Claims
- 1. A compound having the formula ##STR6## wherein the heterocyclic amino moiety is bonded to the benzene ring of the bicyclic moiety,
- n is an integer 1 or 2,
- R.sub.1, which is bonded to the benzene ring of the bicyclic moiety, is hydrogen, halo, C.sub.1-4 -alkyl, C.sub.1-4 alkylthio, C.sub.1-4 alkoxy, trifluoromethyl or hydroxy,
- A is a five-membered heterocyclic ring selected from the group consisting of [b]pyrrole, [c]pyrrole, [d]triazole, [b]furan, [c]furan, [c]furazan, [d](1,2,3)-thiadiazole, [b]pyrroline, [c]pyrroline, [b]dihydrofuran, [c]dihydrofuran, [b]dihydrothiophene, [c]isoxazole and [d]isoxazole,
- R.sub.2, which is bonded to the A ring of the bicyclic moiety and attached to a carbon atom of said ring, is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, trifluoromethyl or hydroxy, and
- R.sub.3, which is bonded to the A ring of the bicyclic moiety and attached to a nitrogen atom of said ring, is hydrogen or C.sub.1-4 alkyl, with the proviso that when A is [c]pyrrole, the nitrogen atom of said pyrrole ring is C.sub.1-4 alkylsubstituted,
- said compound being in free base or in pharmaceutically acceptable acid addition salt form.
- 2. A compound according to claim 1 wherein A is [b]pyrrole, said compound being in free base or in pharmaceutically acceptable acid addition salt form.
- 3. A compound according to claim 2 wherein the heterocyclic amino moiety is bonded to the 4- or 7-position of the bicyclic moiety, said compound being in free base or in pharmaceutically acceptable acid addition salt form.
- 4. The compound according to claim 3 which is 4-(2-imidazolin-2-yl)amino-benzo[b]pyrrole.
- 5. The compound according to claim 3 which is 7-(2-imidazolin-2-yl)amino-benzo[b]pyrrole.
- 6. The compound according to claim 3 which is 7-(2-imidazolin-2-yl)amino-1-methyl-benzo[b]pyrrole.
- 7. A compound according to claim 1 wherein A is [d]triazole, said compound being in free base or in pharmaceutically acceptable acid addition salt form.
- 8. A compound according to claim 7 wherein the heterocyclic amino moiety is bonded to the 4- or 7-position of the bicyclic moiety, said compound being in free base or in pharmaceutically acceptable acid addition salt form.
- 9. The compound according to claim 8 which is 4-(2-imidazolin-2-yl)amino-benzo[d]triazole.
- 10. The compound according to claim 8 which is 4-(2-imidazolin-2-yl)amino-5-methyl-benzo[d]triazole.
- 11. The compound according to claim 8 which is 5-chloro-4-(2-imidazolin-2-yl)amino-benzo[d]triazole.
- 12. The compound according to claim 8 which is 4-(2-imidazolin-b 2-yl)amino-1-methyl-benzo[d]triazole.
- 13. The compound according to claim 8 which is 4-(2-imidazolin-2-yl)amino-5-methoxy-1-methyl-benzo[d]triazole.
- 14. The compound according to claim 8 which is 5-chloro-4-(2-imidazolin-2-yl)amino-1-methyl-benzo[d]triazole.
- 15. The compound according to claim 8 which is 7-(2-imidazolin-2-yl)amino-1-methyl-benzo[d]triazole.
- 16. The compound according to claim 8 which is 4-(2-imidazolin-2-yl)amino-2-methyl-benzo[d]triazole.
- 17. The compound according to claim 8 which is 4-(2-imidazolin-2-yl)amino-5-methoxy-2-methyl-benzo[d]triazole.
- 18. The compound according to claim 8 which is 5-chloro-4-(2-imidazolin-2-yl)amino-2-methyl-benzo[d]triazole.
- 19. The compound according to claim 8 which is 1-methyl-7-([3,4,5,6-tetrahydropyrimidin-2-yl]amino)-benzo[d]triazole.
- 20. The compound according to claim 8 which is 2-methyl-4-([3,4,5,6-tetrahydropyrimidin-2-yl]amino)-benzo[d]triazole.
- 21. A compound according to claim 1 wherein A is [b]furan, said compound being in free base or in pharmaceutically acceptable acid addition salt form.
- 22. A compound according to claim 21 wherein the heterocyclic amino moiety is bonded to the 4- or 7-position of the bicyclic moiety, said compound being in free base or in pharmaceutically acceptable acid addition salt form.
- 23. The compound according to claim 22 which is 7-(2-imidazolin-2-yl)amino-benzo[b]furan.
- 24. A compound acccording to claim 1 wherein A is [d](1,2,3)-thiadiazole, said compound being in free base or in pharmaceutically acceptable acid addition salt form.
- 25. The compound according to claim 24 which is 6-chloro-7-(2-imidazolin-b 2-yl)amino-benzo[d](1,2,3)-thiadiazole.
- 26. A compound according to claim 1 wherein A is [c]furazan, said compound being in free base or in pharmaceutically acceptable acid addition salt form.
- 27. The compound according to claim 26 which is 4-(2-imidazolin-2-yl)amino-5-methyl-benzo[c]furazan.
- 28. The compound according to claim 26 which is 4-(2-imidazolin-2-yl)amino-benzo[c]furazan.
- 29. The compound according to claim 26 which is 4-(2-imidazolin-2-yl)amino-5-methoxy-benzo[c]furazan.
- 30. The compound according to claim 26 which is 5-chloro-4-(2-imidazolin-2-yl)amino-benzo[c]furazan.
- 31. The compound according to claim 26 which is 5-(2-imidazolin-2-yl)amino-benzo[c]furazan.
- 32. The compound according to claim 26 which is 7-chloro-4-(2-imidazolin-2-yl)amino-benzo[c]furazan.
- 33. The compound according to claim 26 which is 4-bromo-5-(2-imidazolin-2-yl)amino-benzo[c]furazan.
Parent Case Info
This is a division of application Ser. No. 14,213, filed Feb. 22, 1979, now issued as U.S. Pat. No. 4,297,490, which in turn is a continuation of application Ser. No. 869,209, filed Jan. 13, 1978, now abandoned.
US Referenced Citations (5)
Foreign Referenced Citations (1)
Number |
Date |
Country |
54-12374 |
Jan 1979 |
JPX |
Divisions (1)
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Number |
Date |
Country |
Parent |
14213 |
Feb 1979 |
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Continuations (1)
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Number |
Date |
Country |
Parent |
869209 |
Jan 1978 |
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