WO2012117340A1 - Procédé pour le traitement cosmétique d'une rougeur de la peau - Google Patents

Procédé pour le traitement cosmétique d'une rougeur de la peau Download PDF

Info

Publication number
WO2012117340A1
WO2012117340A1 PCT/IB2012/050907 IB2012050907W WO2012117340A1 WO 2012117340 A1 WO2012117340 A1 WO 2012117340A1 IB 2012050907 W IB2012050907 W IB 2012050907W WO 2012117340 A1 WO2012117340 A1 WO 2012117340A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
skin
cosmetic
chosen
Prior art date
Application number
PCT/IB2012/050907
Other languages
English (en)
Inventor
Olivier DE LACHARRIÈRE
Christian Tran
Original Assignee
L'oreal
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by L'oreal filed Critical L'oreal
Publication of WO2012117340A1 publication Critical patent/WO2012117340A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/164—Amides, e.g. hydroxamic acids of a carboxylic acid with an aminoalcohol, e.g. ceramides
    • 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
    • A61K8/42—Amides
    • 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
    • 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
    • A61P17/10—Anti-acne agents
    • 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
    • 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

  • the present invention relates to the cosmetic treatment and the prevention of redness of the skin or of the scalp, in particular redness associated with exposure to solar radiation, or that occurs especially during procedures that have an aesthetic purpose such as peels. It also relates to the use of compounds from the group of ceramides, as a calmative. These compounds will also be of use for treating the signs of skin irritations.
  • the present invention additionally relates to a composition comprising a ceramide derivative and optionally at least one compound capable of causing irritation of the skin, mucous membranes and/or scalp, and also to a cosmetic or dermatological assembly.
  • the field of the invention thus relates to protecting the skin and/or its integuments against skin irritation or skin inflammation induced by a stress.
  • stress is understood to mean any stress of exogenous origin, such as a stress of chemical origin (e.g.: xenobiotics, irritant chemicals, etc.), of environmental origin (e.g.: temperature, climate, UV radiation, atmospheric pollution, especially heavy metals, gaseous pollutants such as sulphur dioxide, ozone and nitrogen oxides, oxidative stress, cigarette smoke, etc.), of mecanical origin (e.g.: friction on contact with a razor, etc.), of infectious origin (e.g.: allergen, antigen, etc.), and/or any stress of endogenous origin, such as disorders involving an irritation mechanism and/or hormonal mechanism adversely affecting the skin.
  • a stress of chemical origin e.g.: xenobiotics, irritant chemicals, etc.
  • environmental origin e.g.: temperature, climate, UV radiation, atmospheric pollution, especially heavy metals, gaseous pollutants such as sulphur dioxide, ozone and nitrogen oxides, oxidative stress, cigarette smoke, etc.
  • redness is understood to mean a pink to red, or even dark red, coloration of all or part of the skin of the body, scalp, mucous membranes or semi-mucous membranes. This manifestation, also referred to as erythema, may be a sign of a healthy complexion (pink cheeks), but it is sometimes undesirable. This is in particular the case when it is associated with other symptoms of a skin disorder such as rosacea, or couperose.
  • the skin reacts via a cutaneous reaction that aims to restore the disrupted homeostatic balance or to repair the damage caused. It implements a cascade of reactions that may give rise to the persistent irritant process, which is characterized mainly by irritation of the skin or an involution of the hair bulb and its matrix environment.
  • treating unless otherwise indicated, is understood to mean any action that aims to improve the comfort or the well-being of an individual; this term therefore covers preventing, attenuating or relieving and also curative treatment.
  • Peels are skin treatments intended to bring about signs of skin rejuvenation, such as reduction of wrinkles and increase in the radiance of the skin. These treatments are used in particular to treat facial skin, the decolletage and the back of the hands when these areas exhibit signs of photoageing such as pigmentary spots, wrinkles, loss of radiance, loss of texture, or loss of skin elasticity.
  • the treatments for aesthetic purposes under consideration according to the invention may more particularly be surface skin treatments or invasive treatments for aesthetic purposes.
  • surface skin treatment for aesthetic purposes means treatments liable to have an aggressive nature with regard to the epidermis and especially liable to cause skin irritation. They may especially be chemical peels and laser treatments.
  • the latest generation of lasers uses a system for transforming the laser beam into a multitude of spaced-out beams in order to produce on the skin spaced-out impacts, thus maintaining areas of unimpaired healthy skin between the affected areas.
  • laser treatment means any treatment for aesthetic purposes using a laser, including the physical peels described previously.
  • laser treatments examples include laser depilation; laser treatment of angiomas; laser treatment of redness, especially of erythrosis or couperose; laser treatment of lentigo, especially actinic lentigo; laser treatment of tattoos; or laser treatment of wrinkles. Peel procedures, in particular medico-surgical procedures, are quite harsh treatments for the skin. Generally, the harsher they are, the better the final aesthetic result.
  • Ceramides are important epidermal lipids, in particular in the stratum corneum. They play a key role in restoring the barrier function.
