US 7,803,801 B2 · Aminopyridine compounds having Syk inhibitory activity

Abstract

The present invention relates to an aminopyridine compound represented by the following general formula (I) or a salt thereof and an Syk inhibitor containing the compound or a salt thereof as an active ingredient. Here, X1, X2, X3, Z, Y1, Y2 represent a carbon atom or a nitrogen atom, R, R1, R5, R6 represent a hydrogen atom, an alkyl group, etc., and R7 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, —CpH2(p-1)(Ra1)(Ra2)—O—Ra3, —C(═O)—Rd1, a 5- or 6-membered saturated heterocyclic group, an aromatic heterocyclic group, —N(Rh1)(Rh2), etc. The aminopyridine compound of the present invention has not only high Syk inhibitory activity but also properties to selectively inhibit Syk.

An aminopyridine compound represented by the following formula (I):

wherein X1 represents
(1) —C(R2)═ or
(2) a nitrogen atom;
X2 represents
(1) C(R3)═ or
(2) a nitrogen atom;
X3 represents
(1) —C(R4)═ or
(2) a nitrogen atom;
Z represents
(1) a nitrogen atom or
(2) —C(R6′)═;
Y1 represents
(1) —CH═ or
(2) a nitrogen atom;
Y2 represents
(1) —CH═, or,
(2) a nitrogen atom;
R1 represents
(1) a hydrogen atom,
(2) a C1-6 alkyl group or
(3) an acyl group;
R1 represents
(1) a hydrogen atom,
(2) a C1-6 alkyl group or
(3) a halogen atom;
R2 represents
(1) a hydrogen atom,
(2) a C1-6 alkyl group or
(3) a halogen atom;
R3 represents
(1) a hydrogen atom,
(2) a halogen atom,
(3) —N(R31)(R32),
wherein R31 and R32 represent a hydrogen atom or a C1-6 alkyl group,
(4) a hydroxyl group,
(5) a C1-6 alkoxy group, wherein the C1-6 alkyl group in the C1-6 alkoxy group may be substituted with a substituent selected from the following group Aa:
[Group Aa]
(a) a hydroxyl group,
(b) a C1-6 alkoxy group,
(c) —N(R31)(R32),
wherein R31 and R32 are the same as above,
(d) —COOR33,
wherein R33 represents a hydrogen atom or a C1-6 alkyl group,
(e) —CO—N(R31)(R32),
wherein R31 and R32 are the same as above, and
(f) a halogen atom,
(6) an aralkoxy group,
(7) an acyl group,
(8) a saturated heterocyclic group or an aromatic heterocyclic group, wherein the heterocyclic group may be substituted with a C1-6 alkyl group, and the saturated heterocyclic group may partially have a double bond,
(9) a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a substituent selected from the following group Ab:
[group Ab]
(a) a hydroxyl group,
(b) —COOR33, wherein R33 is the same as the above,
(c) —CO—N(R31)(R32), wherein R31 and R32 are the same as above, and
(d) a halogen atom,
(10) —COOR33,
wherein R33 is the same as the above,
(11) —CO—N(R31)(R32), wherein R31 and R32 are the same as above, or
(12) a cyano group;
R3 together with R2 may form —C═C—C═C—;
R4 represents
(1) a hydrogen atom,
(2) a C1-6 alkyl group or
(3) a nitro group;
R5 represents
(1) a hydrogen atom,
(2) a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a hydroxyl group or a C1-6 alkoxy group,
(3) —COOR51,
wherein R51 represents a hydrogen atom or a C1-6 alkyl group, or
(4) a nitro group;
R6 and R6′ may be the same or different and each represent
(1) a hydrogen atom,
(2) a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a hydroxyl group or a C1-6 alkoxy group,
(3) —COOR61,
wherein R61 represents a hydrogen atom or a C1-6 alkyl group,
(4) —N(R62)(R63),
wherein R62 and R63 may be the same or different and each represent a hydrogen atom, a C1-6 alkyl group, a C1-6 alkoxy group or an acyl group,
(5) —CO—N(R62)(R63),
wherein R62 and R63 are the same as above, or
(6) an acyl group;
R7 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, or the following Ra, Rb, Rc, Rd, Re, Rf, Rg or Rh;
Ra represents —CpH2(p-1)(Ra1)(Ra2)—O—Ra3,
wherein
(1) p represents an integer from 1 to 6,
(2) Ra1 represents a hydrogen atom or a C1-6 alkyl group,
