Aminopyrazine derivative and medicine
The present invention relates to a compound represented by general formula [1] satisfying the following (I) or (II), or a pharmaceutical acceptable salt of the compound. (I) X is CH or N; R 1 is a halogen atom, and R 2 is H, a halogen atom, CN, [2], [3], [8], [9], an —O-alkyl, an —O-(saturated ring), etc. [2]: —C(R C )(R D )(R E ) (R C to R E each are H, an alkyl, etc.) [3]: —N(R F )(R G ) (R F and R G each are H, OH, amino, a (hetero)aryl, etc.) [8]: —C(═O)R L (R L is an alkyl, OH, an alkoxy, amino, etc.) [9]: a (substituted)phenyl; (II) X is >C—C(—O)R B (R B is a (substituted)amino, an alkoxy, OH, etc.); R 1 is a halogen atom; R 2 is H; R 3 is H or OH; and R 3 and R 4 each are H or an alkyl.
1. A compound represented by the following general formula [1] or a pharmaceutically acceptable salt thereof,
wherein the compound is defined by the following (I) or (II)
(I):
X represents CH or N;
R 1 represents halogen;
R 2 represents:
(1) H,
(2) halogen,
(3) cyano,
(4) a group represented by the following general formula [2]:
(wherein * indicates the binding position; and R C , R D and R E are the same or different and each represents (a) H, or (b) alkyl optionally substituted by hydroxy or alkoxy, or alternatively two of R C , R D and R E are taken together with the adjacent C to represent a N-contaning saturated heterocyclic group, and the other one is H, the saturated heterocyclic group optionally substituted by alkylsulfonyl),
(5) a group represented by the following general formula [3]:
(wherein * has the same meaning as described above; and R F and R G are the same or different and each represents (a) H, (b) alkyl optionally substituted by one or two groups selected from the group consisting of hydroxy, amino, dialkylamino, a saturated cyclic amino group, alkylcarbonylamino, alkylsulfonylamino, aryl, heteroaryl optionally substituted by alkyl, tetrahydrofuranyl, and carbamoyl, (c) alkylcarbonyl, (d) alkylsulfonyl, (e) carbamoyl, or (f) heteroaryl optionally substituted by alkyl, or alternatively R F and R G are taken together with the adjacent N to represent a saturated cyclic amino group, which may optionally be substituted by one or two groups selected from the group consisting of (a) halogen, (b) cyano, (c) hydroxy, (d) alkyl optionally substituted by one or two groups selected from the group consisting of hydroxy, alkoxy, amino, alkoxycarbonylamino, alkylsulfonylamino, and alkylcarbonylamino, (e) cycloalkyl, (f) haloalkyl, (g) alkoxy, (h) oxo, (i) a group represented by the following general formula [4]:
(wherein * has the same meaning as described above; and R H represents alkyl or aryl), (j) a group represented by the following general formula [5]:
(wherein * has the same meaning as described above; and R I and R J are the same or different and each represents H, alkyl, carbamoyl, alkylcarbonyl, or alkylsulfonyl), (k) a group represented by the following general formula [6]:
(wherein * has the same meaning as described above; and R K represents alkyl, hydroxy, amino, alkylamino, dialkylamino, cycloalkylamino, (cycloalkyl)alkylamino, (hydroxyalkyl)amino, (alkoxyalkyl)amino, alkoxy, alkylsulfonylamino, or a saturated cyclic amino group), and (l) a saturated cyclic amino group optionally substituted by hydroxyl; and the staturated cyclic amino group, which is formed by combining R F , R G and the adjacent N, may form a spiro-linkage with a group represented by the following general formula [7A] or [7B]:
(wherein * has the same meaning as described above)),
(6) a group represented by the following general formula [8]:
(wherein * has the same meaning as described above; and R L represents (a) alkyl, (b) hydroxy, (c) alkoxy, (d) a saturated cyclic amino group optionally substituted by alkyl or alkylsulfonyl, or (e) an amino optionally substituted by one or two groups selected from the group consisting of alkyl, cycloalkyl, (cycloalkyl)alkyl, aralkyl, haloalkyl, dialkylaminoalkyl, alkoxyalkyl, and hydroxyalkyl),
(7) a group represented by the following general formula [9]:
(wherein * has the same meaning as described above; and R M , R N and R O are the same or different and each represents H, halogen, cyano, alkoxy, carbamoyl, sulfamoyl, monoalkylaminosulfonyl, or alkylsulfonyl, or alternatively two of R M , R N and R O are taken together to represent methylenedioxy),
