Platinum salts of organic acids, preparation thereof and applications in preparation of anticancer drugs

A technology of organic acid and salt products, applied in the field of medicine, can solve problems such as no reports on anti-tumor research of platinum salt derivatives

Inactive Publication Date: 2008-10-22
上海双科医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Usolic acid, asiatic acid, esculentic acid, betulic acid, lucidenic acid C are a class of triterpene acid compounds, sennoside B (sennoside B), rhein (rhein) belongs to anthraquinones, anthrone compounds, they all exist in plants, have a variety of biological activities, but they have not been reacted with metal platinum to make their platinum salt derivatives and used Reported on anti-tumor research

Method used

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  • Platinum salts of organic acids, preparation thereof and applications in preparation of anticancer drugs
  • Platinum salts of organic acids, preparation thereof and applications in preparation of anticancer drugs
  • Platinum salts of organic acids, preparation thereof and applications in preparation of anticancer drugs

Examples

Experimental program
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Effect test

Embodiment 1

[0042] The synthesis of embodiment 1, platinum ursolic acid I

[0043] 1. Weigh trans-cyclohexanediamine (549mg, 4.82mMol) and potassium chloroplatinite (2.00g, 4.82mMol) and dissolve them in 100-200ml water at room temperature and stir in the dark, and react for 5-10 hours to obtain The yellow solid was filtered and dried under reduced pressure to obtain 1.138g [Pt(C 6 h 14 N 2 ) Cl 2 ], yield 72.56%.

[0044] 2. Set [Pt(C 6 h 14 N 2 ) Cl 2 ], (1.1g, 2.9mMol) was suspended in 40-100ml of water, silver nitrate (0.986g, 5.8mMol) was added, stirred at room temperature for 112-24 days, and the formed AgCl precipitate was filtered.

[0045] 3. Mix ursolic acid (2.668g, 5.8mMol) with NaOH (232mg, 5.8mMol), add to the solution just obtained, stir at room temperature, keep away from light, overnight. 2.6 g of platinum ursolic acid I product was obtained. See above for chemical structure.

Embodiment 2

[0046] Embodiment 2, the synthesis of platinum ursolic acid II

[0047] Measure ammoniacal liquor 25ml (100mg, 5.88mMol) and potassium chloroplatinite (2.00g, 4.82mMol) and dissolve in 160ml water at room temperature and stir in the dark, react for 10 hours, then add silver nitrate (0.986g, 5.8mMol ), stirred at room temperature for one day, and the formed AgCl precipitate was removed by filtration. A mixture of ursolic acid (2.675 g, 5.8 mMol) and NaOH (230 mg, 5.8 mMol) was added to the filtrate, stirred at room temperature, protected from light, overnight. 2.3 g of platinum ursolic acid II product was obtained. See above for chemical structure.

Embodiment 3

[0048] The synthesis of embodiment 3, platinum betulinate I

[0049] 1. Weigh trans-cyclohexanediamine (549mg, 4.82mMol) and potassium chloroplatinite (2.00g, 4.82mMol) and dissolve them in 150ml of water at room temperature and stir in the dark, react for 10 hours, produce a precipitate, filter, Dry under reduced pressure to obtain 1.24g [Pt(C 6 h 14 N 2 ) Cl 2 ].

[0050] 2. Take [Pt(C 6 h 14 N 2 ) Cl 2 ], (1.1g, 2.9mMol) was suspended in 60ml of water, silver nitrate (0.99g, 5.8mMol) was added, stirred at room temperature for 24 hours, and the formed AgCl precipitate was removed by filtration. Added to the filtrate, mixed betulinic acid (2.65g, 5.8mMol) and NaOH (230mg, 5.8mMol), added to the solution just obtained, stirred at room temperature, protected from light, overnight. 2.7 g of platinum betulinate I product was obtained. See above for chemical structure.

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Abstract

The invention belongs to the field of medical technology, in particular relating to an organic acid platinum salt and the preparation method thereof and the application to the preparation of anti-cancer drugs. The invention obtains the Pt(C6H14N2)Cl2 or Pt(NH3)2Cl2 through the dissolution and reaction of trans-cyclohexanediamine or ammonia and potassium chloroplatinite in water at indoor temperature; the products of the organic platinum salt are obtained through the ways that the Pt(C6H14N2)Cl2 or the Pt(NH3)2Cl2 is suspended in water, and silver nitrate is added into the water and the Pt(C6H14N2)Cl2 or the Pt(NH3)2Cl2 reacts with the silver nitrate at indoor temperature, and the formed AgCl is precipitated, filtered and removed, and the NaOH solution of the organic acid is added into the filtrates and reacts with the filtrates overnight at indoor temperature; wherein, the organic acid is ursolic acid, asiatic acid, betulinic acid, lucidenic acid C, sennoside B or rhein, etc. The anti-tumor effect experiments on mice loading Lewis lung cancer show that the organic acid platinum salt of the invention has the significant anti-tumor effects, so the organic platinum salt can be used for preparing anti-cancer drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to platinum ursolic acid and other organic acid platinum salts, a preparation method thereof and an application in the preparation of anticancer drugs. Background technique [0002] In the past ten years, platinum-based anticancer drugs have made important progress. Nedaplatin, oxaliplatin, succiplatin and lobaplatin were successfully launched from 1995 to 2001. There are also platinum compounds still under clinical investigation, these compounds are analogs of cisplatin and carboplatin, lipophilic complexes, oral platinum(IV) complexes, multinuclear platinum complexes, and sterically hindered platinum complexes. New platinum-based anticancer drugs will in the future be generated from those compounds that have shown low toxicity, broad anticancer spectrum, and no cross-resistance with existing drugs in clinical studies. [0003] Usolic acid, asiatic acid, esculentic ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/282A61K31/56A61P35/00
Inventor 陈海生
Owner 上海双科医药科技有限公司
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