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Novel indoleamine 2,3-dioxygenase inhibitor

A compound and aryl technology, applied in the field of efficient IDO inhibitor and its preparation, can solve the problem of inability to directly regulate the immune cell immune response system, etc.

Active Publication Date: 2018-12-25
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-dioxygenase inhibitor
  • Novel indoleamine 2,3-dioxygenase inhibitor
  • Novel indoleamine 2,3-dioxygenase inhibitor

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 material has 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. Get 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 over 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, dr...

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PUM

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Abstract

The invention provides a novel indoleamine 2,3-dioxygenase inhibitor and a preparation method and a pharmaceutical composition thereof. Definitions of R and X groups are as shown in specification. Meanwhile, the invention provides a compound and application of pharmaceutically acceptable salts and isomer of the compound in preparation of drugs for treating diseases related to indoleamine 2,3-dioxygenase (IDO), and particularly relates to application of the drugs in treatment of various serious diseases such as cancers, a alzheimer disease, depression and cataract. The compound is good in activity, and has potential medicinal value and high marketing prospect.

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 Applications(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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