Glucose phosphonic amide crystals and preparation process and use thereof

A glufosfamide and crystallization technology, applied in the preparation field of the crystallization, can solve problems such as unfavorable physical properties and product stability, and achieve the effects of easy production and good stability

Active Publication Date: 2008-01-02
QILU PHARMA HAINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] German patent DE 3835772 and US 5,622,936, etc. disclose the preparation method of glufosfamide, all of which are in an amorphous form, and its physical properties are not conducive to the stability of the product, large-scale preparation and subsequent application

Method used

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  • Glucose phosphonic amide crystals and preparation process and use thereof
  • Glucose phosphonic amide crystals and preparation process and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Put 10g of crude glufosfamide into a 500ml three-necked bottle, add 50ml of acetone to dissolve at 20-50°C, place it at -20°C-50°C for crystallization, after 24 hours, filter it with suction, and dry it under vacuum at 20-50°C to obtain Glufosfamide Phosphonamide white crystals.

[0042] The glufosfamide crystals have a molecular weight of 383.17 and a crystal density of 1.537g / cm 3 , in the form of colorless transparent flakes, the crystal size used in the diffraction test is 0.02×0.40×0.50mm, it belongs to the triclinic system, the space group is P1, the unit cell parameters a=5.841(1), b=7.813(1), c= 18.271(2) Ȧ, α=95.795(1), β=93.442(1), γ=89.925(1)°. Unit cell volume V=828.0(2) Ȧ 3 , the number of molecules in the unit cell z=1.

[0043] Table 1 Atomic coordinate parameters and equivalent temperature factors of glufosfamide crystallization

[0044] X

Y

Z

Biso

CL1

.2847

.5422

.2359

9.6(4)

CL2

1.4076(8) ...

Embodiment 2

[0051] Put 10g of crude glufosfamide into a 500ml three-necked bottle, add 50ml of ethanol to dissolve at 20-50°C, place it at -20°C-50°C to crystallize, after 2-48 hours, suction filter, and vacuum dry at 20-50°C, that is Glufosfamide was obtained as white crystals.

Embodiment 3

[0053] Put 10g of the crude product of glufosfamide into a 500ml three-neck bottle, add 50ml of butanone to dissolve at 20-50°C, add 500ml of n-hexane and place it to crystallize at -20°C-50°C, filter it with suction, and dry it in vacuum at 20-50°C to obtain Glufosfamide is a white crystal.

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Abstract

The invention relates to a N,N'-di-(2-chloroethyl)phosphoryl diamino acid-beta-D- glucopyranosyl ester(glufosfamide) crystal, of which its space group is P1, cell parameter of a is equal to 5.841(1), b is equal to 7.813(1), c is equal to 18.271(2), alpha is equal to 95.795(1), beta is equal to 93.442(1), gamma compound is equal to 89.925(1), cell volume V is equal to 828.0(2) 3, and number of molecules Z in the crystal cell is equal to 1. The invention also relates to a method for preparation of N,N'-di-(2-chloroethyl)phosphoryl diamino acid-beta-D-pyranglucosester crystal adopting one or multisolvents. The glufosfamide crystal of this invention is of easy preparation and good stability, and is suitable for industrial production and preservation. The invention also relates to the application of this said crystal in the field of antineoplastic.

Description

technical field [0001] The invention relates to a crystal of glufosfamide, and also relates to a preparation method and application of the crystal. Background technique [0002] Glufosfamide (Glufosfamide), chemical name N, N'-bis(2-chloroethyl)phosphorodiamidate-β-D-glucopyranose ester (N,N'-bis(2-chloroethyl)phosphorodiamidate acid β-D-Glucopyranosyl ester), a new type of alkylating agent, belongs to the derivative of phosphoramide nitrogen mustard, which is obtained by linking the active part of the alkylating compound with a glucose molecule. Its mechanism of action is in line with the characteristics of alkylating agents. It induces irreversible inter-strand cross-linking of DNA, resulting in DNA double-strand breaks, which in turn induces apoptosis and inhibits the growth of tumor cells. [0003] In vivo experiments showed that the inhibitory activity of glufosfamide on mouse L-1210, human KB tumor cells, and childhood leukemia was equivalent to that of ifosfamide nit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H11/04C07H13/00C07H15/00C07F9/24A61K31/70A61P35/00
Inventor 王晶翼胡晓燕初乐玲张明会朱屹东范传文冷传新孙金凤
Owner QILU PHARMA HAINAN
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