US2014031334A1PendingUtilityA1
Derivatives of 4-piperazin-1-yl-4-benzo[b]thiophene suitable for the treatment of cns disorders
Est. expiryAug 31, 2025(expired)· nominal 20-yr term from priority
Inventors:Hiroshi YamashitaHideaki KurodaNobuaki ItoKunio OshimaJun MatsubaraTae FukushimaSatoshi ShimizuKazumi KondoMotohiro Itotani
A61P 43/00A61P 25/18A61P 25/24A61P 25/04A61P 25/36A61P 25/00A61P 25/22A61P 25/28A61P 25/14A61P 25/30A61P 29/00A61P 25/20A61P 25/16A61P 3/04A61P 25/32A61P 25/06A61P 15/10A61P 1/08A61P 1/14C07D 409/12C07D 333/54C07D 413/12C07D 491/113C07D 407/12C07D 487/08C07D 417/12C07D 409/14C07D 413/14
55
PatentIndex Score
0
Cited by
0
References
0
Claims
Abstract
A heterocyclic compound or a salt thereof represented by the formula (1): where R 2 represents a hydrogen atom or a lower alkyl group; A represents a lower alkylene group or lower alkenylene group; and R 1 represents an aromatic group or a heterocyclic group. The compound of the present invention has a wide treatment spectrum for mental disorders including central nervous system disorders, no side effects and high safety.
Claims
exact text as granted — not AI-modified1 . A heterocyclic compound or a salt thereof represented by formula (1):
where R 2 represents a hydrogen atom or a lower alkyl group;
A represents a lower alkylene group or a lower alkenylene group; and
R 1 represents heterocyclic group selected from the group consisting of (I) and (II)) below:
(I) a saturated or unsaturated heteromonocyclic group having 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom; and
(II) a benzene fused heterocyclic group that has 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom and that is selected from the group consisting of (1) a tetrahydroquinoxalinyl group, (2) a tetrahydroquinazolinyl group, (3) a dihydroquinazolinyl group, (4) an indolinyl group, (5) an indolyl group, (6) an isoindolinyl group, (7) a benzimidazolyl group, (8) a dihydrobenzimidazolyl group, (9) a tetrahydrobenzazepinyl group, (10) a tetrahydrobenzodiazepinyl group, (11) a hexahydrobenzazocinyl group, (12) a dihydrobenzoxazinyl group, (13) a dihydrobenzoxazolyl group, (14) a benzisoxazolyl group, (15) a benzoxadiazolyl group, (16) a tetrahydrobenzoxazepinyl group, (17) a dihydrobenzothiazinyl group, (18) a benzothiazolyl group, (19) a benzoxathiolyl group, (20) a chromenyl group, (21) a dihydrobenzofuryl group, (22) a carbazolyl group, (23) a dibenzofuryl group, and (24) a quinoxalinyl group,
wherein at least one group selected from the group consisting of the groups (1) to (66) below ay be present as a substituent on the heterocyclic group represented by R 1 :
(1) a lower alkyl group,
(2) a lower alkenyl group,
(3) a halogen substituted lower alkyl group,
(4) a lower alkoxy group,
(5) an aryloxy group,
(6) a lower alkylthio group,
(7) a halogen substituted lower alkoxy group.,
(8) a hydroxy group,
(9) a protected hydroxy group,
(10) a hydroxy lower alkyl group,
(11) a protected hydroxy lower alkyl group,
(12) a halogen atom,
(13) a cyano group,
(14) an aryl group,
(15) a nitro group,
(16) an amino group,
(17) an amino group having a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a carbamoyl group, a lower alkyl carbamoyl group, an amino lower alkanoyl group, a lower alkanoylamino lower alkanoyl group, and a lower alkoxy carbonylamino lower alkanoyl group as a substituent,
(18) a lower alkanoyl group,
(19) an arylsulfonyl group that may have a lower alkyl group(s) on the aryl group,
(20) a carboxy group,
(21) a lower alkoxycarbonyl group,
(22) a carboxy lower alkyl group,
(23) a lower alkoxycarbonyl lower alkyl group,
(24) a lower alkanoylamino lower alkanoyl group,
(25) a carboxy lower alkenyl group,
(26) a lower alkoxycarbonyl lower alkenyl group,
(27) a carbamoyl lower alkenyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a halogen substituted lower alkyl group as a substituent,
(28) a carbamoyl group that may have a group(s) selected from the group consisting of the groups (i) to (lxxviii) below as a substituent:
(i) a lower alkyl group,
(ii) a lower alkoxy group,
(iii) a hydroxy lower alkyl group,
(iv) a lower alkoxy lower alkyl group,
(v) an aryloxy lower alkyl group,
(vi) a halogen substituted lower alkyl group,
(vii) an amino lower alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, an aroyl group, and a carbamoyl group,
(viii) a cyclo C3-C8 alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a hydroxy group, a lower alkoxycarbonyl group, and a phenyl lower alkoxy group as a substituent,
(ix) a cyclo C3-C8 alkyl substituted lower alkyl group,
(x) a lower alkenyl group,
(xi) a carbamoyl lower alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, phenyl group that may have a lower alkyl group(s), and a phenyl group(s) that may have a lower alkoxy group(s) as a substituent,
(xii) a lower alkoxycarbonyl lower alkyl group,
(xiii) a furyl lower alkyl group (that may have a lower alkyl group(s) as a substituent) on the furyl group,
(xiv) a tetrahydrofuryl lower alkyl group,
(xv) a 1,3-dioxolanyl lower alkyl group,
(xvi) a tetrahydropyranyl lower alkyl group,
(xvii) a pyrrolyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the pyrrolyl group),
(xviii) a lower alkyl group substituted with a dihydropyrazolyl group that may have an oxo group(s),
(xix) a pyrazolyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the pyrazolyl group),
(xx) an imidazolyl lower alkyl group,
(xxi) a pyridyl lower alkyl group,
(xxii) a pyrazinyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the pyrazinyl group),
(xxiii) a pyrrolidinyl lower alkyl group (that may have a group(s) selected from the group consisting of an oxo group(s) and a lower alkyl group as a substituent on the pyrrolidinyl group),
(xxiv) a piperidyl lower alkyl group (that may have a group(s) selected from the group consisting of a benzoyl group and a lower alkanoyl group as a substituent on the piperidyl group),
(xxv) a piperazinyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the piperazinyl group),
(xxvi) a morpholinyl lower alkyl group,
(xxvii) a thienyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the thienyl group),
(xxviii) a thiazolyl lower alkyl group,
(xxix) a dihydrobenzofuryl lower alkyl group,
(xxx) a benzopyranyl lower alkyl group (that may have an oxo group(s) as a substituent on the benzopyranyl group),
(xxxi) a benzimidazolyl lower alkyl group,
(xxxii) an indolyl lower alkyl group that may have a lower alkoxycarbonyl group(s) on the lower alkyl group,
(xxxiii) an imidazolyl lower alkyl group that has a substituent(s) selected from the group consisting of a carbamoyl group and a lower alkoxycarbonyl group on the lower alkyl group,
(xxxiv) a pyridyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxy group, and a lower alkylthio lower alkyl group as a substituent,
(xxxv) a pyrrolidinyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group and an aroyl group as a substituent,
(xxxvi) a piperidyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, and an aroyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a halogen atom as a substituent,
(xxxvii) a tetrahydrofuryl group that may have an oxo group(s),
(xxxviii) a hexahydroazepinyl group that may have an oxo group(s),
(xxxix) a pyrazolyl group that may have a group(s) selected from the group consisting of a lower alkyl group, an aryl group and a fury) group as a substituent,
(xi) a thiazolyl group,
(xli) a thiadiazolyl group that may have a lower alkyl group(s),
(xlii) an isoxazolyl group that may have a lower alkyl group(s),
(xliii) an indazolyl group,
(xliv) an indolyl group,
(xlv) a tetrahydrobenzothiazolyl group,
(xlvi) a tetrahydroquinolyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen atom, and an oxo group as a substituent,
(xlvii) a quinolyl group that may have a lower alkyl group(s),
(xlviii) a benzodioxolyl lower alkyl group,
(xlix) an aryl group that may have a group(s) as a substituent, selected from the group consisting of a halogen atom; a lower alkyl group; a lower alkoxy group; a halogen substituted lower alkyl group; a halogen substituted lower alkoxy group; a lower alkenyl group; an amino group that may have a group selected from the group consisting of a lower alkanoyl group, a lower alkyl sulfonyl group, a lower alkyl group and an aryl group; a sulfamoyl group; a lower alkylthio group; a lower alkanoyl group; a lower alkoxycarbonyl group; a pyrrolyl group; a lower alkynyl group; a cyano group; a nitro group; an aryloxy group; an aryl lower alkoxy group; a hydroxy group; a hydroxy lower alkyl group; a carbamoyl group that may have a group(s) selected from the group consisting of a lower alkyl group and an aryl group; a pyrazolyl group; a pyrrolidinyl group that may have an oxo group(s); an oxazolyl group; an imidazolyl group that may have a lower alkyl group(s); a dihydrofuryl group that may have an oxo group(s); a thiazolidinyl lower alkyl group that may have an oxo group(s); an imidazolyl lower alkanoyl group; and a piperidinylcarbonyl group,
(l) a cyano lower alkyl group,
(li) a dihydroquinolyl group that may have a group(s) selected from the group consisting of a lower alkyl group and an oxo group,
(lii) a halogen substituted lower alkylamino group,
(liii) a lower alkylthio lower alkyl group,
