High-specific-activity tritium-labeled zaltoprofen and preparation method thereof

A technology with high activity and high ratio, applied in the field of high specific activity tritium-labeled zaltoprofen and its preparation, achieves the effect of low price, good chemical stability and metabolic stability, and short half-life

Active Publication Date: 2019-12-20
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no study on the process of radioactive isotope-labeled zaltoprofen in animals, especially in food animals

Method used

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  • High-specific-activity tritium-labeled zaltoprofen and preparation method thereof
  • High-specific-activity tritium-labeled zaltoprofen and preparation method thereof
  • High-specific-activity tritium-labeled zaltoprofen and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1) Take 5g of methyl 2-(3-methoxycarbonylmethyl-4thiophenyl)propionate, add 100mL of acetonitrile, add 0.74mL of bromine after it dissolves, and react at 50°C for 10 hours, then Acetonitrile was evaporated, 100 mL of distilled water was added, extracted with ethyl acetate (100 mL×3), the ethyl acetate layers were combined, and the solvent was evaporated to obtain yellow oil 2-(3-methoxycarbonylmethyl-4-(4-bromo Phenylthio)phenyl)methyl propionate, yield 95%;

[0042] (2) Get 4g of methyl 2-(3-methoxycarbonylmethyl-4-(4-bromophenylthio)phenyl)propionate obtained in step (1), add 30g polyphosphoric acid (PPA), add Anhydrous sodium carbonate 0.5g, heat up to 98°C, stir and react for 10 hours, observe the formation of black viscous, stop the reaction, after cooling to room temperature, add water 100mL, ethyl acetate 200mL and stir for 10 minutes, let stand and separate , take the upper organic phase, evaporate the ethyl acetate to obtain a brown solid substance, which is ...

Embodiment 2

[0049] (1) Take 5g of methyl 2-(3-methoxycarbonylmethyl-4thiophenyl)propionate, add 120mL of acetonitrile, add 0.74mL of bromine after it dissolves, and react at 35°C for 10 hours, then Acetonitrile was evaporated, 100 mL of distilled water was added, extracted with ethyl acetate (100 mL×3), the ethyl acetate layers were combined, and the solvent was evaporated to obtain yellow oil 2-(3-methoxycarbonylmethyl-4-(4-bromo Phenylthio)phenyl)methyl propionate, yield 94%;

[0050] (2) Get 4g of methyl 2-(3-methoxycarbonylmethyl-4-(4-bromophenylthio)phenyl)propionate obtained in step (1), add 25g polyphosphoric acid (PPA), add Anhydrous sodium carbonate 0.5g, heat up to 95°C, stir and react for 10 hours, observe the formation of black viscous, stop the reaction, after cooling to room temperature, add water 100mL, ethyl acetate 200mL and stir for 10 minutes, let stand and separate , take the upper organic phase, evaporate the ethyl acetate to obtain a brown solid substance, which is ...

Embodiment 3

[0057] (1) Take 5g of methyl 2-(3-methoxycarbonylmethyl-4thiophenyl)propionate, add 100mL of acetonitrile, add 0.74mL of bromine after it dissolves, and react at 50°C for 10 hours, then Acetonitrile was evaporated, 100 mL of distilled water was added, extracted with ethyl acetate (100 mL×3), the ethyl acetate layers were combined, and the solvent was evaporated to obtain yellow oil 2-(3-methoxycarbonylmethyl-4-(4-bromo Phenylthio)phenyl)methyl propionate, yield 95%;

[0058] (2) Get 4g of methyl 2-(3-methoxycarbonylmethyl-4-(4-bromophenylthio)phenyl)propionate obtained in step (1), add 25g polyphosphoric acid (PPA), add Anhydrous sodium carbonate 0.5g, heat up to 98°C, stir and react for 8 hours, observe the formation of black viscous, stop the reaction, after cooling to room temperature, add water 100mL, ethyl acetate 200mL and stir for 10 minutes, let stand and separate , take the upper organic phase, evaporate the ethyl acetate to obtain a brown solid substance, which is r...

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Abstract

The invention discloses high-specific-activity tritium-labeled zaltoprofen and a preparation method thereof, and belongs to the technical field of medicine preparation. According to the method, 2-(3-carboxymethyl-4-phenylthiophenyl)methyl propionate is used as a raw material, and is subjected to three-step reaction of bromine substitution, dehydration condensation and hydrolysis to generate 4-bromo zaltoprofen, the 4-bromo zaltoprofen and tritium gas are subjected to tritium-halogen exchange under the actions of a palladium-carbon catalyst and an alkali acceptor to prepare 4-<3>H-zaltoprofen,and the synthesized product is subjected to preparation liquid phase purification to obtain tritium-labeled zaltoprofen with high specific activity (29.30 ci / g), high radiochemical purity (greater than or equal to 98%) and high chemical purity (greater than or equal to 99%). According to the invention, the prepared 4-<3>H-zaltoprofen provides a material basis for researching the absorption, distribution, metabolism and excretion of zaltoprofen in an animal body.

Description

technical field [0001] The invention belongs to the technical field of medicine preparation, in particular to a tritium-labeled zaltoprofen with high specific activity and a preparation method thereof. Background technique [0002] Zaltoprofen (Zaltoprofen I), chemically named 10,11-dihydro-alpha-methyl-10-oxo-dibenzo[b,f]thiazem-2-acetic acid, was developed by Chemiphar Corporation of Japan A non-steroidal anti-inflammatory drug, which was first launched in Japan on September 1, 1993. [0003] Zaltoprofen is a non-steroidal anti-inflammatory drug with anti-inflammatory, analgesic and antipyretic effects, and has a strong effect on acute inflammation. Zaltoprofen is well absorbed orally, and there is no drug accumulation after repeated administration. It is widely used clinically to control infection or non-infection inflammation and pain. Studies have shown that the antipyretic, analgesic and anti-inflammatory effects of zaltoprofen on rats and mice are equal to or strong...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D337/14C07B59/00
CPCC07B59/002C07B2200/05C07D337/14
Inventor 袁宗辉潘源虎赵欢欢戴梦红瞿玮谢书宇陶燕飞陈冬梅刘振利谢长清
Owner HUAZHONG AGRI UNIV
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