Claims
- 1. A compound of the formula: wherein the ring A is a basic 5- to 7-membered heterocyclic group which may be substituted; the ring B is a divalent 5- to 7-membered nitrogen containing heterocyclic group which may be substituted or a divalent 5- to 7-membered cyclic hydrocarbon group which may be substituted; Y is an optionally substituted methylene group; R1 is a hydrogen atom, an optionally substituted hydroxy group, an optionally substituted amino group or an optionally substituted hydrocarbon group which may be bound through a carbonyl group, a thio group, a sulfinyl group or a sulfonyl group; R2 is a hydrogen atom or an optionally substituted hydrocarbon group; R3 is an optionally esterified or amidated carboxyl group; and D is a lower alkyl group substituted with an optionally esterified carboxyl group; or a salt thereof.
- 2. A compound according to claim 1, wherein the ring A is a basic 5- to 7-membered heterocyclic group containing, besides carbon atoms, 1 to 3 hetero-atoms selected from oxygen atom, sulfur atom and nitrogen atom, which may have 1 to 5 substituents selected from the class consisting of (1) a C1-6 alkyl group, (2) a C2-6 alkenyl group, (3) a C2-6 alkynyl group, (4) a C3-8 cycloalkyl group, (5) a C3-8 cycloalkenyl group, (6) a C7-12 aralkyl group, (7) a C6-10 aryl group, (8) a C1-6 alkoxy group, (9) a phenoxy group, (10) a C1-6 alkanoyl group, (11) a benzoyl group, (12) a C1-6 alkanoyloxy group, a benzoyloxy group, (13) a carboxyl group, (14) a C1-6 alkoxy-carbonyl group, (15) a carbamoyl group, (16) a N-mono-C1-6 alkyl-carbamoyl group, (17) a N,N-di-C1-6 alkyl-carbamoyl group, (18) a cyclic amino-carbonyl group, (19) a halogen atom, (20) a halogeno C1-6 alkyl group, (21) an oxo group, (22) an amidino group, (23) an imino group, (24) an amino group, (25) a mono-C1-6 alkylamino group, (26) a di-C1-6 alkylamino group, (27) a 3- to 6-membered cyclic amino group, (28) a C1-6 alkanoylamido group, (29) a benzamido group, (30) a carbamoylamino group, (31) a N-mono-C1-6 alkyl-carbamoylamino group, (32) a N,N-di-C1-6 alkyl-carbamoylamino group, (33) a C1-3 alkylenedioxy group, (34) a sulfamoyl group, (35) a C1-6 alkylsulfamoyl group, (36) a di-C1-6 alkylsulfamoyl group, (37) a C1-6 alkylthio group, (38) a C6-10 arylthio group, (39) a C1-6 alkylsulfinyl group, (40) a C6-10 arylsulfinyl group, (41) a C1-6 alkylsulfonyl group and (42) a C6-10 arylsulfonyl group;the ring B is (A) a divalent 5- to 7-membered nitrogen containing heterocyclic group which contains, besides carbon atoms, 1 to 3 nitrogen atoms and which may have 1 to 5 substituents selected from the class consisting of (1) a C1-6 alkyl group, (2) a C2-6 alkenyl group, (3) a C2-6 alkynyl group, (4) a C3-8 cycloalkyl group, (5) a C3-8 cycloalkenyl group, (6) a C7-12 aralkyl group, (7) a C6-10 aryl group, (8) a C1-6 alkoxy group, (9) a phenoxy group, (10) a C1-6 alkanoyl group, (11) a benzoyl group, (12) a C1-6 alkanoyloxy group, a benzoyloxy group, (13) a carboxyl group, (14) a C1-6 alkoxy-carbonyl group, (15) a carbamoyl group, (16) a N-mono-C1-6 alkyl-carbamoyl group, (17) a N,N-di-C1-6 alkyl-carbamoyl group, (18) a cyclic amino-carbonyl group, (19) a halogen atom, (20) a halogeno C1-6 alkyl group, (21) an oxo group, (22) an amidino group, (23) an imino group, (24) an amino group, (25) a mono-C1-6 alkylamino group, (26) a di-C1-6 alkylamino group, (27) a 3- to 6-membered cyclic amino group, (28) a C1-6 alkanoylamido group, (29) a benzamido group, (30) a carbamoylamino group, (31) a N-mono-C1-6 alkyl-carbamoylamino group, (32) a N,N-di-C1-6 alkyl-carbamoylamino group, (33) a C1-3 alkylenedioxy group, (34) a sulfamoyl group, (35) a C1-6 alkylsulfamoyl group, (36) a di-C1-6 alkylsulfamoyl group, (37) a C1-6 alkylthio group, (38) a C6-10 arylthio group, (39) a C1-6 alkylsulfinyl group, (40) a C6-10 arylsulfinyl group, (41) a C1-6 alkyl-sulfonyl group