by weight, preferably from 1% to 15% by weight, with respect to the total weight of the dermatological composition.
  • an N-acylated amino acid ester in accordance with the invention can be incorporated in a cosmetic composition intended to prevent and/or treat at least one of the uncomfortable cutaneous reactions defined above.
  • an N-acylated amino acid ester in accordance with the invention can be incorporated in a dermatological composition intended to prevent and/or treat at least one of the skin disorders defined above.
  • composition in accordance with the invention comprises a physiologically acceptable medium.
  • the physiologically acceptable medium can comprise water or organic solvents, such as Ci-Cs alcohol, in particular ethanol, isopropanol, tert-butanol or n-butanol; a polyol, such as glycerol; a glycol, such as butylene glycol, isoprene glycol, propylene glycol or polyethylene glycols, such as PEG-8; polyol ethers; acetone; or ethyl acetate.
  • organic solvents such as Ci-Cs alcohol, in particular ethanol, isopropanol, tert-butanol or n-butanol
  • a polyol such as glycerol
  • a glycol such as butylene glycol, isoprene glycol, propylene glycol or polyethylene glycols, such as PEG-8
  • polyol ethers such as acetone; or ethyl acetate.
  • composition according to the invention is preferably intended for topical use.
  • a composition in accordance with the invention can thus constitute a composition for the treatment or care of the skin (including the scalp) , keratinous fibres (hair, eyelashes, eyebrows) , nails or lips, or a sun- protection or artificial-tanning composition, or a product for cleaning or removing makeup from the skin, hair, eyebrows or eyelashes, a deodorant product or also a scenting product. It is then generally colourless or weakly coloured, and it can optionally comprise cosmetic or dermatological active principles. It can then be used as care base for the skin or lips (lip balms, which protect the lips from the cold and/or the sun and/or the wind) or as day or night care cream for the skin of the face and/or body. In addition, it can be provided in a form of a treating or nontreating and colouring or noncolouring shampoo and of a conditioning compound.
  • a composition in accordance with the invention can also constitute a coloured cosmetic composition and in particular a composition for making up the skin, keratinous fibres (hair or eyelashes) and/or mucous membranes, in particular a foundation, a blusher, a face powder, an eye shadow, a mascara, an eyeliner, a concealer compound in the form of a stick, an nail varnish, a lipstick or a lip gloss, optionally exhibiting care or treatment properties.
  • a composition in accordance with the invention can be provided in the formulation forms conventionally used for topical application and in particular in the form of dispersions of the lotion or serum type, of emulsions with a liquid or semiliquid consistency of the milk type, obtained by dispersion of a fatty phase in an aqueous phase (O/W) or vice versa (W/O), or of suspensions or emulsions with a soft, semisolid or solid consistency of the cream or gel type, or of multiple (W/O/W or 0/W/O) emulsions, of microemulsions , of vesicular dispersions of ionic and/or nonionic type, or of wax/aqueous phase dispersions.
  • These compositions are prepared according to the usual methods .
  • composition can also be provided in the form of a transdermal system which makes possible active or passive release of the active principle (s) by passage through the skin, for example of patch or gel patch (hydrogel) type.
  • the proportion of the oily phase of the emulsion can range, for example, from 5% to 80% by weight and preferably from 5% to 50% by weight, with respect to the total weight of the composition.
  • the oils, the emulsifiers and the coemulsifiers used in the composition in the form of an emulsion are chosen from those conventionally used in the cosmetics or dermatological field.
  • the emulsifier and coemulsifier generally present in a composition in accordance with the invention in a proportion ranging from 0.3% to 30% by weight and preferably from 0.5% to 20% by weight, with respect to the total weight of the composition.
  • the emulsion can comprise lipid vesicles.
  • oils for example, of hydrocarbon oils of vegetable origin, synthetic esters and ethers, silicone oils and their mixtures.
  • a compound of formula (A) in accordance with the invention also exhibits the advantage of preventing and/or treating cutaneous irritation or an uncomfortable cutaneous reaction which might have been provoked by a compound capable of provoking irritation of the skin and/or scalp, and also of making it possible to increase the amount of this compound having irritant nature in cosmetic or dermatological compositions in comparison with the normal amount used, for the purpose of an increase in effectiveness of these compounds.
  • an N-acylated amino acid ester in accordance with the invention can be incorporated in a cosmetic or dermatological composition which comprises a compound capable of provoking irritation of the skin and/or scalp .
