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Derivative of new benzothiadiazines, preparation method and usage

A benzothiadiazine and a technology for its application are applied in the field of benzothiadiazine compounds and their preparation, and can solve the problems of elevated blood sugar, low tissue selectivity and the like

Active Publication Date: 2007-12-26
北京赛德维康医药研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Diazoxide has antihypertensive and cardioprotective effects, but it also has disadvantages such as hyperglycemia, hypotension, and low tissue selectivity

Method used

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  • Derivative of new benzothiadiazines, preparation method and usage
  • Derivative of new benzothiadiazines, preparation method and usage
  • Derivative of new benzothiadiazines, preparation method and usage

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: Preparation N-{[2-(acetamide) phenyl] sulfonyl} acetamide

[0050] Add 34.4g of anthranilamide, 70ml of acetic anhydride, and 35ml of pyridine into a 250ml three-necked reaction flask, stir and heat, and react at 40°C to 100°C for 3 hours. The solution is reddish brown. During the reaction The material gradually precipitated again, cooled to below 0°C, filtered, rinsed with cold ethanol three times, and recrystallized from ethanol to obtain 43 g of N-{[2-(acetamide)phenyl]sulfonyl}acetamide. Melting point: 195.6-195.9°C, yield 84.0%.

Embodiment 2

[0051] Embodiment 2: Preparation of N-{[2-(acetamide)-4-chlorophenyl]sulfonyl}acetamide

[0052] Get 41.3g 4-chloro-2-aminobenzenesulfonamide, the acetic anhydride of 70ml, the pyridine of 35ml, preparation method is the same as embodiment 1, obtains N-{[2-(acetamide)-4-chlorophenyl]sulfonyl } Acetamide 51g. Melting point: 217.1-218.2°C, yield: 81.7%.

Embodiment 3

[0053] Example 3: Preparation of 7-chloro-2,3-methyl-2H-1,2,4-benzothiadiazine-1,1-diox (compound code 2001)

[0054] Take 7-chloro-3-methyl-2H-1,2,4-benzothiadiazine-1,1-dioxygen 7g, anhydrous potassium carbonate 12.5g, acetonitrile 80ml, add it into a 250ml three-necked reaction flask, Add dropwise the mixed solution of 13.7g methyl iodide and 10ml acetonitrile under stirring, raise the temperature, keep the temperature at about 55°C, react for 3 hours, recover the solvent under reduced pressure, pour the reaction solution into 200ml water, stir for 10 minutes, filter, A khaki solid was obtained, which was recrystallized from 200 ml of ethanol to obtain 6.5 g of light yellow solid 7-chloro-2,3-methyl-2H-1,2,4-benzothiadiazine-1,1-dioxine. Melting point: 235.7-236.2°C, yield 83.3%.

[0055] Prepare the following compounds in the same way:

[0056] 7-Chloro-3-methyl-2-ethyl-2H-1,2,4-benzothiadiazine-1,1-dioxo, melting point: 200.6-201.1°C, yield 65.0%. (Compound code 2002) ...

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Abstract

This invention relates to benzothiadiazine compounds, their preparation method, composition containing the compounds, and the application of the compounds as KATP channel modulators in treating diseases related to central nervous system, cardiovascular system, lung system, gastrointestinal system and endocrine system.

Description

field of invention [0001] The present invention relates to benzothiadiazines and their preparation methods, compositions containing these compounds and these compounds as K ATP The use of the channel modulator in the treatment of diseases, such as the use in the treatment of diseases of the central nervous system, cardiovascular system, respiratory system, gastrointestinal system and endocrine system. Background technique [0002] Potassium channels play an important role in membrane potential. Among the different types of potassium channels, one is ATP-sensitive (K ATP )aisle. K has been found ATP Channels exist in a variety of tissue cells, such as: cardiomyocytes, pancreatic cells, skeletal muscle, smooth muscle, central neurons and pituitary cells. This channel is involved in various cellular functions such as secretion of hormones (insulin from pancreatic beta cells, growth hormone and prolactin from pituitary cells), vasodilation (in smooth muscle cells), cardiac a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/24A61K31/549A61P9/00A61P9/12A61P9/08A61P25/00A61P1/00A61P11/00A61P13/00
Inventor 汪海杨永林金俊华
Owner 北京赛德维康医药研究院
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