FR2947447A1 - Cosmetic treatment of visible and/or tactile irregularities of the skin, comprises applying topically a composition containing jasmonic acid compound in a medium on the skin, contacting the composition with the skin and rinsing - Google Patents

Abstract

Cosmetic treatment of visible and/or tactile irregularities of the skin, comprises: (a) applying topically on the skin a composition (A) containing at least more than 20 wt.% of a jasmonic acid compound (I) and their optical isomer or salt in a medium; (b) contacting the composition with the skin for a period of between 1 min and 6 hours; and (c) eliminating the composition by rinsing. Cosmetic treatment of visible and/or tactile irregularities of the skin, comprises: (a) applying topically on the skin a composition (A) containing at least more than 20 wt.% of a jasmonic acid compound of formula (I) and their optical isomer or salt in a medium; (b) contacting the composition with the skin for a period of between 1 min and 6 hours; and (c) eliminating the composition by rinsing. R 1>COOR 3>, preferably COOH, -COOCH 3, -COO-CH 2-CH 3, -COOO-CH 2-CH(OH)-CH 2OH, -COOCH 2-CH 2-CH 2OH or -COOCH 2-CH(OH)-CH 3; R 3>H or 1-4C alkyl optionally substituted by one or more OH; and R 2>optionally saturated linear 1-18C or branched or cyclic 3-18C hydrocarbon group. An independent claim is included for the composition comprising (I) (20-50 wt.%) in a medium. [Image] ACTIVITY : Antiseborrheic; Dermatological. MECHANISM OF ACTION : None given.

Description

The present invention relates to a peeling process which uses a composition containing, in a physiologically acceptable medium, at least 20% by weight of a compound derived from jasmonic acid.

Peelings are a well-known way to improve the surface appearance of the skin, especially to reduce pigmentation defects such as actinic lentigo or acne or chicken pox marks, or to smooth out irregularities in the texture of the skin. the skin, especially wrinkles and fine lines.

They have the effect of removing part of the skin to be treated (epidermis and possibly superficial layer of the dermis), by chemical methods (glycolic acid or salicylic acid, in particular).

Although the compositions used up to now for carrying out chemical peels have been able to give satisfactory results, the fact remains that they are not devoid of side effects. Thus, salicylic acid peels may give rise to salicylism in case of overdose or prolonged application.

There remains the need to have peeling compositions that are effective while being well tolerated.

However, it has been found by the Applicant that compositions comprising at least 20% by weight of a compound derived from jasmonic acid as defined below were useful for this purpose.

Compounds derived from jasmonic acid are described in application EP-1333021 for their action to promote desquamation of the skin

There is therefore no suggestion in the prior art that compounds derived from jasmonic acid could be used in high concentration for the production of chemical peels for cosmetic purposes.

The subject of the invention is therefore a method for cosmetic treatment of visible and / or tactile irregularities of the skin, comprising the steps of: (a) topically applying to the skin a composition containing, in a physiologically acceptable medium, at least 20 % by weight a compound derived from jasmonic acid as described below, (b) leaving the composition in contact with the skin for a period of between 1 minute and 6 hours, preferably between 1 minute and 30 minutes, and (c) removing the composition by rinsing. The compound derived from jasmonic acid used in the peeling process according to the invention is a compound chosen from those corresponding to the following formula (I): ## STR1 ## in which: R 1 represents a COOR 3 radical, R 3 denoting a hydrogen atom; hydrogen or a C1-C4 alkyl radical, optionally substituted with one or more hydroxyl groups; R2 represents a hydrocarbon radical, saturated or unsaturated, linear having 1 to 18 carbon atoms, or branched or cyclic having 3 to 18 carbon atoms; As well as their optical isomers, and corresponding salts. Preferably, R1 denotes a radical chosen from -000H, -COOMe, -000-CH2-CH3, -0000-CH2-CH (OH) -CH2OH, -COOCH2-CH2-CH2OH, -000CH2-CH (OH) -CH3 . Preferably, R1 denotes a -000H radical. Preferably, R2 denotes a hydrocarbon radical, linear, saturated or unsaturated, and preferably having from 2 to 6 carbon atoms. In particular, R3 may be a pentyl, pentenyl, hexyl or heptyl radical.

