Novel orally active morpholine N-arylsulfonamides gamma-secretase inhibitors with low CYP 3A4 liability

Bioorg Med Chem Lett. 2009 Nov 1;19(21):6032-7. doi: 10.1016/j.bmcl.2009.09.055. Epub 2009 Sep 19.

Abstract

A new class of 2,6-disubstituted morpholine N-arylsulfonamide gamma-secretase inhibitors was designed based on the introduction of a morpholine core in lieu or piperidine in our lead series. This resulted in compounds with improved CYP 3A4 profiles. Several analogs that were active at lowering Abeta levels in Tg CRND8 mice upon oral administration were identified.

MeSH terms

  • Administration, Oral
  • Amyloid Precursor Protein Secretases / antagonists & inhibitors*
  • Amyloid Precursor Protein Secretases / metabolism
  • Animals
  • Cytochrome P-450 CYP3A / metabolism
  • Cytochrome P-450 CYP3A Inhibitors*
  • Disease Models, Animal
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacokinetics
  • Humans
  • Mice
  • Mice, Transgenic
  • Morpholines / chemical synthesis
  • Morpholines / chemistry*
  • Morpholines / pharmacokinetics
  • Rats
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacokinetics

Substances

  • Cytochrome P-450 CYP3A Inhibitors
  • Enzyme Inhibitors
  • Morpholines
  • Sulfonamides
  • morpholine
  • Cytochrome P-450 CYP3A
  • CYP3A4 protein, human
  • Amyloid Precursor Protein Secretases