WE CLAIM:
[Claim 1]
An antitumor agent comprising a compound represented by the following formula [1] or a salt thereof: [Formula 1]
wherein R1 represents a hydrogen atom or an optionally substituted Ci-6 alkyl group;
R2 represents a hydrogen atom, a halogen atom, or an optionally substituted Ci-6 alkyl group;
R3 represents a halogen atom, an optionally substituted Ci-6 alkyl group, an optionally substituted C2-6 alkenyl group, an optionally substituted C3-8 cycloalkyl group, an optionally substituted C4-8 cycloalkenyl group, an optionally substituted aryl group, an optionally substituted Ci-6 alkoxy group, an optionally substituted Ci-6 alkylamino group, an optionally substituted di(Ci-6 alkyl)amino group, or an optionally substituted heterocyclic group; Z1, Z2 and Z3, which are the same or different, each represent a nitrogen atom or a group represented by the formula CR5 (wherein R5 represents a hydrogen atom, a halogen atom or an optionally substituted Ci-6 alkyl group); X1 represents
(1) a group represented by the formula C(=0)N(R6) (wherein the carbon atom binds to Ring A, and R6 represents a hydrogen atom, an amino-protecting group, or an optionally substituted Ci-6 alkyl group),
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(2) a group represented by the formula N(R7)C(=0) (wherein the nitrogen atom binds to Ring A, and R7 represents a hydrogen atom, an amino-protecting group, or an optionally substituted Ci-6 alkyl group; or R7 represents, together with one substituent R4 of Ring A, an optionally substituted C2-4 alkylene group, a group represented by the formula O-Y1 (wherein the oxygen atom binds to Ring A, and Y1 represents an optionally substituted C1-3 alkylene group), a group represented by the formula S(0)n-Y2 (wherein the sulfur atom binds to Ring A, Y2 represents an optionally substituted C1-3 alkylene group, and n represents an integer from 0 to 2), or a group represented by the formula N(R8)-Y3 (wherein the nitrogen atom binds to Ring A, Y3 represents an optionally substituted C1.3 alkylene group, and R8 represents a hydrogen atom, an amino-protecting group, an optionally substituted C1-6 alkyl group, or an optionally substituted aryl group)),
(3) an optionally substituted divalent cyclic hydrocarbon group that is formed by removing each one hydrogen atom on the two adjacent atoms, or
(4) an optionally substituted divalent heterocyclic group that is formed by removing each one hydrogen atom on the two adjacent atoms;
Ring A represents a cyclic hydrocarbon group or a heterocyclic group; an m number of R4, which are the same or different, each represent a halogen atom, a cyano group, a nitro group, an amino-protecting group, an optionally substituted C1-6 alkyl group, an optionally substituted C2-6 alkenyl group, an optionally substituted C2-6 alkynyl group, an optionally substituted C3-8 cycloalkyl group, an optionally substituted C4-8 cycloalkenyl group, an optionally substituted aryl group, an optionally substituted C1-6 alkoxy group, an optionally substituted aryloxy group, an optionally substituted C1-6 alkylamino group, an optionally substituted di(Ci-6 alkyl)amino group, an optionally substituted arylamino group, an optionally substituted carbamoyl group, an optionally substituted sulfamoyl group, an optionally substituted C1-6 alkylthio group, an optionally substituted arylthio group, an optionally substituted C1-6
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alkylsulfonyl group, an optionally substituted arylsulfonyl group, an optionally
substituted heterocyclic group, an optionally protected amino group, an
optionally protected hydroxyl group, an optionally protected carboxyl group,
an optionally substituted C2-5 alkylene group formed together by the two
adjacent R4,
an optionally substituted C2-4 alkylene group formed by one R4 together with R7,
a group represented by the formula O-Y1 (wherein the oxygen atom binds to
Ring A, and Y1 represents an optionally substituted C1-3 alkylene group), which
is formed by one R4 together with R7,
a group represented by the formula S(0)n-Y2 (wherein the sulfur atom binds to
Ring A, Y2 represents an optionally substituted C1-3 alkylene group, and n
represents an integer from 0 to 2), which is formed by one R4 together with R7,
or
a group represented by the formula N(R8)-Y3 (wherein the nitrogen atom binds
to Ring A, Y3 represents an optionally substituted C1-3 alkylene group, and R8
represents a hydrogen atom, an amino-protecting group, an optionally
substituted C1-6 alkyl group, or an optionally substituted aryl group), which is
formed by one R4 together with R7; and
m represents an integer from 0 to 5.