  • Application EP 1 962 788 describes the use of ceramides as depigmenting agents, after UV irradiation.
  • the compounds N-oleoyl dihydrosphingosine and N-2-hydroxypalmitoyl dihydrosphingosine have a similar action in a predictive test of incorporation of thiouracil.
  • one subject of the present invention is a cosmetic treatment method for reducing or preventing skin redness and/or the signs of cutaneous microcirculation, characterized in that an effective amount of at least one compound of formula I is applied to the skin:
  • denotes a C-
  • R 2 denotes a linear C13-C-19 hydrocarbon-based radical which may comprise one or more ethylenically unsaturated groups, especially one or two ethylenically unsaturated groups; the method may also be carried out by applying a composition containing the compound of formula I in a physiologically acceptable medium.
  • a compound of formula (I) may be used in combination with one or more other active agents, such as compounds chosen from wound-healing agents, depigmenting agents and hydroxylated acids.
  • the invention also relates to the use of at least one compound of formula I for the preparation of compositions intended for the treatment of solar erythemas, redness accompanying a burn, and erythemas associated with the use of peels or lasers.
  • the invention also relates to compositions comprising at least said compound of formula I, combined with at least one other calmative or compositions comprising at least said compound combined with at least one agent having a particular irritant side effect (e.g.: cosmetic active agents, dermatological active agents).
  • skin means any cutaneous surface of the body, including the skin and broadened to the scalp and to the mucous and semi-mucous membranes and the term “integuments” means the eyelashes, body hair, head hair and nails.
  • compositions combining at least one compound of formula I with one or more other active agents, especially chosen from agents that act on the microcirculation.
  • Active agents that act on the microcirculation may be chosen from flavonoids, ruscogenins, esculosides, escin extracted from horse chestnut, nicotinates, hesperidin methyl chalcone, lavender or rosemary essential oils, extracts of Ammi visnaga.
  • these active agents may vary to a large extent. Generally, these active agents are present at a concentration ranging from 0.01 % to 15% and preferably from 0.05% to 10% by weight relative to the total weight of the composition.
  • the compounds of formula I according to the invention may prevent or reduce the appearance of skin redness, whether or not it is caused by UV irradiation.
  • Skin redness may especially be induced by at least one condition chosen from rosacea, irritable or irritated skin, the action of UV radiation, chemical peels, dermabrasion and laser treatments, but also the redness associated with acne lesions or following insect stings.
  • the compounds of formula I according to the invention favour the reconstruction of a good quality epidermis after a lesion, especially after an injury or an excoriation.
  • This is an improvement and an acceleration of the re-epithelialization on skin for which the physical integrity is interrupted; this effect is different from a barrier effect observed during the application of ceramides by re-establishing the lipid content at the skin surface.
  • the ceramides of formula I bring about a faster healing (re-epithelization) (estimated by measuring the transepidermal water loss, or TEWL). Ceramides are known for being constituents of the skin barrier, but not for directly stimulating the proliferation of epidermal cells. The healing rate exhibits a significant difference compared to the placebo (same excipient without ceramide).
  • the method and the uses according to the invention will in particular be suitable for the treatment of redness caused by UV irradiation, in particular skin irradiation at an erythematous dose.
  • ceramides of class II such as the compounds of formula I, and in particular 2-OLEOYLAMINOOCTADECANE-1 ,3-DIOL
  • a ceramide such as hydroxy palmitoyl sphinganine, has no anti- erythematous activity after irradiation by UV radiation.
  • the compounds of formula I or the compositions containing them are thus of use for preventing or reducing skin redness following exposure to UV radiation, or for preventing or reducing the cutaneous signs associated with a cutaneous surface treatment chosen from chemical peels, dermabrasion and laser treatments.
  • the method according to the invention is cosmetic, as it aims to improve the appearance of an individual in good health; it has a purely aesthetic purpose, especially when it is combined with a cutaneous surface treatment for reducing the cutaneous signs of ageing, which corresponds to a physiological modification.
  • the compound of formula I or the composition containing it is applied to the skin after exposure to UV radiation.
  • One subject of the invention is especially a cosmetic method for improving the appearance of the skin of a subject in which, after a first step of invasive treatment for aesthetic purposes, a compound of formula I or a composition containing it is applied to the skin that has undergone the treatment.
  • the invasive treatment for aesthetic purposes will especially be chosen from chemical peels, dermabrasion and laser treatments.
  • the cosmetic method will especially be intended to prevent or reduce skin redness.
  • Compound I will be able to be applied to the skin immediately after the exposure of the skin to the condition capable of inducing skin redness, or after a period of between 2 minutes and 6 hours after this exposure. This application will then be able to be repeated for several days, especially for 1 to 15 days, and in particular for 1 to 8 days. It could be a daily application or a multiple daily application, especially in the evening before going to bed.
