Use of alkylamidothiazoles for cosmetic or dermatological care, treatment or prophylaxis of stretch marks on human skin

Abstract

The invention relates to the use of alkylamidothiazoles for cosmetic or dermatological care, treatment or prophylaxis of stretch marks on human skin.

Description

[0001] Description

[0002] Use of alkylamidothiazoles for cosmetic or dermatological care, treatment or prophylaxis of stretch marks on human skin

[0003] The present invention relates to a method for the prevention and / or cosmetic treatment of stretch marks on the skin and to the use of a composition for the manufacture of a dermatological preparation intended for the prevention and reduction of the visibility of stretch marks.

[0004] Stretch marks are visible features in the subcutaneous tissue (subcutis) that result from significant stretching of the tissue. In medical terminology, stretch marks are referred to as atrophic cutaneous stretch marks or distensive cutaneous stretch marks. During pregnancy, the appearance of stretch marks is physiological; they are referred to as stretch marks. The coloration of fresh stretch marks is caused by translucent blood vessels.

[0005] The stretch marks tend to appear on tissues subject to particularly high levels of stress, such as the abdomen, hips, buttocks, upper arms, and breasts. Predisposing factors include weak connective tissue, significant weight gain, and rapid growth. Furthermore, skin elasticity is reduced during pregnancy due to hormonal influences. The connective tissue in the dermis, which is responsible for the skin's elasticity, consists of a network of collagen fibers. If the connective tissue is overstretched, this leads to irreparable tears in the subcutaneous tissue, resulting in externally visible bluish-reddish stretch marks. Over time, the stretch marks fade but may remain visible as light-colored scars.

[0006] Stretch marks do not only occur during pregnancy, they can also appear during cortisone therapy or during growth.

[0007] It's also possible to get stretch marks from too much exercise. Likewise, stretch marks are almost inevitable when building muscle (like bodybuilding).

[0008] In addition, stretch marks can be symptoms of diseases, such as obesity or Cushing's syndrome, or they can occur as a side effect of medications, for example therapy with adrenocorticotropic hormone (ACTH) and glucocorticoids.

[0009] The treatment of stretch marks was described, for example, in the article by P. Zheng et al, "Anatomy of striae", British Journal of Dermatology 1 12: 185-193 (1985), which reports, among other things, that stretch marks are scars caused by an inflammatory process that destroys the elastic fibers.

[0010] Since then, various compounds, such as tretinoin (or al-I-trans-retinoic acid), have been proposed as active agents for the treatment of stretch marks. According to the article by REB Watson et al., "Fibrillin microfibrils are reduced in skin exhibiting striae distensae," British Journal of Dermatology 138: 931-937 (1998), it appears that tretinoin has an anti-stretch mark effect by restoring the network of fibrillins, which, compared to other components of the extracellular matrix, are the main constituent of the microfibrils contained in the elastic fibers. Although the current active ingredients allow for the regression of stretch marks, the results obtained are nevertheless not entirely satisfactory, especially considering the known problem of skin intolerance to tretinoin.There has therefore been a real need to develop a product that would allow the effective prevention and / or treatment of this complex and particularly unsightly phenomenon, stretch marks, with acceptable skin tolerance.

[0011] It has now been found, quite surprisingly and unexpectedly, that the use of one or more alkylamidothiazoles of the general formula at which

[0012] R 1 , R 2 , X and Y can be different, partially the same or completely the same and can mean independently of each other:

[0013] Ri = -Ci-C24-alkyl (linear and branched), -Ci-C24-alkenyl (linear and branched), -Ci-C8-cycloalkyl, -Ci-C8-cycloalkyl-alkylhydroxy, -C1-C24-alkylhydroxy (linear and branched), -C1-C24-alkylamine (linear and branched), -Ci-C24-alkylaryl (linear and branched), -Ci-C24-alkylaryl-alkyl-hydroxy (linear and branched), -C1-C24-alkylheteroaryl (linear and branched), -Ci-C24-alkyl-O-Ci-C24-alkyl (linear and branched), -C1-C24-alkyl-morpholino, -C1-C24-alkyl-piperidino, -C1-C24-alkyl-piperazino, -C1-C24 Alky-piperazino-N-alkyl means, R2 = H, -Ci-C24-alkyl (linear and branched), -Ci-C24-alkenyl (linear and branched), -Ci-C8-cycloalkyl, -Ci-C24-hydroxyalkyl (linear and branched), -Ci-C24-alkylaryl (linear and branched), -Ci-C24-alkylheteroaryl (linear and branched), means,