[Claim 2]
The antitumor agent according to claim 1, wherein R2 represents a hydrogen atom or a C1-6 alkyl group; and Z1, Z2 and Z3 each represent CH.
[Claim 3]
The antitumor agent according to claim 1 or 2, wherein R3 represents an optionally substituted C3-8 cycloalkyl group or an optionally substituted heterocyclic group.
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[Claim 4]
The antitumor agent according to any one of claims 1 to 3, wherein R3 represents any one of the following heterocyclic groups: [Formula 2]
wherein R represents a hydrogen atom, an amino-protecting group, or an optionally substituted Ci-6 alkyl group, and * represents a binding site.
[Claim 5]
The antitumor agent according to any one of claims 1 to 4, wherein Ring A represents a cyclic hydrocarbon group.
[Claim 6]
The antitumor agent according to any one of claims 1 to 5, wherein X1 represents
(2) a group represented by the formula N(R7)C(=0) (wherein the nitrogen atom binds to Ring A, and R7 represents a hydrogen atom, an amino-protecting group, or an optionally substituted Ci-6 alkyl group; or R7 represents, together with one substituent R4 of Ring A, an optionally substituted C2-4 alkylene group, a group represented by the formula O-Y1 (wherein the oxygen atom binds to Ring A, and Y1 represents an optionally substituted C1-3 alkylene group), a group represented by the formula S(0)n-Y2 (wherein the sulfur atom binds to Ring A, Y2 represents an optionally substituted C1-3 alkylene group, and n represents an integer from 0 to 2), or a group represented by the formula N(R8)-Y3 (wherein the nitrogen atom binds to Ring A, Y3
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represents an optionally substituted C1-3 alkylene group, and R8 represents a hydrogen atom, an amino-protecting group, an optionally substituted C1-6 alkyl group, or an optionally substituted aryl group)), or
(4) an optionally substituted divalent heterocyclic group that is formed by removing each one hydrogen atom on the two adjacent atoms.
[Claim 7]
The antitumor agent according to any one of claims 1 to 5, wherein the compound is represented by the following formula [1-1]:
[Formula 3]
wherein R1 represents a hydrogen atom or an optionally substituted C1-6 alkyl group;
R3a represents an optionally substituted C1-6 alkyl group, an optionally substituted C3-8 cycloalkyl group, or an optionally substituted heterocyclic group;
Ring A1 represents a cyclic hydrocarbon group;
R7a represents an amino-protecting group or an optionally substituted C1-6 alkyl group; or
R7a represents, together with one substituent R4a of Ring A1, an optionally substituted C2-3 alkylene group, a group represented by the formula 0-Yla (wherein the oxygen atom binds to Ring A1, and Yla represents an optionally substituted C1-3 alkylene group), a group represented by the formula S(0)n-Y2a (wherein the sulfur atom binds to Ring A1, Y2a represents an optionally
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substituted C1-3 alkylene group, and n represents an integer from 0 to 2), or a
group represented by the formula N(R8a)-Y3a (wherein the nitrogen atom binds
to Ring A1, Y3a represents an optionally substituted C1-3 alkylene group, and R8a
represents a hydrogen atom or an optionally substituted C1-6 alkyl group),
an m1 number of R4a, which are the same or different, each represent a halogen
atom, a cyano group, an optionally substituted C1-3 alkyl group, an optionally
substituted carbamoyl group, an optionally substituted C1-3 alkylsulfonyl group,
an optionally protected carboxyl group,
an optionally substituted C2-5 alkylene group formed together by the two
adjacent R4a,
an optionally substituted C2-3 alkylene group formed by one R4a together with
R7a,
a group represented by the formula 0-Yla (wherein the oxygen atom binds to
Ring A1, and Yla represents an optionally substituted C1-3 alkylene group),
which is formed by one R4a together with R7a,
a group represented by the formula S(0)n-Y2a (wherein the sulfur atom binds to
Ring A1, Y2a represents an optionally substituted C1-3 alkylene group, and n
represents an integer from 0 to 2), which is formed by one R4a together with R7a,
or
a group represented by the formula N(R8a)-Y3a (wherein the nitrogen atom binds
to Ring A1, Y3a represents an optionally substituted C1-3 alkylene group, and R8a
represents a hydrogen atom or an optionally substituted C1-6 alkyl group), which
is formed by one R4a together with R7a; and
m1 represents an integer from 0 to 2.
