Novel steroid compound, and preparation method and application thereof

A technology of steroidal compounds and compounds, applied in the direction of steroidal compounds and organic chemistry, can solve the problems of high total cost and low yield of addition reaction, and achieve the effects of reduced production cost, easy availability of raw materials, and mild reaction conditions

Active Publication Date: 2012-05-30
CHINA RESOURCES ZIZHU PHARMA
View PDF4 Cites 14 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route is all lower in the 6th step epoxidation reaction an

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Novel steroid compound, and preparation method and application thereof
  • Novel steroid compound, and preparation method and application thereof
  • Novel steroid compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: 3-(ethylenedioxy)-17α-ethynyl-17β-hydroxy-estro-5(10),9(11)-diene (compound 2)

[0030] Under the protection of nitrogen, add 1.2 L of tetrahydrofuran and 400 g of potassium hydroxide into the dry reaction flask, then lower the temperature to below 5° C., and pass through acetylene gas. Add 1L of acetone, raise the temperature to 35°C-40°C, keep flowing acetylene gas, and stir for 2 hours. 100 g of compound 1 was dissolved in 1 L of tetrahydrofuran, and added dropwise to the reaction solution. After the dropwise addition, the reaction was controlled at 35° C. to 40° C. for 1 hour. After the reaction was completed, 750 ml of saturated ammonium chloride solution was added and the reaction mixture was stirred for 10 min. The organic layer was separated, and the aqueous layer was extracted with 300 ml of tetrahydrofuran. The combined organic layers were washed with 750 ml of saturated ammonium chloride, concentrated to 600 ml under reduced pressure, poured into...

Embodiment 2

[0032] Example 2: 3-(ethylenedioxy)-17α-ethynyl-17β-hydroxy-5α,10α-epoxy-estro-9(11)-ene (compound 3)

[0033] Add 735ml of dichloromethane, 105g of compound 2 and 21g of disodium hydrogen phosphate into the reaction bottle, after cooling to 0-5°C, add 45ml of hexafluoroacetone and 95ml of 30% hydrogen peroxide, and keep stirring for 16 hours. Then, 590 ml of an aqueous solution of 10% sodium thiosulfate was added, and stirred for 30 minutes. The organic layer was separated, the aqueous layer was extracted with dichloromethane, the organic layers were combined, washed with saturated sodium bicarbonate solution and water successively, dried with anhydrous sodium sulfate and concentrated to dryness under reduced pressure to obtain compound 3. The resulting product was used directly in the next step without purification.

Embodiment 3

[0034] Example 3: 3-(ethylenedioxy)-11β-[4-(N,N-dimethyl-amino)-phenyl]-17α-ethynyl-17β,5α-dihydroxy-estro- 9(11)-ene (Compound 4)

[0035] Under nitrogen protection, 210ml of tetrahydrofuran, 23.8g of magnesium chips, 0.3 iodine and 10mL of 4-bromo-N,N-dimethylaniline in tetrahydrofuran (180g of 4-bromo-N,N-dimethyl Aniline is dissolved in 900mL THF); the temperature is raised to reflux to initiate the reaction, the temperature is lowered to 40°C to 50°C, and the remaining 4-bromo-N,N-dimethylaniline tetrahydrofuran solution is added dropwise at this temperature, and the temperature is kept at 40°C React at ~50°C for 2 hours to obtain 4-bromo-N,N-dimethylaniline Grignard reagent. Cool down to 20°C to 30°C, add 5g cuprous chloride, keep the temperature, slowly add 3-ketal tetrahydrofuran solution (the above compound 3 is dissolved in 500mL tetrahydrofuran), after the dropwise addition, continue to cool at 20°C to 30°C. ℃ reaction 2h. After the reaction was completed, 600 ml...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to a steroid compound, and a preparation method and application of the compound. The traditional method for preparing 17alpha-acetoxyl-11beta-(4-N,N-dimethylaminophenyl)19- norpregna -4,9-diene-3,20-diketone has the problems of low yield, incapability of industrial production and the like. The invention provides a novel steroid compound, and the preparation method and the application thereof. The steroid compound can be used for preparing 17alpha-acetoxyl-11beta-[4-(N,N-dimethylamino)-phenyl]-19- norpregna -4,9-diene-3,20-diketone. The preparation method is high in yield, mild in reaction condition, simple and easy to obtain raw materials and easy for industrial production.

Description

technical field [0001] The present invention relates to a steroid compound, a preparation method and use of the compound. Background technique [0002] 17α-Acetoxy-11β-[4-(N,N-Dimethylamino)-phenyl]-19-norpregna-4,9-diene-3,20-dione is an anti- Steroids with progestogenic and anticorticoid activity, used in the treatment of gynecological diseases, contraception, treatment of Cushing's syndrome and glaucoma, etc. [0003] 17α-acetoxy-11β-[4-(N,N-dimethylamino)-phenyl]-19-norpregna-4,9-diene-3,20-dione disclosed in literature The preparation methods are: [0004] U.S. Patent US5929262, using 3-(ethylenedioxy)-17α-hydroxyl-17β-cyano-estradiol-5(10), 9(11)-diene as raw material to obtain 17α-acetyl through 7-step reaction Oxy-11β-[4-(N,N-dimethylamino)-phenyl]-19-norpregna-4,9-diene-3,20-dione, the total yield is 13% . The detailed steps are as follows: [0005] [0006] The raw material 3-(ethylenedioxy)-17α-hydroxyl-17β-cyano-estra-5(10),9(11)-diene used in this route...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07J41/00
Inventor 王海田卫学史学松
Owner CHINA RESOURCES ZIZHU PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap