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A class of aromatic heterocyclic compounds with kinase inhibition activity

A compound and aryl technology, applied in the field of small molecule drugs, can solve problems such as adverse reactions and serious infections

Inactive Publication Date: 2020-03-31
SHANGHAI ENNOVABIO PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, patients who take these drugs experience some adverse effects, such as anemia, possible serious infection and risk of heart failure

Method used

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  • A class of aromatic heterocyclic compounds with kinase inhibition activity
  • A class of aromatic heterocyclic compounds with kinase inhibition activity
  • A class of aromatic heterocyclic compounds with kinase inhibition activity

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0072] The preparation of formula I compound

[0073] Compounds of formula I of the present invention can be prepared by the following methods:

[0074]

[0075] Pharmaceutical compositions and methods of administration

[0076] Since the compound of the present invention has excellent JAK kinase inhibitory activity, the compound of the present invention and its various crystal forms, pharmaceutically acceptable inorganic or organic salts, hydrates or solvates, and compounds containing the compound of the present invention as the main active ingredient The pharmaceutical composition of can be used to prevent and / or treat diseases related to JAK kinase activity or expression level (for example, cancer).

[0077] The pharmaceutical composition of the present invention comprises the compound of the present invention and pharmaceutically acceptable excipients or carriers in a safe and effective amount range. Wherein, "safe and effective dose" refers to: the amount of the comp...

Embodiment 1

[0090] Example 1: N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)-3-(2-((3-methoxy-1-methyl-1H-pyridine Azol-4-yl)amino)-5-methylpyrimidin-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-amine

[0091]

Embodiment 1-2

[0092] Example 1-2: 7-chloro-1-toluenesulfonyl-1H-pyrrolo[2,3-c]pyridine

[0093]

[0094] Under ice-water bath conditions, sodium hydrogen (375 mg, 9.37 mmol) was added in portions to a solution of compound 1-1 (950 mg, 6.25 mmol) in DMF (15 mL), and stirred for 20 minutes. Then p-toluenesulfonyl chloride (1.42 g, 9.37 mmol) was added to the solution in portions, and stirred at room temperature for 4 hours. The reaction was monitored by TLC and LCMS. After 1-1 disappeared, the reaction was quenched with 100 ml of water, extracted three times with ethyl acetate (50 mL*3), the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to give the product (1.45 g, yield 76%). MS(ESI):m / z=307[M+H] + .

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Abstract

The invention provides a kinase inhibitor, a preparation method and applications thereof, specifically a compound represented by a formula I, wherein each group is defined in the specification. According to the invention, the compound has excellent JAK inhibitory activity, so that the compound can be used for preparing pharmaceutical compositions for treating cancers and other JAK activity relateddiseases.

Description

technical field [0001] The invention relates to the field of small molecule drugs, in particular, the invention relates to a kinase inhibitor and its preparation and use. Background technique [0002] Janus kinases (JAKs) are cytoplasmic tyrosine protein kinases responsible for transducing many inflammation-related cytokine signals from cytokine membrane receptors to STAT transcription factors. It is generally believed that it mainly includes four family members: JAK1, JAK2, JAK3 and TYK2. When a specific cytokine binds to its receptor, the JAK family members coupled to the receptor undergo autophosphorylation and / or transphosphorylation of each other, and then phosphorylate the substrate protein STATs, and the phosphorylated STATs migrate to the nucleus to regulate Transcription, which transmits extracellular signals into the cell. The JAK-STAT intracellular signal transduction pathway is the core signal transduction pathway related to immune and inflammatory responses in...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D487/04A61P35/00A61P9/00A61P29/00A61P37/02A61P31/12A61P3/00A61P37/06A61P35/02A61P19/02A61P19/08A61P11/00A61P11/02A61P19/06A61K31/506A61K31/519
CPCA61P3/00A61P9/00A61P11/00A61P11/02A61P19/02A61P19/06A61P19/08A61P29/00A61P31/12A61P35/00A61P35/02A61P37/02A61P37/06C07D471/04C07D487/04
Inventor 江磊冯志勇毛旭东尚珂寿建勇吴淡宜徐圆张建华郑明伟
Owner SHANGHAI ENNOVABIO PHARM CO LTD
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