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Optical selective process synthesis method of (5R)-5-hydroxytriptolide

A compound and inert solvent technology, applied in the field of optical selective process synthesis of -5-hydroxytriptolide, can solve the problem of high labor protection and environmental protection requirements, high requirements for production workshops and equipment, and the impossibility of mass production Continuous acquisition and other issues to achieve the effects of avoiding column chromatography separation, low protection requirements, and reduced toxicity

Active Publication Date: 2021-12-07
SHANGHAI VASTPRO TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, triptolide is basically a natural extract, the price is extremely high (4000 yuan / gram), and the source is unstable
The content of triptolide in the whole root of Tripterygium wilfordii is 0.0018%, so it is almost impossible to continuously obtain it in large quantities, which cannot meet the needs of future clinical medication
Moreover, triptolide is extremely toxic, and the synthesis operation process has extremely high requirements for labor protection and environmental protection.
Method (2) (3) In the synthesis process, triptolide is used as the starting material, the process safety risk is relatively high, the requirements for the production workshop and equipment are extremely high, and the production cost increases

Method used

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  • Optical selective process synthesis method of (5R)-5-hydroxytriptolide
  • Optical selective process synthesis method of (5R)-5-hydroxytriptolide
  • Optical selective process synthesis method of (5R)-5-hydroxytriptolide

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Experimental program
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Effect test

Embodiment 1

[0041]

[0042] To a three-neck flask was added 50g (1 eq) Triptonide (compound of formula II) and dioxane 500mL, followed by addition of selenium dioxide 124g (8eq), heated to reflux and stirred until the reaction was complete. After bringing back to room temperature and filtered to remove insolubles. The filtrate was concentrated, water was added and extracted with dichloromethane. The organic layer was washed with water continues, and concentrated to give crude compound of formula III, as a pale yellow solid, yield 88%. The crude product was used without purification in the next reaction.

Embodiment 2

[0044]

[0045] (Compound of formula II) to a three-neck flask was added 3g (1 eq) and dimethyl sulfoxide Triptonide 20mL, followed by addition of selenium dioxide 3.7g (4eq), was heated to 120 to 100 [deg.] C and stirred until the reaction was complete. After bringing back to room temperature and filtered to remove insolubles. The filtrate was concentrated, extracted with ethyl acetate and water. The organic layer was washed with water continues, and concentrated to give crude compound of formula III, 80% yield. The crude product was used without purification in the next reaction.

Embodiment 3

[0047]

[0048]17 g of formula III compound was added to the three flask and 170 ml of anhydrous tetrahydrofuran, and dissolved to -60 to 50 ° C after dissolving. This temperature was maintained and 100 ml (2.2 eq) of 1M triamoliol hydride tetrahydrofuran was added dropwise. After stirring until the reaction was complete, raised to 0-10 ° C. This temperature was maintained at 170 mL of water, then the pH was adjusted with a 5% hydrochloric acid solution. After the aqueous phase was extracted twice with ethyl acetate, the organic phase was combined, filtered through 50 g of silica gel, the filter cake was sufficiently collected with ethyl acetate, and the filtrate was concentrated to give a crude product. The crude filtered ethanol was purified and purified, and the compound of formula I, white powder was obtained, and the yield was 83%. 1 H NMR (DMSO-D 6 400MHz): δ = 5.34 (S, 1H), 4.60 (S, 2H), 4.60 (D, J = 7.2 Hz, 1H), 3.73 (D, J = 3.2Hz, 1H), 3.53 (D, J = 2.8Hz, 1H), 3.37 (D, ...

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Abstract

The invention relates to an optical selective process synthesis method of (5R)-5-hydroxytriptolide, and particularly discloses a method for obtaining a pure product of (5R)-5-hydroxytriptolide (a compound as shown in a formula I in the description) by taking triptolide ketone (a compound as shown in a formula II in the description) as a raw material through oxidation and reduction. The method is simple and stable in raw material source, simple in post-treatment operation and easy to industrialize.

Description

Technical field [0001] The present invention belongs to the field of drug synthesis, specifically relates to a (5R) -5- optically selective process of synthesis of hydroxy triptolide. Background technique [0002] (5R) -5- hydroxy triptolide sheet (trade name: Lei Tang Shu) Shanghai Pharmaceutical Group Inc. is developing new drugs chemical drugs, hormone-based purified by, processing, chemical modification of the structure obtained by the transformation of Triptolide compound of. Table nonclinical studies Lei Tang Shu having excellent immunosuppressive activity, a significant effect in animal models of arthritis disease, but also has a stable pharmacokinetic parameters. Lei Teng Shu expected to rheumatoid arthritis clinical indications, can play a good effect, in line with safe, effective and quality controlled standard therapy for the majority of patients with rheumatoid arthritis provided an effective treatment way. [0003] Currently, -5-hydroxy triptolide prepared are the fo...

Claims

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Application Information

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IPC IPC(8): C07J73/00
CPCC07J73/003Y02P20/55
Inventor 郭朋朱文峰
Owner SHANGHAI VASTPRO TECH DEV CO LTD
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