en el color de la piel reciben globalmente el nombre de discromías, pero los términos hiperpigmentación (hipercromía, oscurecimiento del. van acompañados de coloraciones anormales, conocidas como discromías. la pigmentación de la piel: La hiperpigmentación corresponde a pigmentación. Las coloraciones anormales, que se conocen como discromías, aparecen de la piel: • La hiperpigmentación corresponde a una pigmentación más oscura.

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The present invention relates to the use of a cosmetic composition having depigmenting action or lightening skin, comprising, as active principle, at least one oxazoline. El color hipdrpigmentadas la piel se debe a varias sustancias: The skin color is due to several substances: This melanin is produced by the melanocytes in the basal layer, hiperpigmentavas the action of tyrosinase, copper and oxygen. Discromis skin melanin is constituted by a complex association of eumelanin and pheomelanin.

Its biosynthesis are common to dopaquinone double oxidation of tyrosine by tyrosinase enzyme cupro-protein. His path diverges later. Other tyrosine different enzymes involved in the genesis and control of melanins: Under the effect of exogenous or endogenous stimuli some modifications of skin color may appear: These modifications can settle in the epidermis and dermis or be due to a variation in the amount of melanin or melanocyte number.

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Melasma occurs most often in women using oral contraception or during pregnancy mask of pregnancy, chloasma. Mask of pregnancy or chloasma, appears in women who have an important percentage of female hormones and whose skin is exposed to the sun.

It affects mainly so pregnant women or women taking a contraceptive pill.

In the form of brown pigmented plaques, often symmetrical, more or less regular basis. Skin aging is also characterized by the appearance of pigment spots. This is known as solar lentigo for the most frequently photo-exposed areas face, hands, neckand senile lentigo, rather broad pigment spots, which appear in the subject of a certain age level of the hands, face and arms.

Depigmenting agents or lightening skin are chemical compounds capable of acting at the tissue, cell or subcellular scale. They act on the formation, transport, the color of melanin itself or on the viability of melanocytes melanocitotoxicidad. Furthermore, it is necessary to expose and remove the factor inducing hyperpigmentation before treating UV, perfume, estroprogestativo and advise a sunscreen maximum over protection type medical monitoring.

Finally, it is possible to remove the surface layers of corneocytes containing melanin, and thus perform a physical depigmentation of surface treatment on the other hand favors the penetration of depigmenting agents. Los motivos que empujan a decolorar la piel pueden ser diversos. The reasons that push discolor the skin may be different.

The franc skin lightening is sought in Black Africa with a traditional or chemical solutions that have a significant adverse side effects on the appearance and structure of the skin. Pale or white Asian face is obtained with molecules that act arbutin, kojic acid, ascorbic acid the lowest possible toxicity. Existe por lo tanto una necesidad para unas composiciones que presentan una actividad despigmentante o que aclaran la piel y que sean bien toleradas por la piel.

There is therefore a need for compositions having depigmenting activity or skin lightening and which are well tolerated by the skin. In the French patent application FR 2,, the inventors describe the use of oxazolines, allowing inhibition of migration of Langerhans cells.

In the French patent application FR 2,, the inventors describe the use of oxazolines to inhibit lipogenesis in human adipocytes few.

Surprisingly, we have now demonstrated that oxazolines also exhibit depigmenting action. Therefore, the invention relates to the use of at least one oxazoline, a depigmenting active principle, in a depigmenting composition.

Oxazolines according to the invention advantageously correspond to the following general formulas: According to an advantageous embodiment of the present invention, said oxazoline is an oxazoline of type 1 selected from the group consisting of 2-undecylhydroxymethylmethyl-1,3-oxazoline, 2-undecyl-44-dimethyl-1,3-oxazoline, E -4,4-dimethylheptadecenyl-1,3-oxazoline, 4-hydroxymethylmethylheptadecyl -1,3-oxazoline, E hydroxymethylmethylheptadecenyl-1,3-oxazoline, 2-undecylethylhydroxymethyl-1,3 oxazoline.


Advantageously, said oxazoline is 2-undecyl-4,4-dimethyl-1,3-oxazoline, called OX, of formula: Numerous synthetic routes are known for preparing oxazolines according to the invention. Thus, these can be prepared by chemical synthesis by reacting a fatty acid or methyl ester and an amino-alcohol, most often in the presence of an azeotropic agent in order to favor the elimination of the water formed and the methanol formed. Another possible route of synthesis consists of condensing a haloamide in the presence of a strong base or sodium carbonate RM Lusskin, J.

Oxazolines can also be synthesized by the reaction of epoxides nitriles, by reaction of thionyl chloride on hydroxyamides or also by the action of an acid on a aziridinilfosfina. The composition used according to the invention may contain other active agents having depigmenting action, causing a complementary or synergistic effect. Oxazolines can be associated with known depigmenting agents by the skilled artisan, such as hydroquinone and its derivatives, arbutin, retinoic acid, retinol, retinaldehyde, kojic acid, azelaic acid, vitamin B3 or PP, derivatives of resorcinol, resveratrol, extracts of licorice or white mulberry, alpha lipoic acid, linoleic acid, a chelating agents cations such as EDTA ethylene diamine tetra-acetic acidand the extracts soy.