(liv) an amidino group that may have a lower alkyl group(s),
(lv) an amidino lower alkyl group,
(lvi) a lower alkenyloxy lower alkyl group,
(lvii) an arylamino group that may have a substituent(s) selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen substituted lower alkyl group, and a halogen substituted lower alkoxy group, on the aryl group,
(lviii) an aryl lower alkenyl group,
(lix) a pyridylamino group that may have a lower alkyl group(s),
(lx) an aryl lower alkyl group (that may have on the aryl group and/or the lower alkyl group a group(s) selected from the group consisting of a halogen atom, a lower alkyl group, a halogen substituted lower alkyl group, a halogen substituted lower alkoxy group, a lower alkoxy group, a carbamoyl group and a lower alkoxycarbonyl group as a substituent),
(lxi) a lower alkynyl group,
(lxii) an aryloxy lower alkyl group (that may have as a substituent on the aryl group a group(s) selected from the group consisting of a lower alkoxy groupaa a carbamoyl group that may have a group(s) selected from the group consisting of a lower alkoxy group and a lower alkyl group, and a pyrrolidinyl group that may have an oxo group(s)),
(lxiii) an isoxazolidinyl group that may have an oxo group(s),
(lxiv) a dihydroindenyl group,
(lxv) an aryl lower alkoxy lower alkyl group,
(lxvi) a tetrahydropyranyl group,
(lxvii) an azetidinyl group that may have a group(s) selected from the group consisting of a lower alkanoyl group and an aroyl group,
(lxviii) an azetidinyl lower alkyl group that may have a group(s) selected from the group consisting of a lower alkanoyl group and aroyl group,
(lxix) a tetrazolyl group,
(lxx) an indolinyl group that may have an oxo group(s),
(lxxi) a triazolyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a lower alkylthio group,
(lxxii) an imidazolyl group that may have a carbamoyl group(s),
(lxxiii) an oxazolyl group that may have a lower alkyl group(s),
(lxxiv) an isothiazolyl group that may have a lower alkyl group(s),
(lxxv) a benzimidazolyl group,
(lxxvi) a dihydrobenzothiazolyl group that may have an oxo group(s),
(lxxvii) a thienyl group that may have a lower alkoxycarbonyl group(s), and
(lxxviii) an oxazolyl lower alkyl group that may have a lower alkyl group(s),
(29) an amino lower alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a halogen substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, an aryl group, an aryl lower alkyl group, an aroyl group, and an amino substituted alkyl group (that may have a lower alkyl group(s) as a substituent on the amino group) on the amino group,
(30) a lower alkyl group substituted with a carbamoyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a halogen substituted lower alkyl group,
(31) a thiocarbamoyl group that may have a lower alkyl group(s),
(32) a sulfamoyl group,
(33) an oxazolidinyl group that may have an oxo group(s),
(34) an imidazolidinyl group that may have a substituent(s) selected from the group consisting of an oxo group and a lower alkyl group,
(35) a pyrrolidinyl group that may have an oxo group(s),
(36) an imidazolyl group,
(37) a triazolyl group,
(38) an isoxazolyl group,
(39) a piperidyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, an arylsulfonyl group, an oxo group, a hydroxy group, and an amino group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, and lower alkanoylamino lower alkanoyl group,
(40) a piperidylcarbonyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group, a hydroxy group, a hydroxy lower alkyl group, a lower alkanoyl group, a carboxy lower alkyl group, a lower alkyl carbamoyl lower alkyl group, a carbamoyl group, a lower alkoxy group, a carboxy group, a lower alkoxycarbonyl group, an amino group (on which 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, and an aroyl group may be present), a piperidyl group (on which a group(s) selected from the group consisting of a lower alkanoyl group, a lower alkoxycarbonyl group, and an aroyl group may be present), a piperazinyl group (on which a lower alkyl group(s) may be present as a substituent), a 1,4-dioxa-8-azaspiro[4.5]decyl group, a morpholinyl group, a hexahydro-1,4-diazepinyl group (on which a lower alkyl group(s) may be present as a substituent), a pyridyl group, a pyridyloxy group, a pyridyl lower alkoxy group, a tetrahydroquinolyl group (on which an oxo group(s) may be present), a benzodioxolyl group, an aryl lower alkoxy group (that may have a group(s) selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group, and a halogen substituted lower alkoxy group on the aryl group), an aryl group (on which a group(s) selected from the group consisting of a halogen atom, a lower alkoxy group, and a hydroxy group may be present), an aryloxy group (that may have on the aryl group a group(s) selected from the group consisting of a cyano group, a halogen atom, lower alkyl group, a lower alkoxy group, and a halogen substituted lower alkyl group), an aryl lower alkyl group (that may have on the aryl group a group(s) selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group, and a halogen substituted lower alkyl group), and an aroyl group (that may have on the aryl group a group(s) selected from the group consisting of a halogen atom and a lower alkoxy group),
(41) a pyrrolidinylcarbonyl group that may have a group as a substituent, selected from the group consisting of a hydroxy lower alkyl group, a carbamoyl group, a hydroxy group, an amino group (that may have on the amino group a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, and an aroyl group), a morpholinyl lower alkyl group, a pyrrolidinyl lower alkyl group, a piperidyl lower alkyl group, a piperazinyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the piperazinyl group), an amino lower alkyl group (that may have a lower alkyl group(s) as a substituent on the amino group), an aryloxy group (that may have a halogen substituted lower alkoxy group(s) on the aryl group), an aryloxy lower alkyl group (that may have a halogen substituted lower alkoxy group(s) on the aryl group), and a tetrahydroquinolyl group (on which an oxo group(s) may be present),
(42) a piperazinylcarbonyl group that may have a group(s) as a substituent, selected from the group consisting of a lower alkyl group, a cyclo C3-C8 alkyl group, a lower alkanoyl group, a hydroxy lower alkyl group, a lower alkoxy lower alkyl group, a lower alkoxycarbonyl group, an amino lower alkyl group (that may have a lower alkyl group(s) as a substituent on the amino group), a piperidyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the piperidyl group), a morpholinyl lower alkyl group, a pyrrolidinyl lower alkyl group, a 1,3-dioxolanyl lower alkyl group, a tetrahydrofuryl lower alkyl group, a pyridyl lower alkyl group (that may have a phenyl group(s) as a substituent on the lower alkyl group), a imidazolyl lower alkyl group, a furyl lower alkyl group, a pyrrolidinylcarbonyl lower alkyl group, a piperidyl group (that may have a lower alkyl group(s) as a substituent, a pyridyl group (that may have on the pyridyl group a group(s) selected from the group consisting of a lower alkyl group, a cyano group, and a halogen substituted lower alkyl group as a substituent), a thieno[2,3-b]pyridyl group, an aryl group (on which a group(s) selected from the group consisting of a halogen atom and a lower alkyl group may be present), an aroyl group, a furyl carbonyl group, an aryl lower alkoxycarbonyl group, and an oxo group,
(43) a hexahydroazepinylcarbonyl group,
(44) a hexahydro-1,4-diazepinylcarbonyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group and a pyridyl group,
(45) a dihydropyrrolylcarbonyl group that may have a lower alkyl group(s),
(46) a thiomorpholinylcarbonyl group,
(47) a morpholinylcarbonyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a piperidyl lower alkyl group, and an aryl group,
(48) a thiazolidinyl carbonyl group that may have an aryl group(s) that may have a group(s) selected from the group consisting of a lower alkoxy group and a cyano group,
(49) an azabicyclo[3.2.2]nonylcarbonyl group,
(50) an 8-azabicyclo[3.2.1]octylcarbonyl group that may have a halogen substituted or unsubstituted aryloxy group(s),
(51) an indolinylcarbonyl group,
(52) a tetrahydroquinolylcarbonyl group,
(53) a tetrahydropyrido[3.4-b]indolylcarbonyl group,
(54) a morpholinyl lower alkyl group,
(55) a piperazinyl lower alkyl group that may have a lower alkyl group(s) on the piperazinyl group,
(56) a morpholinylcarbonyl lower alkyl group,
(57) a piperazinylcarbonyl lower alkyl group that may have a lower alkyl group(s) on the piperazinyl group,
(58) an oxo group,
(59) an amino lower alkoxy group (that may have a lower alkyl group(s) on the amino group),
(60) a lower alkoxy lower alkoxy group,
(61) a piperazinyl group that may have a group(s) selected from the group consisting of an oxo group, a lower alkyl group, a lower alkanoyl group, and a lower alkoxycarbonyl group,
(62) a morpholinyl group,
(63) a 1,3,8-triazaspiro[4.5]decanylcarbonyl group that may have a group(s) selected from the group consisting of an oxo group and an aryl group,
(64) a tetrahydropyridylcarbonyl group that may have a pyridyl group(s),
(65) an imidazolidinylcarbonyl group that may have a thioxo group(s), and
(66) a 1,4-dioxa-8-azaspiro[4.5]decanyl group.d
