Tricyclic dihydrobenzofuran derivatives, process for the preparation thereof and agents
View Patent ↗A compound represented by the formula: wherein Ring A is a non-aromatic 5- to 7-membered nitrogen-containing heterocyclic ring which may be further substituted, Ring B is benzene ring which is further substituted, Ring C is a dihydrofuran-ring which may be further substituted and R is hydrogen atom or an acyl group or a salt thereof has an excellent lipid peroxidation inhibitory activity and is useful as a lipid peroxidation inhibitor.
1. A compound represented by the formula:
wherein Ring A is a non-aromatic 5- to 7-membered nitrogen-containing heterocyclic ring which may be further substituted,
Ring B is benzene ring which is further substituted,
Ring C is a dihydrofuran ring which may be further substituted and
R is hydrogen atom or an acyl group,
or a salt thereof.
2. The compound according to claim 1 , wherein Ring A is a non-aromatic 5- to 7-membered nitrogen-containing heterocyclic ring which may be further substituted by an unsubstituted or substituted hydrocarbon group.
3. The compound according to claim 1 , wherein Ring A is a non-aromatic 5- to 7-membered nitrogen-containing heterocyclic ring which may be further substituted by an unsubstituted or substituted lower alkyl group.
4. The compound according to claim 1 , wherein Ring A is a non-aromatic 5- to 7-membered nitrogen-containing heterocyclic ring which may be further substituted by a lower alkyl group.
5. The compound according to claim 1 , wherein Ring A is a non-aromatic 5-membered nitrogen-containing heterocyclic ring which may be further substituted by a lower alkyl group.
6. The compound according to claim 1 which is represented by the formula:
wherein R 4 and R 5 are the same or different and each denotes hydrogen atom, a halogen atom, hydroxy group, amino group or a hydrocarbon group which may be bonded directly or via oxygen atom, nitrogen atom or sulfur atom and which may be substituted, and the other symbols are as defined in claim 1 , provided that both R 4 and R 5 are not hydrogen atoms at the same time, or a salt thereof.
7. The compound according to claim 6 , wherein R 4 and R 5 are the same or different and each denotes a lower alkyl group or a lower alkoxy group.
8. The compound according to claim 6 , wherein each of R 4 and R 5 is a lower alkyl group.
9. The compound according to claim 1 which is represented by the formula:
wherein R 1 and R 2 are the same or different and each denotes hydrogen atom, an unesterified, esterified, unamidated or amidated carboxyl group or an unsubstituted or substituted hydrocarbon group, R 3 is hydrogen atom, an unsubstituted or substituted hydrocarbon group or an unsubstituted or substituted amino group, and the other symbols are as defined in claim 5 , or a salt thereof.
10. The compound according to claim 9 , wherein R 1 is a lower alkyl group, R 2 is a lower alkyl group which may be substituted by a halogen atom, hydroxy group or an unsubstituted or substituted cyclic amino group and R 3 is hydrogen atom or an unsubstituted or substituted phenyl group.
11. The compound according to claim 9 , wherein R 1 is a lower alkyl group, R 2 is a lower alkyl group which may be substituted by a halogen atom, hydroxy group or an unsubstituted or substituted cyclic amino group, R 3 is hydrogen atom or an unsubstituted or substituted phenyl group, each of R 4 and R 5 is a lower alkyl group, and Ring A is a non-aromatic 5- to 7-membered nitrogen-containing heterocyclic ring which may be further substituted by a lower alkyl group.
12. The compound according to claim 9 , wherein R 1 is a lower alkyl group, R 2 is a lower alkyl group which may be substituted by a halogen atom, hydroxy group or unsubstituted or substituted cyclic amino group, R 3 is hydrogen atom or an unsubstituted or substituted phenyl group, each of R 4 and R 5 is a lower alkyl group, and Ring A is a non-aromatic 5-membered nitrogen-containing heterocyclic ring which may be further substituted by a lower alkyl group.
13. 8-Tert-butyl-3,5,6,7-tetrahydro-2,2,4,6,6-pentamethyl-2H-furo[2,3-f]indole or a salt thereof.
14. 3,5,6,7-Tetrahydro-2,4,8-trimethyl-2-[(4-phenylpiperidino)methyl]-2H-furo[2,3-f]indole or a salt thereof.
15. 3,5,6,7-Tetrahydro-2,4,6,6,8-pentamethyl-2-[(4-phenylpiperidino)methyl]-2H-furo[2,3-f]indole or a salt thereof.
16. 3, 5, 6, 7-Tetrahydro-2,2,4,8-tetramethyl-3-(4-methylphenyl)-2H-furo[2,3-f]indole or a salt thereof.
17. A pharmaceutical composition comprising a compound represented by the formula:
wherein Ring A is a non-aromatic 5- to 7-membered nitrogen-containing heterocyclic ring which may be further substituted,
Ring B is benzene ring which is further substituted,
Ring C is a dihydrofuran ring which may be further substituted and
R is hydrogen atom or an acyl group,
or a salt thereof
and a pharmaceutically acceptable carrier.
18. A method for inhibiting lipid peroxidation which comprises administering an effective amount of a compound represented by the formula:
wherein Ring Aa is a non-aromatic 5- to 7-membered nitrogen-containing heterocyclic ring which may be further substituted, Ring Ba is benzene ring which may be further substituted, Ring Ca is a dihydrofuran ring which may be further substituted and Ra is hydrogen atom or an acyl group, or a salt thereof to a mammal.
19. A method for treating cranial trauma which comprises administering a compound represented by the formula:
wherein Ring Aa is a non-aromatic 5- to 7-membered nitrogen-containing heterocyclic ring which may be further substituted, Ring Ba is benzene ring which is further substituted, Ring Ca is a dihydrofuran ring which may be further substituted and Ra is hydrogen atom or an acyl group, or a salt thereof to a mammal.
20. A process for preparing the compound according to claim 1 or a salt thereof which comprises subjecting a substituent X and hydroxy group on Ring B of a compound represented by the formula:
wherein X is an unsubstituted or substituted allyl group, and the other symbols are as defined in claim 1 or a salt thereof to a ring-closure reaction.