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Heterocycle substituted pyrido-pyrrole kinase inhibitor

A technology of heterocyclic group and cycloalkyl group, which is applied in the direction of medical preparations containing active ingredients, urinary system diseases, organic active ingredients, etc., and can solve problems such as poor selectivity and insufficient activity

Inactive Publication Date: 2013-03-27
TONGHUA SIHUAN PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These compounds have problems such as poor selectivity or insufficient activity, so it is necessary to carry out corresponding research work to find small molecule inhibitors targeting b-RAF mutations and having good activity

Method used

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  • Heterocycle substituted pyrido-pyrrole kinase inhibitor
  • Heterocycle substituted pyrido-pyrrole kinase inhibitor
  • Heterocycle substituted pyrido-pyrrole kinase inhibitor

Examples

Experimental program
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Effect test

preparation example Construction

[0117] (2) Preparation of Intermediate TM 2

[0118] Dissolve the intermediate TM 1 (1 equivalent) in a mixed solution of an appropriate amount of methanol and water, add NaOH (3 equivalents), and react under the protection of nitrogen. After the reaction is completed for 6 hours, the reaction solution is spin-dried, and the pH is adjusted to 3 with dilute hydrochloric acid. . Dichloromethane was added to the mixture, extracted, separated, and the organic phase was anhydrous Na 2 SO 4 Dry and evaporate to dryness to obtain the intermediate TM 2.

[0119] (3) Preparation of Intermediate TM 3

[0120] The obtained intermediate TM 2 (1 equivalent) was dissolved in an appropriate amount of toluene, and then SOCl was added dropwise 2 (6 equivalents), reflux reaction at 100°C, after the reaction is complete, the reaction solution is spin-dried to obtain the crude product of intermediate TM 3, which is set aside.

[0121] (4) Preparation of Intermediate TM 4

[0122] The starti...

Embodiment 1

[0143] Example 1N-(5-(5-(4-chlorobenzene)-1H-pyrrole[2,3-b]pyridine-3-carbonyl)oxazol-2-yl)propane-1-sulfonamide (compound 1) Preparation

[0144]

[0145] (1) Preparation of intermediate TM 1-1

[0146] Under ice bath, the starting material SM 1 (2.34 g, 15.0 mmol) was dissolved in 50 ml CH 2 Cl 2 , and pyridine (3.8g, 50mmol) was added dropwise, and then 1-chloropropanesulfonyl chloride (2.8g, 15mmol) was added dropwise to the reaction solution. After the addition was complete, it was moved to room temperature and stirred overnight. After the reaction was completed, the reaction solution was spin-dried, washed with water and brine successively, and washed with anhydrous Na 2 SO 4 After drying, filtering, and column chromatography, intermediate TM 1-1 was obtained, 2.79 g, yield 71%.

[0147] (2) Preparation of Intermediate TM 1-2

[0148] The intermediate TM 1-1 (1.31g, 5.0mmol) was dissolved in a mixed solution of 40ml of methanol and water, NaOH (0.6g, 15.0mmol)...

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Abstract

The invention belongs to the medicine technical field, and concretely relates to a heterocycle substituted pyrido-pyrrole kinase inhibitor shown in a formula (I), its pharmaceutically acceptable salt or its solvate, wherein R1, R2, R3, L, M and Q are defined as an instruction. The invention also relates to a preparation method and an application of the compounds, the pharmaceutically acceptable salt or the solvate in preparation of medicines for treating / or preventing cancer-related or non cancer-related diseases.

Description

1. Technical field [0001] The present invention belongs to the technical field of medicine, and specifically relates to a heterocyclic substituted pyridopyrrole kinase inhibitor, a pharmaceutically acceptable salt or a solvate thereof, a preparation method of these compounds, and the compound, a pharmaceutically acceptable salt or a The application of its solvate in the preparation of medicines for treating and / or preventing cancer-related diseases. 2. Background technology [0002] Receptor tyrosine kinases (RTKs) are involved in cell growth, differentiation, development, proliferation, division, and adhesion, and are also related to cell transcription regulation, angiogenesis, and endothelial cell proliferation. has a wide range of effects. The regulation of these kinases can control cell proliferation and differentiation, regulate cell cycle, especially for some mutated tumor cells, by regulating the activity of overexpressed kinases, it can significantly inhibit the gro...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/437A61P35/00A61P17/00A61P13/08
Inventor 松山皓治
Owner TONGHUA SIHUAN PHARM
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