Crystalline nitroxquinoline, and preparation method and application thereof

A nitroxoline and crystallization technology is applied in the field of crystalline nitroxoline and its preparation, and can solve the problems that there is no research and report on nitroxoline crystal forms.

Pending Publication Date: 2021-06-29
JIANGSU YAHONG MEDITECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, there is no research and r

Method used

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  • Crystalline nitroxquinoline, and preparation method and application thereof
  • Crystalline nitroxquinoline, and preparation method and application thereof
  • Crystalline nitroxquinoline, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] The preparation example one of the A-type crystal of embodiment 1 nitroxyquinoline

[0101] Weigh 50 mg of nitroquinol, and gradually add methanol (6 mL) at 50° C. until the nitroquinol is completely dissolved into a clear solution. Then, the solution was lowered to room temperature, stirred for 0.5 h, centrifuged (Eppendof Centrifuge 5415, 4000 r / min, 5 min) to separate and collect the wet solid, and dried under reduced pressure at 40 ° C to obtain about 40 mg of yellow long needle-shaped solid, yield: 80%.

[0102] The X-ray powder diffraction pattern of gained solid sees figure 1 , the X-ray powder diffraction data are shown in Table 1 below, and are defined as type A crystals.

[0103] Table 1 XRPD peak and intensity list of Form A

[0104]

[0105]

[0106] Weigh about 5 mg of the crystalline sample into a crucible, under nitrogen protection, heat up from 30°C to 250°C at a heating rate of 20°C / min, and hold at 250°C for 1 minute. Its TGA spectrum is show...

Embodiment 2A preparation example 2

[0109]Weigh 50 mg of nitroquinol, and gradually add acetonitrile (2.5 mL) at 60° C. until the nitroquinol is completely dissolved into a clear solution. Then, the solution was lowered to -20°C, stirred for 0.5h, centrifuged (Eppendof Centrifuge 5415, 4000r / min, 5min) to separate and collect the wet solid, and dried under reduced pressure at 40°C to obtain about 35mg of yellow long needle-like solid, which was collected Rate: 70%.

[0110] Its XRPD patterns are researched and compared, and it is confirmed that the product is type A crystal.

Embodiment 3

[0111] The preparation example three of the A-type crystal of embodiment 3 nitroxyquinoline

[0112] Weigh 50 mg of nitroquinol, and gradually add isopropanol (15 mL) at 55° C. until the nitroquinol is completely dissolved into a clear solution. Then, the solution was lowered to -20°C, stirred for 0.5h, centrifuged (Eppendof Centrifuge 5415, 4000r / min, 5min) to separate and collect the wet solid, and dried under reduced pressure at 40°C to obtain about 35mg of a yellow solid, yield: 70 %.

[0113] Its XRPD patterns are researched and compared, and it is confirmed that the product is type A crystal.

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PUM

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Abstract

The invention discloses a crystalline nitroxquinoline, and a preparation method and application thereof. An X-ray powder diffraction pattern of the crystalline nitroxquinoline comprises characteristic peaks at 2theta diffraction angles of 11.3 +/-0.2 DEG, 12.9 +/-0.2 DEG, 16.9 +/-0.2 DEG, 19.7 +/-0.2 DEG, 22.1 +/- 0.2 DEG, 23.7 +/-0.2 DEG, 24.2 +/-0.2 DEG, 25.9 +/-0.2 DEG, 27.1 +/-0.2 DEG and 28.0 +/-0.2 DEG. The crystalline nitrooxquinoline has no hygroscopicity and good stability, so that the selection of administration routes and the optimization of a pharmaceutical preparation process are facilitated, the production quality of drugs is improved, and the action effect of the drugs is improved.

Description

technical field [0001] The present invention relates to crystalline nitroxyquinoline and its preparation method and application. Background technique [0002] Nitroxoline, whose chemical name is 5-nitro-8-hydroxyquinoline, was developed as an oral antibiotic drug in the 1960s, mainly for urinary system infections, and has a relatively safe history of use. The discovery and use of new antibiotics have been replaced. In recent years, new studies have found that nitroquinoline can simultaneously inhibit methionine aminopeptidase MetAP2 and silent information regulator 2-related enzymes SIRT1 in vascular endothelial cells, exerting a synergistic inhibitory effect on tumor angiogenesis, and at the same time Inhibits the proliferation of tumor cells. Therefore, nitroquinoline has been redeveloped for the treatment of tumors including bladder cancer. [0003] The polymorphic form of drugs has become an essential and important part of drug development and drug quality control. T...

Claims

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Application Information

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IPC IPC(8): C07D215/28A61K31/47A61P35/00
CPCC07D215/28A61P35/00C07B2200/13
Inventor 刘江华郭玉申
Owner JIANGSU YAHONG MEDITECH CO LTD
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