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Cyclic compounds inhibiting programmed death receptor ligand 1 and uses thereof

A compound and application technology, applied to the compound of PD-L1 inhibitor, the above-mentioned compound-level pharmaceutical composition field, can solve problems such as side effects and poor therapeutic activity of solid tumors, and achieve low production cost, novel structure and convenient preparation. Effect

Active Publication Date: 2021-05-04
GUANGZHOU WELLHEALTH BIO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the half-life of monoclonal antibodies as long as 15-20 days may cause side effects related to immune response
Moreover, the current PD-1 / PD-L1 monoclonal antibody drugs need to be injected intravenously, and the therapeutic activity for solid tumors is not good

Method used

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  • Cyclic compounds inhibiting programmed death receptor ligand 1 and uses thereof
  • Cyclic compounds inhibiting programmed death receptor ligand 1 and uses thereof
  • Cyclic compounds inhibiting programmed death receptor ligand 1 and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1: Compound 1

[0057]

[0058] first step:

[0059]

[0060] Compound 1a (60.0g, 368mmol) was mixed with water (250mL), 1,4-dioxane (250mL) to obtain the first mixture, sodium carbonate (78g, 736mmol) and Cbz-Cl (68.6g, 405mmol ) was added to the first mixture, and stirred at room temperature for 9 hours. The reaction was confirmed to be complete by TLC analysis. The reaction mixture was diluted with water and washed with dichloromethane, the aqueous layer was acidified to pH 2-3 and extracted with dichloromethane. The organic layer was washed with water, brine, anhydrous Na 2 SO 4 It was dried and concentrated under reduced pressure to obtain 79 g of compound 1b. ESI-MS (m / z): 298 (M+1) + .

[0061] Step two:

[0062]

[0063] Compound 1c (3.7 g, 10 mmol) and compound 1d (3.4 g, 10 mmol) were added to anhydrous THF (60 mL) to obtain a second mixture. At 0°C, add N,N-diisopropylethylamine (DIPEA) into the above second mixture, after dropping, ...

Embodiment 2

[0074] Example 2: Compound 2

[0075]

[0076] ESI-MS (m / z): 516 (M+1) + .

Embodiment 3

[0077] Example 3: Compound 3

[0078]

[0079] ESI-MS (m / z): 544 (M+1) + .

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Abstract

The present invention proposes a cyclic compound for inhibiting programmed death receptor ligand 1 and its use. The compound is a compound shown in formula I or a pharmaceutically acceptable salt, hydrate, solvate, metabolite, stereoisomer or prodrug of the compound shown in formula I, wherein, R 1 , R 2 , R 3 as defined in the specification. The compound can be used as a small-molecule PD-L1 inhibitor to be prepared as a drug for treating and / or preventing tumors.

Description

technical field [0001] The present invention belongs to the field of biomedicine. Specifically, the present invention relates to a cyclic compound that inhibits programmed death receptor ligand 1 (PD-L1) and its use, and specifically relates to a compound as a PD-L1 inhibitor. Pharmaceutical composition, and the purposes of above-mentioned compound grade pharmaceutical composition. Background technique [0002] The PD-1 / PD-L1 signaling pathway is one of the hottest topics in the field of cancer treatment and research. New immunotherapy drugs that have been approved for marketing in the past two years, such as Merck’s Keytruda and Bristol-Myers Squibb’s Opdivo, all target this signaling pathway, using monoclonal antibodies to bind to PD-1 receptors to prevent signal transmission, thereby activating the body’s own immunity The system launches an attack on the tumor. The two new drugs are already approved to treat cancers such as melanoma, and have shown great promise in clin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/08A61K31/4245A61P35/00
CPCC07D498/08
Inventor 许勇黄璐胡海林当
Owner GUANGZHOU WELLHEALTH BIO PHARMA CO LTD
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