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

A technology of hydroxycamptothecin and arginine salt, which is applied in the field of medicine and chemical industry, can solve problems such as poor solubility, solution discoloration, and limited use, and achieve strong anti-tumor activity, strong anti-tumor activity, and safe clinical application Effect

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

[0023] Example 1 Preparation of 10-hydroxycamptothecin arginine salt (n=1)

[0024] Take 465mg of arginine, add 100ml of water, stir to dissolve, add another 971mg of 10-hydroxycamptothecin to the arginine solution, stir to dissolve, add 2000ml of isopropanol, mix well, place at 4°C for 12h, pour The supernatant and the pellet were washed twice with 95% isopropanol and dried. Add 50ml of methanol to the dried product to dissolve, add ether to the filtrate until no precipitate precipitates, let it stand in the dark for 2 hours, pour off the supernatant, wash the precipitate with ether three times, and dry it.

[0025] The obtained product has carried out the following structural analysis identification test:

[0026] Ultraviolet Absorption Spectrum: Use methanol as the test solvent to prepare a 25μg / ml solution, use TU-1800spc instrument to scan in the wavelength range of 200-500nm, and have maximum absorption at 210, 266, 367, and 383nm wavelengths.

[0027] Infrared absorpt...

Embodiment 2

[0039] Example 2 Preparation of 10-hydroxycamptothecin arginine salt (n=8,7,6)

[0040] Take 3.71g, 3.25g, and 2.78g of arginine respectively, add 100ml of water, stir to dissolve, take another 971mg of 10-hydroxycamptothecin, add to the arginine solution, stir to dissolve, add 2000ml of isopropanol, mix Evenly, place at 4°C in the dark for 12 hours, pour off the supernatant, wash the precipitate twice with 95% isopropanol, and dry. Add 50ml of methanol to the dried product to dissolve, add ether to the filtrate until no precipitate precipitates, let it stand for 2 hours, pour off the supernatant, wash the precipitate with ether three times, and dry it.

[0041] The obtained 3 products ninhydrin reacted positively, and precipitated out after adding acid. soluble in water. HPLC analysis shows that 10-hydroxycamptothecin arginine salt and hydroxycamptothecin have different retention times under neutral mobile phase; under acidic conditions, the lactone ring of 10-hydroxycampto...

Embodiment 3

[0042] Example 3 Preparation of 10-hydroxycamptothecin arginine salt injection

[0043] R x1 : 100ml: 50mg

[0044] Hydroxycamptothecin arginine salt 0.5 (prepared by embodiment 1)

[0045] Sodium chloride 8.5g

[0046] Water for injection 1000ml

[0047] Weigh the prescribed amount of hydroxycamptothecin arginine salt, add 500ml of water for injection to dissolve, add 8.5g of sodium chloride, stir to dissolve, add water for injection to 1000ml, filter, and pack.

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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 condition of water participating. 10-hydroxycamptothecin lactone is unfolded, of which carboxy group first bonds with amino-group of arginine to produce salt, then bonds with 10-phenolic hydroxyl group, then bonds with other arginine acid by hydrogen bond pattern. The quantity of adding arginine can be from 1 to 8 times of molar ratio. The water solubility of 10-hydroxycamptothecin arginine salt and its association object is obviously better than 10-hydroxycamptothecin. 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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IPC IPC(8): C07D471/14C07D491/22A61P35/00A61K31/437A61K9/20A61K9/08A61K9/48A61K9/19
Inventor 吴四灵王小林
Owner 成都三康药物研究所
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