[0014] X = -H, -Ci-C24-alkyl (linear and branched), -Ci-C24-alkenyl (linear and branched), -Ci-C8-cycloalkyl, -Ci-C24-aryl (optionally mono- or polysubstituted with -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN), -Ci-C24-heteroaryl (optionally mono- or polysubstituted with -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN), -Ci-C24-alkylaryl (linear and branched), -Ci-C24-alkylheteroaryl (linear and branched), -aryl (optionally mono- or polysubstituted with -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN), -phenyl, -2,4-dihydroxyphenyl, -2,3-dihydroxyphenyl, -2,4-dimethoxyphenyl, -2,3-dimethoxyphenyl means,

[0015] Y = H, -Ci-C24-alkyl (linear and branched), -Ci-C24-alkenyl (linear and branched), -Ci-C8-cycloalkyl, -Ci-C24-aryl, -C1-C24-heteroaryl, -Ci-C24-alkylaryl (linear and branched), -Ci-C24-alkylheteroaryl (linear and branched), -aryl, -phenyl, -2,4-dihydroxyphenyl, -2,3-dihydroxyphenyl, -2,4-dimethoxyphenyl, -2,3-dimethoxyphenyl, -COO-alkyl, -COO-alkenyl, -COO-cycloalkyl, -COO-aryl, -COO-heteroaryl, and X, Y can optionally also = condensed aromatic, where X and Y are aromatic or aliphatic homo- or heterocyclic ring systems with up to n ring-forming atoms, and where the number n can assume values ​​from 5 to 8, and the respective ring systems can in turn be substituted with up to n - 1 alkyl groups, hydroxyl groups, carboxyl groups, amino groups, nitrile functions, sulfur-containing substituents, ester groups and / or ether groups, which may optionally be present in a suitable vehicle,for the cosmetic or dermatological care, prevention or treatment of stretch marks on the skin, characterized in that such an alkylamidothiazole or such alkylamidothiazoles are applied to the areas of the skin which are susceptible to the formation of stretch marks or which comprise them.

[0016] The present invention also relates to a cosmetic, non-therapeutic method for the care, prevention and / or treatment of stretch marks on the skin, characterized in that a composition comprising, in a suitable vehicle, at least one anti-stretch mark agent selected from the group consisting of alkylamidothiazoles of the formula defined above is applied to the areas of the skin susceptible to the formation of stretch marks or comprising them.

[0017] Preferred alkylamidothiazoles have the following structures:

[0018] Af-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)pivalamide

[0019] \ -(4-(2.4-dihydroxyphciiyl)thiazol-2-yl)isobiityramidc

[0020] A f -(4-(2,4-dihydroxyphenyl)thiazol-2-yl)butyramide

[0021] A A -(4-(2,4-dihydroxyphenyl)thiazol-2-yl)acetamide

[0022] 7V-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)-4-(hydroxymethyl)cyclohexanecarboxamide

[0023] Cosmetic or dermatological preparations containing alkylamidothiazoles, or their use for the treatment and / or prophylaxis of stretch marks on the skin, are also advantageous embodiments of the present invention. It is particularly advantageous if such preparations contain 0.000001 to 10 wt. %, in particular 0.0001 to 3 wt. %, very particularly 0.001 to 1 wt. %, of one or more of the alkylamidothiazoles used according to the invention, based on the total weight of the preparation.

[0024] It is of great advantage in the sense of the present invention if the preparations have values ​​between 6 and 9, preferably between 6.5 and 8, in particular between 6.8 and 7.3.

[0025] Cosmetic and dermatological preparations according to the invention can be in various forms. For example, they can be a solution, an anhydrous preparation, an emulsion or microemulsion of the water-in-oil (W / O) or oil-in-water (O / W) type, a multiple emulsion, for example of the water-in-oil-in-water (W / O / W) type, a gel, a solid stick, an ointment, or even an aerosol. It is also advantageous according to the invention to administer the substances used according to the invention and / or their derivatives in encapsulated form, e.g., in collagen matrices and other conventional encapsulation materials, e.g., as cellulose encapsulations, in gelatin, or liposomally encapsulated.

