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Preparation method of N-demethylated zolmitriptan

A technology of methylzolmitril and protan, which is applied in the field of drug synthesis and achieves the effects of easy operation and simple separation steps

Pending Publication Date: 2022-04-26
SHENZHEN SUNGENING BIO-MEDICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation method of N-desmethylzolmitriptan provided by the present invention has not been reported in the literature at present

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] In a 500ml three-neck flask, add compound I (14.3g, 50mmol) and acetone (70ml), then exchange nitrogen three times, then slowly add diethyl azodicarboxylate (26.1g, 75mmol), react at room temperature for 12h, and concentrate the reaction solution. The residue was purified by column chromatography to obtain compound II.

Embodiment 2

[0019] In a 500ml three-neck flask, add compound I (14.3g, 50mmol) and butanone (215ml), then exchange nitrogen three times, then slowly add di-tert-butyl azodicarboxylate (34.5g, 150mmol), react at 50°C for 6h, and react The solution was concentrated, and the residue was purified by column chromatography to obtain compound II.

Embodiment 3

[0021] In a 500ml three-neck flask, add compound I (14.3g, 50mmol) and acetone (180ml), then exchange nitrogen three times, then slowly add di-tert-methyl azodicarboxylate (36.5g, 250mmol), react at 0°C for 24h, and the reaction solution After concentration, the residue was purified by column chromatography to obtain compound II.

[0022] 1 H NMR (400MHz, DMSO- d 6 ) δ: 7.37 (s, 1H), 7.27 (d , 1H), 7.10 (s, 1H), 6.94 (d, 1H), 4.21-4.25 (m, 1H), 4.00-4.08 (m, 2H), 2.75 -287 (m, 6H), 2.35 (s, 3H).

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Abstract

The invention discloses a preparation method of N-demethylated zolmitriptan, the N-demethylated zolmitriptan is obtained through reaction of zolmitriptan and a demethylation reagent, the route design is reasonable, raw materials are easy to obtain, the operability is high, purification is convenient, post-treatment is simple, the preparation period is effectively shortened, the working efficiency is improved, and the method is suitable for industrial production. According to the N-demethylated zolmitriptan prepared by the invention, an important basis is provided for scientific evaluation on the quality, safety and efficiency of the zolmitriptan, and the N-demethylated zolmitriptan is good in pharmacological activity, can be developed into a medicine for treating migraine attack, and has important application value.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis and relates to a preparation method of N-desmethylzolmitriptan. Background technique [0002] Zolmitriptan, chemical name (S)-4-[3-[2-(dimethylamino)ethyl]-1H-indole-5-methyl]-2-oxazolidinone, is An anti-migraine drug developed by Glaxo-Wellcome in Germany, it is a highly selective serotonin (5-TH1B and 5-TH1D) receptor agonist, which stimulates intracranial blood vessels (including arteriovenous anastomosis) ) and 5-HTIB / ID receptors on the sympathetic nerves of the trigeminal nervous system, constrict blood vessels and inhibit the release of neuropeptides to relieve migraine attacks. At present, it has been listed in the United Kingdom, the United States and other countries, and the market prospect is good. [0003] According to public information reports, zolmitriptan is mainly metabolized by the liver into indole acetic acid, N-oxide and N-desmethyl zolmitriptan, of which indole a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/06
CPCC07D413/06
Inventor 沈歆悦李方林王志强
Owner SHENZHEN SUNGENING BIO-MEDICAL CO LTD
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