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Crystal form B of tetrahydrothienopyridine compound as well as preparation method, composition and application thereof

A technology for tetrahydrothienopyridine and compounds, which is applied in the field of medicinal chemistry, can solve the problems of poor crystal stability, inability to form medicines, and many impurities, and achieves the effects of less impurities, favorable control of tablet weight differences, and cheap and easy-to-obtain solvents.

Active Publication Date: 2020-11-17
CHENGDU SHIBEIKANG BIOLOGICAL MEDICINE TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] One of the objects of the present invention is to provide a tetrahydrothienopyridine compound (S)-2-(2-chlorophenyl)-2-((S)-2-oxo-2,6 ,7,7a-Tetrahydrothiophene[3,2-c]pyridin-5(4H)yl)methyl acetate B crystal form solves the problem of many impurities, low content, poor stability of the crystal form in the prior art, and cannot be used as a medicine The problem

Method used

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  • Crystal form B of tetrahydrothienopyridine compound as well as preparation method, composition and application thereof
  • Crystal form B of tetrahydrothienopyridine compound as well as preparation method, composition and application thereof
  • Crystal form B of tetrahydrothienopyridine compound as well as preparation method, composition and application thereof

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Embodiment 1

[0049] This embodiment provides the preparation method of the crystal form B of the compound of formula I structure of the present invention, specifically:

[0050] Take 5.0 g of the crude product of a single isomer compound shown in formula I and put it into a 100 mL eggplant-shaped bottle, add 40 mL of acetone, heat up to 60°C and stir to dissolve, basically dissolve, filter while hot, stir the filtrate in a 100 mL beaker, and slowly cool down to room temperature, stirred overnight for crystallization. Drying yielded 0.58 g of solid, yield 58%. The crystallization is at about 11.21±0.2° (7.90), 12.61±0.2° (7.02), 14.69±0.2° (6.03), 16.14±0.2° (5.49), 17.81±0.2° (4.98), 19.42±0.2° (4.57 ), 20.22±0.2°(4.39), 20.76±0.2°(4.27), 22.10±0.2°(4.02), 23.24±0.2°(3.83), 24.31±0.2°(3.66), 27.01±0.2°(3.30), There are characteristic peaks at 27.68±0.2° (3.22), 28.57±0.2° (3.12), and 31.09±0.2° (2.88). See the DSC spectrum figure 2 , with one and only one sharp melting endothermic pea...

Embodiment 2

[0052] This embodiment provides the preparation method of the crystal form B of the compound of formula I structure of the present invention, specifically:

[0053] Take 100 mg of the crude product of the single isomer compound shown in formula I, put it into a 10 mL eggplant-shaped bottle, add 5 mL of acetone, shake and dissolve at 60 ° C, filter while it is hot, put the filtrate into a clean 5 mL eggplant-shaped bottle and let it stand slowly to cool down to Room temperature, obtain compound single crystal shown in formula I, crystallinity is high, and single crystal diffraction pattern sees Figure 4 , after low-temperature grinding of the single crystal, its X-ray powder diffraction pattern and DSC pattern were studied and compared, and the product was determined to be B crystal form.

Embodiment 3

[0055] This embodiment provides the preparation method of the crystal form B of the compound of formula I structure of the present invention, specifically:

[0056] Take 1.0 g of the crude product of a single isomer compound represented by formula I and put it into a 100 mL eggplant-shaped bottle, add 35 mL of acetonitrile, heat up to 60 ° C and stir to dissolve, basically dissolve, filter while hot, stir the filtrate in a 100 mL beaker, and slowly cool down to room temperature, stirred overnight for crystallization. Drying yielded 0.42 g of solid, a yield of 42%. Its X-ray powder diffraction and DSC patterns are researched and compared, and it is confirmed that the product is B crystal form.

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Abstract

The invention discloses a crystal form B of a tetrahydrothienopyridine compound with a structure as shown in a formula I, and a preparation method, a composition and application thereof. The inventionaims to solve the problems of many impurities, low content, poor crystal form stability and incapability of forming a medicine in the prior art. When the crystal form B is subjected to Cu-K alpha radiation, in an X-ray powder diffraction pattern expressed by a 2theta angle, characteristic peaks occur at 11.21 + / - 0.2 degrees, 12.61 + / - 0.2 degrees, 14.69 + / - 0.2 degrees, 16.14 + / - 0.2 degrees, 17.81 + / - 0.2 degrees, 20.22 + / - 0.2 degrees and 22.10 + / - 0.2 degrees. The crystal form B provided by the invention has the advantages of few impurities, good stability, good crystallinity and reproducibility, and is suitable for industrial production; and unexpected stronger ADP-induced platelet aggregation resistance and better flowability are also achieved.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, in particular to tetrahydrothienopyridine compound (S)-2-(2-chlorophenyl)-2-((S)-2-oxo-2,6,7,7a- Crystal form B of methyl tetrahydrothiophene [3,2-c]pyridin-5(4H)yl)acetate, its preparation method, composition and application. [0002] technical background [0003] According to the "China Cardiovascular Disease Report 2017" data, the prevalence and mortality of cardiovascular disease (CVD) in my country have been on the rise in recent years. It is estimated that the number of CVD patients is 290 million, of which 13 million are stroke and 11 million are coronary heart disease. , heart failure 4.5 million, high blood pressure 270 million. According to the latest survey data published in JAMA Cardiology, the total number of deaths caused by CVD in my country in 2016 was as high as 3.97 million, accounting for more than 40% of the total number of deaths from diseases among residents, and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04A61K31/4365A61P9/10A61P9/00A61P9/04
CPCC07D495/04A61P9/10A61P9/00A61P9/04C07B2200/13A61K31/4365A61P7/02
Inventor 岑国栋杨茂廷谭少军杨宁远
Owner CHENGDU SHIBEIKANG BIOLOGICAL MEDICINE TECH CO LTD
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