(3) Ra2 represents a hydrogen atom, a C1-6 alkyl group, an aralkyl group or an aryl group, wherein the C1-6 alkyl group, aralkyl group and aryl group may be substituted with a substituent respectively selected from the following group Ba:
[Group Ba]
(a) a hydroxyl group,
(b) a carboxy group,
(c) a C1-6 alkoxycarbonyl group,
(d) an amino group,
(e) a C1-6 alkylamino group,
(f) a di-C1-6 alkylamino group,
(g) an acyloxy group and
(h) a halogen atom,
(4) Ra3 represents a hydrogen atom, an acyl group, —CON(Ra31)(Ra32) or a C1-6 alkyl group, wherein the alkyl group may be substituted with a C1-6 alkoxycarbonyl group or —CON(Ra31)(Ra32),
wherein Ra31 and Ra32 may be the same or different and each represent
a hydrogen atom,
an acyl group, wherein the acyl group may be substituted with a hydroxyl group or a carboxy group,
a C1-6 alkyl group wherein C1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a carboxy group, a C1-6 alkoxycarbonyl group, a carbamoyl group, a C1-6 alkylcarbamoyl group and a di-C1-6 alkylcarbamoyl group,
a C1-6 alkoxycarbonyl group or
a C1-6 alkylsulfonyl group, or
Ra31 and Ra32 together with the adjacent nitrogen atom may form a 5- or 6-membered saturated heterocyclic group which has one or more nitrogen atoms, wherein the saturated heterocyclic group may be substituted with a hydroxyl group, an oxo group, an aralkylamino group or an acylamino group;
Rb represents —CpH2(p-1)(Rb1)(Rb2)—N—(Rb3)(Rb4),
wherein
(1) p represents an integer from 1 to 6,
(2) Rb1 represents a hydrogen atom or a C1-6 alkyl group,
(3) Rb2 represents
(a) a hydrogen atom,
(b) an aralkyl group, wherein the aralkyl group may be substituted with a hydroxyl group, a C1-6 alkoxy group which may be substituted with a hydroxyl group, an aralkyloxy group or —N(Rb21)(Rb22),
wherein Rb21 and Rb22 may be the same or different and each represent a hydrogen atom, a C1-6 alkyl group, an acyl group, a carbonyl group, a C1-6 alkoxycarbonyl group or an aralkoxycarbonyl group,
(c) an aryl group, wherein the aryl group may be substituted with a hydroxyl group, a C1-6 alkoxy group or an aralkoxy group, or
(d) a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a substituent selected from the following group Ca:
[Group Ca]
a hydroxyl group,
an aralkoxy group,
—COORb23,
wherein Rb23 represents a hydrogen atom, a C1-6 alkyl group or an aralkyl group,
—N(Rb21)(Rb22), wherein Rb21 and Rb22 are the same as above, and
an aryl group, wherein the aryl may be substituted with a substituent selected from a hydroxyl group, a C1-6 alkoxy group, wherein the C1-6 alkoxy group may be substituted with a hydroxyl group, an aralkoxy group, —N(Rb21)(Rb22) and an aralkoxycarbonylamino group,
wherein Rb21 and Rb22 are the same as above, and
(4) Rb3 and Rb4 may be the same or different and each represent
(a) a hydrogen atom,
(b) a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a carboxy group, a C1-6 alkoxycarbonyl group, a carbamoyl group, a C1-6 alkylcarbamoyl group and a di-C1-6 alkylcarbamoyl group,
(c) —COORb41,
wherein Rb41 represents a hydrogen atom, a C1-6 alkyl group or an aralkyl group,
(d) —CORb42,
wherein Rb42 represents
a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a substituent selected from
a hydroxyl group,
a carboxy group,
a C1-6 alkoxycarbonyl group,
an acyl group,
an acyloxy group,
an amino group and
an acylamino group,
a C3-8 cycloalkyl group, wherein the C3-8 cycloalkyl group may be substituted with a hydroxyl group,
a 5- or 6-membered aromatic heterocyclic group having 1 to 4 hetero atoms, wherein the heterocyclic group may be substituted with a C1-6 alkyl group, or
an aryl group, wherein the aryl group may be substituted with a hydroxyl group,
(e) —CO—N(Rb43)(Rb44), wherein Rb43 and Rb44 may be the same or different and each represent a hydrogen atom, a C1-6 alkyl group or an acyl group, or
