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。
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申请号: EP92304151.1申请日: 1992-05-08
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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
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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