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A kind of crystal form of ethyl 5-bromotetrandrine formate and its preparation method

A technology of tetrandrine and ethyl formate, which is applied in the field of medicine and can solve problems such as research on the crystal form of undeveloped compounds

Active Publication Date: 2021-09-28
CHONGQING MEDICAL & PHARMA COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

On this basis, through further structural optimization, a new type of brominated derivative with stronger activity - 5-bromotetrandrine ethyl formate (see the following structural formula W17), literature (Ping He et al., JAsian Nat ProdRes ,2012,14(6):564-576.) reported the synthesis method of W17 and obtained an amorphous sample, but did not study the crystal form of the compound, and so far, there is no other literature reporting the crystal form of the compound

Method used

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  • A kind of crystal form of ethyl 5-bromotetrandrine formate and its preparation method
  • A kind of crystal form of ethyl 5-bromotetrandrine formate and its preparation method
  • A kind of crystal form of ethyl 5-bromotetrandrine formate and its preparation method

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Experimental program
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Embodiment 1

[0046] Weigh 500 mg of 5-bromotetrandrine ethyl formate amorphous (obtained with reference to the literature Ping He et al., JAsianNatProd Res, 2012, 14(6):564-576, the same below), and add it to a 25ml round bottom In the flask, 10 ml of ethanol aqueous solution (7.5 ml of ethanol: 2.5 ml of water) was added. Heat to 70-75°C, stir for 3 hours, add 5ml of acetone dropwise, stir for 30min, then cool down to -5-5°C, crystallize, filter, wash the filter cake with 2ml of acetone, and dry at 50-60°C for 4 hours in vacuum. 423 mg of ethyl 5-bromotetrandrine formate crystal form I was obtained, with a yield of 84.6%. At room temperature, take 50 mg of crystal form I sample for x-ray powder diffraction (RINT 2100Ultima X-ray diffractometer, Cu target, graphite crystal monochromator filter, working voltage: 40kV, current: 150mA, receiving slit: 0.3nm, 2θ Angle is 3°~40°, step size: 0.02°) test, obtained XRPD data of crystal form I, the results are shown in figure 1 .

Embodiment 2

[0048] Weigh 500 mg of amorphous ethyl 5-bromotetrandrine formate, add it into a 25 ml round bottom flask, and add 10 ml of ethanol aqueous solution (8 ml of ethanol: 2 ml of water). Heat to 70-75°C, stir for 3.5 hours, add 4ml of acetone dropwise, stir for 30min, then cool down to -5-0°C, crystallize, filter, wash the filter cake with 2ml of acetone, and dry at 50-60°C for 4 hours in vacuum. 430 mg of ethyl 5-bromotetrandrine formate, crystalline form I, was obtained with a yield of 86.0%.

Embodiment 3

[0050] Weigh 500 mg of amorphous ethyl 5-bromotetrandrine formate, add it into a 25 ml round bottom flask, and add 10 ml of isopropanol aqueous solution (8 ml of isopropanol: 2 ml of water). Heat to 70-75°C, stir for 3.5 hours, add 5ml of acetone dropwise, stir for 30min, then cool down to -5-0°C, crystallize, filter, wash the filter cake with 2ml of acetone, and dry in vacuum at 50-60°C for 4 hours. 418 mg of ethyl 5-bromotetrandrine formate crystal form I was obtained with a yield of 83.6%.

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Abstract

The invention discloses a new crystal form of ethyl 5-bromotetrandrine formate, which is characterized in that, using Cu-Ka radiation, the X-ray powder diffraction represented by the 2θ angle is at 6.03, 10.96, There are characteristic peaks at 13.13, 15.80, 17.42, 18.36, and 26.54±0.2. The invention also discloses a preparation method of the new crystal form of 5-bromotetrandrine ethyl formate.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a new crystal form of 5-bromotetrandrine ethyl formate and a preparation method, in particular to a crystal form I of 5-bromotetrandrine ethyl formate and Preparation. Background technique [0002] Bisbenzylisoquinoline alkaloid Tetrandrine (Tetrandrine), also known as tetrandrine or tetrandrine, is the main active ingredient in the root of Tetrandrine (the following structural formula). Clinically, it is mainly used for rheumatic pain, arthralgia, neuralgia, and also for silicosis. Studies have reported that tetrandrine also has certain anti-lung cancer, chronic myelogenous leukemia, liver cancer, neuroblastoma, breast cancer, etc., and its mechanism is related to reversing multidrug resistance, inducing apoptosis, radiosensitization, and inhibiting tumors. Related to angiogenesis (Xu Meng et al., New Chinese Medicine, 2006, 38(6):90; CN101199529A; CN102875560A.). [0003] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/18A61K31/4748A61P35/00
CPCA61P35/00C07B2200/13C07D491/18
Inventor 张稳稳刘小东
Owner CHONGQING MEDICAL & PHARMA COLLEGE
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