Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis

An antipicornaviral compound having the formula:

• wherein:
• Ra is an alkylcarbonylalkyl, cycloalkylcarbonylalkyl, arylcarbonylalkyl, heteroarylcarbonylalkyl, alkylcarbonylaminoalkyl, cycloalkylcarbonylaminoalkyl, heteroarylcarbonylaminoalkyl, alkylaminocarbonylalkyl, cycloalkylaminocarbonylalkyl, heterocycloalkylaminocarbonylalkyl, arylaminocarbonylalkyl, heteroarylaminocarbonylalkyl group, where each alkyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl moiety thereof may be unsubstituted or substituted with one or more suitable substituents
• Rb is H or an alkyl group, unsubstituted or substituted with one or more suitable substituents;
• Rd is H, Halo, hydroxyl, or an alkyl, alkoxy or alkylthio group, where the alkyl, alkoxy or alkylthio group is unsubstituted or substituted with one or more suitable substituents;
• Rc is a moiety having the formula:
• Rc and Rf are each independently H or a lower alkyl group;
• m is 1, provided that when m is 1, Ra is not an amino-substituted alkylcarbonylalkyl or amino-substituted alkylcarbonylaminoalkyl group;
• p is 1;
• A1 is CH;
• when p is 1, A2 is C(Rg)(Rh), where each Rg and Rh is independently H or a lower alkyl group;
• each A3 present is independently C(Rg)(Rh), where each Rg, and Rh is independently H or a lower alkyl group;
• when p is 1, A4 is N(Rj), and each Rj is H, an alkyl, aryl, or acyl group;
• where each dotted line in the ring depicts a single and
• Z and Z1 are each independently H, F, an alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl group, where the alkyl, cycloalkyl, heterocycloalkyl, or aryl group is unsubstituted or substituted with one or more suitable substituents wherein the heterocycloalkyl is a five membered heterocycloalkyl,
• or Z and Z1, together with the atoms to which they are bonded, form a cycloalkyl or heterocycloalkyl group, where Z and Z1 are as defined above and the heterocycloalkyl is a five membered heterocycloalkyl;
• or a pharmaceutically acceptable salt, pharmaceutically active metabolite, or pharmaceutically acceptable solvate of said compound.