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Method for preparing acotiamide hydrochloride trihydrate

A technology for acotiamide hydrochloride trihydrate and compound, which is applied in the field of preparation of pharmaceutical compounds, can solve the problems of environmentally destructive substances, low demethylation yield, side reactions, etc. Good product stability and mild reaction conditions

Active Publication Date: 2014-04-09
CHINA RESOURCES SAIKE PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of this patent are: (1) the use of thionyl chloride and ethylene dichloride are highly toxic and environmentally destructive substances; (2) the yield of demethylation is low (reported as 64.6%-86 %)
The preparation method of acotiamide refers to the above example (Example 38), and the specific yield of acotiamide is not mentioned in the text, but if the above method is used, the primary amino group of the starting material will have a side reaction

Method used

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  • Method for preparing acotiamide hydrochloride trihydrate
  • Method for preparing acotiamide hydrochloride trihydrate
  • Method for preparing acotiamide hydrochloride trihydrate

Examples

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Embodiment 1

[0069] Preparation of N-[2-(Diisopropylamino)ethyl]-2-N-phthalimide-1,3-thiazole

[0070] Add N,N-diisopropylethylenediamine (28.8g, 0.2mol) and 2-N-phthalimide-4-methoxycarbonyl-1,3-thiazole (54.6 g, 0.2mol), heated to 100°C for 6h, cooled to room temperature and poured the reaction mixture into isopropanol, stirred at room temperature for 10h, filtered to collect the precipitated crystals, and dried at 50°C for 10h to obtain the target Compound 73.10g, yield: 91.5%.

[0071] The LC-MS measurement ion current of the product is: 401.23 (M+1), 400.23 (23%), 399.23 (4%), elemental analysis: C content 60.13%, H content 5.99%, O content 11.99%, N content 14.01 %.

[0072] Preparation of N-[2-(Diisopropylamino)ethyl]-2-amino-1,3-thiazole

[0073] Add N-[2-(diisopropylamino)ethyl]-2-N-phthalimide-1,3-thiazole (41.4g, 0.1mol) prepared in Example 1 into the reaction flask and ethanol (1L), add hydrazine hydrate (14.6g, 0.3mol) dropwise at room temperature, react at 70°C for 8h aft...

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Abstract

The invention discloses a method for preparing an acotiamide hydrochloride trihydrate. The method comprises the following steps: 1, reacting a compound of a formula (1) and N,N-diisopropylethylamine (2) to obtain a compound (3); 2, performing two-site amino deprotection on the compound (3) to obtain a compound (4); 3, condensing the compound (4) and an acyl chloride derivative to obtain a compound (5); 4, further preparing the compound (5) to obtain the acotiamide hydrochloride trihydrate (6).

Description

technical field [0001] The patent of the present invention relates to the preparation of a pharmaceutical compound, in particular to a preparation method of acotiamide hydrochloride trihydrate, a drug for treating or preventing functional dyspepsia. Background technique [0002] Acotiamide hydrochloride, chemical name: N-[2-(diisopropylamino)ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino] -1,3-thiazole-4-carboxamide hydrochloride, usually in its trihydrate form, the structure of acotiamide hydrochloride trihydrate is as follows: [0003] [0004] Acotiamide hydrochloride trihydrate is an acetylcholinesterase inhibitor gastrokinetic drug jointly developed by Zeria Pharmaceutical Company of Japan and Astellas, that is, a drug for the treatment of functional dyspepsia. It is the first drug approved globally for the treatment of FD. The drug was first launched in Japan in June 2013 under the brand name Acofide. Functional dyspepsia (FD) refers to a group of common symptoms...

Claims

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Application Information

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IPC IPC(8): C07D277/56
CPCY02P20/55C07D277/56
Inventor 宋波黄建金李日东杨琰
Owner CHINA RESOURCES SAIKE PHARMA
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