Novel method for producing 3-methyl-1,2,4-thiadiazole-5-carbohydrazide

JPWO2025009476A1Pending Publication Date: 2025-01-09
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Patent Information

Application Number
JP2025531529
Authority / Receiving Office
JP · JP
Patent Type
Applications
Priority Date
2023-07-03
Filing Date
2024-06-28
Publication Date
2025-01-09

AI Technical Summary

Technical Problem

Current methods for producing 3-methyl-1,2,4-thiadiazole-5-carbohydrazide, a key intermediate for fezolinetan, face challenges such as the use of dangerous reagents, low yield, and sulfur impurities, making it difficult to scale up safely and efficiently.

Method used

A method involving the reaction of a compound with an alkali metal cyanide in an aprotic polar solvent, followed by an alcohol and subsequent acid hydrolysis, which eliminates the need for toxic carbon monoxide and improves yield, using organic bases like triethylamine and solvents like N,N-dimethylformamide.

Benefits of technology

This method allows for the safe and efficient production of 3-methyl-1,2,4-thiadiazole-5-carbohydrazide with high yield, avoiding the limitations of previous methods and enabling scalable synthesis of fezolinetan.

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Abstract

The present invention addresses the problem of providing a method for producing 3-methyl-1,2,4-thiadiazole-5-carbohydrazide with good safety and good yield. The present invention relates to a method for producing 3-methyl-1,2,4-thiadiazole-5-carbohydrazide or a salt thereof via a compound represented by formula (2): (In the formula, R denotes an alkyl group having 1-4 carbon atoms) or a salt thereof, which is a novel compound. The present invention is capable of providing a method for producing, with good safety and good yield, 3-methyl-1,2,4-thiadiazole-5-carbohydrazide that is an important synthesis intermediate for fezolinetant which is useful as a drug for treating sex hormone-dependent diseases.
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