  • the compound of formula I - or the composition containing it - will be applied to skin after healing.
  • This embodiment will be especially advantageous for the treatment of acne marks, which may persist in subjects even though the acnes spots have disappeared, but that leave redness remaining for several months or several years.
  • compositions suitable for the implementation of the invention contain, for example, the compound of formula I at a concentration of from 0.001 % to 10% by weight relative to the total weight of the composition, especially from 0.1 % to 5%, or even less than or equal to 2% by weight relative to the total weight of the composition.
  • the invention also relates to the cosmetic use of at least one compound of formula I as a calmative; the compound of formula I will preferably be in a cosmetic composition containing a physiologically acceptable medium.
  • the compounds of formula I are more particularly of use for preventing or reducing a skin reaction induced by the action of chemicals, of compounds capable of causing a skin irritation or itch, or of a peel, the action of temperature, of climate, of UV radiation, of atmospheric pollution, or else the action of friction on the skin, mucous membrane or scalp.
  • the invention relates to the use of at least one compound of formula I, or of a composition containing it, for the treatment or prevention of dandruff conditions.
  • the compound(s) of formula I will advantageously be applied to the scalp, in order to prevent or reduce the cutaneous signs associated with dandruff conditions, and especially redness or irritation.
  • the compound of formula I will be able to be applied in combination with at least one compound chosen from wound-healing agents, antidandruff agents, depigmenting agents, desquamating agents such as hydroxy acids, and antipruritic agents such as crotamiton.
  • compositions according to the invention in particular calmatives.
  • said compound of formula (I) is used in the absence of an additional antimicrobial agent. In these particular embodiments, said compound of formula (I) is not combined with an additional antimicrobial agent.
  • the invention also relates to a combination product for simultaneous use, separate use or sequential use over time, comprising:
  • the invention also relates to a combination product for simultaneous use, separate use or sequential use over time, comprising:
  • said combination product may be exempt from desquamating agent.
  • said combination product may comprise a desquamating agent with the exception of a beta-hydroxy-acid compound.
  • said combination product may be exempt from beta-hydroxy-acid compound, or alternatively, may be exempt from beta-hydroxy-acid compound and alpha-hydroxy-acid compound.
  • Beta- hydroxy-acid compounds encompass compounds of formulae (A) and/or (B) disclosed somewhere else in the present specification.
  • Desquamating agents that are particularly suitable for the invention will be chosen from hydroxy acids, in particular alpha or beta hydroxy acids, especially salicylic acid and derivatives thereof, 5-n-octanoylsalicylic acid, jasmonic acid and derivatives thereof, in particular jasmonic acid (3-hydroxy-2-pentylcyclopentaneacetic acid) and the cosmetically acceptable salts thereof.
  • compositions (i) and (ii) may be packaged separately inside two compartments, formed either by two separate containers, or inside a single device.
  • single device is understood within the present invention to mean a device via which the two compartments are firmly attached to one another.
  • the present invention finally comprises an assembly, in particular a cosmetic or dermatological assembly, comprising two compositions in two separate containers or two separate parts of one and the same container, one of the compositions comprising at least one compound of formula I or phosphoryl derivatives thereof and the other composition comprising at least one compound chosen from wound-healing agents and depigmenting agents and, in some embodiments, the other composition may comprise desquamating agents, especially hydroxy acids.
  • Another subject of the invention is a compound of formula I, especially N-oleoyl dihydrosphingosine and/or derivatives thereof, for its use for the treatment of the signs of skin irritation reactions.
  • the invention also relates to the use of at least one compound of formula I, especially N- oleoyl dihydrosphingosine and/or derivatives thereof, for the preparation of a composition intended for the treatment of the signs of skin irritation reactions, in particular chosen from solar erythemas, redness of skin having acne lesions or following an insect sting, seborrhoeic dermatitis and rosacea. Wound-healing agents
  • wound-healing agents mention may especially be made of: sugar derivatives such as O-octanoyl-6-D-maltose and N-acetyl glucosamine, allantoine, urea, wheat germ oil, certain amino acids such as hydroxyproline, arginine, serine, glutamic acid, and also extracts of white lily (e.g.: Phytelene Lys 37EG 16295 from Indena), a yeast extract, such as the wound-healing agent LS 7225B from LS (Cognis), tamanu oil, Saccharomyces cerevisiae extract or Biodynes TRF from Arch Chemical, oat extracts, chitosan and derivatives, carrot extracts, Artemia extract or GP4G from Vincience, sodium acexamate, lavandin extracts, honey or propolis extracts, ximeninic acid and salts thereof, such as acido ximeninico from Indena, Rosa rug
  • wound-healing agents use will be made of tamanu oil, sodium acexamate, honey extracts, horsetail extracts and Helichrysum extracts, and mixtures thereof.
  • the compound of formula I or derivatives thereof will be combined with an agent chosen from ascorbic acid and derivatives thereof such as magnesium ascorbyl phosphate and ascorbyl glucoside, and/or madecassoside, and/or a tepescohuite extract, or a C-glycoside derivative, and/or mixtures thereof in any proportion.