  • the said N-acylated amino acid ester in accordance with the invention can be incorporated in a separate cosmetic or dermatological composition, according to the aspect of the invention as discussed above, intended to prevent and/or treat cutaneous irritation or an uncomfortable cutaneous reaction, which will be applied after and/or before the cosmetic and/or dermatological composition comprising the compound capable of provoking irritation of the skin and/or scalp, depending on whether it is desired to set in motion an inflammatory phase, which may be of use in said applications (vasodilation, depilation, and the like) or, on the contrary, to prevent it.
  • composition comprising the said peeling agent and then, in a second step, to apply a soothing composition comprising at least one N-acylated amino acid ester in accordance with the invention, the said at least one N-acylated amino acid ester in accordance with the invention being intended to reduce the discomfort reactions generated by the peeling and thus to sooth the skin and/or scalp.
  • an N-acylated amino acid ester in accordance with the invention is incorporated in a separate composition intended to be applied after the cosmetic or dermatological composition comprising at least one compound capable of provoking irritation of the skin and/or scalp.
  • an N-acylated amino acid ester in accordance with the invention is incorporated in a separate composition intended to be applied before the cosmetic or dermatological composition comprising at least one compound capable of provoking irritation of the skin and/or scalp.
  • cosmetic compounds or active principles dermatological compounds or active principles
  • surfactants in particular anionic surfactants
  • preservatives detergents
  • fragrances in particular scenting alcoholic solutions, solvents, propellants and their mixtures.
  • Mention may be made, among peeling agents specifically, of abrasive/exfoliating particles from natural or synthetic, organic or mineral sources. Mention may more particularly be made of pumice particles, silica particles, polyethylene beads, nylon beads and fruit kernel powders.
  • saturated monocarboxylic acids acetic acid
  • unsaturated monocarboxylic acids saturated and unsaturated dicarboxylic acids, saturated and unsaturated tricarboxylic acids
  • a-hydroxy acids and ⁇ -hydroxy acids of monocarboxylic acids a-hydroxy acids and ⁇ -hydroxy acids of dicarboxylic acids
  • a-hydroxy acids and ⁇ -hydroxy acids of tricarboxylic acids keto acids, a-keto acids, ⁇ -keto acids of polycarboxylic acids, of polyhydroxymonocarboxylic acids, of polyhydroxydicarboxylic acids and of polyhydroxytricarboxylic acids.
  • glycolic acid dioic acids, such as octadecenedioic acid or Arlatone Dioic DCA, sold by Uniqema
  • citric acid lactic acid, tartaric acid, malic acid or mandelic acid
  • esters such as the di (C 12 /C 1 3) alkyl tartrate or Cosmacol ETI, or the citrate triester of branched C 12 -13
  • those capable of acting on the enzymes involved in the desquamation or the decomposition of corneodesmosomes may also be capable of provoking irritation of the skin and/or scalp or an uncomfortable cutaneous reaction.
  • chelating agents with inorganic salts such as EDTA; N-acyl- ⁇ , ⁇ ' , ⁇ ' -ethylenediaminetriacetic acid; aminosulphonic compounds and in particular N- (2- hydroxyethyl ) piperazine-N' -2-ethanesulphonic acid (HEPES) ; 2-oxothiazolidine-4-carboxylic acid
  • procysteine derivatives of a-amino acids of glycine type (as described in EP 0 852 949, and the sodium methylglycinediacetate sold by BASF under the trade name Trilon M®) ; honey; or sugar derivatives, such as O-octanoyl-6-D-maltose, O-linoleyl- 6-D-glucose and N-acetylglucosamine .
  • Retinoids are also compounds capable of provoking irritation of the skin and/or scalp. Mention may be made, for example, among them, of retinol and its esters, retinal, retinoic acid and its derivatives, such as those described in the documents FR-A-2 570 377, EP-A-199 636, EP-A-325 540 and EP-A- 402 072, and adapalene.
  • the salts and derivatives, such as the cis or trans forms, the racemic mixtures and the dextrorotatory or laevorotatory forms of the compounds mentioned above are also regarded as compounds capable of provoking irritation of the skin and/or scalp.
