WO2025093184A1 - Combinaisons de principes actifs constituées d'alkylamidothiazoles et de gamma undécalactone - Google Patents
Combinaisons de principes actifs constituées d'alkylamidothiazoles et de gamma undécalactone Download PDFInfo
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- WO2025093184A1 WO2025093184A1 PCT/EP2024/075750 EP2024075750W WO2025093184A1 WO 2025093184 A1 WO2025093184 A1 WO 2025093184A1 EP 2024075750 W EP2024075750 W EP 2024075750W WO 2025093184 A1 WO2025093184 A1 WO 2025093184A1
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- Prior art keywords
- branched
- linear
- alkyl
- weight
- cycloalkyl
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Classifications
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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
- 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
-
- 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 comprising one or more alkylamidothiazoles and gamma-undecalactone. Furthermore, the present invention relates to cosmetic or dermatological preparations containing such active ingredient combinations 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 - depending on the skin type, they occur either individually or in greater or lesser numbers.
- Melanocytes contain melanosomes, characteristic cell organelles in which melanin is produced. Melanin production is increased when stimulated by UV radiation, among other things. This melanin is transported through the living layers of the epidermis (keratinocytes) into the horny layer (corneocytes), producing a more or less pronounced brownish to brown-black skin color.
- DHICA and DHI melanin are formed via the common intermediates dopaquinone and dopachrome. The latter, sometimes with the involvement of other enzymes, is converted into either indole-5,6-quinone carboxylic acid or indole-5,6-quinone, from which the two aforementioned eumelanins are formed.
- pheomelanin occurs, among other things, via the intermediates 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
- p-protein appears to play an important role, although its exact function is still unclear.
- melanosomes influence their light-scattering properties and thus the color appearance of the skin.
- large, spheroidal melanosomes are more commonly found in black Africans, 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. senile lentigines).
- 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 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.
- Gamma-undecalactone (undecano-1,4)-lactone) is characterized by the following structural formula:
- 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 -
- the thiazoles mentioned can exist both as a free base and as a salt: e.g. as fluoride, chloride, bromide, iodide, sulfate, carbonate, ascorbate, acetate or phosphate. In particular as halogen salts, such as chloride and bromide.
- 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 further provides for the use of the aforementioned alkylamidothiazoles for the treatment and/or prophylaxis of unwanted skin pigmentation.
- the treatment and/or prophylaxis of unwanted skin pigmentation can be carried out both in a cosmetic and a pharmaceutical context.
- 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
- Z -H, -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN, acetyl.
- 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 present in various forms.
- 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.
- the cosmetic and dermatological preparations according to the invention can 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 ingredients 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 ingredients of a cosmetic or
- 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 of 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
- 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, 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 the 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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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
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- Epidemiology (AREA)
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- Cosmetics (AREA)
Abstract
L'invention concerne des combinaisons d'ingrédients actifs constitués d'un ou plusieurs alkylamidothiazoles et gamma undécalactone.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102023210919.0 | 2023-11-03 | ||
| DE102023210919.0A DE102023210919A1 (de) | 2023-11-03 | 2023-11-03 | Wirkstoffkombinationen aus Alkylamidothiazolen und Gamma-Undecalacton |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2025093184A1 true WO2025093184A1 (fr) | 2025-05-08 |
Family
ID=92801348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2024/075750 Pending WO2025093184A1 (fr) | 2023-11-03 | 2024-09-16 | Combinaisons de principes actifs constituées d'alkylamidothiazoles et de gamma undécalactone |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE102023210919A1 (fr) |
| WO (1) | WO2025093184A1 (fr) |
Citations (4)
| 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 |
| WO2022124027A1 (fr) * | 2020-12-07 | 2022-06-16 | 株式会社 資生堂 | Composition de préparation externe cutanée |
-
2023
- 2023-11-03 DE DE102023210919.0A patent/DE102023210919A1/de active Pending
-
2024
- 2024-09-16 WO PCT/EP2024/075750 patent/WO2025093184A1/fr active Pending
Patent Citations (4)
| 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 |
| WO2022124027A1 (fr) * | 2020-12-07 | 2022-06-16 | 株式会社 資生堂 | Composition de préparation externe cutanée |
Non-Patent Citations (3)
| Title |
|---|
| A. KLIGMAN, ARCH. DERMATOL., vol. 111, 1975, pages 40 - 48 |
| J.M. READY, BIOORGANIC & MEDICINAL CHEMISTRY LETTER, vol. 17, 2007, pages 6871 - 6875 |
| M. SEIBERG ET AL., J. CELL. SCI., vol. 113, 2000, pages 3093 - 101 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE102023210919A1 (de) | 2025-05-08 |
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