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Methods of preparing and purifying 9-nitro-20-camptothecin and 9-nitro-20-camptothecin and its compositions

A technology of nitrocamptothecin and camptothecin, which is applied in the directions of pharmaceutical combinations, pharmaceutical formulations, and medical preparations containing active ingredients, etc., can solve the problem of low 9NC yield, reduced 9NC yield, time-consuming and high cost, etc. question

Inactive Publication Date: 2008-05-28
THE STEHLIN FOUND FOR CANCER RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the yield of 9NC is low and there are many by-products, the method for separating and purifying 9NC is time-consuming and expensive, and may further reduce the yield of 9NC

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Camptothecin and KNO in acetic acid 3 Reaction

[0076] 0.50g (0.0014mol) 20(S)-camptothecin and 0.50g KNO 3 (0.0050 mol) was added to 30 ml of acetic acid in a 100 ml round bottom flask equipped with a magnetic stirrer. The mixture was stirred at room temperature for 24 hours and poured in portions with stirring into 500 ml of ice water. The suspension was extracted 3 times with 200ml of dichloromethane (200ml×3). The combined extracts were dried over 20 g of anhydrous sodium sulfate for 6 hours. After separation of dichloromethane with a rotary evaporator, the residue was refluxed in petroleum ether for 4 hours. The product was obtained as an off-white powder after filtration and air drying for 4 hours. HPLC analysis showed no camptothecin and KNO in acetic acid 3Indication of nitration. 100% recovery of starting camptothecin (Table 1)

Embodiment 2

[0078] Camptothecin and KNO in acetic anhydride 3 Reaction

[0079] Camptothecin was nitrated and treated in the same manner as in the reaction in Example 1. HPLC analysis of the reaction product indicated 100% recovery of the starting camptothecin.

Embodiment 3

[0081] Camptothecin and KNO in trifluoroacetic anhydride 3 Reaction

[0082] Camptothecin was nitrated and treated in the same manner as in Example 1. The HPLC analysis data of the reaction mixture are shown in Table 1.

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PUM

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Abstract

A method is disclosed for the preparation of 9-nitrocamptothecin which involves reacting 20-camptothecin with at least one inorganic nitrate salt and at least one acid effective in catalyzing the formation of a nitronium ion, where the reaction occurs at a temperature and for a time sufficient to form the 9-nitrocamptothecin. Also, methods of further purifying the 9-nitrocamptothecin by column chromatography or by reprecipatation is also disclosed.

Description

[0001] This divisional application is the corresponding international application with the application number "98807978.X" and the title of the invention "Method for Purifying and Preparing-9-Nitro-20-Camptothecin" filed on July 10, 1998 A divisional application of PCT / US98 / 14532 and International Publication No. WO99 / 07709 patent application for invention. technical field [0002] The present invention relates to a method for preparing and purifying 9-nitro-20-camptothecin (9NC), 9-nitro-20-camptothecin and its composition. Background technique [0003] 9-nitro-20(S)-camptothecin has shown promise in the treatment of certain types of cancer. This water-insoluble 9-nitro-20(S)-camptothecin has been studied in vivo and in vitro and 9-nitro-20(S)-camptothecin is used in clinical trials for certain cancers . [0004] Japanese Published Patent Application No. 59-51288 provides a method for preparing 9-nitrocamptothecin by treating camptothecin with a slight excess of concentra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/22A61K31/4745A61P35/00A61K31/4375C07D491/147
CPCC07D491/22A61P35/00
Inventor 曹志松
Owner THE STEHLIN FOUND FOR CANCER RES
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