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Preparation method for [17alpha, 16alpha-d] methyl oxazoline

A methyl oxazoline steroid, the key technology, applied in the field of steroid compound preparation, can solve the problems of complex production process, poor safety, high cost, etc., and achieve the goal of simplifying operation steps, reducing production cost and improving production safety Effect

Active Publication Date: 2013-02-20
JIANGXI JUNYE BIOLOGICAL PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a preparation method of a key intermediate of deflazacort [17α, 16α-d] methyl oxazoline steroid compound, to overcome the complex production process and poor safety of the compound existing in the prior art , high cost, large pollution and other defects

Method used

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  • Preparation method for [17alpha, 16alpha-d] methyl oxazoline
  • Preparation method for [17alpha, 16alpha-d] methyl oxazoline

Examples

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Effect test

Embodiment 1

[0027] Mix 30 g of 16,17α-epoxy-pregna-20-carboxylate methyl hydrazinoacetyl-1,4-diene-3,11-dione (a) with 150 mL of chloroform and 15 mL of DMF, Add to a pressure reactor, feed ammonia gas under stirring until the pressure of the reactor reaches 0.15 MPa (control the reaction temperature at 10-15 °C during the ventilation process), keep the reaction at 30 °C, and track the reaction progress by TLC. After the reaction is complete, transfer the material liquid to a glass reaction bottle, and when the temperature of the material drops below 10°C, add acetic acid to adjust the pH to 5-6, and remove the solvent under reduced pressure; add 30 mL of acetic acid and 30 g of acetic anhydride to the reaction bottle, and react The temperature was controlled at 30 ° C, and the reaction was carried out for 6 hours. The reaction solution was poured into cold 500 mL10% sodium hydroxide solution, stirred for 1 hour, and 30.6 g of the product was obtained by suction filtration, with a mass yie...

Embodiment 2

[0029] Mix 30 g of 16,17α-epoxy-pregna-20-carboxylate methyl hydrazinoacetyl-1,4-diene-3,11-dione (a) with 150 mL of chloroform and 30 mL of pyridine , put into the pressure reactor, feed ammonia gas under stirring until the pressure of the reactor reaches 0.15 MPa (control the reaction temperature at 10-15 °C during the ventilation process), keep the reaction at 15 °C, and track the reaction progress by TLC. After the reaction is complete, transfer the material liquid to a glass reaction bottle, and when the temperature of the material drops below 10°C, add acetic acid to adjust the pH to 5-6, and remove the solvent under reduced pressure; add 30 mL of acetic acid and 30 g of acetic anhydride to the reaction bottle, and react The temperature was controlled at 30 ° C, and the reaction was carried out for 6 hours. The reaction solution was poured into cold 500 mL10% sodium hydroxide solution, stirred for 1 hour, and 28.6 g of the product was obtained by suction filtration, with ...

Embodiment 3

[0031] Mix 30 g of 16,17α-epoxy-pregna-20-carboxylate methyl hydrazinoacetyl-1,4-diene-3,11-dione (a) with 150 mL of chloroform and 30 mL of DMF, Add to a pressure reactor, feed ammonia gas under stirring until the pressure of the reactor reaches 0.15 MPa (control the reaction temperature at 10-15 °C during the ventilation process), keep the reaction at 40 °C, and track the reaction progress by TLC. After the reaction is complete, transfer the material liquid to a glass reaction bottle, and when the temperature of the material drops below 10°C, add acetic acid to adjust the pH to 5-6, and remove the solvent under reduced pressure; add 30 mL of acetic acid and 30 g of acetic anhydride to the reaction bottle, and react The temperature was controlled at 30 ° C, and the reaction was carried out for 6 hours. The reaction solution was poured into cold 500 mL10% sodium hydroxide solution, stirred for 1 hour, and 31.2 g of the product was obtained by suction filtration, with a mass yie...

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Abstract

The invention discloses a preparation method for a denazacort key intermediate [17alpha, 16alpha-d] methyl oxazoline steroids. The steps include: dissolving [16, 17alpha-epoxy-pregnane-20-methyl formate hydrazine acetyl-1,4-diene-3,11-diketone] in trichloromethane, adding [16, 17alpha-epoxy-pregnane-20-methyl formate hydrazine acetyl-1,4-diene-3,11-diketone] and additives into a pressure reaction kettle, leading ammonia to the reaction kettle to a certain pressure under the condition of stirring, and reacting at certain temperature; and dissolving the obtained compound crude products in glacial acetic acid, adding a certain amount of anhydride under the condition of stirring, and controlling reaction temperature. After the reaction, reaction liquid is poured into 500mL of cold 10% sodium hydroxide solution and stirred for 1 hours, and the denazacort key intermediate [17alpha, 16alpha-d] methyl oxazoline steroids is obtained after suction filtration. The method achieves safe and clean production of denazacort, is favorable for reducing environment pollution, shortens a production period, reduces production cost for enterprises, improves production safety, and is remarkable in social benefit, environment benefit and economical benefit.

Description

technical field [0001] The invention relates to a preparation method of a steroid compound, in particular to a preparation method of a key intermediate of deflazacort [17α, 16α-d]methyloxazoline steroid compound. Background technique [0002] Type Deflazacort chemical name here [1,4-pregnadiene-21-acetoxy-11β-hydroxy-[17,16-D]methoxazole-3,20dione ], is the third generation of glucocorticoid steroidal anti-inflammatory drugs, with anti-inflammatory, anti-allergic, increased gluconeogenesis and other effects, mainly used for the treatment of adrenal hypofunction, autoimmune diseases, rheumatoid arthritis, sarcoidosis etc. Since it has the advantages of few side effects, strong efficacy and wide indications, the drug has achieved great success since it was launched in Italy in 1985, and its sales volume has been increasing year by year. Its structural formula is shown in (A). [0003] At present, domestic and foreign literature reports mainly use mold dehydrogenate [16,17α-...

Claims

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Application Information

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IPC IPC(8): C07J71/00
Inventor 张峥斌王锦凯尹金玉朱敦明赵晓宝叶海燕
Owner JIANGXI JUNYE BIOLOGICAL PHARM CO LTD
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