WO2015090850A1 - Utilisation d'alkylamidothiazoles en tant qu'antioxydants ou capteurs de radicaux libres dans des préparations cosmétiques ou dermatologigues - Google Patents

Utilisation d'alkylamidothiazoles en tant qu'antioxydants ou capteurs de radicaux libres dans des préparations cosmétiques ou dermatologigues Download PDF

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Publication number
WO2015090850A1
WO2015090850A1 PCT/EP2014/075309 EP2014075309W WO2015090850A1 WO 2015090850 A1 WO2015090850 A1 WO 2015090850A1 EP 2014075309 W EP2014075309 W EP 2014075309W WO 2015090850 A1 WO2015090850 A1 WO 2015090850A1
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WIPO (PCT)
Prior art keywords
branched
linear
alkyl
alky
dihydroxyphenyl
Prior art date
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PCT/EP2014/075309
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German (de)
English (en)
Inventor
Ludger Kolbe
Cathrin Scherner
Ursula Wensorra
Tobias Mann
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Beiersdorf Ag
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Publication of WO2015090850A1 publication Critical patent/WO2015090850A1/fr

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    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • 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

Definitions

  • alkylamidothiazoles as antioxidant or radical scavenger in cosmetic or dermatological preparations
  • the present invention relates to cosmetic and dermatological preparations with an effective content of physiologically acceptable alkylamidothiazoles.
  • the present invention relates to cosmetic preparations with effective protection against harmful oxidation processes in the skin, but also for the protection of cosmetic preparations themselves or for the protection of the components of cosmetic preparations from harmful oxidation processes.
  • the present invention further relates to antioxidants, preferably those which are used in skin-care cosmetic or dermatological preparations.
  • the invention also relates to cosmetic and dermatological preparations containing such antioxidants.
  • the present invention relates to cosmetic and dermatological preparations for the prophylaxis and treatment of cosmetic or dermatological lesions, e.g. Skin aging, especially skin aging caused by oxidative processes.
  • the present invention relates to active substances and preparations containing such active ingredients, for the cosmetic and dermatological treatment or prophylaxis of erythema-tuiter, inflammatory, allergic or autoimmune reactive phenomena, especially dermatoses.
  • the present invention further relates to active compound combinations and preparations which are used for the prophylaxis and treatment of the photosensitive skin, in particular of photodermatoses.
  • the damaging effect of the ultraviolet part of solar radiation on the skin is well known. While rays having a wavelength smaller than 290 nm (the so-called UVC region) are absorbed by the ozone layer in the earth's atmosphere, rays in the range between 290 nm and 320 nm, the so-called UVB region, cause erythema simple sunburn or even more or less severe burns.
  • UVA range it is important to have available filter substances, since its rays can cause reactions in photosensitive skin. It has been proven that UVA radiation leads to damage of the elastic and collagenous fibers of the connective tissue, causing the skin to age prematurely, and that it is to be regarded as the cause of numerous phototoxic and photoallergic reactions. The damaging influence of UVB radiation can be amplified by UVA radiation.
  • UV radiation can also lead to photochemical reactions, in which case the photochemical reaction products intervene in the skin metabolism.
  • such photochemical reaction products are free-radical compounds, for example hydroxy radicals.
  • Undefined radical photoproducts which are formed in the skin itself, can also be used because of their high reactivity uncontrolled follow-up reactions to the day.
  • singlet oxygen a non-traditional excited state of the oxygen molecule, can also occur on UV irradiation, as can short-lived epoxides and many others.
  • Singlet oxygen for example, is distinguished from the normally present triplet oxygen (radical ground state) by increased reactivity. However, there are also excited, reactive (radical) triplet states of the oxygen molecule.
  • UV radiation counts as ionizing radiation.
  • ionic species may also be formed on exposure to UV radiation, which in turn may intervene oxidatively in the biochemical processes.
