Aminopyrimidopyrazole/pyrrole derivatives and preparation method and use thereof

An alkyl and aryl technology, applied in the direction of drug combination, pharmaceutical formula, medical preparations containing active ingredients, etc., to achieve the effect of inhibiting the growth of tumors

Active Publication Date: 2022-07-01
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, elevated levels of FGF-2 were detected in IPF patients with idiopathic pulmonary fibrosis, FGFR-1 expression was increased in epithelial cells, endothelial cells and smooth muscle cells / fibroblast-like cells, and FGFR-2 in mesenchymal cells Increased expression, and studies have shown that FGF-2 is significantly overexpressed in diabetic nephropathy and stimulates the proliferation of glomerular mesangial cells; promotes the regeneration of renal tubular cells and leads to cell fibrosis

Method used

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  • Aminopyrimidopyrazole/pyrrole derivatives and preparation method and use thereof
  • Aminopyrimidopyrazole/pyrrole derivatives and preparation method and use thereof
  • Aminopyrimidopyrazole/pyrrole derivatives and preparation method and use thereof

Examples

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Embodiment 1

[0120] Example 1 Preparation of the compound of the present invention

[0121]

[0122] Raw material 1 (1.08 g, 8 mmol) was dissolved in DMF (20 mL), N-iodosuccinimide (4.5 g, 20 mmol) was added, and the reaction was performed at 80° C. for 5 h and monitored by TLC. After the reaction was completed, the reaction was quenched with a saturated aqueous solution of hydrosulfite, the reaction solution was poured into water, a yellow solid was precipitated, the solid was filtered and dried to obtain Intermediate 2 (white solid, 98%), MS m / z (ESI) : 261.9[M+H] + .

[0123]

[0124] Intermediate 2 (2.09 g, 8 mmol) was dissolved in 150 mL of tetrahydrofuran, compound 3 (1.8 g, 9.6 mmol), triphenylphosphine (4.2 g, 16 mmol) were added, N 2 protection, stirred at 0 °C, and then added dropwise diisopropyl azodicarboxylate (3.1 mL, 16 mmol), the dropwise addition was completed, and after half an hour, the reaction was transferred to room temperature for 3 h and monitored by TLC. A...

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Abstract

The invention relates to aminopyrimidopyrazole / pyrrole derivatives, a preparation method and application thereof, and belongs to the field of medicine. The present invention provides the compound represented by formula I, its optical isomer, and the pharmaceutically acceptable salt of the compound or its optical isomer. Biological experiments have proved that the compound of the present invention can not only significantly inhibit the proliferation of breast cancer, lung cancer, colorectal cancer, gastric cancer, bile duct cancer, urothelial cancer and other cancer cells, but also has a broad-spectrum anti-cancer effect, and has a broad-spectrum anti-cancer effect. The proliferation of cells and hepatic stellate cells also showed inhibitory effect, and could inhibit tumor growth in vivo, providing a new option for the development of anti-tumor and anti-fibrotic drugs.

Description

technical field [0001] The invention relates to aminopyrimidopyrazole / pyrrole derivatives, a preparation method and application thereof, and belongs to the field of medicine. Background technique [0002] Receptor tyrosine kinase RTKs are a class of cell surface transmembrane protein receptors with endogenous protein tyrosine kinase activity, usually composed of an extracellular domain that can bind to specific ligands, a transmembrane domain and a transmembrane domain. Consists of an intracellular kinase domain that selectively binds to and phosphorylates substrates. Binding ligands to the extracellular structural regions of RTKs causes structural changes to produce enzymatic activity. It plays an important regulatory role in tumor angiogenesis, tumor cell survival, proliferation, differentiation and migration. More than 50 different RTKs family members have been found, mainly including fibroblast growth factor receptors (FGFRs), epidermal growth factor receptors (EGFRs),...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/519A61P1/16A61P11/00A61P35/00
CPCC07D487/04A61P1/16A61P11/00A61P35/00
Inventor 叶庭洪魏于全曹丹武秀丽刘红垚于艳姚于勤
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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