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Hepatitis B virus surface antigen inhibitor

A technology of atoms and carbon atoms, applied in the field of hepatitis B virus surface antigen inhibitors, can solve the problem of poor water solubility of 7-membered carbon rings

Active Publication Date: 2018-11-23
푸지엔에이키링크바이오테크놀로지컴퍼니리미티드
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally, the 7-membered carbon ring has poor water solubility and is prone to oxidative metabolism

Method used

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  • Hepatitis B virus surface antigen inhibitor
  • Hepatitis B virus surface antigen inhibitor
  • Hepatitis B virus surface antigen inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0181]

[0182] Step A: 1-1 (200.00 g, 1.19 mol) was dissolved in N,N-dimethylformamide (1000.00 ml), potassium carbonate (164.39 g, 1.19 mol) was added, and then added dropwise at 90°C for one hour 1-Bromo-3-methoxy-propane (182.01 g, 1.19 mol). The mixture was stirred at 90°C for 15 hours. Add 3 liters of ethyl acetate (1 liter × 3) to the reaction solution, combine the organic phases, wash with 15.00 liters of water (3.00 liters × 5), and 3.00 liters of saturated brine (1.00 liters × 3), and dry over anhydrous sodium sulfate , and concentrated under reduced pressure to obtain a crude product. Then purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=1 / 0) to obtain compound 1-2.

[0183] Step B: 1-2 (80.00 g, 332.98 mmol) was dissolved in acetonitrile (800.00 mL), then chlorosuccinimide (44.46 g, 332.98 mmol) was added and the mixture was stirred at 90°C for three hours. First spin off half the volume of acetonitrile, then add 200.00 ml o...

Embodiment 2

[0199]

[0200] ee value (enantiomeric excess): 100%.

[0201] SFC (Supercritical Fluid Chromatography) Method: Column: Chiral pak AD-3 100 mm x 4.6 mm I.D., 3 microns. Mobile phase: methanol (0.05% diethylamine) from 5% to 40% in carbon dioxide. Flow rate: 3 ml per minute. Wavelength: 220 nm.

[0202] 1 H NMR (400MHz, deuterated chloroform) δ15.77(br s, 1H), 8.49(s, 1H), 7.52(s, 1H), 6.87(s, 1H), 6.68(s, 1H), 4.49-4.72 (m, 2H), 4.12-4.28(m, 2H), 3.92(br d, J=6.40Hz, 1H), 3.63(t, J=5.90Hz, 2H), 3.39(s, 3H), 2.06-2.24 (m, 3H), 1.10 (d, J=6.53Hz, 3H), 0.89 (d, J=6.53Hz, 3H).

Embodiment 3

[0204]

[0205] ee value (enantiomeric excess): 100%.

[0206] SFC (Supercritical Fluid Chromatography) Method: Column: Chiral pak AD-3 100 mm x 4.6 mm I.D., 3 microns. Mobile phase: methanol (0.05% diethylamine) from 5% to 40% in carbon dioxide. Flow rate: 3 ml per minute. Wavelength: 220 nm.

[0207] 1 H NMR (400MHz, deuterated chloroform) δ15.81(s, 1H), 8.88-9.18(m, 1H), 7.47(s, 1H), 6.78(s, 1H), 6.76(s, 1H), 4.48- 4.59(m, 2H), 4.19(dt, J=2.07, 6.12Hz, 2H), 3.59-3.67(m, 2H), 3.45-3.52(m, 1H), 3.39(s, 3H), 2.15(quin, J=6.05Hz, 2H), 1.14-1.31(m, 2H), 0.29-0.55(m, 2H), 0.09(s, 1H).

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Abstract

The invention discloses a novel 11-oxo-7, 11-dihydride-6H-benzo [f] pyrido [1, 2-d] [1, 4] azepine-10-carboxylic acid derivative as a hepatitis B virus surface antigen inhibitor, and concretely discloses compounds represented by formula (V) or pharmaceutically acceptable salts thereof, and applications of the compounds represented by formula (V) or pharmaceutically acceptable salt and pharmaceutically acceptable compositions in the treatment of viral hepatitis B.

Description

[0001] Cross References to Related Applications [0002] This application claims the priority of Chinese patent application 201710365328.7 filed on May 22, 2017, the content of which is hereby incorporated into this application. technical field [0003] The present invention relates to novel 11-oxo-7,11-dihydro-6H-benzo[f]pyrido[1,2-d][1,4]azepine- 10-carboxylic acid derivatives, specifically related to compounds shown in formula (V) or pharmaceutically acceptable salts thereof, and compounds shown in formula (V) or pharmaceutically acceptable salts and pharmaceutical compositions in the treatment of type B Application in viral hepatitis. Background technique [0004] Hepatitis B virus, referred to as hepatitis B, is a disease caused by hepatitis B virus (Hepatitis B Virus, HBV) infection after the body. Hepatitis B virus is a hepatotropic virus that mainly exists in liver cells and damages liver cells, causing inflammation, necrosis, and fibrosis of liver cells. There ar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/04A61P1/16A61K31/553
CPCA61P1/16C07D498/04
Inventor 丁照中孙飞胡彦宾陈曙辉
Owner 푸지엔에이키링크바이오테크놀로지컴퍼니리미티드
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