Discovery of Novel Indazole Derivatives as Orally Available β3-Adrenergic Receptor Agonists Lacking Off-Target-Based Cardiovascular Side Effects

J Med Chem. 2017 Apr 27;60(8):3252-3265. doi: 10.1021/acs.jmedchem.6b01197. Epub 2017 Apr 11.

Abstract

We previously discovered that indazole derivative 8 was a highly selective β3-adrenergic receptor (β3-AR) agonist, but it appeared to be metabolically unstable. To improve metabolic stability, further optimization of this scaffold was carried out. We focused on the sulfonamide moiety of this scaffold, which resulted in the discovery of compound 15 as a highly potent β3-AR agonist (EC50 = 18 nM) being inactive to β1-, β2-, and α1A-AR (β13, β23, and α1A3 > 556-fold). Compound 15 showed dose-dependent β3-AR-mediated responses in marmoset urinary bladder smooth muscle, had a desirable metabolic stability and pharmacokinetic profile (Cmax and AUC), and did not obviously affect heart rate or mean blood pressure when administered intravenously (3 mg/kg) to anesthetized rats. Thus, compound 15 is a highly potent, selective, and orally available β3-AR agonist, which may serve as a candidate drug for the treatment of overactive bladder without off-target-based cardiovascular side effects.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Oral
  • Adrenergic beta-3 Receptor Agonists / adverse effects
  • Adrenergic beta-3 Receptor Agonists / chemistry
  • Adrenergic beta-3 Receptor Agonists / pharmacology*
  • Animals
  • Cardiovascular System / drug effects*
  • Dogs
  • Drug Discovery
  • Humans
  • Indazoles / adverse effects
  • Indazoles / chemistry
  • Indazoles / pharmacology*
  • Rats

Substances

  • Adrenergic beta-3 Receptor Agonists
  • Indazoles