Novel selective inhibitors of neutral endopeptidase for the treatment of female sexual arousal disorder. Synthesis and activity of functionalized glutaramides

J Med Chem. 2006 Jul 13;49(14):4409-24. doi: 10.1021/jm060133g.

Abstract

Female sexual arousal disorder (FSAD) is a highly prevalent sexual disorder affecting up to 40% of women. We describe herein our efforts to identify a selective neutral endopeptidase (NEP) inhibitor as a potential treatment for FSAD. The rationale for this approach, together with a description of the medicinal chemistry strategy, lead compounds, and SAR investigations are detailed. In particular, the strategy of starting with the clinically precedented selective NEP inhibitor, Candoxatrilat, and targeting low molecular weight and relatively polar mono-carboxylic acids is described. This led ultimately to the prototype development candidate R-13, for which detailed pharmacology and pharmacokinetic parameters are presented.(1)

MeSH terms

  • Acids, Carbocyclic / chemical synthesis*
  • Acids, Carbocyclic / pharmacokinetics
  • Acids, Carbocyclic / pharmacology
  • Amides / chemical synthesis*
  • Amides / pharmacokinetics
  • Amides / pharmacology
  • Animals
  • CHO Cells
  • Clitoris / blood supply
  • Clitoris / drug effects
  • Cricetinae
  • Cricetulus
  • Dogs
  • Female
  • Humans
  • Male
  • Neprilysin / antagonists & inhibitors*
  • Pentanoic Acids / chemical synthesis*
  • Pentanoic Acids / pharmacokinetics
  • Pentanoic Acids / pharmacology
  • Pyridines / chemical synthesis
  • Pyridines / pharmacokinetics
  • Pyridines / pharmacology
  • Rabbits
  • Rats
  • Recombinant Proteins / antagonists & inhibitors
  • Regional Blood Flow / drug effects
  • Sexual Dysfunctions, Psychological / drug therapy*
  • Species Specificity
  • Stereoisomerism
  • Structure-Activity Relationship
  • Thiadiazoles / chemical synthesis*
  • Thiadiazoles / pharmacokinetics
  • Thiadiazoles / pharmacology
  • Vagina / blood supply
  • Vagina / drug effects

Substances

  • 2-(1-((2-ethyl-1,3,4-thiadiazol-5-yl)aminocarbonyl)cyclopentyl)pentanoic acid
  • Acids, Carbocyclic
  • Amides
  • Pentanoic Acids
  • Pyridines
  • Recombinant Proteins
  • Thiadiazoles
  • Neprilysin