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Ortho-aminobenzoic acid derivative and application thereof

An anthranilic acid and derivative technology, which is applied in the directions of drug combination, cosmetic preparations, cosmetics, etc., can solve the problems of inability to completely remove dandruff, unsatisfactory effect, unsatisfactory effect and the like

Pending Publication Date: 2020-06-19
福建莲珂科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many kinds of lotion products currently used to treat dandruff, but the curative effect is not satisfactory, it is easy to relapse, and it is impossible to completely remove dandruff
The antifungal drugs clinically used to treat dandruff include ketoconazole, selenium disulfide, etc. Long-term use will bring side effects to the body, and it is easy to repeat and has certain dependence. Moreover, it is effective in removing dandruff and conditioning hair. The effect is not ideal

Method used

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  • Ortho-aminobenzoic acid derivative and application thereof
  • Ortho-aminobenzoic acid derivative and application thereof
  • Ortho-aminobenzoic acid derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of methyl octanoyl anthranilate

[0040]

[0041] 102g of methyl anthranilate and 93g of triethylamine were dissolved in 500ml of dichloromethane, cooled to -10°C, 100g of octanoyl chloride was dissolved in 500ml of dichloromethane, and added dropwise to the aforementioned mixture. Below 0°C, after the dropwise addition, the temperature was raised to room temperature, and the reaction was continued for 1 h. 500 ml of water was added to the reaction solution, and the layers were separated. The organic phase was washed twice with 500 ml of water, and the organic phase was concentrated to remove dichloromethane to obtain 138 g of a solid product. Yield 81%.

[0042] Synthesis of Octanoylanthranilic Acid

[0043]

[0044] Add 100g of methyl octanoyl anthranilate, add 200ml of ethanol, 300ml of water, 29g of sodium hydroxide, heat up to 50°C, stir until the solid is completely dissolved, continue to react at 50°C for 1 hour, the hydrolysis of the methyl este...

Embodiment 2

[0049] Synthesis of Methyl Lauroyl Anthranilate

[0050]

[0051]76g of methyl anthranilate and 69g of triethylamine were dissolved in 500ml of dichloromethane, cooled to -10°C, 100g of lauroyl chloride was dissolved in 500ml of dichloromethane, and added dropwise to the aforementioned mixture. The dropping process controlled the temperature at Below 0°C, after the dropwise addition, warm up to room temperature, continue the reaction for 1 h, add 500 ml of water to the reaction solution, separate layers, wash the organic phase with 500 ml of water twice, concentrate the organic phase to remove dichloromethane, and obtain 140 g of solid product, Yield 91.9%.

[0052] Synthesis of Lauroyl Anthranilic Acid

[0053]

[0054] Add 100g of methyl lauroyl anthranilate, add 200ml of ethanol, 300ml of water, 24g of sodium hydroxide, heat up to 50°C, stir until the solid is completely dissolved, continue to react at 50°C for 1 hour, the hydrolysis of the methyl ester is complete, ...

Embodiment 3

[0056] Synthesis of Methyl Palmitoyl Anthranilate

[0057]

[0058] Dissolve 60.4g of methyl anthranilate and 55g of triethylamine in 500ml of dichloromethane, cool down to -10°C, dissolve 100g of palmitoyl chloride in 500ml of dichloromethane, add dropwise to the aforementioned mixture, and control the temperature during the dropping process Below 0°C, after the dropwise addition, warm up to room temperature, continue the reaction for 1 h, add 500 ml of water to the reaction liquid, separate layers, wash the organic phase twice with 500 ml of water, concentrate the organic phase to remove dichloromethane, and obtain 107 g of solid product , yield 75.5%.

[0059] Synthesis of Palmitoylanthranilic Acid

[0060]

[0061] Add 100g of methyl lauroyl anthranilate, add 200ml of ethanol, 300ml of water, and 20.5g of sodium hydroxide, heat up to 50°C, stir until the solid is completely dissolved, continue to react at 50°C for 1 hour, the hydrolysis of the methyl ester is comple...

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Abstract

The invention relates to the technical field of cosmetics and medicines, in particular to an ortho-aminobenzoic acid derivative compound and application thereof. By preparing a series of compounds with an anti-inflammatory function, the obtained anti-inflammatory compound can be used for preparing cosmetic reagents or pharmaceutical reagents, and the cosmetic reagents and the pharmaceutical reagents are not specifically limited. For example, the cosmetic can be a smoothing toner, a nutritional toner, a massage cream, an emollient, a gel, a nutritional cream, a mask, a gel or a shower gel shampoo and other washing type cosmetics, and can also be a cream, ointment, cream, plaster or spray and other similar pharmaceutical preparation products. The compound can be used for a sensitive skin andcan also be added to infant and child cosmetics to reduce irritation.

Description

technical field [0001] The invention relates to the technical field of cosmetics and medicines, in particular to a class of anthranilic acid derivative compounds and applications thereof. Background technique [0002] With the advancement of modern technology and the improvement of people's living standards, people's pursuit of a healthy and beautiful appearance is becoming more and more intense. Urban pollution, industrial waste gas, ultraviolet radiation, the use of unqualified cosmetics and the abuse of various beauty treatment equipment are also increasingly harmful to our skin. According to statistics, allergic dermatitis is the most common cosmetic skin disease, and its incidence rate accounts for 81.5% of the total incidence of cosmetic skin diseases. Allergies seem to be a nightmare that people follow on the road of pursuing health and beauty. Glucocorticoids are usually used for the treatment of sensitive or allergic skin with multiple erythema, papules, desquamat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/54A61K8/42A61P17/00A61P17/04A61P37/08A61Q5/00A61Q19/00A61P29/00
CPCC07C233/54A61K8/42A61Q19/00A61Q5/006A61P37/08A61P17/04A61P17/00A61P29/00
Inventor 滕景斌吴峰肖永堂
Owner 福建莲珂科技有限公司
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