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(2R)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a] pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine: A potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes

Journal of Medicinal Chemistry, ISSN: 0022-2623, Vol: 48, Issue: 1, Page: 141-151
2005
  • 821
    Citations
  • 0
    Usage
  • 271
    Captures
  • 0
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    821
    • Citation Indexes
      810
    • Patent Family Citations
      10
      • Patent Families
        10
    • Policy Citations
      1
      • Policy Citation
        1
  • Captures
    271

Article Description

A novel series of β-amino amides incorporating fused heterocycles, i.e., triazolopiperazines, were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-IV) for the treatment of type 2 diabetes. (2R)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H) -yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (1) is a potent, orally active DPP-IV inhibitor (IC = 18 nM) with excellent selectivity over other proline-selective peptidases, oral bioavailability in preclinical species, and in vivo efficacy in animal models. MK-0431, the phosphate salt of compound 1, was selected for development as a potential new treatment for type 2 diabetes.

Bibliographic Details

Kim, Dooseop; Wang, Liping; Beconi, Maria; Eiermann, George J; Fisher, Michael H; He, Huaibing; Hickey, Gerard J; Kowalchick, Jennifer E; Leiting, Barbara; Lyons, Kathryn; Marsilio, Frank; McCann, Margaret E; Patel, Reshma A; Petrov, Aleksandr; Scapin, Giovanna; Patel, Sangita B; Roy, Ranabir Sinha; Wu, Joseph K; Wyvratt, Matthew J; Zhang, Bei B; Zhu, Lan; Thornberry, Nancy A; Weber, Ann E

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Pharmacology, Toxicology and Pharmaceutics

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