and (42) a C6-10 arylsulfonyl group, or (B) a divalent 5- to 7-membered cyclic hydrocarbon group which may have 1 to 5 substituents selected from the class consisting of (1) a C1-6 alkyl group, (2) a C3-8 cycloalkyl group, (3) a C2-6 alkenyl group, (4) a C2-6 alkynyl group, (5) a C3-8 cycloalkenyl group, (6) a C6-10 aryl group, (7) a C7-12 aralkyl group, (8) a nitro group, (9) an oxo group, (10) a thioxo group, (11) a cyano group, (12) a carbamoyl group, (13) a carboxyl group, (14) a C1-6 alkoxy-carbonyl group, (15) a sulfo group, (16) a halogen atom, (17) a C1-4 alkoxy group, (19) a C6-10 aryloxy group, (20) a C1-4 alkylthio group, (21) a C6-10 arylthio group, (22) a C1-6 alkylsulfinyl group, (23) a C6-10 arylsulfinyl group, (24) a C1-6 alkyl-sulfonyl group, (25) a C6-10 arylsulfonyl group, (26) an amino group, (27) a C1-6 alkanoylamino group, benzoylamino, (28) a mono- or di-C1-6 alkylamino group, (29) a C3-8 cyclo-alkylamino group, (30) a C6-10 arylamino group, (31) a C1-6 acyl group, (32) a C6-10 aryl-carbonyl group and (33) 5- to 6-membered heterocyclic groups containing, besides carbon atoms, 1 to 3 hetero-atoms selected from oxygen atom, sulfur atom and nitrogen atom; Y is a methylene group which may have 1 or 2 substituents selected from the class consisting of (1) a halogen atom, (2)ahydroxygroup, (3) anoxogroup, (4) a C1-6 alkoxy group, (5) a di-C1-6 alkylamino group, (6) a C1-6 alkyl group substituted with 1 to 3 halogen atoms, (7) a C1-6 acyl group, (8) a hydroxy-C1-6 alkyl group, (9) a C1-6 alkoxy-C1-6 alkyl group and (10) a C1-6 alkoxy-carbonyl group; R1 is (A) a hydrogen atom, (B) a hydroxy group optionally substituted by (1) a C1-6 alkyl group which may have 1 to 4 substituents selected from the class consisting of a halogen atom, a C6-10 aryl group, a C7-12 aralkyl group and a nitro group, (2) a C6-10 aryl group which may have 1 to 4 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group, a C6-10 aryl group, a C7-12 aralkyl group and a nitro group, (3) a C7-12 aralkyl group which may have 1 to 4 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group, a C6-10 aryl group, a C7-12 aralkyl group and a nitro group, (4) a formyl group, (5) a C1-6 alkyl-carbonyl group which may have 1 to 4 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group, a C6-10 aryl group, a C7-12 aralkyl group and a nitro group, (6) a C6-10 aryloxy-carbonyl group which may have 1 to 4 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group, a C6-10 aryl group, a C7-12 aralkyl group and a nitro group, (7) a C6-10 aryl-carbonyl group which may have 1 to 4 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group, a C6-10 aryl group, a C7-12 aralkyl group and a nitro group, (8) a 5-membered aromatic heterocyclic group which may have 1 to 4 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group, a C6-10 aryl group, a C7-12 aralkyl group and a nitro group, or (10) a tri-C1-4 alkylsilyl, (C) an amino group which may have 1 or 2 substituents selected from the class consisting of (C-1) an optionally substituted hydrocarbon group selected from the class consisting of (i) a C1-6 alkyl group, (ii) a C3-8 cycloalkyl group, (iii) a C2-6 alkenyl group, (iv) a C2-6 alkynyl group, (v) a C3-8 cycloalkenyl group, (vi) a C6-10 aryl group and (vii) a C7-12 aralkyl group, each of said hydrocarbon group being unsubstituted or substituted by 1 to 4 substituents selected from the class consisting of (1) a nitro group, (2) a hydroxy group, (3) an oxo group, (4) a thioxo group, (5) a cyano group, (6) a carbamoyl group, (7) a carboxyl group, (8) a C1-6 alkoxy-carbonyl group, (9) a halogen atom, (10) a C1-6 alkoxy group, (11) a phenoxy group, (12) a phenoxy group substituted with 1 to 3 halogen atoms, (13) a C1-6 alkylthio group, (14) a phenylthio group, (15) a C1-6 alkylsulfinyl group, (16) a C1-6 alkylsulfonyl group, (17) an amino group, (18) a