Novel Antiviral Helioxanthin Analogs

An isolated compound of the formula:

• Where R1 and R2 are independently C1-C6 alkyl, COO—Na+
• a —(CH2)naryl, —(CH2)nZ-(C1-C6)alkyl, —(CH2)nZ-(CH2)naryl, each of which groups may be optionally substituted with one or more halogens, OH, COOH, C1-C3 alkyl or CN,
• or R1 and R2 are independently a —(CH2)nNR3R4 group,
• or R1 and R2 together with the adjacent benzene ring form a 5- or 6-membered
• heterocyclic ring according to the structure Ia:
• where Y is O, a N—R6a group or a —N(R7)—N(R8)— group;
• X1 and X2 are independently a CH2 or C═O group;
• R1 is OH, a —(C1-C6)alkyl, a —(CH2)naryl, a —(CH2)nZ-(C1-C6)alkyl, a —(CH2)nZ-(CH2)naryl
• each of which groups may be optionally substituted with one or more halogens, OH, COOH, C1-C3 alkyl or CN, or
• wherein R1 is a —(CH2)nNR5R6 group,
• R3 and R4 are independently selected from H, —(C1-C6) alkyl or a
• where R2 is H, a —(C1-C6)alkyl, a —(CH2)naryl, —(CH2)jO—(C1-C6)alkyl or a —(CH2)jO—(CH2)naryl;
• R5 and R6 are independently selected from H, —(C1-C4)nalkyl, —(CH2)naryl, —(CH2)jO—(C1-C6)alkyl or —(CH2)jO—(CH2)naryl;
• R6a is H, a C1-C6 alkyl optionally substituted with a hydroxyl group or aryloxy group, —OR9 or N—R10;
• R7, R8, and R9 are independently H or a C1-C6 alkyl group which may be optionally substituted with a hydroxyl group;
• R10 is H, —(C1-C6)alkyl or —C(═O)(C1-C6)alkyl;
• Z is O or NH;
• R13 is H, OH, —O(C1-C4)alkyl, (C1-C4) alkyl;
• R15 is H, OH, —O(C1-C4)alkyl, (C1-C4) alkyl, F, Cl, Br or I;
• Ra and Rb are independently a —(C1-C6)alkyl, or together form a —(CH2)k— group;
• j is 1, 2, 3, 4 or 5,
• k is 1 or 2;
• and
• n is 0, 1, 2, 3, 4 or 5;
• with the proviso that when Y is O, R15 is Cl, Br or I and when R1 and R2 is COOH, R15 is Cl or I,
• or their anomers, pharmaceutically acceptable salts, solvates, or polymorphs thereof.