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Method for synthesizing calcimimetic cinacalcet hydrochloride

A technology for the synthesis of cinacalcet hydrochloride and calcimimetic agent, which is applied in the field of synthesizing calcimimetic agent cinacalcet hydrochloride, can solve the problems of secondary substitution by-products with many unknown impurities and low reaction yield, and achieve cheap raw materials and easy operation Simple, high-yield results

Inactive Publication Date: 2017-03-29
SHANGHAI QINGSONG PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0021] Patent document WO2006125026 discloses that the starting material 3-(3-trifluoromethylphenyl)propanol is protected with methanesulfonyl chloride for hydroxyl, and then with (R)-1-(1-naphthyl)ethylamine. Nuclear reaction, in which a large number of disubstituted by-products and more unknown impurities are produced, post-treatment requires multiple purifications, and the reaction yield is low

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  • Method for synthesizing calcimimetic cinacalcet hydrochloride
  • Method for synthesizing calcimimetic cinacalcet hydrochloride
  • Method for synthesizing calcimimetic cinacalcet hydrochloride

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Embodiment Construction

[0037] The following description serves to disclose the present invention to enable those skilled in the art to carry out the present invention. The preferred embodiments described below are only examples, and those skilled in the art can devise other obvious variations.

[0038] The method is a new synthetic route: use trityl chloride to protect the amino protection of (R)-1-(1-naphthyl)ethylamine, and then carry out the scheme of nucleophilic substitution reaction. The specific synthetic route is as follows :

[0039]

[0040] Step 1: Preparation of methylsulfonyl-3-(3-trifluoromethylphenyl)propyl ester B

[0041] At room temperature, add 15ml CH to a 100ml reaction vial 2 Cl 2 , 3g 3-(3-trifluoromethylphenyl) propanol A, 2.2g triethylamine, stir and dissolve, add 2g methanesulfonyl chloride dropwise, after the dropwise addition, keep the temperature for 2-3 hours, and add to the reaction kettle Add 9ml of 1mol / l dilute hydrochloric acid, stir and separate the liquids...

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Abstract

The invention provides a method for synthesizing calcimimetic cinacalcet hydrochloride; the method comprises the steps of preparing methylsulfonyl-3-(3-trifluoromethylphenyl)propionate; preparing (R)-(+)-1-(1-naphthyl)ethyltribenzyllamine; preparing N-((1R)-1-(1-napthyl)ethyl)-3-(3-(trifluoromethyl)phenyl)propyl-1-tribenzylamine; preparing N-((1R)-1-(1-napthyl)ethyl)-3-(3-(trifluoromethyl)phenyl)propylamine hydrochloride. The synthetic route of the method has the advantages of low price and easy access of materials, good operational simplicity, high yield and the like.

Description

technical field [0001] The invention relates to a method for synthesizing a calcimimetic agent 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. It modulates the behavior of the parathyroid calcium receptor, reducing the levels of parathyroid hormone, calcium, phosphorus, and calcium-phosphate complexes by increasing the sensitivity of the receptor to calcium levels in the bloodstream. Mainly applicable to (1) treatment of secondary hyperparathyroidism in patients with chronic kidney disease (CKD) undergoing dialysis; (2) treatment of hypercalcemia in patients with parathyroid cancer; (3) severe hypercalcemia patients Primary HPT for those unable to undergo parathyroidectomy. [0003] Cinacalcet hydrochloride is a calcimimetic agent developed by U.S. NPS Pharmaceuticals. On M...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/00C07C211/30
CPCC07C209/00C07B2200/07C07C209/08C07C211/30C07C303/28
Inventor 张健陈晓娜张树斌高军峰谭宙宏
Owner SHANGHAI QINGSONG PHARMA
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