Antipicornaviral compounds and methods for their use and preparation

A compound of the formula (I):

• ##STR204## wherein:
• R.sub.1 is H, F, an alkyl group, OH, SH, an O-alkyl group, or an S-alkyl group;
• one of R.sub.2 and R.sub.5 is H or an alkyl group and the other is ##STR205## wherein R.sub.35 is H, an alkyl group, or an aryl group, and R.sub.36 is H or an alkyl group;
• R.sub.3 and R.sub.6 are independently H, F, or an alkyl group;
• R.sub.4 is H, OH, or a suitable organic moiety;
• Z and Z.sub.1 are independently H, F, an alkyl group, a cycloalkyl group, an aryl group, --C(O)R.sub.21, --CO.sub.2 R.sub.21, --C(O)NR.sub.21 R.sub.22, --C(O)NR.sub.21 OR.sub.22, --C(S)R.sub.21, --C(S)NR.sub.21 R.sub.22, --NO.sub.2, --SOR.sub.21, --SO.sub.2 R.sub.21, --SO.sub.2 NR.sub.21 R.sub.22, --SO(NR.sub.21)(OR.sub.22), --SONR.sub.21, --SO.sub.3 R.sub.21, --PO(OR.sub.21).sub.2, --PO(R.sub.21)R.sub.22), --PO(NR.sub.21 R.sub.22)(OR.sub.23), --PO(NR.sub.21 R.sub.22)(NR.sub.23 R.sub.24), --C(O)NR.sub.21 NR.sub.22 R.sub.23, or --C(S)NR.sub.21 NR.sub.22 R.sub.23,
• wherein R.sub.21, R.sub.22, R.sub.23, and R.sub.24 are independently H, an alkyl group, a cycloalkyl group, an aryl group, an acyl group, or a thioacyl group, with the proviso that at least one of Z or Z.sub.1 is a --CO.sub.2 R.sub.50 group, where R.sub.50 represents an alkyl group, a cycloalkyl group, or an aryl group;
• or Z and Z.sub.1 both as defined above, together with the atoms to which they are bonded, form a cyclic carboxylic acid ester group;
• or a pharmaceutically acceptable prodrug, salt, or solvate thereof;
• and wherein the compound, pharmaceutically acceptable prodrug, salt, or solvate thereof, has antipicornaviral activity with an EC.sub.50 less than or equal to 100 .mu.M in the HI-HeLa cell culture assay.