Preparation method for prucalopride degradation impurities

Active Publication Date: 2014-04-30
连云港恒运药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And there is no synthetic report of this compound in the literature

Method used

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  • Preparation method for prucalopride degradation impurities
  • Preparation method for prucalopride degradation impurities
  • Preparation method for prucalopride degradation impurities

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Add prucalopride (1.5g) into the reaction flask, add methanol (150ml), then add 10% palladium carbon (2.0g), sodium hydroxide (1.0g), and hydrogenate at 10-30°C under normal pressure 3 days. After filtration, the filtrate was concentrated to dryness under reduced pressure to obtain Compound I (1.3 g), with a molar yield of 96%.

[0030] MS-ESI(m / z):334.33[M+H] + .

[0031] The structure was determined to be compound I by structural analysis.

Embodiment 2

[0033] Add prucalopride (1.5g) into the reaction flask, add isopropanol (150ml), then add 10% palladium carbon (2.0g), sodium hydroxide (1.0g), and add at 10-30°C under normal pressure Hydrogen reaction for 3 days. After filtration, the filtrate was concentrated to dryness under reduced pressure to obtain Compound I (1.2 g), with a molar yield of 88%.

[0034] MS-ESI(m / z):334.33[M+H] + .

[0035] The structure was determined to be compound I by structural analysis.

Embodiment 3

[0037] Add prucalopride (1.5g) into the reaction flask, add methanol (150ml), then add 10% palladium carbon (2.0g), potassium hydroxide (1.1g), hydrogenation reaction at 10-30°C under normal pressure 3 days. After filtration, the filtrate was concentrated to dryness under reduced pressure to obtain Compound I (1.2 g), with a molar yield of 88%.

[0038] MS-ESI(m / z):334.33[M+H] + .

[0039] The structure was determined to be compound I by structural analysis.

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Abstract

The invention relates to a preparation method for prucalopride degradation impurities. Particularly, the invention discloses a synthesis method for degradation impurity compound (I) of drug prucalopride (namely 4-amino-5-chloro-2,3-dihydro-N-[1-(3--methoxypropyl)-4-piperidyl]-7-benzofurancarboxamide succinate) used for treating the constipation of women, and applications in prucalopride research. According to the method, a target compound is obtained by prucalopride through hydrogenation reduction. The compound (I) can be obtained through chemical synthesis for the first time by adopting the method, and the target compound can be obtained through efficient and fast separation.

Description

technical field [0001] The present invention relates to a preparation method of 4-amino-N-[1-(3-methoxypropyl)-4-piperidinyl]-2,3-dihydrobenzofuran-7-carboxamide. The compound is a degradation impurity of prucalopride. Background technique [0002] Prucalopride is a serotonin 4 receptor agonist, which was first developed by Janssen, a subsidiary of Johnson & Johnson. In June 2007, Movetis NV obtained from Janssen the exclusive right to commercialize prucalopride in EU countries (except Bulgaria and Romania) and Switzerland / Liechtenstein. In October 2009, the European Commission (EC) approved prucarbidine succinate for the treatment of chronic constipation, and it was launched in Germany in January 2010 and in the UK in March 2010. [0003] [0004] The EMEA published the assessment report of prucalopride succinate. The report shows that three batches of commercial-scale batches of samples were subjected to stability studies under different storage conditions, including...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12
CPCC07D405/12
Inventor 冯芮茂陈亭亭乔智涛王珍珍
Owner 连云港恒运药业有限公司
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