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Clarithromycin derivatives and its preparation process and pharmaceutical application

A technology of clarithromycin and derivatives, applied in the field of derivatives of clarithromycin, can solve problems such as clarithromycin 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

[0019] 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 clarithromycin

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0110] Example 1 clarithromycin-2'-ethylsuccinate

[0111] method one

[0112] Clarithromycin 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, then stirred in an ice bath for 30 minutes, and then stirred overnight at room temperature . Add 0.3g of sodium citrate, adjust the pH value of the reaction aqueous solution between 8.0-9.0 with NaOH solution, stir for half an hour, the solution is layered, take the organic layer and add diatomaceous earth, filter, and the filtrate is cooled to 10- Add about 40ml of water at 15°C, a white solid precipitates out of the solution, filter, wash with cold acetone, and dry the filter cake in an oven at 50-60°C to obtain 6.2g of white solid with a yield of 88.3%.

[0113] The solid was recrystallized in acetone to obtain white crystals with a melting point of 217-222°C.

[0114] Method Two

[...

example 2

[0120] Example 2 clarithromycin-2'-propionate

[0121] method one

[0122] Clarithromycin 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, 3.0g 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, adjust the pH value of the reaction aqueous solution between 8.0-9.0 with NaOH solution, stir for half an hour, the solution is layered, take the organic layer and add diatomaceous earth, filter, and the filtrate is cooled to 10- Add about 40ml of water at 15°C, a white solid precipitates out of the solution, filter, wash with cold acetone, and dry the filter cake in an oven at 50-60°C to obtain 5.5g of white solid with a yield of 85.9%.

[0123] Method Two

[0124] Dissolve 6.0g of clarithromycin in 30ml of THF with stirring, add 5.0g of propionic anhydride, add dropwise 0.5ml of concent...

example 3

[0125] Example 3 clarithromycin-2'-isobutyrate

[0126] method one

[0127] Clarithromycin 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, 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 76.2%.

[0128] Method Two

[0129]Dissolve 6.0g of clarithromycin in 30ml of THF with stirring, add 5.0g of isobutyric anhydride, dropwise add 0.5ml of concentrated sulfuric acid, stir and react for 3h, then add about 40ml ...

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Abstract

The invention relates to Clarithromycin derivatives, the preparing process and medicinal use, the Clarithromycin derivatives have general formulas of (I), (II), these compounds and the medicinal compositions of them can be used for treating infectious diseases caused by sensitive organisms and other pathogenic agents.

Description

technical field [0001] The present invention relates to derivatives of clarithromycin, in particular to compounds of general formula (I) and (II) and their preparation methods, and pharmaceutical compositions containing one or more of these compounds, as well as the compounds and their pharmaceutical compositions Application in the treatment of infectious diseases caused by sensitive bacteria and other pathogens. [0002] Background technique [0003] Clarithromycin is a semi-synthetic 14-membered ring macrolide antibiotic, its chemical name is 6-O-methyl erythromycin, that is, the hydroxyl group at the 6-position in the erythromycin molecule is replaced by a methoxy group , so it is also called clarithromycin. Clarithromycin can penetrate the bacterial wall and reversibly combine with the ribosomal 50s subunit, block transpeptidation and translocation, thereby effectively terminating chain elongation, inhibiting RNA-dependent protein synthesis, and producing antibacteri...

Claims

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Application Information

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IPC IPC(8): C07H17/08A61K31/7048A61K9/00A61P31/04
CPCY02A50/30
Inventor 王庆利
Owner 济南思创生物技术有限公司
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