[0026] It is also possible and advantageous within the meaning of the present invention to incorporate the substances used according to the invention and / or their derivatives into aqueous systems or surfactant preparations for cleansing the skin and hair.

[0027] The cosmetic and dermatological preparations according to the invention may contain cosmetic auxiliaries as are customarily used in such preparations, e.g. preservatives, bactericides, perfumes, substances for preventing foaming, dyes, pigments which have a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or humectant substances, fats, oils, waxes or other customary components of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.

[0028] The lipid phase can advantageously be selected from the following group of substances: mineral oils,

[0029] Oils such as triglycerides of capric or caprylic acid, and natural oils such as castor oil;

[0030] Fats, waxes and other natural and synthetic fatty substances, preferably esters of fatty acids with low carbon alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with low carbon alkanoic acids or with fatty acids;

[0031] alkyl benzoates;

[0032] Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixtures thereof.

[0033] The oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions within the meaning of the present invention is advantageously selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids with a chain length of 3 to 30 C atoms and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 C atoms, from the group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 C atoms.Such ester oils can then advantageously be selected from the group isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, 2-octyldodecyl palmitate, oleyl oleate, dibutyl adipate, propylheptyl caprylate, diisopropyl adipate, cetearyl isononanoate, oleyl erucate, erucyl oleate, erucyl erucate as well as synthetic, semi-synthetic and natural mixtures of such esters, e.g. jojoba oil.

[0034] The aqueous phase of the preparations according to the invention optionally advantageously contains humectants such as propylene glycol, panthenol or hyaluronic acid, individually or in combination.

[0035] In particular, mixtures of the above-mentioned solvents are used. In the case of alcoholic solvents, water may be an additional component.

[0036] Emulsions according to the invention are advantageous and contain, for example, the fats, oils, waxes and other fatty substances mentioned, as well as water and an emulsifier as is usually used for this type of formulation.

[0037] Gels according to the invention usually contain low carbon alcohols, e.g. ethanol, propylene glycol, and water or an above-mentioned oil in the presence of a thickener.

[0038] Suitable propellants for preparations according to the invention that can be sprayed from aerosol containers are the usual, readily volatile, liquefied propellants, for example, hydrocarbons (propane, butane, isobutane), which can be used alone or in mixtures with one another. Compressed air can also be used advantageously.

[0039] Advantageously, preparations according to the invention can also contain substances which absorb UV radiation in the UVB range, the total amount of filter substances being, for example, 0.1 wt.% to 30 wt.%, preferably 0.5 to

[0040] 10 wt.%, in particular 1.0 to 6.0 wt.%, based on the total weight of the preparations, in order to provide cosmetic preparations which protect the hair or skin from the entire range of ultraviolet radiation. They can also be used as sunscreens for the hair or skin. Furthermore, preparations according to the invention can advantageously additionally contain substances which mask any unpleasant inherent odor of the other raw materials used, the total amount of perfume ingredients being, for example, 0.001 wt.% to 30 wt.%, preferably 0.05 to 10 wt.%, in particular 0.1 to 5.0 wt.%, based on the total weight of the preparations, in order to provide cosmetic preparations.

[0041] impact study;

[0042] A study was conducted on 160 subjects (i.e., exclusively female subjects) aged 20-50, phototypes I to VI, all of whom were consumers of skin care products. 50% of the subjects had stretch marks on their inner / outer thighs and / or abdomen. An oil according to Example 4 was used.

[0043] Results: After 2 weeks of use, 80% of the volunteers found that the visibility of their stretch marks was noticeably reduced.

[0044] The following examples are intended to illustrate the present invention. All figures are percentages by weight based on the total weight of the compositions.

