Synthesis and structure: activity relationships of potent 1-(2-substituted-aminoacetyl)-4-fluoro-2-cyanopyrrolidine dipeptidyl peptidase 4 inhibitors

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  • Fukushima Hiroshi
    Medicinal Chemistry Laboratories, Taisho Pharmaceutical Co., Ltd.
  • Hiratate Akira
    Medicinal Chemistry Laboratories, Taisho Pharmaceutical Co., Ltd.
  • Takahashi Masato
    Medicinal Chemistry Laboratories, Taisho Pharmaceutical Co., Ltd.
  • Saito-Hori Masako
    Molecular Function and Pharmacology Laboratories, Taisho Pharmaceutical Co., Ltd.
  • Munetomo Eiji
    Molecular Function and Pharmacology Laboratories, Taisho Pharmaceutical Co., Ltd.
  • Kitano Kiyokazu
    Molecular Function and Pharmacology Laboratories, Taisho Pharmaceutical Co., Ltd.
  • Saito Hidetaka
    Non-clinical Quality Assurance Section, Taisho Pharmaceutical Co., Ltd.
  • Takaoka Yuji
    Research Computer System, Taisho Pharmaceutical Co., Ltd.
  • Yamamoto Koji
    Molecular Function and Pharmacology Laboratories, Taisho Pharmaceutical Co., Ltd.

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タイトル別名
  • Synthesis and Structure-Activity Relationships of Potent 1-(2-Substituted-aminoacetyl)-4-fluoro-2-cyanopyrrolidine Dipeptidyl Peptidase IV Inhibitors

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Dipeptidyl peptidase IV (DPP-IV) inhibitors have attracted attention as potential drugs for use in the treatment of type 2 diabetes because they prevent the degradation of glucagon-like peptide-1 (GLP-1) and extend its duration of action. We previously reported that 2-cyano-4-fluoropyrrolidines act as potent DPP-IV inhibitors and have been modifying the 1-position of pyrrolidine to obtain more useful inhibitors. An L-tert-butylglycine derivative was found to be a stable and potent DPP-IV inhibitor that exhibits a glucose lowering effect in vivo. Here, we report the synthesis of and biological data on the aforementioned derivatives.

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