Substituted tricyclic derivatives

1. A compound of formula (I):

wherein:

Z represents a bond, a carbonyl group, or a methylene group optionally substituted by one or two groups chosen from a C 1-6 alkyl group, a hydroxyl group, and a C 1-6 alkoxy group;

R1 represents a 4-pyridine ring or a 4-pyrimidine ring;

R2 represents a hydrogen atom;

R3 represents:

a hydrogen atom;

a phenyl or a naphthyl group, these groups being optionally substituted by 1 to 4 substituents selected from a C 1-6 alkyl group, a halogen atom, a C 1-2 perhalogenated alkyl group, a C 1-3 halogenated alkyl group, a hydroxyl group, a C 1-6 alkoxy group, a C 1-2 perhalogenated alkoxy group, a C 1-6 alkylsulfonyl group, a nitro, a cyano, an amino, a C 1-6 monoalkylamino group, a C 2-12 dialkylamino group, an acetoxy group, an aminosulfonyl group, and a heterocyclic group, this heterocyclic group being optionally substituted by a C 1-6 alkyl group, a halogen atom, a C 1-2 perhalogenated alkyl group, a C 1-3 halogenated alkyl group, a hydroxyl group, or a C 1-6 alkoxy group; or

a 5, 6 or 5-6 membered heteroaromatic group, this group being optionally substituted by 1 to 4 substituents selected from a C 1-6 alkyl group, a halogen atom, a C 1-2 perhalogenated alkyl group, a C 1-6 halogenated alkyl group, a hydroxyl group, a C 1-6 alkoxy group, a C 1-6 halogenated alkoxy group, a nitro, a cyano, an amino, a C 1-6 monoalkylamino group, a C 2-12 dialkylamino group, a S—(C 1-6 -alkyl) group, a C(O)O(C 1-6 -alkyl), and a C(O)O(phenyl) group;

n represents 0 to 3; and

m represents 0 to 1;

with the proviso that the compound of formula (I) wherein n and m represent 0, Z represents a bond, R2 and R3 represent a hydrogen atom and R1 represents a 4-pyridine ring is not included;

or an acid addition salt thereof.

2. A compound of formula (I):

wherein:

Z represents a bond, a C 1-3 alkyl group, a carbonyl group, or a methylene group optionally substituted by one or two groups chosen from a hydroxyl group;

R1 represents a 4-pyridine ring or a 4-pyrimidine;

R2 represents a hydrogen atom;

R3 represents:

a phenyl being optionally substituted by 1 to 4 substituents selected from a C 1-6 alkyl group, a halogen atom, a C 1-2 perhalogenated alkyl group, a C 1-6 alkoxy group, a C 1-2 perhalogenated alkoxy group, a cyano, a piperidine, or a pyrrolidine being optionally substituted by a C 1-6 alkyl group, or

a 5, 6 or 5-6 membered heteroaromatic group;

n represents 0 to 3;

m represents 0 to 1;

or an acid addition salt thereof.

3. The compound of formula (I) according to claim 2 :

wherein:

Z represents a bond, a C 1-3 alkyl group, a carbonyl group, a methylene group optionally substituted by one or two groups chosen from a hydroxyl group;

R1 represents a 4-pyridine ring or 4-pyrimidine ring;

R2 represents a hydrogen atom;

R3 represents:

a phenyl being optionally substituted by 1 to 4 substituents selected from a C 1-6 alkyl group, a halogen atom, a C 1-2 perhalogenated alkyl group, a C 1-6 alkoxy group, a C 1-2 perhalogenated alkoxy group, a cyano, a piperidine, or a pyrrolidine being optionally substituted by a C 1-6 alkyl group, or

a pyridine, an indole, an imidazopyridine, or a pyrrole;

n represents 0 to 3; and

m represents 0 to 1;

or an acid addition salt thereof.

4. The compound according to claim 1 selected from the group consisting of:

9-[3-(2-Fluoro-phenyl)-propyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-(2-Oxo-2-phenyl-ethyl)-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-(2-Oxo-2-phenyl-ethyl)-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

(—)-9-((S)-2-Hydroxy-2-phenyl-ethyl)-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Bromo-phenyl)-2-oxo-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-(2-Phenylethyl)-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-{2-[3-(4-Methyl-piperazin-1-yl)-phenyl]-2-oxo-ethyl}-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Methoxy-phenyl)-2-oxo-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Methoxy-phenyl)-2-oxo-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-Oxo-2-(3-trifluoromethyl-phenyl)-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(4-Chloro-phenyl)-2-oxo-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Bromo-phenyl)-2-oxo-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-(2-Oxo-2-pyridin-3-yl-ethyl)-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-Oxo-2-(4-pyrrolidin-1-yl-phenyl)-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-Oxo-2-(3-trifluoromethyl-phenyl)-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(4-Chloro-phenyl)-2-oxo-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-Oxo-2-(4-pyrrolidin-1-yl-phenyl)-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

