发明名称 |
NEW METHODS FOR THE SYNTHESES OF ALFENTANIL, SUFENTANIL AND REMIFENTANIL |
摘要 |
Synthetic pathways are disclosed for synthesizing derivatives or analogs of fentanyl. Specifically set out are pathways for synthesizing alfentanil, sufentanil and remifentanil. The disclosed methods require fewer steps and produce a greater yield of product than methods reported in the prior art. The pathways to all these compounds begin with a common pathway of condensing a piperidone with a primary amine so as to form a 4-amino-4-carboxyamino-piperidine, wherein N of said piperidone is a -N-COO-(CH2)nCH3, alkylating an N of said primary amine which was condensed with said piperidone thereby producing an N-alkyl-anilide, and hydrolyzing said -COO-(CH2)nCH3 group of said 4-amino-4-carboxyamino-piperidine following the condensation reaction so as to form a piperidine hydrolysis product. This product can then be converted to remifentanil in a 4 step reaction. Also, this hydrolysis product can be treated with a hydride to yield a 4-hydroxymthyl-piperidine which can be converted to alfentanil in 3 further steps, to sufentanil in 3 more steps, or to a variety of remifentanil analogs in two steps.
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申请公布号 |
WO0140184(A2) |
申请公布日期 |
2001.06.07 |
申请号 |
WO2000US32882 |
申请日期 |
2000.12.04 |
申请人 |
MALLINCKRODT INC.;JACOB, MATHEW;KILLGORE, J., KENDALL |
发明人 |
JACOB, MATHEW;KILLGORE, J., KENDALL |
分类号 |
C07D211/58;C07D211/66;C07D401/06;C07D409/06;(IPC1-7):C07D211/66 |
主分类号 |
C07D211/58 |
代理机构 |
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主权项 |
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地址 |
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