Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF1 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these tumor angiogenesis inhibitors have great advantages, there are still some problems in practical application, such as the dependence of some tumors on angiogenesis, drug resistance, adverse reactions and toxicity caused by mutation and compensatory tumor signal transduction.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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
Comparison scheme
Effect test

Embodiment 1

[0105] Example 1 Synthesis of N-(3-((1H-1,2,4-triazole-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 cool down to -5~5°C, add 5ml of KOH (1.2g, 20mmol) aqueous solution, stir for 5min, then add t-butanol peroxide dropwise - BuOOH (1.8 g, 10 mmol) in DMSO 2 ml. After stirring at room temperature for about 2 hours, the reaction was complete. The solution was poured into 50ml of 1M hydrochloric acid solution, and a light yellow solid precipitated. After filtering, the filter cake was dried and weighed to obtain 1.38g of crude product. After recrystallization, 1.20 g of pure product was obtained, which was light yellow and had a melting point of 166-168°C. The resulting 4-nitro-1-naphthol (1.89 g 10 mmol) was dissolved in 20 ml CH 3 In OH, hydrogen gas was introduced under 10 atmospheres, an...

Embodiment 2

[0121] Example 2 N-(3-((1H-1,2,4-triazole-5-)thio)-4-hydroxynaphthalene-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 cool down to -5~5°C, add KOH (1.2g, 20mmol) in 5ml aqueous solution, stir for 5min, then add tert-butanol peroxide dropwise - BuOOH (1.8 g, 10 mmol) in 2 ml DMSO. Stir at room temperature for about 2 hours. After the reaction is complete, pour the solution into 50ml of 1mol / L hydrochloric acid solution, a light yellow solid precipitates, filter, and weigh the filter cake to obtain 1.38g of crude product after drying. After recrystallization, 1.20 g of pure product was obtained, which was light yellow and had a melting point of 166-168°C.

[0127] The obtained 4-nitro-1-naphthol (189g, 10mmol) was dissolved in 20ml CH 3 In OH, stirred and reacted for 10 hours under 10 atmospheric p...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com