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Method for simply and efficiently synthesizing dinoprost

A dinoprost and high-efficiency technology, applied in the field of pharmaceutical preparation, can solve the problems of complicated operation, difficult to realize industrialization, and high cost, and achieve the effects of reducing the operation process, reducing the cost of the solvent, and improving the reaction yield

Active Publication Date: 2018-05-29
厦门欧瑞捷生物科技有限公司
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

Therefore, it has many disadvantages: long steps, low yield and high cost; at the same time, intermediate purification methods and impurity control are also barriers to industrialization.
[0006] Chinese patent application-"Synthetic method of trometamol prostaglandin F2α" (public date: June 9, 2017) involves the synthesis and preparation of prostaglandin F2α. When this preparation method is used to prepare prostaglandin F2α, the yield is low. Complicated operation

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  • Method for simply and efficiently synthesizing dinoprost
  • Method for simply and efficiently synthesizing dinoprost
  • Method for simply and efficiently synthesizing dinoprost

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Embodiment

[0060] The specific synthesis steps are as figure 1 Shown:

[0061] Step (1) Preparation of Compound I

[0062] In a 10L three-necked flask equipped with a constant pressure dropping funnel, a thermometer and a mechanical stirrer, respectively add Cory lactone diol (500g, 2.907mol), DMN-AZADO (4.93g, 0.02907mol), potassium bromide KBr (34.59 g, 0.2907mol), n-Bu4NBr (47.8g, 0.1454mol), dichloromethane (5L) and saturated sodium bicarbonate solution (400mL); then use an ice-salt bath to cool the above mixed system to an internal temperature ≤ 0°C , and stirred at a constant temperature for 10 minutes; then NaClO (3.4884mol, used as an oxidizing agent) solution was slowly added dropwise to the reaction system, controlling the reaction temperature not higher than 5°C; after the addition was completed, stirred at a constant temperature for 30 minutes. After the reaction, add saturated Na to the system 2 S 2 o 3 (neutralizing excess oxidant) (1000 mL) quenched the reaction, and ...

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Abstract

The invention provides a method for simply and efficiently synthesizing dinoprost. The method comprises synthesis steps as follows: L-corey lactone diol is selectively oxidized to aldehyde-containingcorey lactone monols, namely, a compound I; the compound I and dimethyl(2-oxoheptyl)phosphonate are subjected to a Honel-Wadsworth-Emmons reaction, and a reactive product compound II is produced; lactone is reduced to alcohol, and an intermediate, namely, a compound III, is obtained; the intermediate III selectively oxidizes primary alcohol, and an intermediate, namely, a compound IV, is obtained;the compound IV is subjected to a Witting reaction, and the dinoprost is produced. According to the method for simply and efficiently synthesizing dinoprost, raw materials are simple and easy to obtain, and equipment requirements are simple; the steps are short, and industrial production is easy to realize; no heavy metals or other strong carcinogens are used in the whole process; an intermediatepurification method is simple and impurities are easy to control.

Description

technical field [0001] The invention relates to the field of medicine preparation, in particular to a simple and efficient method for synthesizing dinoprost. Background technique [0002] Prostaglandins (PGs for short) are a class of important endogenous products with a wide range of physiological activities. PGs were first discovered and named by American scholar Von Eluer in 1930. In 1962, Bergstorm extracted two pure PGs (PGF1 and PGF2.) and determined their chemical structures. In 1969, Willis first proposed that PGs are an inflammatory mediator in the body. Subsequently, various physiological and pharmacological activities of PGs have been deeply studied. It exists in the tissues of almost all mammals, plays an important role in the reproductive system, digestive system, respiratory system and cardiovascular system, and participates in physiology and pathology such as temperature regulation, inflammatory response, glaucoma, pregnancy, hypertension, ulcer and asthma p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C405/00
CPCC07B2200/07C07C29/147C07C405/00C07D307/935C07C35/06
Inventor 郑飞剑张江平赵欢张立军王萍陈思涵赖育来吴进泉
Owner 厦门欧瑞捷生物科技有限公司