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Method for synthesizing and refining cinacalcet hydrochlorid

A technology of cinacalcet hydrochloride and refining method, which is applied in the field of synthesis and refining of cinacalcet hydrochloride bulk drug, can solve the problems of small reaction scale, insufficient purity of raw material drug, difficult purification, etc., and achieve short reaction steps and raw material The effect of convenient source and little environmental pollution

Active Publication Date: 2014-04-23
SINOPHARM A THINK PHARMA
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0011] In the existing synthetic technology, there are problems such as small reaction scale, insufficient purity of raw materials, and difficulty in purification to varying degrees.

Method used

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  • Method for synthesizing and refining cinacalcet hydrochlorid
  • Method for synthesizing and refining cinacalcet hydrochlorid
  • Method for synthesizing and refining cinacalcet hydrochlorid

Examples

Experimental program
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Embodiment Construction

[0042] The present invention will be further described below by specific embodiment.

[0043] The first step: the synthesis of 3-(trifluoromethyl) phenylpropionyl chloride:

[0044] Weigh 3 - Add 20.0 g of (trifluoromethyl)phenylpropionic acid to 100.0 ml of toluene, stir evenly, slowly add 40.0 ml of thionyl chloride to the reaction system, slowly raise the temperature to 80 °C and stir for 3 h, after the reaction, remove the residual under reduced pressure Thionyl chloride and solvent, get 3 - (Trifluoromethyl)phenylpropionyl chloride.

[0045] The second step: the synthesis of N-((1R)-1-(1-naphthyl)ethyl)-3-(3-(trifluoromethyl)phenyl)propanamide:

[0046] Weigh 15.70g R-1-(1-naphthyl)ethylamine and 13.91g triethylamine, dissolve in 150 ml dichloromethane, dissolve the acid chloride obtained in the previous step reaction in 50 ml dichloromethane, drop slowly into the reaction system, control the reaction temperature at 0 to 20°C, and complete the reaction in 30 min, ad...

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Abstract

The invention explores a method for synthesizing and refining cinacalcet hydrochlorid, especially avoids toxic and expensive reaction reagents reported in literatures; the invention has the advantages of convenient sources of raw materials and reagents, low cost, little pollution to environment and simple operation, the invention is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing and refining a novel cinacalcet hydrochloride crude drug, belonging to the technical field of medicinal chemistry. Background technique [0002] Cinacalcet Hydrochloride (Cinacalcet Hydrochlorid) is the first small-molecule drug listed by Amgen in the United States to regulate human hormone levels. Drug of benefit to patients with renal and parathyroid disease, mainly for the treatment of secondary hyperparathyroidism. Its molecular structure and absolute configuration are shown in formula 1: [0003] [0004] Formula 1 [0005] Cinacalcet is a drug launched in 2004, and there are many reports on its synthesis process. The synthetic route reported in the patent US No.6,211,244 is to use m-trifluoromethyl phenylpropionaldehyde and (R)-1-naphthylethylamine as raw materials, carry out condensation reaction (formula 2), and then use nitrile group hydroboration in methanol The target compound is obta...

Claims

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Application Information

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IPC IPC(8): C07C211/30C07C209/50C07C209/00C07C209/84
Inventor 不公告发明人
Owner SINOPHARM A THINK PHARMA
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