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Method for preparing pioglitazone

A pyridyl, thiazolidinedione technology, applied in the fields of organic chemistry and medicinal chemistry, can solve the problems of difficult reduction, difficult removal, low product yield, etc. Effect

Inactive Publication Date: 2006-10-25
北京太洋药业股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Compound II is catalyzed by Pd-black and under high pressure (30-100kg / cm 2 ) is reduced with hydrogen to obtain compound I, and the high-pressure catalytic hydrogenation will be limited by the container, and the more important thing is that the reduction is difficult to complete, so that the compound II containing a large amount (>>3% w / w) appears in the form of impurities in the product, while It is difficult to remove in the refining of the product, and the product yield is low

Method used

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  • Method for preparing pioglitazone
  • Method for preparing pioglitazone
  • Method for preparing pioglitazone

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Experimental program
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Effect test

Embodiment 1

[0019] Embodiment 1: the method for preparing compound I

[0020] Step 1: Catalyst Preparation

[0021] Dissolve dimethylglyoxime and cobaltous chloride hexahydrate in DMF according to the ratio of dimethylglyoxime (g): cobalt chloride hexahydrate (g): DMF (ml) = 19.33: 1: 410, and stir evenly.

[0022] Step 2: Preparation of reducing agent

[0023] Add 5.26g of sodium borohydride to the 0.15N sodium hydroxide solution, dissolve completely under stirring, and set aside.

[0024] Step 3: React

[0025] Put 347ml of water, 83ml of THF, 27ml of 1N sodium hydroxide solution and 24.68g of compound II into a 1000ml three-neck flask, cool down to 15°C with ice water while stirring, add 7ml of the prepared catalyst, and slowly drop the prepared reducing agent solution , a large number of bubbles are generated during the reaction, control the reaction temperature at 15°C, and adjust the addition rate, the drop is completed in about 0.5 hours, and the reaction is kept for 3 hours; sl...

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Abstract

This invention provides method of prepare formula (I) 5-[4-[2-(5-ethyl-2-pyridyl) ethoxy] phenyl group]-2, 4-thiazolidine diketone or its pharmaceutical salt. The method is that formula (II) compound of the diketone above is made under function of sodium borohydride reducer and catalyst in alkali condition, the mixed catalyst is dimethylglyoxime, hexahydrate cobaltous chloride and dimethyl formamide. The yield is high, quality is good, impurity content is low, and it is propitious to industrial manufacture.

Description

technical field [0001] The present invention relates to the field of organic chemistry and medicinal chemistry, specifically, the present invention relates to pioglitazone namely 5-[4-[2-(5-ethyl-2 pyridyl)ethoxy]benzylidene]-2,4 - Process for the preparation of thiazolidinediones. Background technique [0002] Pioglitazone (INN: Pioglitazone) is a new generation of thiazolidinedione insulin sensitizers, which has a good effect on type II diabetes, and its chemical structure is shown in I. According to literature reports, its preparation method mostly adopts intermediate 5-[4-[2-(5-ethyl-2 pyridyl)ethoxy]benzylidene]-2,4-thiazolidinedione (compound II) reduction and make, but all there is very big defect, especially be difficult to obtain realizing aspect quality control and industrialized production. Such as: Document 1: Yu.mouse et al., Chem.Phar.Bull, 39 (6) 1440-1445 (1991), which discloses a preparation method of compound I; Document 2: J.Med.Chem.1994, 37, 3977-3985...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12
Inventor 罗宣德王慧文秦红
Owner 北京太洋药业股份有限公司