EP1001739A1 - Use of a 2-amino-alkane polyol as agent for treating skin ageing signs - Google Patents
Use of a 2-amino-alkane polyol as agent for treating skin ageing signsInfo
- Publication number
- EP1001739A1 EP1001739A1 EP98941554A EP98941554A EP1001739A1 EP 1001739 A1 EP1001739 A1 EP 1001739A1 EP 98941554 A EP98941554 A EP 98941554A EP 98941554 A EP98941554 A EP 98941554A EP 1001739 A1 EP1001739 A1 EP 1001739A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- use according
- octadecane
- diol
- skin
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
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- 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
- A61Q19/08—Anti-ageing preparations
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- 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
- A61K8/41—Amines
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- 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
- A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
Definitions
- the present invention relates to the use, as active principle in a cosmetic composition or for the preparation of a pharmaceutical composition, of an effective amount of at least one 2-amino-alkane-1, 3-diol, or of one of its derivatives, intended for treating the signs of skin aging as well as a non-therapeutic method for treating skin aging.
- Skin aging resulting from effects on the skin of intrinsic or extrinsic factors, is manifested by the appearance of fine lines and wrinkles, by the yellowing of the skin which develops a parchment appearance accompanied by the appearance of pigment spots, by the disorganization of the elastin and collagen fibers leading to a loss of elasticity, flexibility and firmness and by the appearance of telangiectasias.
- Some of these signs of aging are more particularly linked to intrinsic or physiological aging, that is to say to “normal” aging linked to age, while others are more specific to extrinsic aging, ie that is to say aging generally caused by the environment; this is more particularly photo-aging due to exposure to the sun, light or any other radiation.
- the invention is concerned with intrinsic or physiological aging as well as extrinsic aging.
- the skin changes resulting from intrinsic or physiological aging are the consequence of genetically programmed senescence in which endogenous factors intervene. This intrinsic aging notably causes a slowing down of the renewal of skin cells. Histologically the skin is generally thinned, both epidermally and dermally. The density of the fibrous macromolecules of the dermis (elastin and collagen) is reduced.
- extrinsic aging leads to clinical alterations such as thick wrinkles and the formation of soft and / or tanned skin, and histopathological changes such as an excessive accumulation of elastic material in the upper dermis and degeneration of the fibers. collagen.
- US Pat. No. 4,603,146 describes the use of retinoic acid and its derivatives in cosmetic compositions, with a view to combating skin aging.
- numerous patents and publications see for example application EP-A-413 528) as well as many commercial cosmetic compositions teach the use of ⁇ -hydroxy acids such as lactic acid, glycolic acid or else citric acid to treat skin aging.
- beta-hydroxy acids and more particularly salicylic acid and its derivatives are known for their flaking properties (see documents WO-A-93/10756 and US-A-4 767 750).
- the subject of the invention is therefore the use of a 2-amino-alkane polyol of formula (I) (below), or of one of its derivatives, in a cosmetic or dermatological composition for topical application, intended to treat certain signs of endogenous and / or exogenous aging.
- This treatment can be carried out as a preventive and / or curative measure.
- the N-acylated derivatives based on sphinganine [(2S, 3R) -2-amino-1, 3-octadecanediol] are ceramides predominantly present in the hair, while analogous derivatives based on phytosphingosine [(2S , 3S, 4R) -2-amino-1, 3,4-octadecane-triol), other ceramides, are part of the lipids mainly present in the stratum corneum of the skin.
- Ceramides are used in cosmetics in natural or synthetic form in compositions intended for example to reinforce the barrier effect of the stratum corneum in order to reduce the loss of water and therefore the drying of the skin (GB 2 178 312, GB 2 213 723 , EP 227 994, EP 282 616, EP 556 957).
- compositions for their properties giving the skin better elasticity EP 500 437) or in compositions for hair use to strengthen the hair and / or repair the damage caused by the continual assaults that this one undergoes.
- the invention relates to the use in a cosmetic composition or for the preparation of a pharmaceutical composition intended for treating the signs of skin aging, of at least one compound of general formula (I):
- R- represents a linear or branched hydrocarbon radical, optionally hydroxylated, saturated or unsaturated, having 4 to 28 carbon atoms
- R2 represents a hydrogen atom or the radical
- R3 represents a linear or branched, saturated or unsaturated hydrocarbon-based radical having from 1 to 11 carbon atoms or a linear or branched, hydroxylated, saturated or unsaturated hydrocarbon-based radical having from 1 to 29 carbon atoms, the hydroxyl being capable of be esterified by an acyl chain having from 2 to 30 carbon atoms, linear or branched, saturated or unsaturated;
- X represents a hydrogen atom or the OH radical; or at least one of its optical isomers or one of the diastereoisomers.
- R-1 preferably contains from 6 to 22 carbon atoms and even more preferably from 10 to 18 carbon atoms.
- R2 represents H or a radical
- O and R3 represents a linear or branched, saturated or unsaturated hydrocarbon radical having from 1 to 9 carbon atoms or a linear or branched, hydroxylated, saturated or unsaturated hydrocarbon radical, having from 1 to 21 carbon atoms.
- Ri represents a saturated and / or linear hydrocarbon radical, more particularly a saturated linear hydrocarbon radical.
- R- represents a saturated hydrocarbon radical having 14 carbon atoms, and even more preferably R ⁇ represents a linear, saturated hydrocarbon radical having 14 carbon atoms.
- the agent promoting the care and / or prevention of aging can be a mixture of compounds of formula (I), for which R, and / or R 2 are chains of different lengths.
- 2-N-acetylamino-octadecane-1, 3-diol or 2-N-octanoylamino-octadecane-1, 3-diol is used.
- a subject of the invention is therefore the use of a 2-amino-alkane-1, 3-diol of formula (I) (below), or of one of its derivatives, in a cosmetic or dermatological composition for topical application, intended to treat wrinkles and / or fine lines and / or yellowing of the skin and / or the parchment appearance of the skin and / or pigmented spots of the skin and / or telangiectasias and or loss elasticity, flexibility and / or firmness of the skin.
- the amount of compounds of formula (I) which can be used according to the invention depends, of course, on the nature of the compound used, on its physicochemical properties and on its mode of application. A person skilled in the art knows how to adjust the amount of compound of formula (I) to be used as required.
- the compounds of formula (I) can be used at concentrations by weight of between 10 ⁇ % and 20%, and preferably between 10 "3 % and 10% in the composition.
- the composition may take the form in particular of an aqueous, alcoholic, hydroalcoholic or oily solution or of dispersion of the lotion or serum type, of an emulsion of liquid or semi-liquid consistency of the milk type, obtained by dispersing a fatty phase in an aqueous phase (O / W) or vice versa (W / O), or a suspension or an emulsion of soft consistency of the cream, foam or aqueous or anhydrous gel type, or still microcapsules or microparticles, or a vesicular dispersion of the ionic and / or nonionic type. It can also take the form of an aerosol composition also comprising a pressurized propellant.
- this composition is prepared according to the usual methods.
- the amounts of the various constituents of the composition according to the invention are those conventionally used in the fields considered.
- the proportion of the fatty phase can range from 5% to 80% by weight, and preferably from 5% to 50% by weight relative to the total weight of the composition.
- the oils, waxes, emulsifiers and co-emulsifiers used in the composition in the form of an emulsion are chosen from those conventionally used in the cosmetic field.
- the emulsifier and the co-emulsifier are present in the composition in a proportion ranging from 0.3% to 30% by weight, and preferably from 0.5 to 20% by weight relative to the total weight of the composition .
- the emulsion may, in addition, contain lipid vesicles.
- the fatty phase can represent more than 90% of the total weight of the composition.
- composition comprising at least one compound of formula (I) as active principle intended to treat and / or prevent aging of the skin is in iiposomal form, as notably described in patent application WO 94 / 22468 filed October 13, 1994 " by Anti Cancer Inc.
- This composition can also contain adjuvants customary in the cosmetic field, such as hydrophilic or iipophilic gelling agents, hydrophilic or Iipophilic additives, preservatives, antioxidants, solvents, perfumes, fillers, filters, odor absorbers and coloring matters.
- adjuvants customary in the cosmetic field, such as hydrophilic or iipophilic gelling agents, hydrophilic or Iipophilic additives, preservatives, antioxidants, solvents, perfumes, fillers, filters, odor absorbers and coloring matters.
- the amounts of these various adjuvants are those conventionally used in the cosmetic field, and for example from 0.01% to 10% of the total weight of the composition.
- These adjuvants depending on their nature, can be introduced into the fatty phase, into the aqueous phase and / or into the lipid spherules.
- emulsifiers which can be used in the invention, there may be mentioned for example glycerol stearate, polysorbate 60 and the mixture of PEG-6 / PEG-32 / Glycol Stearate sold under the name Tefose ⁇ 63 by the company Gattefosse.
- solvents which can be used in the invention mention may be made of lower alcohols, in particular ethanol and isopropanol, propylene glycol.
- hydrophilic gelling agents which can be used in the invention, mention may be made of carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkylacrylate copolymers, polyacrylamides, polysaccharides such as hydroxypropylcellulose, natural gums and clays, and, as lipophilic gelling agents, mention may be made of modified clays such as bentones, metal salts of fatty acids such as aluminum stearates and hydrophobic silica, ethylcellulose, polyethylene.
- carboxyvinyl polymers carboxyvinyl polymers
- acrylic copolymers such as acrylate / alkylacrylate copolymers
- polyacrylamides polysaccharides
- polysaccharides such as hydroxypropylcellulose
- natural gums and clays and, as lipophilic gelling agents
- modified clays such as bentones, metal salts of fatty acids such as aluminum stearates and hydrophobic silica,
- composition may contain other hydrophilic active agents such as proteins or protein hydrolysates, amino acids, polyols, urea, allantoin, sugars and sugar derivatives, water-soluble vitamins, plant extracts and hydroxy acids.
