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Preparation method of pyrindole enantiomer and salt thereof

An enantiomer, pyridindole technology is applied in the field of preparing pyridindole enantiomer or its medicinal salt, and can solve the problems of low exothermic activity and the like

Active Publication Date: 2022-05-03
TECHNIMED SOC TECH MEDICINAL SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Accelerated calorimetry (ARC) testing shows exothermic activity down to 26°C

Method used

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  • Preparation method of pyrindole enantiomer and salt thereof
  • Preparation method of pyrindole enantiomer and salt thereof
  • Preparation method of pyrindole enantiomer and salt thereof

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Experimental program
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Embodiment Construction

[0054] The present invention provides a method for the synthesis of the enantiomers of pyrindole which can be easily converted into the corresponding acid salts.

[0055] In one embodiment, the method of the present invention uses the intermediate compound of formula VI (S)-6-methyl-N-((S)-1-phenylethyl)-2,3,4,9-tetra Hydrogen-1H-carbazol-1-amine

[0056]

[0057] Compounds of formula VI can be prepared in two steps:

[0058] Compound 6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-ketone of formula IV and chiral auxiliary agent (S)-(-)-α-methylbenzylamine 1- condensation,

[0059]

[0060] Then: 2-stereoselective reduction with sodium borohydride.

[0061] Compounds of formula VI can be cyclized to produce compounds of formula VII (S)-8-methyl-3-((S)-1-phenylethyl)-2,3,3a,4,5,6-hexahydro- 1H-Pyrazino[3,2,1-jk]carbazole

[0062]

[0063] It can be subjected to catalytic hydrogenolysis to give compound (S)-pirindole of formula III.

[0064] In one embodiment, the prese...

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Abstract

The present invention relates to an improved process for the preparation of pyrindole enantiomers or pharmaceutically acceptable salts thereof.

Description

technical field [0001] The present invention relates to an improved process for the preparation of pyrindole enantiomers or pharmaceutically acceptable salts thereof. Background technique [0002] Also known as Pyrazidole TM The pyrindole (pirlindole) (8-methyl-2,3,3a,4,5,6-hexahydro-1H-pyrazino[3,2,1-jk]carbazole) of formula I [0003] [0004] Represents a new class of original tetracyclic antidepressants, pyrazinocarbazole derivatives. The drug was synthesized and characterized in the late 1960s and was marketed as an antidepressant in 1975. Current clinical trials have proven that it is a highly effective short-acting (short-acting, short-acting) and safe drug. [0005] Pirindole is a selective and reversible inhibitor of MAO-A. In vitro evidence suggests that MAO-A can catalyze the oxidation of pyrindole to dehydropyrindole. Dehydropyrindole may be a more potent slowly reversible inhibitor of MAO-A, and this may explain the persistence of the in vivo inhibitory ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04C07D487/06
Inventor 卡拉·帕特里恰·达·科斯塔·佩雷拉·罗萨乔奥·卡洛斯·拉莫斯·达米尔阿纳·瓦妮莎·科代罗·西莫斯乔奥·佩德罗·席尔瓦·塞拉
Owner TECHNIMED SOC TECH MEDICINAL SA