Patent ID: 6140325
Filing Date: 2000-10-31
Classification: C07D

Abstract:
A compound of the formula: ##STR26## wherein R.sup.1 is hydrogen, C.sub.1-6 alkyl or a group of the formula: --(CH.sub.2)mQ' in which m is an integer of 0-3, Q' is C.sub.6-14 aryl which may be substituted by (i) halogen, (ii) nitro, (iii) cyano, (iv) amino, (v) carboxyl which may be substituted with C.sub.1-3 alkyl, C.sub.3-7 cycloalkyl, phenyl, naphthyl, C.sub.7-10 aralkyl, or heterocyclic group which is 5- to 13-membered aromatic heterocyclic group having 1-4 heteroatoms selected from oxygen, sulfur and nitrogen as the atom for constituting the ring or a saturated or unsaturated non-aromatic heterocyclic group selected from the group consisting of oxiranyl, azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuryl, thiolanyl, piperidyl, tetrahydropyranyl, morpholinyl, thiomorpholinyl and piperazinyl each of which may have one to three substituents selected from the group consisting of C.sub.1-3 alkyl, C.sub.2-4 alkenyl, C.sub.3-4 alkynyl, C.sub.3-7 cycloalkyl, phenyl, naphthyl, a 5- to 9-membered aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, a 5- to 9-membered non-aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, C.sub.7-10 aralkyl, amino, monoalkylamino having 1-6 carbons, N,N-disubstituted amino wherein the substituents are alkyl having 2-6 carbons, amidino, C.sub.1-8 alkyl-carbonyl, C.sub.6-14 aryl-carbonyl, carbamoyl, C.sub.1-6 alkyl-carbamoyl, N,N-disubstituted carbamoyl substituted with C.sub.1-6 alkyl, sulfamoyl, N-alkylsulfamoyl substituted with C.sub.1-6 alkyl, N,N-disubstituted sulfamoyl substituted with C.sub.1-6 alkyl, carboxyl, C.sub.1-3 alkoxy-carbonyl, hydroxyl, optionally-substituted C.sub.1-3 alkoxy which may be substituted with C.sub.1-3 lower alkyl, halogen, C.sub.1-3 alkylthio or hydroxyl, C.sub.2-4 alkenyloxy, C.sub.3-7 cycloalkyloxy, C.sub.7-10 aralkyloxy, phenyloxy, naphthyloxy, mercapto, C.sub.1-3 alkyl, alkylthio, C.sub.7-10 aralkylthio, phenylthio, naphthylthio, alkylenedioxy having 1-3 carbons, sulfo, cyano, azido, nitro, nitroso and a halogen atom, (vi) C.sub.1-6 alkylenedioxy or (vii) a group of the formula: --A--R.sup.6 which A is a chemical bond or a connecting group selected from the group consisting of (1) C.sub.1-4 alkylene, (2) C.sub.2-6 alkenylene, (3) --(CH.sub.2).sub.c NR.sup.10 -- in which c is an integer of 0-3 and R.sup.10 is hydrogen or C.sub.1-6 alkyl, (4) --CO--, (5) a group of the formula: --CONR.sup.10 -- in which R.sup.10 has the same meaning as defined above, (6) --O--, (7) --S--, and (8) a group of the formula: --NR.sup.10 SO.sub.e -- in which e is an integer of 0-2 and R.sup.10 has the same meaning as defined above, R.sup.6 is (i) C.sub.1-6 alkyl, (ii) C.sub.3-10 cycloalkyl which may have one to three substituents selected from the group consisting of C.sub.1-3 alkyl, C.sub.2-4 alkenyl, C.sub.3-4 alkynyl, C.sub.3-7 cycloalkyl, phenyl, naphthyl, a 5- to 9-membered aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, a 5- to 9-membered non-aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, aralkyl having 7-10 carbons, amino, monoalkylamino having 1-6 carbons, N,N-disubstituted amino wherein the substituents are alkyl having 2-6 carbons, amidino, C.sub.1-8 alkyl-carbonyl, arylcarbonyl having 6-14 carbons, carbamoyl, C.sub.1-6 alkyl-carbamoyl, N,N-disubstituted carbamoyl substituted with alkyl having 1-6 carbons, sulfamoyl, N-alkyl-sulfamoyl substituted with alkyl