- hydrophilic active agents such as proteins or protein hydrolysates, amino acids, polyols, urea, allantoin, sugars and sugar derivatives, water-soluble vitamins, plant extracts and hydroxy acids.
- vitamin A As lipophilic active agents, retinol (vitamin A) and its derivatives, tocopherol (vitamin E) and its derivatives, essential fatty acids, ceramides other than the compounds of formula (I), essential oils, salicylic acid and its derivatives.
- - keratolytic agents such as alpha- and beta-hydroxycarboxylic or beta-ketocarboxylic acids, their salts, amides or esters and more particularly hydroxy acids such as glycolic acid, lactic acid, salicylic acid, acid citric and generally fruit acids, and n-octanoyl-5-salicylic acid;
- - anti-free radical agents such as alpha-tocopherol or its esters, superoxide dismutases, certain metal chelating agents or ascorbic acid and its esters;
- - anti-acne drugs such as retinoic acid or benzoyl peroxide.
- antagonists of substance P and / or of CGRP Calcitonin Gene Related Peptide or peptide linked to the calcitonin gene
- substance P and / or CGRP antagonists such as those described in French patent applications FR-2719474 and FR-2729855.
- these pharmaceutical compositions are distinguished in particular from cosmetic compositions by the amount of active agent which they contain.
- the amount of active agent which they contain Those skilled in the art, in this case, know how to determine the quantity of active agent which can be used as a function of the desired result but also of the mode of administration envisaged.
- the compound of formula (I) can be used in the preparation of a pharmaceutical composition at a concentration of between 0.01% and 20% and preferably between 0.1% and 10% by weight relative to the weight of composition.
- the cosmetic or pharmaceutical composition according to the invention can be applied to the skin, generally the skin of the face and / or the neck and / or the hands, and optionally left in contact for several hours and optionally rinsed off.
- These applications can be renewed daily for one or more months depending on the individual.
- the subject of the present invention is also a method of cosmetic treatment of human skin, characterized in that it consists in applying to at least part of the skin of the human body, a cosmetic composition comprising an effective amount of at least one compound of formula (I), to leave it in contact with the skin, and optionally to rinse.
- compositions illustrate the invention without limiting it in any way.
- proportions indicated are percentages by weight unless otherwise indicated.
- Example 1 Measurement of the proliferative effect of 2-amino-octadecane-1, 3-diol and its derivatives on cultured keratinocytes:
- HaCat cells (Boukamp et al., J. Cell Biol. Vol. 106, March 1988, 761-771) are cultured in DMEM medium (Gibco Company) containing amino acids (mixture of nonessential amino acids) at the concentration 0.1 mM, penicillin and streptomycin at respective concentrations of 50 International Units per milliliter and 50 ⁇ g / ml, glutamine at 2 mM concentration, sodium pyruvate at 1 mM concentration and 10% fetal calf serum. These cells were seeded at a density of 10,000 cells per well, in the 24 wells of multi-well type plates (Costar, France).
- DMEM medium Gibco Company
- the cells are brought into contact with the various compounds tested in a KBM medium (Clonetics company) containing 0.15 mM of calcium ion, insulin at 5 ⁇ g / ml, hydrocortisone at 0 , 5 ⁇ g / ml, and delipidated bovine serum albumin at 1 ⁇ g / ml.
- a cell count is carried out 5 days after the addition of the different ceramides using a cell counter of the Coulter Counter type.
- the different compounds are tested at 0.5 nM, 5 nM, 50 nM and 500 nM.
- results expressed as a percentage represent the increase in the number of cells relative to the control, that is to say relative to a culture carried out under the same conditions in the absence of sphinganine.
- A 2-amino-octadecane-1, 3-diol
- B 2-N- (2-hydroxy-hexadecanoyl) -amino-octadecane-1, 3-diol
- C 2-N- acetylamino-octadecane-1, 3-diol
- D 2-N-octanoylamino-octadecane-1, 3-diol.
- HaCat cells are cultured as before. They are then seeded at a density of 20,000 cells per well, in the 24 wells of multi-well plates (Costar, France). 24 hours after inoculation, the cells are brought into contact with the various compounds tested in a KBM medium (Clonetics company) containing insulin at 5 ⁇ g / ml and hydrocortisone at 0.5 ⁇ g / ml. Cell viability is evaluated 48 hours later by measuring the mitochondrial respiration. This is carried out using an XTT kit, sold by the company Boehringer and according to the supplier's instructions.
- results expressed as a percentage represent the increase in the number of cells relative to the control, that is to say relative to a culture carried out under the same conditions in the absence of alkane-diol compounds.
- HaCat cells are cultured as before.
- the cells are brought into contact with the various compounds tested in a KBM medium (Clonetics company) containing insulin at 5 ⁇ g / ml and hydrocortisone at 0.5 ⁇ g / ml and 5- bromo-2 'deoxyuridine (BrdU) at 1 ⁇ .M
- KBM medium Cosmetic and Medical Services company
- RhdU 5- bromo-2 'deoxyuridine
- the cell cycle phase is evaluated 48 hours later by measuring the incorporation of BrdU in genomic deoxyribonucleic acid. This is carried out using a "BrdU fast" kit, sold by the company Boehringer and according to the supplier's instructions.
- results expressed as a percentage represent the increase in the number of cells entered in phase S relative to the control, that is to say relative to a culture carried out under the same conditions in the absence of alkane-diol compounds.
- Example 4 Effect of 2-amino-octadecane-1, 3-diol and its derivatives on cell viability in the presence of a sphingenine-based compound, N-acetyl sphingenine.
- HaCat cells are cultured as in Example 2.
- the cells are brought into contact with the various compounds tested in a KBM medium (Clonetics company) containing insulin at 5 ⁇ g / ml and hydrocortisone at 0.5 ⁇ g / ml.
- the cells are cultured in the presence of 2-amino-octadecane-1, 3-diol to be tested until the evaluation of cell viability.
- N-acetyl sphingenine at a concentration of 10 ⁇ M is added to the culture medium for 2 hours at the start of the experiment.
- Cell viability is evaluated 48 hours later by measuring mitochondrial respiration. This is carried out using an XTT kit, sold by the company Boehringer and according to the supplier's instructions.
- results expressed as a percentage represent the number of cells relative to the control (A), that is to say relative to a culture carried out under the same conditions in the absence of alkane-diol compounds and of N-acetyl sphingenine.
- N-acetyl sphingenine causes a decrease in cell viability.
- Example 5 Examples of compositions to be applied to the skin. These compositions can be prepared by simple mixing. The percentages are given by weight of active material relative to the total weight of the composition.
- Carbopol 940 ® marketed by the company GOODRICH 0.6 0 // o
- Nonionic liposome cream Carbopol 940 ® marketed by the company GOODRICH 0.2% Transcutol ® marketed by the company GATTEFOSSE 3% Triethanolamine 0.2% Polyglyceryl-3-cetyl ether 3.8% ⁇ sitosterol 3.8% Diketyl phosphate 0.4% NaOH 0.007 %
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Abstract
The invention concerns the use, as main active principle in a composition or for preparing a pharmaceutical composition, of an effective amount of at least a 2-amino-alkane polyol, or one of its derivatives for treating skin ageing signs.
Description
UTILISAΉON D'UN 2-AMINO-ALCANE POLYOL POUR LE TRAITEMENT DE VIEILLISSEMENT CUTANEUSE OF A 2-AMINO-ALKANE POLYOL FOR THE TREATMENT OF SKIN AGING
La présente invention concerne l'utilisation, à titre de principe actif dans une composition cosmétique ou pour la préparation d'une composition pharmaceutique, d'une quantité efficace d'au moins un 2-amino-alcane-1 ,3-diol, ou de l'un de ses dérivés, destinée à traiter les signes du vieillissement cutané ainsi qu'à un procédé non thérapeutique de traitement du vieillissement cutané. Le vieillissement cutané, résultant d'effets sur la peau de facteurs intrinsèques ou extrinsèques, se traduit par l'apparition de rides et ridules, par le jaunissement de la peau qui développe un aspect parcheminé accompagné de l'apparition de taches pigmentaires, par la désorganisation des fibres d'élastine et de collagène entraînant une perte d'élasticité, de souplesse et de fermeté et par l'apparition de télangiectasies.The present invention relates to the use, as active principle in a cosmetic composition or for the preparation of a pharmaceutical composition, of an effective amount of at least one 2-amino-alkane-1, 3-diol, or of one of its derivatives, intended for treating the signs of skin aging as well as a non-therapeutic method for treating skin aging. Skin aging, resulting from effects on the skin of intrinsic or extrinsic factors, is manifested by the appearance of fine lines and wrinkles, by the yellowing of the skin which develops a parchment appearance accompanied by the appearance of pigment spots, by the disorganization of the elastin and collagen fibers leading to a loss of elasticity, flexibility and firmness and by the appearance of telangiectasias.
Certains de ces signes du vieillissement sont plus particulièrement liés au vieillissement intrinsèque ou physiologique, c'est-à-dire au vieillissement « normal » lié à l'âge, alors que d'autres sont plus spécifiques du vieillissement extrinsèque, c'est-à-dire du vieillissement provoqué d'une manière générale par l'environnement ; il s'agit plus particulièrement du photo-vieillissement dû à l'exposition au soleil, à la lumière ou à tout autre rayonnement.Some of these signs of aging are more particularly linked to intrinsic or physiological aging, that is to say to “normal” aging linked to age, while others are more specific to extrinsic aging, ie that is to say aging generally caused by the environment; this is more particularly photo-aging due to exposure to the sun, light or any other radiation.
L'invention s'intéresse au vieillissement intrinsèque ou physiologique ainsi qu'au vieillissement extrinsèque.The invention is concerned with intrinsic or physiological aging as well as extrinsic aging.
