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Steroid compound, preparation method and uses thereof

A steroid compound and a technology for the compound are applied to the steroid compound and the fields of preparation and use thereof, and can solve the problems of low yield of gestodene, difficult removal of ketal protecting group, unfavorable industrial production and the like, and achieve a simple process. Ease of operation and high yield

Active Publication Date: 2013-09-25
CHINA RESOURCES ZIZHU PHARMA
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  • Abstract
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Problems solved by technology

[0006] The disadvantages of the above-mentioned preparation method are mainly: 16-benzenesulfinyl ketal (VII) is an oily mixture, which can only be separated by column chromatography, which is not conducive to industrial production; The yield of Gestodene is low when deprotected under the conditions

Method used

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  • Steroid compound, preparation method and uses thereof
  • Steroid compound, preparation method and uses thereof
  • Steroid compound, preparation method and uses thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Embodiment 1: the preparation of compound II

[0029] 10g (34.92mmol) of compound I and 10mL of absolute ethanol were stirred at room temperature (17°C), 10ml of triethyl orthoformate and 0.2g of p-toluenesulfonic acid were added, and the reaction was stopped after stirring for 1 hour. Column chromatography separation was carried out with ethyl acetate / petroleum ether (2:8), and the weight of the obtained product (compound II) was 7.28 g, and the molar yield was 80.0%.

Embodiment 2

[0030] Embodiment 2: the preparation of compound III

[0031] Compound II 7g (22.26mmol) was mixed with 100mL of tetrahydrofuran, 8.51g of potassium tert-butoxide was added at room temperature (15°C), 10mL of methyl phenylsulfite was added under stirring, and the reaction was stopped after stirring for 2 hours. Water analysis gave a yellow solid (compound III), which weighed 7.32 g after drying, and the molar yield was 69.5%.

[0032] MS (m / z) of compound III: 438[M]+, 1H-NMR (CDCl3), δ0.92 (3H, t, 18-CH3), δ1.32 (3H, t, 3-CH3), δ3 .87 (2H, q, 3-CH2-O), δ4.89 (1H, dt, H-6), δ4.92 (1H, d, H-4), δ7.41-7.58 (5H, m, 16-Ph); 13C-NMR, 209.7(C-17), 155.2(C-3), 135.9(C-5), 123.4(C-6), 102.1(C-4), 73.7(C-16) , 62.3 (3-CH2-O).

Embodiment 3

[0033] Embodiment 3: the preparation of compound III

[0034] 7g (22.26mmol) of compound II was mixed with 100mL of dichloromethane, 3.50g of potassium hydroxide was added at room temperature (20°C), 10mL of methyl phenylsulfite was added under stirring, and the reaction was stopped after stirring for 2 hours. Water analysis gave a yellow solid (compound III), which weighed 6.88 g after drying, and the molar yield was 65.3%.

[0035] MS (m / z) of compound III: 438[M] + , 1H-NMR (CDCl 3 ), δ0.92 (3H, t, 18-CH 3 ), δ1.32 (3H, t, 3-CH 3 ), δ3.87 (2H, q, 3-CH 2 -O), δ4.89(1H, dt, H-6), δ4.92(1H, d, H-4), δ7.41-7.58(5H, m, 16-Ph); 13C-NMR, 209.7 (C-17), 155.2(C-3), 135.9(C-5), 123.4(C-6), 102.1(C-4), 73.7(C-16), 62.3(3-CH 2 -O).

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Abstract

The present invention provides a gestodene intermediate and a preparation method thereof, and further provides a new process route for preparing gestodene. According to the present invention, phenylsulfinyl is introduced to the site 16 of a steroid etherate to obtain an easily-separated new compound, wherein characteristics of simple operation and high yield are provided when the compound is used for preparing gestodene.

Description

technical field [0001] The present invention relates to steroidal compounds and their application in the process of preparing Gestodene. Background technique [0002] Gestodene is currently an ideal third-generation contraceptive, with a strong progesterone effect and no androgen and estrogen activity. The drug has reliable effect and good safety when used for contraception, and its compound tablet with ethinyl estradiol is commonly used as a short-acting oral contraceptive in clinical practice. [0003] Patent EP1586579 discloses a synthesis method of Gestodene, which uses ethyl diketone compound (I) as the starting material, ketal protection of the 3-position carbonyl, and then replaces the 16-position active hydrogen to eliminate the substitution Form the 15 (16) double bond, and then go through the ethynylation of the 17 carbonyl group, and finally deprotect the 3 positions to obtain Gestodene (V). The reaction process is shown in Scheme 1: [0004] [route 1] [0005]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
Inventor 蒋彬张冲王保江许丹
Owner CHINA RESOURCES ZIZHU PHARMA
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