Pyridazinone compounds
The present invention provides a compound which has the effect of PDE inhibition, and which is useful as a medicament for preventing or treating schizophrenia or so on. A compound of formula (I 0 ), wherein R1 represents a substituent; R2 represents a hydrogen atom, or a substituent; R3 represents a hydrogen atom, or a substituent; Ring A represents an aromatic ring which can be substituted, and Ring B represents a 5-membered heteroaromatic ring which can be substituted, or a salt thereof.
1. A compound of formula (I):
wherein
R 1 represents a substituent,
R 2 represents a hydrogen atom, or a substituent,
R 3 represents a hydrogen atom, or a substituent,
Ring A represents an aromatic ring which can be substituted, and
Ring B represents a 5-membered heteroaromatic ring which can be substituted;
wherein the substituents for R 1 , R 2 , R 3 , the “aromatic ring which can be substituted” as represented by the Ring A, and the “5-membered heteroaromatic ring which can be substituted” as represented by the Ring B, are selected from the group consisting of the following substituents as Substituent Group A:
Substituent Group A:
(1) a halogen atom;
(2) a nitro group;
(3) a cyano group;
(4) a carboxy group that can be esterified;
(5) an alkyl group which can be substituted;
(6) an alkenyl group which can be substituted;
(7) an alkynyl group which can be substituted;
(8) a C 3-7 cycloalkyl group which can be substituted;
(9) a C 6-14 aryl group which can be substituted;
(10) a C 7-16 aralkyl group which can be substituted;
(11) a C 6-14 aryl-C 2-6 alkenyl group which can be substituted;
(12) a heterocyclic group which can be substituted;
(13) a hydroxy group;
(14) an alkoxy group which can be substituted;
(15) a C 3-7 cycloalkyloxy group which can be substituted;
(16) a C 6-14 aryloxy group which can be substituted;
(17) a C 7-16 aralkyloxy group which can be substituted;
(18) an alkyl-carbonyloxy group which can be substituted;
(19) an alkoxy-carbonyloxy group which can be substituted;
(20) a mono-alkyl-carbamoyloxy group which can be substituted;
(21) a di-alkyl-carbamoyloxy group which can be substituted;
(22) a C 6-14 aryl-carbonyloxy group which can be substituted;
(23) a mono- or di-C 6-14 aryl-carbamoyloxy group which can be substituted;
(24) a heterocyclic-oxy group which can be substituted;
(25) a C 1-10 alkylsulfonyloxy (group) which can be substituted;
(26) a mercapto group;
(27) an alkylsulfanyl group which can be substituted;
(28) a C 3-7 cycloalkylsulfanyl group which can be substituted;
(29) a C 6-14 arylsulfanyl group which can be substituted;
(30) a C 7-16 aralkylsulfanyl group which can be substituted;
(31) a heterocyclic-sulfanyl group which can be substituted;
(32) a formyl group;
(33) an alkyl-carbonyl group which can be substituted;
(34) a C 3-7 cycloalkylcarbonyl group which can be substituted;
(35) a C 6-14 arylcarbonyl group which can be substituted;
(36) a C 7-16 aralkylcarbonyl group which can be substituted;
(37) a heterocyclic-carbonyl group which can be substituted;
(38) an alkylsulfonyl group which can be substituted;
(39) a C 3-7 cycloalkylsulfonyl group which can be substituted;
(40) a C 6-14 arylsulfonyl group which can be substituted;
(41) a heterocyclic-sulfonyl group which can be substituted;
(42) an alkylsulfinyl group which can be substituted;
(43) a C 3-7 cycloalkylsulfinyl group which can be substituted;
(44) a C 6-14 arylsulfinyl group which can be substituted;
(45) a heterocyclic-sulfinyl group which can be substituted;
(46) a sulfo group;
(47) a sulfamoyl group;
(48) a sulfinamoyl group;
(49) a sulfenamoyl group;
(50) a thiocarbamoyl group:
(51) a carbamoyl group which can be substituted; and
(52) (i) amino, (ii) mono- or di-alkylamino group which can be substituted, (iii) mono- or di-C 3-7 cycloalkylamino group which can be substituted, (iv) mono- or di-C 6-14 arylamino group which can be substituted, (v) mono- or di-C 7-16 aralkylamino group which can be substituted, (vi) heterocyclic amino group which can be substituted, (vii) C 6-14 aryl-carbonylamino group which can be substituted, (viii) formylamino, (ix) alkyl-carbonylamino group which can be substituted, (x) C 3-7 cycloalkyl-carbonylamino group which can be substituted, (xi) heterocyclic-carbonylamino group which can be substituted, (xii) C 3-7 cycloalkyloxy-carbonylamino group which can be substituted, (xiii) heterocyclic-oxycarbonylamino group which can be substituted, (xiv) carbamoylamino group which can be substituted, (xv) alkylsulfonylamino group which can be substituted, (xvi) C 3-7 cycloalkyl-sulfonylamino group which can be substituted, (xvii) heterocyclic sulfonylamino group which can be substituted, and (xviii) C 6-14 arylsulfonylamino group which can be substituted; and
