Pyrimidine, quinazoline, pteridine and triazine derivatives

Abstract

This invention is concerned with compounds of the formula

Description

Claims

1. A compound of formula I:

2. The compound according to claim 1, wherein A is O.

3. The compound according to claim 1, wherein R1 is hydrogen or halogen.

4. The compound according to claim 1, wherein R2 is selected from the group consisting of C2-7-alkyl, C2-7-alkenyl, halogen-C1-7-alkyl, C1-7-alkoxy-C1-7-alkyl and benzyl.

5. The compound according to claim 1, wherein R2 is selected from the group consisting of ethyl, propyl, isopropyl, allyl, 2-fluoroethyl, methoxymethyl, butyl, isobutyl and benzyl.

6. The compound according to claim 1, wherein R3 is selected from the group consisting of hydrogen, C1-7-alkyl, hydroxy, C1-7-alkoxy, C2-7-alkenyloxy, hydroxy-C1-7-alkoxy, C1-7-alkoxy-C1-7-alkoxy, —O—C3-7-cycloalkyl, halogen, halogen-C1-7-alkyl, —C(O)OR6, wherein R6 is C1-7-alkyl, —NH—C(O)—R7, wherein R7 is C1-7-alkyl, —S(O)—R8, wherein R8 is C1-7-alkyl, —O—SO2—R9, wherein R9 is C1-7-alkyl, amino and pyrrolyl.

7. The compound according to claim 1, wherein R3 is selected from the group consisting of hydrogen, hydroxy, C1-7-alkoxy and halogen.

8. The compound according to claim 1, wherein R3 is halogen.

9. The compound according to claim 1, wherein R3 is phenyl substituted by halogen.

10. The compound according to claim 1, wherein R4 is selected from the group consisting of hydrogen, hydroxy, C1-7-alkoxy, nitro, C1-7-alkoxy-C1-7-alkoxy, and —O-benzyl.

11. The compound according to claim 1, wherein R3 and R4 are bonded to each other to form a ring together with the carbon atoms they are attached to and R3 and R4 together are —CH═CH—CH═CH— or —O—C(CH3)2—CH═CH—.

12. The compound according to claim 1, wherein R5 is hydrogen.

13. The compound according to claim 1, wherein G is

14. The compound according to claim 1, wherein R10 is hydrogen or C1-7-alkyl;R11 is selected from the group consisting of hydrogen, C1-7-alkyl, —COOH, —CONH2, unsubstituted phenyl, phenyl substituted by one to three groups selected from the group consisting of C1-7-alkyl, C1-7-alkoxy, halogen, halogen-C1-7-alkyl, —COOH and —CONH2, and pyridyl; andR12 is hydrogen or C1-7-alkyl.

15. The compound according to claim 1, wherein G is

16. The compound according to claim 1, wherein R15 and R16 are C1-7-alkoxy.

17. The compound according to claim 1, wherein R13 is piperidinyl or morpholinyl.

18. The compound according to claim 1, wherein G is

19. The compound according to claim 1, wherein G is

20. The compound according to claim 1, wherein G is

21. The compound according to claim 1, wherein R24 and R25 independently from each other are selected from the group consisting of hydrogen, C1-7-alkyl and C1-7-alkoxy.

22. The compound according to claim 1 having the formula

23. The compound according to claim 1, selected from the group consisting of [1-(4-chloro-3-ethoxy-benzyl)-piperidin-4-yl]-(5-ethyl-pyrimidin-2-yl)-amine,[1-(4-chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-(4,6-dimethyl-pyrimidin-2-yl)-amine,[1-(3,5-diisopropoxy-benzyl)-piperidin-4-yl]-pyrimidin-2-yl-amine,[1-(4-chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-pyrimidin-2-yl-amine,2-[1-(4-chloro-3-ethoxy-benzyl)-piperidin-4-ylamino]-pyrimidine-5-carboxylic acid,2-[1-(4-chloro-3,5-diethoxy-benzyl)-piperidin-4-ylamino]-pyrimidine-5-carboxylic acid,[1-(4-chloro-3-ethoxy-benzyl)-piperidin-4-yl]-(5-phenyl-pyrimidin-2-yl)-amine,[1-(4-chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-(5-phenyl-pyrimidin-2-yl)-amine,[1-(4-chloro-3-ethoxy-benzyl)-piperidin-4-yl]-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-amine,[1-(3,5-diisopropoxy-benzyl)-piperidin-4-yl]-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-amine,[1-(4-chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-amine,[1-(4-chloro-3-ethoxy-benzyl)-piperidin-4-yl-(5-pyridin-3-yl-pyrimidin-2-yl)-amine,[1-(3,5-diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-(5-pyridin-3-yl-pyrimidin-2-yl)-amine,[1-(4-chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-(5-pyridin-3-yl-pyrimidin-2-yl)-amine,[1-(3,5-diethoxy-4-pyrrol-1-yl-benzyl)-piperidin-4-yl]-(5-pyridin-3-yl-pyrimidin-2-yl)-amine,4-{2-[1-(4-chloro-3-ethoxy-benzyl)-piperidin-4-ylamino]-pyrimidin-5-yl}-benzamide,[1-(4-chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-(6,7-dimethoxy-4-piperidin-1-yl-quinazolin-2-yl)-amine,[1-(3,5-diisopropoxy-benzyl)-piperidin-4-yl]-(6,7-dimethoxy-4-morpholin-4-yl-quinazolin-2-yl)-amine,and pharmaceutically acceptable salts thereof.

24. A process for the manufacture of a compound according to claim 1, which process comprises a) reacting a compound of the general formula G-X   II

25. A pharmaceutical composition, comprising a therapeutically effective amount of a compound according to claim 1 as well as a pharmaceutically acceptable carrier and/or adjuvant.

26. A method for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5, comprising the step of administering a therapeutically effective amount of a compound according to claim 1 to a human being or animal in need thereof.