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Compound as well as synthesis method and application thereof

A compound and manufacturing method technology, applied in the directions of active ingredients of heterocyclic compounds, chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, etc. lower problem

Inactive Publication Date: 2018-11-02
TECHNODERMA MEDICINES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these two hair regeneration drugs are not ideal for hair growth and their drug side effects make the patient usage rate low, which cannot meet the needs of hair loss patients
[0005] However, with the development of the times, the diseases on the hair are becoming more and more prominent. Therefore, in order to meet the needs of modern people, the research on the diversification and diversity of related drugs, the development of drugs to promote hair regeneration treatment and control alopecia remain to be done. Further in-depth and expansion, patients need more effective, less side effects, and convenient external hair regeneration drugs

Method used

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  • Compound as well as synthesis method and application thereof
  • Compound as well as synthesis method and application thereof
  • Compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Embodiment 1, product number TDM-105842

[0102] 2-(3,5-dichloro-4-(3-(4-methyl-1H-pyrazole-2-methyl)-4-hydroxyphenoxy)phenyl)-1,2,4-tri Oxazine-3,5(2H,4H)-dione

[0103] Structural formula:

[0104]

[0105] synthetic route:

[0106]

[0107] Specific synthesis method:

[0108] Step 1: Synthesis of 1,3-dichloro-2-(4-methoxyphenoxy)-5-nitrobenzene

[0109]

[0110] Dissolve 4-methoxyphenol (5.5 g, 44 mmol) in DMF (100 mL) and add NaH (2.64 g, 66 mmol), stir for half an hour and add 1,2,3-trichloro-5-nitrobenzene (10 g, 44mmol). The reaction solution was heated to 120°C for three hours. The reaction was completed and cooled to room temperature, then concentrated. The residue was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to obtain the crude product, and then column chromatography (0-10% ethyl acetate and petroleum ether) gave the product (5.0 g, 36%).

[0111] In this step, different reaction condi...

Embodiment 2

[0160] 2-(3,5-dichloro-4-(3-(4,4'-difluoro-cyclohexyl-2-methyl)-4-hydroxyphenoxy)phenyl)-1,2,4- Triazine-3,5(2H,4H)-dione

[0161] Structural formula:

[0162]

[0163] m / z 499[M+H] +

Embodiment 3

[0165] 2-(3,5-dichloro-4-(3-(1P-cyclohexyl-2-methyl)-4-hydroxyphenoxy)phenyl)-1,2,4-triazine-3,5 (2H,4H)-Diketone

[0166] Structural formula:

[0167]

[0168] m / z 481[M+H]+

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Abstract

The invention provides a compound. The compound is characterized by comprising a structure shown in the description. The novel small-molecule compound can be used for promoting regrowth of hair when applied for external use, and can be used for treating androgen genotype alopecia, seborrheic alopecia or alopecia caused by chemotherapy and other various factors.

Description

technical field [0001] The present invention relates to the field of chemical synthesis, in particular to a chemical compound and its synthesis method and application. Background technique [0002] Hair growth is a cyclic process that repeats three growth stages: anagen (anagen), middle anagen (catagen) and telogen (dormant). During the anagen phase, hair bulb keratinocytes (HBK) proliferate and differentiate vigorously, resulting in elongated growth of the hair shaft. However, affected by various factors such as environment, autogenous metabolism, mental stress, work pressure, decreased immunity and genetic factors, these factors may lead to the degeneration of hair follicle cells, resulting in the gradual stop of hair growth, hair thinning and even loss. For example, pathological stimulation of stress or androgen may lead to hair follicle cycle disorders, including shortening of the anagen phase, degeneration of hair follicle cells, and prolongation of the telogen phase, ...

Claims

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Application Information

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IPC IPC(8): C07D403/12C07D253/075C07F9/6521C07F9/6568C07F9/50A61K31/53A61K31/675A61P5/14A61P17/14
CPCA61P5/14A61P17/14C07D253/075C07D403/12C07F9/5004C07F9/65683C07F9/65685
Inventor 曹小冬陆丰平樊毅超毛晨王增全
Owner TECHNODERMA MEDICINES
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