2 . The compound according to claim 1 , wherein
R 1 represents a heterocyclic group selected from the group consisting of (I) and (II) below: (I) a saturated or unsaturated heteromonocyclic group that has 1 to 2 hetero atoms selected from the group consisting of a nitrogen atom, oxygen atom and sulfur atom; and (II) a benzene fused heterocyclic group that has 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom, oxygen atom and sulfur atom and that is selected from the group consisting of (1) a tetrahydroquinoxalinyl group, (2) a tetrahydroquinazolinyl group, (3) a dihydroquinazolinyl group, (4) an indolinyl group, (5) an indolyl group, (6) an isoindolinyl group, (7) a benzimidazolinyl group, (8) a dihydrobenzimidazolyl group, (9) a tetrahydrobenzazepinyl group, (10) a tetrahydrobenzodiazepinyl group, (11) a hexahydrobenzazocinyl group, (12) a dihydrobenzoxazinyl group, (13) a dihydrobenzoxazolyl group, (14) a benzisoxazolyl group, (15) a benzoxadiazolyl group, (16) a tetrahydrobenzoxazepinyl group, (17) a dihydrobenzothiazinyl group, (18) a benzothiazolyl group, (19) a benzoxathiolyl group, (20) a chromenyl group, (21) a dihydrobenzofuryl group, (22) a carbazolyl group, (23) a dibenzofuryl group and (24) a quinoxalinyl group, wherein from 1 to 5 groups selected from the group consisting of the groups (1) to (66) below may be present as a substituent(s) on the heterocyclic group represented by R 1 : (1) a lower alkyl group, (2) a lower alkenyl group, (3) a halogen substituted lower alkyl group, (4) a lower alkoxy group, (5) a phenoxy group, (6) a lower alkylthio group, (7) a halogen substituted lower alkoxy group, (8) a hydroxy group, (9) a phenyl lower alkoxy group, (10) a hydroxy lower alkyl group, (11) a lower alkoxy lower alkyl group, (12) a halogen atom, (13) a cyano group, (14) a phenyl group, (15) a nitro group, (16) an amino group, (17) an amino group having 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a carbamoyl group, a lower alkyl carbamoyl group, an amino lower alkanoyl group, a lower alkanoylamino lower alkanoyl group, and a lower alkoxycarbonylamino lower alkanoyl group as a substituent(s), (18) a lower alkanoyl group, (19) a phenylsulfonyl group that may have a single lower alkyl group on the phenyl group, (20) a carboxy group, (21) a lower alkoxycarbonyl group, (22) a carboxy lower alkyl group, (23) a lower alkoxycarbonyl lower alkyl group, (24) a lower alkanoylamino lower alkanoyl group, (25) a carboxy lower alkenyl group, (26) a lower alkoxycarbonyl lower alkenyl group, (27) a carbamoyl lower alkenyl group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group and a lower alkyl group substituted with 1 to 3 halogen atoms as a substituent(s), (28) a carbamoyl group that may have 1 to 2 groups selected from the group consisting of the groups (i) to (lxxviii) below as a substituent(s):
(i) a lower alkyl group,
(ii) a lower alkoxy group,
(iii) a hydroxy lower alkyl group,
(iv) a lower alkoxy lower alkyl group,
(v) an phenoxy lower alkyl group,
(vi) a halogen substituted lower alkyl group,
(vii) an amino lower alkyl group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group, a tower alkanoyl group, a benzoyl group, and a carbamoyl group,
(viii) a cyclo C3-C8 alkyl group that may have 1 to 3 groups selected from the group consisting of a lower alkyl group, a hydroxy group, a lower alkoxycarbonyl group, and a phenyl lower alkoxy group as a substituent(s),
(ix) a cyclo C3-C8 alkyl substituted lower alkyl group,
(x) a lower alkenyl group,
(xi) a lower alkyl group having 1 to 2 carbamoyl groups that may have 1 to 2 groups as a substituent(s) selected from the group consisting of a lower alkyl group, a phenyl group that may have a single lower alkyl group, and a phenyl group that may have a single lower alkoxy group,
(xii) a lower alkyl group having 1 to 2 lower alkoxy carbonyl groups,
(xiii) a furyl lower alkyl group (that may have 1 to 2 lower alkyl groups as a substituent(s) on the furyl group),
(xiv) a tetrahydrofuryl lower alkyl group,
(xv) a 1,3-dioxolanyl lower alkyl group,
(xvi) a tetrahydropyranyl lower alkyl group,
(xvii) a pyrrolyl lower alkyl group (that may have 1 to 2 lower alkyl groups on the pyrrolyl group as a substituent(s)),
(xviii) a lower alkyl group substituted with a dihydropyrazolyl group that may have a single oxo group,
(xix) a pyrazolyl lower alkyl group (that may have 1 to 3 lower alkyl groups as a substituent(s) on the pyrazolyl group),
(xx) an imidazolyl lower alkyl group,
(xxi) a pyridyl lower alkyl group,
(xxii) a pyrazinyl lower alkyl group (that may have 1 to 3 (preferably 1) lower alkyl groups as a substituent(s) on the pyrazinyl group),
(xxiii) a pyrrolidinyl lower alkyl group (that may have 1 to 2 groups selected from the group consisting of an oxo group and a lower alkyl group as a substituent(s) on the pyrrolidinyl group),
(xxiv) a piperidyl lower alkyl group (that may have 1 to 3 groups selected from the group consisting of a benzoyl group and a lower alkanoyl group as a substituent(s) on the piperidyl group),
(xxv) a piperazinyl lower alkyl group (that may have 1 to 3 lower alkyl groups as a substituent(s) on the piperazinyl group),
(xxvi) a morpholinyl lower alkyl group,
(xxvii) a thienyl lower alkyl group (that may have 1 to 3 lower alkyl groups as a substituent(s) on the thienyl group),
(xxviii) a thiazolyl lower alkyl group,
(xxix) a dihydrobenzofuryl lower alkyl group,
(xxx) a benzopyranyl lower alkyl group (that may have a single oxo group as a substituent on the benzopyranyl group),
(xxxi) a benzimidazolyl lower alkyl group,
(xxxii) an indolyl lower alkyl group that may have 1 to 3 lower alkoxycarbonyl groups on the lower alkyl group,
(xxxiii) an imidazolyl lower alkyl group that has 1 to 3 substituents selected from the group consisting of a carbamoyl group and a lower alkoxycarbonyl group, on the lower alkyl group,
(xxxiv) a pyridyl group that may have 1 to 3 groups selected from the group consisting of a lower alkyl group, a lower alkoxy group, and a lower alkylthio lower alkyl group as a substituent(s),
(xxxv) a pyrrolidinyl group that may have 1 to 3 groups selected from the group consisting of a lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, and a benzoyl group as a substituent(s),
(xxxvi) a piperidyl group that may have 1 to 3 groups selected from the group consisting of a lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, and a benzoyl group (that may have 1 to 3 groups selected from the group consisting of a lower alkyl group and a halogen atom as a substituent(s) on the phenyl group),
(xxxvii) a tetrahydrofuryl group that may have a single oxo group
(xxxviii) a hexahydroazepinyl group that may have a single oxo group,
(xxxix) a pyrazolyl group that may have 1 to 3 groups selected from the group consisting of a lower alkyl group, a phenyl group, and a furyl group as a substituent(s),
(xl) a thiazolyl group,
(xli) a thiadiazolyl group that may have 1 to 3 lower alkyl groups,
(xlii) an isoxazolyl group that may have 1 to 3 lower alkyl groups,
(xliii) an indazolyl group,
(xliv) an indolyl group,
(xlv) a tetrahydrobenzothiazolyl group,
(xlvi) a tetrahydroquinolyl group that may have 1 to 3 groups selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen atom, and an oxo group as a substituent(s),
(xlvii) a quinolyl group that may have 1 to 3 lower alkyl groups,
(xlviii) a benzodioxolyl lower alkyl group,
(xlix) a phenyl group or naphthyl group that may have 1 to 3 groups as a substituent(s), selected from the group consisting of a halogen atom; a lower alkyl group; a lower alkoxy group; a halogen substituted lower alkyl group; a halogen substituted lower alkoxy group; a lower alkenyl group; an amino group that may have 1 to 2 groups selected from the group consisting of a lower alkanoyl group, a lower alkyl sulfonyl group, a lower alkyl group, and an aryl group; a sulfamoyl group; a lower alkylthio group; a lower alkanoyl group; a lower alkoxycarbonyl group; a pyrrolyl group; a lower alkynyl group; a cyano group; a nitro group; a phenyloxy group; a phenyl lower alkoxy group; a hydroxy group; a hydroxy lower alkyl group; a carbamoyl group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group and a phenyl group; a pyrazolyl group; a pyrrolidinyl group that may have a single oxo group; an oxazolyl group; an imidazolyl group that may have 1 to 3 lower alkyl groups; a dihydrofuryl group that may have a single oxo group; a thiazolidinyl lower alkyl group that may have two oxo groups; imidazolyl lower alkanoyl group; and piperidinylcarbonyl group,
(l) a cyano lower alkyl group,
(li) a dihydroquinolyl group that may have 1 to 3 group(s) selected from the group consisting of a lower alkyl group and an oxo group,
(lii) a halogen substituted lower alkylamino group,
(liii) a lower alkylthio lower alkyl group,
(liv) an amidino group that may have a lower alkyl group,
(lv) an amidino lower alkyl group,
(lvi) a lower alkenyloxy lower alkyl group,
(lvii) a phenylamino group that may have 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen substituted lower alkyl group, and a halogen substituted lower alkoxy group on the phenyl group,
(lviii) a phenyl lower alkenyl group,
(lix) a pyridylamino group that may have 1 to 3 lower alkyl groups,