C1-6 alkanoylamino group, (19) a mono- or di-C1-6 alkylamino group, (20) a C1-6 acyl group, (21) a benzoyl group, (22) a 5- to 6-membered heterocyclic group containing, besides carbon atoms, 1 to 3 hetero-atoms selected from oxygen atom, sulfur atom and nitrogen atom which may have 1 to 4 substituents selected from the class consisting of (a) a halogen atom, (b) a C1-6 alkyl group and (c) a phenoxy group substituted with 1 to 3 halogen atoms, (23) a C1-6 alkyl group substituted with 1 to 3 halogen atoms, (24) a C1-6 alkyl group and (25) a C3-8 cycloalkyl group, and (C-2) an acyl group represented by the formula: R4CO—, R5OCO—, R6SO2— or R7SO—wherein R4, R5, R6 and R7 are independently (C-2-1) an optionally substituted hydrocarbon group selected from the class consisting of (i) a C1-6 alkyl group, (ii) a C3-8 cycloalkyl group, (iii) a C2-6 alkenyl group, (iv) a C2-6 alkynyl group, (v) a C3-8 cycloalkenyl group, (vi) a C6-10 aryl group and (vii) a C7-12 aralkyl group, each of said hydrocarbon group being unsubstituted or substituted by 1 to 4 substituents selected from the class consisting of (1) a nitro group, (2) a hydroxy group, (3) an oxo group, (4) a thioxo group, (5) a cyano group, (6) a carbamoyl group, (7) a carboxyl group, (8) a C1-6 alkoxy-carbonyl group, (9) a halogen atom, (10) a C1-6 alkoxy group, (11) a phenoxy group, (12) a phenoxy group substituted with 1 to 3 halogen atoms, (13) a C1-6 alkylthio group, (14) a phenylthio, (15) a C1-6 alkylsulfinyl group, (16) a C1-6 alkylsulfonyl group, (17) an amino group, (18) a C1-6 alkanoylamino, (19) a mono- or di-C1-6 alkylamino group, (20) a C1-6 acyl group, (21) a benzoyl group, (22) a 5- to 6-membered heterocyclic group containing, besides carbon atoms, 1 to 3 hetero-atoms selected from oxygen atom, sulfur atom and nitrogen atom which may have 1 to 4 substituents selected from the class consisting of (a) a halogen atom, (b) a C1-6 alkyl group and (c) a phenoxy group substituted with 1 to 3 halogen atoms, (23) a C1-6 alkyl group substituted with 1 to 3 halogen atoms, (24) a C1-6 alkyl group and (25) a C3-8 cycloalkyl group, or (C-2-2) a basic 5- to 7-membered heterocyclic group containing, besides carbon atoms, 1 to 3 hetero-atoms selected from oxygen atom, sulfur atom and nitrogen atom, which may have 1 to 5 substituents selected from the class consisting of (1) a C1-6 alkyl group, (2) a C2-6 alkenyl group, (3) a C2-6 alkynyl group, (4) a C3-8 cycloalkyl group, (5) a C3-8 cycloalkenyl group, (6) a C7-12 aralkyl group, (7) a C6-10 aryl group, (8) a C1-6 alkoxy group, (9) a phenoxy group, (10) a C1-6 alkanoyl group, (11) a benzoyl group, (12) a C1-6 alkanoyloxy group, a benzoyloxy group, (13) a carboxyl group, (14) a C1-6 alkoxy-carbonyl group, (15) a carbamoyl group, (16) a N-mono-C1-6 alkyl-carbamoyl group, (17) a N,N-di-C1-6 alkyl-carbamoyl group, (18) a cyclic amino-carbonyl group, (19) a halogen atom, (20) a halogeno C1-6 alkyl group, (21) an oxo group, (22) an amidino group, (23) an imino group, (24) an amino group, (25) a mono-C1-6 alkylamino group, (26) a di-C1-6 alkylamino group, (27) a 3- to 6-membered cyclic amino group, (28) a C1-6 alkanoylamido group, (29) a benzamido group, (30) a carbamoylamino group, (31) a N-mono-C1-6 alkyl-carbamoylamino group, (32) a N,N-di-C1-6 alkyl-carbamoylamino group, (33) a C1-3 alkylenedioxy group, (34) a sulfamoyl group, (35) a C1-6 alkylsulfamoyl group, (36) a di-C1-6 alkylsulfamoyl group, (37) a C1-6 alkylthio group, (38) a C6-10 arylthio group, (39) a C1-6 alkylsulfinyl group, (40) a C6-10 arylsulfinyl group, (41) a C1-6 alkylsulfonyl group and (42) a C6-10 arylsulfonyl group, or (D) a hydrocarbon group which may be bound through a carbonyl group, a thio group, a sulfinyl group or a sulfonyl group, said hydrocarbon group being selected from the class consisting of (i) a C1-6 alkyl group, (ii) a C3-8 cycloalkyl group, (iii) a