According to one embodiment, the compound of formula (I) is chosen from 3-hydroxy-2 - [(2Z) -2-pentenyl] -cyclopentane acetic acid or 3-hydroxy-2-pentyl acid (I Cyclopentane acetic acid, and preferably is 3-hydroxy-2-pentylcyclopentane acetic acid.

The salts of the compounds that may be used according to the invention are in particular chosen from alkali metal salts, for example sodium and potassium; alkaline earth metal salts, for example calcium, magnesium, strontium, metal salts, for example zinc, aluminum, manganese, copper; ammonium salts of formula NH4 +; quaternary ammonium salts; organic amine salts, such as, for example, the salts of methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2-hydroxyethylamine, bis (2-hydroxyethyl) amine, tri- (2- hydroxyethyl) amine; lysine salts, arginine. Salts chosen from sodium, potassium, calcium, magnesium, strontium, copper, manganese and zinc are preferably used.

The compounds of formula (I) are described in application EP-1333021. The composition used in the present invention contains an amount of compound derived jasmonic acid that depends on the depth of the peel to be performed, that is to say layers of the epidermis or dermis that must be removed, and for example an amount ranging from 21 to 50% by weight of compound derived from jasmonic acid, for example an amount of 21, 30, 40 or 50% by weight, relative to the total weight of the composition. The subject of the invention is thus also a composition comprising, in a cosmetically acceptable medium, at least one compound of formula (I) as previously described in a content greater than 20% and less than or equal to 50% by weight, relative to to the total weight of the composition. The composition according to the invention may be in any of the galenical forms conventionally used for topical application, provided that it is easily removed by rinsing, and in particular in the form of an aqueous gel, an aqueous or aqueous-alcoholic solution. It may also, by addition of a fatty or oily phase, be in the form of a dispersion of the lotion or emulsion type of liquid or semi-liquid consistency, preferably obtained by dispersion of a fatty phase in an aqueous phase ( HEY). These compositions are prepared according to the usual methods.

It can be applied by any means allowing a uniform distribution and especially using a cotton, a rod, a brush, a gauze, a spatula or a pad, or by spray, and can be removed by rinsing with water or a mild detergent. According to a preferred embodiment of the invention, the composition contains a continuous aqueous phase.

When the composition is in emulsion form, the proportion of the oily phase of the emulsion may range, for example, from 1 to 30% by weight, and preferably from 5 to 20% by weight relative to the total weight of the emulsion. composition. The oils, the emulsifiers and the co-emulsifiers used in the composition in emulsion form are chosen from those conventionally used in the cosmetic or dermatological field. The emulsifier and the co-emulsifier are generally 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 further contain lipid vesicles.

As fats usable in the invention can be used oils and in particular mineral oils (petroleum jelly), oils of vegetable origin (avocado oil, soybean oil), synthetic oils (perhydrosqualene) silicone oils (cyclomethicone) and fluorinated oils (perfluoropolyethers).