having 1-6 carbons, N,N-disubstituted sulfamoyl substituted with alkyl having 1-6 carbons, carboxyl, C.sub.1-3 alkoxy-carbonyl, hydroxyl, optionally-substituted C.sub.1-3 alkoxy which may be substituted with C.sub.1-3 lower alkyl, halogen, C.sub.1-3 alkylthio or hydroxyl, C.sub.2-4 alkenyloxy, C.sub.3-7 cycloalkyloxy, C.sub.7-10 aralkyloxy, phenyloxy, naphthyloxy, mercapto, C.sub.1-3 alkylthio, C.sub.7-10 aralkylthio, phenylthio, naphthylthio, alkylenedioxy having 1-3 carbons, sulfo, cyano, azido, nitro, nitroso and a halogen atom, or (iii) a 5-to 13-membered aromatic heterocyclic group having 1-4 heteroatoms selected from oxygen, sulfur and nitrogen as the atom for constituting the ring or a saturated or unsaturated non-aromatic heterocyclic group selected from the group consisting of oxiranyl, azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuryl, thiolanyl, piperidyl, tetrahydropyranyl, morpholinyl, thiomorpholinyl and piperazinyl each of which may have one to three substituents selected from the group consisting of C.sub.1-3 alkyl, C.sub.2-4 alkenyl, C.sub.3-4 alkynyl, C.sub.3-7 cycloalkyl, phenyl, naphthyl, a 5- to 9-membered aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, a 5- to 9-membered non-aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, aralkyl having 7-10 carbons, amino, monoalkylamino having 1-6 carbons, N,N-disubstituted amino wherein the substituents are alkyl having 2-6 carbons, amidino, C.sub.1-8 alkyl-carbonyl, C.sub.6-14 aryl-carbonyl, carbamoyl, C.sub.1-6 alkyl-carbamoyl, N,N-disubstituted carbamoyl substituted with alkyl having 1-6 carbons, sulfamoyl, N-alkyl-sulfamoyl substituted with alkyl having 1-6 carbons, N,N-disubstituted sulfamoyl substituted with alkyl having 1-6 carbons, carboxyl, C.sub.1-3 alkoxy-carbonyl, hydroxyl, optionally-substituted alkoxy having 1-3 carbons which may be substituted with C.sub.1-3 alkyl, halogen, C.sub.1-3 alkylthio or hydroxyl, alkenyloxy having 2-4 carbons, cycloalkyloxy having 3-7 carbons, aralkyloxy having 7-10 carbons, phenyloxy, naphthyloxy, mercapto, alkylthio having 1-3 carbons, aralkylthio having 7-10 carbons, phenylthio, naphthylthio, alkylenedioxy having 1-3 carbons, sulfo, cyano, azido, nitro, nitroso and a halogen atom;R.sup.2 is (i) hydrogen, (ii) a C.sub.1-6 alkyl, (iii) C.sub.3-6 cycloalkyl, (iv) C.sub.2-6 alkenyl, (v) C.sub.6-14 aryl or (vi) C.sub.7-20 aralkyl each of which (ii) to (vi) may have substituents of (1) nitro, (2) hydroxyl, (3) oxo, (4) thioxo, (5) cyano, (6) carbamoyl, (7) carboxyl, (8) C.sub.1-4 alkoxy-carbonyl, (9) sulfo, (10) halogen, (11) C.sub.1-8 alkoxy, (12) C.sub.6-12 aryloxy, (13) halogeno C.sub.6-16 aryl, (14) C.sub.1-6 alkylthio, (15) C.sub.6-12 arylthio, (16) C.sub.1-6 alkylsulfinyl, (17) C.sub.1-6 alkylsulfonyl, (18) amino, (19) C.sub.1-4 acylamino selected from the group consisting of formylamino, acetylamino and propionylamino, (20) mono- or di-C.sub.1-4 alkylamino, (21) acyl selected from the group consisting of formyl, acetyl and hexanoyl, (22) C.sub.6-12 aryl-carbonyl, (23) a 5- or 6-membered heterocyclic group having 1-4 heteroatoms selected from oxygen, sulfur and nitrogen, which may be substituted with one to four substituent(s) selected from (a) halogen, (b) C.sub.1-4 alkyl and (c) halogenophenoxy, or (24) C.sub.1-10 haloalkyl;R.sup.3 is hydrogen,or a group bonded through a carbon atom selected from the group consisting of C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.1-3 