Discovery of N-(4-methoxy-7-methylbenzo[d]thiazol-2-yl)isonicatinamide, ML293, as a novel, selective and brain penetrant positive allosteric modulator of the muscarinic 4 (M4) receptor

Bioorg Med Chem Lett. 2012 Aug 1;22(15):5084-8. doi: 10.1016/j.bmcl.2012.05.109. Epub 2012 Jun 6.

Abstract

Herein we describe the discovery and development of a novel class of M(4) positive allosteric modulators, culminating in the discovery of ML293. ML293 exhibited modest potency at the human M4 receptor (EC(50)=1.3 μM) and excellent efficacy as noted by the 14.6-fold leftward shift of the agonist concentration-response curve. ML293 was also selective versus the other muscarinic subtypes and displayed excellent in vivo PK properties in rat with low IV clearance (11.6 mL/min/kg) and excellent brain exposure (PO PBL, 10 mg/kg at 1h, [Brain]=10.3 μM, B:P=0.85).

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Allosteric Regulation
  • Amides / chemistry
  • Animals
  • Brain / metabolism*
  • CHO Cells
  • Cricetinae
  • Cricetulus
  • Drug Evaluation, Preclinical
  • Humans
  • Niacinamide / analogs & derivatives*
  • Niacinamide / chemistry
  • Niacinamide / pharmacokinetics
  • Rats
  • Receptor, Muscarinic M4 / chemistry*
  • Receptor, Muscarinic M4 / metabolism
  • Structure-Activity Relationship

Substances

  • Amides
  • N-(4-methoxy-7-methylbenzo(d)thiazol-2-yl)isonicatinamide
  • Receptor, Muscarinic M4
  • Niacinamide