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Improved synthesis method for hydrochloric acid acotiamide

A technology of acotiamide hydrochloride and a synthesis method, which is applied in the field of synthesis of acotiamide hydrochloride, can solve the problems of complicated post-processing, high production cost, low conversion rate of raw materials, etc., and achieves stable product quality, low price, and purity. high effect

Pending Publication Date: 2019-04-12
KAIFENG PHARMA GRP +1
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  • Claims
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Problems solved by technology

[0008] The purpose of the present invention is to overcome the shortcomings of using highly toxic chlorinated reagents and expensive condensing agents, low conversion rate of raw materials, complicated post-treatment and high production cost in the above-mentioned prior art, and provides an improved method for preparing acotihydrochloride. Synthesis of Amines

Method used

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  • Improved synthesis method for hydrochloric acid acotiamide
  • Improved synthesis method for hydrochloric acid acotiamide
  • Improved synthesis method for hydrochloric acid acotiamide

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Embodiment

[0027] (1) Add 2,4,5-trimethoxybenzoic acid (106g, 0.5mol) and sodium hydroxide (40g, 1mol) to 1500mL of methanol, stir for half an hour, and slowly add 62.3mL of methyl iodide dropwise at room temperature (1mol), the dropwise addition was completed, the system was heated to 50° C., and reacted for 5 hours, and the reaction was completed. The system was cooled to room temperature, concentrated under reduced pressure, added 2000 mL of water, and extracted with ethyl acetate (1500 mL×3). The organic phases were combined, washed with water (2000 mL×3), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain intermediate 2 with a yield of 99%.

[0028] (2) Intermediate 2 (22.6g, 0.1mol) and 250mL of methanol solvent were placed in a 500mL three-necked flask, and 80% by mass hydrazine hydrate (9.4g, 0.15mol) was slowly added at room temperature, heated to reflux, The reaction was stirred for 6 hours, and the reaction was completed. The sys...

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Abstract

The invention relates to an improved synthesis method for hydrochloric acid acotiamide, and belongs to the field of pharmaceutical chemistry. A cheap compound 1 of 2,4,5-trimethoxybenzoic acid servesas a raw material and is esterfied to obtain an intermediate 2, the intermediate 2 reacts with hydrazine hydrate to generate an intermediate 3, under the acid catalysis, the intermediate 3 reacts withammonium thiocyanate to prepare an intermediate 4, the intermediate 4 reacts with 3-bromine-2-oxopropanoate or 2-chlorine-3-oxopropanoate to generate an intermediate 5 through cyclization, the intermediate 5 and N,N-diisopropyl ethylenediamine are subjected to one-pot ester ammonolysis and demethylation reactions to generate acotiamide, and hydrochloric acid acotiamide 6 is prepared through acidification of concentrated hydrocoloric acid. The adopted raw material is cheap and easy to get, a reaction solvent can be recycled, aftertreatment operation is convenient, the yield and purity are high, particularly, hypertoxic chloride agents and expensive condensing agents are omitted, the ester ammonolysis and demethylation relations are further carried out in one step, the synthesis path is simplified, the cost is reduced, and large-scale industrial production is facilitated. The structure of hydrochloric acid acotiamide is shown in the description.

Description

technical field [0001] The invention relates to a synthesis method of acotiamide hydrochloride, which belongs to the field of medicinal chemistry. Background technique [0002] Acotiamide hydrochloride, chemical name: N-[2-bis(1-methylethyl)aminoethyl]-2-(2-hydroxy-4,5-dimethoxybenzoyl)aminothiazole -4-Carboxamide hydrochloride, a new type of M1 and M2 receptor antagonist jointly developed by Zeria Shinyaku Kogyo Co., Ltd. and Astellas Pharmaceutical Co., Ltd. in June 2013 Approved for marketing, it becomes the first new drug for the treatment of functional dyspepsia (FD). It is mainly used to improve gastric motility disorder and delayed gastric emptying, thereby improving FD symptoms, including postprandial fullness, upper abdominal distension, and early satiety. As the world's first drug for the treatment of FD, this drug has attracted widespread attention and has a broad market prospect. [0003] At present, the method for synthesizing acotiamide hydrochloride has the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/56
CPCC07D277/56
Inventor 李旭光杨蕾丁红强王新军任立志崔浩朱慧峰罗琦
Owner KAIFENG PHARMA GRP
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