wherein, in the Substituent Group A,
the “alkoxy-carbonyl group which can be substituted”,
the “alkyl group which can be substituted”,
the “alkenyl group which can be substituted”,
the “alkynyl group which can be substituted”,
the “alkoxy group which can be substituted”,
the “alkyl-carbonyloxy group which can be substituted”,
the “alkoxy-carbonyloxy group which can be substituted”,
the “mono-alkyl-carbamoyloxy group which can be substituted”,
the “dialkyl-carbamoyloxy group which can be substituted”,
the “alkylsulfanyl group which can be substituted”,
the “alkylcarbonyl group which can be substituted”,
the “alkylsulfonyl group which can be substituted”,
the “alkylsulfinyl group which can be substituted”,
the “alkyl-carbamoyl group which can be substituted”,
the “mono- or di-alkylamino group which can be substituted”,
the “alkyl-carbonylamino group which can be substituted”,
the “mono-(C 1-10 alkyl-carbonyl)-amino group which can be substituted”,
the “alkoxy-carbonylamino group which can be substituted”, and
the “alkylsulfonylamino group which can be substituted”,
substituents are selected from the group consisting of the following substituents as Substituent Group B:
Substituent Group B:
(a) a halogen atom;
(b) a hydroxy group;
(c) a nitro group;
(d) a cyano group;
(e) a C 6-14 aryl group which can be substituted with one or more substituents selected from the group consisting of halogen, hydroxy, cyano, amino, C 1-10 alkyl that can be halogenated, mono- or di-C 1-10 alkylamino, mono- or di-C 6-14 arylamino, mono- or di-C 7-16 aralkylamino, C 3-7 cycloalkyl, C 1-10 alkoxy, formyl, C 1-10 alkyl-carbonyl, C 3-7 cycloalkyl-carbonyl, C 6-14 aryl-carbonyl, C 7-16 aralkyl-carbonyl, C 1-10 alkoxy-carbonyl, C 6-14 aryloxy-carbonyl, C 7-16 aralkyloxy-carbonyl, C 1-10 alkylsulfanyl, C 1-10 alkylsulfinyl, C 1-10 alkylsulfonyl, carbamoyl, thiocarbamoyl, mono- or di-C 1-10 alkylcarbamoyl, and mono- or di-C 6-14 aryl-carbamoyl;
(f) a C 6-14 aryloxy group which can be substituted with one or more substituents selected from the group consisting of halogen, hydroxy, cyano, amino, C 1-10 alkyl that can be halogenated, mono- or di-C 1-10 alkylamino, mono- or di-C 6-14 arylamino, mono- or di-C 7-16 aralkylamino, C 3-7 cycloalkyl, C 1-10 alkoxy, formyl, C 1-10 alkyl-carbonyl, C 3-7 cycloalkyl-carbonyl, C 6-14 aryl-carbonyl, C 7-16 aralkyl-carbonyl, C 1-10 alkoxy-carbonyl, C 6-14 aryloxy-carbonyl, C 7-16 aralkyloxy-carbonyl, C 1-10 alkylsulfanyl, C 1-10 alkylsulfinyl, C 1-10 alkylsulfonyl, carbamoyl, thiocarbamoyl, mono- or di-C 1-10 alkylcarbamoyl, and mono- or di-C 6-14 aryl-carbamoyl;
(g) a C 7-16 aralkyloxy group which can be substituted with one or more substituents selected from the group consisting of halogen, hydroxy, cyano, amino, C 1-10 alkyl that can be halogenated, mono- or di-C 1-10 alkylamino, mono- or di-C 6-14 arylamino, mono- or di-C 7-16 aralkylamino, C 3-7 cycloalkyl, C 1-10 alkoxy, formyl, C 1-10 alkyl-carbonyl, C 3-7 cycloalkyl-carbonyl, C 6-14 aryl-carbonyl, C 7-16 aralkyl-carbonyl, C 1-10 alkoxy-carbonyl, C 6-14 aryloxy-carbonyl, C 7-16 aralkyloxy-carbonyl, C 1-10 alkylsulfanyl, C 1-10 alkylsulfinyl, C 1-10 alkylsulfonyl, carbamoyl, thiocarbamoyl, mono- or di-C 1-10 alkylcarbamoyl, and mono- or di-C 6-14 aryl-carbamoyl;
(h) a mono- or di-5- to 10-membered heterocyclic group having 1 to 4 hetero atoms selected from the group consisting of nitrogen, sulfur and oxygen which can be substituted with one or more substituents selected from the group consisting of halogen, hydroxy, cyano, amino, C 1-10 alkyl that can be halogenated, mono- or di-C 1-10 alkylamino, mono- or di-C 6-14 arylamino, mono- or di-C 7-16 aralkylamino, C 3-7 cycloalkyl, C 1-10 alkoxy, formyl, C 1-10 alkyl-carbonyl, C 3-7 cycloalkyl-carbonyl, C 6-14 aryl-carbonyl, C 7-16 aralkyl-carbonyl, C 1-10 alkoxy-carbonyl, C 6-14 aryloxy-carbonyl, C 7-16 aralkyloxy-carbonyl, C 1-10 alkylsulfanyl, C 1-10 alkylsulfinyl, C 1-10 alkylsulfonyl, carbamoyl, thiocarbamoyl, mono- or di-C 1-10 alkylcarbamoyl, and mono- or di-C 6-14 aryl-carbamoyl group;