Les changements de la peau résultants du vieillissement intrinsèque ou physiologique sont la conséquence d'une sénescence génétiquement programmée où interviennent des facteurs endogènes. Ce vieillissement intrinsèque provoque notamment un ralentissement du renouvellement des cellules de la peau. Histologiquement la peau est globalement amincie, tant au niveau épidermique que dermique. La densité des macromolécules fibreuses du derme (élastine et collagène) est diminuée.The skin changes resulting from intrinsic or physiological aging are the consequence of genetically programmed senescence in which endogenous factors intervene. This intrinsic aging notably causes a slowing down of the renewal of skin cells. Histologically the skin is generally thinned, both epidermally and dermally. The density of the fibrous macromolecules of the dermis (elastin and collagen) is reduced.
Au contraire, le vieillissement extrinsèque entraîne des altérations cliniques telles que des rides épaisses et la formation d'une peau molle et/ou tannée, et des changements histopathologiques tels qu'une excessive accumulation de matière élastique dans le derme supérieur et une dégénérescence des fibres de collagène.On the contrary, extrinsic aging leads to clinical alterations such as thick wrinkles and the formation of soft and / or tanned skin, and histopathological changes such as an excessive accumulation of elastic material in the upper dermis and degeneration of the fibers. collagen.
On recherche depuis de nombreuses années, dans l'industrie cosmétique ou pharmaceutique, des substances permettant de supprimer ou de réduire l'effet du vieillissement cutané, et notamment de contrecarrer le ralentissement du renouvellement des cellules de la peau.For many years, research has been carried out in the cosmetic or pharmaceutical industry on substances which make it possible to suppress or reduce the effect of skin aging, and in particular to counteract the slowing down of the renewal of skin cells.
On connaît dans l'art antérieur divers agents destinés à lutter contre le vieillissement cutané.Various agents are known in the prior art intended to combat skin aging.
Ainsi, le brevet US-A-4 603 146 décrit l'emploi d'acide rétinoïque et de ses dérivés dans des compositions cosmétiques, en vue de lutter contre le vieillis-sement cutané.
Par ailleurs, de nombreux brevets et publications (voir par exemple la demande EP-A- 413 528) ainsi que de nombreuses compositions cosmétiques du commerce enseignent l'emploi des α-hydroxyacides comme l'acide lactique, l'acide glycolique ou encore l'acide citrique pour traiter le vieillissement cutané.Thus, US Pat. No. 4,603,146 describes the use of retinoic acid and its derivatives in cosmetic compositions, with a view to combating skin aging. In addition, numerous patents and publications (see for example application EP-A-413 528) as well as many commercial cosmetic compositions teach the use of α-hydroxy acids such as lactic acid, glycolic acid or else citric acid to treat skin aging.
On connaît enfin les bêta-hydroxy-acides et plus spécialement l'acide salicylique ainsi que ses dérivés pour leurs propriétés desquamantes (voir les documents WO-A-93/10756 et US-A-4 767 750).Finally, beta-hydroxy acids and more particularly salicylic acid and its derivatives are known for their flaking properties (see documents WO-A-93/10756 and US-A-4 767 750).
Tous ces composés ont une action contre le vieillissement de la peau, consistant en une desquamation, c'est-à-dire l'élimination des cellules « mortes » situées à la surface du stratum corneum. Cette propriété desquamante est aussi appelée, souvent à tort, propriété kératolytique. Mais ces composés présentent également des effets secondaires, qui consistent en des picotements, des tiraillements, des échauffements et des rougeurs désagréables pour l'utilisateur.All of these compounds have an action against aging of the skin, consisting of desquamation, that is to say the elimination of "dead" cells located on the surface of the stratum corneum. This desquamating property is also called, often wrongly, keratolytic property. But these compounds also have side effects, which consist of tingling, tightness, overheating and redness unpleasant for the user.
On constate donc que subsiste le besoin d'agents anti-vieillissement ayant une action au moins aussi efficace que celle des composés de l'art antérieur, mais ne présentant pas leurs inconvénients.It is therefore found that there remains the need for anti-aging agents having an action at least as effective as that of the compounds of the prior art, but not having their drawbacks.
De manière surprenante, la demanderesse a maintenant découvert que certains composés de type 2-amino-alcane polyol ont un effet sur le vieillissement de la peau.Surprisingly, the applicant has now discovered that certain compounds of the 2-amino-alkane polyol type have an effect on the aging of the skin.
L'invention a donc pour objet l'utilisation d'un 2-amino-alcane polyol de formule (I) (ci-dessous), ou de l'un de ses dérivés, dans une composition cosmétique ou dermatologique à application topique, destinée à traiter certains signes du vieillissement endogène et/ou exogène.The subject of the invention is therefore the use of a 2-amino-alkane polyol of formula (I) (below), or of one of its derivatives, in a cosmetic or dermatological composition for topical application, intended to treat certain signs of endogenous and / or exogenous aging.
Ce traitement peut être réalisé à titre préventif et/ou curatif.This treatment can be carried out as a preventive and / or curative measure.
Les composés de type 2-amino-alcane polyol ou leur dérivés peuvent faire partie de ces composés des tissus que l'on nomme du terme très général de sphingolipides.Compounds of the 2-amino-alkane polyol type or their derivatives can be part of these tissue compounds which are called by the very general term of sphingolipids.
Parmi ces sphingolipides, les dérivés N-acylés à base sphinganine [(2S, 3R)-2- amino-1 ,3-octadécanediol] sont des céramides majoritairement présents dans le cheveu, alors que les dérivés analogues à base de phytosphingosine [(2S, 3S, 4R)-2-amino-1 ,3,4-octadécane-triol), autres céramides, font partie des lipides majoritairement présents dans le stratum corneum de la peau. Les céramides sont utilisés en cosmétique sous forme naturelle ou synthétique dans des compositions destinées par exemple à renforcer l'effet barrière du stratum corneum afin de réduire la perte en eau et donc le dessèchement de la peau (GB 2 178 312, GB 2 213 723, EP 227 994, EP 282 616, EP 556 957).Among these sphingolipids, the N-acylated derivatives based on sphinganine [(2S, 3R) -2-amino-1, 3-octadecanediol] are ceramides predominantly present in the hair, while analogous derivatives based on phytosphingosine [(2S , 3S, 4R) -2-amino-1, 3,4-octadecane-triol), other ceramides, are part of the lipids mainly present in the stratum corneum of the skin. Ceramides are used in cosmetics in natural or synthetic form in compositions intended for example to reinforce the barrier effect of the stratum corneum in order to reduce the loss of water and therefore the drying of the skin (GB 2 178 312, GB 2 213 723 , EP 227 994, EP 282 616, EP 556 957).
Ils sont également utilisés dans des compositions cosmétiques pour leurs propriétés conférant à la peau une meilleure élasticité (EP 500 437) ou encore dans des compositions à usage capillaire pour renforcer le cheveu et/ou réparer
les dégâts causés par les agressions continuelles que celui-ci subit.They are also used in cosmetic compositions for their properties giving the skin better elasticity (EP 500 437) or in compositions for hair use to strengthen the hair and / or repair the damage caused by the continual assaults that this one undergoes.
A la connaissance de la demanderesse, il n'a jamais été décrit ni même suggéré pour les 2-amino-alcane polyols de formule (l), ou leurs dérivés, un effet sur la prolifération des cellules et encore moins des kératinocytes.To the knowledge of the applicant, it has never been described or even suggested for the 2-amino-alkane polyols of formula (I), or their derivatives, an effect on the proliferation of cells and even less of keratinocytes.
C'est sur la base de cette propriété nouvelle de ces amino-polyols que la demanderesse a pu montrer que ces composés ont également un effet sur le vieillissement cutané.It is on the basis of this new property of these amino polyols that the applicant has been able to show that these compounds also have an effect on skin aging.
L'invention concerne l'utilisation dans une composition cosmétique ou pour la préparation d'une composition pharmaceutique destinée à traiter les signes du vieillissement cutané, d'au moins un composé de formule générale (I) :The invention relates to the use in a cosmetic composition or for the preparation of a pharmaceutical composition intended for treating the signs of skin aging, of at least one compound of general formula (I):
dans laquelle R-| représente un radical hydrocarboné linéaire ou ramifié, éventuellement hydroxylé, saturé ou insaturé, ayant de 4 à 28 atomes de carbone, R2 représente un atome d'hydrogène ou le radicalin which R- | represents a linear or branched hydrocarbon radical, optionally hydroxylated, saturated or unsaturated, having 4 to 28 carbon atoms, R2 represents a hydrogen atom or the radical
, o, o
dans lequel R3 représente un radical hydrocarboné linéaire ou ramifié, saturé ou insaturé, ayant de 1 à 11 atomes de carbone ou un radical hydrocarboné linéaire ou ramifié, hydroxylé, saturé ou insaturé, ayant de 1 à 29 atomes de carbone, l'hydroxyle pouvant être estérifié par une chaîne acyle ayant de 2 à 30 atomes de carbone, linéaire ou ramifiée, saturée ou insaturée ;in which R3 represents a linear or branched, saturated or unsaturated hydrocarbon-based radical having from 1 to 11 carbon atoms or a linear or branched, hydroxylated, saturated or unsaturated hydrocarbon-based radical having from 1 to 29 carbon atoms, the hydroxyl being capable of be esterified by an acyl chain having from 2 to 30 carbon atoms, linear or branched, saturated or unsaturated;
X représente un atome d'hydrogène ou le radical OH ; ou d'au moins l'un de ses isomères optiques ou l'un des diasteréoisomères.X represents a hydrogen atom or the OH radical; or at least one of its optical isomers or one of the diastereoisomers.
