Method for preparation of dual-dicarboxylic acid diamine lobaplatin (II) derivative by one-pot method

A bis-dicarboxylic acid and dicarboxylic acid technology, which is applied in the field of one-pot preparation of supramolecular platinum-based anti-tumor drug bicycloplatinum, can solve the problems of increased purification difficulty, impossibility of subsequent reaction, and influence, and achieve stable product quality , short production cycle and low energy consumption

Pending Publication Date: 2018-09-11
KUNMING GUIYAN PHARMA
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Problems solved by technology

However, due to the difference in reaction conditions between each step reaction and the incompletely reacted raw materials and generated impurities in the previous step reaction, the latter step reaction may be affected, and in serious cases, the latter step reaction cannot be carried out. At the same time, the impurity Accumulation also makes purification more difficult in the final purification step, which is why most reactions require separation and purification of intermediates

Method used

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  • Method for preparation of dual-dicarboxylic acid diamine lobaplatin (II) derivative by one-pot method
  • Method for preparation of dual-dicarboxylic acid diamine lobaplatin (II) derivative by one-pot method
  • Method for preparation of dual-dicarboxylic acid diamine lobaplatin (II) derivative by one-pot method

Examples

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Effect test

Embodiment 1

[0121] Take 10.0 g (20.7 mmol) of cis-diiododiammine platinum (II), add 350 ml of purified water, stir evenly and heat to 80°C in a water bath, then add 7.2 g of silver 1,1-cyclobutanedicarboxylate ( 20.1 mmol), reacted for 30 minutes, cooled to 16°C and filtered off the AgI residue, and heated the filtrate to 70°C in a water bath. Add 32.0 g (222.2 mmol) of 1,1-cyclobutanedicarboxylic acid, stir rapidly for 30 minutes, then concentrate under reduced pressure to about 70 ml of remaining liquid, cool to 10°C, filter the precipitated solid, and dry at 60°C to obtain the product 5.43 grams, yield 50.94%, content 100.18%. The obtained product was characterized by elemental analysis, negative ion electrospray mass spectrometry, nuclear magnetic resonance-hydrogen spectrum, nuclear magnetic resonance-carbon spectrum, and X-ray diffraction, and the content of bicycloplatinum was measured by high performance liquid chromatography.

[0122] The result is as follows:

[0123] 1. Eleme...

Embodiment 2

[0142] Example 2 was prepared according to the same method as Example 1, except that 2.98 g (20.7 mmol) of 1,1-cyclobutanedicarboxylic acid was added. As a result, 4.42 g of bicycloplatinum was obtained, with a yield of 41.46% and a content of 101.93%. Negative ion electrospray mass spectrum: 514 (M-1); X-ray diffraction patterns such as Figure 4 shown.

Embodiment 3

[0144] Example 3 was prepared in the same manner as in Example 1, except that 59.6 g (413.9 mmol) of 1,1-cyclobutanedicarboxylic acid was added. As a result, 5.38 g of bicycloplatinum was obtained, with a yield of 50.47% and a content of 98.06%. Negative ion electrospray mass spectrum: 514 (M-1); X-ray diffraction patterns such as Figure 5 shown.

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Abstract

The present invention provides a method for preparation of dual-dicarboxylic acid diamine lobaplatin (II) derivative by one-pot method which does not include the separation of the intermediate carboplatin or carboplatin analog. Compared with the prior art, according to the present invention, the method can directly continue the reaction with the dicarboxylic acid to obtain the dicarboxylic acid after the reaction to form the carboplatin or the carboplatin analog without processing the pure product of the carboplatin or the carboplatin analog. The diammonium platinum (II) derivative, the wholeprocess only needs to undergo a process of distillation and water removal, the overall energy consumption is low, the production cycle is short, and the single batch production cycle can be controlledwithin 2 days. Water alone is used as a solvent, which is environmentally friendly and produces less waste. The obtained product has high purity and does not require further purification treatment, and the product quality is stable.

Description

technical field [0001] The present invention relates to the synthesis field of platinum-based antineoplastic drugs, specifically, the present invention relates to a one-pot method for preparing supramolecular platinum-based antineoplastic drug diammine platinum (II) derivatives, in particular, the present invention The invention relates to a method for preparing supramolecular platinum-based antitumor drug bicycloplatin in a one-pot method. Background technique [0002] Since the U.S. FDA approved cisplatin as an anticancer drug in 1978, the mortality rate of testicular cancer patients has been reduced from 100% to less than 10%, and the cure rate can reach 100% for early detection patients, making cisplatin a Outstanding representatives of anticancer drugs. In 1986, the FDA approved the marketing of the second-generation platinum anticancer drug carboplatin. Its anticancer spectrum is similar to that of cisplatin, but it has good water solubility and mild side effects. In...

Claims

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Application Information

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IPC IPC(8): C07F15/00G01N30/88G01N23/207G01N23/205
CPCG01N23/2055G01N23/207G01N30/88C07F15/0093G01N2030/8809C07B2200/13G01N2030/884A61K31/555A61P35/00
Inventor 杨旭清普绍平丛艳伟刘其星王应飞彭娟
Owner KUNMING GUIYAN PHARMA
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