Claims
- 1. A compound of the formula
- 2. A compound according to claim 1 where the pharmaceutically acceptable salts are selected from the group consisting of salts of the following acids hydrochloric, hydrobromic, sulfuric, phosphoric, nitric, citric, methanesulfonic, CH3—(CH2)n1—COOH where n1 is 0 thru 4, HOOC—(CH2)n1—COOH where n is as defined above, HOOC—CH═CH—COOH and φ-COOH.
- 3. A compound according to claim 1 which is
- 4. A compound according to claim 3 which is
- 5. (5R)-5-(methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione and pharmaceutically acceptable salts thereof.
- 6. A compound according to claim 5 where the pharmaceutically acceptable salts are selected from the group consisting of consisting of salts of the following acids hydrochloric, hydrobromic, sulfuric, phosphoric, nitric, citric, methanesulfonic, CH3—(CH2)n1—COOH where n1 is 0 thru 4, HOOC—(CH2)n1—COOH where n is as defined above, HOOC—CH═CH—COOH and φ-COOH.
- 7. A compound according to claim 5 which is (5R)-5-(methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione.
- 8. A compound according to claim 7 which is (5R)-5-(methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione maleate.
- 9. A process for the preparation of (5R)-(methylamino)5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione which comprises:
(1) contacting (5R)-(methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-one or pharmaceutically acceptable salts thereof with tetraphosphorous decasulfide and (2) heating to more than 100°.
- 10. A process according to claim 9 where the heating is to about 125°.
- 11. A process according to claim 9 where the solvent is pyridine.
- 12. A process according to claim 9 where the (5R)-(methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-one is present as the free base.
- 13. A process according to claim 9 where the pharmaceutically acceptable salt is selected from the group consisting of the salts of the following acids hydrochloric, hydrobromic, sulfuric, phosphoric, nitric, citric, methanesulfonic CH3—(CH2)n1—COOH where n1 is 0 thru 4, HOOC—(CH2)n1—COOH where n is as defined above, HOOC—CH═CH—COOH, φ-COOH.
- 14. A process according to claim 9 where the (5R)-(methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-one is present as the hydrochloride salt.
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application claims the benefit of the following provisional applications: U.S. Ser. No. 60/199954, filed Apr. 27, 2000, and U.S. Ser. No. 60/234101, filed Sep. 21, 2000, under 35 USC 119(e)(i).
Provisional Applications (2)
|
Number |
Date |
Country |
|
60199954 |
Apr 2000 |
US |
|
60234101 |
Sep 2000 |
US |
Continuations (2)
|
Number |
Date |
Country |
Parent |
10634355 |
Aug 2003 |
US |
Child |
10898299 |
Jul 2004 |
US |
Parent |
09838054 |
Apr 2001 |
US |
Child |
10634355 |
Aug 2003 |
US |