Pilot Scale Synthesis of a Novel Nonpeptide Angiotensin II Receptor Antagonist

FR143187 is a novel nonpeptide angiotensin II receptor antagonist under development at Fujisawa Pharmaceutical Co. for the treatment of hypertension. Development of a process for preparation on a large scale is described. The optimized process is 10 steps in length and uses only commercially availab...

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Bibliographic Details
Published in:Organic process research & development 1998-07, Vol.2 (4), p.230-237
Main Authors: Zanka, Atsuhiko, Nishiwaki, Masanori, Morinaga, Yasuhiro, Inoue, Takayuki
Format: Article
Language:English
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Summary:FR143187 is a novel nonpeptide angiotensin II receptor antagonist under development at Fujisawa Pharmaceutical Co. for the treatment of hypertension. Development of a process for preparation on a large scale is described. The optimized process is 10 steps in length and uses only commercially available materials for each step. Efficient methylation of the 2-position of a pyrrole derivative was achieved by reduction of a Mannich base via the quaternary ammonium salt. Selective cyanation directed by a solvent effect was also investigated. Process improvement efforts focused on optimized reaction conditions for each step, leading to a high-quality product according to a new and concise synthetic route.
ISSN:1083-6160
1520-586X
DOI:10.1021/op9800055