Mydrial derivates,preparation method of mydrial derivates and cosmetics or skin medicinal composition

A compound and derivative technology, applied in the field of new tyramide derivatives, can solve problems such as side effects and difficulty in application

Inactive Publication Date: 2008-05-21
SEDERMA SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these products are difficul

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  • Mydrial derivates,preparation method of mydrial derivates and cosmetics or skin medicinal composition
  • Mydrial derivates,preparation method of mydrial derivates and cosmetics or skin medicinal composition
  • Mydrial derivates,preparation method of mydrial derivates and cosmetics or skin medicinal composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0420] Example 1: Synthesis of N-succinyl-tyramide (compound II)

[0421] To a solution of tyramine hydrochloride (1.00 g; 5.76 mmol) in 20 ml THF was added 1 equivalent of potassium carbonate (K 2 CO 3 ) (0.80 g; 5.76 mmol) and 1.04 equivalents of succinic anhydride (0.60 g; 5.99 mmol). After stirring overnight at room temperature, water (10 ml) was added to hydrolyze the mixture, and 4 g of succinic resin IR120 (R-SO 3 H) Wash and stir for 15 minutes (pH=0-1). After filtering and washing with water, THF was evaporated coldly. 0.92 g (3.88 mmol; 67.3%) of N-succinyl-tyramide precipitated out as white crystals.

[0422] C 12 h 15 NO 4

[0423] MM=237.257gmol -1

[0424] Melting point: 135-136°C

[0425] CHN: Calculated: 60.75% C; 6.35% H; 5.90% N

[0426] Measured value: 61.33%C; 6.05%H; 5.86%N

[0427] Infrared spectrum: 3313; 3055; 2930; 1694; 1643; 1542; 1517; 1426; 1238;

[0428] 1208cm -1

Embodiment 2

[0429] Embodiment 2: the synthesis of N-toluenesulfonyl-tyramide (compound III)

[0430] Add 1 equivalent of potassium carbonate (K 2 CO 3 ) (0.16 g; 1.16 mmol) and 1.10 equivalents of tosyl chloride (0.12 g; 1.27 mmol). After stirring overnight at room temperature, water (4ml) was added to hydrolyze the mixture, and 4g of succinic resin IR 120 (R-SO3 H) Wash and stir for 1 hour. After filtering and washing with water, the solvent THF was then cold evaporated and the solid was filtered off. 0.19 g (0.65 mmol; 56.00%) of N-tosyl-tyramide precipitated out as white crystals.

[0431] C 15 h 17 NSO 3

[0432] MM=291.37gmol -1

[0433] Melting point: 169-172°C

[0434] CHN: Calculated: 61.83% C; 5.88% H; 4.81% N

[0435] Measured value: 61.94%C; 5.83%H; 4.78%N

[0436] Infrared spectrum: 3335; 3220; 1613; 1598; 1515; 1435; 1312; 1229; 1149; 1063; 913; 833; 812cm -1

Embodiment 3

[0437] Embodiment 3: the synthesis of N, N'-two-tyramine-urea (compound IV)

[0438] To a solution of tyramine hydrochloride (0.20 g; 1.15 mmol) in 4 ml THF was added 1 equivalent of potassium carbonate (K 2 CO 3 ) (0.16 g; 1.16 mmol) and 0.54 equivalents of carbonyl-diimidazole (0.10 g; 0.62 mmol). After two days of stirring at room temperature, the mixture was hydrolyzed by adding water (4ml) and THF (4ml), and 4g of succinic resin IR 120 (R-SO 3 H) Wash and stir for 15 minutes. After filtering and washing with 4 ml THF and then 4 ml water, the solvent was evaporated cold and the solid was filtered off. 0.09 g (0.27 mmol; 43.20%) of N,N'-di-tyramine-urea precipitated out as white crystals.

[0439] C 17 h 20 N 2 o 3

[0440] MM=300.3605gmol -1

[0441] Melting point: 95-98°C

[0442] Mass spectrometry: (m / z) = 301.2 [M+H] +

[0443] CHN: Calculated: 67.98% C; 6.71% H; 9.33% N

[0444] Measured value: 67.66%C; 6.73%H; 9.36%N

[0445] Infra Red: 3336; 3104; 293...

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Abstract

The invention relates to a novel tyramine derivate and a method for preparing the compound. The invention also relates to a cosmetic or medical skin composition having the compound, as well as the application of the compound in the skin care field, in particular to the application in order to release the over-pigmentation.

Description

technical field [0001] The present invention relates to novel tyramide derivatives, their use, cosmetic or pharmaceutical compositions containing said substances, processes for the preparation of these compounds, and their use in skin care, in particular for the reduction of hyperpigmentation. Background technique [0002] The natural pigmentation mechanism of the skin is now well documented: Melanocytes present in the stratum basale epidermidis produce melanin, which is synthesized in the melanin body. Under ultraviolet light, the synthesis of melanin (melanogenesis) increases. The physiological function of this browning of the skin is to protect the skin from UV exposure. [0003] Dysfunctions of various melanogenesis mechanisms (due to external aggressions, hormonal disturbances or aging) lead to the appearance of brown spots, especially freckles (spots), and the formation of sun spots or age spots. [0004] Altering the natural pigmentation of the skin is a common aspi...

Claims

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Application Information

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IPC IPC(8): C07C235/74C07C311/17C07C275/24A61K8/40A61K8/46A61Q1/02
Inventor 卡尔·林特纳
Owner SEDERMA SA
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