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Preparation method of deprodone propionate

A technology of dipronone propionate and dipronone propionate, which is applied in the field of preparation of local anti-inflammatory hormone drug dipronone propionate, can solve the problems of low synthesis efficiency and high production cost, and achieve low production cost and high product quality. Good quality, simple process operation and environmental protection effect

Inactive Publication Date: 2018-01-09
HUNAN KEREY BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis method is viewed from the molecular structure. The 21-position hydroxyl group of prednisolone, the raw material, is replaced by iodine and potassium acetate on the 20-position methyl group, followed by three steps of alkali hydrolysis and two steps of sulfonylation and reduction. The reaction is removed, the synthesis efficiency is low, and the actual production cost is indeed high

Method used

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  • Preparation method of deprodone propionate
  • Preparation method of deprodone propionate

Examples

Experimental program
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Effect test

Embodiment 1

[0039] A. Preparation of dehydrated matter

[0040] In a 2000ml three-necked flask, add 100g of mildew and 1200ml of pyridine, stir to dissolve completely, then pass in sulfur trioxide at 30-35°C, keep the pressure at about 1.5atm, ventilate for 10 to 12 hours, confirm by TLC At the end of the reaction, after the reaction, remove sulfur trioxide in vacuum, then add 100ml of 30% caustic soda solution and 100ml of saturated saline to wash once, then concentrate under reduced pressure to recover 90-95% of pyridine, and finally add 600ml of tap water, Stir and crystallize at 10-15°C for 3-4 hours, centrifuge, wash with water to obtain the crude dehydrated product, add the above-mentioned crude product to 500ml 20% ethanol aqueous solution directly without drying, stir and crystallize at 0-5°C for 5-6 hours, centrifuge, Washed with water and dried to obtain 85 g of dehydrated product, the HPLC content was 99.2%, and the weight yield was 85%.

[0041] B. Preparation of epoxy

[00...

Embodiment 2

[0050] A. Preparation of dehydrated matter

[0051] In a 2000ml three-necked bottle, add 100g of mildew and 1200ml of chloroform, stir to dissolve completely, then add 120ml of pyridine, then pass in sulfur trioxide at 30-35°C, keep the pressure at about 1.5atm, and ventilate for 10~ After 12 hours, TLC confirmed the end point of the reaction. After the reaction, remove sulfur trioxide in vacuum, then add 100ml of 30% caustic soda solution and 100ml of saturated saline to wash once, then concentrate under reduced pressure to recover 90-95% of chloroform and pyridine , finally add 600ml of tap water, stir and crystallize at 10-15°C for 3-4 hours, centrifuge, wash with water to get the crude dehydrated product, directly add the above crude product to 500ml of 20% ethanol aqueous solution without drying, and stir at 0-5°C Crystallize for 5-6 hours, centrifuge, wash with water, and dry to obtain 84.5 g of dehydrated product, with an HPLC content of 99.3% and a weight yield of 84.5...

Embodiment 3

[0061] A. Preparation of dehydrated matter

[0062]In a 2000ml three-necked bottle, add 100g of mildew and 1200ml of toluene, stir to dissolve completely, then add 120ml of triethylamine, and then inject sulfur trioxide at 30-35°C, keep the pressure at about 1.5atm, and ventilate the reaction After 10-12 hours, TLC confirms the end point of the reaction. After the reaction, remove sulfur trioxide in vacuum, then add 100ml of 30% caustic soda solution and 100ml of saturated saline to wash once, then concentrate under reduced pressure to recover 90-95% toluene , finally add 600ml of tap water, stir and crystallize at 10-15°C for 3-4 hours, centrifuge, wash with water to get the crude dehydrated product, add the above crude product directly to 500ml of 20% ethanol aqueous solution without drying, stir and crystallize at 0-5°C After 5-6 hours, centrifuge, wash with water, and dry to obtain 84.2 g of dehydrated product with an HPLC content of 99.3% and a weight yield of 84.2%.

[...

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Abstract

The invention relates to a preparation method of deprodone propionate. The preparation method comprises the following steps: dissolving a mildew extract with a relatively price, as a raw material, into an organic solvent, adding pyridine, and introducing sulfur trioxide to dehydrate 11-site a hydroxyl, so as to obtain a dehydrated object; dissolving the dehydrated object into the organic solvent to epoxidize a 11-site double bond under the catalysis of caustic soda, so as to obtain an epoxidized object; dissolving the epoxidized object into the organic solvent to generate reaction by virtue ofa double epoxy bond with hydrobromic acid under the catalysis of acetic anhydride, so as to obtain dibromide; carrying out reduction debromination on dibromide molecules, so as to obtain deprodone; and finally carrying out propionylation on deprodone, so as to obtain deprodone propionate. The total yield by weight of the above five steps is 60-65%, and the HPLC content of the final product is 99.0% or above. The preparation method has the beneficial effects that a synthetic route is reasonable in design, the production raw materials are cheap and easily available, the process operation is simple and environmentally friendly, the total yield is high, the product quality is good, and the production cost is 20%-25% lower than a traditional method; and furthermore, the reaction solvent can berecycled and circularly used, so that the method is economic, environmentally friendly and very suitable for industrial production.

Description

technical field [0001] The invention belongs to the preparation technology of steroid hormone drugs, in particular to a method for preparing local anti-inflammatory hormone drug dipronone propionate. Background technique [0002] Dipronone propionate, molecular formula C21H28O4, chemical name 11b,17a-dihydroxy-1,4-pregnane-3,20-dione-17-propionate, is a topical anti-inflammatory steroid Glucocorticoid drugs are clinically mainly used for the treatment of various neurological and allergic dermatitis and various skin ringworm and other diseases, with small side effects, good effect and broad market prospects. The traditional production method of dipronone propionate is to use prednisolone as raw material, through 21 sulfonyl chloride esterification, 11 nitrate acetyl esterification, 21 reductive deesterification, 17 propionylation, 11 zinc powder , acetic acid reduction and deprotection and other five-step reactions to prepare dipronone propionate. The process route is attac...

Claims

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Application Information

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IPC IPC(8): C07J7/00
Inventor 甘红星胡爱国左前进吴来喜
Owner HUNAN KEREY BIOTECH
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