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Preparation method of supramolecular anti-cancer drug (dicycloplatin)

An anticancer drug, bicycloplatinum technology, applied in the field of preparation of supramolecular anticancer drug bicycloplatinum, can solve the problems of easy destruction of hydrogen bonds, inappropriate distilled water post-treatment steps, low yield and the like, and achieves simplified determination process and conditions. Gentle, high-yield effect

Inactive Publication Date: 2015-06-10
ZHUYUE TONGDA MEDICAL TECH DEV SUZHOU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method has some disadvantages: for example, the structure of bicycloplatin is quite special, which is a supramolecular combination of carboplatin and 1,1 cyclobutanedicarboxylic acid through four hydrogen bonds, and the stirring step and rotary evaporation step are easy to destroy the bicycloplatinum. Hydrogen bonding in platinum, which will result in lower yields
In addition, bicycloplatinum is soluble in water, and the post-treatment step of recrystallization from distilled water is not suitable

Method used

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  • Preparation method of supramolecular anti-cancer drug (dicycloplatin)
  • Preparation method of supramolecular anti-cancer drug (dicycloplatin)
  • Preparation method of supramolecular anti-cancer drug (dicycloplatin)

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Add 37.1g (0.1mol) of carboplatin and 14.4g (0.1mol) of 1,1-cyclobutanedicarboxylic acid into 1855mL (50 times the amount) of water for injection, and stir at room temperature (about 25°C) for about 1 hour to The solids were all dissolved, and then left to stand in the dark at room temperature for 7 days; concentrated under reduced pressure at 40°C, and dried to obtain 51.5 g of bicycloplatinum qualified for inspection, with an HPLC purity of 99.95% and a yield of 100% ( 1 H-NMR see Figure 4 , see ESI Figure 5 , XRPD spectrum see Image 6 , the XRPD spectrum of carboplatin is shown in Figure 7 ).

[0043] Figure 4 bicycloplatin in 1 H-NMR analysis is as follows:

[0044] 1.816-1.736ppm, 5-fold peak, coupling constant J=8Hz, 2 H, which is the 3-position CH on the left four-membered ring in structural formula (I) 2 of 2 H atoms.

[0045] 1.928-1.848ppm, 5-fold peak, coupling constant J=8Hz, 2 H, is the 3-position CH of the right four-membered ring in structura...

Embodiment 2

[0058] Add 37.1g (0.1mol) of carboplatin and 14.4g (0.1mol) of 1,1-cyclobutanedicarboxylic acid into 1855mL (50 times the amount) of water for injection, and stir at about 15°C for about 2 hours until all the solids are Dissolved, and then stood in the dark at 15° C. for 9 days; concentrated under reduced pressure at 50° C., dried to obtain 50.5 g of fully qualified bicycloplatinum, HPLC purity 99.90%, and yield 98% (see ESI spectrogram Figure 8 ).

Embodiment 3

[0060] Add 37.1g (0.1mol) of carboplatin and 14.4g (0.1mol) of 1,1-cyclobutanedicarboxylic acid into 1855mL (50 times the amount) of water for injection, and stir at about 40°C for about 1 hour until all the solids are Dissolved, and then stood in the dark at 40°C for 6 days; concentrated under reduced pressure at 30°C, and dried to obtain 51.5g of fully qualified bicycloplatinum, with an HPLC purity of 99.96% and a yield of 100% (see ESI spectrogram Figure 9 ).

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Abstract

The invention provides a preparation method of a supramolecular anti-cancer drug (dicycloplatin). The preparation method comprises the following steps of: adding carboplatin and 1,1-cyclobutanedicarboxylic acid into water according to the mol ratio of 1:1, dissolving and uniformly mixing to obtain the mixed solution, and standing the mixed solution in a dark place at the temperature of more than 0 DEG C and less than or equal to 60 DEG C for 3-9 days, and concentrating under reduced pressure or freeze-drying so as to obtain dicycloplatin. The preparation method disclosed by the invention is moderate in condition and environment friendly; both the yield and the purity of dicycloplatin can be up to nearly 100%; the batch yield can reach 1000g; and thus, the preparation method is particularly applied to industrial production.

Description

technical field [0001] The invention relates to the field of medicine preparation, and more particularly relates to a preparation method of supramolecular anticancer drug bicycloplatinum. Background technique [0002] In 1969, Barnett Rosenberg discovered cisplatin (cis-[PtC 1 2 (NH 3 ) 2 ]) have anticancer activity. In 1978, cisplatin was approved by the FDA as an anticancer drug and was launched in the United States, and it has been used to treat various human cancers for decades. During the course of treatment, it was found that cisplatin is a highly toxic drug with severe nausea and vomiting, gastrointestinal toxicity, strong nephrotoxicity, bone marrow suppression, ototoxicity, peripheral neurotoxicity, etc. (Barabas K, Milner R, Lurie D , Adin C. Cisplatin: a review of toxicities and therapeutic applications. Vet Comp Oncol, 2008, 6:1-18). In order to overcome the shortcoming of high toxicity of cisplatin, the work of modifying the structure of cisplatin to discov...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00
CPCC07F15/0013
Inventor 应勇康宁丁炬平王年李光旭
Owner ZHUYUE TONGDA MEDICAL TECH DEV SUZHOU CO LTD
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