  • ascorbic acid and derivatives thereof such as magnesium ascorbyl phosphate and ascorbyl glucoside, and/or madecassoside, and/or a tepescohuite extract, or a C-glycoside derivative, and/or mixtures thereof in any proportion.
  • C-glycoside derivative is understood in particular to mean the compounds described in application EP 1 345 919 and that favour the synthesis of GAGs.
  • R' represents a saturated linear Ci to C 2 o, preferably Ci to Ci 0 , alkyl radical, or an unsaturated linear C 2 to C 2 o, preferably C 2 to Ci 0 , alkyl radical, or a saturated or unsaturated, branched or cyclic C 3 to C 20 , preferably C 3 to Ci 0 , alkyl radical, which is optionally substituted as described previously;
  • S represents a monosaccharide, in particular D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, more particularly D-xylose;
  • X represents a group chosen from -CO-, -CH(OH)-, -CH(NR' 1 R' 2 )- or -CH(R')-, as described previously.
  • R' represents a saturated linear Ci to C 4 , preferably Ci to C 3 , alkyl radical, optionally substituted with -OH, -COOH or -COORV, RV being a saturated linear Ci to C 4 alkyl radical, especially the ethyl radical;
  • S represents a monosaccharide, as described previously.
  • X represents a group chosen from -CO-, -CH(OH)-, -CH(NH 2 )-, and more particularly a - CH(OH)- group.
  • R' represents an unsubstituted saturated linear Ci to C 4 , preferably Ci to C 2 , alkyl radical, in particular the ethyl radical.
  • the C-glycoside derivative may be C-a-D- xylopyranoside-2-hydroxypropane that is in the form of a solution containing 30% by weight of active material in a water/propylene glycol (60/40 wt%) mixture.
  • These compounds act directly on the desquamation by favouring exfoliation, such as alpha hydroxy acids and beta hydroxy acids, polyhydroxy monocarboxylic acids, polyhydroxy bicarboxylic acids, polyhydroxy tricarboxylic acids; and (3-hydroxy-2-pentylcyclopentyl)acetic acid.
  • the preferred ⁇ -hydroxy acids are chosen from: salicylic acid and derivatives thereof, in particular 5-n-octanoylsalicylic acid.
  • the desquamating agent likely to be present in the composition according to the invention is chosen from salicylic acid and its derivatives such as 5-n-octanoylsalicylic acid (or capryloylsalicylic acid), 5-n- decanoylsalicylic acid, 5-n-dodecanoylsalicylic acid, 5-n-heptyloxysalicylic acid and their corresponding salts, resulting from a mineral or organic base.
  • salicylic acid and its derivatives such as 5-n-octanoylsalicylic acid (or capryloylsalicylic acid), 5-n- decanoylsalicylic acid, 5-n-dodecanoylsalicylic acid, 5-n-heptyloxysalicylic acid and their corresponding salts, resulting from a mineral or organic base.
  • the salts of the compounds may be obtained by salification with a mineral or organic base.
  • mineral bases examples include alkali metal or alkaline-earth metal hydroxides, for instance sodium hydroxide or potassium hydroxide, or aqueous ammonia.
  • organic bases that may be mentioned are amines and alkanolamines. Quaternary salts, for instance those described in patent FR 2 607 498, are particularly advantageous.
  • Salicylic acid or the salicylic acid compound as described previously may be present in the composition according to the invention in a content ranging from 0.05% to 10% by weight, preferably ranging from 0.05% to 5% by weight and preferentially ranging from 1 % to 4% by weight relative to the total weight of the composition.
  • the desquamating agent is chosen from those described in patent applications FR 2 581 542, WO 98/35973, FR 2 759 370, FR 2 762 839 or EP 0 875 495.
  • the desquamating agent present in the composition according to the invention is chosen from jasmonic acid and derivatives thereof and especially:
  • the amount of compound of formula (II) that can be used according to the invention may range, for example, from 0.01 % to 30%, preferably from 0.5% to 15% and especially from 1 % to 5% by weight relative to the total weight of the composition.
  • compound of formula (I) is not combined with a desquamating agent.
  • compound of formula (I) may be combined with at least a desquamating agent with the exception of a beta-hydroxy-acid compound, for example with the exception of a beta- hydroxy-acid compound of formula (A) and/or (B).
  • R10 and R20 identicals or differents, represent an hydrogen atom, or a linear or branched alkyl group comprising from 1 to 5 carbon atoms, or a phenyl group, or R10 and R20 form together a 5 or 6-membered cycle, and R is an hydrogen atom, an alkyl group of 1 to 12 carbon atoms, a silyl-alkyl group, an ammonium group or an alkaline or alkaline-earth metal.
  • concentration of the various active agents will be adapted by a person skilled in the art but could vary, for example, within proportions ranging from 0.01 % to 15% by weight, preferably ranging from 0.1 % to 10% by weight, relative to the total weight of the composition.
  • a composition according to the invention may be a composition suitable for a cosmetic or pharmaceutical, particularly dermatological, application.
  • this composition according to the invention is intended for a cosmetic application. It is formulated in a physiologically acceptable medium.
  • the physiologically acceptable medium is preferentially a cosmetically or dermatologically acceptable medium, i.e. a medium that has no unpleasant odour, colour or appearance, and that does not cause the user any unacceptable stinging, tautness or redness.
  • physiologically acceptable medium means a medium that is compatible with human keratin materials such as the skin, mucous membranes, scalp and/or hair.
  • compositions are in a form suitable for external topical application to the keratin materials.