[Claim 8]
The antitumor agent according to any one of claims 1 to 6, wherein X1 represents an optionally substituted dihydrooxoimidazole-l,5-diyl group, an optionally substituted imidazole-1,2-diyl group, an optionally substituted
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imidazole-4,5-diyl group, an optionally substituted l,2,4-triazole-l,5-diyl group,
an optionally substituted lH-pyrazole-4,5-dihyl group, an optionally substituted
oxopyrrolidine-l,2-diyl group, an optionally substituted
dioxotriazolidine-l,2-diyl group, an optionally substituted
dioxopyrazolidine-l,2-diyl group, an optionally substituted
oxopyrazoline-l,2-diyl group, an optionally substituted pyridine-2,3-diyl group, or an optionally substituted pyrazine-2,3-diyl group.
[Claim 9]
The antitumor agent according to any one of claims 1 to 5, wherein
the compound is represented by the formula [1-2]: [Formula 4]
wherein R1 represents a hydrogen atom or an optionally substituted Ci-6 alkyl group;
R3b represents an optionally substituted Ci-6 alkyl group, an optionally substituted C3-8 cycloalkyl group, or an optionally substituted heterocyclic group;
Xlb represents an optionally substituted dihydrooxoimidazole-l,5-diyl group; Ring A2 represents a cyclic hydrocarbon group;
an m2 number of R4b, which are the same or different, each represent a halogen atom or an optionally substituted Ci-6 alkyl group; and m2 represents an integer from 0 to 2.
[Claim 10]
The antitumor agent according to claim 1, wherein
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the compound is at least one selected from the group consisting of: N-(4-cyclopropyl-1 -ethyl-2-oxo-1,2-dihydroquinolin-6-yl)-N-methylbenzamide, 1 -ethyl-4-(l -ethylpiperidin-4-yl)-N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoli ne-6-carboxamide,
6-(3,4-dihydroquinolin-l(2H)-ylcarbonyl)-l-ethyl-4-(l-methylpiperidin-4-yl)qu inolin-2(lH)-one,
l-ethyl-N-methyl-N-(4-methylphenyl)-4-(l-methylpiperidin-4-yl)-2-oxo-l,2-dih ydroquinoline-6-carboxamide,
N-(2,3-dihydro-lH-inden-5-yl)-l-ethyl-N-methyl-4-(l-methylpiperidin-4-yl)-2-oxo-l,2-dihydroquinoline-6-carboxamide,
6-(5-(4-chlorophenyl)-2-oxo-2,3-dihydro-lH-imidazol-l-yl)-l-ethyl-4-(morphol in-4-yl)quinolin-2(lH)-one,
6-(5-(4-chlorophenyl)-3-methyl-2-oxo-2,3-dihydro-lH-imidazol-l-yl)-l-ethyl-4 -(morpholin-4-yl)quinolin-2(lH)-one,
l-ethyl-4-(morpholin-4-yl)-6-(2-oxo-5-phenyl-3-(propan-2-yl)-2,3-dihydro-lH-imidazol-l-yl)quinolin-2(lH)-one,
l-(4-cyclopropyl-l-ethyl-2-oxo-l,2-dihydroquinolin-6-yl)-2-phenyl-l,2,4-triazo lidine-3,5-dione,
4-chloro-N-(l-ethyl-4-(morpholin-4-yl)-2-oxo-l,2-dihydroquinolin-6-yl)-N-met hylbenzamide,
4-( 1 -acetylpiperidin-4-yl)-1 -ethyl-N-methyl-N-(4-methylphenyl)-2-oxo-1,2-dih ydroquinoline-6-carboxamide,
l-ethyl-N-(3-fluoro-4-methylphenyl)-N-methyl-4-(l-methylpiperidin-4-yl)-2-ox o-1,2-dihydroquinoline-6-carboxamide,
N-(3-chloro-4-methylphenyl)-l-ethyl-N-methyl-4-(l-methylpiperidin-4-yl)-2-o
xo-l,2-dihydroquinoline-6-carboxamide, and
N-(3,4-dimethylphenyl)-l-ethyl-N-methyl-4-(l-methylpiperidin-4-yl)-2-oxo-l,2 -dihydroquinoline-6-carboxamide.
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[Claim 11]
The antitumor agent according to any one of claims 1 to 10, wherein the tumor is blood cancer, thymoma, myeloma, liver cancer, pancreatic
cancer, ovarian cancer, prostate cancer, lung cancer, osteosarcoma, colon cancer,
breast cancer, skin cancer, or epithelial cell cancer.
