Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing 17α-hydroxyprogesterone or its analogues

A technology for hydroxyprogesterone and analogs, which is applied in the field of preparing 17α-hydroxyprogesterone or its analogs, can solve problems such as restricted use, and achieve the effects of improving reaction yield, reducing production cost, and high reaction yield

Active Publication Date: 2011-12-07
湖南成大生物科技有限公司
View PDF2 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Wherein compound (5) is the product of configuration inversion during the addition process, the problem of this key step in summary limits its use in industrialized production

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
  • Method for preparing 17α-hydroxyprogesterone or its analogues
  • Method for preparing 17α-hydroxyprogesterone or its analogues
  • Method for preparing 17α-hydroxyprogesterone or its analogues

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of 11α, 17α-dihydroxy-16β-methylpregna-4-diene-3,20-dione (1):

[0034] Add compound (4) (19.28g; Fw: 385.54; 50mmol), magnesium chips (1.34g; Fw: 24.30; 55mmol) successively in a dry 250mL three-necked flask equipped with a thermometer, reflux condenser, and magnetic stirring, without Lithium chloride water (3.18g; Fw: 42.39; 75mmol), 150 ml of tetrahydrofuran; then the temperature of the system was lowered to 10°C, and 75 mL of a 1M solution of tetrahydrofuran in methyl chloride was added dropwise to the reaction system, and the system was maintained during the dropwise addition. At about 20°C, continue to stir for 2h, and the reaction is complete. After the reaction was completed, 50 mL of 2M hydrochloric acid was added dropwise to the reaction system. After the dropwise addition, the temperature was raised to 50° C. and the reaction was continued with stirring for 2 h. After the reaction was completed, the organic phase was separated, and the aqueous ph...

Embodiment 2

[0036] Preparation of 11α, 17α-dihydroxy-16β-methylpregna-4-diene-3,20-dione (1):

[0037] Add compound (4) (19.28g; Fw: 385.54; 50mmol), magnesium chips (1.34g; Fw: 24.30; 55mmol) successively in a dry 250mL three-necked flask equipped with a thermometer, reflux condenser, and magnetic stirring, without Lithium chloride water (5.30g; Fw: 42.39; 125mmol), 150 ml of tetrahydrofuran; then the temperature of the system was lowered to -20°C, and 75 mL of a 1M solution of tetrahydrofuran in methyl chloride was slowly added dropwise to the reaction system. Necessary cooling was performed to maintain the system at about -20°C, and then the stirring was continued for 12 hours, and the reaction was completed. After the reaction was completed, 100 mL of 2M hydrochloric acid was slowly added dropwise to the reaction system. After the dropwise addition, the temperature was raised to 70° C. and the reaction was continued with stirring for 2 h. After the reaction was completed, the organic...

Embodiment 3

[0039] Preparation of 11α, 17α-dihydroxy-16β-methylpregna-4-diene-3,20-dione (1):

[0040] Add compound (4) (19.28g; Fw: 385.54; 50mmol), magnesium chips (1.34g; Fw: 24.30; 55mmol) successively in a dry 250mL three-necked flask equipped with a thermometer, reflux condenser, and magnetic stirring, without Lithium bromide in water (10.86g; Fw: 86.85; 125mmol), 150 ml of tetrahydrofuran; then lower the temperature of the system to -20°C, and slowly add 75 mL of 1M solution of methyl bromide in tetrahydrofuran to the reaction system dropwise, and necessary cooling is required during the dropwise addition , keep the system at about -20°C, then continue to stir for 12h, and the reaction is complete. After the reaction was completed, 100 mL of 2M hydrochloric acid was slowly added dropwise to the reaction system. After the dropwise addition, the temperature was raised to 70° C. and the reaction was continued with stirring for 2 h. After the reaction was completed, the organic phase ...

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

Provided is a preparation method for 17a-hydroxyprogesterone or analogs thereof, comprising the following steps: the compound as represented in formula (4) reacts in solvent and trihalomethane in the presence of magnesium metal and lithium halide; hydrolysis is carried out using acidic substance; the target product (1) is collected from the reaction product. The present invention lowers production cost and prevents problems such as environment polluting byproducts and highly toxic, unstable reagents and intermediate products. The reaction conditions are moderate, and the purity after simple purifications can exceed 99%. The present invention is easy to implement in industry. The reaction formula is as (4), (1).

Description

[0001] The invention relates to a method for preparing 17α-hydroxyprogesterone or its analogs. Background technique [0002] 17α-Hydroxyprogesterone is a progestin that has a pronounced morphological effect on the estrogen-stimulated endometrium in vivo and is necessary for the maintenance of pregnancy. It is clinically used in the reactive diagnosis of threatened abortion, habitual abortion and other amenorrhea or the cause of amenorrhea. At the same time, 17α-hydroxyprogesterone and its analogs are important intermediates in the synthesis of other steroid drugs, and its structural formula is as follows: [0003] [0004] At present, in the existing technology, the key step is that androstenedione and its analogs (2) are added through the 17-position carbonyl to obtain the cyanohydrin product (3), and then the 3-position carbonyl is subjected to the ketal protection of propylene glycol, and then The nitrile group is added with a metal reagent, followed by hydrolysis under...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
CPCC07J7/00C07J7/0045C07J1/0011C07J1/0033C07J7/0055C07J41/0094
Inventor 刘喜荣
Owner 湖南成大生物科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com