  • vitamin D certain vitamins, such as vitamin D and its derivatives, such as vitamin D3, vitamin D2, calcitriol, calcipotriol , tacalcitol, 24,25-diOH- vitamin D3, 1-OH-vitamin D2 and 1 , 24-diOH-vitamin D2 ; or vitamin B9 and its derivatives,
  • agents for combating hair loss such as minoxidil and its derivatives, such as aminexil,
  • - hair dyes and colorants such as aminophenols and their derivatives, for example para- phenylenediamine (p-PDA) , N-phenyl-p-PDA, toluene- 2,5-diamine sulphate, meta-phenylenediamine (m-PDA) , toluene-3, 4-diamine and ortho-phenylenediamine (o-PDA) ,
  • p-PDA para- phenylenediamine
  • N-phenyl-p-PDA N-phenyl-p-PDA
  • toluene- 2,5-diamine sulphate meta-phenylenediamine
  • m-PDA meta-phenylenediamine
  • o-PDA 4-diamine and ortho-phenylenediamine
  • aluminium salts for example aluminium chlorohydrate
  • - depilatory and/or permanent-wave active principles such as thioglycolates or aqueous ammonia solution
  • - depigmenting agents e.g.: hydroquinone, vitamin C at a high concentration, kojic acid
  • agents for the treatment of greasy skin such as, for example, certain antibacterials , or benzoyl peroxide ,
  • propigmenting agents such as psoralens and methylangelicins
  • surfactants of anionic, cationic and amphoteric surfactants, more particularly anionic surfactants, such as alkyl sulphates and alkyl ether sulphates, for example lauryl sulphate and lauryl ether sulphate, and their salts, in particular sodium salts .
  • anionic surfactants such as alkyl sulphates and alkyl ether sulphates, for example lauryl sulphate and lauryl ether sulphate, and their salts, in particular sodium salts .
  • the compouind capable of provoking irritation of the skin and/or scalp is chosen from retinoids, -hydroxy acids, ⁇ -hydroxy acids, saturated and unsaturated dicarboxylic acids, such as octadecenedioic acid or Arlatone Dioic DCA, sold by Uniqema, anionic, cationic or amphoteric surfactants, 5- (n-octanoyl ) salicylic acid, antiperspirant active principles, such as aluminium salts, N- (2-hydroxyethyl) piperazine-N' -2- ethanesulphonic acid (HEPES) and cinnamic acid and their mixtures, and also desquamating agents, such as ketogulonic acid or glycolic acid.
  • retinoids such as octadecenedioic acid or Arlatone Dioic DCA, sold by Uniqema, anionic, cationic or amphoteric surfactants, 5- (n-octanoy
  • the compound capable of provoking irritation of the skin and/or scalp can be present in the composition in accordance with the present invention in an amount sufficient to provoke an irritation reaction of the skin and/or scalp.
  • it can be present in a content ranging from 0.0001% to 70% by weight, preferably from 0.01% to 50% by weight and better still from 0.1% to 30% by weight, with respect to the total weight of the composition.
  • N-acylated amino acid ester used according to the invention can also be combined with at least from 0.00001% to 95% by weight and preferably from 0.1% to 20% by weight of an antiinflammatory agent, a soothing agent or their mixture.
  • antiinflammatory agents of:
  • a steroidal antiinflammatory hydrocortisone, betamethasone, dexamethasone, and the like
  • nonsteroidal antiinflammatory such as aspirin or paracetamol
  • antagonist of inflammatory cytokines is understood to mean a compound capable of inhibiting the synthesis and/or the release of one or more inflammatory cytokines.
  • the definition of an antagonist of inflammatory cytokines also includes compounds which inhibit or block the binding of these cytokines to their receptor (s) .
  • the antiinflammatory agent is chosen from algal extracts capable of modulating the production of cytokines by keratinocytes, such as Phycosaccharide®, sold by Codif, the aqueous/glycolic extract of the alga Laminaria saccharina, in particular Phlorogine®, sold by Secma, Aloe vera extracts, the extract of the bark and roots of Terminalia sericea or Sericoside 3058500, sold by Indena, or peptide derivatives, such as Skinasensyl® from Cognis LS .
