Novel synthetic method for tadalafil

A technology of tadalafil and its synthesis method, which is applied in the direction of organic chemistry, can solve the problems of flammability, high toxicity, environmental pollution, etc., and achieve the effect of simple reaction method, convenient operation, and serious environmental pollution
CN105348283AActive Publication Date: 2016-02-24ZHEJIANG YONGNING PHARMA
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
ZHEJIANG YONGNING PHARMA
Publication Date
2016-02-24

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Abstract

The invention relates to a synthetic method for a compound in the technical field of medicine and chemical engineering, and particularly relates to a novel synthetic method for tadalafil. The synthetic method comprises the steps of: 1) condensing an initial raw material which is D-tryptophan (I) and methylamino acetonitrile (II) or salt thereof to obtain a compound as shown in a formula III; 2) carrying out Pictet-Spengler cyclization reaction on the compound as shown in the formula III and heliotropin and carrying out crystallization to obtain a compound as shown in a formula V; and 3) hydrolyzing the compound V under an acidic or alkaline condition by cyano and then condensing the compound to obtain the target product tadalafil (VI). The formula is shown in the description. In the synthetic method provided by the invention, chemical raw materials which are great in toxicity, severe in environmental pollution and flammable and combustible such as thionyl chloride, chloroacetyl chloride, methylamine and the like. The novel synthetic method for tadalafil provided by the invention is simple in reaction method, convenient to operate and high in yield.
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Description

technical field

[0001] The invention relates to a synthesis method of compounds in the technical field of medicine and chemical engineering, in particular to a synthesis method of tadalafil. Background technique

[0002] The chemical name of tadalafil is (6R-12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a - Hexahydropyrazino[1',2'-1,6]-pyrido[3,4-b]indole-1,4-dione, the structural formula is as follows:

[0003]

[0004] Tadalafil is a phosphodiesterase type V (PDE5) inhibitor. When sexual stimulation leads to the local release of nitric oxide, PDE5 is inhibited by tadalafil, which increases the level of cyclic guanosine monophosphate in the cavernous body of the penis, which leads to Smooth muscles relax and blood flows into the penile tissue, producing an erection. The compound was originally developed by GlaxoSmithKline and subsequently transferred to ICOS, and later jointly developed by ICOS and Eli Lilly. Approved by the FDA in 2003, tadalafil was listed in...

Claims

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