Patent ID: 6211178
Filing Date: 2001-04-03
Classification: A01N,C07C,C07D

Abstract:
A compound or a salt thereof wherein said compound has a structure of the formula: ##STR270##wherein ring A is an aromatic group which may be substituted with 1 to 5 substituents selected from the group consisting of (1) C.sub.1-4 alkyl, (2) C.sub.2-4 alkenyl, (3) C.sub.2-4 alkynyl, (4) C.sub.3-5 cycloalkyl, (5) C.sub.5-7 cycloalkenyl, (6) C.sub.7-11 aralkyl, (7) phenyl, (8) C.sub.1-6 alkoxy, (9) phenoxy, (10) C.sub.1-6 alkanoyl, (11) benzoyl, (12) C.sub.1-6 alkanoyloxy, (13) carboxyl, (14) C.sub.2-7 alkoxycarbonyl, (15) carbamoyl, (16) N-mono-C.sub.1-6 alkylcarbamoyl, (17) N-di-C.sub.1-4 alkylcarbamoyl, (18) cycloaminocarbonyl, (19) halogen, (20) mono-, di- or tri-halo-C.sub.1-4 alkyl, (21) oxo, (22) amidino, (23) imino, (24) amino which may be protected with a group selected from (i) formyl, (ii) C.sub.1-6 alkyl-carbonyl which may be substituted with halogen atoms, (iii) C.sub.6-10 aryl-carbonyl which may be substituted with 1 to 3 halogen atoms, C.sub.1-6 alkylcarbonyl or nitro group, (iv) C.sub.1-6 alkyloxycarbonyl which may be substituted with 1 to 3 halogen atoms, C.sub.1-6 alkylcarbonyl or nitro group, (v) C.sub.6-10 aryloxycarbonyl which may be substituted with 1 to 3 halogen atoms, C.sub.1-6 alkylcarbonyl or nitro group, (vi) C.sub.7-12 aralkyl-carbonyl which may be substituted with 1 to 3 halogen atoms, C.sub.1-6 alkylcarbonyl or nitro group, (vii) trityl which may be substituted with 1 to 3 halogen atoms, C.sub.1-6 alkylcarbonyl or nitro group and (viii) phthaloyl which may be substituted with 1 to 3 halogen atoms, C.sub.1-6 alkylcarbonyl or nitro group, (25) mono-C.sub.1-4 alkylamino, (26) di-C.sub.1-4 alkylamino, (27) 3- to 6-membered cycloamino which may contain 1 to 3 hetero atoms selected from oxygen, sulfur and nitrogen, (28) C.sub.1-6 alkanamido, (29) benzamido, (30) carbamoylamino, (31) N--C.sub.1-4 alkylcarbamoylamino, (32) N,N-di-C.sub.1-4 alkylcarbamoylamino, (33) C.sub.1-3 alkylenedioxy, (34) --B(OH).sub.2, (35) hydroxy, (36) epoxy, (37) nitro, (38) cyano, (39) mercapto, (40) sulfo, (41) sulfino, (42) phosphono, (43) dihydroxypolyol, (44) sulfamoyl, (45) mono-C.sub.1-6 alkylsulfamoyl, (46) di-C.sub.1-4 alkylsulfamoyl, (47) C.sub.1-6 alkylthio, (48) phenylthio, (49) C.sub.1-6 alkylsulfinyl, (50) phenylsulfinyl, (51) C.sub.1-6 alkylsulfonyl, (52) phenylsulfonyl and (53) 5- or 6-membered heterocyclic group containing 1 to 4 hetero atoms selected from oxygen, sulfur and nitrogen, which may bound through one or two atomic chain containing oxygen, sulfur, nitrogen and carbon, in which any group having a carbon chain of 2 or more carbon atoms or a cyclic group may be further substituted with one or two substituents selected from the group consisting of (a) halogen, (b) hydroxy, (c) oxo, (d) C.sub.1-4 alkoxy, (e) di-C.sub.1-4 alkylamino, (f) halo-C.sub.1-4 alkyl, (g) C.sub.1-4 acyl, (h) hydroxy-C.sub.1-4 alkyl, (i) C.sub.1-4 alkoxy-C.sub.1-4 alkyl, (j) cyano, (k) thioxo and (l) C.sub.1-4 alkylthio, and in which when the substituent mentioned above exists on two ring-forming atoms adjacent to each other, they may bind together to form a ring:X is oxygen or sulfur;R.sup.1 is hydrogen, C.sub.1-7 acyl, C.sub.1-7 alkyloxycarbonyl, C.sub.1-4 