  • antioxidants and / or radical scavengers can be incorporated in the cosmetic or dermatological formulations. It has already been proposed to use vitamin E, a substance with known antioxidant activity in sunscreen formulations, yet here again, the effect achieved lags far behind the hoped for.
  • the object of the invention was therefore also to provide cosmetic, dermatological and pharmaceutical active ingredients and preparations as well as light protection formulations which serve for the prophylaxis and treatment of photosensitive skin, in particular photodermatoses, preferably PLD.
  • Erythematous skin manifestations also appear as side effects in certain skin diseases or irregularities. For example, the typical rash in the appearance of acne is regularly more or less reddened.
  • Mainly antioxidants are used as protective substances against spoilage of preparations containing them. Nevertheless, it is known that also in the human and animal skin unwanted oxidation processes can occur. Such processes play an essential role in skin aging.
  • oxidizing hair dyeing the formation of the dye chromophore takes place by reaction of precursors (phenols, aminophenols, more rarely diamines) and bases (usually p-phenylenediamine) with the oxidizing agent, usually hydrogen peroxide. Hydrogen peroxide concentrations around 6% are usually used.
  • Antioxidants are substances which prevent oxidation processes and / or which prevent the oxidation of unsaturated compounds containing auto-oxidation.
  • Antioxidants which are also used in the field of cosmetics and pharmacy are, for example, ⁇ -tocopherol, in particular in the form of ⁇ -tocopheryl acetate, sesamol, gallic acid derivatives, butylhydroxyanisole and butylhydroxytoluene.
  • antioxidants and / or radical scavengers may additionally be incorporated into cosmetic formulations.
  • antioxidants and radical scavengers are known.
  • vitamin E a substance with known antioxidant activity in sunscreen formulations, but the effect achieved remains far below the hoped-for effect.
  • An object of the present invention was to eliminate the disadvantages of the prior art.
  • active ingredients or preparations containing such active ingredients should be made available, in the use of which damage to the skin and / or the hair is at least reduced by oxidative influence, if not completely prevented.
  • a further object of the present invention was to provide cosmetic preparations which, before or after treatment of the hair with hair-dyeing preparations, even those containing a strong oxidizing agent, such as e.g. Hydrogen peroxide, whose damaging oxidation effect counteract.
  • a strong oxidizing agent such as e.g. Hydrogen peroxide
  • active substances and preparations containing such active ingredients should be made available for the cosmetic and dermatological treatment and / or prophylaxis of erythematous, inflammatory, allergic or autoimmune-reactive phenomena, in particular dermatoses, but also the appearance of "stinging".
  • compositions containing physiologically tolerated alkylamide dothiazoles or the use of physiologically tolerated alkylamidothiazoles as antioxidant and / or radical scavenger in cosmetic or dermatological preparations represents the solution to these problems, and to remedy the disadvantages of the prior art.
  • Advantageous alkylamidothiazoles in the context of the present invention are substances of the general formula in which R 1 , R 2 , X and Y can be different, partly identical or completely identical and can mean independently of one another:
  • Ri -Ci-C24-alkyl (linear and branched), -Ci-C24-alkenyl (linear and branched), -d-Cs-cycloalkyl, -Ci-Ce-cycloalkyl-alkylhydroxy, -C1-C24 alkylhydroxy (linear and .alpha Branched), -C1-C24 alkylamine (linear and branched), -Ci-C24-alkylaryl (linear and branched), -Ci-C24-alkyl-aryl-alkyl-hydroxy (linear and branched), -Ci-C24-alkylheteroaryl (linear and branched), -d-C24-alkyl-0-Ci-C24-Alkyl (linear and branched), -C1-C24 Alky-Morpholino, -C1-C24 Alky-Piperidino, -C1-
  • X -H, -Ci-C24-alkyl (linear and branched), -Ci-C24-alkenyl (linear and branched), -Ci-Ce- cycloalkyl, -Ci-C24-aryl (optionally mono- or polysubstituted with -OH, -F, -Cl, -Br, -I, - OMe, -NH 2 , -CN), -Ci-C24 heteroaryl (optionally mono- or polysubstituted by -OH, -F, - Cl, - Br, -I, -OMe, -NH 2 , -CN), -Ci-C 2 4-alkylaryl (linear and branched), -Ci-C 2 4-alkyl heteroaryl (linear and branched), -aryl (if necessary monosubstituted or polysubstituted by -OH, -F, -Cl
  • the stated thiazoles can be present both as free base and as salt: for example as fluoride, chloride, bromide, iodide, sulfate, carbonate, ascorbate, acetate or phosphate.
  • halogen salts such as chloride and bromide.
  • X is selected from the group of substituted phenyls, where the substituents (Z) can be selected from the group -H, -OH, -F, -Cl, -Br, -I, -OMe, -NH2, - CN, acetyl and the same or different.
