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WO2025129541A1 - Combinaisons d'un ou plusieurs alkylamidothiazoles et de diméthylméthoxy chromanol, et préparations cosmétiques contenant de telles combinaisons - Google Patents

Combinaisons d'un ou plusieurs alkylamidothiazoles et de diméthylméthoxy chromanol, et préparations cosmétiques contenant de telles combinaisons Download PDF

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Publication number
WO2025129541A1
WO2025129541A1 PCT/CN2023/140489 CN2023140489W WO2025129541A1 WO 2025129541 A1 WO2025129541 A1 WO 2025129541A1 CN 2023140489 W CN2023140489 W CN 2023140489W WO 2025129541 A1 WO2025129541 A1 WO 2025129541A1
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WO
WIPO (PCT)
Prior art keywords
weight
preparations
cosmetic preparations
alkylamidothiazoles
cosmetic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/CN2023/140489
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English (en)
Inventor
Luan LUAN
Hanjun CHEN
Jie Zhou
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nivea Shanghai Co Ltd
Beiersdorf AG
Original Assignee
Nivea Shanghai Co Ltd
Beiersdorf AG
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 Nivea Shanghai Co Ltd, Beiersdorf AG filed Critical Nivea Shanghai Co Ltd
Priority to PCT/CN2023/140489 priority Critical patent/WO2025129541A1/fr
Priority to PCT/EP2024/085442 priority patent/WO2025131863A1/fr
Publication of WO2025129541A1 publication Critical patent/WO2025129541A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives

Definitions

  • cosmetic products not only serve to look beautiful and attractive, but with their effect they make a decisive contribution to increased self-esteem and the well-being of people. Accordingly, a wide variety of cosmetic products are used for the daily cleaning and care of human skin.
  • cosmetic preparations for the care of human skin are known from DE 102011083259 A1, which contain alkylamidothiazoles.
  • the alkylamidothiazoles used are used in the cosmetic preparations to combat and prevent undesired pigmentation of the skin. In this way, the user's complexion can be decisively improved.
  • alkylamidothiazoles can be used in cosmetic or dermatological preparations for the prophylaxis and treatment of sensitive skin, itching, dry skin and inflammatory symptoms of human skin.
  • the document discloses various cosmetic O/W emulsions for application to human skin.
  • DE 102013204110 A1 discloses a large number of cosmetic preparations for the care of human skin containing alkylamidothiazoles.
  • a particularly effective lightening of human skin is achieved by the combined use of alkylamidothiazoles with one or more cyclodextrins.
  • a disadvantage for example, is the fact that the color of newly produced cosmetic or dermatological preparations changes during storage. This occurs more intensely when the preparation is exposed to light.
  • Products are often selected based on their optical appearance or their skin. However, if the white appearance of a product deteriorates over the storage period, the consumer is usually annoyed because the decisive purchase criterion is no longer met.
  • the color stability of cosmetic or dermatological preparations can in principle be assessed by specially trained personnel who compare the color of a freshly prepared preparation (within 24 hours of preparation) and after a corresponding storage time.
  • the color change of the products are always very difficult to judge. It is, therefore, advantageous using a special instrument called Digi-Eye on the color change.
  • One object of the present invention was therefore to provide a way of preventing or minimizing degradation processes in cosmetic products in a particularly effective manner, so that color stability is ensured.
  • Astonishingly the combination of Dimethyl methoxy chromanol and 3-O-ethyl ascorbic acid acts in a synergistic way in comparison to the single substances to prevent or reduce the deterioration of alkylamidothiazoles caused by oxidative processes and/or heat and/or UV-light.
  • Dimethyl methoxy chromanol is a well known antioxidant. It is characterised by the chemical structure as follows:
  • Another embodiment of the present invention are and cosmetic preparations containing such combinations.
  • Yet another embodiment of the present invention is the method of use of
  • Advantageous embodiments of the present invention are also cosmetic or dermatological preparations with a content of such active ingredient combination, and the use thereof for lightening human skin.
  • preparations according to the invention comprise formulations, where the total amount of the one or more alkylamidothiazoles is e.g. 0.00001%by weight to 10%by weight, preferably 0.001%by weight-5%by weight, in particular 0.005%by weight-3%by weight, based on the total weight of the preparations, in order to provide cosmetic preparations.
  • preparations according to the invention comprise formulations, where the total amount of the Dimethyl methoxy chromanol is e.g. 0.00001%by weight to 10%by weight, preferably 0.001%by weight -5%by weight, in particular 0.005%by weight to 3%by weight, based on the total weight of the preparations, in order to provide cosmetic preparations.
  • preparations according to the invention comprise formulations, may additionally contain an active amount of ⁇ -tocopherol, preferably, if the total amount of the is e.g. 0.00001%by weight to 10%by weight, preferably 0.001%by weight -5%by weight, in particular 0.005%by weight to 3%by weight, based on the total weight of the preparations, in order to provide cosmetic preparations.
  • preparations according to the invention comprise formulations, may additionally contain an active amount of ⁇ -tocopherol, preferably, if the total amount of the is e.g. 0.00001%by weight to 10%by weight, preferably 0.001%by weight -5%by weight, in particular 0.005%by weight to 3%by weight, based on the total weight of the preparations, in order to provide cosmetic preparations.
  • preparations according to the invention comprise formulations, may additionally contain an active amount of dimethyl methoxy chromanol, preferably, if the total amount of the is e.g. 0.00001%by weight to 10%by weight, preferably 0.001%by weight -5%by weight, in particular 0.005%by weight to 3%by weight, based on the total weight of the preparations, in order to provide cosmetic preparations.
  • preparations according to the invention comprise formulations, may additionally contain an active amount of niacinamide, preferably, if the total amount of the is e.g. 0.00001%by weight to 10%by weight, preferably 0.001%by weight-5%by weight, in particular 0.005%by weight to 3%by weight, based on the total weight of the preparations, in order to provide cosmetic preparations.
  • Niacinamide or nicotinamide is a form of vitamin B 3 found in food and used as a dietary supplement and medication. [2] [3] [4] As a supplement, it is used by mouth to prevent and treat pellagra (niacin deficiency) Niacinamide is characterized by the structural formula as follows:
