Purine compounds, composition and application

A technology of compounds and purines, applied in the field of medicine, can solve problems such as poor drug resistance and achieve 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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  • Purine compounds, composition and application
  • Purine compounds, composition and application
  • Purine compounds, composition and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] The synthetic method of such 2-phenylaminopurine compounds is illustrated by N-(9-(2-phenylamino)purine-2-(4-morpholinephenylamino))acrylamide.

[0065] The reaction path is as follows:

[0066]

[0067] Step A:

[0068] Take 1 (13.81g, 0.1mol) and sodium bicarbonate (12.6g, 0.15mol) in 30ml of acetonitrile, slowly add acryloyl chloride (9.5g, 0.105mol) dropwise under stirring, and react at room temperature for 5 minutes after the dropwise addition is completed. After the reaction was completed, 400ml of water was added, and a white solid was precipitated, which was suction filtered to obtain 18g of the product. (Yield: 93.8%)

[0069] Step B:

[0070] Take 3 (6g, 31.23mmol) and ammonium chloride (3.3g, 62.46mmol) in a reaction flask, add 20ml of MeOH and 20ml of water, add iron powder (7g, 125mmol) under stirring, raise the temperature to 60°C for 2 hours, and draw while hot Filter, wash the filter residue with ethyl acetate, extract the filtrate with ethyl acet...

Embodiment 2

[0086] The synthetic method of this kind of compound is illustrated with N-[9-(2-phenylamino)purine-2-[[4-(1-morpholine)propoxy]phenylamino]]acrylamide.

[0087] The reaction path is as follows:

[0088]

[0089] The title compound was prepared according to the schemes, procedures and intermediates described below.

[0090]

[0091] Steps A-D are the same as the intermediate preparation steps in the Example 1 scheme.

[0092] Step E:

[0093] Dissolve 8 (10g, 72mmol) in 30ml of acetonitrile, add potassium carbonate (14.9g, 108mmol) and potassium iodide (1.2g, 7.2mmol), slowly add 1-bromo-3-chloropropane (13.6g, 86mmol) dropwise, Raise the temperature to 70°C and react for 2 hours. After the reaction, the solvent was drained and 400ml of water was added to precipitate a yellow-white solid, which was filtered by suction to obtain 14g of solid. (yield: 90%)

[0094] Step F:

[0095] Dissolve 10 (4g, 18.56mmol) in 20ml of DMF, add potassium carbonate (3.8g, 27.84mmol) a...

Embodiment 3

[0098]The synthesis of this class is illustrated with N-[9-(2-phenylamino)purine-2-[[4-[(1-morpholine)acetyl]phenoxy]amino]]acrylamide.

[0099] The reaction path is as follows:

[0100]

[0101] The title compound was prepared according to the schemes, procedures and intermediates described below.

[0102]

[0103] Steps A-D are the same as the intermediate preparation steps in the Example 1 scheme.

[0104] Step E:

[0105] Dissolve 8 (20g, 143.88mmol) in 150ml of acetonitrile, add potassium carbonate (29g, 215.83mmol), potassium iodide (2.4g, 14.39mmol), slowly add ethyl bromoacetate (24g, 143.88mmol) dropwise, and heat up to 70°C The reaction was carried out for 2 hours. After the reaction was completed, the solvent was sucked dry, washed with water and filtered to obtain 27 g of a yellow-white solid. (yield: 85%)

[0106] Step F:

[0107] Take 10 (6g, 26.67mmol) in 50ml of water, slowly add potassium hydroxide (3g, 53.3mmol), heat up to 50°C for 1 hour, cool to...

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Abstract

The invention belongs to the technical field of medicine and relates to purine compounds, composition and an application of the composition. The compounds represented as a general formula (I) as well as all possible isomers, pharmaceutical salts or hydrates or the composition of the compounds are used for treating diseases caused by BTK (Bruton tyrosine kinase) and particularly used for treating diffuse large B cell lymphoma, follicular lymphoma or chronic lymphocytic leukemia.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to purine compounds represented by the general formula (I) and compositions thereof, wherein each substituent of the general formula (I) is as defined in the description. The present invention also relates to the use of the purine compound and composition in treating tumors by inhibiting protein 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. Receptor-type tyrosine kinas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/32A61K31/52A61K31/5377A61P35/00A61P35/02
CPCC07D473/32
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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