Fused pyrimidine compound or salt thereof

1. A compound represented by Formula (I′) below or a salt thereof:

wherein in Formula (I′), A is

wherein R 1 is

halogen,

cyano,

nitro,

substituted or unsubstituted C1-C6 alkyl,

substituted or unsubstituted C1-C6 alkoxy,

substituted or unsubstituted C2-C6 alkenyl,

substituted or unsubstituted C2-C6 alkynyl,

substituted or unsubstituted amino, or

a substituted or unsubstituted 4- to 10-membered monocyclic or polycyclic unsaturated heterocyclic group containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur,

Y is N or CH, and

n is an integer of 0 to 2,

wherein when n is 2, the two R 1 may be identical or different from each other;

in Formula A2, the group:

form s, together with phenyl or pyridinyl to which this group is bonded, polycyclic C8-C14 aromatic hydrocarbon or an 8- to 14-membered polycyclic unsaturated heterocyclic group containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur;

R 2 is

substituted or unsubstituted C3-C10 alkyl,

substituted or unsubstituted C3-C4 cycloalkyl,

substituted or unsubstituted C4-C12 bridged cycloalkyl,

substituted or unsubstituted C2-C6 alkenyl,

substituted or unsubstituted C3-C4 cycloalkenyl, or

a substituted or unsubstituted 4- to 10-membered monocyclic or polycyclic saturated heterocyclic group containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur,

provided that when each group represented by R 2 has a substituent, the substituent must not be a substituted or unsubstituted saturated heterocyclic group that may have at least one identical or different heteroatom selected from oxygen and sulfur, and has at least one nitrogen atom; and

X is

N or

CR 3 , wherein R 3 is

hydrogen,

halogen,

cyano,

nitro,

substituted or unsubstituted C1-C6 alkyl,

substituted or unsubstituted C1-C6 alkoxy,

substituted or unsubstituted C1-C6 alkylthio,

substituted or unsubstituted C3-C7 cycloalkyl,

substituted or unsubstituted C2-C6 alkenyl,

substituted or unsubstituted C2-C6 alkynyl,

substituted or unsubstituted amino,

substituted or unsubstituted carbamoyl,

substituted or unsubstituted C6-C14 aromatic hydrocarbon, or

a substituted or unsubstituted 4- to 10-membered monocyclic or polycyclic saturated or unsaturated heterocyclic group containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur.

2. The compound or a salt thereof according to claim 1 , wherein when A is A1, A1 is

wherein R 1a is

C1-C6 alkyl that is unsubstituted or substituted with C1-C6 alkoxy or C1-C6 alkylthio, wherein hydrogen contained in the alkoxy may be replaced by 1 or more deuterium atoms,

C2-C6 alkenyl,

C2-C6 alkynyl,

amino that may be substituted with one or more 4- to 10-membered monocyclic or polycyclic unsaturated heterocyclic groups containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur, or C6-C14 aromatic hydrocarbon, or

a 4- to 10-membered monocyclic or polycyclic unsaturated heterocyclic group containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur;

R 1b is halogen, C1-C6 alkyl, or C1-C6 alkoxy; and

m is an integer of 0 or 1.

3. The compound or a salt thereof according to claim 1 , wherein R 2 is selected from the group consisting of:

C3-C10 alkyl that is unsubstituted or substituted with one or more substituents selected from the group consisting of halogen, C3-C7 cycloalkyl, and one or more 4- to 10-membered monocyclic or polycyclic unsaturated heterocyclic groups containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur;

C3-C4 cycloalkyl that is unsubstituted or substituted with one or more substituents selected from the group consisting of C1-C6 alkyl, C3-C7 cycloalkyl, and halogeno C1-C6 alkyl,

C4-C12 bridged cycloalkyl; and

C3-C4 cycloalkenyl.

4. The compound or a salt thereof according to claim 1 , wherein when X is CR 3 , R 3 is selected from the group consisting of:

hydrogen;

halogen;

cyano;

C1-C4 alkyl that is unsubstituted or substituted with hydroxy or oxo;

C1-C6 alkoxy that is unsubstituted or substituted with halogen, C1-C6 alkoxy, C3-C7 cycloalkyl, or one or more 4- to 10-membered monocyclic saturated heterocyclic groups that may be substituted with oxo and contain 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur;

C1-C4 alkylthio;

C3-C5 cycloalkyl;

C2-C6 alkenyl that may be substituted with hydroxyl;

C2-C6 alkynyl that is unsubstituted or substituted with a substitutent selected from the group consisting of:

hydroxy;