  • This composition may be in any galenic form normally used in the cosmetic or pharmaceutical field, and especially in the form of an optionally gelled, aqueous or aqueous- alcoholic solution, of an optionally two-phase lotion-type dispersion, of an oil-in-water or water-in-oil emulsion or multiple (W/O/W or 0/W/O for example) emulsion, of an aqueous gel, of a dispersion of oil in an aqueous phase using spherules, it being possible for these spherules to be polymeric nanoparticles such as nanospheres and nanocapsules or, better still, lipid vesicles of ionic and/or nonionic type; or of an aqueous or oily gel.
  • These compositions are prepared according to the usual methods.
  • a composition in the form of an emulsion, especially an oil-in-water emulsion is preferably used.
  • the composition may be more or less fluid and may have the appearance of a white or coloured cream, an ointment, a milk, a lotion, a serum, a paste, a gel or a mousse. It may optionally be applied in aerosol form. It may also be in solid form, in particular in stick form.
  • the proportion of the fatty phase may range from 5% to 80% by weight and preferably from 8% to 50% by weight relative to the total weight of the composition.
  • the emulsifier and the coemulsifier may be present 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 invention also relates to a cosmetic assembly comprising: i) a container delimiting at least one compartment, said container being closed by a closing member; and ii) a composition as described previously, placed inside said compartment.
  • the container may be combined with an applicator.
  • the applicator may be in the form of a fine brush, as described, for example, in patent FR 2 722 380.
  • the product may be contained directly in the container, or indirectly.
  • the product may be arranged on an impregnated support, especially in the form of a wipe or a pad, and arranged (individually or in plurality) in a box or in a sachet.
  • an impregnated support especially in the form of a wipe or a pad, and arranged (individually or in plurality) in a box or in a sachet.
  • Such a support incorporating the product is described, for example, in patent application WO 01/03538.
  • the closing member may be coupled to the container by screwing.
  • Example 1 Effect of oleyl dihydrosphingosine on wound healing
  • the treatments were applied once a day for 15 days after the skin blister had been induced.
  • the volunteers were split into 3 groups, applied to which groups were, respectively, a cream containing 1 % of oleyl dihydrosphingosine (product according to the invention), a cream containing 1 % of hydroxy palmitoyl sphinganine, or the formulation base of identical composition but that contains no ceramide (placebo).
  • the recovery of the skin integrity was evaluated by measuring the transepidermal water loss, which decreases when the skin is repaired.
  • the barrier function was evaluated from the measurement of the TEWL (g/h/m 2 ), measured 3 times a day, every day from D1 to D15, and the average of the 3 measurements was calculated.
  • the measurement at DO was carried out before the lesion was induced by the skin blister, and constitutes the base value.
  • the D1 measurement was carried out just after the wound was induced.
  • the transepidermal water loss is significantly different from that of DO from D1 to D7 for the areas treated with oleyl dihydrosphingosine, and returns to normal on D8. For the areas that received no treatment or that received the placebo, the return to a base transepidermal water loss only takes place on D9.
  • Example 2 Effect of oleyl dihydrosphingosine on skin redness The study was conducted on a panel of 19 volunteers in good health aged from 19 to 49 years old. The subjects were all of between phototype III and phototype IV.
  • the areas of investigation (4 areas of the back) were exposed daily to UV rays for 4 consecutive days with doses of 0.75 MED (minimal erythemal dose).
  • the oleyl dihydrosphingosine was applied under occlusion, and after tape stripping of the areas of investigation, daily for 7 days before the first UV exposure, then daily on the irradiation days, after the exposures to UV rays.
  • the redness was evaluated by comparative clinical scoring, and by colorimetry
  • the erythema is measured just after the UV exposures and up to 24 h after the last irradiation. It is therefore observed that the oleyl dihydrosphingosine has a protective effect against the redness induced by repeated "tape-stripping" operations.
  • the oleyl dihydrosphingosine has an effect of preventing the appearance of an erythema during exposure to UV radiation, which is not the case for another ceramide, hydroxy palmitoyl sphinganine, or the placebo formulation.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un procédé de traitement cosmétique pour réduire ou empêcher une rougeur de la peau, caractérisé en ce qu'une quantité efficace d'au moins un composé de formule I est appliquée à la peau : R1-CHOH-CH(NH-COR2)(CH2OH) (I) dans laquelle R1 indique un radical alcoyle ou alcényle en C13 à C17, R2 indique un radical à base d'hydrocarbure, en C13-C19, linéaire, qui peut comprendre un ou plusieurs groupes à insaturation éthylénique, en particulier un ou deux groupes à insaturation éthylénique, ou une composition contenant le composé de formule I dans un milieu physiologiquement acceptable. L'invention concerne également l'utilisation cosmétique du composé comme calmant.
PCT/IB2012/050907 2011-03-01 2012-02-28 Procédé pour le traitement cosmétique d'une rougeur de la peau WO2012117340A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR1151669 2011-03-01
FR1151669A FR2972110B1 (fr) 2011-03-01 2011-03-01 Procede de traitement cosmetique des rougeurs cutanees
US201161449217P 2011-03-04 2011-03-04
US61/449,217 2011-03-04