(lx) a phenyl lower alkyl group (that may have as a substituent(s) on the phenyl group and/or the lower alkyl group 1 to 3 groups selected from the group consisting of a halogen atom, a lower alkyl group, a halogen substituted lower alkyl group, a halogen substituted lower alkoxy group, a lower alkoxy group, carbamoyl group, and a lower alkoxycarbonyl group),
(lxi) a lower alkynyl group,
(lxii) a phenyloxy lower alkyl group (that may have 1 to 3 groups selected from the group consisting of a lower alkoxy group, N-lower alkoxy-N-lower alkylcarbamoyl group, and oxopyrrolidinyl group as a substituent(s) on the phenyl group),
(lxiii) an isoxazolidinyl group that may have a single oxo group,
(lxiv) a dihydroindenyl group,
(lxv) a phenyl lower alkoxy lower alkyl group,
(lxvi) a tetrahydropyranyl group,
(lxvii) an azetidinyl group that may have 1 to 3 groups selected from the group consisting of a lower alkanoyl group and benzoyl group,
(lxviii) an azetidinyl lower alkyl group that may have 1 to 3 groups selected from the group consisting of a lower alkanoyl group and benzoyl group,
(lxix) a tetrazolyl group,
(lxx) an indolinyl group that may have a single oxo group,
(lxxi) a triazolyl group that may have 1 to 3 groups selected from the group consisting of a lower alkyl group and a lower alkylthio group,
(lxxii) an imidazolyl group that may have 1 to 3 carbamoyl groups,
(lxxiii) an oxazolyl group that may have 1 to 3 lower alkyl groups,
(lxxiv) an isothiazolyl group that may have 1 to 3 lower alkyl groups,
(lxxv) a benzimidazolyl group,
(lxxvi) a dihydrobenzothiazolyl group that may have a single oxo group,
(lxxvii) a thienyl group that may have 1 to 3 lower alkoxycarbonyl groups, and
(lxxviii) an oxazolyl lower alkyl group that may have 1 to 3 lower alkyl groups,
(29) an amino lower alkyl group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group, a halogen substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, a phenyl group, a phenyl lower alkyl group, a benzoyl group and an amino substituted alkyl group (that may have 1 to 2 lower alkyl groups as a substituent(s) on the amino group), on the amino group, (30) a lower alkyl group substituted with a single carbamoyl group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group and a halogen substituted lower alkyl group, (31) a thiocarbamoyl group that may have 1 to 2 lower alkyl groups, (32) a sulfamoyl group, (33) an oxazolidinyl group that may have a single oxo group, (34) an imidazolidinyl group that may have 1 to 2 substituents selected from the group consisting of an oxo group and a lower alkyl group, (35) a pyrrolidinyl group that may have a single oxo group, (36) an imidazolyl group, (37) a triazolyl group, (38) an isoxazolyl group, (39) a piperidyl group that may have 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkylphenylsulfonyl group, an oxo group, a hydroxy group, and an amino group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, and a lower alkanoylamino lower alkanoyl group, (40) a piperidylcarbonyl group that may have 1 to 3 substituents selected from the group consisting of a lower alkyl group, a hydroxy group, a hydroxy lower alkyl group, a lower alkanoyl group, a carboxy lower alkyl group, a lower alkyl carbamoyl lower alkyl group, a carbamoyl group, a lower alkoxy group, a carboxy group, a lower alkoxycarbonyl group, an amino group (on which 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, and a benzoyl group may be present), a piperidyl group (on which 1 to 3 groups selected from the group consisting of a lower alkanoyl group, a lower alkoxycarbonyl group, and a benzoyl group may be present), a piperazinyl group (on which 1 to 3 lower alkyl groups may be present as a substituent(s)), a 1,4-dioxa-8-azaspiro[4.5]decyl group, a morpholinyl group, a hexahydro-1,4-diazepynyl group (on which a single lower alkyl group may be present as a substituent), a pyridyl group, a pyridyloxy group, a pyridyl lower alkoxy group, a tetrahydroquinolyl group (on which a single oxo group may be present), a benzodioxolyl group, a phenyl lower alkoxy group (that may have on the phenyl group 1 to 3 groups selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group, and a halogen substituted lower alkoxy group), a phenyl group (on which 1 to 3 groups selected from the group consisting of a halogen atom, a lower alkoxy group, and a hydroxy group may be present), a phenyloxy group (that may have on the phenyl group 1 to 3 groups selected from the group consisting of a cyano group, a halogen atom, a lower alkyl group, a lower alkoxy group, and a halogen substituted lower alkyl group), a phenyl lower alkyl group (on the phenyl group, 1 to 3 groups selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group, and a halogen substituted lower alkyl group may be present), and a benzoyl group (that may have 1 to 3 groups selected from the group consisting of a halogen atom and a lower alkoxy group on the phenyl group), (41) a pyrrolidinylcarbonyl group that may have 1 to 3 groups as a substituent(s) selected from the group consisting of a hydroxy lower alkyl group, a carbamoyl group, a hydroxy group, an amino group (that may have 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group, and a benzoyl group on the amino group), a morpholinyl lower alkyl group, a pyrrolidinyl lower alkyl group, a piperidyl lower alkyl group, a piperazinyl lower alkyl group (that may have a single lower alkyl group as a substituent on the piperazinyl group), an amino lower alkyl group (that may have 1 to 2 lower alkyl groups may be present as a substituent on the amino group), phenyloxy group (that may have 1 to 3 halogen substituted lower alkoxy groups on the phenyl group), a phenyloxy lower alkyl group (that may have 1 to 3 halogen substituted lower alkoxy groups on the phenyl group), and a tetrahydroquinolyl group (on which an oxo group may be present), (42) a piperazinylcarbonyl group that may have 1 to 3 groups as a substituents) selected from the group consisting of a lower alkyl group, a cyclo C3-C8 alkyl group, a lower alkanoyl group, a hydroxy lower, alkyl group, a lower alkoxy lower alkyl group, a lower alkoxycarbonyl group, an amino lower alkyl group (that may have 1 to 2 lower alkyl groups as a substituent(s) on the amino group), a piperidyl lower alkyl group (that may have 1 to 2 lower alkyl groups as a substituents) on the piperidyl group), a morpholinyl lower alkyl group, a pyrrolidinyl lower alkyl group, a 1,3-dioxoranyl lower alkyl group, a tetrahydrofuryl lower alkyl group, a pyridyl lower alkyl group (that may have 1 to 2 phenyl groups as a substituent(s) on the lower alkyl group), an imidazolyl lower alkyl group, a furyl lower alkyl group, a pyrrolidinylcarbonyl lower alkyl group, a piperidyl group that may have 1 to 2 lower alkyl groups as a substituent(s)), a pyridyl group (that may have 1 to 3 groups selected from the group consisting of a lower alkyl group, a cyano group, and a halogen substituted lower alkyl group as a substituent(s) on the pyridyl group), a thieno[2,3-b]pyridyl group, a phenyl group (on which 1 to 3 groups selected from the group consisting of a halogen atom and a lower alkyl group may be present), a benzoyl group, a furyl carbonyl group, a phenyl lower alkoxycarbonyl group, and an oxo group, (43) a hexahydroazepinylcarbonyl group, (44) a hexahydro-1,4-diazepinylcarbonyl group that may have 1 to 3 substituents selected from the group consisting of a lower alkyl group and a pyridyl group, (45) a dihydropyrrolylcarbonyl group that may have 1 to 3 lower alkyl groups, (46) a thiomorpholinylcarbonyl group, (47) a morpholinylcarbonyl group that may have 1 to 3 groups selected from the group consisting of a lower alkyl group, a piperidyl lower alkyl group, and a phenyl group, (48) a thiazolidinyl cabonyl group that may have 1 to 3 phenyl groups that may have 1 to 3 groups selected from the group consisting of a lower alkoxy group and a cyano group, (49) an azabicyclo[3.2.2]nonylcarbonyl group, (50) an 8-azabicyclo[3.2.1]octylcarbonyl group that may have 1 to 3 halogen substituted or unsubstituted phenyloxy groups, (51) an indolinylcarbonyl group, (52) a tetrahydroquinolylcarbonyl group, (53) a tetrahydropyrido[3.4-b]indolylcarbonyl group, (54) a morpholinyl lower alkyl group, (55) a piperazinyl lower alkyl group that may have 1 to 3 lower alkyl groups on the piperazinyl group, (56) a morpholinylcarbonyl lower alkyl group, (57) a piperazinylcarbonyl lower alkyl group that may have 1 to 3 lower alkyl groups on the piperazinyl group, (58) an oxo group, (59) an amino lower alkoxy group (that may have 1 to 2 lower alkyl groups on the amino group), (60) a lower alkoxy lower alkoxy group, (61) a piperazinyl group that may have 1 to 3 groups selected from the group consisting of an oxo group, a lower alkyl group, a lower alkanoyl group and a lower alkoxycarbonyl group, (62) a morpholinyl group, (63) a 1,3,8-triazaspiro[4.5]decanylcarbonyl group that may have 1 to 3 groups selected from the group consisting of an oxo group and a phenyl group, (64) a tetrahydropyridylcarbonyl group that may have 1 to 3 pyridyl groups, (65) an imidazolidinylcarbonyl group that may have a single thioxo group, and (66) a 1,4-dioxa-8-azaspiro[4.5]decanyl group.
