Synthesis and evaluation of prodrugs of corticotropin-releasing factor-1 (CRF1) receptor antagonist BMS-665053 leading to improved oral bioavailability

Bioorg Med Chem Lett. 2017 Mar 15;27(6):1360-1363. doi: 10.1016/j.bmcl.2017.02.015. Epub 2017 Feb 10.

Abstract

A series of phosphate and ester-based prodrugs of anilinopyrazinone 1 (BMS-665053) containing either a methylene or an (acyloxy)alkoxy linker was prepared and evaluated in rat pharmacokinetic studies with the goal of improving the oral bioavailability of the parent (1). The prodrugs, in general, had improved aqueous solubility and oral bioavailability compared to 1. Prodrug 12, which contains an (acyloxy)alkoxy linker, showed the greatest improvement in the oral bioavailability relative to the parent (1), with a seven-fold increase (from 5% to 36%) in rat pharmacokinetic studies.

Keywords: CRF; Corticotropin-releasing factor; Prodrug; Pyrazinone.

MeSH terms

  • Animals
  • Biological Availability
  • Prodrugs / chemical synthesis*
  • Prodrugs / pharmacokinetics
  • Prodrugs / pharmacology*
  • Pyrazines / pharmacokinetics
  • Pyrazines / pharmacology*
  • Rats
  • Receptors, Corticotropin-Releasing Hormone / antagonists & inhibitors*

Substances

  • BMS 665053
  • Prodrugs
  • Pyrazines
  • Receptors, Corticotropin-Releasing Hormone
  • CRF receptor type 1