Novel compound, and cosmetic composition and pharmaceutical composition comprising the same

A technology of compound and composition, applied in the direction of pharmaceutical combination, cosmetics, organic chemistry, etc., can solve the problems of hyperpigmentation, unevenness, etc., achieve the effect of reducing melanin pigmentation, reducing melanin production, and preventive treatment of hyperpigmentation diseases

Active Publication Date: 2019-12-27
因科斯医药公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Namely, hyperpigmentation induced by activation of protease-activated receptor 2 by trypsin, which can induce hyperpigmentation or uneven skin tone

Method used

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  • Novel compound, and cosmetic composition and pharmaceutical composition comprising the same
  • Novel compound, and cosmetic composition and pharmaceutical composition comprising the same
  • Novel compound, and cosmetic composition and pharmaceutical composition comprising the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0146] Embodiment 1. Synthesis of compound 1

[0147] Step 1. Compound 1a: Synthesis of Fmoc-Lys(Dde)-O-2-chlorotrityl resin (Fmoc-Lys(Dde)-O-2-chloro trityl resin)

[0148]

[0149] Make 2-chlorotrityl chloride resin (2-chloro trityl chloride resin, 100-200 mesh (mesh), Novabiochem 100mg, 1 equivalent) and Fmoc-Lys(Dde)-OH (Nα-Fmoc-Nε-Dde- L-lysine, Nα-Fmoc-Nε-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene) ethyl]-L-lysine (Fmoc-Lys( Dde)-OH(Nα-Fmoc-Nε-Dde-L-lysine, Nα-Fmoc-Nε-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-lysine), 106.5mg, 2 equivalents) and diisopropylamine (DIPEA, 69.7 μL, 4 equivalents) were dissolved in 5 ml of dichloromethane (DCM) and added to a 10 ml reaction vessel, and reacted at normal temperature (23° C.) for 12 hours. The reaction solution was removed by filtration, and the synthesized resin was sequentially washed with 10 ml of dichloromethane, methanol (MeOH), dichloromethane, and dimethylformamide (DMF), respectively, thereby quantitativel...

Embodiment 2

[0163] Embodiment 2: the synthesis of compound 2

[0164] Step 1. Compound 2a: Synthesis of Fmoc-Hyp(tBu)-O-2-chlorotrityl resin (Fmoc-Hyp(tBu)-O-2-chloro trityl resin)

[0165]

[0166] Make 2-chlorotrityl chloride resin (100-200 mesh, Novabiochem 200mg, 1 equivalent) and Fmoc-Hyp(tBu)-OH(Fmoc-O-tert-butyl-L-hydroxyproline) (Fmoc- Hyp(tBu)-OH(Fmoc-O-tert-butyl-L-hydroxyproline), 163.8mg, 2 equivalents) and DIPEA (139.3ul, 4 equivalents) were dissolved in 5ml of dichloromethane and added to a 10ml reaction vessel , and reacted at normal temperature for 12 hours. The reaction solution was removed by filtration, and the synthesized resin was sequentially washed with 10 ml of dichloromethane, methanol, dichloromethane, and dimethylformamide to obtain compound 2a quantitatively.

[0167] Step 2. Compound 2b: Fmoc-Lys(Fmoc)-Hyp(tBu)-O-2-chlorotrityl resin (Fmoc-Lys(Fmoc)-Hyp(tBu)-O-2-chloro trityl resin) synthesis

[0168]

[0169] 5 ml of 20% piperidine (in dimethylforma...

Embodiment 3

[0176] Example 3. Confirmation of tyrosinase inhibitory ability

[0177] In order to analyze whether Compound 1 and Compound 2 obtained in the above examples inhibit tyrosinase activity, a Tyrosinase inhibition assay (Tyrosinase inhibition assay) was carried out.

[0178] As a specific experimental method, mushroom tyrosinase (Mushroom tyrosinase) was diluted to 2 units / ul in 0.1M sodium phosphate buffer (Sodium phosphate buffer), and tyrosine (Tyrosine) was dissolved in Water becomes 0.03% by weight. Each experimental group described in Table 1 below was also diluted to 10 ppm, 100 ppm, 1000 ppm, and 10000 ppm in 0.1 M sodium phosphate buffer, and mixed as shown in Table 1. React at 37° C. for 1 hour and measure the absorbance (wavelength: 490 nm, Epoch spectrophotometer, BioTek, USA). Based on this result, calculation was performed as the tyrosinase inhibition rate compared to the control group.

[0179] show the result in figure 2 middle.

[0180] as from figure 2 A...

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Abstract

The invention relates to a novel compound, and a cosmetic composition and a pharmaceutical composition comprising the same. Disclosed are a novel compound, and a cosmetic composition for whitening anda pharmaceutical composition for preventing and treating a melanin hyperpigmentation disorder by activating autophagy to induce melanosome degradation and also by effectively inhibiting endocytosis of keratinocytes to interfere melanosome transfer into keratinocytes, thereby expressing an excellent effect on improvement, prevention, and treatment of a hyperpigmentation disorder induced from melanin.

Description

technical field [0001] The present invention relates to a novel compound, a cosmetic composition containing the same, and a pharmaceutical composition. More specifically, it relates to a novel compound that induces decomposition of melanosomes by activating autophagy and inhibits endocytosis into keratinocytes, and a composition containing the same. Cosmetic composition for skin whitening and pharmaceutical composition for preventing and treating hypermelanosis. Background technique [0002] Skin color roughly depends on the amount of melanin, hemoglobin, carotene, etc., of which melanin plays the most important role. Melanin not only determines the color of human skin, but also protects the skin. However, when excessive melanin is produced in the skin due to external environmental changes such as excessive exposure to ultraviolet rays, air pollution, stress, and inflammation, pigmentation occurs. It also becomes the cause of darkening of skin color or formation of dark spo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/068C07K5/037A61K8/64A61Q19/02A61K38/05A61K38/06A61P17/00
CPCC07K5/06086C07K5/0215A61K8/64A61Q19/02A61P17/00A61K38/00C07D207/16
Inventor 郑和志高溟镐金兴载金星遇尹硕贞郑朱延申嘉荣郑世奎朴基燉
Owner 因科斯医药公司
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