3 . The compound according to claim 1 , wherein A represents a lower alkylene group.
4 - 22 . (canceled)
23 . A process for producing a heterocyclic compound represented by the formula (1):
or a salt thereof, where R 2 represents a hydrogen atom or a lower alkyl group;
A represents a lower alkylene group or a lower alkenylene group; and
R 1 represents a cyclo C3-C8 alkyl group, an aromatic group or a heterocyclic group selected from the group consisting of (I) to (IV) below:
(I) cyclo C3-C8 alkyl group;
(II) an aromatic group selected from a phenyl group, a naphthyl group, a dihydroindenyl group, and a tetrahydronaphthyl group;
(III) a saturated or unsaturated heteromonocyclic group having 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom, and oxygen atom and a sulfur atom; and
(IV) a benzene fused heterocyclic group that has 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom and that is selected from the group consisting of (1) a tetrahydroquinoxalinyl group, (2) a tetrahydroquinazolinyl group, (3) a dihydroquinazolinyl group, (4) an indolinyl group, (5) an indolyl group, (6) an isoindolinyl group, (7) a benzimidazolyl group, (8) a dihydrobenzimidazolyl group, (9) a tetrahydrobenzazepinyl group, (10) a tetrahydrobenzodiazepinyl group, (11) a hexahydrobenzazocinyl group, (12) a dihydrobenzoxazinyl group, (13) a dihydrobenzoxazolyl group, (14) a benzisoxazolyl group, (15) a benzoxadiazolyl group, (16) a tetrahydrobenzoxazepinyl group, (17) a dihydrobenzothiazinyl group, (18) a benzothiazolyl group, (19) a benzoxathiolyl group, (20) a chromenyl group, (21) a dihydrobenzofuryl group, (22) a carbazolyl group, (23) a dibenzofuryl group and (24) a quinoxalinyl group
wherein at least one group selected from the group consisting of the groups (1) to (66) below may be present as a substituent on the cyclo C3-C8 alkyl group, the aromatic group, and the heterocyclic group represented by R 1 :
(1) a lower alkyl group,
(2) a lower alkenyl group,
(3) a halogen substituted lower alkyl group,
(4) a lower alkoxy group,
(5) an aryloxy group,
(6) a lower alkylthio group,
(7) a halogen substituted lower alkoxy group,
(8) a hydroxy group,
(9) a protected hydroxy group,
(10) a hydroxy lower alkyl group,
(11) a protected hydroxy lower alkyl group,
(12) a halogen atom,
(13) a cyano group,
(14) an aryl group,
(15) a nitro group,
(16) an amino group,
(17) an amino group having a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a carbamoyl group, a lower alkyl carbamoyl group, an amino lower alkanoyl group, a lower alkanoylamino lower alkanoyl group, and a lower alkoxy carbonylamino lower alkanoyl group as a substituent,
(18) a lower alkanoyl group,
(19) an arylsulfonyl group that may have a lower alkyl group(s) on the aryl group,
(20) a carboxy group,
(21) a lower alkoxycarbonyl group,
(22) a carboxy lower alkyl group,
(23) a lower alkoxycarbonyl lower alkyl group,
(24) a lower alkanoylamino lower alkanoyl group,
(25) a carboxy lower alkenyl group,
(26) a lower alkoxycarbonyl lower alkenyl group,
(27) a carbamoyl lower alkenyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a halogen substituted lower alkyl group as a substituent.,
(28) a carbamoyl group that may have a group(s) selected from the aroup consisting of the groups (i) to (lxxviii) below as a substituent:
(i) a lower alkyl group,
(ii) a lower alkoxy group,
(iii) a hydroxy lower alkyl group,
(iv) a lower alkoxy lower alkyl group,
(v) an aryloxy lower alkyl group,
(vi) a halogen substituted lower alkyl group,
(vii) an amino lower alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, an aroyl group, and a carbamoyl group,
(viii) a cyclo C3-C8 alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a hydroxy group, a lower alkoxycarbonyl group, and a phenyl lower alkoxy group as a substituent,
(ix) a cyclo C3-C8 alkyl substituted lower alkyl group,
(x) a lower alkenyl group.,
(xi) a carbamoyl lower alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, phenyl group that may have a lower alkyl group(s), and a phenyl group(s) that may have a lower alkoxy group(s) as a substituent,
(xii) a lower alkoxycarbonyl lower alkyl group,
(xiii) a furyl lower alkyl group (that may have a lower alkyl group(s) as a substituent) on the furyl group,
(xiv) a tetrahydrofuryl lower alkyl group,
(xv) a 1,3-dioxolanyl lower alkyl group,
(xvi) a tetrahydropyranyl lower alkyl group,
(xvii) a pyrrolyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the pyrrolyl group),
(xviii) a lower alkyl group substituted with a dihydropyrazolyl group that may have an oxo group(s),
(xix) a pyrazolyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the pyrazolyl group),
(xx) an imidazolyl lower alkyl group,
(xxi) a pyridyl lower alkyl group,
(xxii) a pyrazinyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the pyrazinyl group),
(xxiii) a pyrrolidinyl lower alkyl group (that may have a group(s) selected from the group consisting of an oxo group(s) and a lower alkyl group as a substituent on the pyrrolidinyl group),
(xxiv) a piperidyl lower alkyl group (that may have a group(s) selected from the group consisting of a benzoyl group and a lower alkanoyl group as a substituent on the piperidyl group),
(xxv) a piperazinyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the piperazinyl group),
(xxvi) a morpholinyl lower alkyl group,
(xxvii) a thienyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the thienyl group),
(xxviii) a thiazolyl lower alkyl group,
(xxix) a dihydrobenzofuryl lower alkyl group,
(xxx) a benzopyranyl lower alkyl group (that may have an oxo group(s) as a substituent on the benzopyranyl group,
(xxxi) a benzimidazolyl lower alkyl group,
(xxxii) an indolyl lower alkyl group that may have a lower alkoxycarbonyl group(s) on the lower alkyl group,
(xxxiii) an imidazolyl lower alkyl group that has a substituent(s) selected from the group consisting of a carbamoyl group and a lower alkoxycarbonyl group on the lower alkyl group,
(xxxiv) a pridyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxy group, and a lower alkylthio lower alkyl group as a substituent,
(xxxv) a pyrrolidinyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, and an aroyl group as a substituent,
(xxxvi) a piperidyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, and an aroyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a halogen atom as a substituent,
(xxxvii) a tetrahydrofuryl group that may have an oxo group(s),
(xxxviii) a hexahydroazepinyl group that may have an oxo group(s),
(xxxix) a pyrazolyl group that may have a group(s) selected from the group consisting of a lower alkyl group, an aryl group, and a furl group as a substituent,
(xl) a thiazolyl group,
(xli) a thiadiazolyl group that may have a lower alkyl group(s),
(xlii) an isoxazolyl group that may have a lower alkyl group(s),
(xliii) an indazolyl group,
(xliv) an indolyl group,
(xlv) a tetrahydrobenzothiazolyl group,
(xlvi) a tetrahydroquinolyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen atom, and an oxo group as a substituent,
(xlvii) a quinolyl group that may have a lower alkyl group(s),
(xlviii) a benzodioxolyl lower alkyl group,
(xlix) an aryl group that may have a group(s) as a substituent, selected from the group consisting of a halogen atom; a lower alkyl group; a lower alkoxy group; a halogen substituted lower alkyl group; a halogen substituted lower alkoxy group; a lower alkenyl group: an amino group that may have a group(s) selected from the group consisting of a lower alkanoyl group, a lower alkyl sulfonyl group, a lower alkyl group, and an aryl group; a sulfamoyl group; a lower alkylthio group; a lower alkanoyl group; a lower alkoxycarbonyl group; a pyrrolyl group; a lower alkynyl group; a cyano group; a nitro group; an aryloxy group; an aryl lower alkoxy group; a hydroxy group; a hydroxy lower alkyl group; a carbamoyl group that may have a group(s) selected from the group consisting of a lower alkyl group and an aryl group; a pyrazolyl group; a pyrrolidinyl group that may have an oxo group(s); an oxazolyl group; an imidazolyl group that may have a lower alkyl group(s); a dihydrofuryl group that may have an oxo group(s); a thiazolidinyl lower alkyl group that may have an oxo group(s); an imidazolyl lower alkanoyl group; and a piperidinylcarbonyl group,
(l) a cyano lower alkyl group,
(li) a dihydroquinolyl group that may have a group(s) selected from the group consisting of a lower alkyl group and an oxo group,
(lii) a halogen substituted lower alkylamino group,
(liii) a lower alkylthio lower alkyl group,
(liv) an amidino group that may have a lower alkyl group(s),
(lv) an amidino lower alkyl group,
(lvi) a lower alkenyloxy lower alkyl group,
(lvii) an arylamino group that may have a substituent(s) selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen substituted lower alkyl group, and a halogen substituted lower alkoxy group, on the aryl group,
(lviii) an aryl lower alkenyl group,
(lix) a pyridylamino group that may have a lower alkyl group(s),
