2-sulfo-4-amino-1-naphthol derivative and preparation method and application thereof

A technology of naphthol derivatives and derivatives, applied in drug combinations, pharmaceutical formulations, active ingredients of heterocyclic compounds, etc., can solve the problems of tumors' low dependence on angiogenesis, drug resistance, adverse reactions, etc.

Inactive Publication Date: 2012-11-07
QILU PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although these tumor angiogenesis inhibitors have great advantages, there are still some problems in practical application, such as the dependen

Method used

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  • 2-sulfo-4-amino-1-naphthol derivative and preparation method and application thereof
  • 2-sulfo-4-amino-1-naphthol derivative and preparation method and application thereof
  • 2-sulfo-4-amino-1-naphthol derivative and preparation method and application thereof

Examples

Experimental program
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Effect test

Example Embodiment

[0105] Example 1 Synthesis of N-(3-((1H-1,2,4-triazol-5-)thio)-4-hydroxynaphthalene-1-yl)naphthalene-2-carboxamide (Compound 1) :

[0106]

[0107] Compound 1

[0108] 1) Synthesis of 4-amino-1-naphthol:

[0109]

[0110] Dissolve 1-nitronaphthalene (0.86g, 5mmol) in 13ml DMSO and lower the temperature to -5~5℃, add 5ml of KOH (1.2g, 20mmol) aqueous solution, stir for 5min, add t-butanol peroxy -BuOOH (1.8g, 10mmol) in 2ml of DMSO solution. After stirring at room temperature for about 2 hours, the reaction was complete. The solution was poured into 50ml of 1M hydrochloric acid solution. A light yellow solid precipitated out, filtered, and the filter cake was dried and weighed to obtain 1.38g of crude product. After recrystallization, 1.20 g of pure product was obtained, light yellow, and melting point 166-168°C. Dissolve the obtained 4-nitro-1-naphthol (1.89g 10mmol) in 20ml CH 3 In the OH, hydrogen gas was introduced under 10 atmospheres, and the reaction was stirred for 12 hour...

Example Embodiment

[0121] Example 2 N-(3-((1H-1,2,4-triazole-5-)sulfanyl)-4-hydroxynaphthalen-1-yl)-4-bromo-2-fluorobenzenesulfonamide ( Compound 11) Synthesis:

[0122]

[0123] Compound 11

[0124] 1) Synthesis of 4-amino-1-naphthol

[0125]

[0126] Dissolve 1-nitronaphthalene (0.86g, 5mmol) in 13ml DMSO and lower the temperature to -5~5℃, add 5ml aqueous solution of KOH (1.2g, 20mmol), stir for 5min, add t-butanol peroxy -BuOOH (1.8g, 10mmol) in 2ml DMSO. Stir at room temperature for about 2 hours. After the reaction is complete, pour the solution into 50 ml of 1 mol / L hydrochloric acid solution. A pale yellow solid is precipitated, filtered, and the filter cake is dried and weighed to obtain 1.38 g of crude product. After recrystallization, 1.20 g of pure product was obtained, light yellow, and melting point 166-168°C.

[0127] The obtained 4-nitro-1-naphthol (189g, 10mmol) was dissolved in 20ml CH 3 In OH, the reaction was stirred under 10 atmospheres of hydrogen for 10 hours. TLC detected that...

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Abstract

The invention belongs to the field of pharmaceutical chemicals, and in particular relates to a 2-sulfo-4-amino-1-naphthol derivative and pharmaceutically acceptable salt thereof, a solvate of the derivative, and a solvate of the pharmaceutically acceptable salt. The invention also relates to a preparation method, a medical composition and application of the 2-sulfo-4-amino-1-naphthol derivative. The 2-sulfo-4-amino-1-naphthol derivative has a good tyrosine kinase inhibiting effect and low toxicity and has great significance for the clinical treatment of tumor.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and specifically relates to a class of 2-thio-4-amino-1-naphthol derivatives, pharmaceutically acceptable salts thereof, solvates of the derivatives and the pharmaceutically acceptable Solvates of accepted salts. The present invention also relates to the preparation method of the 2-thio-4-amino-1-naphthol derivative, its pharmaceutical composition and the use of the derivative. Background technique [0002] Tumor is one of the main diseases that seriously threaten human life and health. According to the statistics of the World Health Organization, about 6.9 million patients die of tumors all over the world every year. Due to changes in living environment and living habits, under the influence of adverse environment and some unfavorable factors, the incidence and mortality of tumors have gradually increased in recent years. [0003] In the past, the treatment of tumors was achieved ...

Claims

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Application Information

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IPC IPC(8): C07D249/12C07D473/38A61K31/4196A61K31/52A61P35/00A61P35/04
Inventor 徐文方徐福明张磊王晶翼范传文杨康辉
Owner QILU PHARMA
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