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The preparation method of prednisolone intermediate or its analog

A technology for prednisolone and intermediates, which is applied in the field of preparation of steroid drug intermediates, can solve the problem of high cost of starting materials, and achieve the effects of stable yield, high yield and high yield.

Active Publication Date: 2016-01-27
HUNAN NORCHEM PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is the high cost of starting materials

Method used

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  • The preparation method of prednisolone intermediate or its analog
  • The preparation method of prednisolone intermediate or its analog

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Elimination reaction

[0020] At room temperature, under the protection of nitrogen, add 400ml of anhydrous tetrahydrofuran to a clean and dry 500ml four-neck round-bottomed flask equipped with a thermometer, reflux condenser, and mechanical stirring, and add 80.0g of compound Ⅰ under stirring, and cool the system to 0 to 10°C , add 80.0 g of phosphorus pentachloride in batches at 0 to 10°C under temperature control, and keep warm at 0 to 10°C after the addition is complete. TLC followed the reaction until no raw material remained. The reaction system was added dropwise to 1 L of ice water, a large amount of solids were precipitated, and the stirring was continued for 2 hours. The system was suction-filtered, the filter cake was washed with water until it was neutral, and dried at 50°C to obtain 70.8 g of compound II with a yield of 88.5%. 96.8%.

[0021] Cyano substitution reaction

[0022] At room temperature, under the protection of nitrogen, add 100ml of methano...

Embodiment 2

[0029] Elimination reaction

[0030]At room temperature, under the protection of nitrogen, add 450ml of anhydrous tetrahydrofuran to a clean and dry 500ml four-necked round-bottomed flask equipped with a thermometer, reflux condenser, and mechanical stirring, and add 80.0g of compound Ⅰ under stirring, and cool the system to 0 to 10°C , add 80.0 g of p-toluenesulfonyl chloride in batches under temperature control at 0-10°C, and keep warm at 0-10°C after the addition is complete. TLC followed the reaction until no raw material remained. The reaction system was added dropwise to 1 L of ice water, a large amount of solids were precipitated, and the stirring was continued for 2 hours. The system was suction-filtered, the filter cake was washed with water until it was neutral, and dried at 50°C to obtain 69.2 g of compound II with a yield of 86.5%. 96.5%.

[0031] Cyano substitution reaction

[0032] At room temperature, under the protection of nitrogen, add 90ml of methanol, 3...

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Abstract

The invention relates to a preparation method for a prednisolone intermediate or its analogue. The prednisolone intermediate or its analogue is prepared from a compound I by means of elimination reaction, cyanogroup substitution reaction, siloxy protective reaction, intramolecular nucleophilic substitution reaction and esterification reaction. The method provided by the invention has the advantages of cheap raw materials, high and stable yield. The reaction route is shown as the following, wherein R1 is Cl or Br, and R can be H or hydrocarbonyl of C1-C10.

Description

technical field [0001] The present invention relates to the preparation method of steroid drug intermediate, in particular to a kind of preparation method of prednisolone intermediate or its analogue. Background technique [0002] Prednisolone is mainly used for various acute severe bacterial infections, severe allergic diseases, collagen diseases (lupus erythematosus, nodular periarteritis, etc.), rheumatism, rheumatoid arthritis, nephrotic syndrome, severe bronchial Asthma, acute lymphoblastic leukemia, various adrenal insufficiency, etc. More potent than hydrocortisone. [0003] my country's steroid drug and its intermediate industry has reached a certain scale, and it has become the largest exporter of hydrocortisone and prednisolone in the world. At present, the synthesis of prednisolone or its analogues is mainly a preparation method combining biological fermentation and chemical synthesis, which has the problems of low yield and high cost. [0004] The difficulty i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J5/00
Inventor 刘喜荣
Owner HUNAN NORCHEM PHARMACEUTICAL CO LTD
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