  • X is particularly preferably selected from the group of phenyl groups substituted by one or more hydroxyl groups, where the substituent (Z) can be selected from the group -H, -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN, acetyl and the following generic Structure is preferred in which Y, R 1 and R 2 may have the properties defined above.
  • Ri -Ci-C24-alkyl (linear and branched), -Ci-C24-alkenyl (linear and branched), -d-Cs-cycloalkyl, -Ci-Ce-cycloalkyl-alkylhydroxy, -C1-C24 alkylhydroxy (linear and .alpha Branched), -C1-C24 alkylamine (linear and branched), -Ci-C24-alkylaryl (linear and branched), -Ci-C24-alkyl-aryl-alkyl-hydroxy (linear and branched), -Ci-C24-alkylheteroaryl (linear and branched), -d-C24-alkyl-0-Ci-C24-Alkyl (linear and branched), -C1-C24 Alky-Morpholino, -C1-C24 Alky-Piperidino, -C1-
  • R2 H, -Ci-C24-alkyl (linear and branched).
  • Z -H, -OH, -F, -Cl, -Br, -I, -OMe, -NH 2 , -CN, acetyl.
  • Ri -Ci-C24-alkyl (linear and branched), -Ci-C24-alkenyl (linear and branched), -Ci-Ce- cycloalkyl, -d-Ce-cycloalkyl-alkylhydroxy, -C1-C24 alkylhydroxy (linear and Branched), -C1-C24 alkylamine (linear and branched), -Ci-C24-alkylaryl (linear and branched), -Ci-C24-alkyl-aryl-alkyl-hydroxy (linear and branched), -Ci-C24-alkylheteroaryl (linear and branched), C1-C24-alkyl-0-Ci-C24-Alkyl (linear and branched), -C1-C24 Alky-Morpholino, -C1-C24 Alky-Piperidino, -C1-C24 Alky
  • a '- (4- (2,4-dihydroxyphenyl) thiazo1-2-yl) -2- (4- (hydroxymethyl) phenyl) acetamides are the preferred according to the invention.
  • the alkylamidothiazoles in cosmetic or Dermatological preparations have higher stability than comparable active ingredients, for example as vitamin C.
  • the cosmetic or dermatological formulations according to the invention may be composed as usual and used for the treatment, care and cleansing of the skin and / or the hair and as a make-up product in decorative cosmetics. They preferably contain 0.000001 wt .-% to 10 wt .-%, preferably 0.0001 wt .-% to 3 wt .-%, in particular 0.001 - 1, 0 wt .-%, based on the total weight of the composition , on one or more physiologically acceptable alkylamidothiazoles.
  • the cosmetic and dermatological preparations according to the invention are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics.
  • the active ingredient used according to the invention can be incorporated into customary cosmetic and dermatological preparations which may be in various forms. So they can z.
  • a solution a water-in-oil (W / O) or oil-in-water (O / W) type emulsion, or a multiple emulsions, such as water-in-oil-in-water type (W / O / W) or oil-in-water-in-oil (O / W / O), a hydrodispersion or lipodispersion, a Pickering emulsion, a gel, a solid stick or even an aerosol.
  • emulsions, z. B. in the form of a cream, a lotion, a cosmetic milk are advantageous and contain z.
  • emulsifiers such as are commonly used for such a type of formulation.
  • Medicinal topical compositions according to the present invention usually contain one or more drugs in effective concentration.
  • a clear distinction between cosmetic and medical use and corresponding products is made to the statutory provisions of the Federal Republic of Germany (eg Cosmetics Ordinance, Food and Medicinal Products Act). It is also advantageous to add the active ingredient used according to the invention as an additive to preparations which already contain other active ingredients for other purposes.
  • cosmetic or topical dermatological compositions according to the present invention depending on their structure, for example, be used as skin protection cream, cleansing milk, sunscreen lotion, nutrient cream, day or night cream, etc. It is possible and advantageous, the compositions of the invention as a basis for pharmaceutical To use formulations.
  • the cosmetic and dermatological preparations are applied according to the invention in the usual manner for cosmetics on the skin and / or hair in sufficient quantity.
  • Particularly preferred are those cosmetic and dermatological preparations which are in the form of a sunscreen.
  • these may additionally contain at least one further UVA filter and / or at least one further UVB filter and / or at least one inorganic pigment, preferably an inorganic micropigment.
  • the cosmetic and dermatological preparations according to the invention may contain cosmetic adjuvants such as are commonly used in such preparations, e.g. Preservatives, bactericides, perfumes, foaming inhibitors, dyes, pigments having a coloring effect, thickeners, moisturizing and / or moisturizing substances, fats, oils, waxes or other common ingredients of a cosmetic or dermatological formulation such as alcohols, polyols, Polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • An additional level of conventional antioxidants is generally preferred. According to the invention, all antioxidants which are suitable or customary for cosmetic and / or dermatological applications can be used as favorable antioxidants.
