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Salt of benzoylaminopyridine derivative and application thereof in medicines

A medicine and a technology for preparing medicine, applied in the field of crystal forms and pharmaceutical compositions containing the hydrochloride, capable of solving problems such as undisclosed crystal forms and crystal structures of undisclosed 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, none of these patent applications discloses the crystal structure of the compound, nor discloses its pharmaceutically acceptable salt and the crystal form of the 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

[0097] Example 1 Hydrochloride Crystal Form I

[0098] 1. Preparation of hydrochloride crystal form I

[0099] 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 (765mg, 1.72mmol) was added to ethanol (14.0mL), beaten for 45 minutes, then added dropwise The self-made 1mol / L hydrochloric acid solution (3.4mL, 3.4mmol) was stirred for about 1 hour, then ethyl acetate (14.0mL) was added, stirred and crystallized for about 6 hours; suction filtered, and the filter cake was vacuum-dried at 60°C overnight to obtain a white Solid (527.3 mg, 59.3%).

[0100] 2. Identification of Hydrochloride Form I

[0101](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: 6.90°, 7.24°, 9.88°, 10.14°, 13.48°, 13.83°, 14.22 °,14.49°,15.41°,15.92°,16.30°,17.30°,17.51°,17.75°,19.25°,19.48°,19.8...

Embodiment 2

[0103] Example 2 Hydrochloride Form II

[0104] 1. Preparation of Hydrochloride Form II

[0105] 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 (50.6mg, 0.114mmol) was added in isopropanol (1.0mL), and beating at 65°C for 30 minutes, Then dropwise added a self-made 1mol / L hydrochloric acid solution (0.13mL, 0.13mmol), incubated for 30 minutes, cooled naturally to room temperature, stirred and crystallized for about 9 hours; suction filtered, and the filter cake was vacuum-dried overnight at 60°C to obtain a white solid ( 44.2 mg, 80.7%).

[0106] 2. Identification of Hydrochloride Form II

[0107] (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°, 8.28°, 10.04°, 11.57°, 12.41°, 14.39°, 15.83 °,16.57°,16.85°,17.42°,18.71°,19.43°,19.90°,20.20°,20.74°,21.00...

Embodiment 3

[0108] Example 3 Hydrochloride Form III

[0109] 1. Preparation of hydrochloride crystal form III

[0110] 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 (1005.4mg, 2.26mmol) was added to dimethyl sulfoxide (10.0ml) for beating for 1 hour , then dropwise added homemade 1mol / L hydrochloric acid solution (2.5mL, 2.5mmol), then added ethyl acetate (20.0mL) solution and stirred for 2 days; suction filtered, and the filter cake was vacuum-dried overnight at 80°C to obtain a white solid (368.5 mg, 33.9%).

[0111] 2. Identification of Hydrochloride Form III

[0112] (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: 8.45°, 11.24°, 12.32°, 12.76°, 14.79°, 14.99°, 15.70 °,16.37°,16.95°,17.48°,18.84°,19.71°,20.23°,20.64°,22.58°,23.09°,23.60°,24.29°,24.71°,25.66°,26.61°,26....

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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 hydrochloride and its application in medicine, further relate to the crystal form of said hydrochloride and the pharmaceutical composition comprising said hydrochloride. The 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 kinase subdom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61P37/02A61P29/00A61P9/00A61P11/00A61P1/16A61P25/00A61P3/10A61P13/12A61K31/4439
CPCA61P1/16A61P3/10A61P9/00A61P11/00A61P13/12A61P25/00A61P29/00A61P37/02C07B2200/13C07D487/04
Inventor 谢德逊李权伟薛伟才刘辉戴洪果
Owner GUANGZHOU ANYANREN PHARMA TECH CO LTD
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