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Indoleamine 2,3-dioxygenase inhibitor

A solvate and compound technology, applied in the field of infectious diseases, treatment of proliferative diseases, immune-related diseases and/or inflammatory diseases, can solve problems such as immune tolerance does not work

Inactive Publication Date: 2020-12-11
QILU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The results suggest that although the IDO pathway plays an important role in the body's immune tolerance to foreign antigens, it does not seem to play a role in maintaining the body's immune tolerance to self-antigens

Method used

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  • Indoleamine 2,3-dioxygenase inhibitor
  • Indoleamine 2,3-dioxygenase inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0107] N-(4-chlorophenyl)-2-[3-(6-fluoroquinolin-4-yl)bicyclo[1.1.1]pentane-1-yl]propanamide 1 (enantiomer, peak 1)

Embodiment 2

[0109] N-(4-chlorophenyl)-2-[3-(6-fluoroquinolin-4-yl)bicyclo[1.1.1]pentane-1-yl]propanamide 2 (enantiomer, peak 2)

[0110]

[0111] synthetic route

[0112] first step:

[0113]

[0114]3-(Methoxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid (CAS#83249-10-9, 4.5g, 26.6mmol, 1.0equiv), 6-fluoroquinoline (1.9g, 13.3 mmol, 0.5equiv), silver nitrate (903mg, 5.3mmol, 0.2equiv), copper acetate (241mg, 1.3mmol, 0.05equiv), potassium persulfate (7.2g, 27mmol, 1.0equiv) were sequentially added to the 250mL reaction flask, and then added Acetonitrile (70 mL) and water (30 mL) were stirred uniformly at room temperature, then heated to 60° C. and stirred for 2.5 h. After the reaction is complete, cool down to room temperature, spin to remove acetonitrile, add a small amount of water to dilute, extract three times with ethyl acetate, combine the organic phase, dry the organic phase with anhydrous sodium sulfate for 15min, filter to remove anhydrous sodium sulfate, and spin th...

Embodiment 3

[0146] (±) 3-[1-[(4-chlorophenyl)carbamoyl]ethyl]-N-phenylbicyclo[1.1.1]pentane-1-carboxamide 3 (racemate)

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Abstract

The invention provides a novel compound capable of inhibiting activity of indoleamine 2,3-dioxygenase (IDO), a pharmaceutical composition containing the compound, a preparation method of the compoundand application of the compound in preparation of drugs for treating proliferative diseases, infectious diseases, immune-related diseases and / or inflammatory diseases.

Description

technical field [0001] The present invention relates to compounds that regulate or inhibit the activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds, and the use of compounds of the present invention to treat proliferative diseases (such as cancer), infectious diseases , A method for an immune-related disease and / or an inflammatory disease. Background technique [0002] Tryptophan is an essential amino acid for the human body. Part of the tryptophan obtained from the diet is used to synthesize protein and neurotransmitter 5-hydroxytryptamine, and the rest is mainly metabolized through the kynurenine pathway, which is metabolized through a series of steps to form Nicotinamide adenine dinucleotide (NAD+). Indoleamine 2,3-dioxygenase (IDO) is a heme-containing monomeric oxidoreductase that catalyzes the degradation of tryptophan to N-formyl-kynurenine, the kynurenine of tryptophan It is the first step in the amino acid metabolic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/18C07C233/58C07C233/81A61K31/47A61K31/167A61P35/00A61P31/00A61P37/02A61P29/00
CPCA61P29/00A61P31/00A61P35/00A61P37/02C07C233/58C07C233/81C07D215/18C07C2602/38C07C2603/52
Inventor 吴晓冉邓伟陈冬妹毛海滨林栋赵谈封杨莹莹郑善松付健民张薛赵树雍
Owner QILU PHARMA
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