A simple stereoselective synthesis and biological evaluation of FR181157: orally active prostacyclin mimetic

Kouji Hattori; Seiichiro Tabuchi; Osamu Okitsu; Kiyoshi Taniguchi

doi:10.1016/j.bmcl.2003.09.054

A simple stereoselective synthesis and biological evaluation of FR181157: orally active prostacyclin mimetic

Bioorg Med Chem Lett. 2003 Dec 15;13(24):4277-9. doi: 10.1016/j.bmcl.2003.09.054.

Authors

Kouji Hattori¹, Seiichiro Tabuchi, Osamu Okitsu, Kiyoshi Taniguchi

Affiliation

¹ Medicinal Chemistry Research Laboratories, Fujisawa Pharmaceutical Co. Ltd, 1-6, Kashima 2-Chome, Yodogawa-Ku, Osaka, Japan. kouji_hattori@po.fujisawa.co.jp

PMID: 14643308
DOI: 10.1016/j.bmcl.2003.09.054

Abstract

Synthetic method of a novel prostaglandin (PG) mimetic: FR181175 without PG skeleton are described. The key to success is creation of a chiral epoxide using Sharpless AD reaction with high ee yield. FR181157 shows high potency and agonist efficacy at the IP receptor and has good bioavailability.

MeSH terms

Administration, Oral
Animals
Area Under Curve
Epoprostenol / administration & dosage
Epoprostenol / chemical synthesis
Epoprostenol / pharmacokinetics*
Fasting
Models, Molecular
Molecular Conformation
Oxazoles / administration & dosage
Oxazoles / chemical synthesis
Oxazoles / pharmacokinetics*
Stereoisomerism
Structure-Activity Relationship

Substances

Oxazoles
FR181157
Epoprostenol