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Heterocyclic amino and alkoxy-replaced quinazoline derivative and application thereof

A kind of heterocyclic aminoalkoxy, quinazoline technology, applied in the field of substituted quinazoline derivatives, can solve problems such as difficulty in drug selection

Active Publication Date: 2013-06-26
SHANGHAI FENGHUA PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Drug selection in clinical applications is difficult due to the variety of kinase variants

Method used

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  • Heterocyclic amino and alkoxy-replaced quinazoline derivative and application thereof
  • Heterocyclic amino and alkoxy-replaced quinazoline derivative and application thereof
  • Heterocyclic amino and alkoxy-replaced quinazoline derivative and application thereof

Examples

Experimental program
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preparation example Construction

[0252] The preparation method provided in the present invention should be understood as an example for the sake of full disclosure, rather than limiting the scope of protection required by the present invention. Those skilled in the art can prepare various compounds provided by the present invention according to the guidance of textbooks, experimental manuals or the examples listed in the present invention. The preparation of these compounds also belongs to the general skills that a person of ordinary skill in the art should have, and can also be completed under the guidance of the prior art. Specifically, the preparation method of some compounds provided by the invention is as follows:

[0253] Synthetic method one:

[0254]

[0255] Synthetic method two:

[0256]

Embodiment 1

[0265] Example 1 Synthesis of 4-(3'-chloro-4'-fluoroanilino)-6-[3-(2-oxa-6-azaspiro[3.3]heptane-6-yl) according to synthetic method one -propoxy]-7-methoxyquinazoline (3-C-B)

[0266]

[0267] 1 H NMR (CDCl 3 )8.67(s,1H), 8.03(s,2H), 7.68(br,1H), 7.46(s,1H), 7.25(s,1H), 7.18(m,1H), 4.79(s,4H), 4.25(m,2H), 4.01(s,3H), 3.66(s,4H), 2.80(m,2H), 2.03(m,2H). ES-MS(m / z):459.1(MH + ).

Embodiment 2

[0268] Example 2 Synthesis of 4-(3'-chloro-4'-fluoroanilino)-6-[3-(2-oxa-6-azaspiro[3.4]octane-6-yl according to synthetic method one )-propoxy]-7-methoxyquinazoline (3-C-C)

[0269]

[0270] 1 H NMR (CDCl 3 )8.67(s,1H), 8.20(s,1H), 8.07(q,J=2.4Hz,1H), 7.70(m,1H), 7.57(s,1H), 7.25(s,1H), 7.17( t,J=8.8Hz,1H), 4.69(q,J=6.4Hz,4H), 4.30(t,J=6.8Hz,2H), 4.01(s,3H), 3.18(s,2H), 2.90( t,J=6.4Hz,4H), 2.33(t,J=7.2Hz,2H), 2.22(m,2H). ES-MS(m / z):473.0(MH + ).

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Abstract

The invention discloses a heterocyclic amino and alkoxy-replaced quinazoline derivative and a pharmaceutically acceptable salt. The derivative inhibits the activity of a receptor tyrosine kinase epidermal growth factor receptor (EGFR) and can be used for treating cancers related to the receptor tyrosine kinase expression of an ErbB family.

Description

technical field [0001] The invention relates to a substituted quinazoline derivative, in particular to a heterocyclic aminoalkoxy substituted quinazoline derivative and a pharmaceutically acceptable salt thereof. The derivative is used as an active ingredient to inhibit the activity of the receptor tyrosine kinase EGFR, so as to reduce the phosphorylation of the tyrosine residue contained in the substrate by the kinase, so that various diseases caused by it (such as: tumors) have been effectively improved and treated. Background technique [0002] Traditional chemotherapy drugs achieve cancer treatment by inhibiting the DNA synthesis process or inhibiting the cell division process. Practice has shown that these compounds are usually also somewhat toxic to normal cells. Molecular targeted therapies (MTTs) developed in the past one or two decades can greatly reduce the toxicity of drugs to normal tissue cells. Imatinib for the treatment of Chronic Myeloid Leukemia (CML) has...

Claims

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Application Information

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IPC IPC(8): C07D491/107C07D498/08C07D487/10C07D491/048C07D471/10C07D498/10C07D495/10C07D487/04C07D471/04A61K31/517A61K31/5386A61K31/55A61P35/00A61P35/02
CPCA61P35/00A61P35/02C07D239/94C07D401/12C07D403/14C07D471/04C07D471/10C07D487/04C07D487/10C07D491/06C07D491/107C07D495/10C07D498/08
Inventor 钱卫
Owner SHANGHAI FENGHUA PHARMA CO LTD