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Method for preparing tandospirone and analogues of tandospirone

A technology for tandospirone and analogs, which is applied in the field of preparation of tandospirone citrate, can solve the problems of poor product quality, difficulty in purifying intermediates, and difficulty in meeting medicinal requirements, and achieves low cost and good quality. , the effect of mild reaction conditions

Inactive Publication Date: 2010-11-10
PKU HEALTHCARE CORP LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The third is that the purification of intermediates is difficult, and the quality of the obtained products is poor, and it is difficult to meet the requirements of medicine

Method used

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  • Method for preparing tandospirone and analogues of tandospirone
  • Method for preparing tandospirone and analogues of tandospirone
  • Method for preparing tandospirone and analogues of tandospirone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Preparation of exo-cis-bicyclo[2,2,1]heptane-5-ene-2,3-dicarboxylic anhydride In a reaction flask, add 300 grams of NA anhydride, 2100 ml of ethyl acetate, and heat to Reflux, under the irradiation of sodium lamp 500W, react for 2 hours, evaporate the solvent, and refine exo-cis-bicyclo[2,2,1]heptane-5-ene-2,3-dicarboxylic acid anhydride 274.2 grams, received Rate 91.4%, mp 141.0-142.5°C.

Embodiment 2

[0023] Example 2: N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-exo-cis-bicyclo[2,2,1]heptane-5-ene-2, Preparation of 3-dicarboximide (abbreviated as condensate, the same below)

[0024] In the reaction flask, 200 grams of exo-cis-bicyclo[2,2,1]heptane-5-ene-2,3-dicarboxylic anhydride, 1-(4-aminobutyl)-4-(2 -320 grams of pyrimidinyl) piperazine, 1600 ml of toluene, 320 grams of sodium methoxide, reacted at 110 ° C for 10 hours, evaporated the solvent, and purified 425.8 grams with ethyl acetate, yield 91.6%, mp 110.5~111.8 ° C, HPLC 98.7 %.

Embodiment 3

[0025] Embodiment 3: the preparation of condensate

[0026] In the reaction flask, add 80 grams of exo-cis-bicyclo[2,2,1]heptane-5-ene-2,3-dicarboxylic anhydride, 1-(4-aminobutyl)-4-(2- Pyrimidinyl)piperazine 160g, DMF700ml, sodium carbonate 120g, reacted at 140°C for 7 hours, evaporated the solvent, and purified with ethyl acetate to obtain 176.8g, yield 95.1%, mp 110.0~112.0°C, HPLC 99.1% .

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Abstract

The invention discloses tandospirone and analogues of the tandospirone. In the method, NA anhydride generates translocation under an illumination condition, the product of the translocation and 1-(4-amniobutyl)-4-(2-pyrimidyl) piperazine are condensed, the product of the condensation is reduced to form tandospirone in the presence of Pd / C, and the tandospirone is reacted with an acid to form a salt of the tandospirone. The method has the advantages that: the reaction conditions are mild; special requirements on equipment are avoided; the yield is high; the used solvent can be recycled; the tandospirone and the analogues of tandospirone are of high quality; the single maximum impurity is less than 0.1 percent; and the prepared preparation has good medicament effect; the operation is simple; the purity is high; the cost is low; and large-scale product can be realized.

Description

technical field [0001] The present invention relates to a kind of preparation method of tandospirone and analogue thereof, relate in particular to a kind of preparation method of tandospirone citrate. Background technique [0002] Anxiety is the most common emotional reaction and a central symptom of all neuroses. With the development of society and the accelerated pace of life, people's demand for anti-anxiety drugs is increasing day by day. The first-generation anxiolytic drug meprobamate (meprobamate), due to its poor drug resistance and severe withdrawal symptoms, was replaced by the second-generation anti-anxiety drug benzodiazepines (BDZ). Commonly used anti-anxiety drugs [1]. But BDZ also has serious disadvantages. It may cause psychomotor dysfunction, memory discrimination dysfunction, psychological and physical dependence and other problems. In order to overcome the shortcomings of BDZ, the third generation of anti-anxiety drugs has been launched, which mainly ac...

Claims

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Application Information

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IPC IPC(8): C07D403/12
Inventor 张金生李翎
Owner PKU HEALTHCARE CORP LTD
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