C2-6 alkenyl group, (iv) a C2-6 alkynyl group, (v) a C3-8 cycloalkenyl group, (vi) a C6-10 aryl group and (vii) a C7-12 aralkyl group, and each of said hydrocarbon group being unsubstituted or substituted by 1 to 4 substituents selected from the class consisting of (1) a nitro group, (2) a hydroxy group, (3) an oxo group, (4) a thioxo group, (5) a cyano group, (6) a carbamoyl group, (7) a carboxyl group, (8) a C1-6 alkoxy-carbonyl group, (9) a halogen atom, (10) a C1-6 alkoxygroup, (11) aphenoxygroup, (12) a phenoxy group substituted with 1 to 3 halogen atoms , (13) a C1-6 alkylthio group, (14) a phenylthio group, (15) a C16 alkylsulfinyl group, (16) a C1-6 alkylsulfonyl group, (17) an amino group, (18) a C1-6 alkanoylamino group, (19) a mono- or di-C1-6 alkylamino group, (20) a C1-6 acyl group, (21) a benzoyl group, (22) a 5- to 6-membered heterocyclic group containing, besides carbon atoms, 1 to 3 hetero-atoms selected from oxygen atom, sulfur atom and nitrogen atom which may have 1 to 4 substituents selected from the class consisting of (a) a halogen atom, (b) a C1-6 alkyl group and (c) a phenoxy group substituted with 1 to 3 halogen atoms, (23) a C1-6 alkyl group substituted with 1 to 3 halogen atoms, (24) a C1-6 alkyl group and (25) a C3-8 cycloalkyl group;R2 is a hydrogen atom or an optionally substituted hydrocarbon group selected from the class consisting of (i) a C1-6 alkyl group, (ii) a C3-8 cycloalkyl group, (iii) a C2-6 alkenyl group, (iv) a C2-6 alkynyl group, (v) a C3-8 cycloalkenyl group, (vi) a C6-10 aryl group and (vii) a C7-12 aralkyl group, each of said hydrocarbon group being unsubstituted or substituted by 1 to 4 substituents selected from the class consisting of (1) a nitro group, (2) a hydroxy group, (3) an oxo group, (4) a thioxo group, (5) a cyano group, (6) a carbamoyl group, (7) a carboxyl group, (8) a C1-6 alkoxy-carbonyl group, (9) a halogen atom, (10) a C1-6 alkoxy group, (11) aphenoxy group, (12) a phenoxy group substituted with 1 to 3 halogen atoms , (13) a C1-6 alkylthio group, (14) a phenylthio group, (15) a C1-6 alkylsulfinyl group, (16) a C1-6 alkylsulfonyl group, (17) an amino group, (18) a C1-6 alkanoylamino group, (19) a mono- or di-C1-6 alkylamino group, (20) a C1-6 acyl group, (21) a benzoyl group, (22) a 5- to 6-membered heterocyclic group containing, besides carbon atoms, 1 to 3 hetero-atoms selected from oxygen atom, sulfur atom and nitrogen atom which may have 1 to 4 substituents selected from the class consisting of (a) a halogen atom, (b) a C1-6 alkyl group and (c) a phenoxy group substituted with 1 to 3 halogen atoms, (23) a C1-6 alkyl group substituted with 1 to 3 halogen atoms, (24) a C1-6 alkyl group and (25) a C3-8 cycloalkyl group; R3 is a group of the formula: wherein R8 is(A) a hydroxy group, (B) a C1-6 alkoxy group optionally substituted with 1 to 3 substituents selected from the class consisting of (1) a hydroxy group, (2) an amino group, (3) a mono-C1-6 alkylamino group, (4) a di-C1-6 alkylaminogroup, (5) a piperidino group, (6) a morpholino group, (7) a halogen atom, (8) a C1-6alkoxy group, (9) a C1-6 alkylthio group, (10) a C1-6 alkoxy-carbonyl group, (11) a propylidene group, (12) a 3-phthalidylidene group and (13) a 5-methyl-2-oxo-1,3-dioxolan-4-yl group, (C) a group of the formula: —OCH(R11)OCOR12 in which R11 is (1) a hydrogen atom, (2) a straight-chain or branched C1-6 alkyl group or (3) a C5-7 cycloalkyl group, and R12 is (1) a straight-chain or branched C1-6 alkyl group, (2) a C2-8 alkenyl group, (3) a C5-7 cycloalkyl group, (4) a C1-3 alkyl group substituted with C5-7 cycloalkyl or C6-10 aryl, said aryl being optionally substituted with 1 to 3 substituents selected from the class consisting of a halogen atom, a nitro group and a C1-6 alkyl group, (5) a C2-3 alkenyl group substituted with C5-7 cycloalkyl or C6-10 aryl, said aryl being optionally substituted with 