Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Phenyl-1h-pyrazole derivatives and their application in antitumor drugs

A technology of pyrazoles and derivatives, which is applied in the field of new phenyl-1H-pyrazole derivatives, can solve the problems of small molecule drugs on the market, and achieve the effect of novel skeleton, good activity and great research value

Active Publication Date: 2021-03-05
GUANGZHOU HANDY BIOTECH CO LTD
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no small-molecule drug targeting this target on the market in China

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Phenyl-1h-pyrazole derivatives and their application in antitumor drugs
  • Phenyl-1h-pyrazole derivatives and their application in antitumor drugs
  • Phenyl-1h-pyrazole derivatives and their application in antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] (1) Synthesis of ethyl 5-methyl-1-phenyl-1H-pyrazole-3-carboxylate

[0026] Dissolve 2.0 g (13.83 mmol) of phenylhydrazine hydrochloride and 1.47 g (9.22 mmol) of ethyl acetylacetonate in ethanol, and raise the temperature to reflux for 6 hours. TLC detected that the reaction was complete, and concentrated under reduced pressure to distill off the solvent. Then add water, extract with ethyl acetate, wash the organic layer with saturated brine, Na 2 SO 4 Let dry overnight. The desiccant was filtered off, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 1.62 g of white solid with a yield of 75.3%. 1 H NMR (400MHz, DMSO-d 6 )δ: 7.59~7.54(m,5H),6.73(s,1H),4.32(q,J=7.1Hz,2H),2.35(s,3H),1.31(t,J=7.1Hz,3H).

[0027] (2) Synthesis of 3-chloromethyl-5-methyl-1-phenyl-1H-pyrazole

[0028] The intermediate 5-methyl-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester (1.5g, 6.51mmol) wa...

Embodiment 2

[0035]

[0036] 1H-NMR (600MHz, DMSO-d 6 )δ7.58(d,J=7.5Hz,2H),7.36(d,J=7.4Hz,2H),7.01–6.84(m,3H),6.64(s,1H),5.21(s,2H), 3.61(s,2H),3.32(t,J=7.1Hz,1H),2.44–2.34(m,2H),2.32(s,3H),1.96–1.63(m,4H).

Embodiment 3

[0038]

[0039] 1 H-NMR (600MHz, DMSO-d 6 )δ7.52(d,J=7.4Hz,2H),7.26(d,J=7.4Hz,2H),6.97–6.84(m,3H),6.66(s,1H),5.22(s,2H), 3.62(s,2H),3.36(t,J=7.1Hz,1H),2.48(s,3H),2.45–2.34(m,2H),2.32(s,3H),1.98–1.61(m,4H) .

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the technical field of medicine, and provides a phenyl-1H-pyrazole derivative as shown in the general formula and a preparation method thereof. The invention also discloses that the phenyl-1H-pyrazole derivative can Inhibit the mutual binding of programmed cell death receptor 1 / programmed cell death ligand 1 (PD‑1 / PD‑L1), which can be used to prepare PD‑1 / PD‑L1 inhibitors,

Description

technical field [0001] The invention belongs to the technical field of medicines, and relates to a new class of phenyl-1H-pyrazole derivatives, pharmaceutically acceptable salts, hydrates, solvates or prodrugs of the compounds, their preparation methods and their use as PD -1 / PD-L1 inhibitors. Background technique [0002] Malignant tumors are a global problem that seriously endangers human life and health. In 2010, WHO announced that by 2030, approximately 13.2 million people worldwide will die of cancer, which is twice the figure in 2008. The cancer situation in China is very serious. Every year, the total number of cancer deaths in the world reaches more than 9 million people, of which about 24% occur in China, and about 13% of Chinese cancer patients survive and are cured. Since the 1970s, the mortality rate of cancer in my country has been on the rise. In the 1970s, 1990s and early 21st century, the number of people who died of cancer was about 700,000, 1.17 million a...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/12A61P35/00A61K31/4155
CPCA61P35/00C07D403/12
Inventor 颜建发
Owner GUANGZHOU HANDY BIOTECH CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com