Glycopeptide antibiotic derivatives

A technology of glycopeptide antibiotics and derivatives, applied in the direction of glycopeptide components, peptides, etc.

Inactive Publication Date: 2006-03-01
K U LEUVEN RES & DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the structures of these hexapeptide or heptapeptide antibiotics differ greatly from the glycopeptide antibiotics and the aglycon structures of the glycopeptide antibiotics in terms of amino acid sequence and stereochemistry

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0246] Example 1: Tables 1-8 represent the structures of compounds prepared as examples and their respective codes

[0247] In this application, some compounds of the present invention are represented by the codes listed below.

[0248] Table 1. Vancomycin-like glycopeptides and their derivatives

[0249]

[0250]

[0251] Table 2. Teicoplanin-like glycopeptides and their derivatives

[0252]

[0253] the code

[0254] Table 3. N-deacylated-A40926 (DA40), demannosyl-N-deacylated A40926 (DMDA40) and their derivatives

[0255]

[0256] the code

[0257] Table 4. Vancomycin aglycones and their derivatives

[0258]

[0259] the code

[0260] Table 5. Teicoplanin aglycones and their derivatives

[0261]

[0262]

[0263] Table 6. Teicoplanin aglycone derivatives with amino acids 1 and 3 removed

[0264]

[0265] the code

[0266] Table 7. Teicoplanin Aglycon Derivatives Breaking the Bond Between Am...

Embodiment 2

[0273] Example 2: General Methods and Materials for Preparation of the Compounds

[0274] Glycopeptide antibiotics and their derivatives, especially the compounds of structural formula Z or I, II, III of the present invention can be prepared by a series of chemical reactions well known to those skilled in the art, which together constitute the preparation of said compounds and more Example method. The methods further described are merely illustrative and not intended to limit the scope of the invention.

[0275] The compounds of the present invention are conveniently prepared by one of the methods described below. The compounds shown in Tables 1-8 were prepared by the following preparation methods.

[0276] All reagents and solvents were purchased from Aldrich (Milwaukee), Fluka (Deisenhofen, Germany), Sigma (St. Louis, MO) and Merck (Darmstadt, Germany). This novel compound was obtained using methods described in the past for the synthesis of other glycopeptide derivativ...

Embodiment 3

[0304] Embodiment 3: measure antiviral (HIV, BVDV, HCV, HSV, VZV, CMV, FCV, SARS) and cell growth Methods of Inhibiting Activity

[0305] Anti-HIV activity assay

[0306] Inhibition of HIV-1 (IIIB, HE, HN) and HIV-2 (ROD, EHO, RF) cytopathic inhibition in CEM or C8166 or Molt4 / C8 cells was determined in 96-well plates in which Contains 3×10 5 CEM cells / ml, each ml was 100CCID 50 HIV-infected and containing appropriate dilutions of the compound to be tested. In control CO 2 The formation of CEM, C8166 or MOLT4 / C8 giant cells (syncytia) was detected microscopically after incubation at 37° C. for 4-5 days in a humidified atmosphere. EC 50 (50% effective concentration) is defined as the concentration of compound required to inhibit HIV-induced giant cell formation by 50%.

[0307] Cytostatic activity assay

[0308] All assays were performed in 96-well microtiter plates. Add 5-7.5 x 10 to each well 4 cells and add a certain amount of test compound. In humid controlled...

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Abstract

Novel glycopeptide antibiotic derivatives, processes for their preparation, their use as a medicine, their use to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections are provided. The present invention relates to the use of glycopeptide antibiotics and their semisynthetic derivatives to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections of subjects, more in particular infections with viruses belonging to Retroviridae, Herpes viridae, Flaviviridae and the Coronaviridae, like HIV (human immunodeficiency virus), HCV (hepatitis C virus), BVDV (bovine viral diarrhoea virus), SARS (severe acute respiratory syndrome) causing virus, FCV (feline coronavirus), HSV (herpes simplex virus), VZV (varicella zoster virus) and CMV (cytomegalovirus).

Description

field of invention [0001] The field of the invention relates to novel glycopeptide antibiotic derivatives, their preparation, their use as medicaments, their use in the treatment or prevention of viral infections and their use in the manufacture of medicaments for the treatment or prevention of viral infections . The present invention relates to the use of glycopeptide antibiotics and their semi-synthetic derivatives for the treatment or prevention of viral infections and their use in the manufacture for the treatment or prevention of viral infections in a subject, especially by retroviridae, herpesviruses family, Flaviviridae, and Coronaviridae (such as HIV (Human Immunodeficiency Virus), HCV (Hepatitis C Virus), BVDV (Bovine Viral Diarrhea Virus), the virus that causes SARS (Severe Acute Respiratory Syndrome), FCV ( Feline coronavirus), HSV (herpes simplex virus), VZV (varicella-zoster virus) and CMV (cytomegalovirus)). Background of the invention [0002] Viral infectio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K38/14C07K9/00
Inventor J・巴尔扎里尼M・普雷奥布拉兹汉斯卡亚E・德克勒克
Owner K U LEUVEN RES & DEV
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