Publications (1)

Publication Number Publication Date
WO2012117340A1 true WO2012117340A1 (fr) 2012-09-07

Family

ID=44548316

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2012/050907 WO2012117340A1 (fr) 2011-03-01 2012-02-28 Procédé pour le traitement cosmétique d'une rougeur de la peau

Country Status (2)

Country Link
FR (1) FR2972110B1 (fr)
WO (1) WO2012117340A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014167405A1 (fr) * 2013-04-11 2014-10-16 Montañez-Soto Flor Lucía Traitement d'ulcères des membres inférieurs au moyen de centella asiatica

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3005860B1 (fr) * 2013-05-21 2016-01-22 Oreal Compositions comprenant de l'huile d'ulkenia et leurs utilisations pour ameliorer et/ou renforcer la fonction barriere

Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2581542A1 (fr) 1985-05-07 1986-11-14 Oreal Compositions topiques destinees au traitement de la peau a base de derives de l'acide salicylique
FR2607498A1 (fr) 1986-12-01 1988-06-03 Oreal Nouveaux salicylates lipophiles d'ammoniums quaternaires, leur utilisation en cosmetique et en dermopharmacie
EP0378936A2 (fr) 1988-12-16 1990-07-25 L'oreal Utilisation de dérivés salicylés pour le traitement du vieillissement de la peau
EP0570230A1 (fr) 1992-05-15 1993-11-18 Shiseido Company Limited Préparation externe pour la peau
US5267407A (en) 1990-04-18 1993-12-07 Forjas Taurus S/A Safety device for semiautomatic pistol
FR2722380A1 (fr) 1994-07-12 1996-01-19 Oreal Applicateur pour l'application d'un produit cosmetique liquide et ensemble de maquillage muni d'un tel applicateur
US5558871A (en) 1994-01-10 1996-09-24 L'oreal Cosmetic and/or dermatological compositions containing salicylic acid
US5667789A (en) 1994-11-03 1997-09-16 L'oreal Salicylic acid derivative as a stabilizer for an oil-in-water emulsion
FR2759370A1 (fr) 1997-02-12 1998-08-14 Oreal Nouveaux derives de l'acide salicylique et leur utilisation dans les compositions cosmetiques ou dermatologiques
EP0875495A1 (fr) 1997-04-30 1998-11-04 L'oreal Nouveaux dérivés de l'acide salicylique et leur utilisation dans une composition cosmétique et/ou dermatologique
US6159479A (en) 1997-09-16 2000-12-12 L'oreal Hydrous salicylic acid solutions
WO2001003538A1 (fr) 1999-07-09 2001-01-18 Bourjois Article pour l'application d'une composition topique et son procede de preparation
WO2001070235A1 (fr) 2000-03-20 2001-09-27 Laboratoire D'evolution Dermatologique (L.E.D.) Composition a base de sphingolipide et de beta-hydroxy-acide pour les soins de la peau
EP1333022A2 (fr) 2002-02-04 2003-08-06 L'oreal Compositions comprenant des dérivés du cyclopentane, et utilisation pour favoriser la desquamation
EP1333021A2 (fr) 2002-02-04 2003-08-06 L'oreal Compositions comprenant des dérivés de l'acide jasmonique, et utilisation de ces dérivés pour favoriser la desquamation
EP1345919A2 (fr) 2000-12-22 2003-09-24 L'oreal Nouveau derives c-glycosides et utilisation
US20030215414A1 (en) * 1997-12-05 2003-11-20 Lambers Johannes Wilhelmus Jacobus Compositions comprising a combination of a free sphingoid base and a ceramide and uses thereof
EP1442737A2 (fr) 2003-01-31 2004-08-04 L'oreal Utilisation d'un dérivé d'acide (dihydro)jasmonique pour le traitement des peaux sèches
EP1502909A1 (fr) 2003-07-28 2005-02-02 L'oreal Utilisation d'un dérivé d'acide (dihydro)jasmonique comme agent desquamant
JP2005187398A (ja) 2003-12-25 2005-07-14 Kao Corp 毛髪化粧料
WO2007071875A2 (fr) * 2005-12-16 2007-06-28 L'oréal Utilisation de céramides pour dépigmenter la peau
FR2949968A1 (fr) * 2009-09-17 2011-03-18 Oreal Composition injectable comprenant une dispersion vesiculaire comprenant des ceramides et de l'acide hyaluronique, utilisation et procede

