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Method for preparing cinacalcet hydrochloride

A technology of cinacalcet hydrochloride and salt-forming reaction, applied in chemical instruments and methods, preparation of amino compounds, preparation of organic compounds, etc., can solve problems such as cumbersome operation, unfavorable industrial production and application, etc.

Active Publication Date: 2018-12-28
JIANGSU YONGAN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthesis strategy adds a one-step reaction, which leads to cumbersome operation and requires more manpower and material resources, which is not conducive to industrial production and application

Method used

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  • Method for preparing cinacalcet hydrochloride
  • Method for preparing cinacalcet hydrochloride
  • Method for preparing cinacalcet hydrochloride

Examples

Experimental program
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Embodiment 1

[0032] 1) Preparation of methylsulfonyl-3-(3-trifluoromethylphenyl)propyl ester

[0033] 10kg of dichloromethane was added to a 50L reactor, and 3-(3-trifluoromethylphenyl)propanol (1kg, 4.90mol) and triethylamine (0.59kg, 5.88mol) were added successively under stirring. Dichloromethane rinse tank mouth. Cool down to -5-10°C, slowly add methanesulfonyl chloride (0.62kg, 5.39mol) dropwise, keep the temperature of the reaction system at -5-10°C, and complete the dropwise addition in about 50-80min. Continue to incubate until the reaction is complete as monitored by TLC, and the reaction ends in about 1 hour.

[0034] Add 10kg of water while stirring, continue to stir for 20min, and let stand to separate layers. The organic phase was retained, and the aqueous phase was extracted and separated with 11 kg of dichloromethane, the organic phases were combined, and the aqueous phase was discarded.

[0035] Transfer the organic phase to a 50L reaction kettle, cool down to 5-10°C, ad...

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Abstract

The invention provides a method for preparing cinacalcet hydrochloride. The method comprises the following steps: with 3-(3-trifluoromethylphenyl)propanol shown as a formula I as a starting material,performing an acylation reaction on the starting material and methylsulfonyl chloride to obtain methylsulfonyl-3-(3-trifluoromethylphenyl) propyl ester shown as a formula II; in the presence of K2CO3,KI and ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate, performing a substitution reaction on the methylsulfonyl-3-(3-trifluoromethylphenyl) propyl ester shown as the formula II and (R)-1-(1-naphthyl)ethylamine shown as a formula III to obtain a system containing a compound shown as a formula IV; performing a salt forming reaction on the compound shown as the formula IV and hydrochloric acid to obtain a target product, namely the cinacalcet hydrochloride. Through the addition of the trace KI and the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate in the substitution reaction in the step 2), the substitution reaction is speeded up, the yield of the product is increased and the purity of the product is improved.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for preparing cinacalcet hydrochloride. Background technique [0002] Cinacalcet is the first drug in a new class of compounds known as calcimimetics, which activate calcium receptors in the parathyroid glands, thereby reducing parathyroid hormone (PTH) secretion. Cinacalcet hydrochloride is a calcimimetic agent developed by U.S. NPSP Pharmaceuticals. On March 8, 2004, FDA approved the production of cinacalcet hydrochloride produced by Amgen (the licensee of the product of NPS Pharmaceuticals). Sensipar; In October, 2007, cinacalcet hydrochloride produced by Kylin Pharmaceutical Co., Ltd. was listed in Japan under the trade name REGPARA, and the specifications were 25mg and 75mg (in terms of cinacalcet). [0003] Existing adopt nucleophilic substitution method to prepare the technology of cinacalcet hydrochloride, take 3-[3-(trifluoromethyl)-phenyl] propanol as raw materia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/16C07C211/30C07C209/00
Inventor 罗桓康彦龙利虔邱春芳刘克磊王帅威
Owner JIANGSU YONGAN PHARMA CO LTD