  • the preparation may comprise less than about 1.5%by weight of the one or more hydrocolloids, e.g., not more than about 1.0%by weight of the one or more hydrocolloids and/or at least about 0.1%by weight of the one or more hydrocolloids, based on the total weight of the preparation.
  • the one or more hydrocolloids may comprise one or more of
  • the one or more hydrocolloids may comprise one or more polyacrylates selected from carbopols of types 980, 981, 1382, 2984 and 5984 and carbomer ULTREZ.
  • the one or more hydrocolloids may comprise one or more of a polymethacrylate, an acrylate copolymer, an alkylacrylate copolymer, a polyacrylamide, an alkylacrylate crosspolymer, an acrylonitrogen copolymer and a polyacryloyldimethyltauramide.
  • the one or more hydrocolloids may compris one or more of agar agar, alginic acid, carrageen, gelatin, gum arabic, pectin and tragacanth and/or one or more of guar gum, locust bean flour, xanthan gum, polyvinyl alcohol, polyvinylpyrrolidone, propyleneglycol alginate and starch.
  • the one or more hydrocolloids may comprise an alkyl-modified cellulose derivative and/or an alkylhydroxycellulose, for example, at least one of methylcellulose, hydroxypropylmethylcellulose and hydroxyethylcellulose.
  • the preparation may comprise at least about 0.1%and/or not more than about 1.0%by weight of the one or more hydrocolloids.
  • the one or more hydrocolloids may comprise carbomer ULTREZ and/or at least one of agar agar, alginic acid, carrageen, gelatin, gum arabic, pectin and tragacanth and/or at least one of guar gum, locust bean flour, xanthan gum, gellan gum polyvinyl alcohol, polyvinylpyrrolidone, propyleneglycol alginate and starch and/or at least one of methylcellulose, hydroxypropylmethylcellulose and hydroxyethylcellulose.
  • Advantageous alkylamidothiazoles in the context of the present invention are substances of the general formula in which R1, R2, X and Y can be different, partly identical or completely identical and, independently of one another, can mean:
  • R1 -C1-C24-alkyl (linear and branched) , -C1-C24-alkenyl (linear and branched) , -C1-C8-cycloalkyl, -C1-C8-cycloalkyl-alkylhydroxy, -C1-C24-alkylhydroxy (linear and branched) , -C1-C24 alkylamine (linear and branched) , -C1-C24-alkylaryl (linear and branched) , -C1-C24-alkylaryl-alkyl-hydroxy (linear and branched) , -C1-C24-alkylheteroaryl (linear and branched) , -C1-C24-alkyl-O-C1-C24-alkyl (linear and branched) , -C1-C24 alky-morpholino, -C1-C24 alky- pipe
  • R2 H, -C1-C24-alkyl (linear and branched) , -C1-C24-alkenyl (linear and branched) , -C1-C8-cycloalkyl, -C1-C24-hydroxyalkyl (linear and branched) , -C1-C24-alkylaryl (linear and branched) , -C1-C24-alkylheteroaryl (linear and branched) ,
  • X -H, -C1-C24-alkyl (linear and branched) , -C1-C24-alkenyl (linear and branched) , -C1-C8-cycloalkyl, -C1-C24-aryl (optionally mono-or polysubstituted with -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN) , -C1-C24-heteroaryl (optionally mono-or polysubstituted with -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN) , -C1-C24-alkylaryl (linear and branched) , -C1-C24-alkylheteroaryl (linear and branched) , -aryl (optionally mono-or polysubstituted with -OH,
  • Said thiazoles can either be in the form of the free base or the salt: e.g. fluoride, chloride, bromide, iodide, sulfate, carbonate, ascorbate, acetate or phosphate.
  • halogen salts such as e.g. chloride and bromide.
  • treatment and/or prophylaxis of undesired skin pigmentation can be both in the cosmetic sphere and in the pharmaceutical sphere.
  • the pharmaceutical (or dermatological) treatment is primarily understood for diseased skin conditions, whereas the cosmetic treatment and/or prophylaxis of undesired skin pigmentation primarily relates to healthy skin.
  • X is selected from the group of substituted phenyls, in which case the substituents (Z) can be selected from the group -H, -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN, acetyl and can be identical or different.
  • X is selected from the group of phenyl groups substituted with one or more hydroxy groups, in which case the substituent (Z) can be selected from the group -H, -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN, acetyl, and preference is given to the following generic structure in which Y, R1 and R ⁇ 2 >can have the properties defined above.
  • R1 -C1-C24-alkyl (linear and branched) , -C1-C24-alkenyl (linear and branched) , -C1-C8-cycloalkyl, -C1-C8-cycloalkyl-alkylhydroxy, -C1-C24 alkylhydroxy (linear and branched) , -C1-C24 alkylamine (linear and branched) , -C1-C24-alkylaryl (linear and branched) , -C1-C24-alkylaryl-alkyl-hydroxy (linear and branched) , -C1-C24-alkylheteroaryl (linear and branched) , -C1-C24-alkyl-O-C1-C24-alkyl (linear and branched) , -C1-C24-alky-morpholino, -C1-C24 alky-pipe
  • R1 -C1-C24-alkyl (linear and branched) , -C1-C24-alkenyl (linear and branched) , -C1-C8-cycloalkyl, -C1-C8-cycloalkyl-alkylhydroxy, -C1-C24-alkylhydroxy (linear and branched) , -C1-C24 alkylamine (linear and branched) , -C1-C24-alkylaryl (linear and branched) , -C1-C24-alkyl-aryl-alkyl-hydroxy (linear and branched) , -C1-C24-alkylheteroaryl (linear and branched) , -C1-C24-alkyl-O-C1-C24-alkyl (linear and branched) , -C1-C24 alkyl-morpholino, -C1-C24 al
  • Cosmetic or dermatological preparations with a content of alkylamidothiazoles and their use for the treatment and/or prophylaxis of undesired skin pigmentation are likewise advantageous embodiments of the present invention.
  • such preparations comprise 0.000001 to 10%by weight, in particular 0.0001 to 3%by weight, very particularly 0.001 to 1%by weight, of one or more of the alkylamidothiazoles used according to the invention, based on the total weight of the preparation.
  • Cosmetic and dermatological preparations according to the invention can be in various forms. Thus, they can be e.g. a solution, an anhydrous preparation, an emulsion or micro-emulsion of the water-in-oil (W/O) type or of the oil-in-water (O/W) type, a multiple emulsions, for example of the water-in-oil-in-water (W/O/W) type, a gel, a solid stick, a balm or else 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 customary encapsulation materials, e.g. as cellulose encapsulations, in gelatin or liposomally encapsulated.
  • W/O water-in-oil
  • O/W oil-in-water
  • a multiple emulsions for example of the water-in-oil-in-water (W/O/
  • the cosmetic and dermatological preparations according to the invention can comprise 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 constituents of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • 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 constituents of a
  • the lipid phase can advantageously be selected from the following substance group: mineral oils, mineral waxes oils, such as triglycerides of capric acid or of caprylic acid, also natural oils such as e.g. castor oil; fats, waxes and other natural and synthetic fatty bodies, preferably esters of fatty acids with alcohols of low carbon number, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low carbon number or with fatty acids; alkyl benzoates; silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixtures thereof.
  • mineral oils mineral waxes oils, such as triglycerides of capric acid or of caprylic acid, also natural oils such as e.g. castor oil
  • fats, waxes and other natural and synthetic fatty bodies preferably esters of fatty acids with alcohol
  • the oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions within the context of the present invention is advantageously selected from the group of esters of saturated and/or unsaturated, branched and/or unbranched alkanecarboxylic acids of chain length from 3 to 30 C atoms and saturated and/or unsaturated, branched and/or unbranched alcohols of chain length from 3 to 30 C atoms, from the group of esters of aromatic carboxylic acids and saturated and/or unsaturated, branched and/or unbranched alcohols of chain length from 3 to 30 C atoms.
  • 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, oleyl erucate, erucyl oleate, erucyl erucate, and synthetic, semisynthetic and natural mixtures of such esters, e.g. jojoba oil.
  • the aqueous phase of the preparations according to the invention optionally advantageously comprises humectants such as e.g. propylene glycol, panthenol or hyaluronic acid, and in particular one or more thickeners which can advantageously be selected from the group silicon dioxide, aluminum silicates, hydroxypropylmethylcellulose, particularly advantageously a polyacrylate such as, for example, carbopol grade 980, in each case individually or in combination.
  • humectants such as e.g. propylene glycol, panthenol or hyaluronic acid
  • thickeners which can advantageously be selected from the group silicon dioxide, aluminum silicates, hydroxypropylmethylcellulose, particularly advantageously a polyacrylate such as, for example, carbopol grade 980, in each case individually or in combination.
  • mixtures of the aforementioned solvents are used.
  • water can be a further constituent.
  • Emulsions according to the invention are advantageous and comprise e.g. the specified fats, oils, waxes and other fatty bodies, as well as water and an emulsifier, as is customarily used for such a type of formulation.
  • Gels according to the invention usually comprise alcohols of low carbon number, e.g. ethanol, propylene glycol, and water or an aforementioned oil in the presence of a thickener which, in the case of oily-alcoholic gels, is preferably silicon dioxide or an aluminum silicate, and in the case of aqueous-alcoholic or alcoholic gels is preferably a polyacrylate.
  • a thickener which, in the case of oily-alcoholic gels, is preferably silicon dioxide or an aluminum silicate, and in the case of aqueous-alcoholic or alcoholic gels is preferably a polyacrylate.
  • Suitable propellants for preparations according to the invention that can be sprayed from aerosol containers are the customary known readily volatile, liquefied propellants, for example hydrocarbons (propane, butane, isobutane) , which can be used on their own or in a mixture with one another. Compressed air is also to be used advantageously.
  • preparations according to the invention can furthermore advantageously comprise substances which absorb UV radiation in the UVB region, the total amount of the filter substances being e.g. 0.1%by weight to 30%by weight, preferably 0.5 to 10%by weight, in particular 1.0 to 6.0%by weight, based on the total weight of the preparations, in order to provide cosmetic preparations which protect the hair and/or the skin from the entire range of ultraviolet radiation. They can also serve as sunscreens for the hair or the skin.
  • preparations according to the invention can advantageously additionally comprise substances which conceal the troublesome intrinsic odor of the remaining raw materials used, the total amount of the perfume ingredients being e.g. 0.001%by weight to 30%by weight, preferably 0.05 to 10%by weight, in particular 0.1 to 5.0%by weight, based on the total weight of the preparations, in order to provide cosmetic preparations.
  • compositions according to the present invention contain:

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Abstract

Combinaisons d'ingrédients actifs a) d'un ou plusieurs alkylamidothiazoles et b) de diméthylméthoxy chromanol c) dans un excipient cosmétique.
PCT/CN2023/140489 2023-12-21 2023-12-21 Combinaisons d'un ou plusieurs alkylamidothiazoles et de diméthylméthoxy chromanol, et préparations cosmétiques contenant de telles combinaisons Pending WO2025129541A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/CN2023/140489 WO2025129541A1 (fr) 2023-12-21 2023-12-21 Combinaisons d'un ou plusieurs alkylamidothiazoles et de diméthylméthoxy chromanol, et préparations cosmétiques contenant de telles combinaisons
PCT/EP2024/085442 WO2025131863A1 (fr) 2023-12-21 2024-12-10 Combinaisons d'un ou plusieurs alkylamidothiazoles et diméthyl méthoxy chromanol et préparations cosmétiques contenant de telles combinaisons

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2023/140489 WO2025129541A1 (fr) 2023-12-21 2023-12-21 Combinaisons d'un ou plusieurs alkylamidothiazoles et de diméthylméthoxy chromanol, et préparations cosmétiques contenant de telles combinaisons

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WO2025129541A1 true WO2025129541A1 (fr) 2025-06-26

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PCT/EP2024/085442 Pending WO2025131863A1 (fr) 2023-12-21 2024-12-10 Combinaisons d'un ou plusieurs alkylamidothiazoles et diméthyl méthoxy chromanol et préparations cosmétiques contenant de telles combinaisons

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WO2015090850A1 (fr) * 2013-12-19 2015-06-25 Beiersdorf Ag Utilisation d'alkylamidothiazoles en tant qu'antioxydants ou capteurs de radicaux libres dans des préparations cosmétiques ou dermatologigues
WO2018137854A1 (fr) * 2017-01-24 2018-08-02 Beiersdorf Ag Associations de principes actifs constituées de trans-4-t-butylcyclohexanol et d'un ou de plusieurs akylamidothiazols et préparations cosmétiques ou dermatologiques contenant ces associations de principes actifs
WO2021104782A1 (fr) * 2019-11-27 2021-06-03 Beiersdorf Ag Utilisation d'alkylamidothiazoles dans des préparations cosmétiques ou dermatologiques pour le soin d'une peau humaine tatouée et en particulier pour augmenter la brillance de tatouages sur une peau humaine foncée
CN112618457A (zh) * 2020-12-31 2021-04-09 泉后(广州)生物科技研究院有限公司 一种淡化黄褐斑组合物及其制备方法与应用
CN116637053A (zh) * 2023-06-29 2023-08-25 广州市百好博有限公司 一种敏感肌适用的美白组合物及其应用

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