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Azithromycin derivatives and its preparation process and pharmaceutical application

A technology of azithromycin and derivatives, applied in the field of macrolide drugs, can solve problems such as azithromycin taste bitter

Inactive Publication Date: 2006-09-27
济南思创生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] However, the above methods can only correct or cover part of the bitter taste, and cannot fundamentally solve the problem of the bitter taste of azithromycin

Method used

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  • Azithromycin derivatives and its preparation process and pharmaceutical application
  • Azithromycin derivatives and its preparation process and pharmaceutical application
  • Azithromycin derivatives and its preparation process and pharmaceutical application

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0110] Example 1 Azithromycin-2'-propionate

[0111] method one

[0112] Azithromycin 6.0g, dissolved in 20ml THF, 4.8g K 2 CO 3 A solution made of 22ml of water was added, the mixture was stirred and cooled to 5-10°C, 5.0g of propionyl chloride was added over 40 minutes, stirred in an ice bath for 30 minutes, and then stirred overnight at room temperature. Add 0.3g of sodium citrate, use NaOH solution to adjust the pH value of the reaction aqueous solution between 8.0-9.0, and stir for half an hour, the solution is layered, take the organic layer, concentrate to obtain a white solid, add ether to dissolve the solid, and heat Wash, cool and filter, and dry the filter cake in an oven at 30-40°C. The weight of the white solid is 5.2 g, and the yield is 81.0%.

[0113] Method Two

[0114] Dissolve 6.0 g of azithromycin in 30 ml of THF with stirring, add 5.0 g of propionic acid, dropwise add 1.0 ml of dimethyl sulfoxide, stir for 7 hours, adjust the pH value of the reaction a...

example 2

[0119] Example 2 Azithromycin-2'-ethylsuccinate

[0120] method one

[0121] Azithromycin 6.0g, dissolved in 20ml THF, 4.8g K 2 CO 3 A solution made of 22ml of water was added, the mixture was stirred and cooled to 5-10°C, 3.7g of succinic monoethyl chloride was added over 40 minutes, stirred in an ice bath for 30 minutes, and then stirred at room temperature for 24 Hour. Add 0.3g of sodium citrate, adjust the pH value of the reaction aqueous solution between 9.0-9.5 with NaOH solution, and stir for half an hour, the solution is layered, the organic layer is taken, concentrated to obtain 6.0g of white waxy solid, the yield 86%.

[0122] Method Two

[0123] Dissolve 6.0g of azithromycin in 30ml of THF with stirring, add 4.0g of monoethyl succinate, dropwise add 1.0ml of dimethyl sulfoxide, stir and react for 7h, adjust the pH value of the reaction aqueous solution between 8.0-9.0 with NaOH solution Then, about 40ml of water was added to precipitate a solid, which was filt...

example 3

[0126] Example 3 Azithromycin-2'-isobutyrate

[0127] method one

[0128] Azithromycin 6.0g, dissolved in 20ml THF, 4.8g K 2 CO 3 A solution made of 22ml of water was added, the mixture was stirred and cooled to 5-10°C, 5.0g of isobutyryl chloride was added over 40 minutes, stirred in an ice bath for 30 minutes, and then stirred overnight at room temperature. Add 0.3g of sodium citrate, use NaOH solution to adjust the pH value of the reaction aqueous solution between 8.0-9.0, and stir for half an hour, the solution is layered, take the organic layer, concentrate to obtain a white solid, add ether to dissolve the solid, and heat Wash, cool and filter, and dry the filter cake in an oven at 30-40°C. The weight of the white solid is 5.0 g, and the yield is 76.5%.

[0129] Method Two

[0130] Dissolve 6.0g of azithromycin in 30ml of THF with stirring, add 5.0g of isobutyric anhydride, dropwise add 0.5ml of concentrated sulfuric acid, stir for 3 hours, then add about 40ml of wa...

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Abstract

The invention discloses an Azithromycin derivant and preparing method and medicinal application relating to macrolides medicine, which also relates to medicinal compositions with one or a plurality of Azithromycin derivants and the application of compound and medicinal compositions in treating communicable disease from sensitized bacteria and other causal agents.

Description

technical field [0001] The present invention relates to macrocyclic lactone drugs, in particular to derivatives of azithromycin and preparation methods thereof, and pharmaceutical compositions containing one or more of these compounds, and the compounds and pharmaceutical compositions thereof are useful in the treatment of sensitive bacteria and other pathogens Applications in infectious diseases. Background technique [0002] Azithromycin is a 15-membered ring macrolide, the first variety of azolides. Its mechanism of action is the same as that of erythromycin. It mainly binds to the 50S subunit of bacterial ribosomes and inhibits RNA-dependent protein synthesis. Azithromycin has good antibacterial effect on Streptococcus pyogenes, Streptococcus pneumoniae and influenza bacillus, and also has antibacterial activity on Staphylococcus. The antibacterial effect of azithromycin on Gram-positive cocci such as Staphylococcus and Streptococcus is slightly worse than that of eryt...

Claims

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Application Information

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IPC IPC(8): C07H17/00A61K31/7052A61K9/00A61P31/04
CPCY02A50/30
Inventor 王庆利
Owner 济南思创生物技术有限公司
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