(f) —SO2—Rb45, wherein Rb45 represents a C1-6 alkyl group;
Rc represents —C(═N—Rc1)—Rc2,
wherein
(1) Rc1 represents
(a) a hydroxyl group,
(b) a C1-6 alkoxy group, wherein the C1-6 alkyl group in the C1-6 alkoxy group may be substituted with a hydroxyl group or a C1-6 alkoxy group, or
(c) an acyloxy group, and
(2) Rc2 represents a C1-6 alkyl group or an amino group;
Rd represents —C(═O)—Rd1,
wherein Rd1 represents
(1) a hydrogen atom,
(2) a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a hydroxyl group, a carboxy group or a C1-6 alkoxycarbonyl group,
(3) a hydroxyl group,
(4) a C1-6 alkoxy group, and
(5) —N(Rd11)(Rd12),
wherein Rd11 and Rd12 may be the same or different and each represent a substituent selected from the following group Da:
[Group Da]
(a) a hydrogen atom,
(b) a C1-6 alkoxy group,
(c) a C3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group, and
(d) a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a hydroxyl group, a carboxy group, a C1-6 alkoxycarbonyl group or an amino group, or
Rd11 and Rd12 together with the adjacent nitrogen atom may form a 5- or 6-membered saturated heterocyclic group which has one or more nitrogen atoms, wherein the saturated heterocyclic group may be substituted with a C1-6 alkyl groups, wherein the alkyl group may be substituted with a carboxy group, or a carboxy group;
Re represents the following Ring A:
wherein Ring A represents
a 5- or 6-membered saturated heterocyclic group having 1 or 2 hetero atoms,
a 5- or 6-membered aromatic heterocyclic group having 1 to 4 hetero atoms,
a 9- to 12-membered condensed aromatic heterocyclic group having 1 or 2 hetero atoms which may be partially saturated
a C3-8 cycloalkyl group or
a C7-11 spiroheterocycloalkyl group having 1 or 2 hetero atoms);
which may be substituted with a substituent respectively selected from the following group Ea:
[Group Ea]
(a) —ORe1, wherein Re1 represents
a hydrogen atom,
a C1-6 alkyl group, the C1-6 alkyl group may be substituted with a carboxy group or —CON(Re11)(Re12),
wherein Re11 and Re12 may be the same or different and each represent a hydrogen atom or a C1-6 alkyl group,
an acyl group,
a carbamoyl group or
an aralkyl group,
(b) —COORe2,
wherein Re2 represents a hydrogen atom or a C1-6 alkyl group,
(c) —CO—N(Re41)(Re42),
wherein Re41 and Re42 may be the same or different and each represent
a hydrogen atom,
a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a C1-6 alkoxy group, an amino group, a C1-6 alkylamino group, a di-C1-6 alkylamino group, a halogen atom, a carboxy group, a carbamoyl group, a C1-6 alkylcarbamoyl group, a di-C1-6 alkylcarbamoyl group or a 5- or 6-membered saturated heterocyclic group or aromatic heterocyclic group having 1 or 2 hetero atoms,
a hydroxyl group,
a C1-6 alkoxy group,
a C5-6 cycloalkyl group, wherein the C5-6 cycloalkyl group may be substituted with a hydroxyl group or a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a hydroxyl group, or
a C1-6 alkylsulfonyl group,
(d) —CORe3,
wherein Re3 represents
a hydrogen atom,
a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a carboxy group, a C1-6 alkoxycarbonyl group and a C1-6 alkylsulfonyl group,
a 5- or 6-membered saturated heterocyclic group or aromatic heterocyclic group having 1 or 2 hetero atoms, wherein the saturated heterocyclic group or aromatic heterocyclic group may be substituted with a hydroxyl group, an oxo group, a carboxy group, a C1-6 alkoxy group, wherein the C1-6 alkoxy group may be substituted with a carbamoyl group, a carbamoyl group, wherein the carbamoyl group may be substituted with a hydroxyl group, an acyl group, acyloxy group, an amino group, an acylamino group, wherein the acylamino group may be substituted with a hydroxyl group or carbamoyl group, a C1-6 alkylamino group, a di-C1-6 alkylamino group, a C1-6 alkylsulfonylamino group, a 5- or 6-membered saturated heterocyclic group or aromatic heterocyclic group and a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a C1-6 alkoxy group, wherein the C1-6 alkoxy group may be substituted with a carbamoyl group, an acylamino group and a carbamoyl group, or