(8) —OR P (R P represents an alkyl optionally substituted by a group selected from the group consisting of hydroxy, dialkylamino, alkoxy, tetrahydrofuranyl, and cycloalkyl, or an optionally O-containing saturated cyclic group optionally substituted by hydroxy), or
(9) a heteroaryl optionally substituted by one or two groups selected from the group consisting of cyano, halogen, hydroxy, alkoxy, alkylcarbonyl, carbamoyl, alkyl, cycloalkyl, (cycloalkyl)alkyl, aralkyl, hydroxycarbonyl and alkoxyalkyl;
R 3 represents H or hydroxy;
R 4 represents H or alkyl; and
R 5 represents H or alkyl;
(II):
X represents —CR A ;
R A represents a group represented by the following general formula [10]:
(wherein * has the same meaning as described above; and R B represents (a) amino optionally substituted by one or two groups selected from the group consisting of alkyl, cycloalkyl, (cycloalkyl)alkyl, and alkoxyalkyl, (b) alkoxy, (c) hydroxy, or (d) a saturated cyclic amino group);
R 1 represents halogen;
R 2 represents H;
R 3 represents H or hydroxy;
R 4 represents H or alkyl; and
R 5 represents H or alkyl.
2. The compound or pharmaceutically acceptable salt thereof according to claim 1 ,
wherein the compound represented by the general formula [1] is defined by the following [i] or [ii]:
[i]:
X is CH or N;
R 1 is halogen;
R 2 is:
(1) a group represented by the following general formula [11]:
(wherein * indicates the binding position; and R F1 and R G1 are the same or different and each represents (a) H, (b) an alkyl optionally substituted by one or two groups selected from the group consisting of hydroxy, amino, dialkylamino, a saturated cyclic amino group, alkylcarbonylamino, alkylsulfonylamino, aryl, heteroaryl optionally substituted by alkyl, tetrahydrofuranyl, and carbamoyl, (c) alkylcarbonyl, (d) alkylsulfonyl, (e) carbamoyl, or (f) heteroaryl optionally substituted by alkyl, or alternatively, R F1 and R G1 are taken together with the adjacent N to represent a saturated cyclic amino group, which may optionally be substituted by one or two groups selected from the group consisting of (a) halogen, (b) cyano, (c) hydroxy, (d) alkyl optionally substituted by one or two groups selected from the group consisting of hydroxy, alkoxy, amino, alkoxycarbonylamino, alkylsulfonylamino and alkylcarbonylamino, (e) cycloalkyl, (f) haloalkyl, (g) alkoxy, (h) oxo, (i) a group represented by the following general formula [4]:
(wherein * has the same meaning as described above; and R H represents alkyl or aryl), (j) a group represented by the following general formula [5]:
(wherein * has the same meaning as described above; and R I and R J are the same or different and each represents H, alkyl, carbamoyl, alkylcarbonyl, or alkylsulfonyl), (k) a group represented by the following general formula [6]:
(wherein * has the same meaning as described above; and R K represents alkyl, hydroxy, amino, alkylamino, dialkylamino, cycloalkylamino, (cycloalkyl)alkylamino, (hydroxyalkyl)amino, (alkoxyalkyl)amino, alkoxy, alkylsulfonylamino, or a saturated cyclic amino group), and (l) a saturated cyclic amino group optionally substituted by hydroxyl,
(2) a group represented by the following general formula [8]:
(wherein * has the same meaning as described above; and R L represents (a) alkyl, (b) hydroxy, (c) alkoxy, (d) a saturated cyclic amino group optionally substituted by alkyl or alkylsulfonyl, or (e) an amino optionally substituted by one or two groups selected from the group consisting of alkyl, cycloalkyl, (cycloalkyl)alkyl, aralkyl, haloalkyl, dialkylaminoalkyl, alkoxyalkyl, and hydroxyalkyl),
(3) a group represented by the following general formula [9]:
(wherein * has the same meaning as described above; and R M , R N and R O are the same or different and each represents H, halogen, cyano, alkoxy, carbamoyl, sulfamoyl, monoalkylaminosulfonyl, or alkylsulfonyl, or alternatively two of R M , R N and R O are taken together to represent methylenedioxy),
(4) —OR P1 (wherein R P1 represents an alkyl optionally substituted by a group selected from the group consisting of hydroxy, dialkylamino, alkoxy, tetrahydrofuranyl, and cycloalkyl), or
(5) a heteroaryl optionally substituted by one or two groups selected from the group consisting of cyano, halogen, hydroxy, alkoxy, alkylcarbonyl, carbamoyl, alkyl, cycloalkyl, (cycloalkyl)alkyl, aralkyl, hydroxycarbonyl and alkoxyalkyl;
R 3 is H or hydroxy;
R 4 is H or alkyl; and
R 5 is H or alkyl;
[ii]:
X is —CR A ;
R A is a group represented by the following general formula [10]:
