Substituted triazinone 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;

R2 represents a hydrogen atom or a C 1-6 alkyl;

R3 represents a hydrogen atom or a C 1-6 alkyl group; or

R2 and R3 may form together a 6 membered cycle with the nitrogens caring R2 and R3 optionally substituted by 1 to 4 substituents selected from a C 1-6 alkyl group;

R4 represents:

a phenyl ring, this ring 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, or an aminosulfonyl group; and

n represents 0 to 2;

or an acid addition salt thereof.

2. A compound of formula (I):

wherein:

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

R1 represents a 4-pyridine ring;

R2 is a hydrogen or a C 1-6 alkyl group;

R3 represents a hydrogen or a C 1-6 alkyl group;

R2 and R3 may form together a 6 membered cycle, this cycle being optionally substituted by a C 1-6 alkyl group;

R4 represents a phenyl, optionally substituted by 1 to 4 substituents selected from a halogen and a C 1-6 alkoxy group; and

n represents 0, 1, or 2;

or an acid addition salt thereof.

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

(+/−)-6-(2-Hydroxy-2-phenyl-ethylamino)-1-methyl-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

1-Methyl-6-(2-phenylethyl)amino-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

(+/−)-6-(2-Hydroxy-2-phenyl-ethylamino)-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

1-Methyl-6-(2-oxo-2-phenyl-ethylamino)-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-Phenethylamino-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

1-Methyl-6-(3-phenyl-propylamino)-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-(3-Phenyl-propylamino)-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-Phenylamino-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-Benzylamino-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-[2-(2-Methoxy-phenyl)-ethylamino]-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-[2-(3-Fluoro-phenyl)-ethylamino]-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-[2-(2,4-Dichloro-phenyl)-ethylamino]-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-[2-(2-Fluoro-phenyl)-ethylamino]-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-[2-(3-Methoxy-phenyl)-ethylamino]-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

(+/−)-6-(1-Phenyl-ethylamino)-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-[2-(4-Fluoro-phenyl)-ethylamino]-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-[2-(2,5-Dimethoxy-phenyl)-ethylamino]-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-[Methyl-(2-phenylethyl)-amino)-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-((S)-2-Phenyl-propylamino)-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

6-((R)-2-Phenyl-propylamino)-4-pyridin-4-yl-1H-[1,3,5]triazin-2-one;

7,7-Dimethyl-9-(2-oxo-2-phenyl-ethyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a][1,3,5]triazin-4-one;

9-((S)-2-Hydroxy-2-phenyl-ethyl)-7,7-dimethyl-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a][1,3,5]triazin-4-one;

9-[2-(2-Fluoro-phenyl)-ethyl]-7,7-dimethyl-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a][1,3,5]triazin-4-one;

(+/−)-9-(2-Hydroxy-2-phenyl-propyl)-7,7-dimethyl-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a][1,3,5]triazin-4-one; and

7,7-Dimethyl-9-(3-phenyl-propyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a][1,3,5]triazin-4-one;

or an acid addition salt thereof.

4. 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.

5. 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.

6. A pharmaceutical composition comprising a compound according to claim 3 or a pharmaceutically acceptable salt thereof and one or more pharmaceutical additives.

7. A method of treating a neurodegenerative disease in a patient comprising administering to said patient a therapeutically effective amount of a compound of formula (I) according to claim 1 or a pharmaceutically acceptable salt thereof, wherein the neurodegenerative disease is Alzheimer's disease.

8. A method of treating a disease in a patient, comprising administering to said patient a therapeutically effective amount of a compound of formula (I) according to claim 1 or a pharmaceutically acceptable salt thereof, wherein said disease is selected from the group consisting of non-insulin dependent diabetes; obesity; and schizophrenia.

9. The method according to claim 8 , wherein the disease is selected from non-insulin dependent diabetes and obesity.