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7-ethyl-10-hydroxycamptothecine crystal forms, and preparation method and application thereof

A technology of hydroxycamptothecin and crystal form, applied in the field of medicinal chemistry, can solve the problem of low solubility of polymorphs

Active Publication Date: 2015-04-29
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the polymorphic form of 7-ethyl-10-hydroxycamptothecin is not very soluble

Method used

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  • 7-ethyl-10-hydroxycamptothecine crystal forms, and preparation method and application thereof
  • 7-ethyl-10-hydroxycamptothecine crystal forms, and preparation method and application thereof
  • 7-ethyl-10-hydroxycamptothecine crystal forms, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Examples 1-5 are the preparation of crystalline form II of 7-ethyl-10-hydroxycamptothecin, and examples 6-10 are the preparation of crystalline form III of 7-ethyl-10-hydroxycamptothecin.

[0058] Embodiment 1, the preparation of 7-ethyl-10-hydroxycamptothecin crystal form II

[0059] Weigh 50mg of 7-ethyl-10-hydroxycamptothecin into a reaction bottle, add 20ml of a mixed solvent of methanol: chloroform with a volume ratio of 1:1, stir to dissolve, evaporate the solvent at 10-20°C, and separate by filtration Solid, the solid was vacuum-dried at 50°C to constant weight to obtain 7-ethyl-10-hydroxycamptothecin crystal form II.

Embodiment 2

[0060] Example 2, Preparation of 7-ethyl-10-hydroxycamptothecin crystal form II

[0061] Weigh 30mg of 7-ethyl-10-hydroxycamptothecin into a reaction flask, add 210ml of methanol solvent, stir to dissolve, evaporate the solvent at 10-20°C, filter and separate the solid, and dry the solid in vacuum at 50°C until constant Weight, that is, 7-ethyl-10-hydroxycamptothecin crystal form II.

Embodiment 3

[0062] Example 3, Preparation of 7-ethyl-10-hydroxycamptothecin crystal form II

[0063] Weigh 50mg of 7-ethyl-10-hydroxycamptothecin into a reaction flask, add 12ml of methanol:chloroform mixed solvent with a volume ratio of 1:1, stir at room temperature, filter and separate the solid, and dry the solid under vacuum at 50°C To constant weight, the crystal form II of 7-ethyl-10-hydroxycamptothecin was obtained.

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Abstract

The invention relates to 7-ethyl-10-hydroxycamptothecine crystal forms II and III, and a preparation method and application thereof. The crystal form II uses Cu-K alpha radiation; the X-ray powder diffraction represented by 2theta angle has characteristic peaks when the diffraction angle is 5.64, 10.80, 12.55, 13.48, 17.09, 17.65, 18.21, 18.79, 24.52 and 26.84 degrees; and the error range of 2theta is + / -0.2 degree. The crystal form III uses Cu-K alpha radiation; the X-ray powder diffraction represented by 2theta angle has characteristic peaks when the diffraction angle is 4.58, 9.34, 10.42, 11.12, 12.30, 13.40, 14.40, 16.34, 16.86, 17.20, 17.70, 18.72, 19.32, 21.48, 22.44, 24.90, 25.40, 25.68 and 27.44 degrees; and the error range of 2theta is + / -0.2 degree. The two crystal forms of 7-ethyl-10-hydroxycamptothecine have high solubility and favorable stability.

Description

technical field [0001] The invention relates to two new crystal forms of 7-ethyl-10 hydroxycamptothecin and a preparation method thereof, belonging to the technical field of medicinal chemistry. Background technique [0002] Irinotecan (mnotecan, CPT-11) is a semi-synthetic water-soluble derivative of camptothecin. Its antitumor activity is higher than that of camptothecin, and its side effects are lower than that of camptothecin. The anti-tumor mechanism of irinotecan is mainly to inhibit the activity of topoisomerase-I, which affects DNA replication and leads to cell death. CPT-11 is an important drug for the treatment of small-cell lung cancer (SCLC). In 2010, the National Comprehensive Cancer Network (NCCN) in the United States recommended CPT-11 as the first-line treatment for advanced SCLC. It can also be used in second-line therapy. Irinotecan is an ester prodrug, which is mainly metabolized by carboxylesterase into 7-ethyl-10-hydroxycamptothecin (SN-38) with better...

Claims

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Application Information

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IPC IPC(8): C07D491/22A61K31/4745A61P35/00
CPCC07D491/22
Inventor 王蕾房兰陶绪堂仵泽鑫
Owner SHANDONG UNIV
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