C1-C6 alkoxy;

amino that may be substituted with R 4 , wherein R 4 is selected from the group consisting of C1-C6 alkyl, C1-C4 alkoxy C1-C6 alkyl, and carbamoyl that is unsubstituted or substituted with C3-C7 cycloalkyl;

C1-C6 alkylsilyloxy;

C3-C7 cycloalkyl that is unsubstituted or substituted with hydroxy or oxo;

C6-C14 aromatic hydrocarbon that may be substituted with R 5 , wherein R 5 is selected from the group consisting of halogen; C1-C4 alkylamino that is unsubstituted or substituted with one or more 4- to 10-membered monocyclic unsaturated heterocyclic groups containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur; and C1-C6 alkoxy;

one or more 4- to 10-membered monocyclic saturated heterocyclic groups that may be substituted with R 6 and contain 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur, wherein R 6 is selected from the group consisting of hydroxy, C1-C6 alkyl, C1-C6 alkoxy, and oxo;

one or more 4- to 10-membered monocyclic or polycyclic unsaturated heterocyclic groups that may be substituted with R 7 and contain 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur, wherein R 7 is selected from the group consisting of halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, and amino; and

unsaturated heterocyclic oxy that is unsubstituted or substituted with halogen, wherein the unsaturated heterocyclic ring is a 4- to 10-membered monocyclic or polycyclic unsaturated heterocyclic ring containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur;

wherein the position of the triple bond of the C2-C6 alkynyl is disposed between the carbon atom bonded to the 7H-pyrrolo[2,3-d]pyrimidine skeleton and a carbon atom adjacent to the carbon atom,

C6-C14 aromatic hydrocarbon that is unsubstituted or substituted with one or more substituents selected from the group consisting of

hydroxy,

C1-C6 alkyl that may be substituted with hydroxyl,

formyl, and

one or more 4- to 10-membered monocyclic saturated heterocyclic groups that may be substituted with C1-C6 alkyl and contain 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur, and

a 4- to 6-membered monocyclic unsaturated heterocyclic group that may be substituted with one or more substituents selected from the group consisting of

halogen, and

C1-C6 alkyl that may be substituted with hydroxy, or

amino that may be substituted with C1-C6 alkyl(carbonyl), wherein said 4- to 6-membered monocyclic unsaturated heterocyclic group contains 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur.

5. The compound or a salt thereof according to claim 1 , wherein A is

wherein

R 1a is selected from the group consisting of:

C1-C6 alkyl that is unsubstituted or substituted with C1-C6 alkoxy or C1-C6 alkylthio, wherein hydrogen contained in the alkoxy may be replaced by 1 or more deuterium atoms,

C2-C6 alkenyl,

C2-C6 alkynyl,

amino that may be substituted with one or more 4- to 6-membered monocyclic unsaturated heterocyclic groups containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur, or C6-C10 aromatic hydrocarbon, or

a 4- to 6-membered monocyclic unsaturated heterocyclic group containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur;

R 1b is halogen, C1-C6 alkyl, or C1-C6 alkoxy;

m is an integer of 0 or 1;

R 2 is selected from the group consisting of:

C3-C10 alkyl that may be substituted with halogen, C3-C7 cycloalkyl, or one or more 4- to 10-membered monocyclic or polycyclic unsaturated heterocyclic groups containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur,

C3-C4 cycloalkyl that may be substituted with C1-C6 alkyl, C3-C7 cycloalkyl, or halogeno C1-C6 alkyl, and

C4-C12 bridged cycloalkyl; and

X is selected from the group consisting of:

N and

CR 3 , wherein R 3 is selected from the group consisting of

hydrogen,

halogen,

cyano,

C1-C4 alkyl,

C1-C6 alkoxy that may be substituted with one or more substituents selected from the group consisting of:

halogen,

C1-C6 alkoxy,

C3-C7 cycloalkyl, and

one or more 4- to 10-membered monocyclic saturated heterocyclic groups that may be substituted with oxo and contain 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur,

