Preparation method of 1,4,9(11)-triene-androst-3,17-dione

A technology of triene androster and dione, which is applied in the field of preparation of 1,4,9(11)-triene androst-3,17-dione, can solve the problem of high production cost and the price of starting materials High, low production yield and other problems, to achieve the effect of avoiding ultra-low temperature reaction, less side reactions, and less equipment investment

Inactive Publication Date: 2015-02-04
江西赣亮医药原料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The starting material price of this method is relatively high, and the conversion rate is low

Method used

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  • Preparation method of 1,4,9(11)-triene-androst-3,17-dione
  • Preparation method of 1,4,9(11)-triene-androst-3,17-dione
  • Preparation method of 1,4,9(11)-triene-androst-3,17-dione

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Put 500ml of chloroform, 100g of 9ɑ-OH-4AD (compound I), and 10g of ferric chloride into the three-necked reaction flask, stir and heat up to reflux, keep the temperature for 5-6h, after the reaction is complete, cool down to about 25°C, add water dropwise 200ml to terminate the reaction, concentrated under reduced pressure to gradually dryness, added 1000ml of water, stirred for 30min, filtered and washed with water until neutral, dried to obtain 90g of compound 4,9(11)-diene androst-3,17-dione (compound II) ; Weight yield: 90%, HPLC content: 99%.

[0028] According to the formula: yeast extract 4g / L, peptone 4g / L, magnesium sulfate heptahydrate 0.5g / L, disodium hydrogen phosphate 4g / L, potassium dihydrogen phosphate 2g / L, glucose 10g / L, agar powder 20g / L, Prepare the slant seed medium, fully dissolve various raw materials according to the ratio during preparation, stir evenly, use 20% NaOH solution to adjust the pH value to 7.2, then raise the temperature to 121°C-122...

Embodiment 2

[0036] Put 700ml of dichloromethane, 100g of 9ɑ-OH-4AD (compound I), and 5g of antimony pentachloride into the three-necked reaction flask, stir and heat up to reflux, keep warm for 15-16h, after the reaction is complete, cool down to about 10°C, add water dropwise 200ml to terminate the reaction, concentrated under reduced pressure to gradually dryness, added 1000ml of water, stirred for 30min, filtered and washed with water until neutral, dried to obtain 89g of compound 4,9(11)-diene androst-3,17-dione (compound II) ; Weight yield: 89%, HPLC content: 99%.

[0037] According to the formula: yeast extract 4g / L, peptone 4g / L, magnesium sulfate heptahydrate 0.5g / L, disodium hydrogen phosphate 4g / L, potassium dihydrogen phosphate 2g / L, glucose 10g / L, agar powder 20g / L, Prepare the slant seed medium, fully dissolve various raw materials according to the ratio during preparation, stir evenly, use 20% NaOH solution to adjust the pH value to 7.2, then raise the temperature to 121°C-1...

Embodiment 3

[0045] Put 100ml of toluene, 100ml of glacial acetic acid, 100g of 9ɑ-OH-4AD (compound I) into the three-necked reaction flask, cool down to about 10°C, add 50ml of 70wt% sulfuric acid dropwise, after the dropwise addition, react at a constant temperature of 10°C for 20h, and add 400ml of water dropwise Terminate the reaction, concentrate toluene under reduced pressure, add 1000ml of water, stir for 30min, filter and wash with water until neutral, and dry to obtain 87g of compound 4,9(11)-diene androst-3,17-dione (compound II); weight Yield: 87%, HPLC content: 97%.

[0046] According to the formula: yeast extract 4g / L, peptone 4g / L, magnesium sulfate heptahydrate 0.5g / L, disodium hydrogen phosphate 4g / L, potassium dihydrogen phosphate 2g / L, glucose 10g / L, agar powder 20g / L, Prepare the slant seed medium, fully dissolve various raw materials according to the ratio during preparation, stir evenly, use 20% NaOH solution to adjust the pH value to 7.2, then raise the temperature to...

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Abstract

The invention discloses a preparation method of 1,4,9(11)-triene-androst-3,17-dione, which uses a compound I 9alpha-OH-4AD as an initial raw material and comprises the following steps: A) elimination reaction: adding the compound I into an eliminating solvent to eliminate 9- alpha hydroxy group by using the eliminating reagent, and reacting to obtain a compound II; and B) fermentation conversion: preparing a fermentation culture medium by using the compound II as a raw material, inoculating a Nocard's bacillus strain into the fermentation culture medium, culturing for conversion, and extracting to obtain a compound III, namely 1,4,9(11)-triene-androst-3,17-dione. The new initial raw material adopted by the method is cheap and accessible; and the new elimination method avoids ultralow temperature reaction, is simple to operate, and has the advantages of low equipment investment, fewer side reactions and high yield.

Description

technical field [0001] The present invention relates to a production method of basic steroid drug intermediates, in particular to the production of 1,4,9(11)-triene androst-3,17-dione by combining chemical synthesis and microbial fermentation method. Background technique [0002] Steroidal drugs have anti-inflammatory, contraceptive, diuretic, anti-drug, anti-allergic, and antibody-suppressing effects, and are widely used in eczema, asthma, and rheumatic diseases. In recent years, the scope of application of steroidal drugs in the medical field has continued to expand, and they are widely used in the treatment of rheumatism, cardiovascular disease, collagenous diseases, lymphatic leukemia, human organ transplantation, anti-tumor, bacterial encephalitis, skin diseases, endocrine disorders, Senile diseases, etc., steroids also have a certain effect on certain cancers, especially hormone-dependent tumors. Steroid drugs have a wide range of actions and high yields, and are the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P33/00C12R1/365
Inventor 蒋青锋应正平陈小良杨坤欧阳松
Owner 江西赣亮医药原料有限公司
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