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WO2025093177A1 - Combinaisons de principes actifs constituées d'alkylamidothiazoles et de delta-décalactone - Google Patents

Combinaisons de principes actifs constituées d'alkylamidothiazoles et de delta-décalactone Download PDF

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Publication number
WO2025093177A1
WO2025093177A1 PCT/EP2024/075473 EP2024075473W WO2025093177A1 WO 2025093177 A1 WO2025093177 A1 WO 2025093177A1 EP 2024075473 W EP2024075473 W EP 2024075473W WO 2025093177 A1 WO2025093177 A1 WO 2025093177A1
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WIPO (PCT)
Prior art keywords
branched
linear
alkyl
dihydroxyphenyl
weight
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/EP2024/075473
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German (de)
English (en)
Inventor
Anette Buerger
Sabrina Dorsch
Sylke Hansson
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Beiersdorf AG
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Beiersdorf AG
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Filing date
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Publication of WO2025093177A1 publication Critical patent/WO2025093177A1/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

Definitions

  • the present invention relates to active ingredient combinations of one or more alkylamidothiazoles and ⁇ -decalactone.
  • the present invention further relates to cosmetic or dermatological preparations containing such an active ingredient combination and their use for lightening human skin.
  • Melanocytes are responsible for the pigmentation of the skin. These pigment-forming cells are found in the lowest layer of the epidermis, the stratum basale, alongside the basal cells as pigment-forming cells - occurring either individually or in greater or lesser numbers depending on the skin type. Melanocytes contain melanosomes as characteristic cell organelles in which melanin is formed.
  • Melanin formation is increased when stimulated by UV radiation, among other things. This is transported via the living layers of the epidermis (keratinocytes) ultimately into the horny layer (corneocytes), resulting in a more or less pronounced brownish to brown-black skin color.
  • Melanin is formed as the final stage of an oxidative process in which tyrosine, with the assistance of the enzyme tyrosinase, is converted via several intermediate stages into the brown to brown -black eumelanins (DHICA and DHI melanin) or, with the involvement of sulfur-containing compounds, into the reddish pheomelanin.
  • DHICA and DHI melanin are formed via the common intermediates dopaquinone and dopachrome.
  • the latter is converted, sometimes with the involvement of other enzymes, either into indole-5,6-quinone carboxylic acid or into indole-5,6-quinone, from which the two aforementioned eumelanins are formed.
  • the formation of pheomelanin occurs, among other things, via the intermediate products dopaquinone and cysteinyldopa.
  • the expression of the melanin-synthesizing enzymes is controlled by a specific transcription factor (microphthalmia-associated transcription factor, MITF).
  • MITF microphthalmia-associated transcription factor
  • Other proteins in the melanosomes are also important for melanogenesis.
  • the so-called p-protein appears to play an important role here, although its exact function is still unclear.
  • melanosomes influence their light-scattering properties and thus the color appearance of the skin. For example, black Africans tend to have larger, solitary spheroidal melanosomes, while Caucasians tend to have smaller, clustered melanosomes.
  • UV radiation e.g. freckles, ephelides
  • genetic predisposition e.g., incorrect pigmentation of the skin during wound healing or scarring (post-inflammatory hyperpigmentation) or skin aging (e.g. lentigines seniles).
  • Skin peeling methods (chemical and mechanical peels) are also used, but these often result in inflammatory reactions and, due to subsequent post-inflammatory hyperpigmentation, can even lead to increased rather than reduced pigmentation. All of these common procedures, which are also used to treat post-inflammatory hyperpigmentation, are characterized by significant side effects.
  • various other substances are known for which a skin-lightening effect has been described. These include, among others, hexadecene-1,16-dicarboxylic acid, kojic acid and derivatives, arbutin, ascorbic acid and derivatives, flavonoids, ellagic acid and derivatives, tranexamic acid, and various resorcinol derivatives, such as 4-n-butylresorcinol, 4-n-hexylresorcinol, and 4-(1-phenylethyl)benzene-1,3-diol.
  • Smell is one of the five human senses. Odors, highly volatile substances, are bound by olfactory receptors in the nasal mucosa. The stimulus is transmitted via a signaling cascade to the nerve cells and forwarded to the brain. There, the actual sense of smell arises. Pleasant smells are differentiated from unpleasant smells.
  • This task is solved by combinations of active ingredients consisting of one or more alkylamidothiazoles and A-decalactone.
  • ⁇ -Decalactone occurs as a flavoring agent in various foods. It is one of the most important components of butter flavor and also contributes to the flavor of other dairy products such as UHT milk and various cheeses. It is also found in various fruits such as peaches, apricots, coconuts, and raspberries.
