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ido inhibitor

A technology selected from and compounds, applied in the field of IDO inhibitors, can solve problems such as frequent administration, short half-life, and unmet medical needs of IDO inhibitors

Active Publication Date: 2021-09-03
CSTONE PHARM (SUZHOU) CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, existing clinical IDO inhibitors have problems such as CYP inhibition (NLG0919), large dosage, short half-life, and frequent administration (INCB-24360)
Therefore, IDO inhibitors without the above disadvantages are still an unmet medical need

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104]

[0105]

[0106] Synthesis of compound 1-c

[0107] Compound 1-a (10 g, 59.88 mmol, 6.62 mL) was dissolved in MeCN (100 mL), and 1-b (10.80 g, 239.52 mmol, 15.67 mL) was added in portions at 20 °C, K 2 CO 3 (24.83 g, 179.64 mmol). The resulting mixture was stirred at 20° C. for 12 hours under nitrogen protection. After filtering the reactant, the filtrate was concentrated under reduced pressure to obtain compound 1-c.

[0108] Synthesis of compound 1-e

[0109] Compound 1-c (6 g, 45.74 mmol) was dissolved in DCM (60 mL), and TEA (13.89 g, 137.22 mmol, 19.10 mL) was added to the solution at 20 °C. And 1-d was added at 0 °C ( 7.46g, 45.74mmol, 4.78mL), the resulting mixture was stirred at 20°C for 1 hour under nitrogen protection. The reaction solution was extracted with DCM (75mL×2) to remove organic impurities. The resulting organic phases were mixed and washed with saturated NH 4 Cl (50mL×3), washed with Na 2 SO 4 After drying, filtration and spin-drying, ...

Embodiment 2

[0126]

[0127] Synthesis of compound 2-a

[0128] Compound 1-j (500 mg, 2.81 mmol) was dissolved in THF (10 mL), and TEA (851.52 mg, 8.42 mmol, 1.17 mL) and Boc 2 O (642.80 mg, 2.95 mmol, 676.63 μL). The resulting mixture was stirred at 25°C under nitrogen for 12 hours. Saturated NH 4 Cl (15 mL) was added to the solution, and the mixture was extracted with EtOAc (15 mL×3) to remove organic impurities. The resulting organic phases were combined and washed with saturated NH 4 Cl (15 mL). 4 Cl (15mL×3) washed Na 2 SO 4 After drying, filtration and spin-drying, the crude product 2-a was obtained.

[0129] Synthesis of compound 2-b

[0130] Compound 2-a (500mg, 1.80mmol) was dissolved in THF (5mL), replaced with nitrogen three times, and n-BμLi (2.5M, 3.59mL) was slowly added to the solution at -70°C. The resulting mixture was stirred at -70°C for 1 hour. Then MeI (5.10 g, 35.92 mmol, 2.24 mL) was added at this temperature. The obtained mixed solution was reacted at 25° C...

Embodiment 3

[0139]

[0140] Synthesis of compound 3-b

[0141] Add potassium carbonate (24.83g, 179.64mmol) and compound 3-a (10.62g, 179.64mmol, 15.43mL) in the acetonitrile solution (100mL) of compound 1-a (10g, 59.88mmol, 6.62mL), at 25 ℃ After 12 hours of reaction, the suspension remained colorless. After adding 200 ml of ethyl acetate, it was filtered, and the filtrate was concentrated to obtain compound 3-b.

[0142] Synthesis of Compound 3-c

[0143] To a solution of compound 3-b (8.2 g, 56.47 mmol) in dichloromethane (100 mL) was added triethylamine (17.14 g, 169.42 mmol, 23.58 mL). After cooling the solution to 0°C, compound 1-d (9.21g, 56.47mmol, 5.90mL) was added dropwise, and reacted at 25°C for 12 hours after the dropwise addition, the color of the mixture changed from colorless to brown. 100 ml of dichloromethane was added, and the mixture was washed three times with 200 ml of saturated aqueous ammonium chloride solution, dried over anhydrous sodium sulfate, filtered, ...

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PUM

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Abstract

The invention discloses a new class of compounds as IDO inhibitors, and specifically discloses compounds represented by formula (I) and pharmaceutically acceptable salts thereof.

Description

[0001] This application claims the following priority: [0002] CN201711375318.8, the filing date is December 19, 2017. technical field [0003] The present invention relates to a new compound as an IDO inhibitor, and specifically discloses a compound represented by formula (I) and a pharmaceutically acceptable salt thereof. The present invention also relates to the application of the compound represented by formula (I) and the pharmaceutically acceptable salt thereof in the preparation of drugs for treating tumors. Background technique [0004] Malignant tumors are one of the major diseases that endanger human life today. In the past hundred years, in order to fight against malignant tumors, human beings have developed a variety of diagnosis and treatment methods including the most commonly used chemotherapy, surgery, radiotherapy and targeted therapy. These therapies delay the development of tumors to a certain extent and prolong the lives of patients. However, due to t...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D243/08A61K31/554A61K31/4353A61P35/00
CPCA61K31/4353A61K31/554A61P35/00C07D243/08C07D487/04
Inventor 周明陆剑宇胡国平丁照中黎健陈曙辉
Owner CSTONE PHARM (SUZHOU) CO LTD
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