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Method for Selective Oxidation of Polyhydroxypregna 11α Hydroxyl

A technology of pregnane and hydroxyl, which is applied in the field of selective oxidation of polyhydroxypregna 11α hydroxyl, which can solve the problems that chromium ions cannot be eradicated, difficult to filter out, and unable to be removed after repeated refining

Active Publication Date: 2016-12-21
TIANJIN JINYAO GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Oxidation of 11α-hydroxyl to 11-keto group is carried out with acetic acid and chromium trioxide. The reaction is relatively strong. If there are hydroxyl groups in other positions, it is also easy to be oxidized, resulting in impurities, CrO 3 After the reaction, extremely fine chromium hydroxide will be produced, which is in the form of mud, which is extremely difficult to filter out. More importantly, due to the inability to eradicate chromium ions, the color of the oxidation product is green and heavy metals exceed the standard, which cannot be removed even after repeated refining.

Method used

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  • Method for Selective Oxidation of Polyhydroxypregna 11α Hydroxyl

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Experimental program
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Embodiment 1

[0016] Pregn-4-ene-3,20-diketone-11α, 17α-dihydroxyl 10g (content 97.4%, maximum impurity <2%), dimethyl sulfoxide 30g, bicyclo in 100ml chloroform at -15℃ 5g of hexylcarbodiimide was reacted, and 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-ene-3,11,20 was generated by high performance liquid phase detection -Triketone-17α-hydroxyl, 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-ene-3,11,20-triketone-17α-hydroxyl 9.84g, the content is 96.3%, and the maximum impurity is <2%.

Embodiment 2

[0018] In 50ml chloroform at -20°C, the substrate pregn-4-ene-3,20-diketone-11α, 17α-dihydroxyl 10g (content 97.8%, maximum impurity <2%), dimethyl sulfoxide 6g, 8g of phenyl phosphate dichloride was reacted, and 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-ene-3,11 was generated by high performance liquid phase detection. 20-triketone-17α-hydroxyl was 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-ene-3,11,20-trione-17α- Hydroxyl 9.84g, content 95.9%, maximum impurity <2%.

Embodiment 3

[0020] Pregn-4-ene-3,20-diketone-11α, 17α-dihydroxyl 10g (content 96.2%, maximum impurity <2%), dimethyl sulfoxide 10g, N- 30g of chlorosuccinimide was reacted, and after the substrate content was detected by HPLC <1%, triethylamine was added to adjust the pH to 8.5-10, and pregna-4-ene-3 was generated by HPLC detection, After 11,20-triketone-17α-hydroxyl, add 15ml of water, shake, and then separate layers, take the chloroform layer, discard the water layer, if so, concentrate the chloroform layer for 3 times under reduced pressure, until there is basically no chloroform, use Methanol was recrystallized, cooled to 0°C for 2 hours, and filtered to obtain 9.07 g of pregna-4-ene-3,11,20-trione-17α-hydroxyl, with a content of 98.9% and the largest impurity <1%.

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Abstract

The invention provides a selective oxidation method for selective oxidation method for polyhydroxy-pregna-11alpha-hydroxy. According to the invention, pregna-4-ene-3,20-diketone-11alpha,17alpha-dihydroxy 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-ene-3,11,20-triketone-17alpha-hydroxy.

Description

Technical field: [0001] The invention relates to a method for selective oxidation of polyhydroxypregna 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 mole...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J5/00
Inventor 孙亮赵琳
Owner TIANJIN JINYAO GRP