Patent Citations (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4767750A (en) 1985-05-07 1988-08-30 L'oreal Topical compositions intended for skin treatment containing salicylic acid derivatives
FR2581542A1 (fr) 1985-05-07 1986-11-14 Oreal Compositions topiques destinees au traitement de la peau a base de derives de l'acide salicylique
FR2607498A1 (fr) 1986-12-01 1988-06-03 Oreal Nouveaux salicylates lipophiles d'ammoniums quaternaires, leur utilisation en cosmetique et en dermopharmacie
EP0378936A2 (fr) 1988-12-16 1990-07-25 L'oreal Utilisation de dérivés salicylés pour le traitement du vieillissement de la peau
US5267407A (en) 1990-04-18 1993-12-07 Forjas Taurus S/A Safety device for semiautomatic pistol
US5580549A (en) 1992-05-15 1996-12-03 Shiseido Co., Ltd. External preparation for skin
EP0570230A1 (fr) 1992-05-15 1993-11-18 Shiseido Company Limited Préparation externe pour la peau
US5558871A (en) 1994-01-10 1996-09-24 L'oreal Cosmetic and/or dermatological compositions containing salicylic acid
FR2722380A1 (fr) 1994-07-12 1996-01-19 Oreal Applicateur pour l'application d'un produit cosmetique liquide et ensemble de maquillage muni d'un tel applicateur
US5667789A (en) 1994-11-03 1997-09-16 L'oreal Salicylic acid derivative as a stabilizer for an oil-in-water emulsion
FR2759370A1 (fr) 1997-02-12 1998-08-14 Oreal Nouveaux derives de l'acide salicylique et leur utilisation dans les compositions cosmetiques ou dermatologiques
WO1998035973A1 (fr) 1997-02-12 1998-08-20 L'oreal Nouveaux derives de l'acide salicylique et leur utilisation dans les compositions cosmetiques ou dermatologiques
EP0875495A1 (fr) 1997-04-30 1998-11-04 L'oreal Nouveaux dérivés de l'acide salicylique et leur utilisation dans une composition cosmétique et/ou dermatologique
FR2762839A1 (fr) 1997-04-30 1998-11-06 Oreal Nouveaux derives de l'acide salicylique et leur utilisation dans une composition cosmetique et/ou dermatologique
US6159479A (en) 1997-09-16 2000-12-12 L'oreal Hydrous salicylic acid solutions
US20030215414A1 (en) * 1997-12-05 2003-11-20 Lambers Johannes Wilhelmus Jacobus Compositions comprising a combination of a free sphingoid base and a ceramide and uses thereof
WO2001003538A1 (fr) 1999-07-09 2001-01-18 Bourjois Article pour l'application d'une composition topique et son procede de preparation
WO2001070235A1 (fr) 2000-03-20 2001-09-27 Laboratoire D'evolution Dermatologique (L.E.D.) Composition a base de sphingolipide et de beta-hydroxy-acide pour les soins de la peau
EP1345919A2 (fr) 2000-12-22 2003-09-24 L'oreal Nouveau derives c-glycosides et utilisation
EP1333022A2 (fr) 2002-02-04 2003-08-06 L'oreal Compositions comprenant des dérivés du cyclopentane, et utilisation pour favoriser la desquamation
EP1333021A2 (fr) 2002-02-04 2003-08-06 L'oreal Compositions comprenant des dérivés de l'acide jasmonique, et utilisation de ces dérivés pour favoriser la desquamation
FR2835525A1 (fr) 2002-02-04 2003-08-08 Oreal Nouveaux composes, compositions les comprenant et leur utilisation pour favoriser la desquamation
FR2835526A1 (fr) 2002-02-04 2003-08-08 Oreal Nouveaux composes, compositions les comprenant et leur utilisation pour favoriser la desquamation
EP1442737A2 (fr) 2003-01-31 2004-08-04 L'oreal Utilisation d'un dérivé d'acide (dihydro)jasmonique pour le traitement des peaux sèches
FR2850571A1 (fr) 2003-01-31 2004-08-06 Oreal Utilisation d'un derive d'acide(dihydro) jasmonique pour le traitement des peaux seches
EP1502909A1 (fr) 2003-07-28 2005-02-02 L'oreal Utilisation d'un dérivé d'acide (dihydro)jasmonique comme agent desquamant
FR2858320A1 (fr) 2003-07-28 2005-02-04 Oreal Utilisation d'un derive d'acide (dihydro)jasmonique comme agent desquamant.
JP2005187398A (ja) 2003-12-25 2005-07-14 Kao Corp 毛髪化粧料
WO2007071875A2 (fr) * 2005-12-16 2007-06-28 L'oréal Utilisation de céramides pour dépigmenter la peau
EP1962788A2 (fr) 2005-12-16 2008-09-03 L'Oréal Utilisation de céramides pour dépigmenter la peau
FR2949968A1 (fr) * 2009-09-17 2011-03-18 Oreal Composition injectable comprenant une dispersion vesiculaire comprenant des ceramides et de l'acide hyaluronique, utilisation et procede

