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Five-membered heterocycle substituted biphenyl compound and preparation method and application thereof

A technology of five-membered heterocycles and compounds, which is applied in the field of five-membered heterocycles substituted biphenyl compounds and their preparation, can solve the problems of expensive production and limited range of tumor treatment, facilitate industrial production, and solve treatment and drug resistance , prepare simple effects

Active Publication Date: 2021-07-16
YAOKANG ZHONGTUO (JIANGSU) PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Purpose of the invention: In view of the shortcomings of existing PD-1 / PD-L1 monoclonal antibody drugs such as expensive production, need for injection, and limited tumor treatment range, this application provides a PD-1 / PD-L1 small molecule inhibitor compound and Its preparation method and application

Method used

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  • Five-membered heterocycle substituted biphenyl compound and preparation method and application thereof
  • Five-membered heterocycle substituted biphenyl compound and preparation method and application thereof
  • Five-membered heterocycle substituted biphenyl compound and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047]

[0048] synthetic route:

[0049]

[0050] Synthesis of Compound 1-A

[0051] The compound 3-aminobenzyl alcohol (2 g) and triethylenediamine (5.38 g) were dissolved in 50 mL of acetone. After stirring at room temperature for 10 min, 10 mL of carbon disulfide was added dropwise, and the stirring was continued for one hour at room temperature. TLC monitored the complete reaction of the raw materials. Filter, wash the filter cake with petroleum ether, collect the filter cake, dry it and dissolve it in 50 mL of chloroform, stir at room temperature, and under the condition of nitrogen protection, dissolve triphosgene (1.43 g) in 10 mL of chloroform and add dropwise to react overnight. The reaction of raw materials was monitored by TLC, and the insoluble matter was filtered off. The filtrate was concentrated and purified by column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain compound 1-A (1.02 g) as a white solid.

[0052] Synthesis of Compound 1-B...

Embodiment 2

[0071]

[0072] Referring to the synthesis method of Example 1, compound 2 can be prepared by replacing ethanolamine with glycine. 1 H NMR (300MHz, Methanol-d 4 )δ7.97–7.91(m,2H),7.60(s,2H),7.54–7.46(m,4H),7.38(t,J=7.8Hz,4H),7.09(d,J=7.6Hz,2H ),3.84(s,4H),3.45(s,4H),2.40(s,6H).

Embodiment 3

[0074]

[0075]Referring to the synthesis method of Example 1, compound 3 can be prepared by replacing ethanolamine with N-(2-aminoethyl)acetamide. 1 H NMR (300MHz, Methanol-d 4 )δ7.93(dd, J=7.6Hz, 1.2Hz, 2H), 7.64–7.47(m, 6H), 7.35(t, J=7.1Hz, 4H), 7.14(d, J=6.5Hz, 2H) ,3.91(s,4H),3.67(t,J=5.1Hz,4H),3.17–3.06(m,4H),2.38(s,6H),1.87(s,2H).

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Abstract

The invention discloses an immune checkpoint inhibitor five-membered heterocycle substituted biphenyl compound capable of blocking a PD-1 / PD-L1 signal pathway and a preparation method and application thereof. The compound is shown in the formula I as described in the specification. The compound is novel in structure and can be orally taken, the defects of treatment and drug resistance of a monoclonal antibody immune checkpoint inhibitor are overcome, and as a small-molecule inhibitor, the preparation is simple, and industrial production is convenient; various related tumor diseases can be treated through tumor immunotherapy by regulating and controlling a PD-1 / PD-L1 signal pathway, and potential patent medicine prospects are achieved.

Description

technical field [0001] The application belongs to biomedical technology, and specifically relates to a biphenyl compound substituted by a five-membered heterocycle and its preparation method and application. Background technique [0002] Malignant tumors are a class of diseases that seriously threaten human health and life. Currently, tumor treatments include surgery, radiotherapy, chemotherapy, and targeted therapy. Tumor immunotherapy refers to a treatment method that stimulates the body's immune system to improve the anti-tumor immune effect, thereby inhibiting and killing tumor cells. The research on immunotherapy has a history of nearly a hundred years. With the comprehensive development and cross-infiltration of oncology, immunology and molecular biology, immunotherapy has achieved various results and brought new hope for tumor treatment. [0003] Immune checkpoint inhibitors are currently the hottest immunotherapy drugs. Tumor cells can inhibit the activity of immu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/113C07D413/14C07D271/07C07D413/10C07D285/135A61K31/4245A61K31/433A61P35/00
CPCC07D271/113C07D413/14C07D271/07C07D413/10C07D285/135A61P35/00
Inventor 蒋晟肖易倍郝海平王天雨张阔军王敏敏邱亚涛章翔宇
Owner YAOKANG ZHONGTUO (JIANGSU) PHARMA TECH CO LTD
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