Claims
- 1. A compound of formula
- 2. The compound of claim 1 having the formula
- 3. The compound of claim 1 having the formula
- 4. The compound of formula Ie in accordance with claim 15, wherein R1 and R2 are each independently selected from lower alkyl, halogen and CF3; R3 is lower alkyl or hydrogen; and R4, R5,R6, and R6′ are hydrogen.
- 5. The compound of formula Ie in accordance with claim 16, which is selected from the group consisting of
3-(3,4-dimethyl-phenyl)-5-(2-methyl-imidazol-1-yl-methyl)-pyridine; 3-(4-fluoro-3-methyl-phenyl)-5-(2-methyl-imidazol-1-yl-methyl)-pyridine; 3-(4-chloro-3-methyl-phenyl)-5-(2-methyl-imidazol-1-yl-methyl)-pyridine; 3-(3-chloro-4-fluoro-phenyl)-5-(2-methyl-imidazol-1-yl-methyl)-pyridine; and 3-(4-chloro-3-trifluoromethyl-phenyl)-5-(2-methyl-imidazol-1-yl-methyl)-pyridine.
- 6. The compound of claim 1 having the formula
- 7. The compound of formula If in accordance with claim 18, wherein and R1 and R2 are each independently selected from halogen; R3 is lower alkyl; and R4, R5,R6, and R6′ are hydrogen.
- 8. The compound of formula If in accordance with claim 19, which is 4-(3,4-dichloro-phenyl)-2-(2-methyl-imidazol-1-yl-methyl)-pyridine.
- 9. The compound of claim 1 having the formula
- 10. The compound of formula Ig in accordance with claim 21, wherein R1 and R2 are each independently selected from halogen; R3 is lower alkyl; and R4, R5,R6, and R6′ are hydrogen.
- 11. The compound of formula Ig in accordance with claim 22, which is 2-(3,4-dichloro-phenyl)-4-(2-methyl-imidazol-1-yl-methyl)-pyridine.
- 12. The compound of claim 1 wherein A is pyridin-2-yl, pyridin-3-yl, or pyridin-1-yl.
- 13. A compound of formula
- 14. A compound selected from the group
3-(3-Difluoromethyl-4-fluoro-phenyl)-5-(2-methyl-imidazol-1-ylmethyl)-pyridine; 3-[3-(1,1-Difluoro-ethyl)-phenyl]-5-(2-methyl-imidazol-1-ylmethyl)-pyridine; 3-(3-Fluoro-5-trifluoromethyl-phenyl)-5-(2-methyl-imidazol-1-ylmethyl)-pyridine; 3-[3-(1,1-Difluoro-ethyl)-4-fluoro-phenyl]-5-(2-methyl-imidazol-1-ylmethyl)-pyridine; and 2-[5-(2-Methyl-imidazol-1-ylmethyl)-pyridin-3-yl]-1,2,3,4-tetrahydro-isoquinoline hydrochloride (1:2).
- 15. A pharmaceutical composition comprising one or more compounds of formula I or a pharmaceutically acceptable salt thereof, and an inert carrier.
- 16. A method of making a compound of formula I comprising:
reacting a compound of formula 46with a compound of formula 47to give a compound of formula 48wherein A is phenyl, pyridin-2 or 3-yl; R1 and R2 are each independently selected from the group consisting of hydrogen, halogen, lower alkyl, cycloalkyl, lower alkenyl, trifluoromethyl, —O-trifluoromethyl, —S-trifluoromethyl, S-lower alkyl, lower alkoxy, —CHF2, —C(lower alkyl)F2, —OCHF2, phenyl, nitro, benzyloxy, hydroxy and amino, or alternatively, R1 and R2 together with the carbon atoms to which they are attached in any adjacent positions from a group selected from —CH═CH—CH═CH—, —CH═CH—CH═N—, —(CH2)3—, —O—CH2—O—, —O—CF2—O—, —CH2—O—CH2— and —CH2CH2—O—; R3 is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl, phenyl, S-lower alkyl, amino, lower alkyl-amino, —NHC(O)-lower alkyl and hydroxy-lower alkyl; R4 and R5 are each independently selected from hydrogen and lower alkyl, or alternatively, R4 and R5 together with the carbon atom to which they are attached form the group —(CH2)4—; R6 and R6′ are each independently selected from hydrogen and lower alkyl; and R7 is hydrogen, —CH2OH or lower alkyl; and hal is Cl or Br.