(wherein * has the same meaning as described above; and R B represents (a) amino optionally substituted by one or two groups selected from the group consisting of alkyl, cycloalkyl, (cycloalkyl)alkyl, and alkoxyalkyl, (b) alkoxy, (c) hydroxy, or (d) a saturated cyclic amino group);
R 1 is halogen;
R 2 is H;
R 3 is H or hydroxy;
R 4 is H or alkyl; and
R 5 is H or alkyl.
3. The compound or pharmaceutically acceptable salt thereof according to claim 1 ,
wherein:
X is CH;
R 1 is halogen;
R 2 is:
(1) a group represented by the following general formula [11]:
(wherein * indicates the binding position; and R F1 and R G1 are the same or different and each represents (a) H, (b) an alkyl optionally substituted by one or two groups selected from the group consisting of hydroxy, amino, dialkylamino, a saturated cyclic amino group, alkylcarbonylamino, alkylsulfonylamino, aryl, heteroaryl optionally substituted by alkyl, tetrahydrofuranyl, and carbamoyl, (c) alkylcarbonyl, (d) alkylsulfonyl, (e) carbamoyl, or (f) heteroaryl optionally substituted by alkyl, or alternatively, R F1 and R G1 are taken together with the adjacent N to represent a saturated cyclic amino group, which may optionally be substituted by one or two groups selected from the group consisting of (a) halogen, (b) cyano, (c) hydroxy, (d) alkyl optionally substituted by one or two groups selected from the group consisting of hydroxy, alkoxy, amino, alkoxycarbonylamino, alkylsulfonylamino and alkylcarbonylamino, (e) cycloalkyl, (f) haloalkyl, (g) alkoxy, (h) oxo, (i) a group represented by the following general formula [4]:
(wherein * has the same meaning as described above; and R H represents alkyl or aryl), (j) a group represented by the following general formula [5]:
(wherein * has the same meaning as described above; and R I and R J are the same or different and each represents H, alkyl, carbamoyl, alkylcarbonyl, or alkylsulfonyl), (k) a group represented by the following general formula [6]:
(wherein * has the same meaning as described above; and R K represents alkyl, hydroxy, amino, alkylamino, dialkylamino, cycloalkylamino, (cycloalkyl)alkylamino, (hydroxyalkyl)amino, (alkoxyalkyl)amino, alkoxy, alkylsulfonylamino, or a saturated cyclic amino group), and (l) a saturated cyclic amino group optionally substituted by hydroxyl,
(2) a group represented by the following general formula [8]:
(wherein * has the same meaning as described above; and R L represents (a) alkyl, (b) hydroxy, (c) alkoxy, (d) a saturated cyclic amino group optionally substituted by alkyl or alkylsulfonyl, or (e) an amino optionally substituted by one or two groups selected from the group consisting of alkyl, cycloalkyl, (cycloalkyl)alkyl, aralkyl, haloalkyl, dialkylaminoalkyl, alkoxyalkyl, and hydroxyalkyl),
(3) a group represented by the following general formula [9]:
(wherein * has the same meaning as described above; and R M , R N and R O are the same or different and each represents H, halogen, cyano, alkoxy, carbamoyl, sulfamoyl, monoalkylaminosulfonyl, or alkylsulfonyl, or alternatively two of R M , R N and R O are taken together to represent methylenedioxy),
(4) —OR P1 (wherein R P1 represents an alkyl optionally substituted by a group selected from the group consisting of hydroxy, dialkylamino, alkoxy, tetrahydrofuranyl, and cycloalkyl), or
(5) a heteroaryl optionally substituted by one or two groups selected from the group consisting of cyano, halogen, hydroxy, alkoxy, alkylcarbonyl, carbamoyl, alkyl, cycloalkyl, (cycloalkyl)alkyl, aralkyl, hydroxycarbonyl and alkoxyalkyl;
R 3 is H or hydroxy;
R 4 is H or alkyl; and
R 5 is H or alkyl.
4. A compound selected from the group consisting of the following (1) to (229):
(1)
(S)-4-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}piperazin-2-one,
(2)
N-{(S)-1-[2-{[(S)-1-(4-fluorophenyl)ethyl]amino}-6-(pyrazin-2-ylamino)pyrimidin-4-yl]pyrrolidin-3-yl}acetamide,
(3)
(S)-6-(3,3-difluoroazetidin-1-yl)-N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(4)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-(1-methyl-1H-pyrazol-4-yl)-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(5)
(S)—N 2′ -[1-(4-fluorophenyl)ethyl]-N 6′ -(pyrazin-2-yl)-3,4′-bipyridine-2′,6′-diamine,
(6)
(S)—N 2′ -[1-(4-fluorophenyl)ethyl]-6-methoxy-N 6′ -(pyrazin-2-yl)-3,4′-bipyridine-2′,6′-diamine,
(7)
(S)-2′-[1-(4-fluorophenyl)ethylamino]-6′-(pyrazin-2-ylamino)-3,4′-bipyridin-6-ol,
(8)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-(oxazol-5-yl)-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(9)
