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Adamantyl quinazoline compound, composition and application of adamantyl quinazoline compound and composition

An adamantyl quinazoline and adamantyl technology, applied in the field of medicine, can solve the problems of poor drug resistance and the like, and achieve the effect of good curative effect

Inactive Publication Date: 2017-02-22
DALIAN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs inevitably have the problem of poor drug resistance

Method used

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  • Adamantyl quinazoline compound, composition and application of adamantyl quinazoline compound and composition
  • Adamantyl quinazoline compound, composition and application of adamantyl quinazoline compound and composition
  • Adamantyl quinazoline compound, composition and application of adamantyl quinazoline compound and composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] The reaction path is as follows:

[0062]

[0063] Compound (II):

[0064]

[0065] As above reaction equation, compound A1-6 synthesis method is as follows:

[0066] Step 1 Synthesis of intermediates 2a-e, the reaction conditions are as follows: (a) using raw materials compound 1a-e and thionyl chloride as raw materials, at a constant temperature of 80°C, and reacting for 2 hours;

[0067] Step 2 Synthesis of intermediates 3a-e, the reaction conditions are: (b) use intermediates 2a-e and 1-aminoadamantane as raw materials, and reflux in acetone solution of sodium bicarbonate for 2 hours;

[0068] Step 3 Synthesis of intermediates 4a-e, the reaction conditions are: (c) use intermediates 3a-e and ammonium chloride as raw materials, iron powder as a catalyst, and react in methanol aqueous solution at a constant temperature of 80°C for 6 hours;

[0069] Step 3 Synthesis of compound A1-6, the reaction conditions are: (d) Using intermediate 4a-e and raw material comp...

Embodiment 2

[0086] The reaction path is as follows:

[0087]

[0088] Compound (II):

[0089]

[0090] As above reaction equation, compound B1-6 synthesis method is as follows:

[0091] Step 1 Synthesis of intermediates 6a-e, the reaction conditions are: (a) using raw material compounds 5a-e and 1-adamantanyl chloride as raw materials, refluxing in acetone solution of sodium bicarbonate for 2 hours;

[0092] Step 2 Synthesis of intermediates 7a-e, the reaction conditions are: (b) use intermediates 6a-e and ammonium chloride as raw materials, iron powder as a catalyst, and react in methanol aqueous solution at a constant temperature of 80°C for 6 hours;

[0093] The reaction conditions for the synthesis of the product B1-6 in Step 3 are as follows: (c) Use the intermediate 7a-e and the raw material compound (II) as raw materials, and reflux in a methanol solvent for 2 hours.

[0094] The selection of the compound B1-6 substituent is as follows:

[0095]

[0096]

[0097] The...

Embodiment 3

[0111] The reaction path is as follows:

[0112]

[0113] Compound (II):

[0114]

[0115] As above reaction equation, compound C1-12 synthesis method is as follows:

[0116] Step 1 Synthesis of intermediate 9a-e, the reaction conditions are: (a) use raw material compound 8a-e, ethyl bromoacetate, and potassium carbonate as raw materials, reflux in acetone solvent for 2h; and then (b) add 1mol / L hydrogen Sodium oxide solution, stirred at room temperature for 2 hours;

[0117] Step 2 Synthesis of intermediates 10a-e, the reaction conditions are: (c) use intermediates 9a-e and oxalyl chloride as raw materials, and reflux for 2 hours; then (d) add 1-adamantanamine and sodium carbonate, and reflux in acetone 2h;

[0118] Step 3 Synthesis of intermediates 11a-e, the reaction conditions are: (e) Use intermediates 10a-e and ammonium chloride as raw materials, iron powder as a catalyst, and react in methanol aqueous solution at a constant temperature of 80°C for 6 hours;

[...

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Abstract

The invention discloses an adamantyl quinazoline compound, a composition and application of the adamantyl quinazoline compound and the composition. The compound shown in a formula (I) and all possible isomers or pharmaceutically acceptable salts or hydrates or compositions are used to treat diseases caused by EGFR (Epidermal Growth Factor Receptor) tyrosine kinase, and are particularly used to treat non-small cell lung cancer, small cell lung cancer, squamous-cell carcinoma, breast cancer and gastric carcinoma.

Description

technical field [0001] The present invention belongs to the technical field of medicine, and relates to adamantyl quinazoline compounds represented by general formula (I) and compositions thereof, wherein each substituent of general formula (I) is as defined in the description. The present invention also relates to the use of the adamantyl quinazoline compound and composition for treating tumors by inhibiting tyrosine kinase. Background technique [0002] Protein tyrosine kinases (PTKs) regulate a series of physiological and biochemical processes such as cell growth, differentiation, and apoptosis by controlling cell signal transduction pathways. The disorder of protein tyrosine kinase function, especially their abnormal expression not only leads to the disorder of cell proliferation regulation, but also leads to tumorigenesis, and is closely related to tumor invasion and metastasis, tumor angiogenesis, and tumor resistance to radiotherapy and chemotherapy. relevant. Recep...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/94A61K31/517A61K31/5377A61P35/00
CPCC07D239/94
Inventor 马晓东于海晴宋安然葛阳宋振东黄姗姗王长远刘克辛
Owner DALIAN MEDICAL UNIVERSITY
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