Method for synthesizing 3,9-diaza spiro[5.5] undecane template compounds

A technique for the synthesis of diazaspiro compounds, which is applied in the field of preparation of spiro compounds, can solve the problems of harsh reaction conditions and low yields, and achieve the effects of short reaction routes, good biological activity, and favorable scale production
CN101255159AInactive Publication Date: 2008-09-03上海药明康德新药开发有限公司
4 Cites 5 Cited by

Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
上海药明康德新药开发有限公司
Publication Date
2008-09-03
Estimated Expiration
Not applicable · inactive patent

Smart Images

  • Figure 1
    Figure 1
  • Figure 2
    Figure 2
  • Figure 3
    Figure 3
Patent Text Reader

Abstract

The invention relates to a process for preparing spiro compounds, more particularly, relates to a synthetic process for 3, 9-diazaspiro [5. 5] undecane template compounds. The invention is mainly to solve the technical problems that the existing synthetic method for 3, 9-diazaspiro [5. 5] undecane spiro compounds has low yield and harsh reaction conditions. The process comprises using N-benzyl piperidine-4-ketone and ethyl cyanoacetate as starting material, generating dicyanocarbodiimide B in colamine solution, hydrolyzing selective decarboxylation in acid environment to obtain carbodiimide C, reducing the carbodiimide C by Lithium aluminum hydride to obtain diamine D, combining the different protecting groups to obtain the target template compounds. The invention provides a highly effective synthetic process with mild conditions and large scale preparing value for 3, 9-diazaspiro [5. 5] undecane template compounds.
Need to check novelty before this filing date? Find Prior Art

Description

Technical field:

[0001] The invention relates to a preparation method of a spiro compound, in particular to a synthesis method of a 3,9-diazaspiro[5.5]undecane template compound. Background technique:

[0002] Containing 3, the spiro compound of 9-diaza spiro [5.5] undecane structure has been proved to have better physiological activity, literature (Bioorganic & Medicinal Chemistry Letters 11 (2001) 1289-1292; US5451578; US6291460) once reported to 3,9-diazaspiro[5.5]undecane as the core of structure 1 compounds can be used as non-peptide glycoprotein antagonists to prevent thrombosis; it has been reported in document WO2005040167 that such compounds can be used to treat CCR8 receptor-related diseases, such as asthma.

[0003]

[0004] Regarding the synthesis method of 3,9-diazaspiro[5.5]undecane spiro compound, the literature reports can be found in US6291469. The method takes N-benzylpiperidin-4-one and ethyl cyanoacetate as starting materials, as shown in the followi...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More