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A kind of preparation method of teprenone

A technology of teprenone and acetylmelonic acid, which is applied in the field of drug synthesis technology, can solve the problems of being unable to determine whether it can be used in clinical practice, unable to directly use in actual production, and cumbersome post-processing process, so as to facilitate popularization and application , easy to control, simple method effect

Active Publication Date: 2016-02-03
乐声药业石家庄有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, teprenone commonly used in the industry is prepared by carroll reaction, but this preparation method has many defects such as high reaction temperature, many by-products, cumbersome post-treatment process, and easy emulsification.
KathliaADeCastro et al prepared teprenone (Bull.KoreanChen.Soc.2009, Vol.30, No.9) by using geranyl linalool and acetylmelonic acid under the catalysis of aluminum isopropoxide; The teprenone is the all-trans form, which is inconsistent with the configuration of the teprenone drug sold on the market, so it is impossible to determine whether it can be used clinically, and it cannot be directly used in actual production; and the conversion rate of this method is relatively low. Low, the purification of its crude product adopts column chromatography, which also limits its popularization and application in actual production

Method used

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  • A kind of preparation method of teprenone
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  • A kind of preparation method of teprenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 100 mL of geranyllinalool (0.3 mol), 68 g of acetylmelonic acid (0.36 mol) and 6.2 g of aluminum isopropoxide (0.03 mol) into the flask, and dissolve them in 600 mL of p-xylene. The flask was immersed in an oil bath preheated to 150°C and stirred for 8 hours. The reaction mixture was cooled to room temperature, concentrated with a rotary evaporator, and 50 mL of NaHCO with a concentration of 5% by mass 3 solution, washed with 300 mL of CH 2 Cl 2 Extract three times, combine the organic layers, and wash the organic phase with anhydrous MgSO 4 dry. Filtration, concentration, and molecular distillation of the concentrated solution, the feed rate is 2mL / min, the feed inlet temperature is 70°C, the heating temperature is 140°C, and the vacuum degree is 2.5Pa. The organic phase after molecular rectification is further reduced by a packed tower. Pressure distillation, the vacuum degree of the oil pump is 10Pa, glass filler, the rectification reflux ratio is gradually i...

Embodiment 2

[0028] Add 100 mL of geranyllinalo (0.3 mol), 85 g of acetylmelonic acid (0.45 mol) and 6.2 g of aluminum isopropoxide (0.03 mol) into the flask, and dissolve them in 200 mL of p-xylene. The flask was immersed in an oil bath preheated to 160°C and stirred for 6 hours. The reaction mixture was cooled to room temperature, concentrated with a rotary evaporator, and 50 mL of NaHCO with a concentration of 5% by mass 3 solution washed with 600 mL of CH 2 Cl 2 Extract three times, combine the organic layers, and wash the organic phase with anhydrous MgSO 4 dry. Filtration, concentration, and molecular distillation of the concentrated solution, the feed rate is 2mL / min, the feed inlet temperature is 60°C, the heating temperature is 160°C, and the vacuum degree is 10Pa. The organic phase after molecular rectification is further decompressed by a packed tower Distillation, the vacuum degree of the oil pump is 5Pa, glass packing, the rectification reflux ratio is gradually increased ...

Embodiment 3

[0030] Add 100 mL of geranyllinalool (0.3 mol), 85 g of acetylmelonic acid (0.45 mol) and 3.1 g of aluminum isopropoxide (0.015 mol) into the flask, and dissolve them in 400 mL of p-xylene. The flask was immersed in an oil bath preheated to 160°C and stirred for 10 hours. The reaction mixture was cooled to room temperature, concentrated with a rotary evaporator, and 50 mL of NaHCO with a concentration of 5% by mass 3 solution, washed with 300 mL of CH 2 Cl 2 Extract three times, combine the organic layers, and use anhydrous MgSO for the organic phase 4 dry. Filtration, concentration, and molecular distillation of the concentrated solution, the feed rate is 2mL / min, the feed inlet temperature is 60°C, the heating temperature is 140°C, and the vacuum degree is 2.5Pa. The organic phase after molecular rectification is further reduced by a packed tower. Pressure distillation, the vacuum degree of the oil pump is 8Pa, glass packing, the rectification reflux ratio is gradually i...

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Abstract

The invention discloses a method for preparing teprenone. The method comprises the following steps: (a) mixing geranyl linalool, acetyl Meldrum's acid and aluminum isopropoxide according to a molar ratio of 1: (1.2-1.5): (0.02-0.1), dissolving the mixture in a paraxylene solvent, heating up to 50-160 DEG C, refluxing for 6-10 hours, cooling and removing the solvent to obtain a teprenone mixture; (b) washing and extracting the teprenone mixture, mixing organic layers, and drying to obtain a crude product of teprenone; (c) carrying out molecular distillation, impurity removal, decompression rectifying and impurity removal on the crude product of teprenone to obtain a teprenone product. The method is simple and easy to control, the conversion rate of the product is high, and the prepared product is high in purity, stable in quality and high in safety, thereby being convenient to promote and use in clinical and industrial production.

Description

technical field [0001] The invention relates to a synthesis process of medicine, in particular to a preparation method of teprenone. Background technique [0002] Teprenone (chemical name 6,10,14,18-tetramethyl-5,9,13,17-nonadecanetraen-2-one) is a terpene compound with broad-spectrum anti- Ulcer drug is a new type of protective agent for gastric mucosa that directly increases mucus secretion and promotes cell regeneration. It has unique physical and chemical properties and a good anti-ulcer mechanism. Synthesis and secretion of protein and phospholipids, increase bicarbonate in gastric mucus, improve gastric mucosal blood flow, and have good curative effects on acute gastritis, chronic gastritis and gastric ulcer. Teprenone sold as a commercial drug is generally a mixture of cis-trans isomers (5E / 5Z=3:2), which has the advantages of small side effects, high safety and stable drug efficacy in clinical application. [0003] At present, teprenone commonly used in the industr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/203C07C45/60C07C45/82C07C45/78
CPCC07C45/60C07C49/203
Inventor 张丽芳房桂珍秦旭荣
Owner 乐声药业石家庄有限公司
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