1,5,6,-Substituted-2-Oxo-3-Cyano-1,6a-Diaza-Tetrahydro-Fluoranthenes as Anti-Infective Agents

A compound of formula:

• the salts and stereoisomeric forms thereof,
• wherein
• R1 and R2 are each, independently, hydrogen or C1-10alkyl, which may be optionally substituted with a substituent selected from hydroxy, cyano, NR4R5, pyrrolidinyl, piperidinyl, homopiperidinyl, piperazinyl, 4-(C1-4alkyl)-piperazinyl, morpholinyl, thiomorpholinyl, 1-oxothiomorpholinyl, 1,1-dioxo-thiomorpholinyl, aryl, furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, hydroxycarbonyl, C1-4alkylcarbonyl, (R4)(R5)N-carbonyl, C1-4alkyloxycarbonyl, pyrrolidin-1-ylcarbonyl, piperidin-1-ylcarbonyl, homopiperidin-1-ylcarbonyl, piperazin-1-ylcarbonyl, 4-(C1-4alkyl)-piperazin-1-ylcarbonyl, morpholin-1-yl-carbonyl, thiomorpholin-1-ylcarbonyl, 1-oxothiomorpholin-1-ylcarbonyl and 1,1-dioxo-thiomorpholin-1-ylcarbonyl;
• R3 is a radical of formula
• wherein n is 1, 2 or 3;
• R3a is nitro, cyano, amino, halo, hydroxy, C1-4alkyloxy, hydroxycarbonyl, aminocarbonyl, C1-4alkyloxycarbonyl, mono- or di(C1-4alkyl)aminocarbonyl, C1-4alkylcarbonyl, methanimidamidyl, mono- or di(C1-4alkyl)methanimidamidyl, N-hydroxymethanimidamidyl or Het;
• or
• R3 is a monocyclic or bicyclic aromatic heterocyclic ring system, wherein one, two, three or four ring members are heteroatoms each independently selected from nitrogen, oxygen and sulfur, and wherein the remaining ring members are carbon atoms;
• and wherein each of said heterocyclic ring systems may optionally be substituted with one, two, three, four or five substituents each independently selected from halo, cyano, nitro, C1-6alkyl, hydroxyC1-6alkyl, C1-4alkoxyC1-6alkyl, (R5a)(R5b)N-C1-4alkyl, polyhaloC1-6alkyl, C3-7cycloalkyl, arylC1-6alkyl, formyl, C1-6alkylcarbonyl, a radical —COOR6,(R5a)(R5b)N-carbonyl, (R5a)(R5b)N-sulfonyl, hydroxy, C1-6alkyloxy, arylC1-6alkyloxy, polyhalo-C1-6alkyloxy, formyloxy, C1-6alkylcarbonyloxy, aryloxy, a radical (R5a)(R5b)N—, formylamino, C1-6alkylcarbonylamino, C1-6alkyloxycarbonylamino, C1-6alkylsulfonylamino, mercapto, C1-6alkylthio, arylthio, arylC1-6alkylthio, C1-6alkylsulfinyl, C1-6alkylsulfonyl, aryl, —CH(═N—O— R5a), and —C(═NH)—NH—R5a;
• X is —NR7—, —O— or —S—;
• R4 and R5 each independently are hydrogen, C1-6alkyl or C1-6alkyl substituted with a substituent selected from amino, mono- or di-(C1-4alkyl)amino, pyrrolidinyl, piperidinyl, homopiperidinyl, piperazinyl, 4-(C1-4alkyl)-piperazinyl, morpholinyl, thiomorpholinyl, 1-oxothiomorpholinyl and 1,1-dioxo-thiomorpholinyl;
• each R5a, R5b independently is hydrogen, C1-4alkyl or arylC1-4alkyl;
• R6 is hydrogen, C1-4alkyl or arylC1-4alkyl;
• R7 is hydrogen, C1-6alkyl, optionally substituted with aryl, (R4)(R5)N—, pyrrolidinyl, piperidinyl, homopiperidinyl, piperazinyl, 4-(C1-4alkyl)-piperazinyl, morpholinyl, thiomorpholinyl, 1-oxothiomorpholinyl or with 1,1-dioxo-thiomorpholinyl;
• each aryl independently is phenyl optionally substituted with 1, 2 or 3 substituents each independently selected from 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;
• Het is a 5- or 6-membered ring system wherein one, two, three or four ring members are heteroatoms each individually and independently selected from 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 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, aminoC3-6alkenyl, mono- or di(C1-4alkyl)aminoC3-6alkenyl, 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, and 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.