Non-solvated crystals as well as preparation method and application thereof

A non-solvated, crystal technology, applied in the direction of organic chemical methods, non-central analgesics, anti-inflammatory agents, etc., can solve the problem of not preparing non-solvated crystals, etc.

Active Publication Date: 2018-04-03
SHENZHEN CHIPSCREEN BIOSCIENCES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For the compound of formula (I), there is no me...

Method used

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  • Non-solvated crystals as well as preparation method and application thereof
  • Non-solvated crystals as well as preparation method and application thereof
  • Non-solvated crystals as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Preparation of non-solvated crystal A of N-(2-aminophenyl)-6-(7-methoxyquinoline-4-oxygen)-1-naphthylcarboxamide

[0049] Put 5.0g of N-(2-aminophenyl)-6-(7-methoxyquinoline-4-oxo)-1-naphthylcarboxamide in a 2000mL three-necked flask, add 750mL of methanol, and place in a 65°C oil bath Heat and stir until dissolved. The resulting solution was cooled and crystallized in an ice-water bath at 0°C for 4 hours, the solid was collected by filtration, and dried in vacuum at 80°C for 12 hours to obtain non-solvated crystal A. Its X-ray powder diffraction pattern is as figure 2 As shown, there are characteristic peaks at reflection angles 2θ of about 4.42°, 6.88°, 8.78°, 9.26°, 12.74°, 13.82°, 15.78°, 18.58°, 20.86°, 22.56°, 25.72°, 27.08° and 28.72° ; Its infrared spectrum is as image 3 Shown at approximately 3452, 3404, 3357, 3230, 3064, 1622, 1576, 1525, 1506, 1452, 1423, 1388, 1363, 1311, 1253, 1224, 1161, 1088 and 1024cm -1 There is a characteristic absorpt...

Embodiment 2

[0050] Example 2: Preparation of non-solvated crystal B of N-(2-aminophenyl)-6-(7-methoxyquinoline-4-oxygen)-1-naphthylcarboxamide

[0051] Put 5.0g of N-(2-aminophenyl)-6-(7-methoxyquinoline-4-oxo)-1-naphthylcarboxamide in a 2000mL three-neck flask, add 1000mL of acetonitrile, and place in an oil bath at 80°C Heat and stir until dissolved. The resulting solution was cooled and crystallized in an ice-water bath at 0°C for 4 hours, the solid was collected by filtration, and dried in vacuum at 80°C for 12 hours to obtain non-solvated crystal B. The X-ray powder diffraction pattern of the crystal is shown in Figure 5 shown. Its X-ray powder diffraction pattern has characteristic peaks at about 4.88°, 9.68°, 12.74°, 14.52°, 17.72°, 19.82°, 21.86°, 24.30°, 25.26° at reflection angle 2θ; its infrared spectrum is as follows: Image 6 As shown, at about 3423, 3352, 3238, 3030, 1624, 1597, 1531, 1502, 1452, 1423, 1388, 1365, 1308, 1255, 1226, 1159, 1086, 1022cm -1 There is a chara...

Embodiment 3

[0052] Example 3: Preparation of non-solvated crystal C of N-(2-aminophenyl)-6-(7-methoxyquinoline-4-oxygen)-1-naphthylcarboxamide

[0053] Put 1.0g N-(2-aminophenyl)-6-(7-methoxyquinoline-4-oxo)-1-naphthylcarboxamide in a 50mL three-necked flask, add 5mL dimethyl sulfoxide, and stir at room temperature until dissolved. The obtained solution was dripped into 50 mL of water under stirring, stood still for 4 hours, filtered, washed with water, collected solid, and dried in vacuum at 80° C. for 24 hours to obtain non-solvated crystal C. The X-ray powder diffraction pattern of the crystal is shown in Figure 8 As shown, its X-ray powder diffraction pattern is about 4.84°, 9.68°, 12.92°, 14.60°, 16.46°, 17.20°, 17.44°, 17.88°, 19.20°, 20.54°, 21.06°, 22.00° at reflection angle 2θ , 25.28°, and 27.66° have characteristic peaks; its infrared spectrum is as Figure 9 As shown, there are characteristic absorptions at about 3452, 3369, 3217, 3016, 2962, 1793, 1728, 1626, 1595, 1574, ...

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Abstract

The invention relates to non-solvated crystals A, B and C of N-(2-aminophenyl)-6-(7-methoxyquinoline-4-oxo)-1-naphthalene amide and a preparation method of non-solvated crystals A, B and C, also relates to pharmaceutical composition containing the crystals and an application of the crystals in preparation of a drug for treating diseases related to abnormal activities of protein kinase or abnormalactivities of histone deacetylase.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to non-solvated crystals of N-(2-aminophenyl)-6-(7-methoxyquinoline-4-oxygen)-1-naphthylcarboxamide and a preparation method thereof and application. Background technique [0002] N-(2-aminophenyl)-6-(7-methoxyquinoline-4-oxo)-1-naphthylcarboxamide is a dual-target inhibitor of protein kinase and histone deacetylase. The chemical structure is shown in structural formula (I). [0003] [0004] In the Chinese patent application CN200910223861.5, the pharmacological activity of the compound of formula (I) is described. This compound has protein kinase inhibitory activity and histone deacetylase inhibitory activity, and can be used for the treatment of abnormal protein kinase activity and histone deacetylation Diseases associated with abnormal enzyme activity, including inflammation, autoimmune diseases, cancer, neurological and neurodegenerative diseases, cardiovascular diseases...

Claims

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Application Information

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IPC IPC(8): C07D215/233A61K31/47A61P29/00A61P37/06A61P35/00A61P25/00A61P25/28A61P9/00A61P3/00A61P37/08A61P11/06A61P35/02
CPCC07D215/233C07B2200/13A61K31/47A61P37/06A61P37/08A61P3/00A61P9/00A61P11/06A61P25/00A61P25/28A61P29/00A61P35/00A61P35/02A61K9/2009A61K9/2027A61K9/2054A61K9/2059A61K9/4858A61K9/4866
Inventor 鲁先平李志斌
Owner SHENZHEN CHIPSCREEN BIOSCIENCES CO LTD
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