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Pomalidomide derivative and application thereof

A technology of pomalidomide and derivatives, applied in the field of pomalidomide derivatives, can solve the problems of unsatisfactory PD-1/PD-L1 inhibition effect and the like

Pending Publication Date: 2020-06-19
SOUTHERN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the inhibitory effect of the compounds disclosed in the above PCT patent application on PD-1 / PD-L1 is not satisfactory, and the IC detected by HTRF method 50 Only 146nM

Method used

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  • Pomalidomide derivative and application thereof
  • Pomalidomide derivative and application thereof
  • Pomalidomide derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment 1 (compound preparation and identification thereof)

[0059] The pomalidomide derivatives of the present invention can be prepared by one of the following methods:

[0060] Preparation method one: aryl benzyl bromide compound (1 equivalent), borate (1.2 equivalent), cesium carbonate (1.2 equivalent) and tetrakistriphenylphosphine palladium (0.1 equivalent) are weighed and placed in dimethyl methylene In a mixed solvent of sulfone and water, the reaction was performed at 100°C for 12 hours after nitrogen replacement three times. After the reaction was completed, the reaction mixture was poured into water, extracted with ethyl acetate, the organic phase was washed with brine three times, dried with anhydrous sodium sulfate, and passed through a silica gel column to obtain the target product.

[0061] Preparation method 2: In an ice bath, add boron tribromide dropwise to the dichloromethane solution of aryl benzyl alcohol. After the reaction was completed, the...

Embodiment 2

[0088] Example 2. Research on the inhibitory effect of a pomalidomide derivative according to the present invention on PD-1 / PD-L1

[0089] The inhibitory effect of the compound of the present invention on PD-1 / PD-L1 is proved by the following method test.

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PUM

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Abstract

The invention relates to a pomalidomide derivative. The chemical structure of the pomalidomide derivative is shown as the following formula (I), in the formula (I), R1 is phenyl or 1, 4-benzodioxane,R2 is chlorine or bromine, R3 is hydrogen or a 3-methylbenzonitrile group, and X is a linking group selected from ethylenediamine, propane diamine, butanediamine, pentanediamine, hexamethylenediamine,piperazine succinic acid, piperazine glutaric acid, piperazine diglycolic acid, ethylenediamine succinic acid, ethylenediamine glutaric acid, ethylenediamine diglycolic acid, propane diamine glutaricacid, butanediamine glutaric acid or pentanediamine malonic acid. The pomalidomide derivative disclosed by the invention can inhibit the mutual combination of a programmed cell death receptor 1 / a programmed cell death ligand 1 (PD-1 / PD-L1), can be used for preparing a PD-1 / PD-L1 inhibitor, and has a remarkable effect.

Description

technical field [0001] The present invention relates to organic compounds, in particular to a pomalidomide derivative, which can inhibit the mutual binding of programmed cell death receptor 1 / programmed cell death ligand 1 (PD-1 / PD-L1), Can be used to treat tumors. Background technique [0002] Tumor immunotherapy is increasingly used in the field of cancer treatment. At present, the main drugs used in tumor immunotherapy are macromolecular biological antibodies. Among them, inhibitors of PD-1 / PD-L1 (also known as immune checkpoint inhibitors) are effective for a variety of tumors. Therefore, in recent years, PD-1 / PD-L1 has become the most attractive target in the design of anti-tumor drugs, and has also been listed as one of the most promising targets for tumor treatment, so it has attracted much attention. [0003] PD-1 / PD-L1 antibody drugs have the advantages of target-specific specificity and high efficiency in terms of their pharmacodynamics. However, in terms of it...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D405/14A61P35/00A61K31/4545A61K31/496
CPCC07D401/14C07D405/14A61P35/00
Inventor 陈建军程斌斌任益昌
Owner SOUTHERN MEDICAL UNIVERSITY
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