Cycloastragenol new crystal form A and preparation method thereof

A technology of cycloastragalus and crystal form, which is applied in the field of organic chemical drug preparation, can solve the problems of non-compliance with green environmental protection, injury to operators, and many reaction steps, etc.

Pending Publication Date: 2020-07-07
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] For the synthesis of cycloastragenol, the synthesis of cycloastragenol is more reported to be obtained by the hydrolysis of astragaloside IV. For example, Chinese patent CN1809364 proposes the method of hydrolyzing astragaloside IV with acid and purifying by silica gel column chromatography to obtain cycloastragenol. However, practice has proved that it produces The ratio of the ring-opening by-product - astragalol is relatively high and the process is complicated, making it difficult to produce industrially
Chinese patent CN103880910 adopts the redox method to prepare cycloastragenol, and there are many reaction steps, using strong oxidant periodate, sodium periodate or potassium periodate, strong reducing agent sodium borohydride, potassium borohydride, etc., and the reaction After adding ethylene glycol in the process, a large amount of formaldehyde will be produced, which will cause certain harm to the operator, and does not meet the requirements of green environmental protection
As an important anti-aging drug molecule, cycloastragenol has a lot of research reports on its preparation and application, but there are relatively few reports on its crystal form

Method used

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  • Cycloastragenol new crystal form A and preparation method thereof
  • Cycloastragenol new crystal form A and preparation method thereof
  • Cycloastragenol new crystal form A and preparation method thereof

Examples

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Comparison scheme
Effect test

Embodiment 1

[0039] Add 20.0g of cycloastragenol to 120mL of methanol solution, heat to 60°C-65°C until cycloastragenol is completely dissolved, add 500mL of petroleum ether and stir, slowly lower to 40°C-45°C and keep stirring for 30 minutes, then keep it for 8 hours ; Lower the temperature to 30°C to 35°C and continue to heat and stir for 40 minutes, then keep the heat to stand for 10 hours; drop to 20°C to 25°C and continue to heat and stir for 30 minutes, then keep the heat to stand for 10 hours; lower to 5°C to 10°C and continue to heat and stir for 30 Minutes, heat preservation and standing for 8 hours; finally lower the temperature to -8°C and continue heat preservation and stirring for 6 hours, filter, and vacuum dry at 40°C to obtain cycloastragenol crystal form A with a yield of 82.9% and a purity of 99.96%.

Embodiment 2

[0041] Add 20.0g cycloastragenol into 100mL ethyl acetate solution, heat to 60°C-65°C until cycloastragenol is completely dissolved, add 600mL water and stir, slowly cool down to 40°C-45°C and keep stirring for 30 minutes, then keep it for 10 minutes Hours; drop to 30°C-35°C and continue to keep warm and stir for 40 minutes, keep warm for 10 hours; drop to 20°C-25°C and continue to keep warm and stir for 30 minutes, keep warm for 10 hours; drop to 5°C-10°C and continue to keep warm and stir After 30 minutes, keep it warm for 8 hours; finally lower the temperature to 0°C, continue to keep warm and stir for 6 hours, filter, and dry under vacuum at 40°C to obtain cycloastragenol crystal form A with a yield of 81.8% and a purity of 99.92%.

Embodiment 3

[0043]Add 20.0g of cycloastragenol to 800mL ethanol solution, heat to 60°C-65°C until cycloastragenol is completely dissolved, add 1000mL of n-hexane, stir and slowly cool down to 40°C-45°C, keep stirring for 30 minutes, keep the temperature for 6 hours; Lower the temperature to 30°C to 35°C and continue to heat and stir for 40 minutes, and then keep it for 10 hours; lower it to 20°C to 25°C and continue to heat and stir for 30 minutes, and keep it for 10 hours; lower it to 5°C to 10°C and continue to heat and stir for 30 minutes , heat preservation and standing for 10 hours; finally lower the temperature to -10°C, continue heat preservation and stirring for 6 hours, filter, and vacuum dry at 40°C to obtain cycloastragenol crystal form A with a yield of 80.4% and a purity of 99.94%.

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Abstract

The invention belongs to the technical field of organic chemical medicine preparation, and specifically relates to a cycloastragalol crystal form A and a preparation method thereof. The crystal form uses Cu-Kalpha radiation, and X-ray powder diffraction (X-RPD) represented by a 2theta angle has characteristic diffraction peaks when 2theta is equal to 4.9 +/-0.2 degrees, 9.8 +/-0.2 degrees, 13.2 +/-0.2 degrees, 15.7 +/-0.2 degrees and the like. The crystal form has good chemical stability and crystal form purity, large-scale preparation is easy, and the preparation method is simple to operate,can be better suitable for preparation of pharmaceutical preparations and large-scale production, and has broad application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic chemical drug preparation, and in particular relates to a new crystal form A of cycloastragenol and a preparation method thereof. Background technique [0002] Cycloastragenol (CAG), CAS number: 78574-94-4, molecular formula C 30 h 50 o 5 , is a cyclopine-type tetracyclic three-mushroom compound, the structure of which is shown in formula 1: [0003] [0004] Cycloastragenol is the only telomerase activator discovered today, which delays the shortening of telomeres by increasing telomerase, and cycloastragenol is considered to have anti-aging effects. A large number of modern medical studies have proved that astragaloside IV can reduce the damage of ischemia-reperfusion brain tissue by enhancing the body's ability to scavenge oxygen free radicals, inhibit peroxidation, and reduce neuronal calcium overload, so that cycloastragenol can be used in various Anti-cancer, prevention and treatment ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J53/00A61K31/58
CPCC07J53/004C07B2200/13
Inventor 张贵民张朝花翟立海郭立红
Owner LUNAN PHARMA GROUP CORPORATION
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