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Method for important midbody of strontium ranelate

A technology of ethyl thiophenecarboxylate and compounds, which is applied in the field of key intermediates for the preparation of anti-osteoporosis drug strontium ranelate, can solve the problems that the compound of formula I is not mentioned, and achieve the improvement of purity, the solution of crystallization problems, and the ease of reaction controllable effect

Inactive Publication Date: 2008-09-24
BEIJING D VENTUREPHARM TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In existing published report, do not mention above-mentioned reaction condition preparation formula I compound

Method used

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  • Method for important midbody of strontium ranelate
  • Method for important midbody of strontium ranelate
  • Method for important midbody of strontium ranelate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 10g 5-amino-4-cyano-3-(2-ethoxyl-2-oxoethyl)-2-thiophenecarboxylic acid ethyl ester, 14.7g anhydrous potassium carbonate and 120ml butanone in 250ml there-necked flask , stir to dissolve. Heat to reflux for 20 minutes. Under reflux conditions, 41.4 g of ethyl bromoacetate was added dropwise. After dropping, the reaction was detected by TLC. After the reaction was completed, suction filtration was performed, and the filtrate was concentrated under reduced pressure to obtain 40.7 g of dark brown oil. Freeze, suction filter, dry to constant weight, obtain 13.7g light brown solid powder, namely 5-[bis(2-ethoxyl-2-oxoethyl)amino]-4-cyano-3-(2 -Ethoxy-2-oxoethyl)-2-thiophenecarboxylic acid ethyl ester, the yield is 90%. HPLC purity 97%.

Embodiment 2

[0026] Add 10g 5-amino-4-cyano-3-(2-methoxy-2-oxoethyl)-2-thiophenecarboxylic acid ethyl ester, 13.5g anhydrous sodium carbonate and 120ml acetone in 250ml there-necked flask, Stir to dissolve. Heat to reflux for 20 minutes. Under reflux conditions, 41.4 g of ethyl bromoacetate was added dropwise. After dropping, the reaction was detected by TLC. After the reaction was completed, suction filtration was performed, and the filtrate was concentrated under reduced pressure to obtain 40.7 g of dark brown oil. Freeze, filter with suction, and dry to constant weight to obtain 5-[bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-3-(2-ethoxy-2-oxo Ethyl)-2-thiophenecarboxylic acid ethyl ester, the yield is 65%. HPLC purity 93%.

Embodiment 3

[0028] Add 10g 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)-2-thiophenecarboxylic acid ethyl ester, 14.7g anhydrous potassium carbonate and 90ml N in the 250ml there-necked flask, N-dimethylformamide, stirred to dissolve. After heating to 60-70°C, 41.4 g of ethyl bromoacetate was added dropwise. After dropping, the reaction was detected by TLC. After the reaction was completed, suction filtration was performed, and the filtrate was concentrated under reduced pressure to obtain 40.7 g of dark brown oil. Freeze, filter with suction, and dry to constant weight to obtain 5-[bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-3-(2-ethoxy-2-oxo Ethyl)-2-thiophenecarboxylic acid ethyl ester, the yield was 73%. HPLC purity 92.5%.

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Abstract

The present invention relates to a new method for preparing 5-[bi-(2-oxethyl-2-ketoethyl) amino]-4- cyano-3-(2-oxethyl-2-ketoethyl)-2-thiophene ethyl formate with a reactant produced by a compound expressed in the formula (III) and a compound expressed in the formula (IV) under a certain condition, and the compound is an important intermediate for the preparation of strontium ranelate.

Description

technical field [0001] The present invention relates to the preparation of 5-[bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-3-(2-ethoxy-2-oxoethyl)-2-thiophene A method for ethyl formate, the compound is a key intermediate for preparing the anti-osteoporosis drug strontium ranelate. Background technique [0002] The present invention relates to a new method for the preparation of compounds of formula I: [0003] [0004] According to the method of the present invention, the compound of formula I obtained can be used to synthesize the compound of formula II strontium ranelate salt and the hydrate of the strontium salt: [0005] [0006] Strontium ranelate has good pharmacological and therapeutic properties, especially significant anti-osteoporosis properties, so that the compound can be used for treating bone diseases. Its preparation and therapeutic use have been disclosed in European patent specification EP0412850. [0007] The catalysts involved in the preparation of comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/40
Inventor 薛绪飞
Owner BEIJING D VENTUREPHARM TECH DEV
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