Method for preparing Adapalene

An equation and reaction technology, applied in the preparation of carboxylate/lactone, organic chemistry, etc., can solve the problems of resource consumption, serious three wastes, and high cost, and achieve the effect of reducing costs, reducing resource consumption, and reducing three wastes

Inactive Publication Date: 2006-09-13
JIANGSU ZHONGDAN GROUP +2
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  • Abstract
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Problems solved by technology

Document US4717720 reports the laboratory synthesis of adapalene, using sodium and methanol to prepare sodium methoxide for hydrolysis, the yield is 78%, but industrial production is difficult, and the cost is high, the three wastes are serious, and resource consumption
Another document (Chinese Journal of Pharmaceutical Industry, 2005, 36 (12) the synthesis of adapalene) reports that 95% methanol using sodium hydroxide is hydrolyzed, but the yield is 51%

Method used

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  • Method for preparing Adapalene
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  • Method for preparing Adapalene

Examples

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Embodiment Construction

[0011] In a 250ml four-necked flask, add 2.2g of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2 naphthoic acid methyl ester and 50ml of tetrahydrofuran, methanol, ethanol or acetone, heat Make it dissolve, then add the prepared potassium hydroxide solution (50ml water and 2gKOH), reflux reaction for 2 hours (TLC tracking reaction), after the reaction is complete, concentrate to remove tetrahydrofuran, and the temperature is raised to 80°C to complete precipitation. Add 100 ml of water to the residue, filter to obtain a solid, wash with water until neutral, add the solid to 100 ml of water, acidify to pH 1 with concentrated hydrochloric acid, stir for 1.5 hours, and filter to obtain a crude product. The crude product was recrystallized from a mixed solvent of ethyl acetate and tetrahydrofuran to obtain 1.9 g of the product with a yield of 89.3%.

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Abstract

A process for preparing adapalene features the hydrolyzing reaction between 6[3-(1-adamantyl)-4methoxyphenyl]-2-methyl naphthanleneformate and one or more of potassium hydroxide, ammonia water and potassium carbonate in polar solvent.

Description

technical field [0001] The invention relates to a preparation method for adapalene obtained from alkaline hydrolysis of methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoate in a polar solvent. Background technique [0002] Adapalene (adapalene), chemical name 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid, is an aryl propionic acid derivative, a new naphthalene Formic acid derivatives, belonging to the third generation of retinoic acid drugs, are selective β-retinoic acid receptor agonists, and are clinically used to treat acne and psoriasis. At present, foreign countries have industrialized production, and my country basically relies on imports, only a small amount of self-production, but the cost is relatively high, and the three wastes are serious. Document US4717720 reports the laboratory synthesis of adapalene, using sodium and methanol to prepare sodium methoxide for hydrolysis, the yield is 78%, but industrial production is difficult, and the cost is high, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C65/26
Inventor 张家庆陈捷周春红翟富荣周玉琢龚熙见
Owner JIANGSU ZHONGDAN GROUP
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