Amidine compound capable of preparing gefitinib and preparation method thereof

A technology of gefitinib and compounds, applied in the field of drug preparation

Inactive Publication Date: 2010-02-03
济南久创化学有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] Most of the existing raw materials for the preparation of gefitinib use 3-hydroxy-4-methoxybenzaldehyde, and no other

Method used

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  • Amidine compound capable of preparing gefitinib and preparation method thereof
  • Amidine compound capable of preparing gefitinib and preparation method thereof
  • Amidine compound capable of preparing gefitinib and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0037] Preparation of amidine compounds

[0038]

Embodiment 1

[0040] Transfer 0.5 moles (72.8 g) of 3-chloro-4-fluoroaniline and an equivalent molar amount of anthranilocyanide derivatives into a glass reaction vessel, mix well, protect under a nitrogen atmosphere, heat to 50 degrees to start melting, and heat to 80 ~ 100 degrees, the solid basically disappears completely, and a small amount of anhydrous AlCl is added several times under the condition of stirring 3 After the addition, the reaction mixture was heated to 180°C and kept for 30 minutes, then the heating was stopped, and the reactant was down to room temperature, and 200 ml of cold 10% hydrochloric acid solution was added dropwise under the condition of cooling in an ice-water bath, and the reactant was completely dissolved. Mole / liter concentration of sodium hydroxide solution adjust the solution to PH=6, extract 3 times with 100ml chloroform, separate the water phase, alkalinize with 2 moles / liter concentration of sodium hydroxide solution, a off-white solid precipitates, fi...

Embodiment 2

[0042] Transfer 0.5 moles (72.8 g) of 3-chloro-4-fluoroaniline and an equivalent molar amount of anthranilic cyanide derivatives into a glass reaction vessel, mix well, protect under a nitrogen atmosphere, heat until the solid disappears completely, and stir Add small amounts of anhydrous AlCl several times 3 , after the addition, the reaction mixture was heated to 150°C and kept for 50 minutes, then the heating was stopped, the reactant was down to room temperature, and 200ml of cold 10% hydrochloric acid solution was added dropwise under the condition of cooling in an ice-water bath, and the reactant was completely dissolved. Mole / liter concentration of sodium hydroxide solution adjust the solution to PH=6, extract 3 times with 100ml chloroform, separate the water phase, alkalinize with 2 moles / liter concentration of sodium hydroxide solution, a off-white solid precipitates, filter , and the solid recrystallized after drying. The yield is below 50%.

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Abstract

The invention belongs to the field of medicine preparation research and in particular relates to an amidine compound capable of preparing gefitinib. The invention relates to the amidine compound withthe structure as shown in formula (I) and a preparation method thereof. The quinazoline ring of the gefitinib prepared by the amidine compound has high yield which is generally over 80%, purificationis relatively simple and operability is strong.

Description

(1) Technical field [0001] The invention belongs to the field of medicine preparation research, in particular to a method for preparing 4-(3-chloro-4-fluorophenylamino)-7-methoxy-6-[3-(4-morpholinyl)propoxy Base] quinazoline (gefitinib, Gefitinib) amidine compound and preparation method thereof. (2) Background technology [0002] Gefitinib is a new type of anti-tumor drug developed by Astra Zeneca, and it is an orally available small molecule inhibitor of EGFR tyrosine kinase. The Iressa (ZD1839) molecule was discovered in 1994, and subsequent research found that the Iressa (ZD1839) molecule can inhibit the growth and survival of non-small cell lung cancer (NSCLC) and other tumors such as colorectal cancer, head and neck cancer, prostate cancer, and breast cancer cells , and its possible mechanisms include: (1) competing for the Mg-ATP binding site on the catalytic region of EGFR-TK, blocking its signal transmission; (2) inhibiting the activation of mitogen-activated protei...

Claims

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Application Information

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IPC IPC(8): C07D295/088C07C257/18B01J27/10
Inventor 冉东升张传伟
Owner 济南久创化学有限责任公司
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