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A Practical Method for Synthesizing Iptacopan.

Zhiwei Tang1, Shaojie Chu1, Xuesong Wu1

  • 1National Key Laboratory of Lead Druggability Research, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, 285 Gebaini Road, Pudong, Shanghai 201203, China.

Molecules (Basel, Switzerland)
|May 25, 2024
PubMed
Summary
This summary is machine-generated.

A new synthesis route for Iptacopan, a complement factor B inhibitor for PNH treatment, was developed using biocatalysis for key intermediates. This method improves efficiency and provides a foundation for pharmaceutical manufacturing.

Keywords:
Iptacopancomplement pathwayketone reductase

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Area of Science:

  • Pharmaceutical Chemistry
  • Organic Synthesis
  • Biocatalysis

Background:

  • Iptacopan is the first orally available small-molecule complement factor B inhibitor, recently approved for PNH treatment.
  • Existing synthesis details for Iptacopan and its intermediates are limited, primarily to the original patent.
  • There is a need for practical and scalable synthesis routes for pharmaceutical manufacturing.

Purpose of the Study:

  • To develop a practical and efficient synthesis route for Iptacopan.
  • To optimize the synthesis of key intermediates using biocatalysis.
  • To establish a foundation for future pharmaceutical manufacturing of Iptacopan.

Main Methods:

  • Developed a practical synthesis route for Iptacopan through incremental improvements.
  • Employed biosynthesis and enzyme screening (random and site-directed mutagenesis) to obtain a high-yield ketoreductase (M8) for intermediate synthesis.
  • Optimized the synthesis of intermediate 15 from a two-step to a one-step process.

Main Results:

  • Successfully synthesized Iptacopan in a seven-step process with a 29% overall yield.
  • Utilized a biocatalytic method with enzyme M8 to produce a key intermediate with high optical purity (99% ee) and yield.
  • Improved the synthesis of intermediate 15, reducing chiral allosterism risk and enabling scale-up.

Conclusions:

  • A practical and efficient synthesis route for Iptacopan has been established.
  • Biocatalysis offers a viable method for producing chiral intermediates with high purity and yield.
  • The developed synthesis provides a solid foundation for the future pharmaceutical manufacturing of Iptacopan.