Novel Indoleamine 2,3-Dioxidase Inhibitors

A compound and selected technology, applied in the field of anti-tumor drugs, can solve problems such as the inability to directly regulate the immune response system of immune cells, and achieve obvious pharmacokinetic absorption effects, high medicinal value, and excellent comprehensive effects

Active Publication Date: 2022-04-22
NANJING HUAWE MEDICINE TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Traditional tumor therapies are all macromolecule or cell therapy, which target cell surface receptors and cannot directly regulate the large and complex immune response system in immune cells

Method used

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  • Novel Indoleamine 2,3-Dioxidase Inhibitors
  • Novel Indoleamine 2,3-Dioxidase Inhibitors
  • Novel Indoleamine 2,3-Dioxidase Inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0142] Example 1 Synthesis of Compound I-1

[0143]

[0144] Take 0.3g of m-phenylenediamine, add 10ml of ethyl acetate to dissolve it, add 0.9g of compound 1, stir at room temperature, TLC detects that the raw materials have reacted completely, add a few drops of triethylamine to the reaction solution, add 50ml of water, and dissolve with ethyl acetate. Ester extraction (20ml*3), the organic phases were combined, dried over anhydrous sodium sulfate and then reduced to dryness under reduced pressure, and 40 mg of yellow solid I-1 was obtained by column chromatography.

Embodiment 2

[0145] Embodiment 2 compound I-2 is synthesized

[0146]

[0147] Take 0.3g of p-phenylenediamine, add 10ml of ethyl acetate to dissolve it, add 0.9g of compound 1, stir at room temperature, TLC detects that the raw materials have reacted completely, add a few drops of triethylamine to the reaction solution, add 50ml of water, and dissolve with ethyl acetate. Ester extraction (20ml*3), the organic phases were combined, dried over anhydrous sodium sulfate and then reduced to dryness under reduced pressure, and 30mg of yellow solid I-2 was obtained by column chromatography.

Embodiment 3

[0148] Embodiment 3 compound I-16 is synthesized

[0149]

[0150] Step 1. Take 405mg p-aminophenylboronic acid, 400mg 2-amino-5-bromo-3-methoxypyrazine, 552mg potassium carbonate, 30mg tetrakistriphenylphosphine palladium, 10ml DMF and 1ml water, replace nitrogen, and heat up to React at 100°C overnight, TLC detects that the reaction of the raw materials is complete, cool down to room temperature, add water and ethyl acetate, separate the layers, dry the organic phase with anhydrous sodium sulfate and reduce to dryness under reduced pressure, and obtain 100 mg of compound I-16-1 by column chromatography .

[0151]Step 2. Take 100mg of compound I-16-1, add 10ml of DMF to dissolve it, add 190mg of compound 1, stir at room temperature, TLC detects that the raw materials have reacted completely, add a few drops of triethylamine dropwise to the reaction solution, add 50ml of water, and dissolve with acetic acid Extract with ethyl ester (20ml*3), combine the organic phases, d...

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PUM

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Abstract

The invention provides a novel indoleamine 2,3-dioxygenase inhibitor, a preparation method thereof, and a pharmaceutical composition, wherein the definitions of R and X groups are as shown in the description. Also provided is the use of the compound and its pharmaceutically acceptable salts and isomers in the preparation of drugs for diseases related to indoleamine 2,3-dioxygenase (IDO), specifically in the Applications in the treatment of cancer, Alzheimer's disease, depression, cataracts and many other major diseases. The compound of the invention has good activity, has potential medical value and broad market prospects.

Description

technical field [0001] This field belongs to the field of antitumor drugs, and specifically relates to a highly efficient IDO inhibitor and its preparation method and application. Background technique [0002] Traditional tumor therapies are all macromolecular or cell therapies, which target cell surface receptors and cannot directly regulate the large and complex immune response system in immune cells. There are many immunosuppressive molecules in the tumor microenvironment. Immunotherapy strategies that improve the tumor immune microenvironment by regulating the functions of these inhibitory molecules are called immunotherapy. Some nodes of this regulatory system involving hundreds of proteins may be related to PD. -1 has a similar function or has a synergistic effect with PD-1 antibodies, and these targets are most suitable for regulation by small molecule drugs. Therefore, immunotherapy is also known as a breakthrough in the history of tumor treatment. [0003] Indolea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/08C07D413/12C07D413/14C07D487/04A61K31/4245A61K31/497A61K31/444A61K31/506A61P35/00A61P25/28A61P25/24A61P27/12
CPCC07D271/08C07D413/12C07D413/14C07D487/04A61K31/4245A61K31/444A61K31/497A61K31/506A61P25/24A61P25/26A61P25/28A61P27/12A61P35/00
Inventor 张孝清宋志春包金远
Owner NANJING HUAWE MEDICINE TECH DEV
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