  • algal extracts capable of modulating the production of cytokines by keratinocytes such as Phycosaccharide®, sold by Codif, the aqueous/glycolic extract of the alga Laminaria saccharina, in particular Phlorogine®, sold by Secma, Aloe vera extracts, the extract of the bark and roots of Terminalia sericea or Sericoside 3058500
  • the antiinflammatory agents are preferably present in the compositions in accordance with the invention at a concentration which can vary from 0.00001% to 10% by weight approximately, with respect to the total weight of the composition. More preferably, the concentration of antiinflammatory compound can vary between 0.0005% to 2% by weight, with respect to the total weight of the composition.
  • xanthine derivatives such as diethylaminoethyltheophylline hydrochloride ;
  • waters and extracts for example aqueous, aqueous/ alcoholic or aqueous/glycolic extracts
  • flowers and plants such as cornflower water, camomile water, mint water, lime water, rose water, Rosaceae (e.g.: Rosa gallica) extracts, peony extracts, hawthorn extracts, yarrow extracts, mallow extracts, marigold extracts, sweet clover extracts, sage extracts, elderberry water, Ginkgo biloba extracts, arnica extracts, oregano extracts, green tea extracts, waterlily flower extracts, iris extracts, birch bark extracts or Aloe vera extracts;
  • Rosaceae e.g.: Rosa gallica
  • peony extracts peony extracts
  • hawthorn extracts yarrow extracts
  • mallow extracts marigold extracts
  • sweet clover extracts sage extracts
  • elderberry water Ginkgo biloba extracts
  • fruit extracts such as pineapple extract, papaya extract or guava extract
  • algae in particular of the Laminaria type (for example, red or brown algae) , such as the extract of brown alga Padina pavonica, for example HPS 3 Padina Pavonica, sold by Alban Muller;
  • pyrrolidonecarboxylates and in particular zinc pyrrolidonecarboxylate (Zn-PCA) or copper pyrrolidonecarboxylate (Cu-PCA) ;
  • oils of vegetable origin such as canola seed oil and shea butter oil
  • essential oils for example of coriander, of balm, of lavender, of mint or of camomile, and their mixtures; acexamic acid and tranexamic acid (trans-4- ( aminomethyl) cyclohexanecarboxylic acid) ;
  • ursolic acid and the extracts comprising it such as rosemary leaf extract
  • polysaccharides comprising fucose such as Fucogel 1000, sold by Solabia (aqueous solution comprising 1% by dry weight of polysaccharide comprising fucose, galactose and galacturonic acid) ; electrolytes and in particular an aqueous mixture comprising from 30% to 35% of magnesium chloride, from 20% to 28% of potassium chloride, from 3% to 10% of sodium chloride, from 0.2% to 1% of calcium chloride, from 0.1% to 0.6% of magnesium bromide and from 0.1% to 0.5% of insoluble materials, the said mixture being referred here to as "Dead Sea bath salts" as it corresponds to the main salts present in the Dead Sea;
  • galactolipids for example resulting from oats, such as, for example, digalactosyl diglyceride or monogalactosyl diglyceride;
  • amino acids, their derivatives and their salts such as the sodium salt of amino acids grafted to cocoyl chains, sold in the form of a mixture under the name Sepicalm S by Seppic, capryloylglycine, sold under the name Lipacide C8G by Seppic, and the mixture of capryloylglycine, of cinnamon and of sarcosine sold under the name Sepicontrol A5 by Seppic;
  • TNF-a antagonists such as lisofylline, A802715, sulfasalazine, CDP-571 (anti-TNF-a) antibody or MDL-201112;
  • substance P antagonists such as sendide, spantide II, the peptides described in Application EP-A-680749 and the filamentous bacterium extracts described in Application EP-A-761204;
  • CGRP antagonists such as CGRP 8-37, anti-CGRP antibodies or plant extracts having a CGRP-antagonist activity (e.g.: Iris pallida) .
  • divalent strontium, zinc, manganese, magnesium or calcium salts such as those described in the documents WO-A-96/19184, WO-A-96/19182 and WO-A-96/19228;
  • the soothing agent can advantageously be chosen from allantoin, ⁇ -glycyrrhetinic acid, the extracts comprising it, such as, for example, the extract of Glycyrrhiza glabra (liquorice) , and the complexes comprising it, such as the allantoin/glycyrrhetinic acid complex; lyophilized or nonlyophilized plankton, the extracts thereof and the complexes thereof; waters and extracts of flowers and plants: camomile water, lime water, rose water or birch extracts; bisabolol; essential oils, for example of coriander; algae, in particular of the Laminaria type (for example, red or brown algae) , such as the extract of brown alga Padina pavonica , for example HPS 3 Padina Pavonica, sold by Alban Muller; acexamic acid and tranexamic acid (trans-4- (aminomethyl) cyclohexane- carboxylic
  • the compounds are, as the case may be, cited by their chemical names or by their CTFA names (International Cosmetic Ingredient Dictionary and Handbook) .