alkoxy C.sub.1-6 alkyl, hydroxy C.sub.1-6 alkyl, C.sub.2-6 alkenyl, formyl, carboxyl, C.sub.1-6 alkoxycarbonyl, cyano, mono- or di-C.sub.1-6 alkylcarbamoyl, amidino, C.sub.6-14 aryl, C.sub.7-20 aralkyl, a five-membered group having one to four hetero atoms selected from the group consisting of 2- or 3-thienyl, 2- or 3-furyl, 2- or 3-pyrrolyl, 2-, 4- or 5-oxazolyl, 2-, 4- or 5-thiazolyl, 3-, 4- or 5-pyrazolyl pyrrolidinyl, 2-, 4- or 5-imidazolyl, 3- 4- or 5-isoxazolyl, 3-, 4- or 5-isothiazolyl, 3- or 5-(1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl, 3- or 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4- or 5-(1,2,3-thiadiazolyl), 1,2,5-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, and 1H- or 2H-tetrazolyl, a six-membered group having one to four hetero atoms selected from the group consisting of 2-, 3- or 4-pyridyl, N-oxido-2-, 3- or 4-pyridyl, 2-, 4- or 5-pyrimidinyl, N-oxido-2-, 4- or 5-pyrimidinyl, 2- or 3-thiomorpholinyl, 2- or 3-morpholinyl, piperidyl, pyranyl, thiopyranyl, 1,4-oxazinyl, 1,4-thiazinyl, 1,3-thiazinyl, piperazinyl, triazinyl, oxotriazinyl, 3- or 4-pyridazinyl, pyrazinyl, N-oxido-3- and 4-pyridazinyl, and a bicyclic or tricyclic condensed group having one to four hetero atoms selected from the group consisting of benzofuryl, benzothiazolyl, benzoxazolyl, pyrrolo(1,2-b)pyridazinyl, pyrazolo(1,5-b)pyridyl, imidazo(1,2-a)pyridyl, triazolo(4,5-b)pyridazinyl, imidazo(1,2-b)pyridazinyl, 1,2,4-triazolo(4,3-a)pyridyl, benzimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolidinyl, quinolidinyl, 1,8-naphthylidinyl, purinyl, pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, chromanyl, benzoxazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, phthalazinyl, naphthyridiryl, phenoxathiinyl, phenanthrolinyl and thianthrenyl,or a group bonded through a nitrogen atom selected from the group consisting of(a) amino,(b) -NR.sup.8 R.sup.9, in which R.sup.8 is hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.6-14 aryl or a heterocyclic group which is 5-to 13-membered aromatic heterocyclic group selected from the group consisting of furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, furazanyl, 1,2,3 thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl, and triazinyl, and aromatic fused heterocyclic group selected from the group consisting of benzofuranyl, isobenzofuranyl, benzo(b)thienyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, 1,2-benzoisoxazolyl, benzothiazolyl, 1,2-benzoisothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthylidinyl, purinyl, pteridinyl, carbazolyl, alpha-carbolinyl, beta-carbolinyl, gamma-carbolinyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathinyl, thianthrenyl, phenathridinyl, phenathrolinyl, pyrrolo( 1,2-b)pyridazinyl, pyrazolo( 1,5-a)pyridyl, imidazo(1 ,2-a)pyridyl, imidazo(1,5-a)pyridyl, imidazo(1,2-b)pyridazinyl, 1,2,4-triazolo(4,3-a)pyridyl and 1,2,4-triazolo(4,3-b)pyridazinyl or a saturated or unsaturated non-aromatic heterocyclic group selected from the group consisting of oxiranyl, azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuryl, thiolanyl, piperidyl, tetrahydropyranyl, morpholinyl, thiomorpholinyl and piperazinyl each of which may have one to three is selected from the group consisting of C.sub.1-3 alkyl, C.sub.2-4 alkenyl, C.sub.3-4 alkynyl, C.sub.3-7 cycloalkyl, phenyl, naphthyl, a 5- to 9-membered aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, a 5- to 9-membered