  • the amount of the aforementioned antioxidants (one or more compounds) in the preparations is preferably from 0.001 to 30% by weight, particularly preferably from 0.05 to 20% by weight, in particular from 1 to 10% by weight, based on the Total weight of the preparation.
  • the cosmetic or dermatological preparation in the sense of the present invention is a solution or emulsion or dispersion, the following can be used as solvent:
  • Oils such as triglycerides of capric or caprylic acid, but preferably castor oil; Fats, waxes and other natural and synthetic fats, preferably esters of fatty acids with lower C-number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids low C number or with
  • Alcohols, diols or polyols of low C number, and their ethers preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products.
  • mixtures of the abovementioned solvents are used.
  • alcoholic solvents water can be another ingredient.
  • the cosmetic or dermatological preparation in the sense of the present invention is a solution or emulsion or dispersion, it is possible to use as solvent:
  • Oils such as triglycerides of capric or caprylic acid, but preferably castor oil; Fats, waxes and other natural and synthetic fats, preferably esters of fatty acids with lower C-number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids;
  • Alcohols, diols or polyols of low C number, and their ethers preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products ,
  • mixtures of the abovementioned solvents are used.
  • alcoholic solvents water can be another ingredient.
  • Suitable propellants for cosmetic and / or dermatological preparations which can be sprayed from aerosol containers in the context of the present invention are the customary known highly volatile, liquefied propellants, for example hydrocarbons (propane, butane, isobutane), which can be used alone or mixed with one another. Also, compressed air is advantageous to use.
  • hydrocarbons propane, butane, isobutane
  • compressed air is advantageous to use.
  • Cosmetic preparations in the context of the present invention may also be present as gels which, in addition to an effective content of the active ingredient according to the invention and solvents used for this purpose, preferably water, also organic thickening agents, e.g. Gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose or inorganic thickening agents, e.g. For example, aluminum silicates such as bentonites, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate.
  • the thickener is present in the gel e.g.
  • the sunscreen formulations can advantageously comprise further substances which absorb UV radiation in the UVB range, the total amount of the filter substances being e.g. 0, 1 wt .-% to 30 wt .-%, preferably 0.5 to 10 wt .-%, in particular 1 to 6 wt .-%, based on the total weight of the preparations in order to provide cosmetic preparations, which protect the skin from the entire range of ultraviolet radiation. They can also serve as sunscreen.
  • Neutrophil granulocytes are capable of releasing large amounts of reactive oxygen species (ROS) in response to a stimulus in an "oxidative burst.”
  • ROS reactive oxygen species
  • These oxygen radicals are designed to kill bacteria or (yeast) fungi that have invaded wounds, for example Experimentally, the oxidative burst can be triggered by bacterial components such as formylated peptides, which in principle means that the production of ROS by granulocytes is a protective reaction of the body against microbial infections It is also important to avoid tissue damage (oxidative stress) and an excess granulocyte reaction.
  • a reduction in the release of reactive oxygen radicals by antioxidants can therefore also be interpreted as a reduction of the oxidative stress and thus demonstrate their general anti-oxidative activity.
  • neutrophil granulocytes were isolated by gradient centrifugation from human blood and incubated with different concentrations of the drug. Subsequently, the burst with the bacterial peptide formyl-methionyl-leucyl-phenylalanine (fMLP) was triggered and the release of the radicals detected by a luminol chemiluminescence.
  • fMLP formyl-methionyl-leucyl-phenylalanine
  • N- (4- (2,4-dihydroxyphenyl) thiazol-2-yl) -isobutyramide was investigated in the test described above and shows in this experiment a dose-dependent activity in the concentration range> 5.56 ⁇ (see FIG ).
  • Paraffin Liquidum (mineral oil) 0.5