R-1 contient de préférence de 6 à 22 atomes de carbone et encore plus préférentiellement de 10 à 18 atomes de carbone. de préférence R2 représente H ou un radicalR-1 preferably contains from 6 to 22 carbon atoms and even more preferably from 10 to 18 carbon atoms. preferably R2 represents H or a radical
.R,.R,
O et R3 représente un radical hydrocarboné linéaire ou ramifié, saturé ou insaturé, ayant de 1 à 9 atomes de carbone ou un radical hydrocarboné linéaire ou ramifié, hydroxylé, saturé ou insaturé, ayant de 1 à 21 atomes de carbone.O and R3 represents a linear or branched, saturated or unsaturated hydrocarbon radical having from 1 to 9 carbon atoms or a linear or branched, hydroxylated, saturated or unsaturated hydrocarbon radical, having from 1 to 21 carbon atoms.
Préférentiellement, Ri représente un radical hydrocarboné saturé et/ou linéaire plus particulièrement un radical hydrocarboné linéaire saturé.
Préférentiellement, R-| représente un radical hydrocarboné saturé ayant 14 atomes de carbone, et encore plus préférentiellement R^ représente un radical hydrocarboné linéaire, saturé, ayant 14 atomes de carbone.Preferably, Ri represents a saturated and / or linear hydrocarbon radical, more particularly a saturated linear hydrocarbon radical. Preferably, R- | represents a saturated hydrocarbon radical having 14 carbon atoms, and even more preferably R ^ represents a linear, saturated hydrocarbon radical having 14 carbon atoms.
L'agent favorisant le soin et/ou la prévention du vieillissement peut être un mélange de composés de formule (I), pour lesquels R, et/ou R2 sont des chaînes de longueurs différentes.The agent promoting the care and / or prevention of aging can be a mixture of compounds of formula (I), for which R, and / or R 2 are chains of different lengths.
Ces composés peuvent être utilisés sous forme d'isomère pur ou de mélange d'isomères.These compounds can be used in the form of a pure isomer or a mixture of isomers.
Ces composés présentent l'avantage de ne pas induire d'effets secondaires gênants, ce qui rend leur utilisation sans risque pour l'utilisateur.These compounds have the advantage of not inducing annoying side effects, which makes their use without risk for the user.
On peut citer comme composés de formule (I) utilisables selon l'invention :Mention may be made, as compounds of formula (I) which can be used according to the invention:
- le 2- amino-octadécane-1 ,3-diol,- 2-amino-octadecane-1, 3-diol,
- le 2-N-acétylamino-octadécane-1 ,3-diol,- 2-N-acetylamino-octadecane-1, 3-diol,
- le 2-N-octanoylamino-octadécane-1 ,3-diol,- 2-N-octanoylamino-octadecane-1, 3-diol,
- le 2-N-(2-hydroxy-hexadécanoyl)-amino-octadécane-1 ,3-diol, - le 2-N-(2-hydroxy-docosanoyi)-amino-octadécane-1 ,3-diol,- 2-N- (2-hydroxy-hexadecanoyl) -amino-octadecane-1, 3-diol, - 2-N- (2-hydroxy-docosanoyi) -amino-octadecane-1, 3-diol,
- le 2-amino-octadécane-1 ,3,4-triol,- 2-amino-octadecane-1, 3,4-triol,
- le 2-N-(2-hydroxy-hexadécanoyl)-amino-octadécane-1 ,3,4-triol- 2-N- (2-hydroxy-hexadecanoyl) -amino-octadecane-1, 3,4-triol
- le 2-N-hexanoylamino-octadécane-1 ,3-diol- 2-N-hexanoylamino-octadecane-1, 3-diol
- le 2-N-octanoylamino-octadécane-1 ,3,4-triol.- 2-N-octanoylamino-octadecane-1, 3,4-triol.
Préférentiellement, selon l'invention, on utilise le 2-N-acétylamino-octadécane- 1 ,3-diol ou le 2-N-octanoylamino-octadécane-1 ,3-diol.Preferably, according to the invention, 2-N-acetylamino-octadecane-1, 3-diol or 2-N-octanoylamino-octadecane-1, 3-diol is used.
L'invention a donc pour objet l'utilisation d'un 2-amino-alcane-1 ,3-diol de formule (I) (ci-dessous), ou de l'un de ses dérivés, dans une composition cosmétique ou dermatologique à application topique, destinée à traiter les rides et/ou les ridules et/ou le jaunissement de la peau et/ou l'aspect parcheminé de la peau et/ou les taches pigmentaires de la peau et/ou les télangiectasies et ou la perte d'élasticité, de souplesse et/ou de fermeté de la peau.A subject of the invention is therefore the use of a 2-amino-alkane-1, 3-diol of formula (I) (below), or of one of its derivatives, in a cosmetic or dermatological composition for topical application, intended to treat wrinkles and / or fine lines and / or yellowing of the skin and / or the parchment appearance of the skin and / or pigmented spots of the skin and / or telangiectasias and or loss elasticity, flexibility and / or firmness of the skin.
La quantité de composés de formule (I) utilisable selon l'invention dépend, bien entendu, de la nature du composé utilisé, de ses propriétés physico-chimiques et de son mode d'application. L'homme du métier sait ajuster la quantité de composé de formule (I) à utiliser selon les besoins.The amount of compounds of formula (I) which can be used according to the invention depends, of course, on the nature of the compound used, on its physicochemical properties and on its mode of application. A person skilled in the art knows how to adjust the amount of compound of formula (I) to be used as required.
A titre indicatif les composés de formule (I) peuvent être utilisés à des concentrations en poids comprises entre 10^% et 20%, et de préférence entre 10"3 % et 10% dans la composition.By way of indication, the compounds of formula (I) can be used at concentrations by weight of between 10 ^% and 20%, and preferably between 10 "3 % and 10% in the composition.
Lorsque le composé de formule (I) est utilisé dans une composition qui doit être appliquée sur la peau, cette composition peut se présenter sous toutes les formes galéniques normalement utilisées.
Pour une application topique sur la peau, la composition peut avoir la forme notamment d'une solution aqueuse, alcoolique, hydroalcoolique ou huileuse ou de dispersion du type lotion ou sérum, d'une émulsion de consistance liquide ou semi-liquide du type lait, obtenue par dispersion d'une phase grasse dans une phase aqueuse (H/E) ou inversement (E/H), ou d'une suspension ou d'une émulsion de consistance molle du type crème, mousse ou gel aqueux ou anhydre, ou encore de microcapsules ou microparticules, ou d'une dispersion vésiculaire de type ionique et/ou non ionique. Elle peut également prendre la forme d'une composition pour aérosol comprenant également un agent propulseur sous pression.When the compound of formula (I) is used in a composition which must be applied to the skin, this composition can be in all the galenical forms normally used. For a topical application to the skin, the composition may take the form in particular of an aqueous, alcoholic, hydroalcoholic or oily solution or of dispersion of the lotion or serum type, of an emulsion of liquid or semi-liquid consistency of the milk type, obtained by dispersing a fatty phase in an aqueous phase (O / W) or vice versa (W / O), or a suspension or an emulsion of soft consistency of the cream, foam or aqueous or anhydrous gel type, or still microcapsules or microparticles, or a vesicular dispersion of the ionic and / or nonionic type. It can also take the form of an aerosol composition also comprising a pressurized propellant.
Quelque soit sa forme, cette composition est préparée selon les méthodes usuelles. Les quantités des différents constituants de la composition selon l'invention sont celles classiquement utilisées dans les domaines considérés.Whatever its form, this composition is prepared according to the usual methods. The amounts of the various constituents of the composition according to the invention are those conventionally used in the fields considered.
Lorsque la composition est une émulsion, la proportion de la phase grasse peut aller de 5 % à 80 % en poids, et de préférence de 5 % à 50 % en poids par rapport au poids total de la composition. Les huiles, les cires, les emulsionnants et les co-émulsionnants utilisés dans la composition sous forme d'émulsion sont choisis parmi ceux classiquement utilisés dans le domaine cosmétique. L'émulsionnant et le co-émulsionnant sont présents, dans la composition, en une proportion allant de 0,3 % à 30 % en poids, et de préférence de 0,5 à 20 % en poids par rapport au poids total de la composition. L'émulsion peut, en outre, contenir des vésicules lipidiques.When the composition is an emulsion, the proportion of the fatty phase can range from 5% to 80% by weight, and preferably from 5% to 50% by weight relative to the total weight of the composition. The oils, waxes, emulsifiers and co-emulsifiers used in the composition in the form of an emulsion are chosen from those conventionally used in the cosmetic field. The emulsifier and the co-emulsifier are present in the composition in a proportion ranging from 0.3% to 30% by weight, and preferably from 0.5 to 20% by weight relative to the total weight of the composition . The emulsion may, in addition, contain lipid vesicles.
Lorsque la composition est une solution ou un gel huileux, la phase grasse peut représenter plus de 90 % du poids total de la composition.When the composition is an oily solution or gel, the fatty phase can represent more than 90% of the total weight of the composition.
On peut également envisager que la composition comprenant au moins un composé de formule (I) à titre de principe actif destiné à soigner et/ou prévenir le vieillissement de la peau soit sous forme iiposomée, telle que notamment décrite dans la demande de brevet WO 94/22468 déposée le 13 octobre 1994" par la société Anti Cancer Inc.It is also conceivable that the composition comprising at least one compound of formula (I) as active principle intended to treat and / or prevent aging of the skin is in iiposomal form, as notably described in patent application WO 94 / 22468 filed October 13, 1994 " by Anti Cancer Inc.
Cette composition peut contenir également des adjuvants habituels dans le domaine cosmétique, tels que les gélifiants hydrophiles ou iipophiles, les additifs hydrophiles ou Iipophiles, les conservateurs, les antioxydants, les solvants, les parfums, les charges, les filtres, les absorbeurs d'odeur et les matières colorantes. Les quantités de ces différents adjuvants sont celles classiquement utilisées dans le domaine cosmétique, et par exemple de 0,01 % à 10 % du poids total de la composition. Ces adjuvants, selon leur nature, peuvent être introduits dans la phase grasse, dans la phase aqueuse et/ou dans les sphérules lipidiques.This composition can also contain adjuvants customary in the cosmetic field, such as hydrophilic or iipophilic gelling agents, hydrophilic or Iipophilic additives, preservatives, antioxidants, solvents, perfumes, fillers, filters, odor absorbers and coloring matters. The amounts of these various adjuvants are those conventionally used in the cosmetic field, and for example from 0.01% to 10% of the total weight of the composition. These adjuvants, depending on their nature, can be introduced into the fatty phase, into the aqueous phase and / or into the lipid spherules.