(i) an amino group which can be substituted by one or two substituents selected from the group consisting of C 1-10 alkyl, C 2-6 alkenyl, C 6-14 aryl, C 7-16 aralkyl, heterocyclic group and heterocyclic-alkyl group (the C 1-10 alkyl, C 2-6 alkenyl, C 6-14 aryl, C 7-16 aralkyl, heterocyclic group and heterocyclic-alkyl group can be substituted with one or more substituents selected from the group consisting of halogen, hydroxy, cyano, amino, C 1-10 alkyl that can be halogenated (not the alkyl and alkenyl substituents), mono- or di-C 1-10 alkylamino, mono- or di-C 6-14 arylamino, mono- or di-C 7-16 aralkylamino, C 3-7 cycloalkyl, C 1-10 alkoxy, formyl, C 1-10 alkyl-carbonyl, C 3-7 cycloalkyl-carbonyl, C 6-14 aryl-carbonyl, C 7-16 aralkyl-carbonyl, C 1-10 alkoxy-carbonyl, C 3-7 cycloalkyloxy-carbonyl, C 6-14 aryloxy-carbonyl, C 7-16 aralkyloxy-carbonyl, C 1-10 alkylsulfanyl, C 3-7 cycloalkylsulfanyl, C 1-10 alkylsulfinyl, C 3-7 cycloalkylsulfinyl, C 1-10 alkylsulfonyl, C 3-7 cycloalkylsulfonyl, carbamoyl, thiocarbamoyl, mono- or di-C 1-10 -alkylcarbamoyl, mono- or di-C 6-14 aryl-carbamoyl group), and the “heterocyclic” and “heterocyclic” in “heterocyclic-alkyl” are the same as the aforementioned “heterocyclic group”;
(j) a C 3-7 cycloalkyl;
(k) a C 1-10 alkoxy which can be substituted with one or more substituents selected from the group consisting of halogen, hydroxy, amino, mono- or di-C 1-10 alkylamino, mono- or di-C 6-14 arylamino, C 3-7 cycloalkyl, C 1-10 alkoxy, formyl, C 1-10 alkyl-carbonyl, C 3-7 cycloalkyl-carbonyl, C 6-14 aryl-carbonyl, C 7-16 aralkyl-carbonyl, C 1-10 alkoxy-carbonyl, C 6-14 aryloxy-carbonyl, C 7-16 aralkyloxy-carbonyl, C 1-10 alkylsulfanyl, C 1-10 alkylsulfinyl, C 1-10 alkylsulfonyl, carbamoyl, thiocarbamoyl, mono- or di-C 1-10 alkylcarbamoyl, and mono- or di-C 6-14 aryl-carbamoyl;
(l) a formyl;
(m) a C 1-10 alkyl-carbonyl;
(n) a C 3-7 cycloalkyl-carbonyl;
(o) a C 6-14 aryl-carbonyl;
(p) a C 7-16 aralkyl-carbonyl;
(q) a C 1-10 alkoxy-carbonyl;
(r) a C 6-14 aryloxy-carbonyl;
(s) a C 7-16 aralkyloxy-carbonyl;
(t) a C 1-10 alkylsulfanyl;
(u) a C 1-10 alkylsulfinyl;
(v) a C 1-10 alkylsulfonyl;
(w) a carbamoyl;
(x) a thiocarbamoyl;
(y) a mono-C 1-10 alkylcarbamoyl;
(z) a di-C 1-10 alkylcarbamoyl;
(aa) a mono- or di-C 6-14 aryl-carbamoyl; and
(bb) a mono- or di-5- to 7-membered heterocyclic-carbamoyl having 1 to 4 hetero atoms selected from the group consisting of nitrogen, sulfur and oxygen; and
wherein, in the Substituent Group A,
the “C 6-14 aryloxy-carbonyl which can be substituted”,
the “C 7-16 aralkyloxy-carbonyl which can be substituted”,
the “C 3-7 cycloalkyl-C 2-6 alkynyl which can be substituted”,
the “C 3-7 cycloalkyl which can be substituted”,
the “C 6-14 aryl which can be substituted”,
the “C 7-16 aralkyl which can be substituted”,
the “C 6-14 aryl-C 2-6 alkenyl which can be substituted”,
the “heterocyclic group which can be substituted”,
the “C 3-7 cycloalkyloxy which can be substituted”,
the “C 6-14 aryloxy which can be substituted”,
the “C 7-16 aralkyloxy which can be substituted”,
the “C 6-14 aryl-carbonyloxy which can be substituted”,
the “mono- or di-C 6-14 aryl-carbamoyloxy which can be substituted”,
the “heterocyclic-oxy which can be substituted”,
the “aromatic heterocyclic-oxy which can be substituted”,
the “C 3-7 cycloalkylsulfanyl which can be substituted”,
the “C 6-14 arylsulfanyl which can be substituted”,
the “C 7-16 aralkylsulfanyl which can be substituted”,
the “heterocyclic-sulfanyl which can be substituted”,
the “C 3-7 cycloalkyl-carbonyl which can be substituted”,
the “C 6-14 aryl-carbonyl which can be substituted”,
the “C 7-16 aralkyl-carbonyl which can be substituted”,
the “heterocyclic-carbonyl which can be substituted”,
the “C 3-7 cycloalkylsulfonyl which can be substituted”,
the “C 6-14 arylsulfonyl which can be substituted”,
the “heterocyclic-sulfonyl which can be substituted”,
the “C 3-7 cycloalkylsulfinyl which can be substituted”,
the “C 6-14 arylsulfinyl which can be substituted”,
the “heterocyclic-sulfinyl which can be substituted”,
the “carbamoyl group which can be substituted”,
the “amino group which can be substituted”,
the “mono- or di-C 3-7 cycloalkylamino group which can be substituted”,
the “mono- or di-C 6-14 arylamino group which can be substituted”,
the “mono- or di-C 7-16 aralkylamino group which can be substituted”,
the “heterocyclic amino group which can be substituted”,
the “C 6-14 aryl-carbonylamino group which can be substituted”,
the “C 3-7 cycloalkyl-carbonylamino group which can be substituted”,
the “heterocyclic-carbonylamino group which can be substituted”,
the “C 3-7 cycloalkyloxy-carbonylamino group which can be substituted”,
the “heterocyclic-oxycarbonylamino group which can be substituted”,
the “carbamoylamino group which can be substituted”,
the “alkylsulfonylamino group which can be substituted”,
the “C 3-7 cycloalkyl-sulfonylamino group which can be substituted”,
the “heterocyclic sulfonylamino group which can be substituted”, and
