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Novel crystal system of irinotecan hydrochloride and preparation method thereof

A technology of irinotecan hydrochloride and crystallization, which is applied in the fields of drug combination, antitumor drugs, organic chemistry, etc., can solve the problems of high solubility of c-type crystals, low solubility of b-type crystals, and poor stability, and achieves less impurities. , High solubility, good storage stability

Active Publication Date: 2008-12-10
SHANGHAI ACEBRIGHT PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The solubility of type b crystals is small, which is not conducive to preparations
C-type crystals have high solubility, but the stability is not very good

Method used

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  • Novel crystal system of irinotecan hydrochloride and preparation method thereof
  • Novel crystal system of irinotecan hydrochloride and preparation method thereof
  • Novel crystal system of irinotecan hydrochloride and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Add 6.0 L of water to 600.0 g of raw material irinotecan hydrochloride (amorphous or type b crystal), and heat to 75° C. to completely dissolve the solid. After the solid was completely dissolved, the temperature was lowered to 22° C., and 12.0 L of acetone was gradually added under stirring. After the addition, the temperature was lowered to 5°C, and crystals were precipitated. After standing still for 12 hours, it was filtered and vacuum-dried at 35° C. for 12 hours to obtain 565.5 g of light yellow needle crystals. HPLC detection content and purity are ≥99.5%. Karl Fischer Moisture Analyzer measures 8.3% moisture.

[0036] as attached figure 1 As shown, the powder X-ray diffraction spectrum of the crystal shows: there are characteristic peaks at (2θ) 7.84°, 9.96°, 11.26°, 14.13°, 14.81°, 15.61°, 20.00°, 21.31°, 22.20°, and 22.68° .

[0037] as attached figure 2 As shown, the DSC spectrum of the crystallization shows: there is a large endothermic peak between a...

Embodiment 2

[0039] Add 50 ml of water to 6.0 g of raw material irinotecan hydrochloride (amorphous or type b crystal), and heat to 90° C. to completely dissolve the solid. After the solid was completely dissolved, the temperature was lowered to 15° C., and 150 ml of acetone was gradually added under stirring. After the addition, the temperature was lowered to 5°C, and crystals were precipitated. After standing still for 16 hours, it was filtered and vacuum-dried at 35° C. for 12 hours to obtain 5.8 g of light yellow needle crystals. The purity by HPLC was 98.5%. Karl Fischer Moisture Analyzer measures 8.1% moisture.

Embodiment 3

[0041] Add 70ml of water to 6.0g of raw material irinotecan hydrochloride (amorphous or type b crystal), and heat to 80°C to completely dissolve the solid. After the solid was completely dissolved, the temperature was lowered to 20° C., and 180 ml of acetone was gradually added under stirring. After the addition, the temperature was lowered to 0°C, and crystals were precipitated. After standing still for 15 hours, it was filtered and vacuum-dried at 35° C. for 12 hours to obtain 5.0 g of light yellow needle crystals. The purity by HPLC was 99.2%. Karl Fischer Moisture Analyzer measures 8.5% moisture.

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PUM

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Abstract

The invention discloses a new crystal of irinotecan hydrochloride. The crystal has characteristic peaks under powder X-ray diffraction at the following angles (2 theta): 7.80 degrees, 9.96 degrees, 13.28 degrees, 15.62 degrees, 19.98 degrees, 20.36 degrees, 22.34 degrees, 22.66 degrees, 26.60 degrees and 30.18 degrees. In addition, the invention also discloses a method for preparing a new crystal form of the irinotecan hydrochloride. The irinotecan hydrochloride prepared by the method has good water-solubility, good storage stability, high content and purity and less impurity.

Description

technical field [0001] The invention relates to a new crystal form of irinotecan hydrochloride; in addition, the invention also relates to a preparation method of the crystal form. Background technique [0002] Irinotecan is a camptothecin derivative jointly developed by Japan's Daiichi Seiyaku and Yakult Honsha. Since its first listing in Japan in 1994, it has attracted worldwide attention as an effective drug for metastatic colorectal cancer. Considering the water-soluble problem, its hydrochloride form (irinotecan hydrochloride trade name is called Capto) is clinically used. ), the structural formula is as follows: [0003] [0004] Document Chem.Pharm.Bull., 1991,39 (6), 1446-54. discloses a kind of synthetic method of preparing irinotecan hydrochloride trihydrate (abbreviated as CPT-11 in the document), product is to obtain from crystallization in water It is a light yellow needle-like structure or crystalline powder, and this document also discloses the crystal s...

Claims

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Application Information

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IPC IPC(8): C07D491/22
CPCA61P35/00C07D491/22
Inventor 李金亮
Owner SHANGHAI ACEBRIGHT PHARMA CO LTD
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