[Claim 12]
A bromodomain inhibitor, comprising a compound represented by the formula [1] or a salt thereof: [Formula 5]
wherein R1 represents a hydrogen atom or an optionally substituted Ci-6 alkyl group;
R2 represents a hydrogen atom, a halogen atom, or an optionally substituted Ci-6 alkyl group;
R3 represents a halogen atom, an optionally substituted Ci-6 alkyl group, an optionally substituted C2-6 alkenyl group, an optionally substituted C3-8 cycloalkyl group, an optionally substituted C4-8 cycloalkenyl group, an optionally substituted aryl group, an optionally substituted Ci-6 alkoxy group, an optionally substituted Ci-6 alkylamino group, an optionally substituted di(Ci-6 alkyl)amino group, or an optionally substituted heterocyclic group; Z1, Z2 and Z3, which are the same or different, each represent a nitrogen atom or a group represented by the formula CR5 (wherein R5 represents a hydrogen atom,
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a halogen atom or an optionally substituted Ci-6 alkyl group); X1 represents
(1) a group represented by the formula C(=0)N(R6) (wherein the carbon
atom binds to Ring A, and R6 represents a hydrogen atom, an amino-protecting
group, or an optionally substituted Ci-6 alkyl group,
(2) a group represented by the formula N(R7)C(=0) (wherein the nitrogen atom binds to Ring A, and R7 represents a hydrogen atom, an amino-protecting group, or an optionally substituted Ci-6 alkyl group; or R7 represents, together with one substituent R4 of Ring A, an optionally substituted C2-4 alkylene group, a group represented by the formula O-Y1 (wherein the oxygen atom binds to Ring A, and Y1 represents an optionally substituted C1-3 alkylene group), a group represented by the formula S(0)n-Y2 (wherein the sulfur atom binds to Ring A, Y2 represents an optionally substituted C1-3 alkylene group, and n represents an integer from 0 to 2), or a group represented by the formula N(R8)-Y3 (wherein the nitrogen atom binds to Ring A, Y3 represents an optionally substituted C1-3 alkylene group, and R8 represents a hydrogen atom, an amino-protecting group, an optionally substituted Ci-6 alkyl group, or an optionally substituted aryl group)),
(3) an optionally substituted divalent cyclic hydrocarbon group that is formed by removing each one hydrogen atom on the two adjacent atoms, or
(4) an optionally substituted divalent heterocyclic group that is formed by removing each one hydrogen atom on the two adjacent atoms;
Ring A represents a cyclic hydrocarbon group or a heterocyclic group; an m number of R4, which are the same or different, each represent a halogen atom, a cyano group, a nitro group, an amino-protecting group, an optionally substituted Ci-6 alkyl group, an optionally substituted C2-6 alkenyl group, an optionally substituted C2-6 alkynyl group, an optionally substituted C3-8 cycloalkyl group, an optionally substituted C4-8 cycloalkenyl group, an optionally substituted aryl group, an optionally substituted Ci-6 alkoxy group, an
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optionally substituted aryloxy group, an optionally substituted Ci-6 alkylamino group, an optionally substituted di(Ci-6 alkyl)amino group, an optionally substituted arylamino group, an optionally substituted carbamoyl group, an optionally substituted sulfamoyl group, an optionally substituted Ci-6 alkylthio group, an optionally substituted arylthio group, an optionally substituted Ci-6 alkylsulfonyl group, an optionally substituted arylsulfonyl group, an optionally substituted heterocyclic group, an optionally protected amino group, an optionally protected hydroxyl group, an optionally protected carboxyl group, an optionally substituted C2-5 alkylene group formed together by the two adjacent R4,
an optionally substituted C2-4 alkylene group formed by one R4 together with R7, a group represented by the formula O-Y1 (wherein the oxygen atom binds to Ring A, and Y1 represents an optionally substituted C1-3 alkylene group), which is formed by one R4 together with R7,
a group represented by the formula S(0)n-Y2 (wherein the sulfur atom binds to Ring A, Y2 represents an optionally substituted C1-3 alkylene group, and n represents an integer from 0 to 2), which is formed by one R4 together with R7, or
a group represented by the formula N(R8)-Y3 (wherein the nitrogen atom binds to Ring A, Y3 represents an optionally substituted C1-3 alkylene group, and R8 represents a hydrogen atom, an amino-protecting group, an optionally substituted Ci-6 alkyl group, or an optionally substituted aryl group), which is formed by one R4 together with R7; and m represents an integer from 0 to 5.
[Claim 13]
The bromodomain inhibitor according to claim 12, which inhibits the binding of bromodomain to acetylated histone.
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[Claim 14]
The bromodomain inhibitor according to claim 12 or 13, wherein the bromodomain is a protein domain comprised in a BET family protein.
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