A scalable synthesis of MN-447, an antagonist for integrins αvβ3 and αIIbβ 3

Minoru Ishikawa, Masaki Tsushima, Dai Kubota, Yumiko Yanagisawa, Yukiko Hiraiwa, Yasuo Kojima, Keiichi Ajito, Naomichi Anzai

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

(2S)-Benzeneslfonylamino-3-[3-methoxy-4-{4-(1,4,5,6-tetrahydropyrimidin-2- ylamino)piperidin-1-yl}benzoylamino]propionic acid, MN-447, is a potent antagonist of the integrins αvβ33 and αIIbβ3 Herein, we report a novel synthetic protocol that produces MN-447 in an overall yield of 45%. This protocol, when compared with the original synthetic route for MN-447, is more cost-effective, requires fewer steps, does not require chromatographic purification of intermediates and MN-447, and increases the overall yield by 35%. This report focuses on the synthetic strategies that were developed for this protocol. Now, the large quantities of MN-447 that are needed for preclinical and toxicological studies can be readily obtained.

Original languageEnglish
Pages (from-to)596-602
Number of pages7
JournalOrganic Process Research and Development
Volume12
Issue number4
DOIs
Publication statusPublished - 2008 Jul 1
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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