Quinolyl EGFR tyrosine kinase inhibitor containing zinc binding group

A technology of alkylamino and alkyl, which is applied in the field of medicine and can solve the problems of drug resistance of tumors

Inactive Publication Date: 2014-08-06
TONGHUA SIHUAN PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, their efficacy is limited to a small subset of specific patients due to the molecular heterogeneity of tumors
In addition, tumors rapidly become resistant to treatment with these tyrosine kinase inhibitors

Method used

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  • Quinolyl EGFR tyrosine kinase inhibitor containing zinc binding group
  • Quinolyl EGFR tyrosine kinase inhibitor containing zinc binding group
  • Quinolyl EGFR tyrosine kinase inhibitor containing zinc binding group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0130] Example 1 The preparation of 7-(4-(3-chloro-4-fluorophenylamino)-3-cyano-7-methoxyquinazolin-6-yloxy)-N-hydroxyheptanamide ( Compound 1)

[0131]

[0132] (1) Preparation of ethyl 2-cyano-3-ethoxyacrylate

[0133]

[0134] Dissolve triethoxymethane (16.65 mL, 0.1 mol) and ethyl dicyanoacetate (10.65 mL, 0.1 mol) in acetic anhydride (80 mL) solution, react at 150-160 °C for 5 hours, and cool to room temperature , concentrated under reduced pressure to remove the solvent to obtain the product (13.5 g, yield 80%).

[0135] (2) Preparation of ethyl 7-(4-amino-2-methoxyphenoxy)heptanoate

[0136]

[0137] 7-(2-Methoxy-4-nitrophenoxy)methyl heptanoate (17 g, 0.05 mol) was dissolved in THF / H 2 O (volume ratio 1:1, 200 mL) mixed solution was added palladium carbon (8 g), stirred under hydrogen atmosphere for 20 hours, filtered, and the filtrate was concentrated under reduced pressure to obtain the product (14 g, yield 94.8%).

[0138] (3) (Z)-Ethyl 7-(4-(2-cyano-3-et...

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Abstract

The invention belongs to the technical field of medicin and specifically relates to a quinolyl EGFR tyrosine kinase inhibitor containing a zinc binding group and a deuterated material, a pharmaceutically acceptable salt or stereoisomer thereof. The inhibitor is represented by a general formula (I) which is described in the specification; and in the general formula (I), R1, R2, R2', R3, R4, R5, R6, R7, W, X, L, T and n are as defined in the specification. The invention further relates to a preparation method for the inhibitor, a medicinal preparation containing the inhibitor and application of the inhibitor in preparation of drugs used for treating and/or preventing tumors.

Description

1. Technical field [0001] The invention belongs to the technical field of medicine, in particular to quinoline-based EGFR tyrosine kinase inhibitors containing zinc binding groups, deuterated products thereof, pharmaceutically acceptable salts thereof or stereoisomers thereof, the preparation methods of these compounds, comprising The pharmaceutical preparations of these compounds, and the application of these compounds in the preparation of medicines for treating and / or preventing tumors. 2. Background technology [0002] Epidermal growth factor receptor (EGFR) is a multifunctional glycoprotein widely distributed on the cell membrane of various human tissues, and it is an oncogene of avian erythroblasticleukemia virus (v-erb-b) Homologs. Human EGFR / HER1 / ErbB-1 and HER2 (human epidermal growth factor receptor-2) / ErbB-2 / Teu / p185, HER3 / ErbB-3, HER4 / ErbB-4, etc. are classified into the HER / ErbB family and belong to the same protein Tyrosine kinases (PTKs). Clinical studies h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/48C07D405/12C07D401/12A61K31/4709A61K31/4706A61K31/5377A61P35/00
CPCC07D215/54C07D401/12C07D405/12
Inventor 吴永谦
Owner TONGHUA SIHUAN PHARM
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