(S)-6-chloro-N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(10)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-[4-(methylsulfonyl)phenyl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(11)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-6-(1H-pyrazol-4-yl)pyrimidine-2,4-diamine,
(12)
(S)-2-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yloxy}ethanol,
(13) (S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-6-(pyridin-3-yl)pyrimidine-2,4-diamine,
(14)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-6-(pyridin-2-yl)pyrimidine-2,4-diamine,
(15)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-6-(pyridin-4-yl)pyrimidine-2,4-diamine,
(16)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}pyrrolidin-2-one,
(17)
(S)-4-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}piperazin-2,6-dione,
(18)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}tetrahydropyrimidin-2(1H)-one,
(19)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-6-(pyrrolidin-1-yl)pyrimidine-2,4-diamine,
(20)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-morpholino-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(21)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}imidazolidin-2-one,
(22)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-(oxazol-5-yl)-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(23)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-(6-methoxypyridin-3-yl)-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(24)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-6-(1H-pyrazol-3-yl)pyrimidine-2,4-diamine,
(25)
(S)-4-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}pyridin-2-ol,
(26)
(S)-5-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}pyridin-2-ol,
(27)
N—((R)-1-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}pyrrolidin-3-yl)acetamide,
(28)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)-4-(1H-pyrazol-4-yl)pyridine-2,6-diamine,
(29)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)-4-(1H-pyrazol-3-yl)pyridine-2,6-diamine,
(30)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-[3-(methylsulfonyl)phenyl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(31)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-[4-(methylsulfonyl)phenyl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(32)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-(1-isopropyl-1H-pyrazol-4-yl)-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(33)
N-{(S)-1-[2-{[(S)-1-(4-fluorophenyl)ethyl]amino}-6-(pyrazin-2-ylamino)pyridin-4-yl]pyrrolidin-3-yl}acetamide,
(34)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-morpholino-N-6-(pyrazin-2-yl)pyridine-2,6-diamine,
(35)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)-4-thiomorpholinopyridine-2,6-diamine,
(36)
(S)-3-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}propan-1-ol,
(37)
(S)—N-(1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-yl)acetamide,
(38)
(S)-6-(azetidin-1-yl)-N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(39)
(S)-6-(3-fluoroazetidin-1-yl)-N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(40)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-2-one,
(41)
(S)-4-(1-ethyl-1H-pyrazol-4-yl)-N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(42)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-(1-methyl-1H-pyrazol-5-yl)-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(43)
(S)-4-[1-(cyclopropylmethyl)-1H-pyrazol-4-yl]-N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(44)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-6-(thiazol-5-yl)pyrimidine-2,4-diamine,
(45)
1-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}pyrrolidin-3-ol,
(46)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(5-methylthiazol-2-yl)-N 6 -(pyrazin-2-yl)pyrimidine-2,4,6-triamine,
(47)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)-4,5′-bipyrimidine-2,6-diamine,
(48)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-(2-methoxythiazol-5-yl)-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(49)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-6-(thiazol-2-yl)pyrimidine-2,4-diamine,
(50)
(S)-5-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}picolinonitrile,
(51)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}piperidine-4-carboxamide,
(52)
(S)-5-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}picolinamide,
(53)
4-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}piperazine-2-carboxamide,
(54)
6-(3-aminopyrrolidin-1-yl)-N 2 -[(S)-1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(55)
