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Method for synthesizing equilin

A technology for equine estrone and a synthesis method, which is applied in the field of synthesizing steroid drug equine estrone, can solve problems such as a large number of chemical oxidants, three waste discharges, environmental pollution and the like

Active Publication Date: 2021-05-25
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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  • Method for synthesizing equilin
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  • Method for synthesizing equilin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1. Synthesis of Intermediate I (Acetyl protection at C3; ethylene glycol ketal protection at C17):

[0025] Acetic anhydride (150mmol, 15.3g) and 4-dimethylaminopyridine (3mmol, 0.367g) were successively added to estrone (30mmol, 8.1g), and the mixture was stirred at room temperature for 15 minutes. Thin layer chromatography showed that the raw material estrone had been converted. completely. After concentration, dichloromethane (20 mL) was added to dilute, and saturated NaHCO was added. 3 The solution to the system is neutral. After separation, the organic phase was washed with water, saturated brine, and anhydrous Na 2 SO 4 After drying, silica gel filtration and suction to dryness (solvent recovery) to obtain a white solid. The white solid was dissolved in anhydrous benzene (30 mL), then ethylene glycol (60 mmol, 3.72 g) and p-toluenesulfonic acid (3 mmol, 0.516 g) were added, heated to reflux for 5 hours, and cooled to room temperature. Saturated Na 2 ...

Embodiment 2

[0027] tert-butyryl, benzoyl, CBZ (benzyloxycarbonyl, O=C-OCH) 2 Ph), BOC (tert-butoxycarbonyl) and p-toluenesulfonyl anhydride instead of acetic anhydride, 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] Respectively with acetyl, tert-butyryl, benzoyl, CBZ (benzyloxycarbonyl, O=C-OCH 2 Ph), BOC (tert-butoxycarbonyl) and p-toluenesulfonyl chloride instead of acetic anhydride, other are the same as in Example 1, the yields of compound I are 80%, 77%, 75%, 79%, 78%, respectively, 75%.

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Abstract

The invention relates to a synthesis method of a steroid drug, namely equilin. The method comprises the following steps: starting from estrone, performing phenolic hydroxyl group and C17-position ketal protection, and then performing oxidation and further dehydrogenation to obtain an intermediate II; reducing and deoxidizing the intermediate II to obtain an intermediate III; and finally, performing deprotection to obtain a final product, namely an equilin bulk drug. The method is few in steps and comprises four conversion steps; total yield is as high as 50%; the used raw materials are relatively cheap and easy to obtain; the whole process route is green and safe; and the bulk drug is high in quality, has purity of 99.8% or above, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the production process of steroid medicine, in particular to a method for synthesizing steroid medicine equine estrone. Background technique [0002] Equilin, equilin, 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 estrogen. The drug marketed in 1941, the trade name of Conjugated estrogens (Conjugated estrogens) is Pfizer's "Premarin", which has been the drug of choice for Hormone replacement therapy (HRT) for many years. Estrogen supplementation for postmenopausal women to relieve their menopausal symptoms. Conjugated estrogens are mixtures of steroid hormones (sulfates of estrogens) extracted from ...

Claims

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Application Information

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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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