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Crystal form of Dimethylamino Arglabin hydrochloride

A technology of crystallization of dimethylamino and hydrochloride, applied in organic active ingredients, medical preparations containing active ingredients, organic chemistry, etc., can solve problems such as slow dissolution, difficult preparation of preparations, and easy generation of static electricity

Active Publication Date: 2011-09-21
INNOVSTONE THERAPEUTICS LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The dimethylaminoagrabine hydrochloride precipitated by the patented method is a powder granular solid, which dissolves slowly in water and is prone to static electricity, which brings difficulties to the preparation of preparations.

Method used

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  • Crystal form of Dimethylamino Arglabin hydrochloride
  • Crystal form of Dimethylamino Arglabin hydrochloride
  • Crystal form of Dimethylamino Arglabin hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: Preparation of dimethylaminoagrabine hydrochloride of form I (with reference to ZL97181524.0 method)

[0040] Add 1 g (3.4 mmol) of dimethylaminoagrabine to 20 ml of absolute ethanol, stir and dissolve at 10°C, then bubble hydrogen chloride gas into the solution to make the pH of the solution reach 5.0-5.5, evaporate the ethanol, add 20ml of ethyl acetate was stirred for crystallization, and suction filtered. The resulting product was dissolved in 20ml of chloroform, the chloroform was evaporated, and 20ml of ethyl acetate was added under vigorous stirring, and the resulting precipitate was dried in a vacuum oven at 25°C for 5h to obtain 0.5g (44.4%) of dimethylaminoagrabine in form I Hydrochloride, the HPLC purity is 95.1%.

Embodiment 2

[0041] Embodiment 2: Preparation of dimethylaminoagrabine hydrochloride of form I

[0042] Add 1 g (3.4 mmol) of dimethylaminoagrabine into 40 ml of ethyl acetate, stir to dissolve at 10°C, add 0.4 ml of 35% ethanol hydrochloric acid solution dropwise, stir for 30 min, precipitate crystals, filter with suction, and obtain precipitates in a 25°C After drying in a vacuum oven for 5 h, 0.65 g (57.8%) of form I dimethylaminoagrabine hydrochloride was obtained, with an HPLC purity of 99.6%.

Embodiment 3

[0043] Example 3: Preparation of Dimethylaminoagrabine Hydrochloride of Form II

[0044] Add 2 g (6.1 mmol) of dimethylaminoagrabine hydrochloride in form I into 20 ml of acetone, heat to dissolve, crystallize at 0±10° C., and filter with suction. After drying in a vacuum oven at 22° C. for 5 h, 1.0 g (50%) of dimethylaminoagrabine hydrochloride in form II was obtained, with an HPLC purity of 99.8%.

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Abstract

The invention relates to a novel crystal form of Dimethylamino Arglabin hydrochloride, a preparation method and therapeutic use thereof. The crystal form of Dimethylamino Arglabin hydrochloride provided in the invention, and has characteristic peaks at 13.02+ / -0.2, 19.38+ / -0.2, 25.80+ / -0.2, and 27.70+ / -0.2 when using Cu-Ka radiation with lambda of 1.5405 and 2theta to represent X-ray diffraction spectra, wherein, the diffraction peak intensity of the peaks at 13.02+ / -0.2 is 100%. The crystal form of Dimethylamino Arglabin hydrochloride provided in the invention is scalelike crystallization, and is characteristics in that: the filtration is simple; drying is easy so as to achieve the stable performance during the drying; the crystal form is easy to be dissolved in water so as to achieve short dissolution time and decrease the degradation; the crystal form is static-free so as to be helpful for preparing following preparation products; and the crystal form has high purity of crystal with obvious effects of purification and is convenient for industrialized production.

Description

technical field [0001] The present invention relates to the solid-state chemistry of organic compounds, in particular to a new crystal form of dimethylaminoagrabine hydrochloride, its preparation method and its therapeutic use. Background technique [0002] Arglabin (Arglabin, whose structural formula is shown in Formula I), has a chemical name of 1,10β-epoxy-guaiac-3(4)-ene-6,12-lactone. [0003] [0004] Agrabin was first extracted from the petals and leaves of the local Absinthe genus Artemisia glabella Kar.Et Kir by Kazakhstan scientist S.M. Adeknov, and found that the compound has antitumor activity, but due to its poor water solubility , which is not conducive to further formulation development. [0005] Studies such as Adekenov found that the derivative of Agrabine——dimethylamino Agrabine hydrochloride (structural formula shown in formula II), has antitumor activity equivalent to Agrabine, but its water solubility is good, therefore, with Dimethylaminoagrabine hy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10A61K31/365A61P35/00
Inventor 王丙林郭小丰郭文敏于普刘长鹰白晓雪李晓花陈卫平刘翠艳李清娟
Owner INNOVSTONE THERAPEUTICS LTD
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