a C5-6 cycloalkyl group or aryl group, wherein the C5-6 cycloalkyl group or aryl group may be substituted with a hydroxyl group, an oxo group, a C1-6 alkoxy group, a carbamoyl group, an acylamino group, an oximino group or an acyloxy group,
(e) an oxo group,
(f) —N(Re51)(Re52),
wherein Re51 and Re52 may be the same or different and each represent
a hydrogen atom,
a C1-6 alkylsulfonyl group,
a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a C1-6 alkoxy group and a carbamoyl group,
an acyl group, wherein the acyl group may be substituted with a hydroxyl group or a C1-6 alkoxy group,
—CON(Re11)(Re12) or, wherein Re11 and Re12 represent the same as above,
—CORe511,
wherein Re511 represents a 5- or 6-membered saturated heterocyclic group containing at least one nitrogen atom, a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a hydroxyl group, or a C5-6 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group,
(g) a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a substituent selected from the following group Eb:
[Group Eb]
a hydroxyl group,
a C1-6 alkoxy group, wherein a C1-6 alkyl group in the C1-6 alkoxy group may be substituted with a carboxy group or —CO—N(Re11)(Re12), wherein Re11 and Re12 represent the same as above,
—COORe2,
wherein Re2 represents the same as above,
—N(Re51)(Re52),
wherein Re51 and Re52 represent the same as above,
—CO—N(Re51)(Re52),
wherein Re51 and Re52 represent the same as above,
a halogen atom, and
a 5- or 6-membered saturated heterocyclic group having 1 or 2 hetero atoms, wherein the saturated heterocyclic group may be substituted with a hydroxyl group or a C1-6 alkyl group,
(h) —(CH2)n—N(Re61)—(CH2)m—CO(Re62),
wherein n and m represent an integer of 0 or 1 to 4, and n+m is 1 to 6, Re61 represents a hydrogen atom or a C1-6 alkyl group and Re62 is a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a hydroxyl group, a C1-6 alkoxy group, an amino group, a C1-6 alkylamino group or a di-C1-6 alkylamino group,
(i) a hydroxyimino group,
(j) a C1-6 alkylsulfonyl group,
(k) a cyano group,
(l) a 5- or 6-membered saturated heterocyclic group (which may be partially unsaturated) containing 1 or 2 hetero atoms selected from a nitrogen atom and an oxygen atom or a 5- or 6-membered aromatic heterocyclic group containing 1 to 4 hetero atoms selected from a nitrogen atom and an oxygen atom, wherein the saturated heterocyclic group and aromatic heterocyclic group may be substituted with an oxo group or a C1-6 alkyl group,
(m) an aminosulfonyl group and
(n) a C1-6 alkylidene group, wherein the C1-6 alkylidene group may be substituted with a halogen atom or a carboxy group;
Rf is a C1-6 alkyl group or a C2-6 alkenyl group, wherein these C1-6 alkyl group and C2-6 alkenyl group may be substituted with a substituent selected from the following group Fa:
[Group Fa]
(a) a C1-6 alkoxy group, wherein the C1-6 alkyl group in the alkoxy group may be substituted with a carboxy group, a C1-6 alkoxycarbonyl group or —CON(Rf21)(Rf22),
wherein Rf21 and Rf22 may be the same or different and each represent
a hydrogen atom,
an acyl group, wherein the acyl group may be substituted with a hydroxyl group or a carboxy group,
a C1-6 alkoxycarbonyl group,
—O—COORf1,
wherein Rf1 is a hydrogen atom or a C1-6 alkyl group,
a C1-6 alkyl group,
wherein the C1-6 alkyl group may be substituted with a hydroxyl group, a carboxy group, a C1-6 alkoxycarbonyl group, a carbamoyl group,
a C1-6 alkylsulfonyl group or
a carbamoyl group,
(b) —COORf1,
