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Substituted phenyl compound and application thereof

A compound, phenyl technology, applied in the field of substituted phenyl compounds, can solve problems such as low bioavailability, need for intravenous injection, and poor therapeutic activity for solid tumors

Active Publication Date: 2019-08-06
GUANGZHOU WELLHEALTH BIO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is that the existing PD-1 / PD-L1 monoclonal antibody drug needs intravenous injection, has poor therapeutic activity on solid tumors, and has defects such as low bioavailability. Therefore, the present invention provides a Substituted phenyl compounds and their applications

Method used

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  • Substituted phenyl compound and application thereof
  • Substituted phenyl compound and application thereof
  • Substituted phenyl compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0122] Preparation of Example 1 Compound I-2

[0123]

[0124] (1) Preparation of compound I-2-2

[0125]

[0126] Compound I-2-1 (4.3 g, 31.13 mmol), 1-chloromethyl-4-fluoro-1,4-diazobicyclo 2.2.2 octane bis(tetrafluoroborate) salt (15 g, 42.34 mmol) was added to a 250mL single-neck bottle, acetonitrile (60mL) was added to react at room temperature for 5 days, the reaction system was spin-dried, and column chromatography gave compound I-2-2, yield 2.8g, yield 28.8%.

[0127] 1 H NMR (500MHz, CDCl 3 ): δ=11.22(s, 1H), 9.66(s, 1H), 7.24(d, J=5.0Hz, 1H), 6.58(d, J=5.0Hz, 1H).

[0128] (2) Preparation of compound I-2-4

[0129]

[0130] Compound I-2-3 (2.0 g, 14.91 mmol) was added to a 50 mL single-neck flask, thionyl chloride (6.5 mL) and dichloromethane (20 mL) were added to react at room temperature for 3 h, TLC detected that the reaction was complete, and the reaction system was Spin to dry and oil pump to dry to obtain compound I-2-4, the yield is 1.8 g, and th...

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PUM

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Abstract

The present invention discloses a substituted phenyl compound and an application thereof, and provides a substituted phenyl compound represented by formula I, or pharmaceutically acceptable salt, a hydrate, a solvate, a metabolite, a stereoisomer, a tautomer or a prodrug thereof. The compound I provided by the invention has the advantages of high activity, high bioavailability, stable drug and oral administration.

Description

technical field [0001] The invention belongs to the field of biomedicine and relates to a substituted phenyl compound and its application. Background technique [0002] PD-1 / PD-L1 signaling pathway is one of the hottest topics in the field of cancer treatment and research. New immunotherapy drugs approved for marketing in the past two years, such as Merck's Keytruda and Bristol-Myers Squibb's Opdivo, both target this signaling pathway, using monoclonal antibodies to bind to PD-1 receptors to block signal transmission, thereby activating the body's own immune system The system attacks the tumor. The two new drugs are already approved to treat cancers such as melanoma, and have shown great potential in clinical trials for a number of other cancers. At present, the US FDA has approved 3 macromolecular PD-L1 inhibitors to market, namely Atezolizumab (Tecentriq, the treatment of bladder cancer and non-small cell lung cancer, is the first PD-L1 inhibitor approved by FDA), Avelum...

Claims

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Application Information

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IPC IPC(8): C07D405/14C07D405/12C07D401/12C07D213/85C07D319/18C07D213/71C07D213/80A61K31/4545A61K31/4433A61K31/44A61K31/443A61K31/4025A61K31/36A61K31/453A61K31/444A61P35/00A61P37/02
CPCC07D405/14C07D405/12C07D401/12C07D213/85C07D319/18C07D213/71C07D213/80
Inventor 许勇林当黄璐胡海
Owner GUANGZHOU WELLHEALTH BIO PHARMA CO LTD
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