Indoleamine 2,3-dioxygenase inhibitor and uses thereof in pharmacy

A pharmaceutical, amine-based technology, applied in the field of chemical compounds, can solve problems such as weak level activity

Inactive Publication Date: 2018-02-16
SUZHOU GUOKUANG PHARMTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the measured enzyme level activity of these two derivatives to IDO was significantly weaker than that of NLG919

Method used

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  • Indoleamine 2,3-dioxygenase inhibitor and uses thereof in pharmacy
  • Indoleamine 2,3-dioxygenase inhibitor and uses thereof in pharmacy
  • Indoleamine 2,3-dioxygenase inhibitor and uses thereof in pharmacy

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0136] The preparation of prodrugs is well known in the art and described, for example, in King, F.D., ed., Medicinal Chemistry: Principles 15 and Practice, The Royal Society of Chemistry, Cambridge, UK (2nd edition, reproduced, 2006); Testa, B. et al., Hydrolysis in Drug and Prodrug Metabolism. Chemistry, Biochemistry and Enzymology, VCHA and Wiley-VCH, Zurich, Switzerland (2003); Wermuth, C.G., ed., The Practice, of Medicinal Chemistry, 3rd edition, Academic Press, San Diego, CA (2008).

[0137] The present invention is intended to include all isotopes of atoms present in the compounds of the present invention. Isotopes include atoms with the same atomic number but different mass numbers. By way of general example and not limitation, isotopes of hydrogen include deuterium and tritium. Isotopes of carbon include 13C and 14C. Isotopically-labeled compounds of the present invention may be prepared generally by conventional techniques known to those skilled in the art or by m...

Embodiment 1

[0217] Example 1 Preparation of 2-(1-trityl-1H-imidazol-4-yl)benzaldehyde

[0218]

[0219] 2-formylphenylboronic acid (1.55g, 6.88mmol), 1-trityl-4-iodoimidazole (3.0g, 4.59mmol), potassium phosphate (4.38g, 13.77mmol), Pd(PPh 3 ) 4 (0.3g, 10%, w / w%) was added to a mixed solution of DMF (30mL) and water (6mL), the system was replaced with nitrogen 4 times, and reacted overnight at 90°C under nitrogen protection. TLC detected that the reaction was complete, cooled to room temperature, filtered, the filtrate was diluted with ethyl acetate (300mL), washed with water (100mL) three times, the organic phase was evaporated under reduced pressure to remove the solvent, and the residue was separated by flash column chromatography to obtain 2.15g of the target product , the yield was 75.6%. 1 H NMR (CDCl 3 ,400MHz)δ10.44(s,1H),7.94 (dd,J 1 =0.8Hz,J 2 =0.8Hz,1H),7.65-7.63(m,1H),7.58-7.53(m,2H),7.40-7.36(m,10H),7.18-7.21(m,6H),7.04(d,J=1.2 Hz, 1H).

Embodiment 2

[0220] Example 2 Preparation of 1-(1-hydroxyl-4-phenylcyclohexyl)ethyl-1-one

[0221]

[0222] 4-Phenylcyclohexanone (0.26g, 1.5mmol) was dissolved in tetrahydrofuran (1.0mL), nitrogen was replaced three times, diiodine solution (0.1M in THF, 15mL, 1.5mmoL) was slowly added dropwise, and then Acetyl chloride (0.39g, 1.0mmoL) was slowly added dropwise to the reaction flask. After the drop was completed, the reaction was stirred overnight at room temperature. After the reaction was complete by TLC, it was quenched with 0.1M hydrochloric acid. Volatile substances were evaporated under reduced pressure, and the residue was separated by flash column chromatography to obtain 0.16 g of the target product with a yield of 52%. 1 H NMR (DMSO-d 6 , 400MHz) δ7.31-7.15 (m, 5H), 5.20 (s, 1H), 2.20 (s, 3H), 1.82-1.77 (m, 2H), 1.65-1.59 (m, 6H).

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Abstract

The invention relates to a compound, which is one or a plurality of indoleamine 2,3-dioxygenase inhibitors. The present invention further provides a pharmaceutical component containing the compound, apreparation containing the compound, and uses of the indoleamine 2,3-dioxygenase inhibitors, wherein the compound can be used for treating indoleamine 2,3-dioxygenase related symptoms through singlemedication or combination with other drugs.

Description

technical field [0001] The present invention relates to a compound, a method for preparing the compound, a pharmaceutical composition and a medicament of the compound, and the compound is used for treating, preventing, and diagnosing one or more diseases and disorders related to indoleamine 2,3-dioxygenase or symptoms. Background technique [0002] Tumor is the most deadly and disabling malignant disease in human beings. The current development trend of treatment in the field of tumors, tumor-related fields and functional disorders lies in the combination of tumor immunotherapy with traditional chemotherapy and radiotherapy. Compared with traditional chemotherapy, tumor immunotherapy recognizes and eliminates tumor cells as foreign invaders by activating the body's own immune system. Therefore, the tumor immune strategy has the remarkable characteristics of good clinical effect and less toxic side effects. At present, it is generally believed that tumor immunotherapy is th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D519/00C07F9/6561A61K31/4439A61K31/407A61K31/4709A61K31/416A61K31/4155A61K31/437A61K31/506A61K31/422A61K31/5377A61K31/675A61P35/00A61P35/02A61P35/04A61P31/12A61P37/06A61P37/02A61P31/18A61P31/14A61P25/28A61P11/06A61P19/02A61P29/00A61P37/08A61P17/06A61K45/06
Inventor 梅德盛刘爱风汪奎孙靖
Owner SUZHOU GUOKUANG PHARMTECH CO LTD
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