1 to 3 substituents selected from the class consisting of a halogen atom, a nitro group and a C1-6 alkyl group, (6) a C6-10 aryl group, said aryl being optionally substituted with 1 to 3 substituents selected from the class consisting of a halogen atom, a nitro group and a C1-6 alkyl group, (7) a straight-chain or branched C1-6 alkoxy group, (8) a straight-chain or branched C2-8 alkenyloxy group, (9) a C5-7 cycloalkyloxy group, (10) a C1-3 alkoxy group substituted with C5-7 cycloalkyl or C6-10 aryl, said aryl being optionally substituted with 1 to 3 substituents selected from the class consisting of a halogen atom, a nitro group and a C1-6 alkyl group, (11) a C2-3 alkenyloxy group substituted with C5-7 cycloalkyl or C6-10 aryl, said aryl being optionally substituted with 1 to 3 substituents selected from the class consisting of a halogen atom, a nitro group and a C1-6 alkyl group, or (12) a C6-10 aryloxy group, said aryl being optionally substituted with 1 to 3 substituents selected from the class consisting of a halogen atom, a nitro group and a C1-6 alkyl group, (D) a C2-8 alkenyloxy group, (E) a C7-12 aralkyloxy group, or (F) a group of the formula: —NR9R10 wherein R9 and R10 are the same or different (F-1) a hydrogen atom, (F-2) a C1-6 alkyl group, (F-3) a C2-8 alkenyl group, or (F-4) a C7-12 aralkyl group, the aryl group of which is unsubstituted or substituted with one or two substituents selected from the class consisting of (1) a nitro group, (2) a halogen atom, (3) a C1-6 alkyl group and (4) a C1-6 alkoxy group; and D is a C1-6 alkyl group substituted with a group of the formula: wherein R8′ is(A) a hydroxy group, (B) a C1-6 alkoxy group optionally substituted with 1 to 3 substituents selected from the class consisting of (1) a hydroxy group, (2) an amino group, (3) a mono-C1-6alkylamino group, (4) a di-C1-6 alkylamino group, (5) a piperidino group, (6) a morpholino group, (7) ahalogen atom, (8) a C1-6 alkoxy group, (9) a C1-6 alkylthio group, (10) a C1-6 alkoxy-carbonyl group, (11) a propylidene group, (12) a 3-phthalidylidene group and (13) a 5-methyl-2-oxo-1,3-dioxolan-4-yl group, (C) a group of the formula: —OCH(R11)OCOR12 in which R11 is (1) a hydrogen atom, (2) a straight-chain or branched C1-6 alkyl group or (3) a C5-7 cycloalkyl group, and R12 is (1) a straight-chain or branched C1-6 alkyl group, (2) a C2-8 alkenyl group, (3) a C5-7 cycloalkyl group, (4) a C1-3 alkyl group substituted with C5-7 cycloalkyl or C6-10 aryl, said aryl being optionally substituted with 1 to 3 substituents selected from the class consisting of a halogen atom, a nitro group and a C1-6 alkyl group, (5) a C2-3 alkenyl group substituted with C5-7 cycloalkyl or C6-10 aryl, said aryl being optionally substituted with 1 to 3 substituents selected from the class consisting of a halogen atom, a nitro group and a C1-5 alkyl group, (6) a C6-10 aryl group, said aryl being optionally substituted with 1 to 3 substituents selected from the class consisting of a halogen atom, a nitro group and a C1-6 alkyl group, (7) a straight-chain or branched C1-6 alkoxy group, (8) a straight-chain or branched C2-8 alkenyloxy group, (9) a C5-7 cycloalkyloxy group, (10) a C1-3 alkoxy group substituted with C5-7 cycloalkyl or C6-10 aryl, said aryl being optionally substituted with 1 to 3 substituents selected from the class consisting of a halogen atom, a nitro group and a C1-6 alkyl group, (11) a C2-3 alkenyloxy group substituted with C5-7 cycloalkyl or C6-10 aryl, said aryl being optionally substituted with 1 to 3 substituents selected from the class consisting of a halogen atom, a nitro group and a C1-6 alkyl group, or (12) a C6-10 aryloxy group, said aryl being optionally substituted with 1 to 3 substituents selected from the class consisting of a halogen atom, a nitro group and a C1-6 alkyl group, (D) a C2-8 alkenyloxy group, or (E) a C7-12 aralkyloxy group.
