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Aryl difluorobenzyl ether type compound as well as preparation method and purpose thereof

A technology of compounds and mixtures, applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc.

Active Publication Date: 2019-09-17
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, Krzysztof M. Zak et al. published the crystal structure of BMS-202 / PD-L1 in 2016, but so far only the inhibitory activity of PD1 / PD-L1 binding has been reported for this type of compound, and there are no in-depth reports on cells, etc. in vitro and in vivo

Method used

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  • Aryl difluorobenzyl ether type compound as well as preparation method and purpose thereof
  • Aryl difluorobenzyl ether type compound as well as preparation method and purpose thereof
  • Aryl difluorobenzyl ether type compound as well as preparation method and purpose thereof

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Experimental program
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Embodiment Construction

[0037] After long-term and in-depth research, based on the existing small molecule inhibitors targeting PD1 / PD-L1 and the crystal structure of PD-L1, the inventors introduced difluoro substitution at the position of the benzyl ether structure, thereby improving the interaction with PD-L1. Affinity and metabolic stability, based on the above findings, the inventors have completed the present invention.

[0038] the term

[0039] As used herein, the term "C1-C8 alkyl" refers to a straight chain or branched chain alkyl group with 1 to 8 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, or similar groups.

[0040] As used herein, the term "C2-C8 acyl" refers to a substituent in the form of a "straight-chain or branched chain alkyl-carbonyl group having 1 to 8 carbon atoms", such as acetyl, propionyl, butyryl, or the like group.

[0041] The term "6-membered aryl" refers to phenyl.

[0042] The term "5-7 membered heteroaryl" refers ...

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Abstract

The invention provides an aryl difluorobenzyl ether type compound as well as a preparation method and a purpose thereof. Concretely, the invention provides a compound shown as a formula I shown in the accompanying drawing, or pharmacologically acceptable salt, and a raceme, an R-isomer, an S-isomer and medicinal salt or mixtures thereof. The compound shows a better binding inhibition effect than the existing PD-1 inhibition compound in PD-1 / PD-L1 competition suppression experiments, so that the compound can be used for preparing a medicine combination for treating diseases relevant to a PD-1 / PD-L1 binding channels.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry. Specifically, the present invention provides a class of aryl difluorobenzyl ether compounds that can be used as PD-1 inhibitors, a preparation method and application thereof. Background technique [0002] Programmed cell death protein 1 (PD-1), an immune co-inhibitory molecule, is a member of the CD28 family, a type I transmembrane glycoprotein composed of 268 amino acids, and the same gene as CD28 and CTLA The molecule is distinct in that it is specifically expressed only on T cells. In a normal body, PD-1, as a negative regulator of T cell proliferation, plays an important role in maintaining the body's immune tolerance. Programmed death receptor 1 ligand 1 (PD-L1, also known as CD274) is also a type I transmembrane protein, which belongs to the B7 family of transmembrane molecules and is highly selectively expressed in tumors. When T cell receptors are activated, PD-1 binds to PD-L...

Claims

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Application Information

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IPC IPC(8): C07D319/18C07D405/12C07D413/12C07H15/26C07H15/18C07H1/00A61K31/357A61K31/4433A61K31/4245A61K31/7048A61P31/12A61P35/00
CPCC07D319/18C07D405/12C07D413/12C07H15/26C07H15/18C07H1/00
Inventor 张翱耿美玉宋子兰艾菁顾王婷刘博丁健
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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