  • ⁇ -Decalactone can exist in two different enantiomers, the R and S forms. Both enantiomers as well as racemic mixtures with identical or different contents of both enantiomers are equally advantageous according to the invention.
  • the preparations according to the invention preferably contain 0.00001 - 1% by weight of ⁇ - decalactone, preferably 0.0001 - 0.5% by weight of ⁇ -decalactone, particularly preferably 0.0005 - 0.3% by weight of ⁇ -decalactone.
  • Preparations or uses according to the invention are particularly advantageous, characterized in that the preparations contain 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 alkylamidothiazoles , based on the total weight of the preparation.
  • R1 -C1–C24–alkyl (linear and branched), -C1–C24-alkenyl (linear and branched), -C1-C8-cycloalkyl , -C 1 -C 8 -cycloalkyl-alkylhydroxy, -C 1 -C 24 alkylhydroxy (linear and branched), -C 1 -C 24 alkylamine (linear and branched), -C 1 –C 24 –alkylaryl (linear and branched), -C 1 –C 24 –alkylaryl-alkyl-hydroxy (linear and branched), -C 1 –C 24 –alkylheteroaryl (linear and branched), -C 1 -C 1 -C
  • an advantageous implementation of the present invention consists in cosmetic or dermatological preparations with an effective content of one or more of the aforementioned alkylamidothiazoles.
  • the invention also relates to the use of the aforementioned alkylamidothiazoles for the treatment and/or prophylaxis of undesired skin pigmentation. Treatment and/or prophylaxis of unwanted skin pigmentation can be carried out both cosmetically and pharmaceutically.
  • X is advantageously selected from the group of substituted phenyls, where the substituents (Z) can be selected from the group consisting of -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 by one or more hydroxy 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 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 alkyl-morpholino, -C1-C24 alkyl
  • Z -H, -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN, acetyl.
  • N are the preferred ones according to the invention.
  • Cosmetic or dermatological preparations containing alkylamidothiazoles and biopolymers according to the invention or their use for the treatment and/or prophylaxis of undesired skin pigmentation are also advantageous embodiments of the present invention.
  • such preparations contain 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.
  • the preparations have slightly basic pH values, i.e. values between 7 and 9, preferably between 7 and 8, in particular between 7.4 and 7.6.
  • Cosmetic and dermatological preparations according to the invention can be in various forms. They can be, for example, 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.
  • the cosmetic and dermatological preparations according to the invention may contain cosmetic auxiliaries as are usually 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 humectants, fats, oils, waxes or other common components of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic auxiliaries 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 humectants, fats, oils, waxes or other common components of a cosmetic or dermatological formulation such as alcohols, polyols, polymers
  • the lipid phase can advantageously be selected from the following substance group: mineral oils, mineral waxes
  • Oils such as triglycerides of capric or caprylic acid, as well as natural oils such as castor oil;
  • 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;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixtures thereof.
  • 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.
  • 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-hexyl decyl stearate, 2-octyldodecyl palmitate, oleyl oleate, dibutyl adipate, propylheptyl caprylate, diisopropyl adipate, cetearyl isononanoate, oleyl erucate, erucyl oleate, erucyl erucate as well as
  • 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.
  • humectants such as propylene glycol, panthenol or hyaluronic acid, individually or in combination.
  • 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.
  • Gels according to the invention usually contain alcohols with a low carbon number, e.g. ethanol, propylene glycol, and water or an oil mentioned above in the presence of a thickener.
  • alcohols with a low carbon number e.g. ethanol, propylene glycol, and water or an oil mentioned above in the presence of a thickener.
  • 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.
  • 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.
  • Preparations according to the invention can advantageously also contain substances that absorb UV radiation in the UVB range, with the total amount of filter substances being, for example, 0.1% 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 that protect the hair or skin from the entire range of ultraviolet radiation. They can also serve as sunscreens for the hair or skin.
  • preparations according to the invention can advantageously additionally contain substances which mask the unpleasant inherent odor of the remaining raw materials used, the total amount of perfume ingredients being, for example, 0.001% by weight to 5% by weight, preferably 0.05 to 3% by weight, in particular 0.1 to 1% by weight, based on the total weight of the preparations, in order to provide cosmetic preparations.