the “C 6-14 arylsulfonylamino group which can be substituted”,
substituents are selected from the group consisting of (1) the substituents of the Substituent Group B and (2) substituents selected from the group consisting of the following Substituent Group B′:
Substituent Group B′:
(a) C 1-10 alkyl, which can be substituted by one or more substituents selected from the group consisting of halogen, hydroxy, cyano, amino, mono- or di-C 1-10 alkylamino, mono- or di-C 6-14 arylamino, mono- or di-C 7-16 aralkylamino, C 3-7 cycloalkyl, C 1-10 alkoxy, formyl, C 1-10 alkyl-carbonyl, C 3-7 cycloalkyl-carbonyl, C 6-14 aryl-carbonyl, C 7-16 aralkyl-carbonyl, C 1-10 alkoxy-carbonyl, C 6-14 aryloxy-carbonyl, C 7-16 aralkyloxy-carbonyl, C 1-10 alkylsulfanyl, C 1-10 alkylsulfinyl, C 1-10 alkylsulfonyl, carbamoyl, thiocarbamoyl, mono- or di-C 1-10 alkylcarbamoyl, and mono- or di-C 6-14 aryl-carbamoyl;
(b) C 2-6 alkenyl, which can be substituted by one or more substituents selected from the group consisting of halogen, hydroxy, cyano, amino, mono- or di-C 1-10 alkylamino, mono- or di-C 6-14 arylamino, mono- or di-C 7-16 aralkylamino, C 3-7 cycloalkyl, C 1-10 alkoxy, formyl, C 1-10 alkyl-carbonyl, C 3-7 cycloalkyl-carbonyl, C 6-14 aryl-carbonyl, C 7-16 aralkyl-carbonyl, C 1-10 alkoxy-carbonyl, C 6-14 aryloxy-carbonyl, C 7-16 aralkyloxy-carbonyl, C 1-10 alkylsulfanyl, C 1-10 alkylsulfinyl, C 1-10 alkylsulfonyl, carbamoyl, thiocarbamoyl, mono- or di-C 1-10 alkylcarbamoyl, and mono- or di-C 6-14 aryl-carbamoyl; and
(c) C 2-6 alkynyl, which can be substituted by one or more substituents selected from the group consisting of halogen atoms, hydroxy, cyano, amino, mono- or di-C 1-10 alkylamino, mono- or di-C 6-14 arylamino, mono- or di-C 7-16 aralkylamino, C 3-7 cycloalkyl, C 1-10 alkoxy, formyl, C 1-10 alkyl-carbonyl, C 3-7 cycloalkyl-carbonyl, C 6-14 aryl-carbonyl, C 7-16 aralkyl-carbonyl, C 1-10 alkoxy-carbonyl, C 6-14 aryloxy-carbonyl, C 7-16 aralkyloxy-carbonyl, C 1-10 alkylsulfanyl, C 1-10 alkylsulfinyl, C 1-10 alkylsulfonyl, carbamoyl, thiocarbamoyl, mono- or di-C 1-10 alkylcarbamoyl, and mono- or di-C 6-14 aryl-carbamoyl group; and
provided that the following compounds:
1-(2-chlorophenyl)-6-methyl-3-{5-thioxo-4-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1H-1,2,4-triazol-3-yl}pyridazin-4(1H)-one,
1-(4-chlorophenyl)-3-[4-(2-fluorophenyl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]-6-methylpyridazin-4(1H)-one,
1-(4-chlorophenyl)-6-methyl-3-{5-thioxo-4-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1H-1,2,4-triazol-3-yl}pyridazin-4(1H)-one,
1-(4-chlorophenyl)-3-[4-(2-fluorophenyl)-5-(methylsulfanyl)-4H-1,2,4-triazol-3-yl]-6-methylpyridazin-4(1H)-one,
1-(4-chlorophenyl)-6-methyl-3-{5-(methylsulfanyl)-4-[3-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}pyridazin-4(1H)-one,
1-(2-chlorophenyl)-6-methyl-3-{5-(methylsulfanyl)-4-[3-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}pyridazin-4(1H)-one,
3-(3,5-dimethyl-1H-pyrazol-1-yl)-1-phenylpyridazin-4(1H)-one,
1-(4-chlorophenyl)-3-{(1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazol-5-yl}pyridazin-4(1H)-one,
3-[1-(2-fluorophenyl)-1H-pyrazol-5-yl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one,
3-[1-(3-chlorophenyl)-1H-pyrazol-5-yl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one,
3-[1-(4-methoxyphenyl)-1H-pyrazol-5-yl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one,
3-(1-phenyl-1H-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one,
3-[1-(3-nitrophenyl)-1H-pyrazol-5-yl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one,
3-[1-(1,1-dioxidotetrahydrothiophen-3-yl)-H-pyrazol-5-yl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one,
3-[1-(4-methylphenyl)-H-pyrazol-5-yl]-1-phenylpyridazin-4(1H)-one,
3-[1-(4-chlorophenyl)-H-pyrazol-5-yl]-1-phenylpyridazin-4(1H)-one,
3-(4-ethyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-1-(4-methylphenyl)pyridazin-4(1H)-one,
a compound of formula:
wherein
Ring A′ is a benzene ring which can be substituted by one substituent selected from the group consisting of a halogen atom, and an alkyl group,
R 1′ is
(1) an ethyl group, or
(2) a phenyl group which can be substituted by one or more substituents selected from the group consisting of a fluorine atom, and a trifluoromethyl group,
R 3′ is a hydrogen atom, or a methyl group, and
Ra is a hydrogen atom, or a C 1-4 acyclic hydrocarbon group which can be substituted, and
a compound of formula:
wherein
Ring A″ is a benzene ring which can be substituted by halogen, and
R 1″ is an acyl group are excluded;
or a salt thereof.
