FXa inhibitor as well as preparation method and application thereof

By introducing pyrrole groups of different amine side chains onto the apixaban core, a novel pyrazolopyridine derivative FXa inhibitor was synthesized, solving the problems of complex synthesis, expensive raw materials, and insufficient safety in the existing technology, and achieving a highly efficient and safe FXa inhibition effect.

CN122444727AActive Publication Date: 2026-07-24QILU SCHOOL OF MEDICINE
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Patent Information

Application Number
CN202610911508.X
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2026-06-24
Publication Date
2026-07-24
Estimated Expiration
2046-06-24

AI Technical Summary

Technical Problem

Existing FXa inhibitors have problems such as complicated synthesis steps, harsh reaction conditions, expensive raw materials and the use of sensitive reagents. They also pose risks of bleeding and individual tolerance differences, and the safety of long-term use needs to be improved.

Method used

A series of pyrazole-pyridine derivatives with different amine side chains introduced onto the benzene ring of the apixaban core were designed and synthesized. FXa inhibitors were prepared through steps such as amide condensation, cycloaddition, and Mannich reaction, avoiding the use of sensitive reagents such as trimethylaluminum and simplifying the synthetic route.

Benefits of technology

An FXa inhibitor with high anticoagulant activity, good pharmacokinetic properties and low bleeding risk was obtained. The synthetic route is simple, the raw materials are inexpensive, the overall yield is high, and a diverse compound library is provided.

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Abstract

The invention belongs to the technical field of pharmaceutical chemicals, and particularly relates to an FXa inhibitor and a preparation method and application thereof. The structural general formula of the FXa inhibitor is shown in the specification, and R1 is shown in the specification. The preparation method of the FXa inhibitor comprises the following steps: taking paranitroaniline as an initial raw material, and sequentially carrying out amide condensation, substitution and cycloaddition to prepare a compound 5; the preparation method comprises the following steps: taking p-anisidine as an initial raw material, and carrying out diazotization, cyclization, elimination and nitro reduction to prepare a compound 10; reacting the compound 10 with 2, 5-dimethoxytetrahydrofuran to obtain a compound 11, carrying out Mannich reaction to obtain an intermediate 12a-12e, and finally carrying out ammonolysis to obtain a compound A01-A05. According to the FXa inhibitor and the preparation method thereof, a novel pyrazolopyridine derivative is synthesized. When the compound is applied to preparation of antithrombotic drugs, efficient anticoagulant activity, good pharmacokinetic properties and low hemorrhage risk are achieved.
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