6,7,8,9-substituted 1-phenyl-1,5-dihydro-pyrido[3,2-b]indol-2-ones useful as anti-infective pharmaceutical agents

A compound of formula (I):

• or pharmaceutically acceptable salts thereof,
• wherein
• n is 1;
• R1 is cyano;
• X is a bivalent radical NR2;
• R2 is hydrogen or C1-6 alkyl;
• -a1=a2-a3=a4- represents a bivalent radical of formula
• —CH═CH—CH═CH— (c-1),
• wherein one, two, three or four of the hydrogen atoms in (c-1) is replaced by a radical C1-6alkyl, C1-4alkoxy, halo, hydroxy, (R5g)(R5h)N—(C1-4alkanediyl)-O—, (R7)(R8)N—(C1-4alkanediyl)-O—, (R8)(R9)N—(C1-4alkanediyl)-O—, trifluoromethyl, cyano, a radical —COOR4, (R5a)(R5b)N-carbonyl, (R5a)(R5b)N-sulfonyl, pyrrolidinylsulfonyl, piperidinylsulfonyl, homopiperidinylsulfonyl, formyl, C1-6alkylcarbonyl, nitro, hydroxyC1-6alkyl, C1-4alkoxyC1-6alkyl, (R4OOC)—C1-6alkyl, a radical —N(R5a)(R5b), —N(R7)(R8), —N(R9)(R10), a radical
• morpholinyl, thiomorpholinyl, 1-oxothiomorpholinyl, 1,1-dioxo-thiomorpholinyl, (R5g)(R5h)N—(C1-4alkanediyl)-N(R5c)—, (R7)(R8)N—(C1-4alkanediyl)-N(R5c)—, (R9)(R10)N—(C1-4alkanediyl)-N(R5c)—, C1-6alkylcarbonylamino, C1-6alkyloxycarbonylamino, trifluoroacetylamino, C1-6alkylsulfonylamino, (R5a)(R5b)N—C1-4alkyl;
• aryl;
• Het1 or Het2;
• R20 is hydrogen, hydroxy, C1-4alkyl, arylC1-4alkyl, C1-4alkyloxy, arylC1-4alkyloxy, oxo, spiro(C2-4alkylenedioxy), spiro(diC1-4alkyloxy), —NR5gR5h;
• each R5g or R5h independently is hydrogen, C1-4alkyl or arylC1-4alkyl, or R5g and R5h together with the nitrogen to which they attached form a pyrrolidinyl, piperidinyl, homopiperidinyl, morfolinyl, piperazinyl or 4-C1-4alkylpiperazinyl radical;
• wherein each of said pyrrolidinyl, piperidinyl, homopiperidinyl, morfolinyl, piperazinyl or 4-C1-4alkylpiperazinyl radical may optionally be substituted with hydroxy or oxo;
• R3 is amino, nitro or cyano;
• aryl is phenyl optionally substituted with one or more substituents each individually selected from the group consisting of C1-6alkyl, C1-4alkoxy, halo, hydroxy, amino, trifluoromethyl, cyano, nitro, hydroxyC1-6alkyl, cyanoC1-6alkyl, mono- or di(C1-4alkyl)amino, aminoC1-4alkyl, mono- or di(C1-4alkyl)aminoC1-4alkyl;
• Het1 is a 5-membered ring system wherein one, two, three or four ring members are heteroatoms each individually and independently selected from the group consisting of nitrogen, oxygen and sulfur, and wherein the remaining ring members are carbon atoms;
• and, where possible, any nitrogen ring member may optionally be substituted with C1-4alkyl;
• any ring carbon atom may, each individually and independently, optionally be substituted with a substituent selected from the group consisting of C1-4alkyl, C2-6alkenyl, C3-7cycloalkyl, hydroxy, C1-4alkoxy, halo, amino, cyano, trifluoromethyl, hydroxyC1-4alkyl, cyanoC1-4alkyl, mono- or di(C1-4alkyl)amino, aminoC1-4alkyl, mono- or di(C1-4alkyl)aminoC1-4alkyl, arylC1-4alkyl, aminoC2-6alkenyl, mono- or di(C1-4alkyl)aminoC2-6alkenyl, furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, aryl, hydroxycarbonyl, aminocarbonyl, C1-4alkyloxycarbonyl, mono- or di(C1-4alkyl)aminocarbonyl, C1-4alkylcarbonyl, oxo, thio;
• and wherein any of the foregoing furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl and triazolyl moieties may optionally be substituted with C1-4alkyl;
• and
• Het2 is pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl, wherein any ring carbon atom of each of said 6-membered nitrogen containing aromatic rings may optionally be substituted with a substituent selected from the group consisting of C1-4alkyl.