non-aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, aralkyl having 7-10 carbons, amino, monoalkylamino having 1-6 carbons, N,N-disubstituted amino wherein the substituents are alkyl having 2 to 6 carbon aminos, C.sub.1-8 alkyl-carbanoyl, C.sub.6-14 aryl-carbonyl, carbamoyl, C.sub.1-6 alkyl-carbamoyl, N,N-disubstituted carbamoyl substituted with alkyl having 1-6 carbons, sulfamoyl, N-alkylsulfamoyl substituted with alkyl having 1-6 carbons, N,N-disubstituted sulfamoyl substituted with alkyl having 1-6 carbons, carboxyl, C.sub.1-3 alkoxy-carbonyl, hydroxyl, optionally-substituted alkoxy having 1-3 carbons which may be substituted with C.sub.1-3 alkyl, halogen, C.sub.1-3 alkylthio or hydroxyl, alkenyloxy having 2-4 carbons, cycloalkyloxy having 3-7 carbons, aralkyloxy having 7-10 carbons, phenyloxy, naphthyloxy, mercapto, alkylthio having 1-3 carbons, aralkylthio having 7-10 carbons, phenylthio, naphthylthio, alkylenedioxy having 1-3 carbons, sulfo, cyano, azido, nitro, nitroso and a halogen atom, and R.sup.9 is hydrogen or C.sub.1-6 alkyl, and(c) a heterocyclic group selected from the group consisting of 1H-1-pyrrolyl, 1-imidazolinyl, 1-pyrazolyl, 1-indolyl, 1H-1-indazolyl, 7-purinyl, 1-pyrrolidinyl, 1-pyrrolinyl, 1-imidazolinyl, 1-pyrazolidinyl, 1-piperazinyl, 1-pyrazolinyl, 1-piperidinyl, 4-morpholinyl and 4-thiomorpholinyl;R.sup.4 is (A) C.sub.6-14 aryl which may have one to three substituents selected from the group consisting of (1) C.sub.1-3 alkyl, (2) C.sub.2-4 alkenyl, (3) C.sub.3-4 alkynyl, (4) C.sub.3-7 cycloalkyl, (5) phenyl, (6) naphthyl, (7) a 5- to 9-membered aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, (8) a 5- to 9-membered non-aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, (9) C.sub.7-10 aralkyl, (10) amino, (11) monoalkylamino having 1-6 carbons, (12) N,N-disubstituted amino wherein the substituents are C.sub.2-6 alkyl, (13) amidino, (14) C.sub.1-8 alkyl-carbonyl, (15) C.sub.6-14 aryl-carbonyl, (16) carbamoyl, (17) C.sub.1-6 alkyl-carbamoyl, (18) N,N-disubstituted carbamoyl substituted with C.sub.1-6 alkyl, (19) sulfamoyl, (20) N-alkylsulfamoyl substituted with alkyl having 1-6 carbons, (21) N,N-disubstituted sulfamoyl substituted with alkyl having 1-6 carbons, (22) carboxyl, (23) C.sub.1-3 alkoxy-carbonyl, (24) hydroxyl, (25) optionally-substituted C.sub.1-3 alkoxy which may be substituted with C.sub.1-3 alkyl, halogen, C.sub.1-3 alkylthio or hydroxyl, (26) alkenyloxy having 2-4 carbons, (27) cycloalkyloxy having 3-7 carbons, (28) aralkyloxy having 7-10 carbons, (29) phenyloxy, (30) naphthyloxy, (31) mercapto, (32) alkylthio having 1-3 carbons, (33) aralkylthio having 7-10 carbons, (34) phenylthio, (35) naphthylthio, (36) alkylenedioxy having 1-3 carbons, (37) sulfo, (38) cyano, (39) azido, (40) nitro, (41) nitroso and (42) a halogen atom,(B) C.sub.3-10 cycloalkyl which may have one to three substituents selected from the group consisting of (1) C.sub.1-3 alkyl, (2) C.sub.2-4 alkenyl, (3) C.sub.3-4 alkynyl, (4) C.sub.3-7 cycloalkyl, (5) phenyl, (6) naphthyl, (7) a 5- to 9-membered aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, (8) a 5- to 9-membered non-aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, (9) C.sub.7-10 aralkyl, (10) amino, (11) monoalkylamino having 1-6 carbons, (12) N,N-disubstituted amino wherein the substituents are alkyl having 2-6 carbons, (13) amidino, (14) C.sub.1-8 alkyl-carbonyl, (15) C.sub.6-14 aryl-carbonyl, (16) carbamoyl, (17) C.sub.1-6 