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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)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des combinaisons de principes actifs constituées d'un ou plusieurs alkylamidothiazoles et de Δ-décalactone.
PCT/EP2024/075473 2023-11-03 2024-09-12 Combinaisons de principes actifs constituées d'alkylamidothiazoles et de delta-décalactone Pending WO2025093177A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102023210907.7 2023-11-03
DE102023210907.7A DE102023210907A1 (de) 2023-11-03 2023-11-03 Wirkstoffkombinationen aus Alkylamidothiazolen und delta-Decalacton

Publications (1)

Publication Number Publication Date
WO2025093177A1 true WO2025093177A1 (fr) 2025-05-08

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PCT/EP2024/075473 Pending WO2025093177A1 (fr) 2023-11-03 2024-09-12 Combinaisons de principes actifs constituées d'alkylamidothiazoles et de delta-décalactone

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DE (1) DE102023210907A1 (fr)
WO (1) WO2025093177A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009099195A1 (fr) 2008-02-08 2009-08-13 Shiseido Company Ltd. Agent blanchissant pour la peau et préparation externe pour la peau
EP2758381A1 (fr) 2011-09-23 2014-07-30 Beiersdorf AG Alkyle-amido-thiazoles, préparations cosmétiques ou dermatologiques qui en contiennent et utilisation desdites préparations pour traiter et prévenir une pigmentation cutanée indésirable
WO2014139758A1 (fr) * 2013-03-11 2014-09-18 Beiersdorf Ag Compositions composées d'alkylamidothiazoles et de parfums

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009099195A1 (fr) 2008-02-08 2009-08-13 Shiseido Company Ltd. Agent blanchissant pour la peau et préparation externe pour la peau
EP2758381A1 (fr) 2011-09-23 2014-07-30 Beiersdorf AG Alkyle-amido-thiazoles, préparations cosmétiques ou dermatologiques qui en contiennent et utilisation desdites préparations pour traiter et prévenir une pigmentation cutanée indésirable
WO2014139758A1 (fr) * 2013-03-11 2014-09-18 Beiersdorf Ag Compositions composées d'alkylamidothiazoles et de parfums

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
A. KLIGMAN, ARCH. DERMATOL., vol. 111, 1975, pages 40 - 48
BIOORGANIC & MEDICINAL CHEMISTRY LETTER, vol. 17, 2007, pages 6871 - 6875
DATABASE GNPD [online] MINTEL; 23 September 2016 (2016-09-23), ANONYMOUS: "Moisture Lotion", XP093229631, retrieved from https://www.gnpd.com/sinatra/recordpage/4289537/ Database accession no. 4289537 *
M. SEIBERG ET AL., J. CELL. SCI., vol. 113, 2000, pages 3093 - 101
VON ALBERT KLIGMAN ET AL., TRIFORMULA

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Publication number Publication date
DE102023210907A1 (de) 2025-05-08

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