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Adamantanecarboxylic acid benzyl amide derivative compound and skin whitening composition comprising same

A kind of adamantane carboxylic acid benzyl amide and skin whitening technology, which is applied in the preparation of carboxylic acid amide, the preparation of organic compounds, drug combination, etc., can solve the problems of insufficient whitening effect and limited use of stability problems, and solve the problem of fat The effect of excessive solubility increase

Pending Publication Date: 2021-08-20
AMOREPACIFIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, their use is limited due to safety issues on skin, stability issues within dosage forms, and insufficient whitening effect

Method used

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  • Adamantanecarboxylic acid benzyl amide derivative compound and skin whitening composition comprising same
  • Adamantanecarboxylic acid benzyl amide derivative compound and skin whitening composition comprising same
  • Adamantanecarboxylic acid benzyl amide derivative compound and skin whitening composition comprising same

Examples

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preparation example Construction

[0064] The exemplary implementation example of this description is the preparation method of adamantane carboxylic acid benzyl amide derivative compound, as the preparation method of the adamantane carboxylic acid benzyl amide derivative compound, comprising: making adamantane-1-carboxylic acid and Steps in which the hydroxybenzylamine derivative reacts.

[0065] In an implementation example, the hydroxybenzylamine derivative can be selected from 2,4-dihydroxy-benzylbenzylamine, 3,4-dihydroxybenzylamine, 3,5-dihydroxybenzylamine, 2,5 - Any one of the group consisting of dihydroxybenzylamine, 4-hydroxybenzylamine, 3-hydroxybenzylamine and 2-hydroxybenzylamine.

[0066] Specifically, the adamantane-1-carboxylic acid can be dissolved in dichloromethane, and EDC (N-(3-dimethylaminopropyl)-N'ethylcarbodiimide hydrochloride ), in the presence of triethylamine, the hydroxybenzylamine derivative is reacted. In addition, after the reaction is finished, the compound represented by the...

Embodiment 1

[0093] [Example 1] Preparation of adamantane-1-carboxylic acid 2,4-dihydroxy-benzylamide

[0094]

[0095] The adamantane-1-carboxylic acid (1.8g) was dissolved in dichloromethane (50mL), and EDC (N-(3-dimethylaminopropyl)-N'ethyl carbon After diimine hydrochloride, 2.1 g), triethylamine (1.6 mL) and 2,4-dihydroxybenzylamine (1.4 g), it was stirred at normal temperature for 5 hours. After the reaction was completed, the reaction solution was washed with water and a saturated aqueous sodium chloride solution, and then the organic layer was dried with anhydrous magnesium sulfate. After the organic layer was concentrated under reduced pressure by filtration, it was separated by chromatography, whereby the chemical adamantane-1-carboxylic acid 2,4-dihydroxy-benzylamide (1.0 g) was harvested

[0096] 1 H NMR (300MHz, DMSO-d 6 )δ9.56(brs,1H),9.11(brs,1H),7.88(brs,1H),6.79(d,J=7.8Hz,1H),6.21(s,1H),6.15(d,J=7.8 Hz, 1H), 4.05(d, J=5.7Hz, 2H), 1.96~1.65(m, 15H).

Embodiment 2

[0097] [Example 2] Preparation of adamantane-1-carboxylic acid 3,4-dihydroxy-benzylamide

[0098]

[0099] Except having used 3,4-dihydroxybenzylamine instead of 2,4-dihydroxybenzylamine, the objective compound (1.6g) was harvested as a solid by substantially the same method as Example 1.

[0100] 1 H NMR (300MHz, DMSO-d 6 )δ8.71(brs,2H),7.77(brs,1H),6.63~6.59(m,2H),6.44(d,J=7.8Hz,1H),4.07(d,J=5.7Hz,2H), 1.96~1.65(m,15H).

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Abstract

The present specification relates to an adamantanecarboxylic acid benzyl amide derivative compound, an isomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof, and a skin whitening composition comprising same as an active ingredient. Specifically, the compound, according to the present specification, is a compound having a novel structure having adamantanecarboxylic acid bound to an amine compound, and exhibits a skin whitening effect by inhibiting the production of melanin, and thus may be used in various ways as a pharmaceutical composition, a cosmetic composition or a skin preparation for external use.

Description

technical field [0001] Cross References to Related Applications [0002] This application claims priority to Republic of Korea Patent Application No. 10-2019-0001059 filed on January 4, 2019, the entire contents of which are incorporated herein by reference. [0003] This specification discloses an adamantane carboxylic acid benzyl amide derivative compound, its isomer, its pharmaceutically acceptable salt, its hydrate or its solvate and a skin whitening composition containing it. Background technique [0004] The skin has physical and chemical ultraviolet defense factors, which are used to greatly prevent skin disorders caused by various photochemical reactions. The stratum corneum attenuates the energy of UV rays by reflecting and diffusing them. In addition, melanin, SOD (superoxide dismutase; superoxide dismutase), and other antioxidant components absorb ultraviolet rays that penetrate into the skin, attenuate their energy or eliminate secondary active oxygen, thereby ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/40C07C233/60C07C231/02A61K8/42A61Q19/02A61K31/16A61K9/00A61P17/00
CPCA61P17/00A61Q19/02A61K8/42A61K31/165C07C233/60A61K31/16C07C2603/74A61K9/06A61K9/0014A61K47/06C07C235/40A61K2800/43C07C231/02
Inventor 朱泳协高在溁俞载元金容震李泰龙
Owner AMOREPACIFIC CORP