(lx) an aryl lower alkyl group (that may have on the aryl group and/or the lower alkyl group a group(s) selected from the group consisting of a halogen atom, a lower alkyl group, a halogen substituted lower alkyl group, a halogen substituted lower alkoxy group, a lower alkoxy group, a carbamoyl group, and a lower alkoxycarbonyl group as a substituent),
(lxi) a lower alkynyl group.,
(lxii) an aryloxy lower alkyl group (that may have as a substituent on the aryl group a group(s) selected from the group consisting of a lower alkoxy group, a carbamoyl group that may have a group(s) selected from the group consisting of a lower alkoxy group and a lower alkyl group, and a pyrrolidinyl group that may have an oxo group(s)),
(lxiii) an isoxazolidinyl group that may have an oxo group(s),
(lxiv) a dihydroindenyl group,
(lxv) an aryl lower alkoxy lower alkyl group,
(lxvi) a tetrahydropyranyl group,
(lxvii) an azetidinyl group that may have a group(s) selected from the group consisting of a lower alkanoyl group and an aroyl group,
(lxviii) an azetidinyl lower alkyl group that may have a group(s) selected from the group consisting of a lower alkanoyl group and aroyl group,
(lxix) a tetrazolyl group,
(lxx) an indolinyl group that may have an oxo group(s),
(lxxi) a triazolyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a lower alkylthio group,
(lxxii) an imidazolyl group that may have a carbamoyl group(s),
(lxxiii) an oxazolyl group that may have a lower alkyl group(s),
(lxxiv) an isothiazolyl group that may have a lower alkyl group(s),
(lxxv) a benzimidazolyl group,
(lxxvi) a dihydrobenzothiazolyl group that may have an oxo group(s),
(lxxvii) a thienyl group that may have a lower alkoxycarbonyl group(s), and
(lxxviii) an oxazolyl lower alkyl group that may have a lower alkyl group(s),
(29) an amino lower alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a halogen substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, an aryl group, an aryl lower alkyl group an aroyl group, and an amino substituted alkyl group (that may have a lower alkyl group(s) as a substituent on the amino group) on the amino group,
(30) a lower alkyl group substituted with a carbamoyl group that may have a group(s) selected from the group consisting of a lower alkyl aomu and a haloen substituted lower alkyl group,
(31) a thiocarbamoyl group that may have a lower alkyl group(s),
(32) a sulfamoyl group,
(33) an oxazolidinyl group that may have an oxo group(s),
(34) an imidazolidinyl group that may have a substituent(s) selected from the group consisting of an oxo group and a lower alkyl group,
(35) a pyrrolidinyl group that may have an oxo group(s).,
(36) an imidazolyl group,
(37) a triazolyl group,
(38) an isoxazolyl group,
(39) a piperidyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, an arylsulfonyl group, an oxo group, a hydroxy group, and an amino group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, and lower alkanoylamino lower alkanoyl group,
(40) a piperidylcarbonyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group, a hydroxy group, a hydroxy lower alkyl group, a lower alkanoyl group, a carboxy lower alkyl group, a lower alkyl carbamoyl lower alkyl group, a carbamoyl group, a lower alkoxy group, a carboxy group, a lower alkoxycarbonyl group, an amino group (on which 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, and an aroyl group may be present), a piperidyl group (on which a group(s) selected from the group consisting of a lower alkanoyl group, a lower alkoxycarbonyl group, and an aroyl group may be present), a piperazinyl group (on which a lower alkyl group(s) may be present as a substituent), a 1,4-dioxa-8-azaspiro[4.5]decyl group, a morpholinyl group, a hexahydro-1,4-diazepinyl group (on which a lower alkyl group(s) may be present as a substituent), a pyridyl group, a pyridyloxy group, a pyridyl lower alkoxy group, a tetrahydroquinolyl group (on which an oxo group(s) may be present), a benzodioxolyl group, an aryl lower alkoxy group (that may have a group(s) selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group, and a halogen substituted lower alkoxy group on the aryl group), an aryl group (on which a group(s) selected from the group consisting of a halogen atom, a lower alkoxy group, and a hydroxy group may be present), an aryloxy group (that may have on the aryl group a group(s) selected from the group consisting of a cyano group, a halogen atom, lower alkyl group, a lower alkoxy group, and a halogen substituted lower alkyl group), an aryl lower alkyl group (that may have on the aryl group a group(s) selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group, and a halogen substituted lower alkyl group), and an aroyl group (that may have on the aryl group a group(s) selected from the group consisting of a halogen atom and a lower alkoxy group),
(41) a pyrrolidinylcarbonyl group that may have a group as a substituent, selected from the group consisting of a hydroxy lower alkyl group, a carbamoyl group, a hydroxy group, an amino group (that may have on the amino group a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, and an aroyl group), a morpholinyl lower alkyl group, a pyrrolidinyl lower alkyl group, a piperidyl lower alkyl group, a piperazinyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the piperazinyl group), an amino lower alkyl group (that may have a lower alkyl group(s) as a substituent on the amino group), an aryloxy group (that may have a halogen substituted lower alkoxy group(s) on the aryl group), an aryloxy lower alkyl group (that may have a halogen substituted lower alkoxy group(s) on the aryl group), and a tetrahydroquinolyl group (on which an oxo group(s) may be present),
(42) a piperazinylcarbonyl group that may have a group(s) as a substituent, selected from the group consisting of a lower alkyl group, a cyclo C3-C8 alkyl group, a lower alkanoyl group, a hydroxy lower alkyl group, a lower alkoxy lower alkyl group, a lower alkoxycarbonyl group, an amino lower alkyl group (that may have a lower alkyl group(s) as a substituent on the amino group), a piperidyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the piperidyl group), a morpholinyl lower alkyl group, a pyrrolidinyl lower alkyl group, a 1,3-dioxolanyl lower alkyl group, a tetrahydrofuryl lower alkyl group, a pyridyl lower alkyl group (that may have a phenyl group(s) as a substituent on the lower alkyl group), a imidazolyl lower alkyl group, a furyl lower alkyl group, a pyrrolidinylcarbonyl lower alkyl group, a piperidyl group (that may have a lower alkyl group(s) as a substituent), pyridyl group (that may have on the pyridyl group a group(s) selected from the group consisting of a lower alkyl group, a cyano group, and a halogen substituted lower alkyl group as a substituent), a thieno[2,3-b]pyridyl group, an aryl group (on which a group(s) selected from the group consisting of a halogen atom and a lower alkyl group may be present), an aroyl group, a furyl carbonyl group, an aryl lower alkoxycarbonyl group, and an oxo group,
(43) a hexahydroazepinylcarbonyl group,
(44) a hexahydro-1,4-diazepinylcarbonyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group and a pyridyl group,
(45) a dihydropyrrolylcarbonyl group that may have a lower alkyl group(s),
(46) a thiomorpholinylcarbonyl group,
(47) a morpholinylcarbonyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a piperidyl lower alkyl group, and an aryl group,
(48) a thiazolidinyl carbonyl group that may have an aryl group(s) that may have a group(s) selected from the arouD consisting of a lower alkoxy group and a cyano group,
(49) an azabicyclo[3.2.2]nonylcarbonyl group,
(50) an 8-azabicyclo[3.2.1]octylcarbonyl group that may have a halogen substituted or unsubstituted aryloxy group(s).,
(51) an indolinylcarbonyl group.,
(52) a tetrahydroquinolylcarbonyl group,
(53) a tetrahydropyrido[3.4-b]indolylcarbonyl group,
(54) a morpholinyl lower alkyl group,
(55) a piperazinyl lower alkyl group that may have a lower alkyl group(s) on the piperazinyl group,
(56) a morpholinylcarbonyl lower alkyl group,
(57) a piperazinylcarbonyl lower alkyl group that may have a lower alkyl group(s) on the piperazinyl group,
(58) an oxo group,
(59) an amino lower alkoxy group (that may have a lower alkyl group(s) on the amino group),
(60) a lower alkoxy lower alkoxy group.,
(61) a piperazinyl group that may have a group(s) selected from the group consisting of an oxo group, a lower alkyl group, a lower alkanoyl group, and a lower alkoxycarbonyl group,
(62) a morpholinyl group,
(63) a 1,3,8-tnazaspiro[4,5-]decanylcarbonyl group that may have a group(s) selected from the group consisting of an oxo group and an aryl group,
(64) a tetrahydropyridylcarbonyl group that may have a pyridyl group(s).,
(65) an imidazolidinylcarbonyl group that may have a thioxo group(s), and
(66) a 1,4-dioxa-8-azaspiro[4.5]decanyl group;
said process comprising reacting a compound represented by the formula:
R 1 —O-A-X 1
wherein R 1 and A are the same as defined above, and X 1 represents a halogen atom or a group which causes the same substitution reaction as a halogen atom or a salt thereof with a compound represented by the formula:
wherein R 2 is the same as defined above) or a salt thereof.
