Phenyl-1H-pyrazole derivative and application thereof in antitumor drugs

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

Active Publication Date: 2020-06-26
GUANGZHOU HANDY BIOTECH CO LTD
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  • 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

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  • Phenyl-1H-pyrazole derivative and application thereof in antitumor drugs
  • Phenyl-1H-pyrazole derivative and application thereof in antitumor drugs
  • Phenyl-1H-pyrazole derivative and application thereof in antitumor drugs

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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) .

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Abstract

The invention belongs to the technical field of medicines, and provides a phenyl-1H-pyrazole derivative shown as a general formula and a preparation method thereof. The invention also discloses that the phenyl-1H-pyrazole derivative can inhibit the mutual combination of a programmed cell death receptor 1 / a programmed cell death ligand 1 (PD-1 / PD-L1) and can be used for preparing a PD-1 / PD-L1 inhibitor.

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

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Application Information

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IPC IPC(8): C07D403/12A61P35/00A61K31/4155
CPCA61P35/00C07D403/12
Inventor 颜建发
Owner GUANGZHOU HANDY BIOTECH CO LTD
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