Cysteine derivatives

A technology of cysteine ​​and derivatives, which is applied in the field of cosmetics and external skin pharmaceuticals, and can solve problems such as side effects, unsatisfactory effects, and low photostability

Inactive Publication Date: 2006-06-07
AJINOMOTO CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these compounds have problems such as unsatisfactory degree of their effects, strong toxicity to cells, low photostability, etc.
Furthermore, regarding anti-inflammatory agents and retinoic acid, there is also the problem of side effects as described above

Method used

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  • Cysteine derivatives
  • Cysteine derivatives
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Examples

Experimental program
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Effect test

Synthetic example 1

[0065] Synthesis Example 1: Synthesis of Cystine Diamide Derivatives

[0066] To 7 ml of acetonitrile, 0.15 g of L-cystine diamide dihydrochloride, 0.21 g of n-hexanoic anhydride, and 0.10 g of triethylamine were sequentially added, and the mixture was stirred at room temperature overnight. The crude crystals obtained by concentrating the reaction solution were purified by high-speed liquid chromatography (HPLC fractionation with an apparatus for high-speed liquid chromatography manufactured by Hitachi Co., Ltd. using "Ina-Tosil ODS-3 column" (manufactured by GL Scientific Corporation)) to obtain N,N'-bis(n-hexanoyl)-L-cystine diamide 0.18g. In the same way, various N,N'-diacyl-L-cystine diamides were obtained. These are novel compounds that are not documented in the literature. The mass spectrometry results of these compounds are listed in Table 1 below.

[0067] New compounds

Synthetic example 2

[0068] Synthesis Example 2: Synthesis of cystine dialkyl ester derivatives

[0069] To 25 ml of acetonitrile, 0.50 g of L-cystine dimethyl dihydrochloride, 0.55 g of n-valeric anhydride, and 0.31 g of triethylamine were sequentially added, and the mixture was stirred at room temperature overnight. The crude crystals obtained by concentrating the reaction solution were purified by the same high-speed liquid chromatography as in Synthesis Example 1, to obtain 0.38 g of N,N'-bis(n-valeryl)-L-cystine dimethyl ester. In the same way, various N,N'-diacyl-L-cystine dialkyl esters or N,N'-diacyl-DL-homocysteinyl dialkyl esters were obtained.

[0070] Secondly, reveal the test example.

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Abstract

Provides an oxidative stress inhibitor that can inhibit the expression of harmful proteins and the activation of gene transcription regulators related thereto, and shows a good sense of use and high safety, thereby providing oxidative stress-induced or promoted skin aging A method for preventing, delaying, improving or treating a change in skin cosmetics or an adverse change in skin cosmetics; and a cosmetic or skin external preparation containing an oxidative stress inhibitor as an active ingredient; the oxidative stress inhibitor is characterized in that it contains from One or two or more selected from cysteine, cystine derivatives, and salts thereof are used as active ingredients.

Description

[0001] This application is a divisional application of the PCT China application with the application number 99810287.3. Technical field [0002] The present invention relates to an oxidative stress inhibitor that can be used to prevent, delay, ameliorate, or treat diseases caused by oxidative stress or skin damage or disease, or an oxidative stress inhibitor using such an oxidative stress inhibitor Methods, and cosmetics and external skin agents containing such oxidative stress inhibitors as effective ingredients. Background technique [0003] In recent years, research on the etiology of diseases caused by oxidative stress such as ultraviolet rays, active oxygen, and free radicals, or skin injuries or diseases, has been active. For example, in terms of aging, canceration, edema, pigmentation, etc., as the cause, it is known to be closely related to noxious cytokines such as IL-1α and TNF-α or extracellular matrix degrading enzymes such as collagenase (for example, "Skin Oxidative...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/60A61K8/02A61K8/35A61K8/368A61K8/37A61K8/41A61K8/44A61K8/45A61K8/46A61K8/49A61K8/60A61K8/63A61K8/67A61K8/86A61K31/16A61P17/18A61Q1/02A61Q17/04A61Q19/00A61Q19/02A61Q19/08A61Q19/10
CPCA61K8/02A61K8/0212A61K8/35A61K8/368A61K8/37A61K8/411A61K8/447A61K8/45A61K8/46A61K8/494A61K8/60A61K8/63A61K8/676A61K8/678A61K8/86A61Q1/02A61Q17/04A61Q19/00A61Q19/004A61Q19/02A61Q19/08A61Q19/10C07C323/60A61P17/16A61P17/18
Inventor 岩崎敏治北泽学盐尻荣二坂本一民
Owner AJINOMOTO CO INC
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