2. The compound according to claim 1 , wherein
R 2 represents a halogen atom, a hydroxy group, a C 1-10 alkyl group which can be substituted, or a C 1-10 alkoxy group which can be substituted;
wherein the substituents of the “C 1-10 alkyl group which can be substituted” and the “C 1-10 alkoxy group which can be substituted” are selected from the group consisting of those of Substituent Group B.
3. The compound according to claim 2 , wherein
R 2 represents a C 1-10 alkoxy group which can be substituted by one or more substituents selected from the group consisting of a halogen atom, a C 1-10 alkoxy group, and a C 3-7 cycloalkyl group.
4. The compound according to claim 2 , wherein
R 2 represents a C 1-10 alkoxy group.
5. The compound according to claim 2 , wherein
R 1 represents a phenyl group which can be substituted by 1 to 5 substituents selected from the group consisting of a halogen atom, a C 1-10 alkyl group which can be substituted, and a C 1-10 alkoxy group which can be substituted;
wherein the substituents of the “C 1-10 alkyl group which can be substituted” and the “C 1-10 alkoxy group which can be substituted” are selected from the group consisting of those of Substituent Group B.
6. The compound according to claim 2 , wherein
R 1 represents a phenyl group which can be substituted by 1 to 5 substituents selected from the group consisting of a halogen atom, a C 1-10 alkyl group, and a C 1-10 alkoxy group.
7. The compound according to claim 2 , wherein
R 1 represents a phenyl group which can be substituted by 1 to 5 halogen atoms.
8. The compound according to claim 2 , wherein
R 3 represents a hydrogen atom, or a C 1-10 alkoxy group which can be substituted;
wherein the substituents of the “C 1-10 alkoxy group which can be substituted” are selected from the group consisting of those of Substituent Group B.
9. The compound according to claim 2 , wherein
R 3 represents a hydrogen atom, or a C 1-10 alkoxy group.
10. The compound according to claim 2 , wherein
R 3 represents a hydrogen atom.
11. The compound according to claim 2 , wherein
Ring A represents a benzene ring which can be substituted by 1 to 5 substituents selected from the group consisting of:
(1) a halogen atom,
(2) a C 1-10 alkyl group which can be substituted,
(3) a C 1-10 alkoxy group which can be substituted,
(4) a 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms which can be substituted,
(5) a C 1-10 alkylsulfonyl group which can be substituted,
(6) a C 3-7 cycloalkyl group which can be substituted,
(7) a cyano group,
(8) a carbamoyl group which can be substituted,
(9) a C 1-10 alkylsulfonyloxy group which can be substituted,
(10) a C 3-7 cycloalkyl-C 2-6 alkynyl group which can be substituted,
(11) a tetrahydropyranyl group which can be substituted,
(12) a dihydropyranyl group which can be substituted,
(13) a mono-(C 1-10 alkyl-carbonyl)-amino group which can be substituted,
(14) a C 1-10 alkoxy-carbonyl group which can be substituted,
(15) a C 1-10 alkylsulfinyl group which can be substituted, and
(16) a C 1-10 alkylsulfanyl group which can be substituted;
wherein the substituents of “(2) a C 1-10 alkyl group which can be substituted”, “(3) a C 1-10 alkoxy group which can be substituted”, “(5) a C 1-10 alkylsulfonyl group which can be substituted”, “(8) a carbamoyl group which can be substituted”, “(9) a C 1-10 alkylsulfonyloxy group which can be substituted”, “(13) a mono-(C 1-10 alkyl-carbonyl)-amino group which can be substituted”, “(14) a C 1-10 alkoxy-carbonyl group which can be substituted”, “(15) a C 1-10 alkylsulfinyl group which can be substituted”, and “(16) a C 1-10 alkylsulfanyl group which can be substituted” are selected from the group consisting of those of Substituent Group B; and
wherein the substituents of “(4) a 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms which can be substituted”, “(6) a C 3-7 cycloalkyl group which can be substituted”, “(10) a C 3-7 cycloalkyl-C 2-6 alkynyl group which can be substituted”, “(11) a tetrahydropyranyl group which can be substituted”, and “(12) a dihydropyranyl group which can be substituted” are selected from the group consisting of those of Substituent Group B and Substituent Group B′.
12. The compound according to claim 2 , wherein
Ring A represents a benzene ring which can be substituted by 1 to 5 substituents selected from the group consisting of:
(1) a halogen atom,
(2) a C 1-10 alkyl group which can be substituted,
(3) a C 1-10 alkoxy group which can be substituted,
(4) a C 3-7 cycloalkyl group,
(5) a halogeno C 1-10 alkylsulfonyloxy group,
(6) a C 3-7 cycloalkyl-C 2-6 alkynyl group, and
(7) a 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms which can be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, an oxo group, a C 1-10 alkoxy-carbonyl group, a C 1-10 alkoxy group which can be substituted, and a C 1-10 alkyl group which can be substituted;
wherein the substituents of
“(2) a C 1-10 alkyl group which can be substituted”,
“(3) a C 1-10 alkoxy group which can be substituted”,
“a C 1-10 alkoxy group which can be substituted” as the substituents of(7) a 4- to 6-membered heterocyclic group, and
“a C 1-10 alkyl group which can be substituted” as the substituents of (7) a 4- to 6-membered heterocyclic group,
are selected from the group consisting of those of Substituent Group B.