wherein Rf1 is a hydrogen atom or a C1-6 alkyl group,
(c) —N(Rf21)(Rf22),
wherein Rf21 and Rf22 represent the same as above,
(d) —CON(Rf21)(Rf22),
wherein Rf21 and Rf22 represent the same as above,
(e) —N(Rf23)CON(Rf21)(Rf22),
wherein Rf23 represents a hydrogen atom or a C1-6 alkyl group, and
Rf21 and Rf22 represent the same as above,
(f) an acyl group and
(g) a halogen atom;
Rg represents a substituent having Ring B represented by the following formula (II):
wherein A represents a linker selected from the following group Ga:
[Group Ga]
—(CH2)k,
—(CH2)k—NRg1—(CH2)j—,
—(CH2)k—O—(CO)NRg1—(CH2)j—,
—(CH2)k—NRg1(CO)—(CH2)j—,
—(CH2)k—(CO)—(CH2)j—,
—(CO)—,
—(CH2)k—O—(CH2)j—,
—(CH2)k—S—(CH2)j—,
—(CH2)k—O—(CO)—(CH2)j—,
—(CO)NRg1—, and
—(CH2)k—O—(CH2)j(CO)—(CH2)g—,
wherein k, j and g may be the same or different and represent an integer from 0 to 4 but k and j, or k and g are not 0 at the same time,
Rg1 represents
a hydrogen atom,
a hydroxyl group,
a C1-6 alkoxy group,
an acyl group, wherein the acyl group may be substituted with a hydroxyl group or a carboxy group,
a C3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a C1-6 alkyl group, wherein the alkyl group may be substituted with a carboxy group,
an aralkyl group or
a C1-6 alkyl group, wherein the alkyl group may be substituted with a hydroxyl group, —N(Rg41)(Rg42) or —CON(Rg41)(Rg42),
wherein Rg41 and Rg42 may be the same or different and represent a hydrogen atom,
an acyl group, wherein the acyl group may be substituted with a hydroxyl group,
an aralkyl group,
a C1-6 alkylsulfonyl group or,
a C1-6 alkyl group,
wherein the C1-6 alkyl group may be substituted with a hydroxyl group, a carboxy group, a C1-6 alkoxycarbonyl group, —N(Rg51)(Rg52) or —CO—N(Rg51)(Rg52),
wherein Rg51 and Rg52 may be the same or different and represent
a hydrogen atom,
an acyl group, wherein the acyl group may be substituted with a hydroxyl group,
a C1-6 alkyl group,
wherein the C1-6 alkyl group may be substituted with a hydroxyl group, a carboxy group, acylamino group, a C1-6 alkoxycarbonyl group or a halogen atom,
a C1-6 alkoxycarbonyl group,
a C1-6 alkylsulfonyl group or
a C3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group or a C1-6 alkoxy group, or
Rg51 and Rg52 together with the adjacent nitrogen atom may form a 5- or 6-membered saturated heterocyclic group which has one or more nitrogen atoms, wherein the saturated heterocyclic group may be substituted with a hydroxyl group or a C1-6 alkoxy group,
Ring B represents a ring selected from the following group Ha:
[Group Ha]
an aryl group,
a C3-8 cycloalkyl group,
a 5- to 7-membered saturated heterocyclic group containing one or more nitrogen atoms,
a 5- or 6-membered aromatic heterocyclic group containing at least one hetero atoms, and
an 8- to 11-membered condensed aromatic heterocyclic group containing at least one hetero atoms, and
the Ring B may be substituted with a substituent selected from follows group Ia:
[Group Ia]
(a) —ORg2,
wherein Rg2 represents
a hydrogen atom,
a C1-6 alkyl group or
an aralkyl group,
(b) —COORg3,
wherein Rg3 represents
a hydrogen atom,
a C1-6 alkyl group or
an aralkyl group, wherein the alkyl group may be substituted with a hydroxyl group,
(c) —N(Rg41)(Rg42),
wherein Rg41 and Rg42 represent the same as above,
(d) —CO—Rg53, wherein Rg53 represents
a C1-6 alkyl group, wherein the alkyl group may be substituted with a hydroxyl group, a carboxy group or an acylamino group,
a C3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group, a C1-6 alkoxy group or oxo group,
a 5- or 6-membered saturated heterocyclic group containing at least one hetero atoms, wherein the saturated heterocyclic group may be substituted with a hydroxyl group, a C1-6 alkyl group or an oxo group,
an aryl group, wherein the aryl may be substituted with a hydroxyl group,