- 3. A compound according to claim 1, wherein the ring A is a basic 6-membered heterocyclic group which may be substituted and which contains 1 to 2 nitrogen atoms.
- 4. A compound according to claim 5, wherein the basic 6-membered heterocyclic group is pyridyl, pyrimidinyl or piperidyl.
- 5. A compound according to claim 3, wherein the basic 6-membered heterocyclic group is piperidyl.
- 6. A compound according to claim 3, wherein the basic 6-membered heterocyclic group is pyridyl.
- 7. A compound according to claim 2, wherein the ring A1 is pyridyl.
- 8. A compound according to claim 1, wherein the ring B is a divalent 6-membered nitrogen containing heterocyclic group which contains 1 or 2 nitrogen atoms and which may be substituted or a phenylene group which may be substituted.
- 9. A compound according to claim 1, wherein the ring B is phenylene, piperidinedjyl or piperazinediyl, each of which may be substituted.
- 10. A compound according to claim 1, wherein the ring B is phenylene which may be substituted.
- 11. A compound according to claim 1, wherein the ring B is piperazinediyl which may be substituted.
- 12. A compound according to claim 1, wherein R1 is a hydrogen atom, an optionally substituted hydroxy group, an optionally substituted lower alkyl group or an optionally substituted amino group.
- 13. A compound according to claim 1, wherein R1 is a hydroxy group optionally substituted with a C1-6 alkyl-carbonyl group.
- 14. A compound according to claim 1, wherein R1 is an optionally substituted amino group selected from the class consisting of (1) an amino group optionally substituted with a C1-6 acyl group, (2) a mono-C1-6 alkylamino group, (3) a di-C1-6 alkylamino group, (4) a C1-6 alkoxy-carbonylamino group, (5) a C1-6 alkylthio-carbonylamino group, (6) a C7-12 aralkylamino group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-5 alkoxy group, (7) a benzoylamino group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group, (8) a benzene-sulfonylamino group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group, and (9) a C1-6 alkoxy-carbonylamino group which may be substituted with C1-6 alkanoyloxy, benzoyloxy, C1-6 alkoxy-carbonyloxy, C3-8 cycloalkyl-oxycarbonyloxy, C3-8 cycloalkyl-carbonyloxy, 6-membered aromatic heterocyclic group-carbonyloxy or 5-methyl-2-oxo-1,3-dioxolan-4-yl.
- 15. A compound according to claim 1, wherein R1 is an optionally substituted hydrocarbon group which may be bound through a carbonyl group, a thio group, a sulfinyl group or a sulfonyl group, being selected from the class consisting of (1) a C1-6 alkyl-carbonyl group, (2) a C1-6 alkylthio group, (3) a C1-6 alkylsulf inyl group, (4) a C1-6 alkylsulfonyl group, (5) a benzoyl group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group, (6) a phenylthio group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group, a C1-6 alkoxy group, (7) a phenylsulfinyl group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group, (8) a phenylsulfonyl group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group, (9) a C7-12 aralkyl-carbonyl group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group, (10) a C7-12 aralkylthio group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group, (11) a C7-12 aralkyl-sulfinyl group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group, (12) a C7-12 aralkyl-sulfonyl group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group, and (13) a C1-6 alkyl group optionally substituted with a C1-6 aryl group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group.
