Patent EA-000701-B1 (EA)
Title: Pentacyclic compounds
Inventor: TERASAWA HIROFUMI
IPC: C07D493/08
Filed: 1996-04-25
Abstract: 1. A compound represented by the following general formula (I) or a salt thereof   wherein R<1> represents a phenyl group, which may have one or more substituent(s) selected from the group consisting of a halogen atom, an alkyl group and an alkoxyl group; R<2> represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group or an alkoxyl group, in which these alkyl, alkenyl, alkynyl, cycloalkyl and alkoxyl groups may have one or more substituent(s) selected from the group consisting of a halogen atom, a hydroxyl group, a carboxyl group, an alkoxyl group, an aryloxy group, a phenyl group, an amino group, an alkylamino group, an alkoxycarbonyl group, an an aryloxycarbonyl group, an acyl group, an acylamino group and an acyloxy group; R<3> represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkoxyl group, a group -O-R<31>, an acyloxy group or a group -O-CO-R<31>, in which the alkoxyl and acyloxy groups may have one or more substituent(s) selected from the group consisting of a halogen atom, a hydroxyl group, a carboxyl group, a cycloalkyl group, an alkoxyl group, an aryl group, an aryloxy group, an amino group, an alkylamino group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acylamino group, an acyloxy group and a heterocyclic group (the heterocyclic group may have one or more alkyl group(s) on the constituent atoms of its ring),wherein R<31> represents an alkylamino group, an alkenyl group, an alkynyl group, a cycloalkyl group, an aryl group or a heterocyclic group, in which these alkylamino, alkenyl, alkynyl, cycloalkyl, aryl and heterocyclic groups may have one or more substituent(s) selected from the group consisting of a halogen atom, a hydroxyl group, a carboxyl group, an alkyl group, an alkoxyl group, an aryloxy group, a phenyl group, an amino group, an alkylamino group, an aminoalkyl group, an alkylaminoalkyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acylamino group, an acyloxy group and a nitrogen-containing heterocyclic group having a size of three- to eight-membered ring (the nitrogen-containing heterocyclic group may have one or more alkyl group(s) on the constituent atoms of its ring), or R<3> may form a three-membered ring together with the methyl group linked to a carbon atom adjacent to the carbon atom to which R<3> is linked; R<4> and R<5> each represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group, in which these alkyl, alkenyl, alkynyl, aryl and heterocyclic groups may have one or more substituent(s) selected from the group consisting of an alkoxyl group, an amino group, an alkylamino group, an aminoalkyl group, an alkylaminoalkyl group and a nitrogen-containing saturated heterocyclic group having a size of five- or six-membered ring represented by the following formula   wherein X represents an oxygen atom, a sulfur atom, CH2, CH-Y, NH or N-Y, in which Y is an alkyl group, (said heterocyclic group may have one or more alkyl group(s) on a carbon atom as a costituent atom of its ring), or R<4> and R<5> may form a thiocarbonyl group or a carbonyl group together with the carbon atom linked thereto; Z<1> represents a hydrogen atom, a hydroxyl group, a halogen atom or an alkyl group; Z<2> represents a hydrogen atom, a hydroxyl group, a halogen atom or an alkyl group; Z<3> represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an aryl group or a heterocyclic group, in which these alkyl, alkenyl, alkynyl, cycloalkyl, aryl and heterocyclic groups may have one or more substituent(s) selected from the group consisting of a halogen atom, a hydroxyl group, a carboxyl group, an alkyl group, an alkoxyl group, a phenyl group, an amino group, an alkylamino group, an aminoalkyl group, an alkylaminoalkyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acylamino group and an acyloxy group; and Z<4> represents an alkyl group, an aryl group or an alkoxyl group, in which these alkyl, aryl and alkoxyl groups may have one or more substituent(s) selected from the group consisting of a halogen atom, a hydroxyl group, a carboxyl group, an alkyl group, an alkoxyl group, a phenyl group, an amino group, an alkylamino group, an aminoalkyl group, an alkylaminoalkyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acylamino group and an acyloxy group;with the proviso that the dotted line of the following moiety   means that the corresponding bonding of the moiety may be a double bond, but R<3> is not a hydroxyl group in that case. 2. The compound or a salt thereof according to claim 1, wherein Z<1> and Z<2> are a fluorine atom. 3. The compound or a salt thereof according to claim 1, wherein Z<1> is a hydroxyl group and Z<2> is a hydrogen atom. 4. The compound or a salt thereof according to claim 1, wherein Z<1> is a hydroxyl group and Z<2> is a methyl group. 