3-[2-(4-Oxo-2-pyridin-4-yl-4H,10H-1,4a,9-triaza-anthracen-9-yl)-acetyl]-benzonitrile;

9-[2-(3-Fluoro-phenyl)-2-oxo-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Chloro-phenyl)-2-oxo-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Fluoro-phenyl)-2-oxo-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

3-[2-(4-oxo-2-pyrimidin-4-yl-4H,10H-1,4a,9-triaza-anthracen-9-yl)-acetyl]-benzonitrile;

9-[2-(3-Chloro-phenyl)-2-oxo-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3,5-Difluoro-phenyl)-2-oxo-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Fluoro-5-trifluoromethyl-phenyl)-2-oxo-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-Oxo-2-(3-trifluoromethoxy-phenyl)-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3,5-Bis-trifluoromethyl-phenyl)-2-oxo-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4-a,9-triaza-anthracen-4-one;

9-[2-(3,5-Difluoro-phenyl)-2-oxo-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Fluoro-5-trifluoromethyl-phenyl)-2-oxo-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-Oxo-2-(3-trifluoromethoxy-phenyl)-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-(2-Oxo-2-pyridin-4-yl-ethyl)-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-(2-Oxo-2-pyridin-3-yl-ethyl)-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-(2-Oxo-2-pyridin-2-yl-ethyl)-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-(2-Oxo-2-pyridin-4-yl-ethyl)-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(4-Fluoro-3-trifluoromethyl-phenyl)-2-oxo-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(4-Fluoro-3-trifluoromethyl-phenyl)-2-oxo-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Fluoro-4-trifluoromethyl-phenyl)-2-oxo-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Fluoro-4-trifluoromethyl-phenyl)-2-oxo-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(4-Fluoro-phenyl)-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(4-Fluoro-phenyl)-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Fluoro-phenyl)-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Chloro-phenyl)-ethyl]-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Fluoro-phenyl)-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-[2-(3-Chloro-phenyl)-ethyl]-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

2-Pyridin-4-yl-9-(2-pyridin-2-yl-ethyl)-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-(2-Pyridin-2-yl-ethyl)-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

2-Pyridin-4-yl-9-(2-pyrrol-1-yl-ethyl)-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

2-Pyridin-4-yl-9-(3-pyrrol-1-yl-propyl)-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

2-Pyrimidin-4-yl-9-(2-pyrrol-1-yl-ethyl)-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

2-Pyrimidin-4-yl-9-(3-pyrrol-1-yl-propyl)-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

9-Imidazo[1,2-a]pyridin-2-ylmethyl-2-pyridin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

(—)-9-((S)-2-Hydroxy-2-phenyl-ethyl)-2-pyrimidin-4-yl-9,10-dihydro-1,4a,9-triaza-anthracen-4-one;

10-(3-Phenyl-propyl)-2-pyridin-4-yl-10H-benzo[4,5]imidazo[1,2-a]pyrimidin-4-one;

10-[2-(1H-Indol-3-yl)-ethyl]-2-pyridin-4-yl-10H-benzo[4,5]imidazo[1,2-a]pyrimidin-4-one;

10-(2-Phenylethyl)-2-pyridin-4-yl-10H-benzo[4,5]imidazo[1,2-a]pyrimidin-4-one;

10-(4-Phenyl-butyl)-2-pyridin-4-yl-10H-benzo[4,5]imidazo[1,2-a]pyrimidin-4-one; and

10-(2-Oxo-2-phenyl-ethyl)-2-pyridin-4-yl-10H-benzo[4,5]imidazo[1,2-a]pyrimidin-4-one;

or an acid addition salt thereof.

5. A compound represented by formula (III):

wherein:

m, R1 and R2 are as defined for compound of formula (I) according to claim 1 ; with the proviso that the compound of formula (III) wherein m represents 0, R2 represents a hydrogen atom, and R1 represents a 4-pyridine ring is not included.

6. A pharmaceutical composition comprising a compound of formula (I) according to claim 1 or a pharmaceutically acceptable salt thereof and one or more pharmaceutical additives.

7. A pharmaceutical composition comprising a compound of formula (I) according to claim 2 or a pharmaceutically acceptable salt thereof and one or more pharmaceutical additives.

8. A pharmaceutical composition comprising a compound of formula (I) according to claim 3 or a pharmaceutically acceptable salt thereof and one or more pharmaceutical additives.

9. A pharmaceutical composition comprising a compound according to claim 4 or a pharmaceutically acceptable salt thereof and one or more pharmaceutical additives.