13. The compound according to claim 2 , wherein
Ring A represents a benzene ring which can be substituted by 1 to 5 substituents selected from the group consisting of:
(1) a halogen atom,
(2) a C 1-10 alkyl group which can be substituted by 1 to 3 halogen atoms,
(3) a C 1-10 alkoxy group which can be substituted by 1 to 3 halogen atoms,
(4) a C 3-7 cycloalkyl group,
(5) a halogeno C 1-10 alkylsulfonyloxy group,
(6) a C 3-7 cycloalkyl-C 2-6 alkynyl group, and
(7) a 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms which can be substituted by 1 to 4 substituents selected from the group consisting of a halogen atom, a hydroxy group, an oxo group, a C 1-10 alkoxy-carbonyl group, a C 1-10 alkoxy group which can be substituted by halogen, and a C 1-10 alkyl group which can be substituted by halogen.
14. The compound according to claim 2 , wherein
Ring A represents a benzene ring which is substituted with
(1) (i) 1 or 2 halogen atoms, or (ii) one C 1-10 alkoxy group, and
(2) one 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms which can be substituted by 1 to 4 substituents selected from the group consisting of a halogen atom, a hydroxy group, an oxo group, a C 1-10 alkoxy-carbonyl group, a C 1-10 alkoxy group which can be substituted by halogen, and a C 1-10 alkyl group which can be substituted by halogen.
15. The compound according to claim 14 , wherein
the 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms represents a morpholino group, a pyrrolyl group, a dihydropyrrolyl group, a pyrazolyl group, a dihydropyrazolyl group, a piperidyl group, an azetidinyl group, a pyrrolidinyl group, an oxazolidinyl group, an imidazolyl group or an imidazolidinyl group.
16. The compound according to claim 2 , wherein
Ring B represents an imidazole ring, a pyrazole ring, a triazole ring or a tetrazole ring, each of which can be further substituted with 1 to 3 substituents selected from the group consisting of a halogen atom, and a C 1-10 alkyl group which can be substituted by halogen.
17. The compound according to claim 2 , wherein
Ring B represents a pyrazole ring which can be further substituted with 1 to 3 substituents selected from the group consisting of a halogen atom, and a C 1-10 alkyl group which can be substituted by halogen.
18. The compound according to claim 2 , wherein
Ring B represents a pyrazole ring.
19. The compound according to claim 2 , wherein
R 1 represents a phenyl group which can be substituted by 1 to 5 substituents selected from the group consisting of a halogen atom, a C 1-10 alkyl group which can be substituted, and a C 1-10 alkoxy group which can be substituted,
R 2 represents a halogen atom, a hydroxy group, a C 1-10 alkyl group which can be substituted, or a C 1-10 alkoxy group which can be substituted,
R 3 represents a hydrogen atom, or a C 1-10 alkoxy group which can be substituted,
Ring A represents a benzene ring which can be substituted by 1 to 5 substituents selected from the group consisting of:
(1) a halogen atom,
(2) a C 1-10 alkyl group which can be substituted,
(3) a C 1-10 alkoxy group which can be substituted,
(4) a 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms which can be substituted,
(5) a C 1-10 alkylsulfonyl group which can be substituted,
(6) a C 3-7 cycloalkyl group which can be substituted,
(7) a cyano group,
(8) a carbamoyl group which can be substituted,
(9) a C 1-10 alkylsulfonyloxy group which can be substituted,
(10) a C 3-7 cycloalkyl-C 2-6 alkynyl group which can be substituted,
(11) a tetrahydropyranyl group which can be substituted,
(12) a dihydropyranyl group which can be substituted,
(13) a mono-(C 1-10 alkyl-carbonyl)-amino group which can be substituted,
(14) a C 1-10 alkoxy-carbonyl group which can be substituted,
(15) a C 1-10 alkylsulfinyl group which can be substituted, and
(16) a C 1-10 alkylsulfanyl group which can be substituted, and
Ring B represents an imidazole ring, a pyrazole ring, a triazole ring or a tetrazole ring, each of which can be further substituted with 1 to 3 substituents selected from the group consisting of a halogen atom, and a C 1-10 alkyl group which can be substituted by halogen,
wherein the substituents of
the “C 1-10 alkyl group which can be substituted” and the “C 1-10 alkoxy group which can be substituted” as the substituents of a phenyl group for R 1 ,
the “C 1-10 alkyl group which can be substituted” and “C 1-10 alkoxy group which can be substituted” for R 2 ,
the “C 1-10 alkoxy group which can be substituted” for R 3 ,
the “(2) C 1-10 alkyl group which can be substituted”, “(3) C 1-10 alkoxy group which can be substituted”, “(5) C 1-10 alkylsulfonyl group which can be substituted”, “(8) carbamoyl group which can be substituted”, “(9) C 1-10 alkylsulfonyloxy group which can be substituted”, “(13) mono-(C 1-10 alkyl-carbonyl)-amino group which can be substituted”, “(14) C 1-10 alkoxy-carbonyl group which can be substituted”, “(15) C 1-10 alkylsulfinyl group which can be substituted” and “(16) C 1-10 alkylsulfanyl group which can be substituted” as the substituents of a benzene ring for Ring A,
are selected from the group consisting of those of Substituent Group B; and
wherein the substituents of the “(4) 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms which can be substituted”, “(6) C 3-7 cycloalkyl group which can be substituted”, “(10) C 3-7 cycloalkyl-C 2-6 alkynyl group which can be substituted”, “(11) tetrahydropyranyl group which can be substituted”, and “(12) dihydropyranyl group which can be substituted” as the substituents of a benzene ring for Ring A,
are selected from the group consisting of those of Substituent Group B and Substituent Group B′.
