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Preparing method for gefitinib

A technology of gefitinib and methoxy, which is applied in the field of drug preparation, can solve problems such as unsatisfactory yield, many side reactions, and long reaction steps, and achieve improved total yield, improved overall yield, and short reaction steps Effect

Inactive Publication Date: 2008-03-26
SOUTHEAST UNIV
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Problems solved by technology

This route still has the disadvantage of long reaction steps, and there are many side reactions in the chlorination step, and the yield is not ideal

Method used

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  • Preparing method for gefitinib
  • Preparing method for gefitinib
  • Preparing method for gefitinib

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Embodiment Construction

[0032] The present invention prepares 4-(3-chloro-4-fluorophenylamino)-7-methoxy-6-[3-(4-morpholinyl) propoxy]quinazoline and adopts the following route:

[0033] 1.) Use methyl 3-hydroxy-4-methoxybenzoate as raw material, react with 4-(3-chloropropyl)morpholine, and introduce 3-morpholine on the 3-position oxygen atom in the first step reaction Phenylpropoxy, to give methyl 4-methoxy-3-[3-(4-morpholinyl)propoxy]benzoate,

[0034] 2.) Obtain 2-nitro-4-methoxy-5-[3-(4-morpholino) propoxy]methyl benzoate after nitration,

[0035] 3.) After reduction, 2-amino-4-methoxy-5-[3-(4-morpholinyl) propoxy]methyl benzoate was obtained,

[0036] 4.) Generate 7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazolin-4(3H)-one after ring closure,

[0037] 5.) After chlorination, 4-chloro-7-methoxyl-6-[3-(4-morpholinyl)propoxyl]quinazoline is obtained,

[0038] 6.) 4-chloro-7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline reacts with 3-chloro-4-fluoroaniline to obtain

[0039] 4-(3-Chloro-4-fluor...

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Abstract

The process of preparing gefitinib, 4-(3-chloro-4-fluorophenylamido)-7-methoxyl-6-[3-(4- morpholinyl) propoxy] quinazoline, includes following steps: 1. reaction of 3-hydroxy-4-methoxy methyl benzoate as material and 4-(3-chloropropyl) morpholine to obtain 4- methoxyl-3-[3-(4- morpholinyl) propoxy] methyl benzoate; 2. nitration to obtain 2-nitro-4- methoxyl-5-[3-(4- morpholinyl) propoxy] methyl benzoate; 3. reduction to obtain 2-amino-4- methoxyl-5-[3-(4- morpholinyl) propoxy] methyl benzoate; 4. closing cycle to create 7- methoxyl-6-[3-(4- morpholinyl) propoxy] quinazoline-4(3H)-one; 5. chlorinating to obtain 4-chloro-7- methoxyl -6-[3-(4-morpholinyl) propoxy] quinazoline; and 6. reaction to 3-chloro-4-fluoroaniline to obtain gefitinib.

Description

technical field [0001] The present invention relates to 4-(3-chloro-4-fluorophenylamino)-7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline (gefitinib, The preparation method of Gefitinib belongs to the technical field of medicine preparation. Background technique [0002] Gefitinib is an orally available small molecule inhibitor of EGFR tyrosine kinase developed by Astra Zeneca. In 2002, it was first marketed in Japan for the treatment of inoperable or recurrent non-small cell lung cancer. In May 2003, it was approved as a third-line monotherapy for advanced non-small cell lung cancer (NSCLC) in the United States and Australia. Target-specific small molecule tyrosine kinase inhibitors for tumor therapy. Approved by the State Food and Drug Administration (SFDA) on February 25, 2005, it was officially launched in China (trade name: Gefitinib) for the treatment of locally advanced or metastatic non-small cell lung cancer who have previously received chemotherapy. [0003] ...

Claims

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Application Information

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IPC IPC(8): C07D239/94
Inventor 吉民郑友广李铭东
Owner SOUTHEAST UNIV
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