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Vinyl sulfamido substituted pyrazolyl benzamide compound

A technology based on sulfonamide and benzamide, applied in the field of medicine

Active Publication Date: 2020-06-09
创沐医药科技(上海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Johnson & Johnson's FGFR inhibitor Erdafitinib, a reversible inhibitor, has been approved for urothelial carcinoma, but the resulting resistance problem remains to be resolved

Method used

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  • Vinyl sulfamido substituted pyrazolyl benzamide compound
  • Vinyl sulfamido substituted pyrazolyl benzamide compound
  • Vinyl sulfamido substituted pyrazolyl benzamide compound

Examples

Experimental program
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Effect test

Embodiment 1

[0104] Example 1: Synthesis of N-(5-(3,5-dimethoxyphenethyl)-1H-pyrazol-3-yl)-2-(vinylsulfonamido)benzamide

[0105]

[0106] Put 152mg (0.62mmol) intermediate A in the round bottom flask, N 2 Add 4ml of dry toluene under protection to dissolve, stir in ice bath for 10min, then add dropwise 0.58ml of trimethylaluminum solution (1.6M, 0.92mmol), react for 1h, add 235mg (0.92mmol) of intermediate B1, and stir for 20min Remove the ice bath, react at 65°C for 24h, cool down, add H 2 O quenched the reaction, extracted with ethyl acetate, and the resulting solution was washed with saturated NaCl solution, anhydrous NaCl 2 SO 4 dry. Separation and purification by silica gel column chromatography (gradient elution, dichloromethane: methanol = 250:1 to 100:1) to obtain light yellow powdery solid N-(5-(3,5-dimethoxyphenethyl)- 1H-pyrazol-3-yl)-2-(vinylsulfonamido)benzamide (compound 1, 116 mg, 41%). LCMS:m / z=457.2[M+H] + ; 1 HNMR(400MHz,DMSO-d6)δ11.35(br.s,2H),10.56(s,1H),7.36...

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Abstract

The invention provides a vinyl sulfamide substituted pyrazolyl benzamide compound. Specifically, the present invention provides a compound in formula I shown in the specification or a pharmaceuticallyacceptable salt thereof, and a preparation method and use thereof. The compound shown in the formula I has excellent FGFR inhibitory activity and can be used for preventing or treating diseases related to FGFR kinase activity or expression quantity, such as cancer.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular, relates to a new class of pyrazole compounds, a preparation method of such compounds, a pharmaceutical composition containing such compounds, and the use of such compounds as fibroblast growth factor receptor (FGFR) Use of the irreversible inhibitor in the prevention and treatment of diseases such as cancer. [0002] technical background [0003] Fibroblast growth factor (FGF) is a structurally related polypeptide consisting of 150-200 amino acids. There are about 20 members in this family, involved in developmental regulation, and expressed in various tissues. Fibroblast growth factor can stimulate cell proliferation, migration and differentiation, and plays an important role in bone and limb development, wound healing, tissue repair, hematopoiesis, angiogenesis and tumorigenesis. [0004] The biological effects of fibroblast growth factor are mediated through the fibroblast growth fac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/40A61K31/415A61P35/00A61P35/02
CPCC07D231/40A61P35/00A61P35/02
Inventor 李道飞于潇贺亚郝志明白崇荣
Owner 创沐医药科技(上海)有限公司