20. The compound according to claim 19 , wherein
Ring A represents a benzene ring which can be substituted by 1 to 5 substituents selected from the group consisting of:
(1) a halogen atom,
(2) a C 1-10 alkyl group which can be substituted,
(3) a C 1-10 alkoxy group which can be substituted,
(4) a C 3-7 cycloalkyl group,
(5) a halogeno C 1-10 alkylsulfonyloxy group,
(6) a C 3-7 cycloalkyl-C 2-6 alkynyl group, and
(7) a 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms which can be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, an oxo group, a C 1-10 alkoxy-carbonyl group, a C 1-10 alkoxy group which can be substituted, and a C 1-10 alkyl group which can be substituted;
wherein the substituents of
the “(2) C 1-10 alkyl group which can be substituted” and “(3) C 1-10 alkoxy group which can be substituted” as the substituents of a benzene ring for Ring A, and
the “C 1-10 alkoxy group which can be substituted” and “C 1-10 alkyl group which can be substituted” as the substituents of (7) heterocyclic group,
are selected from the group consisting of those of Substituent Group B.
21. The compound according to claim 2 , wherein
R 1 represents a phenyl group which can be substituted by 1 to 5 substituents selected from the group consisting of a halogen atom, a C 1-10 alkyl group, and a C 1-10 alkoxy group,
R 2 represents a C 1-10 alkoxy group which can be substituted by one or more substituents selected from the group consisting of a halogen atom, a C 1-10 alkoxy group, and a C 3-7 cycloalkyl group,
R 3 represents a hydrogen atom, or a C 1-10 alkoxy group,
Ring A represents a benzene ring which can be substituted by 1 to 5 substituents selected from the group consisting of:
(1) a halogen atom,
(2) a C 1-10 alkyl group which can be substituted by 1 to 3 halogen atoms,
(3) a C 1-10 alkoxy group which can be substituted by 1 to 3 halogen atoms,
(4) a C 3-7 cycloalkyl group,
(5) a halogeno C 1-10 alkylsulfonyloxy group,
(6) a C 3-7 cycloalkyl-C 2-6 alkynyl group, and
(7) a 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms which can be substituted by 1 to 4 substituents selected from the group consisting of a halogen atom, a hydroxy group, an oxo group, a C 1-10 alkoxy-carbonyl group, a C 1-10 alkoxy group which can be substituted by halogen, and a C 1-10 alkyl group which can be substituted by halogen, and
Ring B represents a pyrazole ring which can be further substituted with 1 to 3 substituents selected from the group consisting of a halogen atom, and a C 1-10 alkyl group which can be substituted by halogen.
22. The compound according to claim 2 , wherein
R 1 represents a phenyl group which can be substituted by 1 to 5 halogen atoms,
R 2 represents a C 1-10 -alkoxy group,
R 3 represents a hydrogen atom,
Ring A represents a benzene ring which is substituted with
(1) (i) 1 or 2 halogen atoms, or (ii) one C 1-10 alkoxy group, and
(2) one 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms which can be substituted by 1 to 4 substituents selected from the group consisting of a halogen atom, a hydroxy group, an oxo group, a C 1-10 -alkoxy-carbonyl group, a C 1-10 -alkoxy group which can be substituted by halogen, and a C 1-10 -alkyl group which can be substituted by halogen, and
Ring B represents a pyrazole ring.
23. The compound according to claim 22 , wherein
the 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms represents a morpholino group, a pyrrolyl group, a dihydropyrrolyl group, a pyrazolyl group, a dihydropyrazolyl group, a piperidyl group, an azetidinyl group, a pyrrolidinyl group, an oxazolidinyl group, an imidazolyl group or an imidazolidinyl group.
24. The compound according to claim 1 , wherein
R 1 represents an aromatic group which can be substituted,
Ring A represents an aromatic ring which is substituted with
(a) one substituent selected from the group consisting of:
(1) a C 3-7 cycloalkyl group which can be substituted, and
(2) a 4- to 6-membered heterocyclic group containing 1 to 5 heteroatoms selected from the group consisting of a nitrogen atom, a sulfur atom, and an oxygen atom which can be substituted, and
(b) one or more further substituents,
wherein the substituents of
the “aromatic group which can be substituted” for R 1 , and
the “(1) C 3-7 cycloalkyl group which can be substituted” and “(2) 4- to 6-membered heterocyclic group containing 1 to 5 heteroatoms selected from the group consisting of a nitrogen atom, a sulfur atom, and an oxygen atom which can be substituted” of (a) one substituent,
are selected from the group consisting of those of (1) Substituent Group B and (2) Substituent Group B′; and
wherein the substituents of “(b) one or more further substituents” are selected from the group consisting of those of Substituent Group A.