N-(1-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}pyrrolidin-3-yl)methanesulfonamide,
(56)
(S)-2-({2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}(2-hydroxyethyl)amino)ethan-1-ol,
(57)
(S)—N 4 -[2-(dimethylamino)ethyl]-N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)pyrimidine-2,4,6-triamine,
(58)
1-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}piperidine-3-carboxamide,
(59)
(S)-1-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}pyrrolidine-2-carboxamide,
(60) (S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-[4-(methylsulfonyl)piperazin-1-yl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(61)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-6-(1H-pyrrol-3-yl)pyrimidine-2,4-diamine,
(62)
(R)-1-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-4-hydroxypyrrolidin-2-one,
(63)
N 2 -[(S)-1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-N 6 -[(tetrahydrofuran-2-yl)methyl]pyrimidine-2,4,6-triamine,
(64)
((S)-1-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}pyrrolidin-2-yl)methanol,
(65)
((R)-1-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}pyrrolidin-2-yl)methanol,
(66)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}piperidin-4-ol,
(67)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-ol,
(68)
1-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}piperidin-3-ol,
(69)
(S)-5-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}nicotinonitrile,
(70)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-6-(2H-tetrazol-5-yl)pyrimidine-2,4-diamine,
(71)
(S)—N 4 -(2-aminoethyl)-N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)pyrimidine-2,4,6-triamine,
(72)
(S)—N-(2-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-ylamino}ethyl)methanesulfonamide,
(73)
(S)—N-(2-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-ylamino}ethyl)acetamide,
(74)
(S)-2-{2-[1-(4-fluorphenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-ylamino}acetamide,
(75)
(S)-4-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}benzamide
(76)
(S)-3-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}benzonitrile,
(77)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-(furan-3-yl)-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(78)
ethyl (S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}piperidin-4-carboxylate,
(79)
(S)-5-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}nicotinamide,
(80)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}piperidine-4-carboxylic acid,
(81)
(S)-2-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-ylamino}-2-phenylethanol,
(82)
(S)-2-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-ylamino}-3-phenylpropan-1-ol,
(83)
(R)-2-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-ylamino}-4-methylpentan-1-ol,
(84)
(S)-6-[2-(dimethylamino)ethoxy]-N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine
(85)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-1H-pyrazole-4-carboxylic acid,
(86)
(S)-3-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}benzamide,
(87)
(S)-6-(benzo[d] 1,3-dioxol-5-yl)-N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(88)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-(2-fluoropyridin-4-yl)-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(89)
N 2 -[(S)-1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-6-[(tetrahydrofuran-2-yl)methoxy]pyrimidine-2,4-diamine,
(90)
(S)-2-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yloxy}ethanol,
(91)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-N 6 -[2-(pyrrolidin-1-yl)ethyl]pyrimidine-2,4,6-triamine,
(92)
(S)-3-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}isonicotinamide
(93)
(S)-3-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}isonicotinonitrile,
(94)
(S)-2-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-ylamino}-3-methylbutan-1-ol,
(95)
(S)—N 2 -[1-(4-chlorophenyl)ethyl]-6-[4-(methylsulfonyl)piperazin-1-yl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(96)
(1S,2S)-2-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yloxy}cyclohexanol,
(97)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -[(5-methylpyrazin-2-yl)methyl]-N 6 -(pyrazin-2-yl)pyrimidine-2,4,6-triamine,
(98)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(furan-2-ylmethyl)-N 6 -(pyrazin-2-yl)pyrimidine-2,4,6-triamine,
(99)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-N 6 -[1-(pyridin-3-yl)ethyl]pyrimidine-2,4,6-triamine,
(100)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-4-(hydroxymethyl)piperidin-4-ol,
