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Preparation method of gestodene impurity F

A gestodene and impurity technology is applied in the field of pharmaceutical synthesis to achieve the effects of high product purity, good environmental protection effect and reasonable process design

Inactive Publication Date: 2020-07-03
TLC NANJING PHARMA RANDD CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The preparation method of Gestodene impurity F provided by the present invention has not been reported yet

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  • Preparation method of gestodene impurity F
  • Preparation method of gestodene impurity F
  • Preparation method of gestodene impurity F

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Effect test

Embodiment 1

[0040] A preparation method of Gestodene impurity F, specifically comprising the following steps:

[0041] Preparation of Compound II: Dissolve 13beta-ethyl-15alfa-hydroxystan-4-ene-3,17-dione (Compound I) (20.00g, 0.06mol) in tetrahydrofuran, add pyridine (8.37g, 0.11 mol), tert-butyldimethylsilyl chloride (12.46g, 0.08mol), stirred at 35°C for 5 hours, added 110mL of water to the reaction solution, added 120mL of ethyl acetate, separated, and dried the organic phase, Using petroleum ether: ethyl acetate with a volume ratio of 2:1 as the eluent, 25.89 g of white solid compound II was obtained by column chromatography with a yield of 93.95%.

[0042] Preparation of Compound III: Dissolve Compound II (21.18g, 0.05mol) in N,N-dimethylformamide, add neopentyl glycol (9.53g, 0.09mol), boron trifluoride diethyl ether (1.08g, 0.008mol), stirred at 33°C for 17 hours, under ice bath conditions, added 100mL saturated sodium bicarbonate solution to the reaction solution, added 100mL et...

Embodiment 2

[0047] A preparation method of Gestodene impurity F, specifically comprising the following steps:

[0048] Preparation of Compound II: Dissolve 13beta-ethyl-15alfa-hydroxystan-4-ene-3,17-dione (Compound I) (50.00g, 0.16mol) in tetrahydrofuran, add pyridine (20.93g, 0.26 mol), tert-butyldimethylsilyl chloride (31.15g, 0.21mol), stirred at 10°C for 2 hours, added 250mL of water to the reaction solution, added 200mL of ethyl acetate, separated the layers, dried the organic phase, and used Petroleum ether:ethyl acetate at a volume ratio of 2:1 was used as the eluent, and 46.43 g of white solid compound II was obtained by column chromatography, with a yield of 67.39%.

[0049] Preparation of Compound III: Dissolve Compound II (42.15g, 0.10mol) in N,N-dimethylformamide, add neopentyl glycol (10.54g, 0.10mol), boron trifluoride diethyl ether (0.72g, 0.005mol), stirred at 5°C for 1 hour, under ice bath conditions, added 200mL saturated sodium bicarbonate solution to the reaction solu...

Embodiment 3

[0054] A preparation method of Gestodene impurity F, specifically comprising the following steps:

[0055] Preparation of Compound II: Dissolve 13beta-ethyl-15alfa-hydroxystan-4-ene-3,17-dione (Compound I) (50.00g, 0.16mol) in tetrahydrofuran, add pyridine (20.93g, 0.26 mol), tert-butyldimethylsilyl chloride (31.15g, 0.21mol), stirred at 60°C for 26 hours, added 250mL of water to the reaction solution, added 200mL of ethyl acetate, separated the layers, dried the organic phase, and used Petroleum ether:ethyl acetate at a volume ratio of 2:1 was used as the eluent, and 35.43 g of white solid compound II was obtained by column chromatography, with a yield of 51.43%.

[0056] Preparation of Compound III: Dissolve Compound II (42.15g, 0.10mol) in N,N-dimethylformamide, add neopentyl glycol (47.41g, 0.45mol), boron trifluoride diethyl ether (25.84g, 0.18mol), stirred at 50°C for 24 hours, under the condition of ice bath, add 200mL saturated sodium bicarbonate solution to the react...

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Abstract

The invention discloses a preparation method of a gestodene impurity F. According to the preparation method, 13beta-ethyl-15alfa-hydroxyandrost-4-ene-3,17-dione is taken as a raw material, and preparation of the gestodene impurity F is realized through five steps of reaction. The preparation method provided by the invention has the advantages of reasonable process design, strong operability, mildreaction conditions and high yield, and can realize industrial production. The gestodene impurity F prepared by the invention provides an important basis for scientific evaluation of the quality, safety and efficiency of gestodene.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a preparation method of Gestodene impurity F. Background technique [0002] Gestodene, the chemical name is 17-ethynyl-13-ethyl-17βhydroxypregna-4,15-dien-3-one, the chemical structure is characterized by the introduction of a double bond at the l5 position in the D ring , the molecular formula is C21H26O2, the molecular weight is 310.44, and the structural formula is as follows: [0003] [0004] Gestodene was developed by Schilling Company in Germany and was first registered and marketed in the UK in 1987. By 1990, it had been clinically used in more than 30 countries around the world. [0005] Gestodene is a synthetic progestogen, a derivative of 18-methyl norethindrone, and is a highly effective progestogen contraceptive. It has been reported that gestodene has unique pharmacological effects, and it is the only hormone that has been used so far. The oral contraceptive with ...

Claims

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Application Information

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IPC IPC(8): C07J1/00
CPCC07J1/0096
Inventor 吴文超徐庶张池刘春崔希林
Owner TLC NANJING PHARMA RANDD CO LTD