Claims
- 1. A compound of formulae
- 2. A compound of formula
- 3. A compound of formula IA-1 according to claim 2, selected from the group
trans-4-methyl-6-styryl-pyridin-2-yl-amine, trans-2-styryl-pyridin-4-yl-amine and trans-C-(6-styryl-pyridin-2-yl)-methylamine.
- 4. A compound of formula
- 5. A compound of formula IA-2 according to claim 4, wherein R′ is hydrogen.
- 6. A compound of formula IA-2 according to claim 5, selected from the group
2-(3,4-dihydro-naphthalen-2-yl)-pyridin-4-yl-amine, 2-(3,4-dihydro-naphthalen-2-yl)-6-methyl-pyridin-4-yl-amine, [4-amino-6-(3,4-dihydro-naphthalen-2-yl)-pyridin-2-yl]-methanol, 2-(3,4-dihydro-naphthalen-2-yl)-5-methyl-pyridin-4-yl-amine, 2-(3,4-dihydro-naphthalen-2-yl)-6-ethyl-pyridin-4-yl-amine, 2-(3,4-dihydro-naphthalen-2-yl)-pyridin-4-yl]-methyl-amine, C-[6-(3,4-dihydro-naphthalen-2-yl)-pyridin-2-yl]-methylamine, 2-(7-chloro-3,4-dihydro-naphthalen-2-yl)-pyridin-4-yl-amine, 2-(5,7-dimethyl-3,4-dihydro-naphthalen-2-yl)-pyridin-4-yl-amine, 2-(7-chloro-3,4-dihydro-naphthalen-2-yl)-6-ethyl-pyridin-4-yl-amine, 2-(7-chloro-3,4-dihydro-naphthalen-2-yl)-6-methyl-pyridin-4-yl-amine and 2-(7-chloro-3,4-dihydro-naphthalen-2-yl)-5-methyl-pyridin-4-yl-amine.
- 7. A compound of formula IA-2 according to claim 4, wherein R′ is methyl.
- 8. A compound of formula IA-2 according to claim 7, selected from the group
rac.-2-(4-methyl-3,4-dihydro-naphthalen-2-yl)-pyridin-4-yl-amine, rac.-2-methyl-6-(4-methyl-3,4-dihydro-naphthalen-2-yl)-pyridin-4-yl-amine and rac.-5-methyl-2-(4-methyl-3,4-dihydro-naphthalen-2-yl)-pyridin-4-yl-amine.
- 9. A compound of formula
- 10. A compound of formula IA-4 according to claim 9, wherein R′ is hydrogen.
- 11. A compound of formula IA-4 according to claim 10, selected from the group
2-(6,7-dihydro-benzo[b]thiophen-5-yl)-pyridin-4-yl-amine and 2-(6,7-dihydro-benzo[b]thiophen-5-yl)-5-methyl-pyridin-4-yl-amine.
- 12. A compound of formula
- 13. A compound of formula IB-1 according to claim 12, which is trans-6-methyl-4-styryl-pyridin-2-yl-amine.
- 14. A compound of formula IA or IB according to claim 1, wherein one of R1 or R2 is amino.
- 15. A pharmaceutical composition comprising a compound of formula IA or IB of claim 1, combinations thereof or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
- 16. A method of treatment of diseases responsive to therapeutic indications for NMDA receptor subtype specific blockers, such as Alzheimer's disease, Parkinson's disease, Huntington's disease, ALS (amyotrophic lateral sclerosis) and neurodegeneration associated with bacterial or viral infections, and, in addition, depression and chronic or acute pain comprising administering a therapeutically effective amount of a compound of formulae 1A or IB according to claim 1, combinations thereof or a pharmaceutically acceptable salt thereof to a patient in need of such treatment.
- 17. A process for preparing a compound of formula IA-1a comprising
a) reacting a compound of formula 26 with diphenyl phosphoryl azide, forming a compound of formula 27 wherein
R2 is selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH; R5 and R5′ are each independently hydrogen or lower alkyl; and R3 and R4 are each independently selected from the group hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy; Ar is selected from the group phenyl and thiophenyl and n is 0, 1 or 2.
- 18. A process for preparing a compound of formula IA-1b comprising
reacting the amino group of a compound of formula 28 with a compound of formula R5X, forming a compound of formula 29 wherein
R2 is selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —CH2)n+1OH; R3 and R4 are each independently selected from the group hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy; Ar is selected from the group phenyl and thiophenyl; R5 is lower alkyl; X is halogen; and; n is 0, 1 or 2.
- 19. A process for preparing a compound of formulae IIB-1a, comprising:
reacting a compound of formula 30 with diphenyl phosphoryl azide forming a compound of formula 31 wherein
R2 is selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —CH2)n+1OH; R3 and R4 are each independently selected from the group hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy; Ar is selected from the group phenyl and thiophenyl; R5 is lower alkyl; and; n is 0, 1 or 2.
- 20. A process for preparing a compound of formula IIB-1b comprising:
reacting the amino group of a compound of formula 32 with a compound of formula R5X forming a compound of formula 33 wherein
R1 is selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH; R5 and R5′ are each independently hydrogen or lower alkyl; R3 and R4 are each independently selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy; Ar is selected from the group phenyl and thiophenyl; X is halogen; and n is 0, 1 or 2.
- 21. A process for preparing a compound of formulae IA-2 comprising:
reacting a compound of formula 34 with a compound of formula 35 forming a compound of formula 36 wherein
R1 and R2 are each independently selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH; R5 and R5′ are each independently hydrogen or lower alkyl; and R3 and R4 are each independently selected from the group hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy; and n is 0, 1 or 2.
- 22. A process for preparing a compound of formula IB-2 comprising:
reacting a compound of formula 37 with a compound of formula 38 forming a compound of formula 39 wherein
R1 and R2 are each independently selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH; R5 and R5′ are each independently hydrogen or lower alkyl; and R3 and R4 are each independently selected from the group hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy; and n is 0, 1 or 2.
Priority Claims (1)
Number |
Date |
Country |
Kind |
01125765.6 |
Oct 2001 |
EP |
|
PRIORITY TO RELATED APPLICATIONS
[0001] This application is a Division of Ser. No. 10/277,002, filed Oct. 21, 2002.
Divisions (1)
|
Number |
Date |
Country |
Parent |
10277002 |
Oct 2002 |
US |
Child |
10672950 |
Sep 2003 |
US |