10-hydroxy camptothecin arginine salt, and its preparing method and use

A technology of hydroxycamptothecin and arginine salt, which can be used in pharmaceutical formulations, medical preparations containing active ingredients, and pill delivery, etc., can solve problems such as poor solubility, discoloration of solutions, and restricted use, and achieve tumor suppression. Strong activity, strong anti-tumor activity, and safe clinical application

Inactive Publication Date: 2007-06-13
成都三康药物研究所
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its preparation itself, its physical and chemical properties are unstable, easy to oxidize, the toxicity increases after oxidation, and the solution changes color, which affects the curative effect.
And the solubility of 10-hydroxycamptothecin in commonly used solvents such as chloroform, ethanol, methanol, water is all bad, limits its use

Method used

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  • 10-hydroxy camptothecin arginine salt, and its preparing method and use
  • 10-hydroxy camptothecin arginine salt, and its preparing method and use
  • 10-hydroxy camptothecin arginine salt, and its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1 Preparation of 10-hydroxycamptothecin arginine salt (n=1) of the present invention

[0026] Take 728 mg of 10-hydroxycamptothecin and add 100 ml of dimethyl sulfoxide, heat in a water bath to dissolve, add 348 mg of L-arginine under reflux and stirring, continue to reflux until the solution is clear, and recover dimethyl sulfoxide under reduced pressure. Add 25ml of methanol to the dried product, heat to reflux to dissolve, filter, add 250ml of acetone to the filtrate, let it stand, protect from light, filter, and dry the precipitate at 60°C under reduced pressure to obtain a yellow powder precipitate.

[0027] The resulting product has been subjected to the following structural analysis and identification tests:

[0028] Scanning within the wavelength range of 200-500nm, there are maximum absorptions at 210, 266, 367, and 383nm wavelengths, mainly due to the conjugated absorption of hydroxycamptothecin aromatic heterocycles.

[0029] Infrared absorption s...

Embodiment 2

[0042] Embodiment 2 Preparation of 10-hydroxycamptothecin arginine salt (n=6) of the present invention

[0043] Take 240mg and 1.70g of L-arginine respectively, add 100ml of dimethyl sulfoxide, heat in a water bath to dissolve, add 500mg of 10-hydroxycamptothecin under reflux and stirring, continue to reflux until the solution is clear, and recover under reduced pressure Dimethyl sulfoxide, add 25ml of methanol to the dried product and heat to reflux to dissolve, filter, add 250ml of acetone to the filtrate, let stand, protect from light, filter, and dry the precipitate at 60°C under reduced pressure to obtain a yellow powder precipitate. The ninhydrin reaction of this product was positive, and the retention time of HPLC was inconsistent with that of hydroxycamptothecin. The acidic mobile phase was used for analysis, and a peak with a retention time consistent with that of hydroxycamptothecin appeared. There are arginine spots in TLC examination under acidic conditions, that ...

Embodiment 3

[0044] Example 3 Preparation of 10-hydroxycamptothecin arginine salt injection

[0045] R x1 : 100ml: 50mg

[0046] Hydroxycamptothecin arginine salt 0.5g (prepared by embodiment 1)

[0047] Sodium chloride 8.5g

[0048] 0.1M sodium hydroxide appropriate amount

[0049] Water for injection 1000ml

[0050] Take by weighing the hydroxycamptothecin arginine salt of the prescription amount, add 500ml of water for injection to dissolve, add 8.5g of sodium chloride, stir to dissolve, adjust the pH to 9.2 with 0.1M sodium hydroxide, add 1000ml of water for injection, filter, Ready to serve.

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Abstract

This invention relates to 10-hydroxycamptothecin arginine salt like the structure of formula (I). The preparation of this compound is in anhydrous solvent. 10-hydroxycamptothecin arginine reacts with arginine, obtaining related arginine salt and its compound. The quantity of adding arginine can be from 1 to 10 times of molar ratio. The water solubility of 10-hydroxycamptothecin arginine salt and its association object is obviously better than 10-hydroxycamptothecin, and possessing conspicuous liver target. It overcomes flaws such as noxious property of camptothecin sodium is high, stability is bad. It provides a medicine of which curative effect is reliable, medication is safe and cost is low for tumor patient.

Description

technical field [0001] The invention relates to a 10-hydroxycamptothecin arginine salt, a preparation method and application thereof, and belongs to the field of medicine and chemical industry. Background technique [0002] In 1966, American scholar Wall et al. extracted camptothecin from the unique tree species Campptotheca acuminata in my country, and found that it has a unique anticancer effect, but the side effects are large, which limits the clinical application of camptothecin. Therefore, camptothecin derivatives that not only maintain the anticancer activity of camptothecin but also have lower toxicity have always been the focus of attention. Subsequently, 10-hydroxycamptothecin (HCPT) was isolated from camptothecin, and clinical trials showed that it has a wide anti-cancer spectrum, significant curative effect, and less toxic and side effects, especially for primary liver cancer, Gastrointestinal cancer bladder cancer, head and neck skin cancer, leukemia, cervical c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/22A61P35/00A61K31/437A61K9/20A61K9/08A61K9/48A61K9/19
Inventor 吴四灵王小林
Owner 成都三康药物研究所
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