24 . A pharmaceutical composition comprising a heterocyclic compound of formula (1) or a salt thereof according to any one of claims 1 - 3 , and a pharmaceutically acceptable carrier for treating a central nervous system disorder selected from the group consisting of schizophrenia; refractory, intractable, or chronic schizophrenia; bipolar I type disorder; bipolar II type disorder, depression; endogenous depression; major depression; melancholy and refractory depression; autism disorder (autism); and attention-deficit/hyperactivity disorder.
25 . A process for producing a pharmaceutical composition comprising mixing a heterocyclic compound of formula (1) or a salt thereof according to any one of claims 1 - 3 with a pharmaceutically acceptable carrier.
26 . A method of treating a central nervous system disorder selected from the group consisting of schizophrenia; bipolar I type disorder; bipolar II type disorder, depression; endogenous depression; major depression; melancholy and refractory depression; autism disorder (autism); and attention-deficit/hyperactivity disorder comprising administering to a human or an animal a heterocyclic compound of formula (1):
where R 2 represents a hydrogen atom or a lower alkyl group;
A represents a lower alkylene group or a lower alkenylene group; and
R 1 represents a cyclo C3-C8 alkyl group, an aromatic group or a heterocyclic group selected from the group consisting of (I) to (IV) below:
(I) a cyclo C3-C8 alkyl group;
(II) an aromatic group selected from a phenyl group, a naphthyl group, a dihydroindenyl group, and a tetrahydronaphthyl group;
(III) a saturated or unsaturated heteromonocyclic group having 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom; and
(IV) a benzene fused heterocyclic group selected from the group consisting of (1) a tetrahydroquinoxalinyl group, (2) a tetrahydroquinazolinyl group, (3) a dihydroquinazolinyl group, (4) an indolinyl group, (5) an indolyl group, (6) an isoindolinyl group, (7) a benzimidazolyl group, (8) a dihydrobenzimidazolyl group, (9) a tetrahydrobenzazepinyl group, (10) a tetrahydrobenzodiazepinyl group, (11) a hexahydrobenzazocinyl group, (12) a dihydrobenzoxazinyl group, (13) a dihydrobenzoxazolyl group, (14) a benzisoxazolyl group, (15) a benzoxadiazolyl group, (16) a tetrahydrobenzoxazepinyl group, (17) a dihydrobenzothiazinyl group, (18) a benzothiazolyl group, (19) a benzoxathiolyl group, (20) a chromenyl group, (21) a dihydrobenzofuryl group, (22) a carbazolyl group, (23) a dibenzofuryl group, and (24) a quinoxalinyl group,
wherein at least one group selected from the group consisting of the groups (1) to (66) below may be present as a substituent on the cyclo C3-C8 alkyl group, the aromatic group, and the heterocyclic group represented by R 1 :
(1) a lower alkyl group,
(2) a lower alkenyl group,
(3) a halogen substituted lower alkyl group,
(4) a lower alkoxy group,
(5) an aryloxy group,
(6) a lower alkylthio group,
(7) a halogen substituted lower alkoxy group,
(8) a hydroxy group,
(9) a protected hydroxy group,
(10) a hydroxy lower alkyl group,
(11) a protected hydroxy lower alkyl group,
(12) a halogen atom,
(13) a cyano group,
(14) an aryl group,
(15) a nitro group,
(16) an amino group,
(17) an amino group having a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a carbamoyl group, a lower alkyl carbamoyl group, an amino lower alkanoyl group, a lower alkanoylamino lower alkanoyl group, and a lower alkoxy carbonylamino lower alkanoyl group as a substituent,
(18) a lower alkanoyl group,
(19) an arylsulfonyl group that may have a lower alkyl group(s) on the aryl group,
(20) a carboxy group,
(21) a lower alkoxycarbonyl group,
(22) a carboxy lower alkyl group,
(23) a lower alkoxycarbonyl lower alkyl group,
(24) a lower alkanoylamino lower alkanoyl group,
(25) a carboxy lower alkenyl group,
(26) a lower alkoxycarbonyl lower alkenyl group,
(27) a carbamoyl lower alkenyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a halogen substituted lower alkyl group as a substituent,
(28) a carbamoyl group that may have a group(s) selected from the group consisting of the groups (i) to (lxxviii) below as a substituent:
(i) a lower alkyl group,
(ii) a lower alkoxy group,
(iii) a hydroxy lower alkyl group,
(iv) a lower alkoxy lower alkyl group,
(v) an aryloxy lower alkyl group,
(vi) a halogen substituted lower alkyl group,
(vii) an amino lower alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, an aroyl group, and a carbamoyl group,
(viii) a cyclo C3-C8 alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a hydroxy group, a lower alkoxycarbonyl group, and a phenyl lower alkoxy group as a substituent,
(ix) a cyclo C3-C8 alkyl substituted lower alkyl group,
(x) a lower alkenyl group,
(xi) a carbamoyl lower alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, phenyl group that may have a lower alkyl group(s), and a phenyl group(s) that may have a lower alkoxy group(s) as a substituent,
(xii) a lower alkoxycarbonyl lower alkyl group,
(xiii) a furyl lower alkyl group (that may have a lower alkyl group(s) as a substituent) on the furyl group,
(xiv) a tetrahydrofuryl lower alkyl group,
(xv) a 1,3-dioxolanyl lower alkyl group,
(xvi) a tetrahydropyranyl lower alkyl group,
(xvii) a pyrrolyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the pyrrolyl group),
(xviii) a lower alkyl group substituted with a dihydropyrazolyl group that may have an oxo group(s),
(xix) a pyrazolyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the pyrazolyl group),
(xx) an imidazolyl lower alkyl group,
(xxi) a pyridyl lower alkyl group,
(xxii) a pyrazinyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the pyrazinyl group),
(xxiii) a pyrrolidinyl lower alkyl group (that may have a group(s) selected from the group consisting of an oxo group(s) and a lower alkyl group as a substituent on the pyrrolidinyl group),
(xxiv) a piperidyl lower alkyl group (that may have a group(s) selected from the group consisting of a benzoyl group and a lower alkanoyl group as a substituent on the piperidyl group),
(xxv) a piperazinyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the piperazinyl group),
(xxvi) a morpholinyl lower alkyl group,
(xxvii) a thienyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the thienyl group),
(xxviii) a thiazolyl lower alkyl group,
(xxix) a dihydrobenzofuryl lower alkyl group,
(xxx) a benzopyranyl lower alkyl group (that may have an oxo group(s) as a substituent on the benzopyranyl group),
(xxxi) a benzimidazolyl lower alkyl group,
(xxxii) an indolyl lower alkyl group that may have a lower alkoxycarbonyl group(s) on the lower alkyl group,
(xxxiii) an imidazolyl lower alkyl group that has a substituent(s) selected from the group consisting of a carbamoyl group and a lower alkoxycarbonyl group on the lower alkyl group,
(xxxiv) a pyridyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxy group, and a lower alkylthio lower alkyl group as a substituent,
(xxxv) a pyrrolidinyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, and an aroyl group as a substituent,
(xxxvi) a piperidyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, and an aroyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a halogen atom as a substituent,
(xxxvii) a tetrahydrofuryl group that may have an oxo group(s),
(xxxviii) a hexahydroazepinyl group that may have an oxo group(s),
(xxxix) a pyrazolyl group that may have a group(s) selected from the group consisting of a lower alkyl group, an aryl group, and a furyl group as a substituent,
(xi) a thiazolyl group,
(xli) a thiadiazolyl group that may have a lower alkyl group(s),
(xlii) an isoxazolyl group that may have a lower alkyl group(s),
(xliii) an indazolyl group,
(xliv) an indolyl group,
(xlv) a tetrahydrobenzothiazolyl group,
(xlvi) a tetrahydroquinolyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen atom, and an oxo group as a substituent,
(xlvii) a quinolyl group that may have a lower alkyl group(s),
(xlvii) a benzodioxolyl lower alkyl group,
(xlix) an aryl group that may have a group(s) as a substituent, selected from the group consisting of
a halogen atom: a lower alkyl group; a lower alkoxy group; a halogen substituted lower alkyl group; a halogen substituted lower alkoxy group; a lower alkenyl group; an amino group that may have a group(s) selected from the group consisting of a lower alkanoyl group, a lower alkyl sulfonyl group, a lower alkyl group, and an aryl group; a sulfamoyl group; a lower alkylthio group; a lower alkanoyl group; a lower alkoxycarbonyl group; a pyrrolyl group; a lower alkynyl group; a cyano group; a nitro group; an aryloxy group; an aryl lower alkoxy group; a hydroxy group; a hydroxy lower alkyl group; a carbamoyl group that may have a group(s) selected from the group consisting of a lower alkyl group and an aryl group; a pyrazolyl group; a pyrrolidinyl group that may have an oxo group(s): an oxazolyl group; an imidazolyl group that may have a lower alkyl group(s); a dihydrofuryl group that may have an oxo group(s); a thiazolidinyl lower alkyl group that may have an oxo group(s); an imidazolyl lower alkanoyl group; and a piperidinylcarbonyl group,
(l) a cyano lower alkyl group,
(li) a dihydroquinolyl group that may have a group(s) selected from the group consisting of a lower alkyl group and an oxo group,
(lii) a halogen substituted lower alkylamino group,
(liii) a lower alkylthio lower alkyl group,
(liv) an amidino group that may have a lower alkyl group(s),
