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Bicyclic carbohydrate compounds useful in the treatment of infections caused by herpesviridae

a carbohydrate compound and herpes virus technology, applied in the field of compounds active against viral diseases, can solve the problems of unable to clear the virus, cannot eliminate the virus from the body, and doubt the significance of transmission

Inactive Publication Date: 2005-04-28
KEMIN PHARMA EUROPE B.V.B.A.
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is often present in milk in small quantities, but this is of doubtful significance in transmission.
Although specific antibodies and CMI responses are generated, these fail to clear the virus, which often continues to be shed in saliva and urine for many months.
It can prevent CMV from reproducing and infecting new cells, but it cannot eliminate it from the body.
Unfortunately, ganciclovir also suppresses bone-marrow production of the white blood cells called neutrophils.
It can also harm the kidneys, reduce testosterone levels, and cause nausea, vomiting, diarrhea and rash.

Method used

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  • Bicyclic carbohydrate compounds useful in the treatment of infections caused by herpesviridae
  • Bicyclic carbohydrate compounds useful in the treatment of infections caused by herpesviridae
  • Bicyclic carbohydrate compounds useful in the treatment of infections caused by herpesviridae

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of the Compounds of Formula A

[0026] The compounds were synthesized as follows:

1. Synthesis of Compound A1

[0027] The scheme of the synthesis of Compound A1 is illustrated in FIG. 3.

Synthesis of Compound 1.1

[0028] To (β)-D-glucose penta-acetate (24.6 g, 63.0 mmol) was added a solution of hydrogen bromide in acetic acid (33 wt %, 100 ml). A dark brown color immediately appears. The reaction mixture was stirred at room temperature for 30 minutes under argon atmosphere. Subsequently the solvent was removed by azeotropic distillation in vacuo with toluene (4×50 ml), yielding a green-brown solid Compound 1.1. The crude product was used in the next reaction step without further purification.

[0029] Formula: C14H19O9Br

[0030] Molecular weight: 411.20

[0031] Rf: 0.46 (cyclohexane / ethyl acetate 1:1)

[0032] IR (KBr): 2962, 2360, 2342, 1748, 1435, 1369, 1218, 1162, 1112, 1079, 1042, 911, 752, 668, 601, 563 cm−1

[0033] ES-MS: 433=[410+Na]+, 435=[412+Na+]

[0034]1H-NMR (500 MHz, CDC...

example 2

Bioactivity of the Compounds of Formula A

[0253] The compounds were screened against various pathogenic viruses and more specific the human cytomegalovirus (CMV). For determination of the antiviral activity, expressed in IC50, against 2 CMV-strains (Davis and AD-169), human embryonic lung fibroblast (HEL) cells grown in 96-well microplates were infected with 20 PFU virus / well. After 2 hours of incubation at 37° C., the infected cells were replenished with 0.1 ml of medium containing serial dilutions of the test compound. On day 7 the plaques were counted microscopically after staining the cells with Giemsa's solution. The minimum antiviral concentration was expressed as the dose required to inhibit virus-induced plaque formation by 50%.

[0254] The results of the screening of the new compounds against the human cytomegalovirus (CMV) are presented in Table 3.

TABLE 3Antiviral activity of the compoundsIC50(μg / ml)aCMVAD-169DavidCompoundStrainStrainCompound A12.72.0Compound A25.020.0Com...

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Abstract

Bicyclic carbohydrates for the treatment of infections caused by herpseviridae, and in particular cytomegalovirus. The invention consists of the novel bicyclic carbohydrates the generic structure of which is: wherein R1 is either -Bn or -Ph; R2 and R3 are either -alkyl, -aryl, -allyl, or —H; R4 and R5 form a ring and are either —CH(Ph)- or —CH(aryl)- and X is either O, N or S.

Description

BACKGROUND OF THE INVENTION [0001] The invention relates generally to compounds active against viral diseases and, more specifically to bicyclic carbohydrate compounds that are useful in the prophylaxis and treatment of diseases caused by the alphaherpesvirina cytomegalovirus. [0002] Cytomegalovirus (CMV) is the largest human herpes virus, and there is only one serotype. As with animal CMVs it is species specific; humans are the natural hosts and animal CMVs do not infect humans. The name refers to the multinucleated cells, which together with the intranuclear inclusions, are characteristic responses to infection with this virus. Transmission is via saliva, and CMVs were originally called ‘salivary gland’ viruses. Urine is an additional source of infection in children, and in infected pregnant women the virus can spread via the blood to the placenta and fetus. Semen and cervical secretions may also contain virus and it can therefore be spread by sexual contact. It is often present i...

Claims

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Application Information

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IPC IPC(8): A61K31/351A61K31/357A61K31/395A61K31/7034A61K31/7048A61K31/7052C07H15/203A61P31/04A61P31/10A61P31/12A61P33/02A61P35/00A61P43/00C07D309/10C07D493/04C07D493/14C07D498/04C07H9/00C07H9/04C07H13/12C07H15/04
CPCC07D309/10C07D493/04C07H7/02C07H15/203C07H9/04C07H15/04C07H15/10C07H7/04A61P31/04A61P31/10A61P31/12A61P33/02A61P35/00A61P43/00
Inventor SAS, BENEDIKTHEMEL, JOHAN VANVANDENKERCKHOVE, JANPEYS, ERICEYCKEN, JOHAN VAN DERRUTTENS, BARTBLOM, PETRA
Owner KEMIN PHARMA EUROPE B.V.B.A.
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