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A kind of high specific activity tritiated zaltoprofen and its preparation method

An activity and labeling technology, applied in organic chemistry methods, chemical instruments and methods, introduction of heterocyclic compound isotopes, etc., to achieve good chemical stability and metabolic stability, high specific activity, and low price

Active Publication Date: 2021-04-13
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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  • A kind of high specific activity tritiated zaltoprofen and its preparation method
  • A kind of high specific activity tritiated zaltoprofen and its preparation method
  • A kind of high specific activity tritiated zaltoprofen and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1) Take 5g of methyl 2-(3-methoxycarbonylmethyl-4-phenylthiophenyl)propionate, add 100mL of acetonitrile, after it dissolves, add 0.74mL of bromine, and react at 50°C for 10 hours , then distill off acetonitrile, add distilled water 100mL, extract with ethyl acetate (100mL×3), combine the ethyl acetate layers, distill off the solvent to obtain yellow oil 2-(3-methoxycarbonylmethyl-4-(4 -Bromophenylthio) 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 recrystallized fro...

Embodiment 2

[0049] (1) Take 5g of methyl 2-(3-methoxycarbonylmethyl-4-phenylthiophenyl)propionate, add 120mL of acetonitrile, after it dissolves, add 0.74mL of bromine, and react at 35°C for 10 hours , then distill off acetonitrile, add distilled water 100mL, extract with ethyl acetate (100mL×3), combine the ethyl acetate layers, distill off the solvent to obtain yellow oil 2-(3-methoxycarbonylmethyl-4-(4 -Bromophenylthio) 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 recrystallized fro...

Embodiment 3

[0057] (1) Take 5g of methyl 2-(3-methoxycarbonylmethyl-4-phenylthiophenyl)propionate, add 100mL of acetonitrile, after it dissolves, add 0.74mL of bromine, and react at 50°C for 10 hours , then distill off acetonitrile, add distilled water 100mL, extract with ethyl acetate (100mL×3), combine the ethyl acetate layers, distill off the solvent to obtain yellow oil 2-(3-methoxycarbonylmethyl-4-(4 -Bromophenylthio) 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 recrystallized from...

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Abstract

The invention discloses a high specific activity tritium-labeled zaltoprofen and a preparation method thereof, belonging to the technical field of medicine preparation. The present invention takes 2-(3-carboxymethyl-4-phenylthiophenyl) methyl propionate as raw material, generates 4-bromozaltoprofen through bromine substitution, dehydration condensation, hydrolysis three-step reaction, then makes It undergoes tritium-halogen exchange with tritium gas under the action of palladium carbon catalyst and alkali acceptor, and obtains 4- 3 H‑zaltoprofen. The synthesized product was purified by preparative liquid phase to obtain tritiated zaltoprofen with high specific activity (29.30ci / g), high radiochemical purity (≥98%) and high chemical purity (≥99%). 4- prepared by the present invention 3 H‑Zaltoprofen provides a material basis for the research on the absorption, distribution, metabolism and excretion of zaltoprofen in animals.

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 Patents(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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