Oxazolines can also be associated with some anti-oxidants, causing a complementary or synergistic effect. Examples of anti-oxidizing agents that may be mentioned in particular vitamin C, vitamin E, polyphenols in particular those extracted from green tea or grape or pineand sulfur derivatives.

The composition also advantageously comprises a mixture of vitamins vitamin C and E conferring anti-radical action and allows inhibiting nitrogen monoxide NO. Indeed, NO is involved in regulating pigmentation. This composition may be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, a foam or a gel.

Eventualmente, se puede aplicar sobre la piel en forma de aerosol.

Eventually, it can be applied to the skin in aerosol form. It may also be in solid form, for example in the form of a bar. Hiperpigmenttadas can also be applied by a patch. The composition according to the invention may also contain adjuvants that are common in the cosmetics field, such as stabilizers, preservatives, antioxidants, solvents, perfumes, dkscromias agents, odor absorbers, some chemical filters or minerals, a mineral pigments, surfactants, polymers, silicone oils and dyestuffs.

This cosmetic treatment method allows uniform the skin color. The composition is advantageously as defined above. The pigmentation may be without limitation spots of aging, a UV-induced spots or spots of phototoxicity perfume, medicament, exogenous toxic, burn or a chloasma.

The invention also relates to a method of cosmetic treatment for lightening the skin, characterized in that applied topically a composition comprising at least one oxazoline.

The depigmenting properties of oxazolines can, according to another aspect of the invention, lead to the use of at least one oxazoline as an active ingredient for the preparation of an active medicament as a depigmenting. The oxazoline used for drug preparation is advantageously as defined above. The following examples illustrate the present invention.

Discromiass 1 Example 1. Ejemplo 2 example 2. Ejemplo 3 example 3. Ejemplo 4 example 4. Ejemplo hiperpibmentadas example 5. Ejemplo 6 example 6. The analysis was performed on a panel of 21 adult female volunteers whose characteristics are presented in Table 1 below. All these volunteers had a pigmentation of lentigo type level hands, and also most at face level. Se ha verificado la homogeneidad de las varianzas discrromias la normalidad de las distribuciones en disfromias los casos.

Measurements are made at the level of the hands, in an area without any stain pigmentation.

The results correspond to averages and deviations from the mean – SEM These are indicated in Tables 2 and 3 below. The results of the effects of time and produced having a value less than 0. Measurements are made at the level of hand, in an area with pigmentation stain. The results correspond to the mean and deviations from the mean – SEM are indicated in Tables 4 and 5 below.


The results of the statistically significant after 6 weeks of application, some of the criteria evaluated variation are indicated in the following table 6: The percentages correspond to variations with respect to the initial evaluations, and the value of p corresponds to the probability p in relation to the initial evaluations Wilcoxon test, test bilateral meaning, significance: For measurements of intensity of the stain of pigment, the intensity of the stain is located previously.

The results of the statistically significant discromia 6 weeks of application, some of the hiperpigmdntadas evaluated variation are indicated in Table 7 below: Therefore, OX is an effective depigmenting active ingredient, dermatologically well accepted.

Ejemplo 7 example 7. We have studied the cosmetic depigmenting efficacy and skin compatibility clinic cosmetic hiperpigkentadas according to the invention in the field of melasma of the discromiax.


The product is used morning and evening level brown spots, after washing, dry skin. The skin of the tested people is protected from sunlight by applying full protection SPF During the study, no other depigmenting product on the areas concerned local cosmetic or drug use is applied.

These evaluations and measurements were carried out before using the product, and then after 60 days. This study shows the cosmetic depigmenting efficacy of the cosmetic formulation of Example 1 with depigmenting target, comparing the evolution of the different components of melasma. Cosmetological good acceptability and tolerance allergological formula hiperpigmentxdas been studied in parallel.

Volunteers entering the study, a total of 20, all female, were 20 to 61 years of age mean age In this study, we have only considered the hyperpigmented lesions hiperpigmenatdas face melasma and last for more than 6 months and less than 10 years evolution. El origen hormonal de las lesiones de melasma se encuentra de manera clara en 9 de los sujetos; Hormonal origin of melasma lesions is clearly in 9 subjects; es probable en 10 sujetos; It is hiperpitmentadas in 10 subjects; para 1 sujeto es probable un origen inflamatorio.

The calculation used has been simplified MASI, ie: The melanic index was calculated using the following equation: The melanic index was measured on the test zones to the right and left before any product use and after 60 days.

There have been a standard photographs, right profile and left profile at each stage of study.

There have been a UV photographs, right profile and left profile, at each stage of study and have been the subject of a computerized treatment of the distribution of colors.

They have served for the precise location of the hyperpigmented areas. It has made an assessment of the overall tolerance the D60 according to a severity scale of 4 levels. The D60, has given an opinion on the effectiveness of the product used depigmentation using the following scale: The D60 has been carried out a questionnaire on the subject in relation to the cosmetic qualities of the product tested. Psycho-sensory subjective assessment of cosmetic acceptability in regard to the product and its conditions of use have been made thanks to some questions raised in a questionnaire administered to each volunteer the D60 questionnaire.

It has been monitored the skin condition from the initial state observed during the study entry, by the dermatologist after 60 days of use of the tested product. Initially, the mean MASI calculations for all the volunteers analyzed is After 60 days of use, the average result is