- 17. A method of making a compound of formula I comprising:
reacting a compound of formula 49with a compound of formula 50to give a compound of formula 51wherein A is phenyl, pyridin-2 or 3-yl; R1 and R2 are each independently selected from the group consisting of hydrogen, halogen, lower alkyl, cycloalkyl, lower alkenyl, trifluoromethyl, —O-trifluoromethyl, —S-trifluoromethyl, S-lower alkyl, lower alkoxy, —CHF2, —C(lower alkyl)F2, —OCHF2, phenyl, nitro, benzyloxy, hydroxy and amino, or alternatively, R1 and R2 together with the carbon atoms to which they are attached in any adjacent positions from a group selected from —CH═CH—CH═CH—, —CH═CH—CH═N—, —(CH2)3—, —O—CH2—O—, —O—CF2—O—, —CH2—O—CH2— and —CH2CH2—O—; R3 is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl, phenyl, S-lower alkyl, amino, lower alkyl-amino, —NHC(O)-lower alkyl and hydroxy-lower alkyl; R4 and R5 are each independently selected from hydrogen and lower alkyl, or alternatively, R4 and R5 together with the carbon atom to which they are attached form the group —(CH2)4—; R6 and R6′ are each independently selected from hydrogen and lower alkyl; and hal is Cl or Br.
- 18. A method of making a compound of formula I comprising:
reacting a compound of formula 52with a compound of formula 53to give a compound of formula 54wherein A is phenyl, pyridin-2 or 3-yl; R1 and R2 are each independently selected from the group consisting of hydrogen, halogen, lower alkyl, cycloalkyl, lower alkenyl, trifluoromethyl, —O-trifluoromethyl, —S-trifluoromethyl, S-lower alkyl, lower alkoxy, —CHF2, —C(lower alkyl)F2, —OCHF2, phenyl, nitro, benzyloxy, hydroxy and amino, or alternatively, R1 and R2 together with the carbon atoms to which they are attached in any adjacent positions from a group selected from —CH═CH—CH═CH—, —CH═CH—CH═N—, —(CH2)3—, —O—CH2—O—, —O—CF2—O—, —CH2—O—CH2— and —CH2CH2—O—; R3 is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl, phenyl, S-lower alkyl, amino, lower alkyl-amino, —NHC(O)-lower alkyl and hydroxy-lower alkyl; R4 and R5 are each independently selected from hydrogen and lower alkyl, or alternatively, R4 and R5 together with the carbon atom to which they are attached form the group —(CH2)4—; R6 and R6′ are each independently selected from hydrogen and lower alkyl; and hal is Cl or Br.
- 19. A method of treating an NMDA-receptor-mediated disease comprising administering to a patient in need of such treatment an effective amount of a compound of claim 1.
- 20. The method of claim 35 wherein the NMDA-receptor disease is acute neurodegeneration caused by stroke or brain trauma.
- 21. The method of claim 35 wherein the NMDA-receptor disease is chronic neurodegeneration caused by Alzheimer's disease, Parkinson's disease, Huntington's disease, or ALS (amyotrophic lateral sclerosis).
Priority Claims (1)
Number |
Date |
Country |
Kind |
01101947.8 |
Jan 2001 |
EP |
|
CONTINUITY INFORMATION
[0001] This application is a divisional of Ser. No. 10/029,342, filed Dec. 20, 2001.
Divisions (1)
|
Number |
Date |
Country |
Parent |
10029342 |
Dec 2001 |
US |
Child |
10364596 |
Feb 2003 |
US |