alkyl, mono-, di- or trihalo-C.sub.1-4 alkyl, or C.sub.1-4 alkylcarbonyl;R.sup.2 and R.sup.3 are independently selected from the group consisting of a hydrogen atom, a halogen atom, cyano, carboxy, carbamoyl, mercapto, hydroxy, C.sub.1-4 alkyl, C.sub.1-6 alkylthio, C.sub.7-11 aralkylthio, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-6 alkoxy, C.sub.3-6 cycloalkyl, C.sub.6-10 aryl and a 5- to 7-membered heterocyclic group containing one to four hetero-atoms selected from group consisting of nitrogen, sulfur and oxygen, wherein the alkyl, alkylthio, aralkylthio, alkenyl, alkynyl, alkoxy, cycloalkyl, aryl or heterocyclic group may have one or two substituents selected from the group consisting of (a) halogen, (b) hydroxy, (c) oxo, (d) C.sub.1-4 alkoxy, (e) di-C.sub.1-4 alkylamino, (f) halo-C.sub.1-4 alkyl, (g) C.sub.1-4 acyl, (h) hydroxy-C.sub.1-4 alkyl, (i) C.sub.1-4 alkoxy-C.sub.1-4 alkyl, (j) thioxo, (k) sulfide, (l) C.sub.3-6 cycloalkyl and (m) mercapto, or when taken together, R.sup.2 and R.sup.3 represent .dbd.S;R.sup.4 and R.sup.5 are independently selected from the group consisting of a hydrogen atom, a halogen atom, cyano, carboxy, carbamoyl, amino, nitro, hydroxy, mercapto, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-6 cycloalkyl, C.sub.6-10 aryl and a 5- to 7-membered heterocyclic group containing one to four hetero-atoms selected from the group consisting of nitrogen, sulfur and oxygen, wherein the alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclic group may have one or two substituent groups selected from the group consisting of (a) halogen, (b) hydroxy, (c) oxo, (d) C.sub.1-4 alkoxy, (e) di-C.sub.1-4 alkylamino, (f) halo-C.sub.1-4 alkyl, (g) C.sub.1-4 acyl, (h) hydroxy-C.sub.1-4 alkyl and (i) C.sub.1-4 alkoxy-C.sub.1-4 alkyl;R.sup.6 is selected from the group consisting of(1) a hydrogen atom,(2) a hydrocarbon residue selected from the group consisting of C.sub.1-15 alkyl, C.sub.3-8 cycloalkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, C.sub.3-10 cycloalkenyl, C.sub.6-14 aryl and C.sub.7-16 aralkyl, each of which may have one to five substituent groups selected from the group consisting of (1) nitro, (2) hydroxy, (3) oxo, (4) thioxo, (5) cyano, (6) carbamoyl, (7) carboxyl, (8) C.sub.1-4 alkoxycarbonyl, (9) sulfo, (10) halogen, (11) C.sub.1-4 alkoxy, (12) phenoxy, (13) halophenoxy, (14) C.sub.1-4 alkylthio, (15) phenylthio, (16) C.sub.1-4 alkylsulfinyl, (17) C.sub.1-4 alkylsulfonyl, (18) amino, (19) C.sub.1-6 acylamino, (20) mono- or di-C.sub.1-4 alkylamino, (21) C.sub.1-4 acyl, (22) benzoyl, (23) 5- or 6-membered heterocyclic group containing one to four hetero-atoms selected from the group consisting of oxygen, sulfur and nitrogen, which may be substituted by one to four substituents selected from the group consisting of (a) halogen, (b) C.sub.1-4 alkyl and (c) halophenoxy, and (24) C.sub.1-10 haloalkyl, and where the hydrocarbon group is cycloalkyl, cycloalkenyl, aryl or aralkyl, each of which may have one to four C.sub.1-4 alkyl group,(3) an acyl group selected from the group consisting of --COR.sup.a, --CONHR.sup.a, --CSR.sup.a and --CSNHR.sup.a wherein R.sup.a represents hydrogen or a hydrocarbon group selected from the group consisting of C.sub.1-15 alkyl, C.sub.3-8 cycloalkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, C.sub.3-10 cycloalkenyl, C.sub.6-14 aryl and C.sub.7-16 aralkyl, wherein each hydrocarbon group may be substituted with one or two substituent groups selected from the group consisting of (1) nitro, (2) hydroxy, (3) oxo, (4) thioxo, (5) cyano, (6) carbamoyl, (7) carboxyl, (8) C.sub.1-4 alkoxycarbonyl, (9) sulfo, (10) halogen, (11) C.sub.1-4 alkoxy, (12) phenoxy, (13) halophenoxy, (14) C.sub.1-4 alkylthio, (15) phenylthio, (16) C.sub.1-4 alkylsulfinyl, (17) C.sub.1-4 alkylsulfonyl, (18) amino, (19) C.sub.1-6 acylamino, (20) mono- or di-C.sub.1-4 alkylamino, (21) C.sub.1-4 acylt (22) benzoyl, and (23) 5- or 6-membered heterocyclic group containing one to four hetero-atoms selected from the group consisting of oxygen, sulfur and nitrogen, which may be substituted by one to four substituents selected from the group consisting of (a) halogen, (b) C.sub.1-4 alkyl and (c) halophenoxy, and when the hydrocarbon group is cycloalkyl, cycloalkenyl, aryl or aralkyl, each may have one to four C.sub.1-4 alkyl groups,(4) an oxycarbonyl group of the formula --COOR.sup.a wherein R.sup.a is as defined above, and(5) a 5- to 8-membered heterocyclic group or condensed heterocyclic group derived therefrom containing one to four hetero-atoms selected from the group consisting of oxygen sulfur and nitrogen, which may have one to five substituent groups selected from the group consisting of (1) C.sub.1-4 alkyl, (2) C.sub.2-4 alkeyl, (3) C.sub.2-4 alkynyl, (4) C.sub.3-6 cycloalkyl, (5) C.sub.5-7 cycloalkenyl, (6) C.sub.7-11 aralkyl, (7) phenyl, (8) C.sub.1-6 alkoxy, (9) phenoxy, (10) C.sub.1-6 alkanoyl, (11) benzoyl, (12) C.sub.1-6 alkanoyloxy, (13) carboxyl, (14) C.sub.2-7 alkoxycarbonyl, (15) carbamoyl (16) N-mono-C.sub.1-4 alkylcarbamoyl, (17) N,N-di-C.sub.1-4 alkylcarbamoyl, (18) cycloaminocarbonyl, (19) halogen, (20) mono-, di- or trihalo-C.sub.1-4 alkyl, (21) oxo, (22) amidino, (23) imino, (24) amino, (25) mono-C.sub.1-4 alkylamino, (26) di-C.sub.1-4 alkylamino, (27) 3- to 6-membered cycloamino containing 1 to 3 hetero-atoms selected from oxygen, sulfur, and nitrogen, (28) C.sub.1-6 alkanoylamido, (29) benzamido, (30) carbamoylamino, (31) N--C.sub.1-4 alkylcarbamoylamino, (32) N,N-di-C.sub.1-4 alkylcarbamoylamino, (33) C.sub.1-3 alkylenedioxy, (34) --B(OH).sub.2, (35) hydroxy, (36) epoxy, (37) nitro, (38) cyano, (39) mercapto, (40) sulfo, (41) sulfino, (42) phosphono, (43) dihydroxypolyol, (44) sulfamoyl, (45) mono-C.sub.1-6 alkylsulfamoyl (46) di-C.sub.1-4 alkylsulfamoyl, (47) C.sub.1-6 alkylthio (48) phenylthio, (49) C.sub.1-6 alkylsulfinyl, (50) phenylsulfinyl, (51) C.sub.1-6 alkylsulfonyl and (52) phenylsulfonyl, and wherein the hydrocarbon group, 5- to 8-membered heterocyclic group and condensed heterocyclic group may be bound through a hetero-atom selected from the group consisting of a nitrogen atom of an amino, C.sub.1-4 alkylamino, hydroxyamino or hydrazino group, a sulfur atom of a thiocarbonyl or sulfino group and an oxygen atom,R.sup.1 and R.sup.2 or R.sup.5 and R.sup.6 when taken together can form a chemical bond;provided that where ring A is a phenyl group having at least a halogen atom in position 2 or 4 and X is an oxygen atom, then R.sup.5 and R.sup.6 do not bind together to form a chemical bond.