(101)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-N 6 -(pyridin-2-ylmethyl)pyrimidine-2,4,6-triamine,
(102)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-N 6 -(pyridin-3-ylmethyl)pyrimidine-2,4,6-triamine,
(103)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-N 6 -(pyridin-4-ylmethyl)pyrimidine-2,4,6-triamine,
(104)
(S)-2-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-ylamino}-3-hydroxypropanamide,
(105)
(3S,4S)-1-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}pyrrolidin-3,4-diol
(106)
N 2 -[(S)-1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-6-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)pyrimidine-2,4-diamine,
(107)
(S)-8-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-1,3-dioxo-8-azaspiro[4.5]decan-2-one,
(108)
(S)-4-(1-benzyl-1H-pyrazol-4-yl)-N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(109)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-[4-(phenylsulfonyl)piperazin-1-yl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(110)
(S)-4-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}benzamide,
(111)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)-4-(1H-pyrrol-3-yl)pyridine-2,6-diamine,
(112)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(113)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-(4-methyl-1H-imidazol-1-yl)-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(114)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-(4-methoxyphenyl)-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(115)
(S)-4-(4-fluorophenyl)-N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine
(116)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-methyl-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(117)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-N-(methylsulfonyl)piperidine-4-carboxamide,
(118)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-(furan-3-yl)-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(119)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-[4-(methylsulfonyl)piperazin-1-yl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(120)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}-4-(hydroxymethyl)piperidin-4-ol,
(121)
(S)-4-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}benzenesulfonamide,
(122)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-methoxy-N-6-(pyrazin-2-yl)pyridine-2,6-diamine,
(123)
4-{2-[(1S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}-1λ 6 ,4-thiomorpholin-1,1-dione,
(124)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}piperidin-4-ol,
(125)
(S)-1-(4-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}-1,4-diazepan-1-yl)ethanone,
(126)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)-N 4 -(pyrimidin-2-yl)pyridine-2,4,6-triamine,
(127)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)-N 4 -(pyridin-2-yl)pyridine-2,4,6-triamine,
(128)
N 2 -[(S)-1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)-4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)pyridine-2,6-diamine,
(129)
methyl (S)-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinate,
(130)
(S)-4-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-N-methylbenzenesulfonamide,
(131)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-(4-methyl-1H-imidazol-1-yl)-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(132)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 ,N 6 -di(pyrazin-2-yl)pyridine-2,4,6-triamine
(133)
(S)-4-(cyclopropylmethoxy)-N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(134)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 2 -methyl-4-(1-methyl-1H-pyrazol-4-yl)-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine
(135)
(S)-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}methanol,
(136)
(S)-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinic acid,
(137)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-(2-methoxyethoxy)-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(138)
(S)-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidine-4-carbonitrile,
(139)
(S)-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinonitrile,
(140)
(S)-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinamide,
(141)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-(1,2,4-oxadiazol-3-yl)-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(142)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-(1,2,4-oxadiazol-3-yl)-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(143)