[0045]

Claims

Patent claims 1 . Use of one or more alkylamidothiazoles of the general formula at which R 1 , R 2 , X and Y can be different, partially the same or completely the same and can mean independently of each other: Ri = -Ci-C24-alkyl (linear and branched), -Ci-C24-alkenyl (linear and branched), -Ci-C8-cycloalkyl, -Ci-C8-cycloalkyl-alkylhydroxy, -C1-C24-alkylhydroxy (linear and branched), -C1-C24-alkylamine (linear and branched), -Ci-C24-alkylaryl (linear and branched), -Ci-C24-alkylaryl-alkyl-hydroxy (linear and branched), -Ci-C24-alkylheteroaryl (linear and branched), -Ci-C24-alkyl-O-Ci-C24-alkyl (linear and branched), -C1-C24-alkyl-morpholino, -C1-C24-alkyl-piperidino, -C1-C24-alkyl-piperazino, -C1-C24 Alky-Piperazino-N-Alkyl means R2 = H, -Ci-C24-alkyl (linear and branched), -Ci-C24-alkenyl (linear and branched), -Ci-C5-cycloalkyl, -Ci-C24-hydroxyalkyl (linear and branched), -C1-C24-alkylaryl (linear and branched), -Ci-C24-alkylheteroaryl (linear and branched), X = -H, -Ci-C24-alkyl (linear and branched), -Ci-C24-alkenyl (linear and branched), -Ci-C8-cycloalkyl, -Ci-C24-aryl (optionally single or multiple substituted with -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN), -Ci-C24-heteroaryl (optionally mono- or polysubstituted with -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN), -Ci-C24-alkylaryl (linear and branched), -Ci-C24-alkylheteroaryl (linear and branched), -aryl (optionally mono- or polysubstituted with -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN), -phenyl, -2,4-dihydroxyphenyl, -2,3-dihydroxyphenyl, - 2,4-dimethoxyphenyl, -2,3-dimethoxyphenyl, Y = H, -Ci-C24-alkyl (linear and branched), -Ci-C24-alkenyl (linear and branched), -Ci-C5-cycloalkyl, -Ci-C24-aryl, -Ci-C24-heteroaryl, -Ci-C24-alkyl-aryl (linear and branched), -Ci-C24-alkylheteroaryl (linear and branched), -aryl, -phenyl, -2,4-dihydroxyphenyl, -2,3-dihydroxyphenyl, -2,4-dimethoxyphenyl, -2,3-dimethoxyphenyl, -COO-alkyl, -COO-alkenyl, -COO-cycloalkyl, -COO-aryl, -COO-heteroaryl, and X, Y can optionally also = condensed aromatic, where X and Y are aromatic or aliphatic homo- or heterocyclic ring systems with up to n ring-forming atoms, and where the number n can assume values ​​from 5 to 8, and the respective ring systems can in turn be substituted with up to n - 1 alkyl groups, hydroxyl groups, carboxyl groups, amino groups, nitrile functions, sulfur-containing substituents, ester groups and / or ether groups, that or which are optionally present in a suitable vehicle,for the cosmetic or dermatological care, prevention or treatment of stretch marks on the skin, characterized in that such an alkylamidothiazole or such alkylamidothiazoles are applied to the areas of the skin which are susceptible to the formation of stretch marks or which comprise them.

2. Cosmetic, non-therapeutic method for the care, prevention and / or treatment of stretch marks on the skin, characterized in that the areas of the skin susceptible to them are are liable to form or comprise stretch marks, applying a composition comprising, in a suitable vehicle, at least one anti-stretch mark agent selected from the group of alkylamidothiazoles of the formula defined in claim 1.

3. Use or method according to one of the preceding claims, characterized in that one or more alkylamidothiazoles are selected from the group of substances having the following structures: Af-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)pivalamide A -(4-(2,4-dihydroxyphenyl)thiazol-2-yl)isobutyramide A f -(4-(2,4-dihydroxyphenyl)thiazol-2-yl)butyramide A A -(4-(2,4-dihydroxyphenyl)thiazol-2-yl)acetamide 7V-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)-4-(hydroxymethyl)cyclohexanecarboxamide 4. Use or method according to one of the preceding claims, characterized in that preparations are used which contain 0.000001 to 10 wt.%, in particular 0.0001 to 3 wt.%, very particularly 0.001 to 1 wt.% of one or more of the used alkylamidothiazoles, based on the total weight of the preparation.

5. Use or method according to claim 4, characterized in that the preparations have values ​​between 6 and 9, preferably between 6.5 and 8, in particular between 6.8 and 7.

3.

6. Use or method according to one of the preceding claims, characterized in that cosmetic and dermatological preparations are a solution, an anhydrous preparation, an emulsion or microemulsion of the water-in-oil (W / O) or oil-in-water (O / W) type, a multiple emulsion, for example of the water-in-oil-in-water (W / O / W) type, a gel, a solid stick, an ointment or an aerosol.

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