Comme huiles ou cires utilisables dans l'invention, on peut citer les huiles minérales (huile de vaseline), les huiles végétales (fraction liquide du beurre de
karité, huile de tournesol), les huiles animales (perhydrosqualène), les huiles de synthèse (huile de purceliin), les huiles ou cires siliconées (cyclométhicone) et les huiles fluorées (perfluoropolyéthers), les cires d'abeille, de carnauba ou paraffine. On peut ajouter à ces huiles des alcools gras et des acides gras (acide stéarique).As oils or waxes which can be used in the invention, mention may be made of mineral oils (petroleum jelly oil), vegetable oils (liquid fraction of butter from shea, sunflower oil), animal oils (perhydrosqualene), synthetic oils (purceliin oil), silicone oils or waxes (cyclomethicone) and fluorinated oils (perfluoropolyethers), beeswax, carnauba or paraffin . Fatty alcohols and fatty acids (stearic acid) can be added to these oils.
Comme emulsionnants utilisables dans l'invention, on peut citer par exemple le stéarate de glycérol, le polysorbate 60 et le mélange de PEG-6/PEG-32/Glycol Stéarate vendu sous la dénomination de Tefose^ 63 par la société Gattefosse.As emulsifiers which can be used in the invention, there may be mentioned for example glycerol stearate, polysorbate 60 and the mixture of PEG-6 / PEG-32 / Glycol Stearate sold under the name Tefose ^ 63 by the company Gattefosse.
Comme solvants utilisables dans l'invention, on peut citer les alcools inférieurs, notamment l'éthanol et l'isopropanol, le propylène giycol.As solvents which can be used in the invention, mention may be made of lower alcohols, in particular ethanol and isopropanol, propylene glycol.
Comme gélifiants hydrophiles utilisables dans l'invention, on peut citer les polymères carboxyvinyliques (carbomer), les copolymeres acryliques tels que les copolymeres d'acrylates/alkylacrylates, les polyacrylamides, les polysaccharides tels que l'hydroxypropylcellulose, les gommes naturelles et les argiles, et, comme gélifiants Iipophiles, on peut citer les argiles modifiées comme les bentones, les sels métalliques d'acides gras comme les stéarates d'aluminium et la silice hydrophobe, éthylcellulose, polyéthylène.As hydrophilic gelling agents which can be used in the invention, mention may be made of carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkylacrylate copolymers, polyacrylamides, polysaccharides such as hydroxypropylcellulose, natural gums and clays, and, as lipophilic gelling agents, mention may be made of modified clays such as bentones, metal salts of fatty acids such as aluminum stearates and hydrophobic silica, ethylcellulose, polyethylene.
La composition peut contenir d'autres actifs hydrophiles comme les protéines ou les hydrolysats de protéine, les acides aminés, les polyols, l'urée, l'allantoïne, les sucres et les dérivés de sucre, les vitamines hydrosolubles, les extraits végétaux et les hydroxyacides.The composition may contain other hydrophilic active agents such as proteins or protein hydrolysates, amino acids, polyols, urea, allantoin, sugars and sugar derivatives, water-soluble vitamins, plant extracts and hydroxy acids.
Comme actifs Iipophiles, on peut utiliser le rétinol (vitamine A) et ses dérivés, le tocophérol (vitamine E) et ses dérivés, les acides gras essentiels, les céramides autres que les composés de formule (I), les huiles essentielles, l'acide salicylique et ses dérivés.As lipophilic active agents, retinol (vitamin A) and its derivatives, tocopherol (vitamin E) and its derivatives, essential fatty acids, ceramides other than the compounds of formula (I), essential oils, salicylic acid and its derivatives.
En particulier, il est possible aussi d'utiliser en association avec le composé de formule (I) utilisé selon l'invention des composés améliorant encore l'activité sur le soin et/ou la prévention du vieillissement, et ayant déjà été décrits pour cette activité.In particular, it is also possible to use, in combination with the compound of formula (I) used according to the invention, compounds which further improve the activity on the care and / or prevention of aging, and which have already been described for this purpose. activity.
Parmi ces derniers composés, on peut plus particulièrement citer à titre non limitatif :Among these latter compounds, there may be more particularly mentioned, without implying any limitation:
- les agents kératolytiques tels que les acides alpha- et bêta- hydroxycarboxyliques ou bêta-cétocarboxyliques, leurs sels, amides ou esters et plus particulièrement les hydroxyacides tels que l'acide glycolique, l'acide lactique, l'acide salicylique, l'acide citrique et de manière générale les acides de fruits, et l'acide n-octanoyl-5-salicylique ;- keratolytic agents such as alpha- and beta-hydroxycarboxylic or beta-ketocarboxylic acids, their salts, amides or esters and more particularly hydroxy acids such as glycolic acid, lactic acid, salicylic acid, acid citric and generally fruit acids, and n-octanoyl-5-salicylic acid;
- les agents anti-radicaux libres, tels que l'alpha-tocophérol ou ses esters, les superoxyde dismutases, certains chelatants de métaux ou l'acide ascorbique et ses esters ;- anti-free radical agents, such as alpha-tocopherol or its esters, superoxide dismutases, certain metal chelating agents or ascorbic acid and its esters;
- les antiacnéiques comme l'acide rétinoïque ou le peroxyde de benzoyle.
On peut, par ailleurs, associer aux composés de formule (I) des antagonistes de substance P et/ou de CGRP (Calcitonin Gène Related Peptide ou peptide lié au gène de la calcitonine) tels que l'Iris Pallida et les sels de strontium, notamment les chlorures et les nitrates de strontium, ou des antagonistes de substance P et/ou de CGRP tels que ceux décrits dans les demandes de brevet français FR- 2719474 et FR-2729855. Une telle association permet de garantir une tolérance parfaite de ces compositions, même par des peaux très sensibles.- anti-acne drugs such as retinoic acid or benzoyl peroxide. It is also possible to combine the compounds of formula (I) with antagonists of substance P and / or of CGRP (Calcitonin Gene Related Peptide or peptide linked to the calcitonin gene) such as Iris Pallida and strontium salts, in particular strontium chlorides and nitrates, or substance P and / or CGRP antagonists such as those described in French patent applications FR-2719474 and FR-2729855. Such an association makes it possible to guarantee perfect tolerance of these compositions, even for very sensitive skin.
Il est possible d'utiliser au moins un des composés répondant à la formule (I) dans la préparation d'une composition pharmaceutique, particulièrement dermatologique, destinée à traiter et/ou prévenir le vieillissement cutané.It is possible to use at least one of the compounds corresponding to formula (I) in the preparation of a pharmaceutical composition, particularly a dermatological composition, intended for treating and / or preventing skin aging.
En général, ces compositions pharmaceutiques se distinguent notamment des compositions cosmétiques par la quantité d'actif qu'elles contiennent. L'homme du métier, dans ce cas, sait déterminer la quantité d'actif utilisable en fonction du résultat recherché mais également du mode d'administration envisagé. A titre indicatif, le composé de formule (I) peut être utilisé dans la préparation d'une composition pharmaceutique à une concentration comprise entre 0,01 % et 20% et préférentiellement entre 0,1% et 10% en poids par rapport au poids de la composition.In general, these pharmaceutical compositions are distinguished in particular from cosmetic compositions by the amount of active agent which they contain. Those skilled in the art, in this case, know how to determine the quantity of active agent which can be used as a function of the desired result but also of the mode of administration envisaged. As an indication, the compound of formula (I) can be used in the preparation of a pharmaceutical composition at a concentration of between 0.01% and 20% and preferably between 0.1% and 10% by weight relative to the weight of composition.
La composition cosmétique ou pharmaceutique selon l'invention peut être appliquée sur la peau, généralement la peau du visage et/ou du cou et/ou des mains, et éventuellement laissée en contact plusieurs heures et éventuellement rincée. On peut, par exemple, appliquer la composition contenant une quantité efficace d'au moins un composé de formule (I), le soir, garder celle-ci au contact toute la nuit et éventuellement effectuer un lavage le matin. Ces applications peuvent être renouvelées quotidiennement pendant un ou plusieurs mois suivant les individus.The cosmetic or pharmaceutical composition according to the invention can be applied to the skin, generally the skin of the face and / or the neck and / or the hands, and optionally left in contact for several hours and optionally rinsed off. One can, for example, apply the composition containing an effective amount of at least one compound of formula (I), in the evening, keep it in contact overnight and possibly perform a wash in the morning. These applications can be renewed daily for one or more months depending on the individual.
Ainsi, la présente invention a également pour objet un procédé de traitement cosmétique de la peau humaine, caractérisé par le fait qu'il consiste à appliquer sur au moins une partie de la peau du corps humain, une composition cosmétique comprenant une quantité efficace d'au moins un composé de formule (I), à laisser celle-ci en contact avec la peau, et éventuellement à rincer.Thus, the subject of the present invention is also a method of cosmetic treatment of human skin, characterized in that it consists in applying to at least part of the skin of the human body, a cosmetic composition comprising an effective amount of at least one compound of formula (I), to leave it in contact with the skin, and optionally to rinse.
Les exemples et compositions suivants illustrent l'invention sans la limiter aucunement. Dans les compositions les proportions indiquées sont des pourcentages en poids sauf indications contraires.The following examples and compositions illustrate the invention without limiting it in any way. In the compositions the proportions indicated are percentages by weight unless otherwise indicated.
