Claims
- 1. A compound having the formula ##STR6## wherein X is oxygen or sulfur, 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 provisos that:
- (i) when A is [c]pyrrole, the nitrogen atom is C.sub.1-4 alkyl-substituted, and
- (ii) when A is [b]furan, X is oxygen and n is 1, the oxazolinylamino group is attached to either the 4- or 7-position of the bicyclic moiety,
- 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 1-methyl-7-(2-oxazolin-2-yl)amino-benzo[b]pyrrole.
- 5. The compound according to claim 3 which is 1-methyl-4-(2-oxazolin-2-yl)amino-benzo[b]pyrrole.
- 6. 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.
- 7. A compound according to claim 6 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.
- 8. The compound according to claim 7 which is 5-chloro-2-methyl-4-(2-oxazolin-2-yl)amino-benzo[d]triazole.
- 9. The compound according to claim 7 which is 1-methyl-7-(2-oxazolin-2-yl)amino-benzo[d]triazole.
- 10. The compound according to claim 7 which is 5-chloro-2-methyl-4-(2-thiazolin-2-yl)amino-benzo[d]triazole.
- 11. The compound according to claim 7 which is 1-methyl-7-(2-thiazolin-2-yl)amino-benzo[d]triazole.
- 12. 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.
- 13. A compound according to claim 12 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.
- 14. The compound according to claim 13 which is 7-(2-oxazolin-2-yl)amino-benzo[b]furan.
- 15. The compound according to claim 13 which is 4-(2-oxazolin-2-yl)amino-benzo-[b]furan.
- 16. The compound according to claim 13 which is 7-(2-thiazolin-2-yl)amino-benzo[b]furan.
- 17. The compound according to claim 12 which is 5-(2-thiazolin-2-yl)amino-benzo[b]furan.
- 18. The compound according to claim 12 which is 5-(5,6-dihydro-4H-1,3-thiazin-2-yl)amino-benzo[b]furan.
- 19. A compound having the formula ##STR7## wherein X is oxygen or sulfur, 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 [b]thiophene or [c]thiophene, and
- 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, with the proviso that when A is [b]thiophene, X is oxygen and n is 1, the oxazolinylamino group is attached to either the 4- or 7-position of the bicyclic moiety, said compound being in free base or in pharmaceutically acceptable acid addition salt form.
- 20. A compound according to claim 19 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.
- 21. A compound acccording to claim 20 which is 3-methyl-7-(2-oxazolin-2-yl)amino-benzo[b]thiophene.
- 22. A compound according to claim 20 which is 4-(2-oxazolin-2-yl)amino-benzo[b]thiophene.
- 23. A compound according 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.
- 24. 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.
Priority Claims (1)
Number |
Date |
Country |
Kind |
463/77 |
Jan 1977 |
CHX |
|
Parent Case Info
This is a continuation, of application Ser. No. 869,209 filed Jan. 13, 1978, now abandoned.
US Referenced Citations (6)
Foreign Referenced Citations (2)
Number |
Date |
Country |
2040374 |
Feb 1971 |
DEX |
2257311 |
Jun 1973 |
DEX |
Continuations (1)
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Number |
Date |
Country |
Parent |
869209 |
Jan 1978 |
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