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Crystal form of alkynyl-containing compound salt, preparation method and application thereof

A crystal form, ethynyl technology, applied in the preparation of organic compounds, separation/purification of carboxylic acid compounds, preparation of carboxylate, etc., can solve the problems of polycrystalline compounds and achieve good stability

Active Publication Date: 2020-10-02
GUANGZHOU SHUNJIAN PHARM CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Known compounds generally have polymorphism, and general drugs may have two or more different crystalline states

Method used

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  • Crystal form of alkynyl-containing compound salt, preparation method and application thereof
  • Crystal form of alkynyl-containing compound salt, preparation method and application thereof
  • Crystal form of alkynyl-containing compound salt, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Example 1: Preparation of Form II

[0080] 40mg 3-((1H-pyrazole[3,4-b]pyridine-5-substituted)ethynyl)-4-methyl-N-(4-((4-methylpiperazine-1-substituted) (Methyl)-3-(trifluoromethyl)phenyl)benzamide was added to 0.5mL of methanol and dichloromethane (the volume ratio of methanol and dichloromethane is 1:1), stirred at room temperature, and 1 equivalent was added. Maric acid immediately appeared as a solid, continue to stir overnight, filter, and vacuum dry at 50°C overnight to obtain crystal form II. The XPRD pattern of Form II is as follows figure 1 Shown. In the X-ray powder diffraction pattern expressed in 2θ angles, the 2θ values ​​are shown in Table 1;

[0081] Table 1

[0082] Diffraction angle Relative Strength d valueDiffraction angle Relative Strength d value (2θ°)(％) (Angstrom) (2θ°)(％) (Angstrom) 4.46141.419.7933324.3527.13.6525 8.904209.92424.65248.13.60846 11.81780.67.4831725.19848.23.5315 12.24424.37.2232425.8825.73.43995 13.25145.86.6764526.30126.83.38583...

Embodiment 2

[0085] Example 2: 3-((1H-pyrazole[3,4-b]pyridine-5-substituted)ethynyl)-4-methyl-N-(4-((4-methylpiperazine-1- (Substituted)methyl)-3-(trifluoromethyl)phenyl)benzamide monohydrochloride form III

[0086] 40mg of 3-((1H-pyrazole[3,4-b]pyridine-5-substituted)ethynyl)-4-methyl-N-(4-((4-methylpiperazine-1-substituted)methyl (Methyl)-3-(trifluoromethyl)phenyl)benzamide was added to 0.2mL of methanol and dichloromethane (the volume ratio of methanol to dichloromethane is 1:1), mixed into the system, stirred at room temperature, and 1.05 equivalent was added The hydrochloric acid, the solid was completely dissolved, ethyl acetate was added, the stirring was continued for 0.5 h, the solid was precipitated, the stirring was continued for 4 h, filtered, and dried under vacuum at 50° C. overnight to obtain crystal form III.

[0087] The X-ray powder diffraction pattern of Form III expressed at 2θ angles, the 2θ values ​​are shown in Table 2;

[0088] Table 2 2θ Values ​​of Form III

[0089] ...

Embodiment 3

[0092] Example 3: Preparation of Form IV

[0093] 40mg of 3-((1H-pyrazole[3,4-b]pyridine-5-substituted)ethynyl)-4-methyl-N-(4-((4-methylpiperazine-1-substituted)methyl Base)-3-(trifluoromethyl)phenyl)benzamide was added to 0.4mL of methanol and dichloromethane (the volume ratio of methanol to dichloromethane is 1:1), mixed into the system, stirred at room temperature, and 2.1 equivalents were added The hydrochloric acid, a solid precipitated out, continued to stir for 1-2h, filtered, and dried under vacuum at 50°C overnight to obtain crystal form IV.

[0094] In the X-ray powder diffraction diagram of Form IV expressed at 2θ angles, the 2θ values ​​are shown in Table 3;

[0095] Table 3 2θ Values ​​of Form IV

[0096] Diffraction angle Relative Strength d valueDiffraction angle Relative Strength d value (2θ°)(％) (Angstrom) (2θ°)(％) (Angstrom) 4.29310020.5655316.62956.35.3268 5.14779.217.1562116.79758.55.27394 6.24287.414.1490617.22479.75.14416 9.02141.59.7952218.50148.84.79187 1...

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PUM

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Abstract

The invention discloses a crystal form of alkynyl-containing compound salt and a preparation method and application of the crystal form. The invention specifically discloses a crystal form II of 3-((1H-pyrazole [3, 4-b] pyridine-5-substituted) ethynyl)-4-methyl-N-(4-((4-methylpiperazine-1-substituted) methyl)-3-(trifluoromethyl) phenyl) benzamide fumarate. The crystal form provided by the invention has good stability, and has important value for optimization and development of drugs.

Description

Technical field [0001] The invention belongs to the field of chemical medicine, and particularly relates to a crystal form, preparation method and application of a salt of an alkynyl group-containing compound. Background technique [0002] This application relates to an alkynyl-containing compound with a chemical name of 3-((1H-pyrazole[3,4-b]pyridine-5-substituted)ethynyl)-4-methyl-N-(4-(( 4-methylpiperazine-1-substituted)methyl)-3-(trifluoromethyl)phenyl)benzamide, the patent reports on this compound are very limited, and the crystal form of the above compound is not involved. [0003] Known compounds generally have polymorphism, and general drugs may have two or more different crystalline substance states. The existence form and quantity of polymorphic compounds are unpredictable. Different crystal forms of the same drug have significant differences in solubility, melting point, density, stability, etc., which affect the temperature, uniformity, and biological characteristics o...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07C51/41C07C51/43C07C57/15A61K31/496A61P35/00
CPCA61P35/00C07B2200/09C07B2200/13C07C51/412C07C51/43C07C57/15C07D471/04
Inventor 温剑锋林艳琼冯建鹏吴天助邵振中李卫东
Owner GUANGZHOU SHUNJIAN PHARM CO LTD
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