Supercharge Your Innovation With Domain-Expert AI Agents!

Selective oxidation method for hexa(hepta)decene-pregna-11-alpha-hydroxy

A technology of pregnan and diene, which is applied in the field of selective oxidation of 16(17) enepregnant 11α hydroxyl group, can solve the problems of green color of oxidation products and excessive heavy metals, difficult and easy to filter out, and inability to eradicate chromium ions, etc.

Inactive Publication Date: 2014-06-18
TIANJIN JINYAO GRP
View PDF2 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Oxidation of 11α-hydroxyl to 11-keto group is oxidized with acetic acid and chromium trioxide, the reaction is relatively strong, and if there are double bonds in other positions of pregnane, it is also easy to be oxidized, resulting in impurities. After the reaction of chromium trioxide, extremely The fine chromium hydroxide is muddy and extremely difficult to filter out. More importantly, the color of the oxidized product is green and the heavy metals exceed the standard due to the inability to eradicate the chromium ions, which cannot be removed even after repeated refining.

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
  • Selective oxidation method for hexa(hepta)decene-pregna-11-alpha-hydroxy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Pregna-4,16(17)-diene-3,20-diketone-11α-hydroxyl 10g (content 96.8%, maximum impurity <2%), dimethyl sulfoxide 30g in 100ml chloroform at -15°C , dicyclohexylcarbodiimide 5g for reaction, after the substrate content was detected by high performance liquid phase <1%, adding pyridine to adjust the pH to 8.5-10, and generating pregna-4,16 (17) by high performance liquid phase detection -diene-3,11,20-trione, concentrated under reduced pressure to no chloroform, cooled to 0°C, diluted with 100ml of 0°C water under stirring, and filtered to obtain pregna-4,16(17)-diene- 9.91g of 3,11,20-triketone, the content is 96.2%, and the maximum impurity is <2%.

Embodiment 2

[0019] Pregnant-4,16(17)-diene-3,20-diketone-11α-hydroxyl 10g in 50ml chloroform at -20°C (98.5% content, maximum impurity <2%), dimethylmethylene 6g of sulfone and 8g of phenyl phosphate dichloride were reacted. After the substrate content was detected by high performance liquid phase <1%, pyridine was added to adjust the pH to 8.5-10, and pregna-4, 16 (17 )-diene-3,11,20-trione, concentrated under reduced pressure to no chloroform, cooled to 0°C, diluted with 100ml of 0°C water under stirring, and filtered to obtain pregna-4,16(17)-diene -3,11,20-triketone 9.86g, content 98.1%, maximum impurity <2%.

Embodiment 3

[0021] Pregna-4,16(17)-diene-3,20-diketone-11α-hydroxyl 10g (content 97.4%, maximum impurity <2%), dimethyl sulfoxide 10g in 70ml chloroform at -30°C , N-chlorosuccinimide 30g reacted, after the substrate content was detected by high performance liquid phase <1%, triethylamine was added to adjust the pH to 8.5-10, and pregna-4,16 was generated by high performance liquid phase detection After (17)-diene-3,11,20-trione, add 15ml of water, shake, and then separate layers, take the chloroform layer, discard the water layer, if so, concentrate the chloroform layer under reduced pressure for 3 times, until the basic After chloroform-free, recrystallize with methanol, cool to 0°C for 2 hours, and filter to obtain 9.21 g of pregna-4,16(17)-diene-3,11,20-trione with a content of 99.1%. Maximum impurity <1%.

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 provides a selective oxidation method for hexa(hepta)decene-pregna-11alpha-hydroxy. According to the invention, pregna-4,16(17)-diene-3,20-diketone-11alpha-hydroxy is used as a substrate and reacts with dimethyl sulfoxide and an activator in liquid chloroalkane, and alkali is added after completion of the reaction so as to adjust a pH value to 8.5 to 10, thereby obtaining pregna-4,16(17)-diene-3,11,20-triketone.

Description

Technical field: [0001] The invention relates to a method for selective oxidation of 16(17) engesterone 11α hydroxyl Background technique: [0002] Oxidation of pregnane 11α hydroxyl group to 11 ketone group is a common reaction of corticosteroids. In the research on the synthesis of steroid hormones, it was found that the chemical modification of molecular structure, such as the introduction of certain groups, can greatly increase the efficacy of drugs and reduce side effects , and can change the specificity of the action. For example, the C-11 oxygen-containing functional group introduced in the steroid structure is indispensable for the anti-inflammatory effect and glucose metabolism effect of the drug. Among them, the 11β-hydroxyl group is an essential group for anti-inflammatory drugs. The highly effective corticosteroids currently developed Drug-like drugs almost without exception contain 11β-hydroxyl groups. Therefore, the introduction of 11β-hydroxyl in steroid mol...

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): C07J13/00
Inventor 孙亮赵琳
Owner TIANJIN JINYAO GRP
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com