Exemple 1 : Mesure de l'effet prolifératif du 2-amino-octadécane-1 ,3-diol et de
ses dérivés sur des kératinocytes en culture :Example 1: Measurement of the proliferative effect of 2-amino-octadecane-1, 3-diol and its derivatives on cultured keratinocytes:
Des cellules HaCat (Boukamp et collaborateurs, J. Cell Biol. Vol. 106, Mars 1988, 761-771) sont cultivées dans du milieu DMEM (Société Gibco) contenant des acides aminés (mélange d'acides aminés non essentiels) à la concentration de 0,1 mM, de la pénicilline et de la streptomycine aux concentrations respectives de 50 Unités Internationales par millilitre et de 50 μg/ml, de la glutamine à la concentration de 2 mM, du pyruvate de sodium à la concentration de 1 mM et du sérum de veau foetal à 10%. Ces cellules ont été ensemencées à la densité de 10000 cellules par puits, dans les 24 puits de plaques du type multipuits (Costar, France).HaCat cells (Boukamp et al., J. Cell Biol. Vol. 106, March 1988, 761-771) are cultured in DMEM medium (Gibco Company) containing amino acids (mixture of nonessential amino acids) at the concentration 0.1 mM, penicillin and streptomycin at respective concentrations of 50 International Units per milliliter and 50 μg / ml, glutamine at 2 mM concentration, sodium pyruvate at 1 mM concentration and 10% fetal calf serum. These cells were seeded at a density of 10,000 cells per well, in the 24 wells of multi-well type plates (Costar, France).
24 heures après ensemencement, les cellules sont mises en contact avec les différents composés testés dans un milieu KBM (société Clonetics) contenant 0,15 mM d'ion calcium, de l'insuline à 5 μg/ml, de l'hydrocortisone à 0,5 μg/ml, et de la serumalbumine bovine délipidée à 1 μg/ml.24 hours after inoculation, the cells are brought into contact with the various compounds tested in a KBM medium (Clonetics company) containing 0.15 mM of calcium ion, insulin at 5 μg / ml, hydrocortisone at 0 , 5 μg / ml, and delipidated bovine serum albumin at 1 μg / ml.
Un comptage cellulaire est réalisé 5 jours après l'addition des différents céramides grâce à un compteur de cellules du type Coulter Counter.A cell count is carried out 5 days after the addition of the different ceramides using a cell counter of the Coulter Counter type.
Les différents composés sont testés à 0,5 nM, 5 nM, 50 nM et 500 nM.The different compounds are tested at 0.5 nM, 5 nM, 50 nM and 500 nM.
Les résultats exprimés en pourcentage représentent l'augmentation du nombre de cellules par rapport au contrôle, c'est à dire par rapport à une culture effectuée dans les mêmes conditions en l'absence de sphinganine.The results expressed as a percentage represent the increase in the number of cells relative to the control, that is to say relative to a culture carried out under the same conditions in the absence of sphinganine.
Les différents composés testés sont : A : 2-amino-octadécane-1 ,3-diol, B : 2-N-(2-hydroxy-hexadécanoyl)-amino-octadécane-1 ,3-diol, C : 2-N-acétylamino-octadécane-1 ,3-diol, D : 2-N-octanoylamino-octadécane-1 ,3-diol.The different compounds tested are: A: 2-amino-octadecane-1, 3-diol, B: 2-N- (2-hydroxy-hexadecanoyl) -amino-octadecane-1, 3-diol, C: 2-N- acetylamino-octadecane-1, 3-diol, D: 2-N-octanoylamino-octadecane-1, 3-diol.
A B C DA B C D
0,5 nM 7 26 17 150.5 nM 7 26 17 15
5 nM 15 36 34 185 nM 15 36 34 18
50 nM 17 42 29 3150 nM 17 42 29 31
500 nM 30 22 35 27500 nM 30 22 35 27
Ces résultats montrent que le 2-amino-octadécane-1 ,3-diol et ses dérivés ont une activité proliférative sur les kératinocytes en culture.These results show that 2-amino-octadecane-1, 3-diol and its derivatives have a proliferative activity on keratinocytes in culture.
Exemple 2 : Mesure de l'effet du 2-amino-octadécane-1 ,3-diol et de ses dérivés sur la viabilité cellulaire :Example 2: Measurement of the effect of 2-amino-octadecane-1, 3-diol and its derivatives on cell viability:
Des cellules HaCat sont cultivées comme précédemment. Elles sont ensuite ensemencées à la densité de 20000 cellules par puits, dans les 24 puits de plaques du type multipuits (Costar, France). 24 heures après ensemencement, les cellules sont mises en contact avec les différents composés testés dans un milieu KBM (société Clonetics) contenant de l'insuline à 5 μg/ml et de l'hydrocortisone à 0,5 μg/ml. La viabilité cellulaire est évaluée 48 heures plus tard par la mesure de la
respiration mitochondriale. Celle-ci est réalisée à l'aide d'un kit XTT, vendu par la société Boehringer et selon les prescriptions du fournisseur.HaCat cells are cultured as before. They are then seeded at a density of 20,000 cells per well, in the 24 wells of multi-well plates (Costar, France). 24 hours after inoculation, the cells are brought into contact with the various compounds tested in a KBM medium (Clonetics company) containing insulin at 5 μg / ml and hydrocortisone at 0.5 μg / ml. Cell viability is evaluated 48 hours later by measuring the mitochondrial respiration. This is carried out using an XTT kit, sold by the company Boehringer and according to the supplier's instructions.
Les composés A, et B de l'exemple précédent ont été testés à la concentration de 50 nM, de même qu'un dérivé à base sphingénine : la N- palmitoylsphingénine de chez Sigma (C16H).Compounds A and B of the previous example were tested at a concentration of 50 nM, as well as a derivative based on sphingenine: N-palmitoylsphingenine from Sigma (C16H).
Les résultats exprimés en pourcentage représentent l'augmentation du nombre de cellules par rapport au contrôle, c'est à dire par rapport à une culture effectuée dans les mêmes conditions en l'absence de composés alcane-diol .The results expressed as a percentage represent the increase in the number of cells relative to the control, that is to say relative to a culture carried out under the same conditions in the absence of alkane-diol compounds.
Contrôle 0__Control 0__
A +17A +17
B +20B +20
C16H -25C16H -25
Les résultats montrent que le 2-amino-octadécane-1 ,3-diol (A) et le 2-N-(2- hydroxy-hexadécanoyl)- amino-octadécane-1 ,3-diol (B) augmentent la viabilité des kératinocytes en culture, alors que la N-paimitoylsphingénine (C16H) a un effet cyto-toxique sur les cellules en culture.The results show that 2-amino-octadecane-1, 3-diol (A) and 2-N- (2-hydroxy-hexadecanoyl) - amino-octadecane-1, 3-diol (B) increase the viability of keratinocytes in culture, while N-paimitoylsphingenine (C16H) has a cytotoxic effect on cells in culture.
Exemple 3 : Mesure de l'effet du 2-amino-octadécane-1 ,3-diol et de ses dérivés sur le cycle cellulaire :Example 3: Measurement of the effect of 2-amino-octadecane-1, 3-diol and its derivatives on the cell cycle:
Des cellules HaCat sont cultivées comme précédemment.HaCat cells are cultured as before.
Elles sont ensuite ensemencées à la densité de 20000 cellules par puits, dans les 24 puits de plaques du type multipuits (Costar, France).They are then seeded at a density of 20,000 cells per well, in the 24 wells of multi-well plates (Costar, France).
24 heures après ensemencement, les cellules sont mises en contact avec les différents composés testés dans un milieu KBM (société Clonetics) contenant de l'insuline à 5 μg/ml et de l'hydrocortisone à 0,5 μg/ml et du 5-bromo-2' deoxyuridine (BrdU) à 1μ.M La phase du cycle cellulaire est évaluée 48 heures plus tard par la mesure de l'incorporation de BrdU dans l'acide désoxyribonucléïque génomique. Celle-ci est réalisée à l'aide d'un kit "BrdU fast", vendu par la société Boehringer et selon les prescriptions du fournisseur.24 hours after inoculation, the cells are brought into contact with the various compounds tested in a KBM medium (Clonetics company) containing insulin at 5 μg / ml and hydrocortisone at 0.5 μg / ml and 5- bromo-2 'deoxyuridine (BrdU) at 1μ.M The cell cycle phase is evaluated 48 hours later by measuring the incorporation of BrdU in genomic deoxyribonucleic acid. This is carried out using a "BrdU fast" kit, sold by the company Boehringer and according to the supplier's instructions.
Les composés A, et B de l'exemple précédent ont été testés à la concentration de 50 nM.Compounds A and B of the previous example were tested at a concentration of 50 nM.
Les résultats exprimés en pourcentage représentent l'augmentation du nombre de cellules entrées en phase S par rapport au contrôle, c'est à dire par rapport à une culture effectuée dans les mêmes conditions en l'absence de composés alcane-diol.The results expressed as a percentage represent the increase in the number of cells entered in phase S relative to the control, that is to say relative to a culture carried out under the same conditions in the absence of alkane-diol compounds.
72 heures 96 heures
Contrôle 0 072 hours 96 hours Control 0 0
A 36 41A 36 41
B 17 43B 17 43
Les résultats montrent que la 2-amino-octadécane-1 ,3-diol (A), et le 2-N-(2- hydroxy-hexadécanoyl)-amino-octadécane-1,3-diol (B) augmentent le nombre de kératinocytes entrés en phase S, indiquant ainsi une stimulation de l'activité mitotique cellulaire.The results show that 2-amino-octadecane-1, 3-diol (A), and 2-N- (2-hydroxy-hexadecanoyl) -amino-octadecane-1,3-diol (B) increase the number of keratinocytes entered into phase S, thus indicating a stimulation of cellular mitotic activity.