alkyl-carbamoyl, (18) N,N-disubstituted carbamoyl substituted with alkyl having 1-6 carbons, (19) sulfamoyl, (20) N-aikylsulfamoyl substituted with alkyl having 1-6 carbons, (21) N,N-disubstituted sulfamoyl substituted with alkyl having 1-6 carbons, (22) carboxyl, (23) alkoxycarbonyl having 1-3 carbons, (24) hydroxyl, (25) optionally-substituted alkoxy having 1-3 carbons which may be substituted with C.sub.1-3 alkyl, halogen, C.sub.1-3 alkylthio or hydroxyl, (26) alkenyloxy having 2-4 carbons, (27) cycloalkyloxy having 3-7 carbons, (28) aralkyloxy having 7-10 carbons, (29) phenyloxy, (30) naphthyloxy, (31) mercapto, (32) alkylthio having 1-3 carbons, (33) aralkylthio having 7-10 carbons, (34) phenylthio, (35) naphthylthio, (36) alkylenedioxy having 1-3 carbons, (37) sulfo, (38) cyano, (39) azido, (40) nitro, (41) nitroso and (42) a halogen atom,(C) a 5-to 13-membered aromatic heterocyclic group having 1-4 heteroatoms selected from oxygen, sulfur and nitrogen as the atom for constituting the ring,(D) a saturated or unsaturated non-aromatic heterocyclic group selected from the group consisting of oxiranyl, azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuryl, thiolanyl, piperidyl, tetrahydropyranyl, morpholinyl, thiomorpholinyl and piperazinyl each of which may have one to three substituents selected from the group consisting of (1) C.sub.1-3 alkyl, (2) C.sub.2-4 alkenyl, (3) C.sub.3-4 alkynyl, (4) C.sub.3-7 cycloalkyl, (5) phenyl, (6) naphthyl, (7) a 5- to 9-membered aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, (8) a 5- to 9-membered non-aromatic heterocyclic group having 1-4 heteroatoms selected from nitrogen, oxygen and sulfur, (9) aralkyl having 7-10 carbons, (10) amino, (11) monoalkylamino having 1-6 carbons, (12) N,N-disubstituted amino wherein the substituents are alkyl having 2-6 carbons (13), amidino, (14) C.sub.1-8 alkyl-carbonyl, (15) C.sub.6-14 aryl-carbonyl, (16) carbamoyl, (17) C.sub.1-6 alkyl-carbamoyl, (18) N,N-disubstituted carbamoyl substituted with alkyl having 1-6 carbons, (19) sulfamoyl, (20) N-alkylsulfamoyl substituted with alkyl having 1-6 carbons, (21) N,N-disubstituted sulfamoyl substituted with alkyl having 1-6 carbons, (22) carboxyl, (23) C.sub.1-3 alkoxy-carbonyl, (24) hydroxyl, (25) optionally-substituted alkoxy having 1-3 carbons which may be substituted with C.sub.1-3 lower alkyl, halogen, C.sub.1-3 alkylthio or hydroxyl, (26) alkenyloxy having 2-4 carbons, (27) cycloalkyloxy having 3-7 carbons, (28) aralkyloxy having 7-10 carbons, (29) phenyloxy, (30) naphthyloxy, (31) mercapto, (32) alkylthio having 1-3 carbons, (33) aralkylthio having 7-10 carbons, (34) phenylthio, (35) naphthylthio, (36) alkylenedioxy having 1-3 carbons, (37) sulfo, (38) cyano, (39) azido, (40) nitro, (41) nitroso and a (42) halogen atom, or(E) a group of the formula: --COOR.sup.5' (in which R.sup.5' is hydrogen or C.sub.1-6 alkyl);W is a chemical bond or a connecting group selected from the group consisting of (1) C.sub.1-4 alkylene, (2) C.sub.2-6 alkenylene, (3) --(CH.sub.2).sub.c NR.sup.10 -- (in which c is an integer of 0-3 and R.sup.10 is hydrogen or C.sub.1-6 alkyl), (4) --CO--, (5) a group of the formula: --CONR.sup.10 -- (in which R.sup.10 has the same meaning as defined above), (6) --O--, (7) --S--, and (8) a group of the formula: --NR.sup.10 SO.sub.e -- in which e is an integer of 0-2 and R.sup.10 has the same meaning as defined above and n is an integer of 1-3,or a salt thereof.