Bicyclic carbohydrate compounds useful in the treatment of infections caused by flaviviridae sp., such as hepatitis c and bovine viral diarrhea viruses

A technology of bovine viral diarrhea and compounds, applied in the direction of carbohydrate active ingredients, carbocyclyl sugars, sugar derivatives, etc., can solve the problems of lack of immunity and high proportion of re-infection

Inactive Publication Date: 2007-11-07
凯敏制药欧洲股份有限公司
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

HCV genetic diversity results in a virus with the ability to evade host immune surveillance, which results in a high proportion (over 80%) of chronic infection in repeatedly exposed individuals and a lack of immunity to reinfection

Method used

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  • Bicyclic carbohydrate compounds useful in the treatment of infections caused by flaviviridae sp., such as hepatitis c and bovine viral diarrhea viruses
  • Bicyclic carbohydrate compounds useful in the treatment of infections caused by flaviviridae sp., such as hepatitis c and bovine viral diarrhea viruses
  • Bicyclic carbohydrate compounds useful in the treatment of infections caused by flaviviridae sp., such as hepatitis c and bovine viral diarrhea viruses

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Embodiment

[0020] Methods and Materials

[0021] Synthesis of Formula A Compound

[0022] This compound is synthesized as follows:

[0023] 1. Synthesis of compound A1 and compound A2

[0024] The synthesis of Compound A1 and Compound A2 is shown in Figure 2.

[0025] Synthesis of Compound 1.1

[0026] To 2,3,4,6-tetra-O-benzyl-D-glucose (10.0 g, 18.5 mmol) in CH at RT (room temperature) 2 Cl 2 (125ml) and DMF (6.25ml) were added dropwise to a solution of oxalyl bromide (2.5ml in CH 2 Cl 2 10M solution in , 1.35eq). Simultaneously with strong gas generation. The reaction mixture was stirred at room temperature under Ar atmosphere for 60 minutes. The reaction mixture was then poured into ice water (125ml). After phase separation, the organic phase was washed with ice water (2 x 125 ml). with MgSO 4 After drying, filtration and evaporation in vacuo, compound 1.1 was obtained as a yellow oil (Figure 1), which was used in the following reaction step without further purification. ...

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Abstract

The invention discloses an application of bicyclic saccharide in the treatment of hepatitis C virus infection. Aiming at DNA viruses, retroviruses and important family Flaviviridae viruses of human and animal RNA pathogenes, different bicyclic saccharide compounds are tested in the body to observe that the bicyclic saccharide compounds have remarkable activities to boyine viral diarrhoea viruses (BVDV). Plague viruses such as BVDV, etc., are greatly similar to the hepatitis C virus (HCV), so the usual bicyclic saccharide and the bicyclic saccharide which is preferred more concretely are expected to be used to treat the hepatitis C virus infection.

Description

technical field [0001] The present invention generally relates to bicyclic saccharide compounds useful in the treatment of infections caused by viruses of the Flaviviridae family. More particularly, it relates to such compounds useful in the treatment or amelioration of infections caused by hepatitis C virus, bovine viral diarrhea virus, swine fever virus, West Nile virus and dengue virus. Background technique [0002] Hepatitis C was first recognized as a separate disease entity in 1975, when it was discovered that most cases of hepatitis associated with blood transfusions were not caused by only two hepatitis viruses known at the time—hepatitis A virus and hepatitis B virus— — caused by. The disease is called "non-A non-hepatitis" and has been found to be transmissible to chimpanzees. However, it was not until 1989 that the cloning and sequencing of this non-A, non-B hepatitis virus was first reported, and the virus was renamed "hepatitis C virus" (HCV). This was follow...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/00C07D498/02A61K31/357A61K31/385A61K31/519A61K31/70
CPCA61K31/357C07H15/04A61K31/385C07H7/04C07D493/04A61K31/70A61K31/519C07H9/04A61P31/14
Inventor 贝内迪克特·萨斯约翰·范赫梅尔扬·范登凯尔克霍弗埃里克·派斯约翰·范德艾肯巴尔特·鲁滕斯扬·巴尔扎里尼埃里克·德克莱尔约翰·奈伊茨
Owner 凯敏制药欧洲股份有限公司
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