Exemple 4 : Effet du 2-amino-octadécane-1 ,3-diol et de ses dérivés sur la viabilité cellulaire en présence d'un composé à base sphingénine la N-acétyl sphingénine.Example 4 Effect of 2-amino-octadecane-1, 3-diol and its derivatives on cell viability in the presence of a sphingenine-based compound, N-acetyl sphingenine.
Des cellules HaCat sont cultivées comme dans l'exemple 2.HaCat cells are cultured as in Example 2.
24 heures après ensemencement, les cellules sont mises en contact avec les différents composés testés dans un milieu KBM (société Clonetics) contenant de l'insuline à 5 μg/ml et de l'hydrocortisone à 0,5 μg/ml.24 hours after seeding, the cells are brought into contact with the various compounds tested in a KBM medium (Clonetics company) containing insulin at 5 μg / ml and hydrocortisone at 0.5 μg / ml.
Les cellules sont cultivées en présence du 2-amino-octadécane-1 ,3-diol à tester jusqu'à l'évaluation de la viabilité cellulaire.The cells are cultured in the presence of 2-amino-octadecane-1, 3-diol to be tested until the evaluation of cell viability.
La N-acétyl sphingénine à la concentration de 10μM est ajoutée au milieu de culture pendant 2 heures au début de l'expérience.N-acetyl sphingenine at a concentration of 10 μM is added to the culture medium for 2 hours at the start of the experiment.
La viabilité cellulaire est évaluée 48 heures plus tard par la mesure de la respiration mitochondriale. Celle-ci est réalisée à l'aide d'un kit XTT, vendu par la société Boehringer et selon les prescriptions du fournisseur.Cell viability is evaluated 48 hours later by measuring mitochondrial respiration. This is carried out using an XTT kit, sold by the company Boehringer and according to the supplier's instructions.
L'expérience a été réalisée avec les composés suivants à la concentration deThe experiment was carried out with the following compounds at the concentration of
50 nM :50 nM:
C : 2-amino-octadécane-1 ,3-diol,C: 2-amino-octadecane-1, 3-diol,
D : 2-N-(2-hydroxy-hexadécanoyl)-amino-octadécane-1 ,3-diol, en comparaison avec le milieu de culture sans alcane-diol et sans N-acétyl sphingénine (A), et avec un milieu ne contenant que de la N-acétyl sphingénineD: 2-N- (2-hydroxy-hexadecanoyl) -amino-octadecane-1, 3-diol, in comparison with the culture medium without alkane diol and without N-acetyl sphingenine (A), and with a medium not containing only N-acetyl sphingenine
(B).(B).
Les résultats exprimés en pourcentage représentent le nombre de cellules par rapport au contrôle (A), c'est à dire par rapport à une culture effectuée dans les mêmes conditions en l'absence de composés alcane-diol et de N-acétyl sphingénine.The results expressed as a percentage represent the number of cells relative to the control (A), that is to say relative to a culture carried out under the same conditions in the absence of alkane-diol compounds and of N-acetyl sphingenine.
A 100100
B 57B 57
C 72C 72
D 78D 78
La N-acétyl sphingénine entraîne une diminution de la viabilité cellulaire. La
„„,_,„, Λ N-acetyl sphingenine causes a decrease in cell viability. The „„, _, „, Λ
PCT/FR98/01755PCT / FR98 / 01755
présence dans le milieu de culture d'un 2-amino-octadécane-1 ,3-diol tend à contrer cet effet.presence in the culture medium of a 2-amino-octadecane-1, 3-diol tends to counter this effect.
Exemple 5 : Exemples de compositions à appliquer sur la peau. Ces compositions peuvent se préparer par simple mélange. Les pourcentages sont donnés en poids de matière active par rapport au poids total de la composition.Example 5: Examples of compositions to be applied to the skin. These compositions can be prepared by simple mixing. The percentages are given by weight of active material relative to the total weight of the composition.
Emulsion huile dans eau hydratante : Huile de germe de maïs 2 %Oil in hydrating water emulsion: Corn germ oil 2%
Monostéarate de glycérol 3 %Glycerol monostearate 3%
Polyéthylène glycol 400 3 %Polyethylene glycol 400 3%
Carbopol 491 ® commercialisé par la société GOODRICH H 0,2 %Carbopol 491 ® sold by the company GOODRICH H 0.2%
Myristate d'isopropyle 3 % N-octanoylamino-octadécane-1 ,3-diol 0,1 %Isopropyl myristate 3% N-octanoylamino-octadecane-1, 3-diol 0.1%
Alcool cétylique 3 %Cetyl alcohol 3%
Alcool stéarique 3 %Stearic alcohol 3%
NaOH 0,008 0 //oNaOH 0.008 0 // o
Propylène glycol 5 /o Conservateurs qsPropylene glycol 5 / o Preservatives qs
Eau qsp 100Water qs 100
Emulsion eau dans huile hydratante : Huile de vaseline 10 %Water in moisturizing oil emulsion: Vaseline oil 10%
Protegin X commercialisé par la société Goldschmidt 20 %Protegin X marketed by Goldschmidt 20%
Huile de tournesol 15 %Sunflower oil 15%
Composition aromatique 1 %Aromatic composition 1%
N-acétylamino-octadécane-1 ,3-diol 0,05 0 //o Sulfate de magnésium 0,5 %N-acetylamino-octadecane-1, 3-diol 0.05 0 // o Magnesium sulfate 0.5%
Glycérol 5 %Glycerol 5%
Cétrol HE commercialisé par la société Henkel 4 %Cétrol HE marketed by Henkel 4%
Conservateur qsConservative qs
Eau déminéralisée qsp100Demineralized water qsp100
Gel aqueuxAqueous gel
Carbopol 940 ® commercialisé par la société GOODRICH 0,6 0 //oCarbopol 940 ® marketed by the company GOODRICH 0.6 0 // o
Transcutol ® commercialisé par la société GATTEFOSSE 5 /oTranscutol ® marketed by GATTEFOSSE 5 / o
Triéthanolamine 0,3 0 //o Propylène glycol 3 0 //oTriethanolamine 0.3 0 // o Propylene glycol 3 0 // o
NaOH 0,007 /oNaOH 0.007 / o
N-octanoylamino-octadécane-1 ,3-diol 0,1 0 //oN-octanoylamino-octadecane-1, 3-diol 0.1 0 // o
Conservateur qsConservative qs
Eau qsp 100Water qs 100
Crème aux liposomes non ioniques
Carbopol 940 ® commercialisé par la société GOODRICH 0,2 % Transcutol ® commercialisé par la société GATTEFOSSE 3 % Triéthanolamine 0,2 % Polyglycéryl-3-cétyl éther 3,8 % β sitostérol 3,8 % Dicétyl phosphate 0,4 % NaOH 0,007 %Nonionic liposome cream Carbopol 940 ® marketed by the company GOODRICH 0.2% Transcutol ® marketed by the company GATTEFOSSE 3% Triethanolamine 0.2% Polyglyceryl-3-cetyl ether 3.8% β sitosterol 3.8% Diketyl phosphate 0.4% NaOH 0.007 %
N-acétylamino-octadécane-1 ,3-diol 0,15 % Huile de tournesol 35 % Parfum qs Conservateur qs Eau qsp100
N-acetylamino-octadecane-1, 3-diol 0.15% Sunflower oil 35% Perfume qs Preservative qs Water qsp100
Claims
1. Utilisation dans une composition cosmétique ou pour la préparation d'une composition pharmaceutique destinée à traiter les signes du vieillissement cutané, d'une quantité efficace d'au moins un composé de formule générale (I) :1. Use in a cosmetic composition or for the preparation of a pharmaceutical composition intended for treating the signs of skin aging, of an effective amount of at least one compound of general formula (I):
dans laquelle R-| représente un radical hydrocarboné linéaire ou ramifié, éventuellement hydroxylé, saturé ou insaturé, ayant de 4 à 28 atomes de carbone ; R2 représente un atome d'hydrogène ou le radicalin which R- | represents a linear or branched hydrocarbon radical, optionally hydroxylated, saturated or unsaturated, having from 4 to 28 carbon atoms; R2 represents a hydrogen atom or the radical
Υ R,Υ R,
OO
dans lequel R3 représente un radical hydrocarboné linéaire ou ramifié, saturé ou insaturé, ayant de 1 à 11 atomes de carbone ou un radical hydrocarboné linéaire ou ramifié, hydroxylé, saturé ou insaturé, ayant de 1 à 29 atomes de carbone, l'hydroxyle pouvant être estérifié par une chaîne acyle ayant de 2 à 30 atomes de carbone, linéaire ou ramifiée, saturée ou insaturée ;in which R3 represents a linear or branched, saturated or unsaturated hydrocarbon-based radical having from 1 to 11 carbon atoms or a linear or branched, hydroxylated, saturated or unsaturated hydrocarbon-based radical having from 1 to 29 carbon atoms, the hydroxyl being capable of be esterified by an acyl chain having from 2 to 30 carbon atoms, linear or branched, saturated or unsaturated;
X représente un atome d'hydrogène ou le radical OH ; ou d'au moins l'un de ses isomères optiques ou l'un des diasteréoisomères.X represents a hydrogen atom or the OH radical; or at least one of its optical isomers or one of the diastereoisomers.
2. Utilisation selon la revendication 1 , caractérisée par le fait que R-| représente un radical hydrocarboné présentant de 6 à 22 atomes de carbone.2. Use according to claim 1, characterized in that R- | represents a hydrocarbon radical having from 6 to 22 carbon atoms.
3. Utilisation selon l'une quelconque des revendications 1 ou 2, caractérisée par le fait que R-| représente un radical hydrocarboné saturé.3. Use according to any one of claims 1 or 2, characterized in that R- | represents a saturated hydrocarbon radical.
4. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que R^ représente un radical hydrocarboné présentant de 10 à 18 atomes de carbone.4. Use according to any one of the preceding claims, characterized in that R ^ represents a hydrocarbon radical having from 10 to 18 carbon atoms.