methyl (S)-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)nicotinate,
(144)
(S)-2-[1-(4-fluorophenyl)ethylamino]-N,N-dimethyl-6-(pyrazin-2-ylamino)isonicotinamide,
(145)
(S)—N-[2-(dimethylamino)ethyl]-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinamide,
(146)
(S)—N-t-butyl-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinamide,
(147)
(S)—N-ethyl-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinamide,
(148)
(S)-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}[4-(methanesulfonyl)piperazin-1-yl]methanone,
(149)
(S)-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}(pyrrolidin-1-yl)methanone,
(150)
(S)-2-[1-(4-fluorophenyl)ethylamino]-N-isopropyl-6-(pyrazin-2-ylamino)isonicotinamide,
(151)
(S)-1-{2-[(S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidine-2-carboxamide,
(152)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)-4-(tetrahydro-2H-pyran-4-yloxy)pyridine-2,6-diamine,
(153)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidine-3-carboxamide,
(154)
(S)-2-[1-(4-fluorophenyl)ethylamino]-N-(2-hydroxyethyl)-6-(pyrazin-2-ylamino)isonicotinamide,
(155)
(S)-2-[1-(4-fluorophenyl)ethylamino]-N-methyl-6-(pyrazin-2-ylamino)isonicotinamide,
(156)
(S)-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}(morpholino)methanone,
(157)
(S)—N-benzyl-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinamide,
(158)
(S)—N-cyclopropyl-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinamide,
(159)
(S)-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl} (4-methylpiperazin-1-yl)methanone,
(160)
(S)-2-[1-(4-fluorophenyl)ethylamino]-N-(2-methoxyethyl)-6-(pyrazin-2-ylamino)isonicotinamide,
(161)
(S)-2-[1-(4-fluorophenyl)ethylamino]-N-propyl-6-(pyrazin-2-ylamino)isonicotinamide,
(162)
(S)—N-cyclopropylmethyl-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinamide,
(163)
(S)—N-cyclobutyl-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinamide,
(164)
(S)—N-butyl-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinamide,
(165)
(S)-2-[1-(4-fluorophenyl)ethylamino]-N-isobutyl-6-(pyrazin-2-ylamino)isonicotinamide,
(166)
(S)-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)-N-(2,2,2-trifluoroethyl)isonicotinamide,
(167)
(S)-2-[1-(4-fluorophenyl)ethylamino]-N-(3-hydroxypropyl)-6-(pyrazin-2-ylamino)isonicotinamide,
(168)
(S)—N-(2-ethoxyethyl)-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinamide,
(169)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-N-methylazetidine-3-carboxamide,
(170)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-(methoxymethyl)-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(171)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-N,N-dimethylazetidine-3-carboxamide,
(172)
(S)—N-(1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-yl)methanesulfonamide,
(173)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-carbonitrile,
(174)
2-(4-fluorophenyl)-2-[4-(1-methyl-1H-pyrazol-4-yl)-6-(pyrazin-2-ylamino)pyridin-2-ylamino]ethanol,
(175)
(S)—N-ethyl-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidine-3-carboxamide,
(176)
(S)—N,N-diethyl-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidine-3-carboxamide,
(177)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}ethanone,
(178)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-(3-methoxyazetidin-1-yl)-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(179)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-3-methylazetidin-3-ol,
(180)
(S)-2-[1-(4-fluorophenyl)ethylamino]-N-methyl-6-(pyrazin-2-ylamino)nicotinamide,
(181)
(S)-2-[1-(4-fluorophenyl)ethylamino]-N,N-dimethyl-6-(pyrazin-2-ylamino)nicotinamide,
(182)
(S)-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)nicotinamide,
(183)
(S)-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-3-yl}(morpholino)methanone,
(184)
(S)—N-(cyclopropylmethyl)-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)nicotinamide,
(185)
(S)—N-(1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl} azetidin-3-yl)ethanesulfonamide,
(186)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-N-isopropylazetidine-3-carboxamide,
(187)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-3-(trifluoromethyl)azetidin-3-ol,
(188)
(S)-(1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-yl)(pyrrolidin-1-yl)methanone,
(189)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-N-(2-methoxyethyl)azetidine-3-carboxamide,
(190)
(S)-(1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-yl)(piperidin-1-yl)methanone,
(191)
