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Uses of dithiolane compounds for the photoprotection of the skin, dithiolane compounds and compositions containing same

一种二硫戊环、化合物的技术，应用在二硫戊环化合物用于皮肤光防护的用途；新型二硫戊环化合物；含有它们的组合物领域，能够解决防护不完全令人满意等问题

Inactive Publication Date: 2010-03-31
LOREAL SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the protection provided by these active agents against UVA sun-induced depletion of GSH is still not entirely satisfactory

Method used

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  • Uses of dithiolane compounds for the photoprotection of the skin, dithiolane compounds and compositions containing same
  • Uses of dithiolane compounds for the photoprotection of the skin, dithiolane compounds and compositions containing same
  • Uses of dithiolane compounds for the photoprotection of the skin, dithiolane compounds and compositions containing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0365] Example 1: Synthesis of 4-methyl-1,2-dithiolane-4-carboxylic acid (compound 1)

[0366]

[0367] 8 g of dichloropivalic acid were placed in a 250 ml three-necked flask equipped with a condenser and a dropping funnel. Dissolve the acid in 80 mL of water and slowly add 4.6 g of Na 2 CO 3 . 10.7 g of potassium thioacetate solution are added dropwise and the reaction medium is brought to reflux. Added 14.9 g Na 2 CO 3 , and then reflux the medium. After the starting material disappeared, 7.3 mL of DMSO was added, followed by reflux. Dithiolane was obtained by precipitation after acidification and drying the solid under vacuum.

[0368] 1H NMR (400MHz, DMSO-d6): δppm 3.69(d, 2H), 2.95(d, 2H), 1.53(s, 3H), ESI-:

[0369] [(M,H)-]=163m / z

Embodiment 2

[0370] Example 2: Synthesis of 4-methyl-1,2-dithiolane-4-carboxylic acid octyl ester (compound 9)

[0371]

[0372] 1 g of acid (24) followed by 0.8 ml of 1-chloro-N,N,2-trimethyl-propenylamine (27) was placed in 20 ml of dichloromethane in a 100 ml three-necked flask using a syringe. The mixture was stirred for 1 hour and then added dropwise via an addition funnel to the -5°C reaction medium containing 1.28 ml triethylamine, 0.96 ml octanol and 20 ml dichloromethane. Stir the mixture. The reaction medium was then washed with water (3 x 30 ml). The aqueous phase was extracted with 3 x 10 mL EtOAc. The combined organic phases were washed with 30 mL of saturated NaCl aqueous solution, then washed with NaCl 2 SO 4 Dry, filter and concentrate under vacuum (500 mbar, T=40°C) on a rotary evaporator. The obtained crude product was a yellow oil (m = 1.25 g), which was purified by flash chromatography on a silica column (m SiO 2 = 40 g, eluting with a gradient of 100 / 0 and t...

Embodiment 3

[0378] Example 3: 4-methyl-1,2-dithiolane-4-thiocarboxylic acid S-[2-(acetylamino)ethyl] Synthesis of Esters (Compound 13)

[0379]

[0380] The same method as Example 2: the nucleophile used was N-acetyl cysteamine (0.64 ml).

[0381] Purification by flash chromatography on a silica column (m SiO 2 = 40 g; eluted with a linear gradient of 100 / 0 followed by 98 / 2 DCM / MeOH).

[0382] After concentrating the fractions on a rotary evaporator (P=200 mbar, T=40° C.), 0.32 g of a mixture of the expected product and N,N,2-trimethylpropanamide (28) are obtained.

[0383] Viscous yellow liquid, yield = 10%; Rf (expected) = 0.3; eluent:

[0384] 95 / 5 DCM / MeOH; 1H NMR (DMSO-d6): δppm8.03 (t, NH), 3.57 (d, 2H), 3.18 (dt 2H), 3.10 (d, 2H), 2.96 (m, 2H) , 1.79(s, 3H), 1.43(s, 3H); MS m / z (M+, 266; M+23, 288).

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Abstract

The present invention provides uses of dithiolane compounds for the photoprotection of the skin, dithiolane compounds and compositions containing same. The present invention relates to cosmetic use ofat least one dithiolane compound (I) in a composition comprising a medium, to strengthen and / or preserve the natural antioxidant protection of face skin against oxidative stress preferably caused byUV radiation.

Description

technical field [0001] The present invention relates to the use of specific dithiolane compounds of formula (I) in compositions useful in the field of treatment or prevention of disorders induced by oxidative stress, especially by solar radiation, and to combinations containing them things. Background technique [0002] The skin is the outermost organ of our body and is therefore the primary target of environmental stressors, most notably typified by the sun's ultraviolet radiations UVB and UVA. In particular, acute or chronic sun exposure is known to induce harmful biological and clinical effects on the body. [0003] Skin damage caused by chronic exposure (repeated irradiation) or polar exposure (intensive irradiation) of UV-A or UV-B has been extensively studied; especially known: [0004] - UV-B rays with the highest energy wavelength (290-300 nm; 5% of total UV) affect epidermal cells (keratinocytes) most especially by acting on DNA; [0005] - Penetrating deeper UV-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K8/49A61K31/385A61K31/4025A61Q17/04A61Q19/08A61P17/18C07D339/04C07D409/06
CPCA61K2800/522A61K8/4986C07D339/04A61Q17/04A61Q19/08A61P17/00A61P17/16A61P17/18A61P43/00
Inventor X·马拉特K·卢塞特-莱瓦尼尔
Owner LOREAL SA
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