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014167405A1 (fr) * 2013-04-11 2014-10-16 Montañez-Soto Flor Lucía Traitement d'ulcères des membres inférieurs au moyen de centella asiatica
US10232004B2 (en) 2013-04-11 2019-03-19 Flor Lucía MONTAÑEZ-SOTO Pharmaceutical composition based on Centella asiatica (Hydrocotyle asiatica L.) for the treatment of lower limb ulcers

Also Published As

Publication number Publication date
FR2972110B1 (fr) 2013-11-15
FR2972110A1 (fr) 2012-09-07

Similar Documents

Publication Publication Date Title
Loden et al. Hydrating substances
EP0801554B1 (fr) Formulations et procedes pour diminuer l'irritation de la peau
US4707354A (en) Mature skin treatment and protectant compositions and methods of using same
ES2198476T3 (es) Inhibidores de no-sintasa.
EP2144590B1 (fr) Compositions de traitement pour la peau et procédés
US20090306018A1 (en) Skin conditioner
US20080014162A1 (en) Method to treat skin in need of a calmative using at least one C-Glycoside derivative
MXPA97005954A (en) Formulations and methods to reduce irritation of the p
WO1996023490A1 (fr) Formulations et procedes permettant de reduire l'irritation cutanee
WO1996023490A9 (fr) Formulations et procedes permettant de reduire l'irritation cutanee
EP1549331B2 (fr) Utilisation de portulacée pour le traitement de rides du visage
US20090137534A1 (en) Skin treatment compositions and methods
US20050197407A1 (en) Method and preparation for reducing irritation and/or inflammatory reaction in human skin
Rathod et al. Cosmeceuticals and Beauty Care Products: Current trends with future prospects
US20180360712A1 (en) Cosmetic composition and use thereof
JP2014521671A (ja) 皮膚および毛髪の外観を改善するためのスフィンガニンの使用
JP2002363058A (ja) 敏感肌又は不耐性皮膚の許容限界を増大させるための少なくとも一のキレート剤を含む組成物の使用
US11918666B2 (en) Topical formulations comprising strontium and methylsulfonylmethane (MSM) and methods of treatment
WO2012117340A1 (fr) Procédé pour le traitement cosmétique d'une rougeur de la peau
US20230000759A1 (en) Ppar agonist complex and methods of use
KR101460900B1 (ko) 에피프리델라놀을 포함하는 피부 미백, 재생 또는 보습용 화장료 조성물
US20150352018A1 (en) Encoded particles compositions
WO2010013423A1 (fr) Préparation externe pour la peau, et agent de réparation des rides
Khana Skin Aging and Vesicular Delivery Systems
Axioti et al. Skin Aging and Vesicular Delivery Systems

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12707933

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 12707933

Country of ref document: EP

Kind code of ref document: A1