7-Imino-5-(1H-indol-3-yl)-1,3-substituted-7,8-dihdropyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione as anti-inflammatory agents
7-Imino-5-(1H-indol-3-yl)-1,3-substituted-7,8-dihydropyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione derivatives, a method of synthesizing said compounds, a pharmaceutical composition comprising said compounds and a suitable carrier, and a method of using the compounds. The present compounds, identified as COX-2 inhibitors, are useful as anti-inflammatory agents.
1. A compound having the formula I:
or a pharmaceutically acceptable salt, wherein:
R 1 is selected from the group consisting of hydrogen and methyl;
R 2 is selected from the group consisting of hydrogen and methyl; and
Y is selected from the group consisting of O and S.
2. The compound of claim 1 , wherein R 1 and R 2 are both hydrogen.
3. The compound of claim 2 , wherein Y is O or S.
4. The compound of claim 1 , wherein R 1 and R 2 are both methyl.
5. The compound of claim 4 , wherein Y is O.
6. The compound of claim 1 , wherein the compound is selected from the group consisting of:
7-Imino-5-(1H-indol-3-yl)-7,8-dihydropyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione (4a),
7-Imino-5-(1H-indol-3-yl)-2-thioxo-2,3,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(1H)-one (4b),
7-Imino-5-(1H-indol-3-yl)-1,3-dimethyl-7,8-dihydropyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione (4c),
and a pharmaceutically acceptable salt.
7. A pharmaceutically acceptable composition comprising a therapeutically effective amount of the compound of claim 1 and a pharmaceutically acceptable carrier.
8. A method of inhibiting COX-2 enzyme activity in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 1 .
9. A method of reducing inflammation in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 1 .
10. A compound having the formula I:
or a pharmaceutically acceptable salt, wherein:
R 1 and R 2 are both hydrogen or are both methyl; and
Y is selected from the group consisting of O and S.
11. A pharmaceutically acceptable composition comprising a therapeutically effective amount of the compound of claim 10 and a pharmaceutically acceptable carrier.
12. A method of inhibiting COX-2 enzyme activity in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 10 .
13. A method of reducing inflammation in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 10 .
14. A compound selected from the group consisting of:
7-Imino-5-(1H-indol-3-yl)-7,8-dihydropyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione (4a),
7-Imino-5-(1H-indol-3-yl)-2-thioxo-2,3,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(1H)-one (4b),
7-Imino-5-(1H-indol-3-yl)-1,3-dimethyl-7,8-dihydropyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione (4c),
and a pharmaceutically acceptable salt.
15. A pharmaceutically acceptable composition comprising a therapeutically effective amount of the compound of claim 14 and a pharmaceutically acceptable carrier.
16. A method of inhibiting COX-2 enzyme activity in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 14 .
17. A method of reducing inflammation in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 14 .