25. The compound according to claim 24 , wherein
R 1 represents a phenyl group which can be substituted,
R 2 represents a hydrogen atom, a halogen atom, a hydroxy group, a C 1-10 alkyl group which can be substituted, or a C 1-10 alkoxy group which can be substituted,
R 3 represents a hydrogen atom, or a C 1-10 alkoxy group which can be substituted,
Ring A represents a benzene ring which is substituted with one substituent selected from the group consisting of:
(1) a C 3-7 cycloalkyl group which can be substituted,
(2) a dihydropyranyl group which can be substituted,
(3) a tetrahydropyranyl group which can be substituted, and
(4) a 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms which can be substituted,
and can be substituted by further substituent(s), and
Ring B represents an imidazole ring, a pyrazole ring, a triazole ring, a tetrazole ring, an isoxazole ring, an 1,3-oxazole ring, a furan ring, or a thiophene ring, each of which can be substituted,
wherein the substituents of “each of which can be substituted” for Ring B,
are selected from the group consisting of those of Substituent Group A;
wherein the substituents of
the “C 1-10 alkyl group which can be substituted” and “C 1-10 alkoxy group which can be substituted” for R 2 , and
the “C 1-10 alkoxy group which can be substituted” for R 3 ,
are selected from the group consisting of those of Substituent Group B; and
wherein the substituents of
the “phenyl group which can be substituted” for R 1 , and
the “(1) C 3-7 cycloalkyl group which can be substituted”, “(2) dihydropyranyl group which can be substituted”, “(3) tetrahydropyranyl group which can be substituted” and “(4) 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms which can be substituted, and can be substituted by further substituents” as the substituents of a benzene ring for Ring A,
are selected from the group consisting of those of Substituent Group B and Substituent Group B′.
26. The compound according to claim 25 , wherein
the 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms represents a morpholino group, a pyrrolyl group, a dihydropyrrolyl group, a pyrazolyl group, a dihydropyrazolyl group, a piperidyl group, an azetidinyl group, a pyrrolidinyl group, an oxazolidinyl group, an imidazolyl group, an imidazolidinyl group, an isoxazolyl group, a pyridyl group, a piperazinyl group, or a thiazolyl group.
27. The compound according to claim 24 , wherein
the (b) one or more further substituents are 1 to 4 substituents selected from the group consisting of:
(1) a halogen atom,
(2) an oxo group,
(3) a hydroxy group,
(4) a C 1-10 alkyl group which can be substituted,
(5) a C 1-10 alkoxy group which can be substituted,
(6) a C 1-10 alkylsulfonyl group,
(7) a morpholin-4-yl sulfonyl group,
(8) a cyano group,
(9) a carbamoyl group,
(10) a halogeno C 1-10 alkylsulfonyloxy group,
(11) a C 3-7 cycloalkyl-C 2-6 alkynyl group,
(12) a di-C 1-10 alkyl-amino group,
(13) a mono-(C 1-10 alkyl-carbonyl)-amino group,
(14) a C 1-10 alkoxy-carbonyl group,
(15) a phenoxy group,
(16) a C 1-10 alkylsulfinyl group,
(17) a benzimidazole-2-yloxy group, and
(18) a benzimidazole-2-yl sulfonyl group;
wherein the substituents of the “(4) C 1-10 alkyl group which can be substituted” and “(5) C 1-10 alkoxy group which can be substituted” are selected from the group consisting of those of Substituent Group B.
28. The compound according to claim 24 , wherein
R 1 represents a phenyl group which can be substituted by 1 to 5 halogen atoms,
R 2 represents a hydrogen atom or a C 1-10 alkoxy group,
R 3 represents a hydrogen atom,
Ring A represents a benzene ring,
which is substituted with one 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms which can be substituted by 1 to 4 substituents selected from the group consisting of a halogen atom, a hydroxy group, an oxo group, halogeno C 1-10 alkoxy group, a C 1-10 alkoxy-carbonyl, and a C 1-10 alkyl group which can be substituted by halogen,
and which can be further substituted with 1 or 2 substituents selected from the group consisting of a halogen atom and a C 1-10 alkoxy group, and
Ring B represents a pyrazole ring.
29. The compound according to claim 28 , wherein
the 4- to 6-membered heterocyclic group containing 0 or 1 oxygen atom, and 1 to 3 nitrogen atoms as heteroatoms represents a morpholino group, a pyrrolyl group, a dihydropyrrolyl group, a pyrazolyl group, a dihydropyrazolyl group, a piperidyl group, an azetidinyl group, a pyrrolidinyl group, an oxazolidinyl group, an imidazolyl group or an imidazolidinyl group.
30. 1-[2-fluoro-4-(2-oxopyrrolidin-1-yl)phenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one, or a salt thereof.
31. 1-[4-(3,4-difluoro-1H-pyrrol-1-yl)-2-fluorophenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one, or a salt thereof.
32. 1-[2-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one, or a salt thereof.
33. 3-[1-(2-fluorophenyl)-1H-pyrazol-5-yl]-1-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-5-methoxypyridazin-4(1H)-one, or a salt thereof.
34. 3-[1-(3-chlorophenyl)-1H-pyrazol-5-yl]-1-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-5-methoxypyridazin-4(1H)-one, or a salt thereof.
35. 1-[4-(4,4-dimethyl-2-oxopyrrolidin-1-yl)-2-fluorophenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one, or a salt thereof.
36. 1-[4-(5,5-dimethyl-2-oxo-1,3-oxazolidin-3-yl)-2-fluorophenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one, or a salt thereof.
37. 5-methoxy-1-[2-methoxy-4-(1H-pyrazol-1-yl)phenyl]-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one, or a salt thereof.
38. A pharmaceutical composition comprising the compound according to claim 1 or a salt thereof, and a pharmaceutically acceptable carrier.