Pyridine chemical, its preparation method, and pharmaceutical composition containing the chemical and application thereof

A kind of compound and pyridine technology, applied in the field of pyridine compound, its preparation, pharmaceutical composition containing the compound and its use, can solve problems such as limited structure

Active Publication Date: 2013-01-02
CHIA TAI TIANQING PHARMA GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many inhibitors developed for this signaling pathway, the structure is still very limited.

Method used

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  • Pyridine chemical, its preparation method, and pharmaceutical composition containing the chemical and application thereof
  • Pyridine chemical, its preparation method, and pharmaceutical composition containing the chemical and application thereof
  • Pyridine chemical, its preparation method, and pharmaceutical composition containing the chemical and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0051] Preparation of Example 1 Compound IA-1

[0052]

[0053] Compound 1 (109.8mg, 0.2mmol), 1-(4-bromophenyl)-4-methylpiperazine (50.8mg, 0.2mmol), palladium acetate (0.015mmol), bis(diphenylphosphino) Ferrocene (0.032 mmol), cesium carbonate (106 mg, 0.28 mmol) were added to a dry round bottom flask. Evacuate and replace with nitrogen three times. 1,4-Dioxane was added under nitrogen protection. Heat to reflux and stir overnight. After filtration, the filtrate was concentrated, mixed with silica gel, and subjected to direct column chromatography (chloroform:methanol=10:1) to obtain compound IA-1 (110 mg). 1 H NMR (300MHz, CDCl 3 )δ7.88(s, 1H), 7.56(m, 3H), 7.49(s, 1H), 7.30(m, 3H), 7.10(s, 1H), 7.05(t, J=7.5Hz, 1H), 7.03(s, 1H), 6.93(s, 2H), 6.14(q, J=6.6Hz, 1H), 4.23(m, 3H), 3.17(s, 4H), 2.90(m, 2H), 2.60(m , 4H), 2.38(s, 3H), 2.16(m, 2H), 1.94(m, 2H), 1.89(d, J=6.6Hz, 3H), 1.48(s, 9H).

preparation Embodiment 2

[0054] Preparation of Example 2 Compound IA-2

[0055]

[0056] Trifluoroacetic acid (0.1 mL) was added dropwise to a dichloromethane solution (5 mL) of compound IA-1 (100 mg), stirred at room temperature overnight, and concentrated. Add ammonia in methanol (10% X 20mL) solution to the concentrated solution, and concentrate. The sample was mixed with silica gel and subjected to direct column chromatography (chloroform:methanol=10:1) to obtain compound IA-2 (75 mg). 1 H-NMR (300MHz, CDCl 3 ):δ 1 H NMR (300MHz, CDCl 3 )δ7.67(s, 1H), 7.44(m, 2H), 7.34(m, 2H), 7.20(m, 1H), 6.94(m, 3H), 6.14(q, J=6.6Hz, 1H), 4.23(m, 3H), 3.17(s, 4H), 2.90(m, 2H), 2.60(m, 4H), 2.38(s, 3H), 2.16(m, 2H), 1.94(m, 2H), 1.89 (d, J=6.6Hz, 3H).

preparation Embodiment 3

[0057] Preparation of Example 3 Compound IA-3

[0058]

[0059] Compound IA-3 was synthesized in the same manner as compound IA-1 of Preparation Example 1, except that bromobenzene was used instead of 1-(4-bromophenyl)-4-methylpiperazine. 1 H NMR (300MHz, CDCl 3 )δ7.92(s, 1H), 7.70(m, 2H), 7.61(s, 1H), 7.51(s, 1H), 7.31(m, 3H), 7.05(t, J=8.1Hz, 1H), 6.98(m, 2H), 6.16(q, J=6.6Hz, 1H), 4.25(m, 3H), 2.90(m, 2H), 2.14(m, 2H), 1.92(m, 5H), 1.48(s , 9H).

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PUM

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Abstract

The invention relates to a pyridine chemical shown as the following general formula and having c-Met and/or ALK inhibitory activity and its pharmaceutically-acceptable salt or pharmaceutically-acceptable solvate, a preparation method thereof, a pharmaceutical composition containing the chemicals, and applications of the chemicals in preparation of medicines for preventing and treating abnormal proliferation and morphological change of cells and related diseases, such as hyperkiesis, related to hepatocyte growth factor receptor (HGFR) and/or anaplastic lymphoma kinase (ALK) in organism and diseases related to vascularization or cancerometastasis, especially application in preparation of medicines for treating and preventing growth and metastasis of tumor.

Description

technical field [0001] The present invention relates to a class of pyridine compounds with c-Met and / or ALK inhibitory activity and pharmaceutically acceptable salts or pharmaceutically acceptable solvates thereof, a preparation method thereof, a pharmaceutical composition containing the compound, and These compounds are prepared for the prevention or treatment of diseases related to abnormal cell proliferation, morphological changes and motor hyperfunction related to hepatocyte growth factor receptor (HGFR) and / or anaplastic lymphoma kinase (ALK) in vivo, As well as the use of drugs for diseases related to angiogenesis or cancer metastasis, especially drugs for treating or preventing tumor growth and metastasis. Background technique [0002] Hepatocyte growth factor (hepatocyte growth factor, HGF), also known as scatter factor (SF), is the endogenous ligand of c-Met, a family of tyrosine kinase receptors. Proto-oncogene Met and HGF / SF are co-expressed in breast cancer, col...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D487/04A61K31/5377A61K31/496A61K31/4545A61P35/00A61P35/04
Inventor 张翱耿美玉王元相艾菁彭霞
Owner CHIA TAI TIANQING PHARMA GRP CO LTD
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