- 16. A compound according to claim 1, wherein R2 is a hydrogen atom.
- 17. A compound according to claim 1, wherein R3 is a carboxyl group or a C1-6 alkoxy-carbonyl group.
- 18. A compound according to claim 1, wherein R3 is methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, propoxycarbonyl, pivaloyloxymethoxycarbonyl, 1-(cyclohexyloxycarbonyloxy)ethoxycarbonyl, 5-methyl-2-oxo-1,3-dioxolan-4-ylmethoxycarbonyl, acetoxymethyloxycarbonyl, propionyloxymethoxycarbonyl, n-butyryloxymethoxycarbonyl, isobutyryloxymethoxycarbonyl, 1-(ethoxycarbonyloxy)ethoxycarbonyl, 1-(acetyloxy)ethyloxycarbonyl, 1-(isobutyryloxy)ethoxycarbonyl, cyclohexylcarbonyloxymethoxycarbonyl, benzoyloxymethoxycarbonyl, cinnamyloxycarbonyl, cyclopentylcarbonyloxy-methoxycarbonyl, N,N-dimethylaminocarbonyl, 2-(iso-butyryloxycarbonyl)-2-propylideneethoxycarbonyl or 3-(phthalidylidene)ethoxycarbonyl.
- 19. A compound according to claim 1, wherein D is a C1-6 alkoxy-carbonyl-C1-6 alkyl group.
- 20. A compound according to claim 1, wherein the ring A is pyridyl, pyrimidinyl or piperidyl; the ring B is phenylene, piperidinediyl or piperazinediyl; Y is a methylene group; R1 is (A) a hydrogen atom, (B) a hydroxy group optionally substituted with a C1-6 alkyl-carbonyl group, (C) an amino group optionally substituted with one or two substituents selected from the class consisting of (1) a formyl group, (2) a C26 alkanoyl group, (3) a C1-6 alkyl group, (4) a C1-6 alkoxy-carbonyl group, (5) a C1-6 alkylthio-carbonyl group, (6) a C7-12 aralkyl group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group, (7) a benzoyl group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group, (8) a benzenesulfonyl group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group, and (9) a C1-6 alkoxy-carbonyl group which may be substituted with C1-6 alkanoyloxy, benzoyloxy, C1-6 alkoxy-carbonyloxy, C3-8 cycloalkyloxy-carbonyloxy, C3-8 cycloalkyl-carbonyloxy, pyridyl-carbonyloxy or 5-methyl-2-oxo-1,3-dioxolan-4-yl, or (D) a C1-6 alkyl group optionally substituted with a C6-10 aryl group which may have 1 to 3 substituents selected from the class consisting of a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group; R2 is a hydrogen atom; R3 is a carboxyl group or a C1-6 alkoxy-carbonyl group; and D is a C1-6 alkoxy-carbonyl-C1-6 alkyl group.
- 21. A compound of claim 1, which is (S,S)-[4-[2-(4-methoxybenzenesulfonylamino)-4-oxo-(4-pyridin-4-yl-piperazin-1-yl)butyryl]-3-methoxycarbonylmethyl-2-oxo-piperazin-1-yl]acetic acid, (S,S)-[4-[2-(4-methoxy-benzylamino)-4-oxo-(4-pyridin-4-ylpiperazin-1-yl)-butyryl]-3-methoxycarbonylmethyl-2-oxopiperazin-1-yl]-acetic acid, or a pharmaceutically acceptable salt thereof.
- 22. A pharmaceutical composition which comprises a compound or a salt thereof according to any one of claims 1-3.
- 23. A pharmaceutical composition for inhibiting cell-adhesion which comprises a compound or a salt thereof according to claim 1.
- 24. A pharmaceutical composition for treating or preventing angina pectoris, which comprises a compound or a salt thereof according to claim 1 in admixture with a pharmaceutically acceptable carrier or excipient.
- 25. A pharmaceutical composition for treating or preventing unstable angina, which comprises a compound or a salt thereof according to claim 1 in admixture with a pharmaceutically acceptable carrier or excipient.
- 26. A pharmaceutical composition for treating or preventing ischemic complication, reobstruction or restenosis after percutaneous transluminal coronary angioplasty or coronary thrombolytic therapy, which comprises a compound or a salt thereof according to claim 1, in admixture with a pharmaceutically acceptable carrier or excipient.