Emulsifiers and coemulsifiers for use in the invention include, for example, fatty acid esters of polyethylene glycol such as PEG-100 stearate, PEG-50 stearate and PEG-40 stearate; fatty acid esters of polyol such as glyceryl stearate, sorbitan tristearate and oxyethylenated sorbitan stearates available under the trade names Tween 20 or Tween 60, for example; and their mixtures. The composition according to the invention may also contain the usual adjuvants in the cosmetic and dermatological fields, such as thickeners, actives, preservatives, solvents, and fillers. The amounts of these various adjuvants are those conventionally used in the fields under consideration, and for example from 0.01 to 20% of the total weight of the composition. These adjuvants, depending on their nature, can be introduced into the fatty phase or into the aqueous phase. These adjuvants, as well as their concentrations, must be such that they do not adversely affect the keratolytic properties of the compound of formula (I). According to a preferred embodiment of the invention, the composition also contains at least one compound chosen from alcohols and polyols comprising from 1 to 3 carbon atoms. Examples of such compounds include ethanol, isopropanol, glycerol and propylene glycol. As indicated above, this composition is intended to be used in a peeling process aimed at attenuating the visible and / or tactile irregularities of the skin, and in particular at reducing the appearance of fine lines and / or wrinkles and / or or scars. The composition can therefore be applied to the face and / or the neck and / or the cleavage and / or the hands and / or the back.

To optimize its effects, the peeling method according to the invention preferably comprises additional steps of preparation of the skin for peeling and / or care of the skin after peeling using compositions containing lower amounts of compound. of formula (I) described above that the peel composition described above.

Thus, it is preferred that the method according to the invention comprises, in addition to the steps mentioned above: a preliminary step of applying to the skin a composition containing, in a physiologically acceptable medium, from 0.5 to 10% by weight; weight of compound of formula (I) described above, before the implementation of step (a), and / or - an additional step of application to the skin of a composition containing, in a physiologically acceptable medium, from 0.5 to 10% by weight of compound of formula (I) described above, after the implementation of step (c). The implementation of the preliminary step above also makes it possible to detect possible allergy to the compound of formula (I) and to improve the efficiency and homogeneity of the peel.

The compositions used in these preliminary and additional steps can be applied morning and evening, for example, optionally in combination with a composition for protecting the skin against the effects of UV. The pretreatment composition may be applied for one to four weeks and the post-treatment composition for one day to eight weeks, for example.

The method according to the invention, including any preliminary and additional steps, may be carried out once or repeated up to five times, if necessary, the peeling sessions being preferably spaced from one to eight weeks. The invention will now be illustrated by the following nonlimiting examples. In these examples, the amounts are indicated in weight percent. EXAMPLES Example 1: Effleurant efficiency test on Episkin The desquamating efficiency of the sodium salt of 3-hydroxy-2-pentylcyclopentane acetic acid on the one hand, and glycolic acid on the other hand, was measured. in solution at 25% by weight in a water / propylene glycol (70/30) mixture (Respectively solution A and solution B) Procedure Epiderms are reconstructed from keratinocytes in culture. They are received after 13 days of culture (J13), are placed on maintenance medium for 48 hours. On D15, a volume of 30 μl of test solution, solution A and solution B, tested separately, is spread topically on each epidermis. The contact time is 10 minutes. Each epidermis is then detached from its BPER (Biomaterial for Rebuilt Epidermis) and placed in an ependorf type (basal surface against the wall of the tube) in which a volume of 100 μl has been previously deposited. PBS (Phosphate Buffer Saline).

A series of 3 aspirations / repressions of PBS on the surface of the epidermis makes it possible to detach the corneocytes. The PBS containing the corneocytes is then transferred to a 96 well Millipore filter plate (filter pore diameter = 1.2 μm to retain corneocytes while removing debris). After aspiration of the PBS through the filters, 3 rinses are carried out (300 μl / well of PBS) The protein assay is then carried out using the BCA Bicinchoninic Acid assay kit (Pierce) .The following results are obtained: ml of proteins Solution A 176.44 73.7 Solution B 154.22 46.7 Placentbo 0 These results show that the sodium salt of 3-hydroxy-2-pentylcyclopentane acetic acid has an desquamating efficacy equivalent to that of Glycolic acid at 30% by weight (results not significantly different according to Anova statistical test / Bonferoni analysis) Example 2: Peeling composition Sodium salt of 3-hydroxy-2-pentyl-cyclopentane acetic acid at 30% in a water / dipropylene glycol mixture (70/30) 90% Preservative qs Purified water qs 100 This composition is intended to be applied to the face to smooth wrinkles and fine lines, according to the following method.

