The influence of conformational restriction in the C-terminus of growth hormone secretagogues on their potency

Eur J Med Chem. 2002 Jun;37(6):487-501. doi: 10.1016/s0223-5234(02)01370-3.

Abstract

In order to obtain more potent growth hormone secretagogues, a comparison of ipamorelin and NN703 suggested the addition of a polar group at the C-terminus of NN703. A study was conducted using constrained amines for this purpose. Here, substituted 4-piperidinylamino- and 4-dimethylaminopiperidino-substituents were found to give the most active compounds. A replacement of the 4-dimethylaminopiperidino-substituent with 4-hydroxypiperidino resulted in a series of compounds, which showed in vitro activity with EC(50) values in the low nanomolar range, and favourable kinetic properties, such as 40% oral bioavailability. The most promising compound was also tested in a swine in vivo model, resulting in a growth hormone level with a C(max) of over 40 ng mL(-1).

MeSH terms

  • Animals
  • Biological Availability
  • Cells, Cultured
  • Chromatography, High Pressure Liquid
  • Dipeptides / chemistry*
  • Dipeptides / pharmacology*
  • Dogs
  • Dose-Response Relationship, Drug
  • Half-Life
  • Hormones / chemistry*
  • Hormones / pharmacology*
  • Human Growth Hormone / metabolism*
  • Hydrogen Bonding
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Male
  • Methylation
  • Molecular Conformation
  • Oligopeptides / chemistry*
  • Oligopeptides / pharmacology*
  • Rats
  • Swine

Substances

  • Dipeptides
  • Hormones
  • Indicators and Reagents
  • Oligopeptides
  • Human Growth Hormone
  • tabimorelin
  • ipamorelin