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Preparation method of high-purity and high-yield caspofungin impurity CO

A caspofungin, high-yield technology, applied in the chemical field, can solve the problem of how to obtain high-purity caspofungin impurities in large quantities, and achieve the effect of simple process

Active Publication Date: 2016-01-06
CHENGDU YATU BIOLOGICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The object of the invention is to provide a high-purity high-yield caspofungin impurity C 0 The preparation method solves the problem of how to obtain high-purity caspofungin impurity C in large quantities in the prior art 0 the problem of the method

Method used

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  • Preparation method of high-purity and high-yield caspofungin impurity CO
  • Preparation method of high-purity and high-yield caspofungin impurity CO
  • Preparation method of high-purity and high-yield caspofungin impurity CO

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Experimental program
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Effect test

Embodiment 1

[0022] Step 1: Add 100ml of acetonitrile into a 250ml three-necked bottle, and mix 10g of neomocontin B with stirring 0 and C 0 The solid (HPLC purity B 0 +C 0 96.1%, B 0 / C 0 =80 / 20), 2.3g of phenylboronic acid, 3.1g of thiophenol, placed in an external bath at -25 to -20°C, when the internal temperature dropped to -20°C, slowly add 4.3g of trifluoromethanesulfonic acid dropwise, and dropwise After completion, the reaction was continued for 3-4 hours, and the reaction was detected by TLC (EA / MeOH / 10% glacial acetic acid=82 / 8 / 8). After the basic reaction of the raw materials was complete, the reaction was stopped. Add sodium acetate aqueous solution (2.3g / 23ml) dropwise to the three-necked flask, and a large amount of white solids gradually precipitated. After the dropwise addition, stirred for 1 hour, filtered, and the solid was air-dried at 40°C to obtain 9.8g of intermediate I. HPLC Purity 91.6% (B 0 +C 0 91.6%, B 0 / C 0 =82 / 18), yield 90.2%.

[0023] Step 2: Add ...

Embodiment 2

[0026] Step 1: Add 100ml of acetonitrile into a 250ml three-necked bottle, and mix 10g of neomocontin B with stirring 0 and C 0 The solid (HPLC purity B 0 +C 0 95.1%, B 0 / C 0 =71 / 29), 2.3g of phenylboronic acid, 3.1g of thiophenol, placed in an external bath at -25 to -20°C, when the internal temperature dropped to -20°C, slowly add 4.3g of trifluoromethanesulfonic acid dropwise, and dropwise After completion, the reaction was continued for 3-4 hours, and the reaction was detected by TLC (EA / MeOH / 10% acetic acid=82 / 8 / 8). After the basic reaction of the raw materials was complete, the reaction was stopped. Add sodium acetate aqueous solution (2.3g / 23ml) dropwise to the three-necked bottle, and a large amount of white solids gradually precipitated. After the dropwise addition, stirred for 1 hour, filtered, and the solid was air-dried at 40°C to obtain 10.3g of intermediate Ⅰ, HPLC Purity 90.3% (B 0 +C 0 90.3%, B 0 / C 0 =72 / 28), yield 94.5%.

[0027] Step 2: Add 100ml ...

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Abstract

The invention discloses a preparation method of a high-purity and high-yield caspofungin impurity CO. The preparation method comprises step1, an intermediate I is prepared from solids containing pneumocandins BO and CO; step 2, a crude product of an intermediate II is prepared from the intermediate I, chromatography purification and separation are performed with a reversed-phase chromatography method and a normal-phase chromatography method, and the intermediate II is obtained; step3, a crude product of the caspofungin impurity CO is prepared from the intermediate II, chromatographic separation is performed with a reversed phase chromatography method, and the high-purity caspofungin impurity CO is obtained. By means of a specific combination and purification method of raw materials, the caspofungin impurity CO with HPLC (high performance liquid chromatography) purity higher than 97% can be obtained, and a way is provided for preparation of the caspofungin impurity CO. The purity of the product obtained with the method can completely meet the requirements, and a process is relatively simple.

Description

technical field [0001] The invention belongs to the field of chemistry, in particular to a high-purity and high-yield caspofungin impurity C 0 method of preparation. Background technique [0002] Caspofungin (caspofungin) is the first new echinocandin antifungal drug approved for marketing, which belongs to a semi-synthetic cyclic lipid compound and is a non-competitive β(1,3)-D-glucan Synthetic enzyme inhibitors. β(1,3)-D-glucan is an important component of the cell wall of various pathogenic fungi and Pneumocystis carinii, which does not exist in mammalian cells. Caspofungin acts by inhibiting its synthesis, destroying the integrity and osmotic balance of the fungal cell wall to achieve lysis. Its structure is as follows: [0003] [0004] Caspofungin Impurity C 0 It is an isomer of caspofungin, and its structure is as follows: [0005] [0006] In the field of drug testing, caspofungin impurity C is required 0 as a control. Caspofungin Impurity C 0 It is a ...

Claims

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Application Information

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IPC IPC(8): C07K7/56C07K1/20C07K1/16C07K1/02
Inventor 朱辉邓涛张翠英朱宇母荣光罗欢谢怀杰朱华勇庞雪
Owner CHENGDU YATU BIOLOGICAL TECH
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