Antibacterial cyclopenta[c]pyrrole substituted 3,4-dihydro-1h-[1,8]naphthyridinones

A process for preparing a compound of formula (I),

• comprising
• reacting an intermediate of formula (II) with an intermediate of formula (III),
• wherein
• A represents —C≡C— or
• the bond represents a single bond or a double bond;
• X represents carbon or nitrogen, and when X represents nitrogen then the bond represents a single bond;
• Z1 represents CH or N;
• R1 is hydrogen, C1-4alkyl or halo;
• R2 is hydrogen, C1-4alkyl or halo;
• R3 is hydrogen, C1-6alkyl, hydroxy or halo;
• R4 is hydrogen, halo, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C1-6alkyloxy, C1-4alkyloxycarbonyl, aminocarbonyl, mono- or di(C1-4alkyl)-aminocarbonyl, aryl, aryloxy, arylcarbonyl, arylsulfonyl, heteroaryl, C1-6alkyl substituted with cyano, C1-6alkyl substituted with aryl or aryloxy, or C1-6alkyl substituted with heteroaryl;
• wherein said heteroaryl is furanyl, thiophenyl, pyrrolyl, pyrazolyl, imidazolyl, isoxazolyl, thiazolyl, triazolyl, tetrazolyl, isothiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, benzo[1,3]dioxolyl, benzofuranyl, benzothiazolyl, indolyl, 2,3-dihydro-1H-indolyl, tetrahydrothiophenyl, or quinolinyl, and wherein each heteroaryl may be substituted with one or two substituents each independently selected from halo, cyano, C1-4alkyl, C1-4alkyloxy, C1-4alkylcarbonyl, and phenyl;
• wherein said aryl is phenyl, or phenyl substituted with one, two or three substituents each individually selected from halo, hydroxy, C1-4alkyl, C1-4alkyloxy, polyhaloC1-4alkyl, polyhaloC1-4alkyloxy, cyano, nitro, and amino;
• and
• Y is hydroxy or halo.

A process for preparing a compound of formula (I),

• comprising
• reacting an intermediate of formula (V) with an intermediate of formula (VI),
• wherein
• A is
• the bond represents a single bond or a double bond;
• X represents carbon or nitrogen, and when X represents nitrogen then the bond represents a single bond;
• Z1 represents CH or N;
• R1 is hydrogen, C1-4alkyl or halo;
• R2 is hydrogen, C1-4alkyl or halo;
• R3 is hydrogen, C1-6alkyl, hydroxy or halo;
• R4 is hydrogen, halo, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C1-6alkyloxy, C1-4alkyloxycarbonyl, aminocarbonyl, mono- or di(C1-4alkyl)-aminocarbonyl, aryl, aryloxy, arylcarbonyl, arylsulfonyl, heteroaryl, C1-6alkyl substituted with cyano, C1-6alkyl substituted with aryl or aryloxy, or C1-6alkyl substituted with heteroaryl;
• wherein said heteroaryl is furanyl, thiophenyl, pyrrolyl, pyrazolyl, imidazolyl, isoxazolyl, thiazolyl, triazolyl, tetrazolyl, isothiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, benzo[1,3]dioxolyl, benzofuranyl, benzothiazolyl, indolyl, 2,3-dihydro-1H-indolyl, tetrahydrothiophenyl, or quinolinyl, and wherein each heteroaryl may be substituted with one or two substituents each independently selected from halo, cyano, C1-4alkylcarbonyl, and phenyl;
• wherein said aryl is phenyl, or phenyl substituted with one, two or three substituents each individually selected from halo, hydroxy, C1-4alkyl, C1-4alkyloxy, polyhaloC1-4alkyl, polyhaloC1-4alkyloxy, cyano, nitro, and amino;
• Y is hydroxy or halo;
• and
• Xa1 represents a suitable leaving group.