(lv) an amidino lower alkyl group,
(lvi) a lower alkenyloxy lower alkyl group,
(lvii) an arylamino group that may have a substituent(s) selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen substituted lower alkyl group, and a halogen substituted lower alkoxy group, on the aryl group,
(lviii) an aryl lower alkenyl group,
(lix) a pyridylamino group that may have a lower alkyl group(s),
(lx) an aryl lower alkyl group (that may have on the aryl group and/or the lower alkyl group a group(s) selected from the group consisting of a halogen atom, a lower alkyl group, a halogen substituted lower alkyl group, a halogen substituted lower alkoxy group, a lower alkoxy group, a carbamoyl group, and a lower alkoxycarbonyl group as a substituent),
(lxi) a lower alkynyl group,
(lxii) an aryloxy lower alkyl group (that may have as a substituent on the aryl group a group(s) selected from the group consisting of a lower alkoxy group, a carbamoyl group that may have a group(s) selected from the group consisting of a lower alkoxy group and a lower alkyl group, and a pyrrolidinyl group that may have an oxo group(s)),
(lxiii) an isoxazolidinyl group that ay have an oxo group(s),
(lxiv) a dihydroindenyl group,
(lxv) an aryl lower alkoxy lower alkyl group,
(lxvi) a tetrahydropyranyl group,
(lxvii) an azetidinyl group that may have a group(s) selected from the group consisting of a lower alkanoyl group and an aroyl group,
(lxviii) an azetidinyl lower alkyl group that may have a group(s) selected from the group consisting of a lower alkanoyl group and aroyl group,
(lxix) a tetrazolyl group,
(lxx) an indolinyl group that may have an oxo group(s),
(lxxi) a triazolyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a lower alkylthio group,
(lxxii) an imidazolyl group that may have a carbamoyl group(s),
(lxxiii) an oxazolyl group that may have a lower alkyl group(s),
(lxxiv) an isothiazolyl group that may have a lower alkyl group(s),
(lxxv) a benzimidazolyl group,
(lxxvi) a dihydrobenzothiazolyl group that may have an oxo group(s),
(lxxvii) a thienyl group that may have a lower alkoxycarbonyl group(s), and
(lxxviii) an oxazolyl lower alkyl group that may have a lower alkyl group(s),
(29) an amino lower alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a halogen substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, an aryl group, an aryl lower alkyl group, an aroyl group, and an amino substituted alkyl group (that may have a lower alkyl group(s) as a substituent on the amino group) on the amino group,
(30) a lower alkyl group substituted with a carbamoyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a halogen substituted lower alkyl group,
(31) a thiocarbamoyl group that may have a lower alkyl group(s),
(32) a sulfamoyl group,
(33) an oxazolidinyl group that may have an oxo group(s),
(34) an imidazolidinyl group that may have a substituent(s) selected from the group consisting of an oxo group and a lower alkyl group,
(35) a pyrrolidinyl group that may have an oxo group(s),
(36) an imidazolyl group,
(37) a triazolyl group,
(38) an isoxazolyl group,
(39) a piperidyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, an arylsulfonyl group, an oxo group, a hydroxy group, and an amino group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, and lower alkanoylamino lower alkanoyl group,
(40) a piperidylcarbonyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group, a hydroxy group, a hydroxy lower alkyl group, a lower alkanoyl group, a carboxy lower alkyl group, a lower alkyl carbamoyl lower alkyl group, a carbamoyl group, a lower alkoxy group, a carboxy group, a lower alkoxycarbonyl group, an amino group (on which 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, and an aroyl group may be present), a piperidyl group (on which a group(s) selected from the group consisting of a lower alkanoyl group, a lower alkoxycarbonyl group, and an aroyl group may be present), a piperazinyl group (on which a lower alkyl group(s) may be present as a substituent), a 1,4-dioxa-8-azaspiro[4.5]decyl group, a morpholinyl group, a hexahydro-1,4-diazepinyl group (on which a lower alkyl group(s) may be present as a substituent), a pyridyl group, a pyridyloxy group, a pyridyl lower alkoxy group, a tetrahydroquinolyl group (on which an oxo group(s) may be present), a benzodioxolyl group, an aryl lower alkoxy group (that may have a group(s) selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group, and a halogen substituted lower alkoxy group on the aryl group), an aryl group (on which a group(s) selected from the group consisting of a halogen atom, a lower alkoxy group, and a hydroxy group may be present), an aryloxy group (that may have on the aryl group a group(s) selected from the group consisting of a cyano group, a halogen atom, lower alkyl group, a lower alkoxy group, and a halogen substituted lower alkyl group), an aryl lower alkyl group (that may have on the aryl group a group(s) selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group, and a halogen substituted lower alkyl group), and an aroyl group (that may have on the aryl group a group(s) selected from the group consisting of a halogen atom and a lower alkoxy group),
(41) a pyrrolidinylcarbonyl group that may have a group as a substituent, selected from the group consisting of a hydroxy lower alkyl group, a carbamoyl group, a hydroxy group, an amino group (that may have on the amino group a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, and an aroyl group), a morpholinyl lower alkyl group, a pyrrolidinyl lower alkyl group, a piperidyl lower alkyl group, a piperazinyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the piperazinyl group), an amino lower alkyl group (that may have a lower alkyl group(s) as a substituent on the amino group), an aryloxy group (that may have a halogen substituted lower alkoxy group(s) on the aryl group), an aryloxy lower alkyl group (that may have a halogen substituted lower alkoxy group(s) on the aryl group), and a tetrahydroquinolyl group (on which an oxo group(s) may be present),
(42) a piperazinylcarbonyl group that may have a group(s) as a substituent, selected from the group consisting of a lower alkyl group, a cyclo C3-C8 alkyl group, a lower alkanoyl group, a hydroxy lower alkyl group, a lower alkoxy lower alkyl group, a lower alkoxycarbonyl group, an amino lower alkyl group (that may have a lower alkyl group(s) as a substituent on the amino group), a piperidyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the piperidyl group), a morpholinyl lower alkyl group, a pyrrolidinyl lower alkyl group, a 1,3-dioxolanyl lower alkyl group, a tetrahydrofuryl lower alkyl group, a pyridyl lower alkyl group (that may have a phenyl group(s) as a substituent on the lower alkyl group), a imidazolyl lower alkyl group, a furyl lower alkyl group, a pyrrolidinylcarbonyl lower alkyl group, a piperidyl group (that may have a lower alkyl group(s) as a substituent), pyridyl group (that may have on the pyridyl group a group(s) selected from the group consisting of a lower alkyl group, a cyano group, and a halogen substituted lower alkyl group as a substituent), a thieno[2,3-b]pyridyl group, an aryl group (on which a group(s) selected from the group consisting of a halogen atom and a lower alkyl group may be present), an aroyl group, a furyl carbonyl group, an aryl lower alkoxycarbonyl group, and an oxo group,
(43) a hexahydroazepinylcarbonyl group,
(44) a hexahydro-1,4-diazepinylcarbonyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group and a pyridyl group,
(45) a dihydropyrrolylcarbonyl group that may have a lower alkyl group(s),
(46) a thiomorpholinylcarbonyl group,
(47) a morpholinylcarbonyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a piperidyl lower alkyl group, and an aryl group,
(48) a thiazolidinyl carbonyl group that may have an aryl group(s) that may have a group(s) selected from the group consisting of a lower alkoxy group and a cyano group,
(49) an azabicyclo[3.2.2]nonylcarbonyl group,
(50) an 8-azabicyclo[3.2.1]octylcarbonyl group that may have a halogen substituted or unsubstituted aryloxy group(s),
(51) an indolinylcarbonyl group,
(52) a tetrahydroquinolylcarbonyl group,
(53) a tetrahydropyrido[3.4-b]indolylcarbonyl group,
(54) a morpholinyl lower alkyl group,
(55) a piperazinyl lower alkyl group that may have a lower alkyl group(s) on the piperazinyl group,
(56) a morpholinylcarbonyl lower alkyl group,
(57) a piperazinylcarbonyl lower alkyl group that may have a lower alkyl group(s) on the piperazinyl group,
(58) an oxo group,
(59) an amino lower alkoxy group (that may have a lower alkyl group(s) on the amino group),
(60) a lower alkoxy lower alkoxy group,
(61) a piperazinyl group that may have a group(s) selected from the group consisting of an oxo group, a lower alkyl group, a lower alkanoyl group, and a lower alkoxycarbonyl group,
(62) a morpholinyl group,
(63) a 1,3,8-triazaspiro[4.5]decanylcarbonyl group that may have a group(s) selected from the group consisting of an oxo group and an aryl group,
(64) a tetrahydropyridylcarbonyl group that may have a pyridyl group(s),
(65) an imidazolidinylcarbonyl group that may have a thioxo group(s), and
(66) a 1,4-dioxa-8-azaspiro[4.5]decanyl group.Join the waitlist — get patent alerts
Track US2014031334A1 — get alerts on status changes and closely related new filings.
We store only your email — no account needed. See our privacy policy.