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Preparation method for high-purity tedizolid phosphate

A technology of tedizolid phosphate and tedizolid, which is applied in the field of preparation of high-purity tedizolid phosphate, can solve the impact of tedizolid phosphate application effect and production efficiency, and it is difficult to obtain high-purity tedizolid phosphate. Problems such as poor stability of dizolid phosphate and phosphorus oxychloride intermediates have achieved high market promotion value, easy promotion and application, and less post-processing procedures

Active Publication Date: 2015-12-09
JINAN ASIA PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Dimer impurities are easily produced during the reaction process of starting material 1 and phosphorus oxychloride, and the resulting phosphorus oxychloride intermediate has poor stability, and is prone to degradation and polymerization during the process of obtaining phosphoric acid esters by hydrolysis of phosphorus oxychloride, and easily produces pyrophosphoric acid. Phosphoric acid and other impurities, the purification process is cumbersome, many procedures, low production efficiency, and it is not easy to obtain high-purity tedizolid phosphate, which has a serious impact on the application effect and production efficiency of tedizolid phosphate

Method used

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  • Preparation method for high-purity tedizolid phosphate
  • Preparation method for high-purity tedizolid phosphate
  • Preparation method for high-purity tedizolid phosphate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 37.0g tedizolid, 400ml tetrahydrofuran, and 12.9g DIPEA into a three-necked flask, and ice-bath until the inner temperature is 0 o C, stir, slowly drop 15.3g phosphorus oxychloride, control temperature o C, after the dropwise addition, naturally warming up to 20 oC , continue to stir for 4h, TLC detects that the raw material disappears, and a solution of the phosphoryl chloride tedizolid intermediate is obtained.

[0027] Add 25.9g DIPEA to the upper solution, cool to 0 o C, stir, slowly drop 21.6g benzyl alcohol, control the temperature o C, after the dropwise addition, naturally warming up to 20 oC , continue to stir for 8h, TLC detects that the raw materials disappear, filter, add 200ml ethyl acetate to the filter cake for recrystallization, filter, and filter the cake at 40 oC Vacuum drying for 10 hours gave a total of 52.3 g of dibenzyl phosphate tedizolid intermediate, with a yield of 83%. The nuclear magnetic resonance data of the dibenzyl phosphate tedizo...

Embodiment 2

[0030] Add 74.1g tedizolid, 800ml tetrahydrofuran, and 25.9g DIPEA into the three-necked flask, and ice-bath until the inner temperature is 0 o C, stir, slowly drop 30.7g phosphorus oxychloride, control temperature o C, after the dropwise addition, naturally warming up to 20 oC , continue to stir for 4h, TLC detects that the raw material disappears, and a solution of the phosphoryl chloride tedizolid intermediate is obtained.

[0031] Add 51.7g DIPEA to the upper solution, cool to 0 o C, stir, slowly drop 43.3g benzyl alcohol, control the temperature o C, after the dropwise addition, naturally warming up to 20 oC , continue to stir for 8h, TLC detects that the raw materials disappear, filter, add 400ml ethyl acetate to the filter cake for recrystallization, filter, and filter the cake at 40 oC Vacuum drying for 10 hours gave a total of 105.9 g of dibenzyl phosphate tedizolid intermediates, with a yield of 84%. The nuclear magnetic resonance data of the dibenzyl phosphate te...

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Abstract

The invention discloses a preparation method for high-purity tedizolid phosphate. The method is characterized by comprising the following steps: subjecting starting materials tedizolid and phosphorus oxychloride to a reaction so as to produce a tedizolid phosphorus oxychloride intermediate; then reacting the tedizolid phosphorus oxychloride intermediate with benzyl alcohol so as to produce a tedizolid dibenzyl phosphate intermediate; and carrying out debenzylation under the action of a catalyst so as to obtain tedizolid phosphate. Meanwhile, all the parameters of procedures are systematically adjusted. The introduced dibenzyl phosphate intermediate has good stability; benzyl protection removal reaction conditions are mild; compared with conventional preparation methods for tedizolid, by-reactions and generation of impurities are greatly reduced in the invention; the purity of the prepared tedizolid phosphate can reach more than 99.9%; and the preparation method omits the step of product purification, has more simplified steps and improves preparation efficiency of the tedizolid phosphate.

Description

technical field [0001] The invention relates to the technical field of preparation of pharmaceutical compounds, in particular to a preparation method of high-purity tedizolid phosphate. Background technique [0002] Tedizolid phosphate, the chemical name is ((R)-3-(3-fluoro-4-(6-(2-methyl-2H-tetrazolium-5-)pyridine-3-)phenyl) -2-oxazolinone-5-)methyl diphosphate, the molecular formula is C 17 h 16 FN 6 o 6 P, the structural formula is as follows: [0003] . [0004] Tedizolid phosphate is a lyophilized powder and tablet drug for injection developed by CubistPharms, which is anti-gram-positive bacteria including Staphylococcus aureus, methicillin-resistant and methicillin-sensitive strains, Streptococcus pyogenes, Streptococcus agalactiae, Streptococcus angina (including Streptococcus angina, Streptococcus intermedius, and Streptococcus stellatus), and Enterococcus faecalis. The indication is acute bacterial skin and skin structure infection (ABSSSI) caused by sensit...

Claims

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Application Information

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IPC IPC(8): C07F9/6558
Inventor 彭立增朱富强
Owner JINAN ASIA PHARMA TECH
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