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Compound adopted as hepatitis c inhibitor and application thereof in medicine

A compound and solvate technology, applied in the fields of drug combination, digestive system, organic chemistry, etc., can solve the problem of unclear clinical importance of HCV genetic heterogeneity, and achieve good inhibitory effect, good inhibitory effect, and good inhibitory activity. Effect

Active Publication Date: 2016-08-24
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The major genotypes of HCV have a variable global distribution, and although the role of genotypes in pathogenesis and therapy has been extensively studied, the clinical importance of HCV genetic heterogeneity remains unclear

Method used

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  • Compound adopted as hepatitis c inhibitor and application thereof in medicine
  • Compound adopted as hepatitis c inhibitor and application thereof in medicine
  • Compound adopted as hepatitis c inhibitor and application thereof in medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0316]

[0317] synthetic route:

[0318]

[0319] Step 1: Synthesis of compounds 1-3

[0320] Compound 1-2 (20 g, 150 mmol) and compound 1-1 (30 g, 170 mmol) were added into ethanol (100 mL), then heated to 75° C., and stirred at this temperature for two hours. After the reaction was complete, it was lowered to room temperature, and the ethanol solution was removed under reduced pressure, 100 mL of water was added to quench the reaction, and the pH value of the mixture was adjusted to between 6 and 8 with ammonia water. Then it was extracted twice with MTBE (100mL×2), the combined organic phase was washed twice with water (50mL×2), separated, and the resulting organic phase was concentrated under reduced pressure to obtain brownish red crude product 1-3, without Further purification directly proceeds to the next reaction.

[0321] MS(ESI,pos.ion)m / z:200.3[M+1] + .

[0322] Step 2: Synthesis of compounds 1-4

[0323] Compound 1-3 (28g, 140mmol) was added to methanol...

Embodiment 2

[0334]

[0335] synthetic route

[0336]

[0337] Step 1: Synthesis of Compound 2-3

[0338] Benzaldehyde 2-1 (95.6mL, 943mmol), glycine ethyl ester hydrochloride 2-2 (131g, 943mmol) and Na 2 SO 4 (80g, 565mmol) was added into 900ml TBME, then cooled to 0°C, and triethylamine (197mL, 1414mmol) was added slowly, then warmed up to 25°C, and stirred at this temperature for 24 hours. The mixture was passed through a column with celite to remove the solid, and the organic solvent in the filtrate was removed under reduced pressure, and the solvent was removed from the obtained residue under high vacuum to obtain quantitative crude product 2-3, which was directly carried out to the next reaction without further purification.

[0339] 1 H NMR (600MHz, CDCl 3 ):δ8.28(s,1H),7.86–7.71(m,2H),7.50–7.32(m,3H),4.47–4.32(m,2H),4.29–4.18(m,2H),1.32–1.22 (m,3H)ppm.

[0340] Step 2: Synthesis of compounds 2-4

[0341] Lithium tert-butoxide (17.60g, 220mmol) was added to 250ml of tol...

Embodiment 3

[0356]

[0357] synthetic route:

[0358]

[0359] Step 1: Synthesis of compound 3-3

[0360] Compound 3-1 (100g, 460.36mmol) and compound 3-2 (100g, 564.72mmol) were dissolved in 1L of acetonitrile, then cesium carbonate (90g, 276.219mmol) and potassium carbonate (40g, 289.427mmol) were added, and the reaction The mixture was warmed to reflux for 24 hours. Cool to room temperature, filter, and remove the organic solvent from the filtrate under reduced pressure to obtain the crude product 3-3, which is directly carried out to the next reaction without further purification. MS(ESI,pos.ion)m / z:314.4[M+1] + .

[0361] Step 2: Synthesis of Compound 3-5

[0362] Compound 3-3 (150g, 478.6mmol) was dissolved in ethanol (750mL), and then a solution of KOH (81g, 1443.72mmol) in water (75mL) was slowly added dropwise. After the dropwise addition, the temperature was raised to reflux for 4 hours. After the reaction was complete, ethanol was removed under reduced pressure, then...

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Abstract

The invention relates to a compound adopted as a hepatitis c inhibitor and application thereof in medicine, in particular to a compound shown in a formula (I), a stereoisomer, a tautomer, an enantiomer, a nitric oxide, a hydrate, a solvate, a metabolite and pharmaceutical acceptable salts or prodrugs of the compound shown in the formula (I). The compound is used for treating hepatitis c virus (HCV) infection or hepatitis c diseases. The invention further discloses a pharmaceutical composition comprising the compound and a method for using the compound or the pharmaceutical composition thereof for treating HCV infection or hepatitis c diseases.

Description

field of invention [0001] The present invention belongs to the field of medicine and relates to compounds for the treatment of hepatitis C virus (HCV) infection, compositions of said compounds, uses and methods of use thereof. In particular, the compounds of the present invention can be used to inhibit NS3 / 4A protease. More specifically, the present invention relates to a compound capable of inhibiting the function of NS3 / 4A protein encoded by hepatitis C virus, a pharmaceutical composition of the compound and a method for inhibiting the function of NS3 / 4A protein. Background of the invention [0002] HCV is a major human pathogen, estimated to infect approximately 170 million people worldwide, five times the number infected by human immunodeficiency virus type 1. Most of these HCV-infected individuals develop severe progressive liver disease, including cirrhosis and hepatocellular carcinoma. Thus, chronic HCV infection will be the leading cause of premature death from liv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/4709A61P1/16A61P31/14
CPCC07B2200/07C07D487/04A61K31/4709A61K45/06A61P1/16A61P31/14C07D471/04
Inventor 张英俊罗慧超任青云熊志敏刘洋雷义波熊金峰张健存
Owner SUNSHINE LAKE PHARM CO LTD
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