Discovery of 1,5-benzodiazepines with peripheral cholecystokinin (CCK-A) receptor agonist activity (II): Optimization of the C3 amino substituent

J Med Chem. 1996 Dec 20;39(26):5236-45. doi: 10.1021/jm9601664.

Abstract

Analogs of the previously reported 1,5-benzodiazepine peripheral cholecystokinin (CCK-A) receptor agonist 1 were prepared which explore substitution and/or replacement of the C-3 phenyl urea moiety. Agonist efficacy on the isolated guinea pig gallbladder (GPGB) was retained with a variety of substituted ureas and amide analogs. Three compounds were identified which were orally active in the mouse gallbladder emptying assay (MGBE). The 2-indolamide (52) and N-(carboxymethyl)-2-indolamide (54) derivatives had improved affinity for the human CCK-A receptor but reduced agonist efficacy on the GPGB. Neither indolamide was orally active in a rat feeding assay. In contrast, the (3-carboxyphenyl)urea derivative (29, GW7854) had moderately increased affinity for the human CCK-B receptor but was a potent full agonist on the GPGB and was orally active in both the MGBE and rat feeding assays. GW7854 was a full agonist (EC50 = 60 nM) for calcium mobilization on CHO K1 cells expressing hCCK-A receptors and a potent antagonist of CCK-8 (pA2 = 9.1) on CHO K1 cells expressing hCCK-B receptors. GW7854 is a potent mixed CCK-A agonist/CCK-B antagonist which is orally active in two in vivo models of CCK-A-mediated agonist activity.

MeSH terms

  • Animals
  • Appetite Depressants / chemistry
  • Appetite Depressants / pharmacology*
  • Benzodiazepines / chemistry
  • Benzodiazepines / pharmacology*
  • CHO Cells
  • Calcium / metabolism
  • Cricetinae
  • Feeding Behavior / drug effects
  • Guinea Pigs
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mice
  • Rats
  • Receptor, Cholecystokinin A
  • Receptors, Cholecystokinin / agonists*
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Appetite Depressants
  • Receptor, Cholecystokinin A
  • Receptors, Cholecystokinin
  • Benzodiazepines
  • Calcium