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Hydrazone amide derivative and pharmaceutical composition

A compound and hydrate technology, applied in the field of biomedicine, can solve the problems of genetic and reproductive toxicity, and achieve the effect of simple structure, good safety and low toxicity

Active Publication Date: 2021-07-13
SHENZHEN CELL INSPIRE PHARM DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, both minoxidil and finasteride drugs have been shown to have significant drawbacks so far
Topical application of minoxidil can cause a certain degree of side effects to occur, such as rash, local inflammation, headache, hirsutism, etc., while oral application of finasteride has been established to produce potentially negative effects on sexual life. Hormone dysfunction, genetic and reproductive toxicity

Method used

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  • Hydrazone amide derivative and pharmaceutical composition
  • Hydrazone amide derivative and pharmaceutical composition
  • Hydrazone amide derivative and pharmaceutical composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Synthesis of embodiment 1 hydrazone amide derivatives

[0087]

[0088] The synthetic routes of hydrazone amide derivatives are shown above. Substituted acetoacetic acid, dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP) and substituted alcohol or ammonia were added to dichloromethane, and stirred at room temperature for 8 h. The solvent was removed using a rotary evaporator, and purified by column chromatography to obtain the corresponding acetoacetamide or acetoacetate.

[0089] Add ammonia with different substitutions to methanol, add the same amount of hydrochloric acid and sodium nitrite, stir at room temperature for 0.5 hours, then add substituted acetoacetamide or acetoacetate, stir at room temperature for 10 hours, and filter to obtain the desired hydrazone Amide derivatives.

Embodiment 2

[0090] The synthesis of embodiment 2 compound 1

[0091] According to the method described in Example 1, 186 mg of ethyl 2-amino-4-methylthiazole-5-carboxylate, 206 mg of DCC, 10 mg of DMAP and 102 mg of 3-oxobutyric acid were reacted together to obtain 200 mg Ethyl-4-methyl-2-acetoacetylthiazolamine-5-carboxylate, yield 74%.

[0092] 135 mg of ethyl-4-methyl-2-acetoacetylthiazolamine-5-carboxylate, 0.5 ml of 1M hydrochloric acid, 34 mg of sodium nitrite and 70 mg of 2-aminobenzoic acid were reacted together to obtain 150 mg of the compound 1. The yield is 72%.

Embodiment 3

[0093] The synthesis of embodiment 3 compound 2

[0094] According to Example 1, 186 mg of ethyl 2-amino-4-methylthiazole-5-carboxylate, 206 mg of DCC, 10 mg of DMAP and 102 mg of 3-oxobutyric acid were reacted together to obtain 200 mg of Ethyl-4-methyl-2-acetoacetylthiazolamine-5-carboxylate, yield 74%.

[0095] 135 mg of ethyl-4-methyl-2-acetoacetylthiazolamine-5-carboxylate, 0.5 ml of 1M hydrochloric acid, 34 mg of sodium nitrite and 70 mg of 4-aminobenzoic acid were reacted together to obtain 160 mg of the compound 2. The yield is 77%.

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PUM

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Abstract

The invention provides a brand-new hydrazone amide derivative and a pharmaceutical composition containing the same, the hydrazone amide derivative has a structural formula as shown in formula (I), and is a brand-new compound capable of stimulating hair follicle growth and preventing and treating alopecia. The hydrazone amide derivative provided by the invention has high hair follicle growth stimulation activity and low toxicity. As a novel compound type, the compound can be used for preventing and treating alopecia.

Description

technical field [0001] The invention relates to the field of biomedicine, in particular, the invention relates to hydrazone amide derivatives and pharmaceutical compositions containing them. Background technique [0002] Alopecia is a skin disorder characterized by the loss of hair. There are many types of it, including alopecia areata, pseudoalopecia areata, alopecia areata, total alopecia, hair loss caused by mental factors, hair loss caused by nutritional element deficiency, seborrheic alopecia, alopecia caused by drug chemotherapy, androgenetic alopecia, etc. Human hair not only has biological and physiological functions, but also has important psychological and sociological functions because the thickness of hair and hairstyle have obvious effects on human appearance. At present, with the improvement of living standards, people's requirements for beauty are becoming increasingly urgent. Since hair loss affects appearance, it negatively affects the patient's psychology...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/56C07D417/12C07D277/46C07D277/82C07D213/75C07D211/58C07D217/06C07D295/185C07C251/76C07C249/16A61P17/14A61K31/426A61K31/428A61K31/192A61K31/4402A61K31/44A61K31/4468A61K31/472A61K31/5375
CPCC07D211/58C07D217/06C07D295/185C07D213/75C07D277/82A61P17/14C07D277/56C07D417/12C07D277/46C07C251/76C07D295/192C07D213/85
Inventor 黄丹娥赵超顾琼徐峻
Owner SHENZHEN CELL INSPIRE PHARM DEV CO LTD