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Preparation method of prednisone acetate

A technology of prednisone acetate and its products, which is applied in the field of preparation of steroid drugs, can solve the problems of affecting the purity and quality of the product, not conforming to atom economy, and difficult to complete conversion, etc., and achieves low cost, high yield, and high selection sexual effect

Inactive Publication Date: 2015-02-25
ZHEJIANG XIANJU PHARMA
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Problems solved by technology

This traditional process route is long, the yield is low, and because the biofermentation dehydrogenation of cortisone acetate is difficult to completely convert, and the properties are close to prednisone acetate, it is difficult to remove during refining, which affects the purity and quality of the product
[0006] Chinese invention patent document CN101117350A discloses a new synthetic route of iodolation and then ring opening, which improves the selectivity of the final product of prednisone acetate, reduces the impurity content of the product, and makes it comply with glucocorticoid drugs Chromaticity standard, but its route requires epoxy ring opening and Raney nickel debromination, high cost, low yield, not in line with atom economy

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preparation example Construction

[0029] The preparation method of prednisone acetate of the present invention may further comprise the steps:

[0030] The first step, iodination reaction:

[0031] Process 1.1, preparation of iodine solution: anhydrous CaCl 2 Dissolve in methanol, avoid light, add iodine, and set aside;

[0032] Among them, iodine and CaCl 2 The mass ratio is 1:0.1~1:0.4, anhydrous CaCl 2 The molar concentration of the methanol solution is between 0.24 and 3.6 mol / L;

[0033] Step 1.2, adding anhydrous CaCl to the reaction bottle 2 and methanol, stir to dissolve, add solvent, dihydroxyprogesterone dehydrogenate 1, cool down to 0-10°C, add CaO, keep away from light, drop in iodine solution at -5-10°C, add dropwise for 2-4 hours After the dropwise addition, the reaction was continued at -5-10°C for 4-6 hours, and the reaction was stopped when there was no raw material point detected by TLC; the reaction was quenched by adding 5-30% ammonium chloride or 5-30% acetic acid aqueous solution, an...

Embodiment 1

[0058] The first step, iodination reaction:

[0059] Process 1.1. Preparation of iodine solution: add CaCl to a 500mL one-mouth bottle 2 22g and 220mL of methanol, stirred to dissolve, protected from light, added 95g of iodine, stirred for later use;

[0060] Step 1.2, add anhydrous CaCl to the 2000mL four-necked reaction flask 2 10g, 100mL of methanol, stir to dissolve, add 100g of dihydroxyprogesterone dehydrogenate, 500mL of chloroform, cool down to 0-10°C, add 65g of CaO, keep away from light, cool down to -5-0°C, add iodine solution dropwise, After 2 to 3 hours of dropping, continue to react at -5 to 0°C for 4 to 5 hours after the dropping, stop the reaction when there is no raw material point detected by TLC; drop 5 to 30% ammonium chloride aqueous solution to quench the reaction, and decompress Concentrate, pour into ice water and stir for 1 hour, suction filter to dryness, and vacuum-dry at 25°C to obtain the above iodine products 2a and 2b, with a molar yield of 9...

Embodiment 2

[0067] The first step, iodine reaction;

[0068] Process 1.1. Preparation of iodine solution: add CaCl to a 200mL one-mouth bottle 2 8g and 300mL of methanol, stir to dissolve, avoid light, add 80g of iodine, stir for later use;

[0069] Step 1.2, add anhydrous CaCl to the 2000mL four-necked reaction flask 2 5.5g, 55mL of methanol, stir to dissolve, add 100g of dihydroxyprogesterone dehydrogenate, 165mL of dichloromethane, cool down to 0-10°C, add 50g of CaO, keep away from light, drop the iodine solution at 0-10°C, After 2-3 hours of dropping, continue the reaction at 0-10°C for 5-6 hours after the dropping, stop the reaction when there is no raw material point detected by TLC, drop 5-30% acetic acid aqueous solution to quench the reaction, concentrate under reduced pressure, pour Stir in ice water for 1 hour, suction filter to dryness, and vacuum-dry at 25°C to obtain the above iodine products 2a and 2b, with a molar yield of 95% and an HPLC content of 96%.

[0070] The...

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Abstract

The invention discloses a preparation method of prednisone acetate, which comprises the following steps: by using dihydroxy progesterone dehydrogenate as a raw material, carrying out iodination reaction to obtain an iodination product, carrying out replacement reaction to obtain a substitution product, and finally, carrying out oxidation reaction to obtain the prednisone acetate. The dihydroxy progesterone dehydrogenate, which is used as the raw material for the first time, is sequentially subjected to iodination, replacement and oxidation reaction to obtain the high-purity prednisone acetate. The method has the advantages of short technical route, high product quality, high yield and low cost, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a preparation method of steroid medicine, in particular to a preparation method of prednisone acetate. Background technique [0002] Prednisone acetate is a very important class of corticosteroids. It acts on glucose metabolism and reduces the pathological response of body tissues to damaging stimuli. It is mainly used for various acute severe bacterial infections and various adrenal insufficiency Wait. [0003] The structural formula of prednisone acetate is: [0004] [0005] To prepare prednisone acetate, the traditional process is to obtain by biofermentation of cortisone acetate. Edited by Ye Songlin, Wu Yingzheng, etc., the "National Compendium of Raw Materials Processes" (1980) published by the State Administration of Medicine included this synthetic process. The synthesis process method is as follows: acetic acid pregnant dienolone is synthesized into cortisone acetate through 8-step reaction, and the cortisone ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J5/00
CPCC07J5/0053
Inventor 戴静陈德家袁云方伟明
Owner ZHEJIANG XIANJU PHARMA
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