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Salt of benzoylaminopyridine derivative and application thereof in medicines

A technology of diffraction peaks and compounds, applied in the field of medicine, can solve problems such as undisclosed and undisclosed crystal structures of compounds

Active Publication Date: 2019-12-17
GUANGZHOU ANYANREN PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these patent applications did not disclose the crystal structure of the compound, nor did it disclose its pharmaceutically acceptable salt

Method used

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  • Salt of benzoylaminopyridine derivative and application thereof in medicines
  • Salt of benzoylaminopyridine derivative and application thereof in medicines
  • Salt of benzoylaminopyridine derivative and application thereof in medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] Embodiment 1 hydrobromide crystal form I

[0106] 1. Preparation of hydrobromide crystal form I

[0107] 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 (51.3mg, 0.116mmol) was added to isopropanol (1.0mL) and beaten for about 1 hour , and then dropwise added homemade 1mol / L hydrobromic acid solution (0.26mL, 0.26mmol), stirred for 10 hours and then suction filtered, and the filter cake was vacuum-dried overnight at 60°C to obtain a white solid (40.9mg, 67.4%).

[0108] 2. Identification of hydrobromide crystal form I

[0109] (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: 4.18°, 8.26°, 8.77°, 10.03°, 11.57°, 12.37°, 13.30 °,14.03°,14.31°,15.73°,16.25°,16.73°,17.49°,18.02°,18.64°,19.36°,19.75°,20.15°,20.63°,20.96°,21.90°,22.32°,22.75°, 23.25°, 24.11°, 24...

Embodiment 2

[0111] Embodiment 2 hydrobromide crystal form II

[0112] 1. Preparation of hydrobromide crystal form II

[0113] 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 (512.3mg, 1.155mmol) was added to acetone (10.0mL), beaten for 1 hour, then added Homemade 1 mol / L hydrobromic acid solution (1.3mL, 1.30mmol), stirred for 6 hours, suction filtered, and the filter cake was vacuum-dried at 60°C to obtain a white solid; the solid was beaten in ethanol (4.0mL) for about 10 hours After suction filtration, the filter cake was vacuum-dried overnight at room temperature to obtain a white solid (283.1 mg, 46.74%).

[0114] 2. Identification of hydrobromide crystal form II

[0115] (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: 9.76°, 10.30°, 11.04°, 11.40°, 11.63°, 13.89°, 14....

Embodiment 3

[0117] Embodiment 3 hydrobromide crystal form III

[0118] 1. Preparation of hydrobromide crystal form III

[0119] 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 (51.1mg, 0.115mmol) was added to ethyl acetate (1.0mL), and beating at 65°C for 1 hour, Then add a self-made 1mol / L hydrobromic acid solution (0.25mL, 0.250mmol), keep warm for half an hour and then cool to room temperature naturally; filter with suction, and dry the filter cake under vacuum at 60°C overnight to obtain a white solid (46.5mg, 66.68%) .

[0120] 2. Identification of hydrobromide crystal form III

[0121] (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: 6.86°, 9.70°, 11.06°, 12.68°, 13.51°, 13.75°, 14.10 °,15.53°,17.30°,17.61,18.56°,18.92°,19.27°,19.46°,20.02°,20.67°,21.04°,21.23°,21.6...

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Abstract

The invention relates to a salt of a benzoylaminopyridine derivative and application thereof in medicines, further relates to a pharmaceutical composition containing the salt or crystal form or a combination thereof, and application of the salt or crystal form or the pharmaceutical composition in preparing the medicines for preventing, treating or relieving diseases regulated by ASK1 of patients.

Description

technical field [0001] The invention belongs to the field of medicines, and relates to salts of benzamidopyridine derivatives and their application in medicines, 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 The hydrobromide and its application in medicine, and further relate to the crystal form of the hydrobromide and the pharmaceutical composition comprising the hydrobromide. The hydrobromide salt 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, also known as cell filament Mitogen-activated protein kinase kinase kinase 5 (mitogen-activated protein kinase kinase kinase 5, MAPKKK5, MAP3K5), consisting of 1375 amino acid residues, consists of 11 k...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/4439A61P37/02A61P29/00A61P9/00A61P13/12A61P11/00A61P1/16A61P25/28A61P3/10
CPCA61P1/16A61P3/10A61P9/00A61P11/00A61P13/12A61P25/28A61P29/00A61P37/02C07B2200/13C07D487/04
Inventor 薛伟才戴洪果李永攀张辉吴锡均
Owner GUANGZHOU ANYANREN PHARMA TECH CO LTD
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