  • CTFA names International Cosmetic Ingredient Dictionary and Handbook
  • the test consists in evaluating the effects of Eldew SL-205 on the response of the surface epidermal cells to an irritant agent, such as PMA (phorbol myristate acetate) . This is because PMA stimulates the secretion of IL-8 and PGE2.
  • PMA phorbol myristate acetate
  • NCTC human keratinocytes (NCTC-2544) are cultured in 96-well plates for 24 hours. These cells are subsequently treated (or not, in the case of the controls) with Eldew SL-205 and incubated for 24 hours at 37°C and 5% C0 2 .
  • the cells are again treated (or not, in the case of the controls) with medium comprising the irritation inductor (PMA 0.1 yg/ml) and then again left to incubate for 24 hours.
  • PMA 0.1 yg/ml the irritation inductor
  • the PMA strongly stimulated the secretion both of the IL-8 (108.3 yg/ml) and of PGE2 (384.5 ng/ml) .
  • the Eldew was tested, in the presence of PMA, at concentrations of 0.00002%, 0.0002% and 0.002%.
  • Table 1 Assaying of IL-8 and PGE2 secreted by the NCTC cells stimulated by PMA
  • the Eldew significantly inhibits, and in a concentration dependent way, the secretion of IL-8 and PGE2, without any cytotoxic effect being observed.
  • compositions in accordance with the invention comprising in particular Eldew SL 205, were prepared in a conventional way. They are expanded upon below.
  • Example 2 Compositions
  • Phenylethylbenzenediol 0.50 Xanthan gum 0.20

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  • Veterinary Medicine (AREA)
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Abstract

La présente invention concerne l'utilisation cosmétique d'un ester d'aminoacide N-acylé comme agent adoucissant. La présente invention concerne également un ester d'aminoacide N-acylé comme agent dermatologique, comprenant un composant anti-inflammatoire, pour la prévention et/ou le traitement de troubles de la peau, tels que les dartres, les œdèmes et/ou les boutons, les érythèmes inflammatoires, le prurit, le psoriasis, l'atopie cutanée, la dermatite atopique, l'urticaire, la dermatite de contact, l'eczéma, la dermatite séborrhéique, l'acné et l'hyperpigmentation inflammatoire.
PCT/IB2011/055773 2010-12-17 2011-12-19 Ester d'aminoacide n-acylé comme agent adoucissant WO2012080994A2 (fr)

Applications Claiming Priority (4)

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FR1060738A FR2968952A1 (fr) 2010-12-17 2010-12-17 Ester d'acide amine n-acyle a titre d'agent apaisant
FR1060738 2010-12-17
US201161436205P 2011-01-26 2011-01-26
US61/436,205 2011-01-26

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WO2012080994A3 WO2012080994A3 (fr) 2013-06-27

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2988600A1 (fr) * 2012-03-30 2013-10-04 Oreal Composition a effet matifiant comprenant un ester d'acide amine n-acyle
CN108289810A (zh) * 2015-12-10 2018-07-17 莱雅公司 包含羟基化二苯基甲烷衍生物的组合物

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EP0199636A1 (fr) 1985-04-11 1986-10-29 CENTRE INTERNATIONAL DE RECHERCHES DERMATOLOGIQUES C.I.R.D. Groupement d'Intérêt Economique dit: Dérivés benzonaphtaléniques, leur procédé de préparation et leur application dans les domaines pharmaceutique et cosmétique
EP0319028A1 (fr) 1987-12-04 1989-06-07 L'oreal Association de dérivés de 1, 8-hydroxy et/ou acyloxy anthracène ou anthrone et de dérivés de pyrimidine pour induire et stimuler la croissance des cheveux et diminuer leur chute
EP0325540A1 (fr) 1988-01-20 1989-07-26 Centre International De Recherches Dermatologiques Galderma - Cird Galderma Esters et thioesters aromatiques, leur procédé de préparation et leur utilisation en médecine humaine ou vétérinaire et en cosmétique
