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Substituted prolines as inhibitors of hepatitis c virus NS3 serine protease

一种化合物、选自的技术，应用在抗病毒剂、肽/蛋白质成分、含有效成分的医用配制品等方向，能够解决HCV感染没有疫苗可用等问题

Inactive Publication Date: 2007-06-20
SCHERING AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, no vaccine is available for HCV infection

Method used

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  • Substituted prolines as inhibitors of hepatitis c virus NS3 serine protease
  • Substituted prolines as inhibitors of hepatitis c virus NS3 serine protease
  • Substituted prolines as inhibitors of hepatitis c virus NS3 serine protease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0246] Preparation of intermediates :

[0247] Preparation of Intermediate 1.01 :

[0248] step 1 :

[0249]

[0250] To 4-hydroxyproline derivative 1.02 (1.0g, 4.1mmol) and dichloromethane (50ml) 0 ℃ solution, add 4-nitrophenyl chloroformate (2.46g, 12.2mmol), pyridine ( 0.987ml, 12.2mmol). After 15 minutes at this temperature, the reaction flask was placed in the refrigerator (-20°C) overnight (16 hours). The reaction mixture was diluted with dichloromethane (100ml), washed with saturated ammonium chloride solution (2 x 100ml), brine (100ml), dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (20 / 80 to 50 / 50 EtOAc / hexanes) to afford 1.03 (1.5 g).

[0251] step 2 :

[0252]

[0253] To a stirred solution of proline derivative 1.03 (1.5g, 3.66mmol) and dichloromethane (30ml) at 0°C, 1,2,3,4-tetrahydroisoquinoline (0.55ml, 4.39mmol) and DIPEA (2.02ml, 10.98mmol). After 15 minutes at this tempera...

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PUM

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Abstract

The present invention discloses compounds of formula (I) which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

Description

field of invention [0001] The present invention relates to novel hepatitis C virus ("HCV") protease inhibitors, pharmaceutical compositions containing one or more of said inhibitors, methods of preparing said inhibitors and the use of said inhibitors in the treatment of hepatitis C and related diseases. The invention also discloses a compound containing a new proline part at the P2 position as an inhibitor of HCV NS3 / NS4a serine protease. This application claims priority to US Provisional Patent Application 60 / 573,191, filed May 20,2004. Background of the invention [0002] Hepatitis C virus (HCV) is a (+)-sense single-stranded RNA virus that is the major causative agent of non-A, non-B hepatitis (NANBH), especially blood-associated NANBH (BB-NANBH) (see International Patent Application Publication WO89 / 04669 and European Patent Application Publication EP381216). NANBH differs from other types of virally induced liver diseases such as hepatitis A virus (HAV), hepatitis B ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/10A61K38/55A61K38/00A61K38/04A61K38/05A61K38/21C07D401/12C07D401/14C07D409/14C07D417/02C07K5/02C07K5/04C07K5/06C07K5/083C07K5/087C07K7/02
CPCC07D401/14C07D401/12C07K5/0202C07K7/02A61K38/21C07K5/0205A61K38/212C07D409/14A61P1/16A61P31/14A61K2300/00
Inventor A·阿拉萨潘F·G·恩约洛吉V·M·吉里亚瓦拉布汉
Owner SCHERING AG