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A kind of method of synthesizing equilenone

A technology for the synthesis of equilin and its synthesis method, which is applied in the field of synthesis of steroid drug equilin, and can solve the problems of environmental pollution, high equipment requirements, and high cost

Active Publication Date: 2022-03-04
武汉诺唯尔医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Disadvantages: This route uses 19-hydroxyandrost-4-ene-3,17-dione as the starting material. The current market price of this material A is about 11,200 yuan / Kg, and the cost is high; the final product is obtained through nine-step linear synthesis product, the steps are lengthy, and the total yield is 32%, and the three-step reactions all involve oxidation, which requires a large amount of chemical oxidants, which will inevitably cause serious waste discharge and environmental pollution; in addition, the sixth step of catalytic oxidation requires the use of precious metal palladium acetate , the cost is higher; the other temperature range is from -70 degrees to 130 degrees, which requires higher equipment
[0012] In summary, the existing equilin synthesis methods all have obvious deficiencies and need to be improved

Method used

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  • A kind of method of synthesizing equilenone
  • A kind of method of synthesizing equilenone
  • A kind of method of synthesizing equilenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1. Synthesis of intermediate I (C3 acetyl protection; C17 ethylene glycol ketal protection):

[0025] Add acetic anhydride (150mmol, 15.3g) and 4-dimethylaminopyridine (3mmol, 0.367g) successively to estrone (30mmol, 8.1g), stir at room temperature for 15 minutes, thin layer chromatography shows that estrone has been converted completely. Concentrate and add dichloromethane (20mL) to dilute, add saturated NaHCO 3 Solution to system is neutral. After liquid separation, the organic phase was washed with water, saturated brine, anhydrous Na 2 SO 4 After drying, filter through silica gel and suck dry (recover the solvent) to obtain a white solid. Dissolve the white solid in anhydrous benzene (30 mL), add ethylene glycol (60 mmol, 3.72 g) and p-toluenesulfonic acid (3 mmol, 0.516 g), heat to reflux for 5 hours, and cool to room temperature. saturated Na 2 CO 3 solution, washed with water, and then washed with saturated brine, combined the organic phases, and d...

Embodiment 2

[0027] Use tert-butyryl, benzoyl, CBZ (benzyloxycarbonyl, O=C-OCH 2 Ph), BOC (tert-butoxycarbonyl) and p-toluenesulfonyl anhydride instead of acetic anhydride, the others are the same as in Example 1, and the yields of compound I are 75%, 70%, 78%, 72%, and 76%, respectively.

Embodiment 3

[0029] Acetyl, tert-butyryl, benzoyl, CBZ (benzyloxycarbonyl, O=C-OCH 2 Ph), BOC (tert-butoxycarbonyl) and p-toluenesulfonyl chloride instead of acetic anhydride, others are the same as in Example 1, and the yield of compound I is respectively 80%, 77%, 75%, 79%, 78%, 75%.

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Abstract

The invention relates to a method for synthesizing steroid medicine equilin. This method starts from estrone, after being protected by phenolic hydroxyl group and C17 ketal, then oxidized and further dehydrogenated to obtain intermediate II; after reduction and deoxygenation, intermediate III is obtained; finally deprotected to obtain the raw material of the final product equilenone medicine. The method is economical in steps, with a total of four steps of transformation; the total yield is as high as 50%; the raw materials are relatively cheap and easy to obtain, the whole process route is green and safe, the raw material medicine is of high quality, and the purity can reach 99.8% or above, which is suitable for industrial production.

Description

technical field [0001] The invention belongs to the production process of steroid medicine, in particular to a synthesis method of steroid medicine equilin. Background technique [0002] Equilin, aliased as (horse) estrotetraenolone, equilin, 6,9-dihydro equilin (steroid) ketone; English name Equilin, 1,3,5,7- estratetraen-3-ol-17-one; Estra-1,3,5(10),7-tetraen-17-one,3-hydroxy-; (9S,13S,14S)-3-hydroxy-13-methyl- 9,11,12,14,15,16-h exahydro-6H-cyclopenta[a]phenanthren-17-one; 1,3,5,7-Estratetraen-3-ol-17-one; 7-Dehydroestrone; 1 ,3,5(10),7-Estratetraen-3-ol-17-one; 3-Hydroxy-1,3,5(10),7-estratetraen-17-one; CAS No. 474-86-2. It is a major component of conjugated estrogens. The drug that went on the market in 1941—the trade name of Conjugated estrogens (Conjugated estrogens) is Pfizer's "Premarin". This drug has been on the market for many years and has been the drug of choice for estrogen replacement therapy (HRT). It is used to supplement estrogen in postmenopausal wome...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J1/00
CPCC07J1/0059Y02P20/55
Inventor 郑婷芬
Owner 武汉诺唯尔医药科技有限公司
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