Method for producing important steroid hormone dexamethasone methyl tetraenes intermediate

A technology of isomethyltetraene and dexamethasone is applied in the production field of important intermediate methyltetraene, which can solve the problems of severe conditions, flammable and explosive materials, poor product quality, etc.

Inactive Publication Date: 2011-02-23
TIANJIN JINHUI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Its production method has severe conditions, many flammable and explosive items, high risk, serious environmental pollution, low yield, poor product quality, and is not suitable for large-scale industrial production.

Method used

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  • Method for producing important steroid hormone dexamethasone methyl tetraenes intermediate
  • Method for producing important steroid hormone dexamethasone methyl tetraenes intermediate
  • Method for producing important steroid hormone dexamethasone methyl tetraenes intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add 30g of mold dehydrogenation product and 280ml of solvent tetrahydrofuran into the reactor, lower the temperature to -50°C, keep this temperature, add 30g of new dehydrating agent phosphorus pentachloride, and keep it warm for 3.5 hours until it is identified by thin layer chromatography (TLC). If there is no raw material point, the reaction liquid is dispersed in 50 times of ice water, neutralized with alkali to pH ≈ 7, left standing, filtered, and dried to obtain the dehydrated product. Dissolve the methyl dehydrate in ethanol, use 2 times of chromium trichloride and 0.4 times of zinc powder as the reducing agent, add the reducing agent at a low temperature of -5°C, keep the temperature, react for 1 hour, then concentrate, recover the ethanol, stand still, Shake the material and dry to obtain a crude methyl tetraene product with a dehydration yield of 85.2%, and then refine it to obtain a 5ST fine product with a maximum purity of 0.75%.

Embodiment 2

[0023] Add 30g of mold dehydrogenation product and 180ml of solvent tetrahydrofuran into the reactor, lower the temperature to -50°C, keep this temperature, add 30g of new dehydrating agent phosphorus pentachloride, and keep it warm for 3.5 hours until it is identified by thin layer chromatography (TLC). If there is no raw material point, the reaction liquid is dispersed in 50 times of ice water, neutralized with alkali to pH ≈ 7, left standing, filtered, and dried to obtain the dehydrated product. Dissolve the methyl dehydrate in ethanol, use 5 times of chromium trichloride and 0.4 zinc powder as the reducing agent, add the reducing agent at a low temperature of -15°C, keep the temperature, react for 8 hours, then concentrate, recover the ethanol, let stand, shake Material, drying, the crude methyl tetraene was obtained, the dehydration yield was 85.8%, and then refined to obtain the 5ST fine product, the maximum purity was 0.82%.

Embodiment 3

[0025] Add 30g of mold dehydrogenation product and 220ml of solvent tetrahydrofuran into the reactor, lower the temperature to -60°C, keep this temperature, add 42g of new dehydrating agent phosphorus pentachloride, and keep it warm for 3.5 hours until it is identified by thin layer chromatography (TLC). If there is no raw material point, the reaction liquid is dispersed in 50 times of ice water, neutralized with alkali to pH ≈ 7, left standing, filtered, and dried to obtain the dehydrated product. Dissolve the methyl dehydrate in ethanol, use 9 times of chromium trichloride and 4 times of zinc powder as the reducing agent, add the reducing agent at a low temperature ~ 20°C, keep the temperature, react for 5 hours, then concentrate, recover the ethanol, at 20 Stand still in double diluted water, shake the material, and dry to obtain a crude methyl tetraene product with a dehydration yield of 86.3%, and then refine it to obtain a 5ST fine product with a maximum purity of 0.76%. ...

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Abstract

The invention discloses a method for producing an important steroid hormone dexamethasone methyl tetraenes (5ST) intermediate, which comprises the following steps of: dissolving a methyl dehydrate into an organic solvent, adding a reducing agent into the solution at the temperature of between 5 DEG C below zero and 20 DEG C, and performing one-step reaction to obtain methyl tetraenes with less than 0.8 percent of single impurity, wherein the reducing agent is a mixed reducing agent of 1 to 15 weight parts of chromium trichloride and 0.2 to 8 weight parts of zinc powder. The method for producing the 5ST shortens the reduction reaction into one-step reaction from three-step reaction so as to save the reaction time and facilitate the operation. The method reduces the consumption of chemical raw materials and dangerous goods, reduces the environmental pollution, and reflects the environment-friendly idea of green chemistry.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and relates to a production method of an important intermediate methyltetraene (5ST) of a steroid hormone dexamethasone product. Background technique [0002] Like other glucocorticoids, dexamethasone has pharmacological effects such as anti-inflammation, anti-endotoxin, immune suppression, anti-shock and enhancement of stress response, so it is widely used in various departments to treat various diseases, such as autoimmune diseases, allergies , Inflammation, asthma and dermatology, eye diseases. Dexamethasone sodium phosphate injection is an indispensable first-aid medicine for rescuing critically ill patients. For more than ten years, clinicians have used dexamethasone sodium phosphate to treat and prevent drug allergies caused by various Chinese and Western medicines and to treat fever caused by viral influenza, etc. The clinical dosage of dexamethasone has increased year by year, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
Inventor 程绍国王悦伟李玉兰陈松芸董永明
Owner TIANJIN JINHUI PHARMA
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