发明申请
US20120226044A1 Process for the preparation of 4-azasteroids 审中-公开
制备4-azasteroids的方法

  • 专利标题: Process for the preparation of 4-azasteroids
  • 专利标题(中): 制备4-azasteroids的方法
  • 申请号: US11630562
    申请日: 2005-07-04
  • 公开(公告)号: US20120226044A1
    公开(公告)日: 2012-09-06
  • 发明人: Yves BessardDavid L. Kuo
  • 申请人: Yves BessardDavid L. Kuo
  • 优先权: EP04015746.3 20040705
  • 国际申请: PCT/EP2005/007190 WO 20050704
  • 主分类号: C07D221/18
  • IPC分类号: C07D221/18
Process for the preparation of 4-azasteroids
摘要:
A process for the preparation of 4-steroids of the formula: R1 and R2 are independently selected from the group that is hydrogen, F, Cl, Br, I, C1-6-allyl and C1-6-alkoxy, and R4 is selected from the group that is hydrogen, (N,N-di-C1-6-allylamino)methyl, allylamino)ethyl, C1-6-alkyl, C1-6-alkoxy, phenyl and benzyl, and Q7 represents a carbonyl oxygen atom or is R7-1 and R7-2, wherein one of R7-1 and R7-2 is hydrogen and the other is selected from the group that is hydrogen, F, Cl, Br, I, C1-6-alkyl and C1-6-alkoxy, and R9 represents hydrogen or F, and Q11 represents a carbonyl oxygen atom or is R11-1 and R11-2, wherein one of R11-1 and R11-2 is hydrogen and the other is selected from the group that is hydrogen, cyano, cyano-C1-3-alkyl, acetoxy, COOH and COO−M+, wherein M+ is Na+, K+ or NH+4, and R16 is selected from the group that is hydrogen, cyano, cyano-C1-3-alkyl, acetoxy, COOH and COO−M+, wherein M+ is Na+, K+ or NH+4, and COOR represents COOH or COO−M+, wherein M+ is Na+, K+ or NH+4. The three step process includes (i) a haloform reaction of a 17-acetyl steroid converting the acetyl group into a —COOR group, (ii) subsequent ozonolysis of the A-ring and (iii) reclosure of the A-ring by reaction with an appropriate nitrogen compound of formula H2NR4 to afford a compound of formula I above.
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