7-Oxo-DHEA compounds for treating keratinous conditions/afflictions

a technology of keratinous conditions and compounds, applied in the field of 7oxodhea derivatives, can solve the problems of difficult hormonal effects of dhea, and achieve the effect of improving the appearance of keratinous substrates/materials

Inactive Publication Date: 2005-07-28
LOREAL SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, DHEA has hormonal effects that may prove difficult as regards the administration of same.

Method used

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  • 7-Oxo-DHEA compounds for treating keratinous conditions/afflictions
  • 7-Oxo-DHEA compounds for treating keratinous conditions/afflictions
  • 7-Oxo-DHEA compounds for treating keratinous conditions/afflictions

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0284] This example describes a variety of specific compositions according to the invention.

[0285] Composition 1; Moisturizing Cream:

Phase A:Acrylate / C10-30 acrylate copolymer0.5%Water12.0% Phase B:Hydrogenated polyisobutene5.0%3β-O-7-oxo-DHEA α-glutamate0.5%Cyclohexasiloxane6.0%Phase C:Triethanolamine1.0%Glycerol6.0%EDTA0.2%Preservatives0.5%Glycine2.0%Polyacrylamide and C13-14 isoparaffin and laureth-71.0%Waterqs 100% 

[0286] This composition was prepared in the following manner. The polymer of phase A was dispersed in water at 40° C. The constituents of phase B were heated to 70° C. until completely dissolved, and the temperature was then reduced to 40° C. The constituents of phase C were mixed together at 50° C. Phase B was then introduced into phase A at 40° C. with stirring, and phase C was then added thereto.

[0287] The above composition rehydrates dry skin and renders it smooth.

Composition 2; Moisturizing Cream:

[0288] The composition below was formulated in conventional ...

example 2

Synthesis of 3β-O-acetyl-7-oxo-DHEA

[0299]

[0300] A solution of 10 g of 3β-O-acetyl-DHEA in 200 ml of acetonitrile was prepared. 60 mg of copper iodide (CuI) were added thereto under an inert atmosphere. The solution was cooled to between 5° and 10° C. and 19.6 ml of 80% t-BuOOH were added dropwise. At the end of the addition, the reaction medium was allowed to return to room temperature and was stirred for 2 hours, followed by heating at 50° C. for 20 hours. The reaction medium was then cooled and poured into 300 g of 10% sodium bicarbonate (NaHCO3) solution. This mixture was extracted three times with diethyl ether and the organic solution was then washed with saturated NaHCO3 solution, and then with saturated sodium chloride (NaCl) solution. After drying and evaporating to dryness, the crude product was obtained in the form of a solid. The residue was recrystallized from an acetone / hexane mixture. [0301] (a) Melting point: 190-192° C.; [0302] (b) Yield: 91%; [0303] (c) [α]d=−76° (...

example 3

Synthesis of 7-oxo-DHEA

[0305]

[0306] A solution of 3β-O-acetyl-7-oxo-DHEA obtained in Example 2 in methanol was prepared. 1 molar equivalent of sodium methoxide (NaOMe) was added and the mixture was stirred for a period of between 3 and 12 hours. The methanol was evaporated off and the residue was diluted with water and extracted with dichloromethane. The organic solution was dried and then evaporated to dryness. The residue was purified by chromatography to give the 7-oxo-DHEA.

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Abstract

7-Oxo-DHEA derivatives, various of which are themselves novel compounds, are well suited for cosmetically / therapeutically treating adverse conditions / afflictions of a keratinous substrate / material, notably of human skin, hair, eyelashes and nails, to improve the appearance thereof, in particular to prevent or treat signs of aging of the skin and / or a dull complexion and / or skin or hair pigmentation disorders and / or dryness of the skin and / or hyperseborrhoea and / or hyperseborrhoea-related imperfections and / or sensitive skin and / or dandruff and / or natural hair loss and / or baldness.

Description

CROSS-REFERENCE TO PRIORITY APPLICATION [0001] This application claims priority under 35 U.S.C. § 119 of FR-01 / 07804, filed Jun. 14, 2001, hereby expressly incorporated by reference. BACKGROUND OF THE INVENTION [0002] 1. Technical Field of the Invention [0003] The present invention relates to novel 7-oxo-DHEA derivatives, to a process for synthesizing such novel compounds and to cosmetic / therapeutic compositions comprising same. [0004] The present invention also relates to cosmetic applications of at least one 7-oxo-DHEA derivative to improve the appearance of keratin materials and substrates, such as the skin, the hair, the eyelashes and the nails, in particular to prevent or treat adverse signs of aging of the skin and / or a dull complexion and / or skin or hair pigmentation disorders and / or dryness of the skin and / or hyperseborrhoea and / or hyperseborrhoea-related imperfections and / or sensitive skin and / or dandruff and / or natural hair loss and / or baldness. [0005] This invention also ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K8/00A61K8/02A61K8/06A61K8/30A61K8/19A61K8/33A61K8/35A61K8/36A61K8/41A61K8/46A61K8/49A61K8/55A61K8/58A61K8/63A61K8/96A61K8/97A61Q1/00A61Q1/10A61Q3/00A61Q3/02A61Q5/00A61Q7/00A61Q19/00A61Q19/08C07J1/00C07J41/00
CPCA61K8/0208A61K8/63A61Q5/006A61Q7/00C07J41/0038A61Q19/007A61Q19/008A61Q19/08C07J1/0011A61Q19/00
Inventor DALKO, MARIACAVEZZA, ALEXANDREPICARD-LESBOUEYRIES, ELISABETHRENAULT, BEATRICEBURNIER, VERONIQUE
Owner LOREAL SA
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