a 5- or 6-membered aromatic heterocyclic group containing at least one hetero atoms,
an aralkyl group or
a 5- or 6-membered saturated heterocyclic group containing 1 or 2 hetero atoms,
(e) a C1-6 alkyl group, wherein the C1-6 alkyl group which may be substituted with a hydroxyl group, a C1-6 alkoxy group, an aralkoxy group, a carboxy group, a C1-6 alkoxycarbonyl group, —CO—Rg53, wherein Rg53 represents the same as above, —N(Rg51)(Rg52) or —CO—N(Rg51)(Rg52),
wherein Rg51 and Rg52 represent the same as above,
(f) —CO—N(Rg51)(Rg52),
wherein Rg51 and Rg52 represent the same as above ,
(g) a C1-6 alkylsulfonyl group,
(h) an oxo group,
(i) an aryl group, wherein the aryl group may be substituted with a hydroxyl group,
(j) an aralkyl group and
(k) a halogen atom;
and
Rh represents —N(Rh1)(Rh2),
wherein Rh1 represents
(1) a hydrogen atom,
(2) a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a hydroxyl group, a C1-6 alkoxy group, —N(Rg51)(Rg52), —CO—N(Rg51)(Rg52),
wherein Rg51 and Rg52 represent the same as above, a C1-6 alkylsulfonyl group or a halogen atom,
(3) a C2-6 alkenyl group,
(4) a C3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group or a C1-6 alkoxy group, or
(5) an aralkyl group,
Rh2 represents
(1) a C1-6 alkyl group, wherein the C1-6 alkyl group may be substituted with a substituent selected from the following group Ja:
[Group Ja]
a hydroxyl group,
a C1-6 alkoxy group,
a carboxy group,
an aromatic carbocyclic group, wherein the aromatic carbocyclic group may be substituted with a hydroxyl group, a C1-6 alkyl group, wherein the alkyl group may be substituted with a carboxy group, a halogen atom, a C1-6 alkoxy group, a carboxy group, a C1-6 alkoxycarbonyl group, C2-6 alkenyl group, wherein the C2-6 alkenyl group may be substituted with a carboxy group,
a C3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a carboxy group or an aralkoxy group,
a 5- or 6-membered aromatic heterocyclic group containing 1 or 2 hetero atoms, wherein the aromatic heterocyclic group may be substituted with a carboxy group,
a 5- or 6-membered saturated heterocyclic group containing 1 or 2 hetero atoms,
—N(Rg51)(Rg52),
wherein Rg51 and Rg52 represent the same as above,
—CON(Rg51)(Rg52),
wherein Rg51 and Rg52 represent the same as above,
—CORg53, wherein Rg53 represents the same as above, and
—COORg3, wherein Rg3 represents the same as above,
(2) an acyl group, wherein the acyl group may be substituted with a hydroxyl group,
(3) a C1-6 alkoxycarbonyl group,
(4) a C2-6 alkenyl group, wherein the alkenyl group may be substituted with a carboxy group or a halogen atom,
(5) a C3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group, —COORg3, wherein Rg3 represents the same as above, —CORg53, wherein Rg53 represents the same as above, —CONRg51Rg52, wherein Rg51 and Rg52 each represent the same as above, or a C1-6 alkyl group, wherein the alkyl group may be substituted with a carboxy group,
(6) a 5- or 6-membered saturated heterocyclic group containing 1 or 2 hetero atoms, wherein the saturated heterocyclic group may be substituted with —CORg53, wherein Rg53 represents the same as above, —COORg3, wherein Rg3 represents the same as above, —CONRg51Rg52, wherein Rg51 and Rg52 each represent the same as above or a C1-6 alkylsulfonyl group, or
(7) an aromatic carbocyclic group, wherein the aromatic carbocyclic group may be substituted with a carboxy group, a C1-6 alkyl group, wherein the alkyl group may be substituted with a carboxy group, or a C2-6 alkenyl group, wherein the alkenyl group may be substituted with a carboxy group,
or a pharmaceutically acceptable salt thereof.

354 more elements

Aminopyridine compounds having Syk inhibitory activity

Life of this patent

Aminopyridine compounds having Syk inhibitory activity

Life of this patent

Abstract

Claims13