The skin is first cleaned and degreased, for example using gauze impregnated with ethanol or acetone, to remove sebum and dead cells and harmonize the cutaneous pH. The sensitive areas of the face (corner of the lips, wings of the nose, corner of the eyes) are then protected by an occlusive ointment and the eyes themselves by eye protection. The above composition is then applied to the skin, with the aid of a brush, in a thin layer. After a few minutes of exposure, the composition is removed by rinsing with a compress soaked in warm water. Example 3: Peeling Composition

Sodium salt of 3-hydroxy-2-pentyl-cyclopentane acetic acid at 30% in a water / dipropylene glycol mixture (70/30). 90% Preservative qs Purified water qs 100 This composition is prepared in a conventional manner for the skilled person. It is intended to be applied on the back to treat comedones, according to the method described in Example 1.

Claims (12)

REVENDICATIONS1. A method of cosmetic treatment of visible and / or tactile skin irregularities, comprising the steps of: (a) topically applying to the skin a composition comprising, in a physiologically acceptable medium, at least more than 20% by weight of a jasmonic acid compound, (b) leaving the composition in contact with the skin for a period of time between 1 minute and 6 hours, and (c) removing the composition by rinsing. said jasmonic acid compound being chosen from the compounds of formula (I) below: ## STR2 ## in which: R 1 represents a COOR 3 radical, R 3 denoting a hydrogen atom or a C 1 -C 4 alkyl radical, optionally substituted with one or several hydroxyl groups; R2 represents a hydrocarbon radical, saturated or unsaturated, linear having 1 to 18 carbon atoms, or branched or cyclic having 3 to 18 carbon atoms; As well as their optical isomers, and corresponding salts. 2. Method according to claim 1, characterized in that the compound (I) is such that R1 denotes a radical selected from -000H, -COOMe, -COO-CH2-CH3, -0000-0H2-CH (OH) - CH 2 OH, -COOCH 2 -CH 2 -CH 2 OH, -COOCH 2 -CH (OH) -CH 3; R2 denotes a hydrocarbon radical, linear, saturated or unsaturated, having from 2 to 6 carbon atoms. 3. Process according to any one of the preceding claims, characterized in that the compound (I) is 3-hydroxy-2-pentylcyclopentane acetic acid. (I) 30 4. Method according to any one of the preceding claims, characterized in that the composition is left in contact with the skin in step (b) for a period of between 1 min and 30 min. 5. Method according to any one of the preceding claims, characterized in that the composition contains from 21 to 50% by weight of compound of formula (I). 6. Process according to any one of the preceding claims, characterized in that the composition contains a continuous aqueous phase. 7. Process according to the preceding claim, characterized in that the composition also contains at least one compound chosen from alcohols and polyols comprising from 1 to 3 carbon atoms. 15 8. Method according to any one of the preceding claims, characterized in that it further comprises a preliminary step of application to the skin of a composition containing, in a physiologically acceptable medium, from 0.5 to 10% by weight. weight of compound of formula (I) as defined in one of claims 1 to 3, before the implementation of step (a). 20 9. Method according to any one of the preceding claims, characterized in that it further comprises an additional step of applying to the skin a composition containing, in a physiologically acceptable medium, from 0.5 to 10% by weight. weight of compound of formula (I) as defined in one of claims 1 to 3, after the implementation of step (c). 10. Method according to any one of the preceding claims, characterized in that it is intended to reduce wrinkles and fine lines and / or age spots and / or acne marks and / or to unclog the pores of the skin . 11. Method according to any one of the preceding claims, characterized in that the composition is applied to the face and / or the neck and / or the cleavage and / or the hands and / or the back. 30 12. Composition comprising, in a cosmetically acceptable medium, at least one compound of formula (I) as described in one of claims 1 to 3 in a content greater than 20% and less than or equal to 50% by weight, by relative to the total weight of the composition.5