Discovery and Lead Optimization of Atropisomer D1 Agonists with Reduced Desensitization

J Med Chem. 2018 Dec 27;61(24):11384-11397. doi: 10.1021/acs.jmedchem.8b01622. Epub 2018 Dec 11.

Abstract

The discovery of D1 subtype-selective agonists with drug-like properties has been an enduring challenge for the greater part of 40 years. All known D1-selective agonists are catecholamines that bring about receptor desensitization and undergo rapid metabolism, thus limiting their utility as a therapeutic for chronic illness such as schizophrenia and Parkinson's disease. Our high-throughput screening efforts on D1 yielded a single non-catecholamine hit PF-4211 (6) that was developed into a series of potent D1 receptor agonist leads with high oral bioavailability and CNS penetration. An important structural feature of this series is the locked biaryl ring system resulting in atropisomerism. Disclosed herein is a summary of our hit-to-lead efforts on this series of D1 activators culminating in the discovery of atropisomer 31 (PF-06256142), a potent and selective orthosteric agonist of the D1 receptor that has reduced receptor desensitization relative to dopamine and other catechol-containing agonists.

MeSH terms

  • Animals
  • Biological Availability
  • CHO Cells
  • Cricetulus
  • Cyclic AMP / metabolism
  • Dogs
  • Dopamine Agonists / adverse effects
  • Dopamine Agonists / chemistry*
  • Dopamine Agonists / pharmacology*
  • Dose-Response Relationship, Drug
  • HEK293 Cells
  • Half-Life
  • High-Throughput Screening Assays / methods
  • Humans
  • Madin Darby Canine Kidney Cells
  • Male
  • Mice, Inbred Strains
  • Neurons / drug effects
  • Neurons / metabolism
  • Rats
  • Receptors, Dopamine D1 / agonists*
  • Receptors, Dopamine D1 / metabolism
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Dopamine Agonists
  • Receptors, Dopamine D1
  • Cyclic AMP