5. The compound or a salt thereof according to claim 1, wherein Z<4> is a phenyl group. 6. The compound or a salt thereof according to claim 1, wherein Z<4> is a tert-butoxy group. 7. The compound or a salt thereof according to claim 1, wherein Z<3> is a phenyl group. 8. The compound or a salt thereof according to claim 1, wherein Z<3> is a heterocyclic group having a size of monocyclic five- or six-membered ring. 9. The compound or a salt thereof according to claim 1, wherein Z<3> is a heterocyclic group having a size of monocyclic five- or six-membered ring and containing one oxygen, nitrogen or sulfur atom as a constituent atom of the ring structure. 10. The compound or a salt thereof according to claim 1, wherein Z<3> is an unsaturated heterocyclic group having a size of monocyclic five- or six-membered ring and containing one oxygen, nitrogen or sulfur atom as a constituent atom of the ring structure. 11. The compound or a salt thereof according to claim 1, wherein Z<3> is a furyl group, a pyrrolyl group or a pyridyl group. 12. The compound or a salt thereof according to claim 1, wherein Z<3> is a 2-methyl-1-propenyl group. 13. The compound or a salt thereof according to claim 1, wherein R<2> is an alkyl group. 14. The compound or a salt thereof according to claim 1, wherein R<2> is a methyl group, an ethyl group or a propyl group. 15. The compound or a salt thereof according to claim 1, wherein R<2> is an alkoxyl group. 16. The compound or a salt thereof according to claim 1, wherein R<2> is a methoxy group or an ethoxy group. 17. The compound or a salt thereof according to claim 1, wherein R<2> is a cycloalkyl group. 18. The compound or a salt thereof according to claim 1, wherein R<2> is a cyclopropyl group. 19. The compound or a salt thereof according to claim 1, wherein R<4> or R<5> is an alkyl group or a hydrogen atom. 20. The compound or a salt thereof according to claim 1, wherein R<4> or R<5> is an alkyl group, an alkenyl group or a phenyl group, in which said alkyl, alkenyl or phenyl group may have one or more substituent(s) selected from the group consisting of carboxyl, alkoxyl, aryloxy, alkoxycarbonyl, aryloxycarbonyl, cyano, hydroxyl, amino, alkylamino, acyl, acylamino, acyloxy, alkoxycarbonylamino, alkylthio, alkylsulfinyl, alkylsulfonyl and a nitrogen-containing saturated heterocyclic group having a size of five- or six-membered ring represented by the following formula   wherein X represents an oxygen atom, a sulfur atom, CH2, CH-Y, NH or N-Y, in which Y represents an alkyl group (said heterocyclic group may have one or more alkyl group(s) on a carbon atom as a constituent element of its ring). 21. The compound or a salt thereof according to claim 20, wherein the substituent group of said alkyl, alkenyl or phenyl group of R<4> or R<5> is an amino group, an alkylamino group or a nitrogen-containing saturated heterocyclic group having a size of five- or six-membered ring represented by the following formula   wherein X represents an oxygen atom, a sulfur atom, CH2, CH-Y, NH or N-Y, in which Y represents an alkyl group (said heterocyclic group may have one or more alkyl group(s) on a carbon atom as a constituent element of its ring). 22. The compound or a salt thereof according to claim 21, wherein said nitrogen-containing saturated heterocyclic group having a size of five- or six-membered ring is a group derived from morpholine, thiomorpholine, piperazine or a 4-alkylpiperazine. 23. The compound or a salt thereof according to claim 1, wherein R<3> is a hydroxyl group, a hydrogen atom or a fluorine atom. 24. The compound or a salt thereof according to claim 1, wherein R<3> forms a three-membered ring together with the methyl group linked to a carbon atom adjacent to the carbon atom to which R<3> is linked.