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Method for preparing tritium-labeling aditoprim

A labeling and acid anhydride technology, which is applied in the field of preparation of tritium-labeled ediprine, can solve the problems of high cost of radioactive waste, long half-life, environmental pollution and the like, and achieves a simple and easy synthesis route, reduced environmental pollution and high chemical purity. Effect

Active Publication Date: 2015-04-22
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 1. 14 C mark raw materials have a long production cycle, are expensive, and are not easy to obtain
[0006] 2. 14 C has a long half-life, high cost of radioactive waste, and serious environmental pollution

Method used

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  • Method for preparing tritium-labeling aditoprim
  • Method for preparing tritium-labeling aditoprim
  • Method for preparing tritium-labeling aditoprim

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030](1) Add 60mL of dichloromethane, 8.0g (26.5mmol) of elliprine and 1.0g (41mmol) of sodium hydride that have been treated in advance into a 100mL round bottom equipped with a magnet, stir to dissolve and add dichloromethane Tert-butyl dicarbonate (BOC anhydride) 11.5g (53.0mmol), stirred at 25°C for 12 hours, poured the reaction solution into 50mL ice water, extracted in a separatory funnel, took the dichloromethane layer, added anhydrous sulfuric acid After drying with sodium, it was filtered, concentrated under reduced pressure and recrystallized with a small amount of ethyl acetate to obtain 8.5 g of BOC-protected ideproline.

[0031] (2) Dissolve 4g (8mmol) of BOC anhydride-protected ideproline obtained in step (1) in 50mL of dichloromethane, and dissolve 2.53g (16mmol) of liquid bromine in 10mL of dichloromethane. (0~5°C), it was slowly added dropwise into dichloromethane of elliprine, and after the dropwise addition was completed, it was stirred and reacted for 4 ho...

Embodiment 2

[0036] (1) Add 60mL of tetrahydrofuran, 8.0g (26.5mmol) of ideproline and 1.0g (41mmol) of sodium hydride that have been treated in advance into a 100mL round bottom equipped with a magnet, stir to dissolve and add di-tert-butyl Base dicarbonate (BOC anhydride) 23.0g (105.5mmol), stirred and reacted at 25°C for 12 hours, poured the reaction solution into 200mL ice water, extracted with dichloromethane in a separatory funnel, took the dichloromethane layer, added After drying with sodium sulfate, it was filtered, concentrated under reduced pressure, and then recrystallized with a small amount of ethyl acetate to obtain 8.1 g of BOC-protected ideproline.

[0037] (2) Dissolve 4g (8mmol) of BOC anhydride-protected ideproline obtained in step (1) in 50mL of dichloromethane, and dissolve 2.53g (16mmol) of liquid bromine in 10mL of dichloromethane. (0~5°C), it was slowly added dropwise into dichloromethane of elliprine, and after the dropwise addition was completed, it was stirred a...

Embodiment 3

[0042] (1) Add 60mL of tetrahydrofuran, 8.0g (26.5mmol) of ideproline and 2.12g (53mmol) of sodium hydroxide to a 100mL round bottom equipped with a magnet, stir and dissolve, then add di-tert-butyl dicarbonate (BOC anhydride) 23.0g (105.5mmol), stirred and reacted at 25°C for 12 hours, poured the reaction liquid into 200mL ice water, extracted with dichloromethane in a separating funnel, took the dichloromethane layer, added anhydrous sodium sulfate to dry Afterwards, it was filtered, concentrated under reduced pressure, and then recrystallized with a small amount of ethyl acetate to obtain 7.8 g of BOC-protected ideproline.

[0043] (2) Dissolve 4g (8mmol) of BOC anhydride-protected ideproline obtained in step (1) in 50mL of dichloromethane, and dissolve 2.53g (16mmol) of liquid bromine in 10mL of dichloromethane. (0~5°C), it was slowly added dropwise into dichloromethane of elliprine, and after the dropwise addition was completed, it was stirred and reacted for 4 hours at 2...

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Abstract

The invention belongs to the field of radiochemical synthesis, and particularly relates to a method for preparing tritium-labeling aditoprim. The aditoprim is used as a raw material, after the aditoprim is subjected to amino protection, a bromination reaction is conducted on the aditoprim, 2-bromine-aditoprim is obtained, then Pd / C is used as a catalyst, tritium-halogen exchange is conducted between the 2-bromine-aditoprim and halogen, and the tritium-labeling aditoprim with a high radiochemical purity being larger than or equal to 99.2%, a high chemical purity being larger than or equal to 99% and a high specific activity being 34.4 Ci / g is obtained. According to the method, a material base is provided for search and discovery of a pharmacology and toxicology effect target in the body of a new drug aditoprim and disposal of absorption, distribution, metabolis, excretion and the like of the new drug aditoprim in animal bodies, and reference is also provided for isotope labeling of drugs of the similar structures is also provided.

Description

technical field [0001] The invention belongs to the field of radiochemical synthesis, and in particular relates to a preparation method of tritium-labeled ideproline. The present invention uses the radioactive isotope tritium to position and mark the 2-position of the benzene ring of the antibacterial synergist drug Erdipoline to obtain tritium-labeled Erdipoline, which is used for the search and discovery of the pharmacological and toxicological targets of Erdipoline in vivo and The study of its disposition (absorption, distribution, metabolism and excretion) in animals provides the necessary material basis. Background technique [0002] Eldipoline antibacterial synergist drugs have broad antibacterial spectrum, good antibacterial activity, rapid absorption, high bioavailability, strong tissue penetration ability, high peak concentration, long elimination half-life, large apparent volume of distribution, and It has the characteristics of wide distribution and long-lasting ...

Claims

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Application Information

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IPC IPC(8): C07D239/49
CPCC07D239/49
Inventor 袁宗辉王立业潘源虎黄玲利王玉莲陶燕飞陈冬梅谢书宇郝海红程古月王旭彭大鹏刘振利
Owner HUAZHONG AGRI UNIV
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