Cetilistat efficient synthesizing method

A synthetic method and relatively high technology, applied in the high-efficiency synthetic field of new lixistat, can solve problems such as unfavorable industrial production, low product yield, and harsh conditions, so as to improve purity, reduce production cost, and increase yield Effect

Active Publication Date: 2016-08-24
NANJING HEALTHNICE MEDICAL TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The product yield that above report obtains is not high, and route 1, route 2 use column purification, route 3 needs the operation of high pressure, and condition is relatively harsh, is unfavorable for industrialization into production

Method used

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  • Cetilistat efficient synthesizing method
  • Cetilistat efficient synthesizing method
  • Cetilistat efficient synthesizing method

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Synthesis of compound formula (II) 2-hexadecyloxycarbonylamino-5-methylbenzoic acid.

[0027] Under N2 protection, add 20.2g of 2-amino-5-methylbenzoic acid and 180ml of pyridine to a 1L three-necked flask, stir to dissolve, add dropwise a mixture of 47g of hexadecyl chloroformate and 220ml of toluene into the system at 20-30°C solution (about 30min), react at 20-30°C until the reaction of the raw material 2-amino-5-methylbenzoic acid is completed, and terminate the reaction. Add 600ml of toluene and 200ml of ethyl acetate to the system, and wash with 200ml of 10% citric acid aqueous solution. Once, wash twice with 200ml water, dry the organic phase with 30g anhydrous sodium sulfate for 2h, filter, rinse the anhydrous sodium sulfate filter cake with 30ml×2 toluene, concentrate the filtrate (T=60°C, P=0.09MPa), and dry After that, 87g of yellow liquid was obtained

[0028] Refining: Add 260ml of n-heptane to the concentrated solution, stir for 10 minutes after the solid...

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Abstract

The invention provides a method for efficiently synthesizing 2-hexadecyloxy-6-methyl-4H-3,1-benzoxazine-4-ketone. A reaction is thorough and complete, the reaction time is short, the yield is high, industrial production is easy to achieve, and industrial production cost is reduced.

Description

technical field [0001] The present invention relates to the efficient synthesis of compound formula (I) 2-hexadecyloxy-6-methyl-4H-3,1-benzoxazin-4-ketone [hereinafter sometimes also referred to as Neolistat] method. [0002] Background technique [0003] Cetilistat was jointly developed by Takeda and Norgine. It was approved for marketing in Japan in September 2013. It is taken orally and is used to treat obesity and its complications. The original research patent WO 2000040247 has announced two preparation methods of the compound, route 1: wherein the compound formula (IV) 2-amino-5-methylbenzoic acid and the compound formula (V) hexadecyl chloroformate are reacted in one step The compound formula (I) was obtained, and the yield after column purification was 15%. Route 2: another by compound formula (II) 2-hexadecyloxycarbonylamino-5-methylbenzoic acid and compound formula to compound formula (V) chloroformic acid compound formula hexadecyl ester and compound formula ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/26C07C269/04C07C271/28
Inventor 张明雨王华娟
Owner NANJING HEALTHNICE MEDICAL TECH
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