EP0402072A2 (fr) 1989-06-05 1990-12-12 Sequa Chemicals Inc. Liant pour fibres non tissées
EP0680749A2 (fr) 1994-05-05 1995-11-08 L'oreal Utilisation d'un antagoniste de substance P dans une composition cosmétique et composition obtenue
WO1996019184A1 (fr) 1994-12-21 1996-06-27 Cosmederm Technologies Formulations et procedes pour diminuer l'irritation de la peau
WO1996019228A1 (fr) 1994-12-21 1996-06-27 Cosmederm Technologies Formulations et procedes pour diminuer l'irritation de la peau
WO1996019182A1 (fr) 1994-12-21 1996-06-27 Cosmederm Technologies Formulations et procedes pour diminuer l'irritation de la peau
EP0761204A1 (fr) 1995-09-07 1997-03-12 L'oreal Utilisation d'un extrait d'une bactérie filamenteuse non photosynthétique et composition le contenant
EP0852949A2 (fr) 1997-03-31 1998-07-15 Shiseido Company Limited Utilisation des alpha-aminoacides pour favoriser la dégradation des desmosomes ou la desquamation du stratum corneum
FR2796550A1 (fr) 1999-07-21 2001-01-26 Asepta Lab Preparations et applications d'esters de n-acylaminoacides

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Publication number Priority date Publication date Assignee Title
FR852018A (fr) 1939-03-23 1940-01-22 Billards excentriques
FR2570377A1 (fr) 1984-09-19 1986-03-21 Cird Derives heterocycliques aromatiques et leur application dans les domaines therapeutique et cosmetique
EP0199636A1 (fr) 1985-04-11 1986-10-29 CENTRE INTERNATIONAL DE RECHERCHES DERMATOLOGIQUES C.I.R.D. Groupement d'Intérêt Economique dit: Dérivés benzonaphtaléniques, leur procédé de préparation et leur application dans les domaines pharmaceutique et cosmétique
EP0319028A1 (fr) 1987-12-04 1989-06-07 L'oreal Association de dérivés de 1, 8-hydroxy et/ou acyloxy anthracène ou anthrone et de dérivés de pyrimidine pour induire et stimuler la croissance des cheveux et diminuer leur chute
EP0325540A1 (fr) 1988-01-20 1989-07-26 Centre International De Recherches Dermatologiques Galderma - Cird Galderma Esters et thioesters aromatiques, leur procédé de préparation et leur utilisation en médecine humaine ou vétérinaire et en cosmétique
EP0402072A2 (fr) 1989-06-05 1990-12-12 Sequa Chemicals Inc. Liant pour fibres non tissées
EP0680749A2 (fr) 1994-05-05 1995-11-08 L'oreal Utilisation d'un antagoniste de substance P dans une composition cosmétique et composition obtenue
WO1996019184A1 (fr) 1994-12-21 1996-06-27 Cosmederm Technologies Formulations et procedes pour diminuer l'irritation de la peau
WO1996019228A1 (fr) 1994-12-21 1996-06-27 Cosmederm Technologies Formulations et procedes pour diminuer l'irritation de la peau
WO1996019182A1 (fr) 1994-12-21 1996-06-27 Cosmederm Technologies Formulations et procedes pour diminuer l'irritation de la peau
EP0761204A1 (fr) 1995-09-07 1997-03-12 L'oreal Utilisation d'un extrait d'une bactérie filamenteuse non photosynthétique et composition le contenant
EP0852949A2 (fr) 1997-03-31 1998-07-15 Shiseido Company Limited Utilisation des alpha-aminoacides pour favoriser la dégradation des desmosomes ou la desquamation du stratum corneum
FR2796550A1 (fr) 1999-07-21 2001-01-26 Asepta Lab Preparations et applications d'esters de n-acylaminoacides

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2988600A1 (fr) * 2012-03-30 2013-10-04 Oreal Composition a effet matifiant comprenant un ester d'acide amine n-acyle
CN108289810A (zh) * 2015-12-10 2018-07-17 莱雅公司 包含羟基化二苯基甲烷衍生物的组合物
EP3386469A4 (fr) * 2015-12-10 2019-05-01 L'oreal Composition comprenant des dérivés hydroxylés du diphénylméthane
US12121604B2 (en) 2015-12-10 2024-10-22 L'oreal Composition comprising hydroxylated diphenylmethane derivatives

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