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Crystal form of benzoylaminopyridine derivative, and application thereof

A technology of crystal forms and diffraction peaks, which can be applied to medical preparations containing active ingredients, drug combinations, digestive systems, etc., and can solve problems such as undisclosed crystal structures and undisclosed compound microstructures.

Active Publication Date: 2020-03-27
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the patent application did not disclose the specific microstructure of the compound, that is, did not disclose any crystal structure

Method used

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  • Crystal form of benzoylaminopyridine derivative, and application thereof
  • Crystal form of benzoylaminopyridine derivative, and application thereof
  • Crystal form of benzoylaminopyridine derivative, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0133] Embodiment 1 The crystal form I of the compound of formula (I)

[0134] 1. Preparation of Form I

[0135] Compound 5-(4-cyclopropyl-1H-imidazol-1-yl)-N-(6-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2 ,4] Triazol-3-yl)pyridin-2-yl)-2-fluoro-4-methylbenzamide (506mg) was added into dichloromethane (10.0mL) and stirred to dissolve, then absolute ethanol was added dropwise (5.0 mL) was stirred for 5 minutes, allowed to stand at room temperature for 3 days, filtered with suction, and the filter cake was vacuum-dried at 60° C. to obtain a white solid (472 mg, 93.28%).

[0136] 2. Identification of Form I

[0137] (1) Analysis and identification by Empyrean X-ray powder diffraction (XRPD): using Cu-Kα radiation, with the following characteristic peaks expressed in angle 2θ: 7.66°, 8.35°, 8.95°, 10.20°, 11.76°, 14.51°, 14.82 °,15.74°,16.61°,17.60°,17.73°,18.28°,18.76°,20.02°,21.20°,21.59°,22.32,23.51°,24.87°,25.96°,26.80°,27.74°,28.86°,29.89 °, 31.09°, 31.86°, 32.82°, 33.72°, 35....

Embodiment 2

[0139] Embodiment 2 The crystal form II of the compound of formula (I)

[0140] 1. Preparation of Form II

[0141] The compound 5-(4-cyclopropyl-1H-imidazol-1-yl)-N-(6-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4 ]triazol-3-yl)pyridin-2-yl)-2-fluoro-4-methylbenzamide (1.27g) was added in acetone (20.0mL), beaten at room temperature for 7.5 hours, suction filtered, and the filter cake was Drying in vacuo afforded a white solid (1.16 g, 91.34%).

[0142] 2. Identification of Form II

[0143] (1) Analysis and identification by Empyrean X-ray powder diffraction (XRPD): using Cu-Kα radiation, with the following characteristic peaks expressed in angle 2θ: 7.85°, 8.66°, 12.95°, 13.72°, 13.95°, 14.66°, 15.82 °,16.62°,17.36°,17.81°,17.98°,18.85°,20.25°,20.69°,21.00°,21.57°,21.95°,22.14°,23.33°,23.73°,23.97°,24.30°,24.57°, 25.32°, 26.06°, 26.49°, 27.52°, 28.12°, 29.20°, 29.56°, 30.01°, 30.20°, 30.48°, 31.00°, 31.87°, 32.25°, 33.56°, 34.49°, 35.14°, 36.64° , 37.61°, 38.11°, 40.13°, 41.1...

Embodiment 3

[0145] Embodiment 3 The crystal form III of the compound of formula (I)

[0146] 1. Preparation of Form III

[0147] The compound 5-(4-cyclopropyl-1H-imidazol-1-yl)-N-(6-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4 ]triazol-3-yl)pyridin-2-yl)-2-fluoro-4-methylbenzamide (551mg) was added to methanol (11.0mL), beaten at room temperature for 17 hours, suction filtered, and the filter cake was vacuum-dried at room temperature , to obtain a white solid (411 mg, 74.59%).

[0148] 2. Identification of Form III

[0149] (1) Analysis and identification by Empyrean X-ray powder diffraction (XRPD): using Cu-Kα radiation, it has the following characteristic peaks expressed in angle 2θ: 8.82°, 10.38°, 11.55°, 12.10°, 12.58°, 13.30°, 14.83 °,15.22°,16.60°,17.73°,18.47°,19.53°,20.32°,21.03°,21.70°,22.49°,23.01°,23.47°,24.45°,25.88°,27.13°,27.55°,28.19°, 29.43°, 31.67°, 33.18°, 34.99°, 36.99°, 38.45°, 40.94°, 43.95°, 45.32°, 48.08° and 50.28°, there is an error tolerance of ±0.2°.

[0150] (...

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PUM

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Abstract

The invention relates to a crystal form of a benzoylaminopyridine derivative, and an application of the crystal form, and also relates to a pharmaceutical composition containing the crystal form, andan application of the crystal form or the pharmaceutical composition in the preparation of drugs for preventing, treating or alleviating ASK1-regulated diseases of patients.

Description

technical field [0001] The invention belongs to the field of medicines, and relates to crystal forms of benzamidopyridine derivatives and uses thereof, in particular to 5-(4-cyclopropyl-1H-imidazol-1-yl)-N-(6-(6,7 -dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)pyridin-2-yl)-2-fluoro-4-methylbenzamide (formula ( I) the crystal form of the shown compound) and its use, and further relates to a pharmaceutical composition comprising said crystal form. The crystal form or the pharmaceutical composition is used for preventing, treating or alleviating diseases regulated by ASK1 in patients. Background technique [0002] Apoptosis signal-regulating kinase 1 (ASK1) is a member of the mitogen-activated protein kinase kinase kinase (MAP3Ks) family, and MAP3Ks can activate c-Jun N c-Jun N-terminal protein kinase (JNK) and p38 MAP (mitogen-activated protein) kinase (Ichijo, H., Nishida, E., Irie, K., Dijke, P.T., Saitoh, Moriguchi, T. , Matsumoto, K., Miyazono, K., and Gotoh, Y. (1997) ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61P37/06A61P29/00A61P9/00A61P11/00A61P1/16A61P25/28A61P3/10A61P13/12A61K31/4439
CPCA61P1/16A61P3/10A61P9/00A61P11/00A61P13/12A61P25/28A61P29/00A61P37/06C07B2200/13C07D487/04
Inventor 陈亮李成蹊梁小小潘圣强杨新业王晓军张英俊宗乔崔艳慧
Owner SUNSHINE LAKE PHARM CO LTD
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