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
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  • Epidemiology (AREA)
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Abstract

L'invention concerne l'utilisation d'alkylamidothiazoles physiologiquement tolérables en tant qu'antioxydants et/ou capteurs de radicaux libres dans des préparations cosmétiques ou dermatologiques.
PCT/EP2014/075309 2013-12-19 2014-11-21 Utilisation d'alkylamidothiazoles en tant qu'antioxydants ou capteurs de radicaux libres dans des préparations cosmétiques ou dermatologigues WO2015090850A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102013226746.0A DE102013226746A1 (de) 2013-12-19 2013-12-19 Verwendung von Alkylamidothiazolen als Antioxidans oder Radikalfänger in kosmetischen oder dermatologischen Zubereitungen
DE102013226746.0 2013-12-19

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
WO2021255011A1 (fr) * 2020-06-15 2021-12-23 Dsm Ip Assets B.V. Procédé de fabrication d'alkylamidothiazoles

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DE102017202557A1 (de) 2017-02-17 2018-08-23 Beiersdorf Ag Stabile Reinigungszubereitung
DE102018211412A1 (de) * 2018-07-10 2020-01-16 Beiersdorf Ag Selbstklebende flächige Produkte enthaltend ein oder mehrere Alkylamidothiazole

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US4248861A (en) 1979-02-21 1981-02-03 Schutt Steven R Skin treatment methods
EP2072519A1 (fr) 2006-09-28 2009-06-24 Banyu Pharmaceutical Co., Ltd. Dérivé de diarylcétimine
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WO2014139758A1 (fr) * 2013-03-11 2014-09-18 Beiersdorf Ag Compositions composées d'alkylamidothiazoles et de parfums
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US4248861A (en) 1979-02-21 1981-02-03 Schutt Steven R Skin treatment methods
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Cited By (2)

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Publication number Priority date Publication date Assignee Title
WO2021255011A1 (fr) * 2020-06-15 2021-12-23 Dsm Ip Assets B.V. Procédé de fabrication d'alkylamidothiazoles
CN115702148A (zh) * 2020-06-15 2023-02-14 帝斯曼知识产权资产管理有限公司 用于制造烷基酰胺噻唑的方法

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