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Method for synthesizing nitrosoureas antineoplastic drugs through stannic chloride-sodium nitrite system

An anti-tumor drug and sodium nitrite technology, which is applied in the field of synthesizing nitrosourea anti-tumor drugs with the tin tetrachloride-sodium nitrite system, can solve the problems of low yield and cumbersome post-processing, and achieve cost reduction and responsiveness. The effect of fast speed and mild reaction conditions

Inactive Publication Date: 2013-03-13
ASTATECH CHENGDU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] The technical problem to be solved by the present invention is that the yield of the traditional synthesis method is low, and the aftertreatment is loaded down with trivial details

Method used

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  • Method for synthesizing nitrosoureas antineoplastic drugs through stannic chloride-sodium nitrite system
  • Method for synthesizing nitrosoureas antineoplastic drugs through stannic chloride-sodium nitrite system
  • Method for synthesizing nitrosoureas antineoplastic drugs through stannic chloride-sodium nitrite system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] a. SnCl at room temperature 4 ·5H 2 O (3.5g, 10mmol) solid, 1,3-bis(2-chloroethyl)urea (1.9g, 10mmol) and sodium nitrite (0.7g, 10mmol) were added to 30ml of dichloromethane, stirred for 2 hours .

[0048] b, filter to remove the insoluble matter, and the filtrate is washed with saturated NaHCO 3 Solution washing, anhydrous Na 2 SO 4dry.

[0049] c. The filtrate was filtered to remove the desiccant, dichloromethane was evaporated with a rotary evaporator, and the obtained solid was recrystallized with isopropanol. Carmustine (1.9 g, 9.1 mmol) was obtained with a yield of 91%.

Embodiment 2

[0051] a. SnCl at room temperature 4 ·5H 2 O (15.8g, 45mmol) solid, 1,3-bis(2-chloroethyl) urea (5.6g, 30mmol) and sodium nitrite (3.1g, 45mmol) were added to 80ml of carbon tetrachloride, stirred for 3.5 Hour.

[0052] b, filter to remove the insoluble matter, and the filtrate is washed with saturated KHCO 3 Solution washing, anhydrous Na 2 SO 4 dry.

[0053] c. The filtrate was filtered to remove the desiccant, and the carbon tetrachloride was evaporated with a rotary evaporator, and the obtained solid was recrystallized with a mixed solvent of water-acetone (10ml: 40ml). Carmustine (5.8 g, 27.3 mmol) was obtained with a yield of 91%.

Embodiment 3

[0055] a. SnCl at room temperature 4 ·5H 2 O (35g, 100mmol) solid, 1,3-bis(2-chloroethyl)urea (9.3g, 50mmol) and sodium nitrite (7g, 100mmol) were added to 150ml 1,2-dichloroethane, stirred React for 5 hours.

[0056] b. Filter to remove the insoluble matter, and the filtrate is washed with saturated KH 2 PO 4 Solution washing, anhydrous Na 2 SO 4 dry.

[0057] c. Remove the desiccant from the filtrate, evaporate 1,2-dichloroethane with a rotary evaporator, and recrystallize the obtained solid with a mixed solvent of water-ethanol (5ml︰45ml). Carmustine (9.7 g, 45.5 mmol) was obtained with a yield of 91%.

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Abstract

The invention belongs to the field of chemistry, and particularly relates to a method for synthesizing nitrosoureas antineoplastic drugs through a stannic chloride-sodium nitrite system, and the method is used for solving the technical problems of low yield and complicated after-treatment of a conventional synthetic method. The technical scheme adopted by the invention is as follows: the method for synthesizing the nitrosoureas antineoplastic drugs through the stannic chloride-sodium nitrite system comprises the following steps: a, adding stannic chloride, precursors of nitrosoureas antineoplastic drugs and nitrous acid to chloralkane, and stirring; b, filtering to remove insoluble substances, and washing the filtrate by using a saturated weak alkaline solution, and then drying; and c, removing chloralkane from the dried filtrate, and recrystallizing the obtained solid, so as to obtain the nitrosoureas antineoplastic drugs. The invention provides a novel high-yield method for synthesizing nitrosoureas antineoplastic drugs.

Description

technical field [0001] The present invention belongs to the field of chemistry. Specifically, it relates to a method for synthesizing nitrosourea antitumor drugs through a tin tetrachloride-sodium nitrite system. Background technique [0002] The structural formula of the current nitrosourea antineoplastic drugs is The structural formula of the nitrosourea antitumor drug precursor is Wherein the substituents R are respectively: [0003] [0004] The corresponding nitrosourea antineoplastic drugs are: A is carmustine, B is lomustine, C is semustine, D is nimustine, E is formustine, F is Ramustine. [0005] Nitrosation is one of the key steps in the synthesis of nitrosourea antineoplastic drugs, because it often occurs in the last step, and its yield plays a decisive role in the cost of synthesizing nitrosourea antineoplastic drugs. Most of the traditional methods use anhydrous formic acid / sodium nitrite system or 15% hydrochloric acid / sodium nitrite system; when usi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/02C07C273/18C07C275/66C07D239/42C07F9/40C07H1/00C07H15/04
Inventor 黄永学何晓
Owner ASTATECH CHENGDU PHARMA
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