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Preparation method of drug, namely teneligliptin for treating diabetes mellitus

A technology for compounds and intermediates, applied in the field of preparation of the drug Terliliptin, can solve the problems of many impurities, cumbersome post-processing, low reaction yield and the like, achieve high product purity, avoid side reactions, and be beneficial to industrial production. Effect

Active Publication Date: 2019-06-28
THE SECOND PEOPLES HOSPITAL OF SHENZHEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The technical problem to be solved by the present invention is aimed at the problems in the prior art that a large amount of organic amines are used in the deprotection process of the terililiptin intermediate, resulting in low reaction yield, many impurities, and cumbersome post-treatment.

Method used

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  • Preparation method of drug, namely teneligliptin for treating diabetes mellitus
  • Preparation method of drug, namely teneligliptin for treating diabetes mellitus
  • Preparation method of drug, namely teneligliptin for treating diabetes mellitus

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preparation example Construction

[0022] The invention discloses a preparation method of terililiptin, and those skilled in the art can learn from the content of this article and appropriately improve the process parameters to realize it. It needs to be pointed out that all similar replacements and modifications are obvious to those skilled in the art, and they are all considered to be included in the present invention, and relevant personnel can obviously make changes without departing from the content, spirit and scope of the present invention. Changes or appropriate changes and combinations are made to the content described herein to realize and apply the technology of the present invention.

[0023] In the present invention, unless otherwise specified, the scientific and technical terms used herein have the meanings commonly understood by those skilled in the art.

Embodiment 1

[0026]

[0027] At room temperature, in 120mL of dichloromethane, under nitrogen protection, add 3.18g (5.0mmol) of intermediate compound A, then add 0.98g (6.0mmol) of trichloroacetic acid and 0.94g (10.0mmol) of phenol under stirring, TLC monitoring Reaction, after the reaction is completed, adjust the pH value of the system to 8 with saturated sodium bicarbonate solution, separate liquids, wash the organic phase with water, wash with saturated sodium chloride, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and add isopropyl ether dropwise to the concentrated solution , crystallized, filtered, and vacuum-dried to obtain 1.98g (4.8mmol) of the product terililiptin, with a yield of 96%, and a content determined by HPLC of 99.67%.

Embodiment 2

[0029] At room temperature, in 150mL acetonitrile, under nitrogen protection, add 4.44g (7.0mmol) intermediate compound A, then add 1.63g (10.0mmol) trichloroacetic acid and 2.27g (21.0mmol) anisole under stirring, TLC monitors the reaction , after the reaction is completed, adjust the pH value of the system to 8 with a saturated sodium bicarbonate solution, separate the liquid, wash the organic phase with water, wash with saturated sodium chloride, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and add isopropyl ether dropwise to the concentrated solution. Crystallization, filtration, and vacuum drying yielded 2.76 g (6.7 mmol) of the product terililiptin, with a yield of 95%, and a content determined by HPLC of 99.66%.

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Abstract

The invention belongs to the synthesis field of Western medicines and particularly discloses a preparation method of a drug, namely teneligliptin for treating diabetes mellitus. According to the preparation method, amide protecting groups are removed in the presence of trichloroacetic acid and carbocation, so that the reaction yield is increased, the impurity residue in the product is avoided, theacquired product is relatively high in purity, and the industrial production is promoted.

Description

technical field [0001] The application relates to a preparation method of teroliliptin, a drug for treating diabetes, and belongs to the field of western medicine synthesis. Background technique [0002] In recent years, the incidence of diabetes has increased year by year, and diabetes has become another non-communicable disease that seriously threatens human health after cardiovascular diseases and malignant tumors. The type II incidence of diabetes accounts for 90%, and the pathogenesis of type II diabetes is mainly caused by the human body's resistance to insulin and insulin and cell function defects. Clinically used drugs for the treatment of type II diabetes mainly include insulin secretion promoters, sulfonylureas, meglitinides, insulin sensitizers, insulin and insulin receptor agonists and dipeptidyl peptidase-4 inhibitors . [0003] Teneligliptin, the chemical name is 3-[[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)-1-piper Azinyl]-2-pyrrolidinyl]formyl]thiaz...

Claims

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Application Information

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IPC IPC(8): C07D417/14
CPCY02P20/55
Inventor 阎德文谭回李海燕刘雪婷李明政吴阳
Owner THE SECOND PEOPLES HOSPITAL OF SHENZHEN
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