Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Environment-friendly synthesis method for cinacalcet

A technology of green synthesis and compound, which is applied in the field of green synthesis of Cinacase to achieve the effect of reducing pollution, high yield and low cost

Inactive Publication Date: 2011-01-12
SHANGHAI INSTITUTE OF TECHNOLOGY
View PDF6 Cites 12 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] Combining the above several methods, it can be found that the method for synthesizing compound 10 and R(+)-1-naphthylethylamine as raw materials is relatively simple, but the existing process There is still room for improvement

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Environment-friendly synthesis method for cinacalcet
  • Environment-friendly synthesis method for cinacalcet
  • Environment-friendly synthesis method for cinacalcet

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Add 0.6g R-(+)-1-naphthylethylamine, 0.86g [3-(3'-trifluoromethyl)phenyl]-1-chloropropane, 0.28g sodium hydroxide 8ml of aqueous solution and 0.06g of tetrabutylammonium bromide, stirred, and reacted at 70-75°C for 4h. Cool and extract with dichloromethane. The extract was washed with dilute hydrochloric acid, saturated sodium bicarbonate and saturated brine in sequence, dried over anhydrous sodium sulfate, filtered, and the solvent was removed to obtain cinacalcet. Pale yellow liquid, the yield is 82.1%, [α] D =-8.6 o (C=1, methanol).

Embodiment 2

[0044] Add 0.6g R-(+)-1-naphthylethylamine, 0.86g [3-(3'-trifluoromethyl)phenyl]-1-chloropropane, 0.40g potassium hydroxide 8ml of aqueous solution and 0.09g of tetrabutylammonium iodide, stirred, and reacted at 70-75°C for 4h. Cool and extract with dichloromethane. The extract was washed with dilute hydrochloric acid, saturated sodium bicarbonate and saturated brine in sequence, dried over anhydrous sodium sulfate, filtered, and the solvent was removed to obtain cinacalcet. Pale yellow liquid, yield 83.0%, [α] D =-9.2 o (C=1, methanol).

Embodiment 3

[0046] Add 0.6g R-(+)-1-naphthylethylamine, 0.93g [3-(3'-trifluoromethyl)phenyl]-1-chloropropane, and 1.1g of sodium carbonate in a 50ml three-necked flask successively. 10ml of aqueous solution and 0.09g of PEG6000 were stirred and reacted at 95-100°C for 24h. Cool and extract with dichloromethane. The extract was washed with dilute hydrochloric acid, saturated sodium bicarbonate and saturated brine in sequence, dried over anhydrous sodium sulfate, filtered, and the solvent was removed to obtain cinacalcet. Pale yellow liquid, the yield is 78.5%, [α] D =-8.8 o (C=1, methanol).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses an environment-friendly synthesis method for cinacalcet. The cinacalcet is prepared by reacting R(+)-1-naphthyl ethamine and [3-(3'-trifluoromethyl)phenyl]-1-halopropane or [3-(3'-trifluoromethyl)phenyl]-1-propylsulfonate serving as raw materials with water serving as medium under the action of a phase-transfer catalyst. The process has the advantages of reducing the cost, along with high yield, no any organic solvent during the reaction, and low environmental pollution, and thus is a synthesis method suitable for industrialization.

Description

technical field [0001] The invention relates to a green synthesis method of cinacalcet, a chiral drug for treating secondary hyperparathyroidism. technical background [0002] Cinacalcet, chemical name (R)-α-methyl-N-[3-[3'-(trifluoromethyl)phenyl]propyl]-1-naphthylmethylamine, molecular formula is C 22 h 22 f 3 N, CA number is 226256-56-0, its structure is as follows: [0003] [0004] Cinacalcet hydrochloride, prepared from cinacalcet through hydrochloric acid salification, molecular formula is C 22 h 22 f 3 N . HCl, CA No. 364782-34-3, trade name Spensipar.Mimpara, is the first FDA-approved calcimimetic drug for the treatment of secondary hyperparathyroidism in dialysis patients with chronic kidney disease. At the physiological concentration (5 mmol) of extracellular calcium ions, it can dose-dependently enhance the sensitivity of calcium-sensing receptors (CaR) to extracellular calcium ions, inhibit the secretion of PTH, and reduce the calcium-phosphorus prod...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C211/30C07C209/08C07C209/22
Inventor 吴范宏杨雪艳汤才飞
Owner SHANGHAI INSTITUTE OF TECHNOLOGY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products