(S)-(1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-yl)(morpholino)methanone,
(192)
(S)—N-(cyclopropyl)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidine-3-carboxamide,
(193)
(S)—N-(cyclopropylmethyl)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidine-3-carboxamide,
(194)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-N-(2-hydroxyethyl)azetidine-3-carboxamide,
(195)
(S)-3-cyclopropyl-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-ol,
(196)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-3-isopropylazetidin-3-ol,
(197)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}azetidin-3-ol,
(198)
(S)-3-cyclopropyl-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}azetidin-3-ol,
(199)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}-3-isopropylazetidin-3-ol,
(200)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}-3-methylazetidin-3-ol,
(201)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}-3-(trifluoromethyl)azetidin-3-ol,
(202)
(S)-4-(3,3-difluoroazetidin-1-yl)-N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(203)
(S)—N-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}acetamide,
(204)
(S)—N-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}methanesulfonamide,
(205)
(S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}urea,
(206)
(S)-4-(3-cyclopropyl-3-methoxyazetidin-1-yl)-N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(207)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-(3-isopropyl-3-methoxyazetidin-1-yl)-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(208)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-(3-methoxy-3-methylazetidin-1-yl)-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(209)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-(1-methyl-1H-pyrazol-4-yl)-N 6 -(5-methylpyrazin-2-yl)pyridine-2,6-diamine,
(210)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-[1-(methanesulfonyl)piperidin-4-yl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(211)
(S)—N-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}propionamide,
(212) (S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(213)
(S)-4-(1-cyclopropyl-1H-pyrazol-4-yl)-N 2 -[1-(4-fluorophenyl)ethyl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(214)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-[1-(methoxymethyl)-1H-pyrazol-4-yl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine,
(215)
(S)-6-[3-(dimethylamino)azetidin-1-yl]-N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(216)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-[3-(methylamino)azetidin-1-yl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(217)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)-6-[3-(pyrrolidin-1-yl)azetidin-1-yl]pyrimidine-2,4-diamine,
(218)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-(3-morpholinoazetidin-1-yl)-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(219)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-6-[3-(4-methylpiperazin-1-yl)azetidin-1-yl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(220)
(S)-(1-{1-[2-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-yl)piperidin-4-ol,
(221)
4-{2-[(1S)-1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}-1λ 6 ,4-thiomorpholin-1,1-dione,
(222)
(S)-1-(1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-yl)urea,
(223)
(S)-(1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-yl)methanol,
(224)
t-butyl (S)-(1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-yl)methyl carbamate,
(225)
(S)-6-[3-(aminomethyl)azetidin-1-yl]-N 2 -[1-(4-fluorophenyl)ethyl]-N 4 -(pyrazin-2-yl)pyrimidine-2,4-diamine,
(226)
(S)—N-[(1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-yl)methyl]ethane sulfonamide,
(227)
(S)—N-[(1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-yl)methyl]acetamide,
(228)
(S)—N 2 -[1-(4-fluorophenyl)ethyl]-4-[3-morpholinoazetidin-1-yl]-N 6 -(pyrazin-2-yl)pyridine-2,6-diamine, and
(229)
(S)-1-(1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyridin-4-yl}azetidin-3-yl)piperidin-4-ol;
or a pharmaceutically acceptable salt thereof.
5. A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof described in claim 1 as an active ingredient.
6. A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof described in claim 2 as an active ingredient.
7. A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof described in claim 3 as an active ingredient.
8. A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof described in claim 4 as an active ingredient.