- 27. A method of using a compound or a salt thereof according to any claim 1 for manufacturing a pharmaceutical omposition.
- 28. A method of using a compound or a salt thereof according to claim 1 for manufacturing a pharmaceutical composition for inhibiting cell-adhesion.
- 29. A method of using a compound or a salt thereof according to claim 1 for manufacturing a pharmaceutical composition for treating or preventing angina pectoris.
- 30. A method of using a compound or a salt thereof according to claim 1 for manufacturing a pharmaceutical composition for treating or preventing unstable angina.
- 31. A method of using a compound or a salt thereof according to claim 1 for manufacturing a pharmaceutical composition for treating or preventing ischemic complication, reobstruction or restenosis after percutaneous transluminal coronary angioplasty or coronary thrombolytic therapy.
- 32. A method for inhibiting cell-adhesion in a mammal which comprises administering an effective amount of a compound or a salt thereof according to of claim 1 to said mammal.
- 33. A method for preventing or treating angina pectoris, in a mammal which comprises administering an effective amount of a compound or a salt thereof according to any one of claim 1 to said mammal.
- 34. A method for preventing or treating unstable angina in a mammal which comprises administering an effective amount of a compound or a salt thereof according to claim 1 to said mammal.
- 35. A method for preventing or treating ischemic complication, reobstruction or restenosis after percutaneous transluminal coronary angioplasty or coronary thrombolytic therapy in a mammal which comprises administering an effective amount of a compound or a salt thereof according to claim 1 to said mammal.
- 36. A method for producing a compound of the formula: wherein the ring A is a basic 5- to 7-membered heterocyclic group which may be substituted; the ring B is a divalent 5- to 7-membered nitrogen containing heterocyclic group which may be substituted or a divalent 5- to 7-membered cyclic hydrocarbon group which may be substituted; Y is an optionally substituted methylene group; R1 is a hydrogen atom, an optionally substituted hydroxy group, an optionally substituted amino group or an optionally substituted hydrocarbon group which may be bound through a carbonyl group, a thio group, a sulfinyl group or a sulfonyl group; R2 is a hydrogen atom or an optionally substituted hydrocarbon group; R3 is an optionally esterified or amidated carboxyl group; and D is a lower alkyl group substituted with an optionally esterified carboxyl group; or a salt thereof, which comprises subjecting a compound (II) of the formula: wherein each symbol is of the same meaning as defined above, or a salt thereof and a compound (III) of the formula: wherein each symbol is of the same meaning as defined above, or a salt thereof to condensation reaction.
- 37. A method for producing a compound of the formula: wherein the ring A is a basic 5- to 7-membered heterocyclic group which may be substituted; the ring B′ is an optionally substituted piperazinediyl group; Y is an optionally substituted methylene group; R1 is a hydrogen atom, an optionally substituted hydroxy group, an optionally substituted amino group or an optionally substituted hydrocarbon group which may be bound through a carbonyl group, a thio group, a sulfinyl group or a sulfonyl group; R2 is a hydrogen atom or an optionally substituted hydrocarbon group; R3 is an optionally esterified or amidated carboxyl group; and D is a lower alkyl group substituted with an optionally esterified carboxyl group; or a salt thereof, which comprises subjecting a compound (VI) of the formula: wherein B′ is an optionally substituted piperazinediyl group and the other symbols are of the same meaning as defined above, or a salt thereof and a compound (VII) of the formula: wherein each symbol is of the same meaning as defined above, or a salt thereof to condensation reaction.
- 38. A compound of claim 1, which is (R,S)-(4-[2-Amino-4-oxo-4-(4-pyridin-4-ylpiperazin-1-yl)butyryl]-3-methoxycarbonylmethyl-2-oxopiperazin-1-yl)acetic acid trifluoroacetic acid salt.
Priority Claims (1)
Number |
Date |
Country |
Kind |
9-053574 |
Mar 1997 |
JP |
|
Parent Case Info
This application is the National Stage of International Patent application PCT/JP98/00688, filed Feb. 19, 1998.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/JP98/00907 |
|
WO |
00 |
7/28/1999 |
7/28/1999 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO98/39324 |
9/11/1998 |
WO |
A |
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5876756 |
Takada et al. |
Mar 1999 |
|
Foreign Referenced Citations (4)
Number |
Date |
Country |
0529858 |
Mar 1993 |
EP |
0643072 |
Mar 1995 |
EP |
0765660 |
Apr 1997 |
EP |
WO 9633982 |
Oct 1996 |
WO |