5. Utilisation selon l'une quelconque des revendications 1 à 4, caractérisée par le fait que R-j représente un radical hydrocarboné linéaire.5. Use according to any one of claims 1 to 4, characterized in that R-j represents a linear hydrocarbon radical.
6. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que R2 représente H6. Use according to any one of the preceding claims, characterized in that R2 represents H
7. Utilisation selon l'une quelconque des revendications 1 à 5, caractérisée par le fait que R2 représente un radical
et R3 représente un radical hydrocarboné linéaire ou ramifié, saturé ou insaturé, ayant de 1 à 9 atomes de carbone ou un radical hydrocarboné linéaire ou ramifié, hydroxylé, saturé ou insaturé, ayant de 1 à 21 atomes de carbone.7. Use according to any one of claims 1 to 5, characterized in that R2 represents a radical and R3 represents a linear or branched, saturated or unsaturated, hydrocarbon-based radical having from 1 to 9 carbon atoms or a linear or branched, hydroxylated, saturated or unsaturated, hydrocarbon-based radical having from 1 to 21 carbon atoms.
8. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que la quantité de composé de formule (I) est comprise entre 10" % et 20% en poids par rapport au poids de la composition.8. Use according to any one of the preceding claims, characterized in that the amount of compound of formula (I) is between 10 " % and 20% by weight relative to the weight of the composition.
9. Utilisation selon la revendication précédente, caractérisée par le fait que la quantité de composé de formule (I) est comprise entre 10"3% et 10% en poids par rapport au poids de la composition.9. Use according to the preceding claim, characterized in that the amount of compound of formula (I) is between 10 "3 % and 10% by weight relative to the weight of the composition.
10. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que le composé de formule (I) est choisi parmi :10. Use according to any one of the preceding claims, characterized in that the compound of formula (I) is chosen from:
- le 2-amino-octadécane-1 ,3-diol,- 2-amino-octadecane-1, 3-diol,
- le 2-N-acétylamino-octadécane-1 ,3-diol,- 2-N-acetylamino-octadecane-1, 3-diol,
- le 2-Noctanoylamino-octadécane-1 ,3-diol,- 2-Noctanoylamino-octadecane-1, 3-diol,
- le 2-N-(2-hydroxy-hexadécanoyl)-amino-octadécane-1 ,3-diol,- 2-N- (2-hydroxy-hexadecanoyl) -amino-octadecane-1, 3-diol,
- le 2-N-(2-hydroxy-docosanoyl)-amino-octadécane-1 ,3-diol,- 2-N- (2-hydroxy-docosanoyl) -amino-octadecane-1, 3-diol,
- le 2-amino-octadécane-1 ,3,4-triol,- 2-amino-octadecane-1, 3,4-triol,
- le 2-N-(2-hydroxy-hexadécanoyl)-amino-octadécane-1 ,3,4-triol- 2-N- (2-hydroxy-hexadecanoyl) -amino-octadecane-1, 3,4-triol
- le 2-N-hexanoylamino-octadécane-1,3-diol- 2-N-hexanoylamino-octadecane-1,3-diol
- le 2-N-octanoylamino-octadécane-1 ,3,4-triol.- 2-N-octanoylamino-octadecane-1, 3,4-triol.
11. Utilisation selon la revendication précédente, caractérisée par le fait que le composé de formule (I) est choisi parmi le 2-N-acétylamino-octadécane-1 ,3-diol et le 2-N-octanoylamino-octadécane-1 ,3-diol.11. Use according to the preceding claim, characterized in that the compound of formula (I) is chosen from 2-N-acetylamino-octadecane-1, 3-diol and 2-N-octanoylamino-octadecane-1, 3 -diol.
12. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait qu'elle est destinée à traiter les rides et/ou les ridules.12. Use according to any one of the preceding claims, characterized in that it is intended for treating wrinkles and / or fine lines.
13. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait qu'elle est destinée à traiter le jaunissement de la peau.13. Use according to any one of the preceding claims, characterized in that it is intended to treat yellowing of the skin.
14. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait qu'elle est destinée à traiter l'aspect parcheminé de la peau.14. Use according to any one of the preceding claims, characterized in that it is intended to treat the parchment appearance of the skin.
15. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait qu'elle est destinée à traiter les taches pigmentaires de la peau.15. Use according to any one of the preceding claims, characterized in that it is intended for treating pigmentary spots on the skin.
16. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait qu'elle est destinée à traiter les télangiectasies.
16. Use according to any one of the preceding claims, characterized in that it is intended to treat telangiectasias.
17. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait qu'elle est destinée à traiter la perte d'élasticité, de souplesse et/ou de fermeté de la peau.17. Use according to any one of the preceding claims, characterized in that it is intended to treat the loss of elasticity, flexibility and / or firmness of the skin.
18. Procédé de traitement cosmétique de la peau humaine, caractérisé par le fait qu'il consiste à appliquer sur au moins une partie de la peau du corps humain, une composition cosmétique comprenant une quantité efficace d'au moins un composé de formule (I) tel que défini dans l'une quelconque des revendications 1 à 11 , à laisser celle-ci en contact avec la peau, et éventuellement à rincer.
18. A method of cosmetic treatment of human skin, characterized in that it consists in applying to at least part of the skin of the human body, a cosmetic composition comprising an effective amount of at least one compound of formula (I ) as defined in any one of claims 1 to 11, to leave it in contact with the skin, and optionally to rinse.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9710142 | 1997-08-07 | ||
FR9710142A FR2767056A1 (en) | 1997-08-07 | 1997-08-07 | USE OF A 2-AMINO-ALKANE POLYOL AS AN AGENT FOR TREATING THE SIGNS OF SKIN AGING |
PCT/FR1998/001755 WO1999007337A1 (en) | 1997-08-07 | 1998-08-06 | Use of a 2-amino-alkane polyol as agent for treating skin ageing signs |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1001739A1 true EP1001739A1 (en) | 2000-05-24 |
Family
ID=9510133
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP98941554A Withdrawn EP1001739A1 (en) | 1997-08-07 | 1998-08-06 | Use of a 2-amino-alkane polyol as agent for treating skin ageing signs |
Country Status (6)
Country | Link |
---|---|
US (1) | US20020006420A1 (en) |
EP (1) | EP1001739A1 (en) |
JP (1) | JP2001513490A (en) |
CA (1) | CA2299171A1 (en) |
FR (1) | FR2767056A1 (en) |
WO (1) | WO1999007337A1 (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2799650B1 (en) | 1999-10-14 | 2001-12-07 | Oreal | PROCESS FOR LIMITING THE PENETRATION IN THE SKIN AND / OR KERATINIC FIBERS OF AN ACTIVE COSMETIC AND / OR PHARMACEUTICAL AGENT |
FR2811893B1 (en) * | 2000-07-18 | 2003-04-18 | Oreal | USE OF AT LEAST ONE EXTRACT OF AT LEAST ONE IRIDACEA IN A COMPOSITION FOR STIMULATING IMMUNE DEFENSES |
US6988268B2 (en) * | 2002-04-30 | 2006-01-17 | Microsoft Corporation | IO completion architecture for user-mode networking |
FR2855047B1 (en) * | 2003-05-19 | 2007-11-30 | Oreal | COMPOSITION COMPRISING A SPHINGOID BASE, AN ACTIVATOR OF THE 4-AND / OR 6-HYDROXYLASE PATHWAY AND A FATTY ACID, USE FOR ENHANCING THE BARRIER FUNCTION OF THE SKIN |
WO2007114484A1 (en) * | 2006-03-31 | 2007-10-11 | Kao Corporation | Softening detergent composition |
KR100823146B1 (en) | 2006-12-28 | 2008-04-22 | 재단법인 한국원자력의학원 | Novel phytosphingosine derivatives and their use for enhancing radiation therapy |
DE102011085497A1 (en) * | 2011-10-31 | 2013-05-02 | Evonik Industries Ag | Cosmetic formulation |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9124360D0 (en) * | 1991-11-15 | 1992-01-08 | Unilever Plc | Cosmetic compositions |
CA2137001C (en) * | 1992-06-19 | 1999-05-04 | Peter M. Elias | Lipids for epidermal moisturization and repair of barrier function |
GB9308103D0 (en) * | 1993-04-20 | 1993-06-02 | Unilever Plc | Cosmetic composition |
US5368857A (en) * | 1993-11-15 | 1994-11-29 | Elizabeth Arden Company, Division Of Conopco, Inc. | Ceramide cosmetic compositions |
GB9421185D0 (en) * | 1994-10-20 | 1994-12-07 | Unilever Plc | Personal car composition |
FR2728164B1 (en) * | 1994-12-14 | 1997-03-21 | Oreal | COSMETIC OR DERMATOLOGICAL COMPOSITION CONTAINING A MIXTURE OF CERAMIDS, ITS USE FOR HYDRATING THE SKIN |
FR2729079A1 (en) * | 1995-01-09 | 1996-07-12 | Sederma Sa | Cosmetic compsn contg synthetic ceramide and protease |
-
1997
- 1997-08-07 FR FR9710142A patent/FR2767056A1/en active Pending
-
1998
- 1998-08-06 JP JP2000506931A patent/JP2001513490A/en active Pending
- 1998-08-06 EP EP98941554A patent/EP1001739A1/en not_active Withdrawn
- 1998-08-06 US US09/485,191 patent/US20020006420A1/en not_active Abandoned
- 1998-08-06 WO PCT/FR1998/001755 patent/WO1999007337A1/en active Search and Examination
- 1998-08-06 CA CA002299171A patent/CA2299171A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO9907337A1 * |
Also Published As
Publication number | Publication date |
---|---|
JP2001513490A (en) | 2001-09-04 |
WO1999007337A1 (en) | 1999-02-18 |
CA2299171A1 (en) | 1999-02-18 |
FR2767056A1 (en) | 1999-02-12 |
US20020006420A1 (en) | 2002-01-17 |
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