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N-terminally modified tetrapeptide derivatives having a C-terminal arginine mimetic as antiviral protease inhibitors

03.03.2011
The invention concerns N-terminally modified tetrapeptide mimetics having a C-terminal arginine mimetic according to the general formula

P5-P4-P3-P2-P1 wherein <ul><li>P1 is an amidinophenyl or amidinopiperazinyl group,

<li>P2 and P4 represent a substituted amino- or imino acid, for example, a guanidino or amino lysine or a substituted proline, <li>P3 is a natural or unnatural ?-amino acid in D- or L-configuration and <li>P5 can be chosen from various residues, for example from alkylene, cholyl, sphingosyl or pyroglutamyl.</ul><p> The P5 residue is very variable and can stand for a hydrogen atom in the simplest case. Advantageously, P5 is a hydrophobic acyl residue derived from naturally occurring fatty acids, wherein the acyl residue can be saturated, monounsaturated, or polyunsaturated. Aralkylcarbonyl, heteroaralkylcarbonyl, and sulfonyl residues are also advantageous.<p> The invention at hand provides novel inhibitors for human proprotein convertase, which have antibacterial and antiviral effects. These inhibitors are multibasic, N-terminally modified tetrapeptide derivatives having a C-terminal P1-arginine mimetic. In contrast to previous active substances against bacterial and viral diseases, the substances presented here do not apply to the pathogenic organism, but the host, so that there is no development of resistance to contend with.

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