发明公开
EP0514090A1 Procedure for the inversion of the stereochemistry at C13 of avermectin aglycone compounds 失效
Verfahren zur Inversion der Konfiguration a C-13 von Avermectinaglyconderivaten。

  • 专利标题: Procedure for the inversion of the stereochemistry at C13 of avermectin aglycone compounds
  • 专利标题(中): Verfahren zur Inversion der Konfiguration a C-13 von Avermectinaglyconderivaten。
  • 申请号: EP92304151.1
    申请日: 1992-05-08
  • 公开(公告)号: EP0514090A1
    公开(公告)日: 1992-11-19
  • 发明人: Jones, Todd K.Mrozik, Helmut
  • 申请人: MERCK & CO. INC.
  • 申请人地址: 126, East Lincoln Avenue P.O. Box 2000 Rahway New Jersey 07065-0900 US
  • 专利权人: MERCK & CO. INC.
  • 当前专利权人: MERCK & CO. INC.
  • 当前专利权人地址: 126, East Lincoln Avenue P.O. Box 2000 Rahway New Jersey 07065-0900 US
  • 代理机构: Thompson, John Dr.
  • 优先权: US698874 19910513
  • 主分类号: C07H19/01
  • IPC分类号: C07H19/01 C07D493/22 A01N43/90 A61K31/70
Procedure for the inversion of the stereochemistry at C13 of avermectin aglycone compounds
摘要:
The natural stereochemistry at the 13-position of avermectin aglycones, normally α-oriented or below the plane of the molecule, is inverted or epimerized into the β-position. The procedure starts with the avermectin aglycone compounds where the 13α-hydroxy group is substituted with a leaving group. Treatment of the substituted compound with tetra alkyl ammonium nitrate displaces the leaving group, substitutes a nitrate ester or a nitrooxy group, for the hydroxy and inverts the 13-stereochemistry to β. Reduction of the nitrooxy group returns the 13-hydroxy group and retains the 13-β configuration. The intermediate 13-nitrooxy compounds are themselves potent anti-parasitic agents.
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