Pyrimidine derivatives

A pharmaceutical composition comprising a pharmaceutically or diagnostically acceptable excipient and a compound having the formula:

• 139
• wherein
• X is a member selected from the group consisting of —NR3R4, —OR3, —SR3, aryl, alkyl and arylalkyl;
• Y is a member selected from the group consisting of a covalent bond, —N(R6)—, —O—, —S—, —C(═O)— and alkylene;
• R1 and R2 are members independently selected from the group consisting of hydrogen, alkyl, —O-alkyl, —S-alkyl, aryl, arylalkyl, —O-aryl, —S-aryl, —NO2, —NR7R8, —C(O)R9, —CO2R10, —C(O)NR7R8 —N(R7)C(O)R9, —N(R7)CO2R11, —N(R9)C(O)NR7R8, —S(O)mNR7R8, —S(O)nR9, —CN, halogen, and —N(R7)S(O)mR11;
• R3 and R4 are members independently selected from the group consisting of hydrogen, alkyl, aryl and arylalkyl, or taken together with the nitrogen atom to which each is attached form a 5-, 6- or 7-membered ring containing from one to three heteroatoms in the ring;
• R5 is a member selected from the group consisting alkyl, aryl, arylalkyl and bicyclic fused aryl-cycloalkyl;
• R6 is a member selected from the group consisting of hydrogen, alkyl, aryl and arylalkyl;
• or is combined with R5 and the nitrogen atom to which R5 and R6 are attached to form a 5-, 6-, 7- or 8-membered ring;
• R7 and R8 are members independently selected from the group consisting of hydrogen, alkyl, aryl and arylalkyl, or, taken together with the nitrogen atom to which each is attached, form a 4-, 5-, 6-, 7- or 8-membered ring containing from one to three heteroatoms in the ring;
• R9 and R10 are members independently selected from the group consisting of hydrogen, alkyl, aryl and arylalkyl;
• R11 is a member selected from the group consisting of alkyl, aryl and arylalkyl;
• m is an integer of from 1 to 2;
• n is an integer of from 1 to 3;
• and
• optionally, a 5-, 6-, 7- or 8-member ring is formed by joining R1 to R2, R1 to R3, R3 to N3, R5 to N3, R5 to N1, or R2 to N1;
• said compound having a molecular weight of from about 150 to about 750, with the proviso that when Y is a bond, then R5 is other than an imidazole ring.

A method for preventing or suppressing a viral infection in a mammal, comprising administering to said mammal a viral infection suppressing amount of a compound having the formula:

• 154
• wherein
• X is a member selected from the group consisting of —NR3R4, —OR3, —SR3, aryl, alkyl and arylalkyl;
• Y is a member selected from the group consisting of a covalent bond, —N(6)—, —O—, —S—, —C(═O)— and alkylene;
• R1 and R2 are members independently selected from the group consisting of hydrogen, alkyl, —O-alkyl, —S-alkyl, aryl, arylalkyl, —O-aryl, —S-aryl, —NO2, —NR7R8, —C(O)R9, —CO2R10, —C(O)NR7R8 —N(R7)C(O)R9, —N(R7)CO2R11, —N(R9)C(O)NR7R8, S(O)mNR7R8, —S(O)nR9, —CN, halogen, and —N(R7)S(O)mR11;
• R3 and R4 are members independently selected from the group consisting of hydrogen, alkyl, aryl and arylalkyl, or taken together with the nitrogen atom to which each is attached form a 5-, 6- or 7-membered ring containing from one to three heteroatoms in the ring;
• R5 is a member selected from the group consisting alkyl, aryl, arylalkyl and bicyclic fused aryl-cycloalkyl;
• R6 is a member selected from the group consisting of hydrogen, alkyl, aryl and arylalkyl;
• or is combined with R5 and the nitrogen atom to which R5 and R6 are attached to form a 5-, 6-, 7- or 8-membered ring;
• R7 and R8 are members independently selected from the group consisting of hydrogen, alkyl, aryl and arylalkyl, or, taken together with the nitrogen atom to which each is attached, form a 4-, 5-, 6-, 7- or 8-membered ring containing from one to three heteroatoms in the ring;
• R9 and R10 are members independently selected from the group consisting of hydrogen, alkyl, aryl and arylalkyl;
• R11 is a member selected from the group consisting of alkyl, aryl and arylalkyl;
• m is an integer of from 1 to 2;
• n is an integer of from 1 to 3;
• and
• optionally, a 5-, 6-, 7- or 8-member ring is formed by joining R1 to R2, R1 to R3 R3 to N3, R5 to N3, R5 to N1, or R2to N1;
• said compound having a molecular weight of from about 150 to about 750.