A new process for preparing lafutidine

A technology of lafutidine and butene, applied in the field of medicine and biology

Active Publication Date: 2011-12-14
SICHUAN KELUN PHARMA RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] But the cost of lafutidine prepared by the current method is large, and the yield is low, which is unfavorable for large-scale industrial production

Method used

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  • A new process for preparing lafutidine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] A. Preparation of 4-[4-(piperidin-1-yl-methylene)pyridin-2-yl-oxygen]-2(Z)-butene-1-amine Weigh 0.232g cis-4-chlorobutane Diene-1-amine hydrochloride was suspended in 10ml of dichloromethane, 0.5ml of triethylamine was added at room temperature, stirred until the solution was clear, and then 10ml was added to dissolve 2g of 4-(piperidin-1-yl-methylene) The dichloromethane solution of pyridin-2-ol is stirred at room temperature or under reflux until TLC shows that the reaction of compound 4-(piperidin-1-yl-methylene)pyridin-2-ol is complete, and the silica gel column chromatography is separated, and the chromatographic solution For methanol: ethyl acetate=1:10, the compound 4-[4-(piperidin-1-yl-methylene)pyridin-2-yl-oxygen]-2(Z)-butene-1-amine 1.6g;

[0032] B. Preparation of 2-(2-furanmethylsulfoxide)acetic acid Dissolve 0.342g of 2-(furan-2-methyl)thioacetic acid in 10ml of ethanol, add 0.0004g of ammonium molybdate, stir for 10 minutes, at 25°C Next, add 0.7ml30% H...

Embodiment 2

[0035] A. Preparation of 4-[4-(piperidin-1-yl-methylene)pyridin-2-yl-oxygen]-2(Z)-butene-1-amine Weigh 0.28g cis-4-chlorobutyl Diene-1-amine hydrochloride was suspended in 9ml of dichloromethane, 0.5ml of triethylamine was added at room temperature, stirred until the solution was clear, and 2.5g of 4-(piperidin-1-yl-methylene ) dichloromethane solution of pyridin-2-ol, stirred at room temperature until TLC showed that the reaction of compound 4-(piperidin-1-yl-methylene) pyridin-2-ol was completed, and the silica gel column chromatography was separated, and the chromatographic solution was Methanol: ethyl acetate = 1:10, the compound 4-[4-(piperidin-1-yl-methylene)pyridin-2-yl-oxygen]-2(Z)-butene-1-amine 2.0 g;

[0036] B. Preparation of 2-(2-furanmethylsulfoxide)acetic acid Dissolve 0.32g of 2-(furan-2-methyl)thioacetic acid in 11ml of ethanol, add 0.0007g of ammonium molybdate, stir for 8 minutes, at 25°C Next, add 0.0005ml30% H2O2, heat preservation reaction 12 minutes, a...

Embodiment 3

[0039] A. Preparation of 4-[4-(piperidin-1-yl-methylene)pyridin-2-yl-oxygen]-2(Z)-butene-1-amine Weigh 0.22g cis-4-chlorobutane Diene-1-amine hydrochloride was suspended in 11ml of dichloromethane, 0.6ml of triethylamine was added at room temperature, stirred until the solution was clear, and 9ml of 4-(piperidin-1-yl-methylene ) dichloromethane solution of pyridin-2-ol, room temperature or reflux stirring until TLC shows that compound 4-(piperidin-1-yl-methylene) pyridin-2-ol has reacted completely, separated by silica gel column chromatography, chromatographically The solution is methanol: ethyl acetate=1:10, to obtain the compound 4-[4-(piperidin-1-yl-methylene)pyridin-2-yl-oxygen]-2(Z)-butene-1- Amine 2.5g;

[0040] B. Preparation of 2-(2-furanmethylsulfoxide)acetic acid Dissolve 0.38g of 2-(furan-2-methyl)thioacetic acid in 9ml of ethanol, add 0.0006g of ammonium molybdate, stir for 8 minutes, at 25°C Next, add 0.0007ml30% H2O2, heat preservation reaction 8 minutes, add ...

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Abstract

The invention relates to a preparation method for lafutidine, and the technology comprises the following steps: preparing 4-[4-(piperidine-1-group-methylene)pyridine-2-group-oxygen]-2(Z)-butylene-1-amine and preparing 2-(2-furans methyl sulfoxide group)acetate, then dissolving 2-(2-furans methyl sulfoxide group)acetate into methylene chloride at the room temperature, and then adding a methylene chloride solution possessing 4-[4-(piperidine-1-group-methylene)pyridine-2-group-oxygen]-2(Z)-butylene-1-amine at the room temperature, stirring and separating to obtain lafutidine. The preparation method of lafutidine of the invention modifies the original route, wherein the reaction is milder and easy to operate without using sodium hydride, the intermediate fragment employs a nontoxic and innocuous molybdenum tungsten metal for catalyzing, the reaction condition is milder, the environmental pollution can be reduced and the reaction cost can be decreased.

Description

technical field [0001] The invention relates to a preparation method of chemical drugs, in particular to a preparation method of lafutidine, which belongs to the field of medical biotechnology. Background technique [0002] Digestive system disease is one of the more common frequently-occurring diseases, and the total incidence rate accounts for 10% to 20% of the total population. The main diseases include acute gastritis, chronic gastritis, peptic ulcer, functional dyspepsia, etc. Among them, functional dyspepsia and peptic ulcer are the most common. [0003] At present, the drugs for treating peptic ulcer are mainly divided into two categories, that is, drugs that reduce gastric acid (weaken the attack factor) and drugs that protect the mucosa (enhance the defense factor). Among them, gastric acid-reducing drugs are now clinically mainly based on proton pump inhibitors and H 2 Receptor antagonists are the main drugs, and these two drugs are also the main force in the tre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12
Inventor 田添冷盛东李大雄
Owner SICHUAN KELUN PHARMA RES INST CO LTD
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