Pyrroloquinolones as antiviral agents

A compound of formula I

• 51
• or a pharmaceutically acceptable salt, racemate, solvate, tautomer, optical isomer or prodrug derivative thereof wherein:
• R1 is
• (a) F,
• (b) Cl,
• (c) Br,
• (d) CN or
• (e) NO2;
• R2 and R3 are independently
• (a) H,
• (b) halo,
• (c) OR11,
• (d) C(═O)R7,
• (e) C(═O)OR11,
• (f) C3-8cycloalkyl, or
• (g) C1-7alkyl which may be partially unsaturated and optionally substituted by one or more halo, C3-8cycloalkyl, R2, OR14, SR11, SR14, NR8R9, NR11C(O)R7, (C═O)C1-7 alkyl, or SOmR10;
• R4, and R5 are independently
• (a) H,
• (b) halo,
• (c) aryl,
• (d) S(O)mR7,
• (e) (C═O)R7,
• (f) (C═O)OR10,
• (g) CN,
• (h) het, wherein said het is bound via a carbon atom,
• (i) OR11,
• (j) Ohet,
• (k) NR8R9
• (I) SR11,
• (m) Shet,
• (n) NHCOR3,
• (o) NHSO2R13,
• (p) C3-8cycloalkyl, or
• (q) C1-7alkyl which may be partially unsaturated and optionally substituted by one or more R12, OR14, SR11, SR14, NR8R9, halo, C3-8cycloalkyl, (C═O)C1-7alkyl, or SOmR10;
• R6 is
• (a) H,
• (b) halo,
• (c) C3-8cycloalkyl, or
• (d) C1-4alkyl optionally substituted by 1-3 halo;
• R7 is
• (a) C1-7alkyl,
• (b) C3-8cycloalkyl,
• (c) NR8R9,
• (d) aryl, or
• (e) het, wherein said het is bonded via a carbon atom;
• R8 and R9 are independently
• (a) H,
• (b) aryl,
• (c) C3-8cycloalkyl,
• (d) C1-7alkyl which may be partially unsaturated and is optionally substituted by one or more NR11R11, R12, SOmR10, CONR11R11, OH, aryl, het, C3-8cycloalkyl, or halo, or
• (e) R8 and R9 together with the nitrogen to which they are attached for a het;
• R10 is
• (a) aryl,
• (b) het,
• (c) C3-8cycloalkyl, or
• (d) C1-7alkyl which may be partially unsaturated and is optionally substituted by one or more NR11R11, R12, SH, CONR11R11, C3-8cycloalkyl, or halo;
• R11 is
• (a) H,
• (b) aryl,
• (c) C3-8cycloalkyl, or
• (d) C1-7alkyl optionally substituted by OH;
• R12 is
• (a) OR11,
• (b) Ohet,
• (c) Oaryl,
• (d) CO2R11,
• (e) het,
• (f) aryl, or
• (g) CN;
• R13 is
• (a) H,
• (b) het,
• (c) aryl,
• (d) C3-8cycloalkyl, or
• (e) C1-7alkyl optionally substituted by NR11R11 or R12;
• R14 is
• (a) (P═O)(OR15)2,
• (b) CO(CH2)nCON(CH3)—(CH2)nSO3−M+,
• (c) an amino acid,
• (d) C(═O)aryl, or
• (e) C(═O)C1-7alkyl optionally substituted by NR11R11, aryl, het, CO2H, or O(CH2)nCO2R15;
• R15 is
• (a) H, or
• (b) C1-7alkyl;
• aryl is a phenyl radical or an ortho-fused bicyclic carbocyclic radical wherein at least one ring is aromatic;
• at each occurrence, aryl may be additionally substituted with one or more halo, CN, CO2R11, SR11, OR11, NR11R11, C1-4alkyl, CF3, or C3-8cycloalkyl;
• het is a four—(4), five—(5), six—(6), or seven—(7) membered saturated or unsaturated heterocyclic ring having 1, 2, or 3 heteroatoms selected from the group consisting of O, SOm, and NX;
• wherein X is H, C1-4alkyl or absence, wherein het is optionally fused to a benzene ring, or any bicyclic heterocycle group;
• at each occurrence, het may be additionally substituted with one or more halo, CN, CO2R11, SR11, OR11, NR11R11, C(═O)R13, C1-4alkyl, CF3, C3-8cycloalkyl, oxo or oxime;
• at each occurrence, m is independently 0, 1, or 2;
• at each occurrence, n is independently 1, 2, 3, 4, 5 or 6;
• and
• M is sodium, potassium, or lithium.