C1-C4 alkylthio,

C3-C5 cycloalkyl,

C2-C4 alkenyl that may be substituted with hydroxy,

C2-C6 alkynyl that may be substituted with one or more substituents selected from the group consisting of:

hydroxy,

C1-C4 alkoxy,

amino that may be substituted with R 4 , wherein R 4 is C1-C4 alkyl, C1-C4 alkoxy C1-C4 alkyl, or carbamoyl that may be substituted with C3-C5 cycloalkyl,

tri-C1-C6 alkylsilyloxy,

C3-C7 cycloalkyl that may be substituted with hydroxy or oxo

phenyl that may be substituted with R 5 , wherein R 5 is selected from the group consisting of halogen; methylamino that may be substituted with one or more 4- to 6-membered monocyclic unsaturated heterocyclic groups containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur; and C1-C4 alkoxy;

one or more 4- to 6-membered monocyclic saturated heterocyclic groups that may be substituted with R 6 and contain 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur, wherein R 6 is hydroxy, C1-C4 alkyl, C1-C4 alkoxy, or oxo;

one or more 4- to 10-membered monocyclic or bicyclic unsaturated heterocyclic groups that may be substituted with R 7 and contain 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur, wherein R 7 is selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 alkoxy, and amino; and

unsaturated heterocyclic oxy that may be substituted with halogen, wherein the unsaturated heterocyclic ring is a 4- to 6-membered monocyclic unsaturated heterocyclic ring containing 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur;

wherein the position of the triple bond of the C2-C6 alkynyl is disposed between the carbon atom bonded to the 7H-pyrrolo[2,3-d]pyrimidine skeleton and a carbon atom adjacent to the carbon atom;

phenyl that may be substituted with one or more substituents selected from the group consisting of:

hydroxyl,

C1-C4 alkyl that may be substituted with hydroxy,

formyl, and

one or more 4- to 6-membered monocyclic saturated heterocyclic groups that may be substituted with C1-C4 alkyl and contain 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur; and

a 4- to 6-membered monocyclic unsaturated heterocyclic group that may be substituted with one or more substituents selected from the group consisting of:

halogen,

C1-C4 alkyl that may be substituted with hydroxy, and

amino that may be substituted with C1-C4 alkyl(carbonyl),

wherein said 4- to 6-membered monocyclic unsaturated heterocyclic group contains 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur.

6. The compound or a salt thereof according to claim 1 , wherein A is

wherein R 1b is halogen;

m is an integer of 0 or 1;

R 2 is selected from the group consisting of branched C3-C6 alkyl that may be substituted with halogen, and C3-C4 cycloalkyl that may be substituted with C1-C4 alkyl or C3-C5 cycloalkyl; and

X is CR 3 , wherein R 3 is selected from the group consisting of

hydrogen;

halogen;

C1-C4 alkoxy that may be substituted with one or more substituents selected from the group consisting of:

C1-C4 alkoxy,

C3-C7 cycloalkyl, and

one or more 4- to 6-membered monocyclic saturated heterocyclic groups containing one oxygen atom;

C1-C4 alkylthio,

C2-C4 alkenyl,

C2-C6 alkynyl that may be substituted with one or more substituents selected from the group consisting of:

hydroxy;

amino that may be substituted with R 4 , wherein R 4 is C1-C4 alkyl or C1-C4 alkoxy C1-C4 alkyl;

C3-C7 cycloalkyl that may be substituted with hydroxy;

phenyl that may be substituted with R 5 , wherein R 5 is halogen,

one or more 4- to 6-membered monocyclic saturated heterocyclic groups that may be substituted with R 6 and contain 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur, wherein R 6 is hydroxy, C1-C4 alkyl, or oxo; and

one or more 4- to 10-membered monocyclic or bicyclic unsaturated heterocyclic groups that may be substituted with R 7 and contain 1 to 3 identical or different heteroatoms selected from nitrogen, oxygen, and sulfur, wherein R 7 is halogen, cyano, C1-C4 alkyl, C1-C4 alkoxy, or amino;

wherein the position of the triple bond of the C2-C6 alkynyl is disposed between the carbon atom bonded to the 7H-pyrrolo[2,3-d]pyrimidine skeleton and a carbon atom adjacent to the carbon atom;

phenyl that may be substituted with one or more substituents selected from the group consisting of hydroxy, and C1-C4 alkyl that may be substituted with hydroxyl; and

a 4- to 6-membered monocyclic unsaturated heterocyclic group containing 1 or 2 nitrogen atoms.

7. The compound according to claim 1 , selected from the group consisting of:

(1) 4-amino-7-(tert-butyl)-N-(4-(methoxymethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(2) 4-amino-7-(1-fluoro-2-methylpropan-2-yl)-N-(4-(methoxymethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(3) 4-amino-N-(4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(4) 4-amino-6-bromo-N-[4-(methoxymethyl)phenyl]-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(5) 4-amino-6-chloro-N-[4-(methoxymethyl)phenyl]-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(6) 4-amino-N-(4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-6-vinyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(7) 4-amino-6-fluoro-N-(4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(8) 4-amino-N-[4-(methoxymethyl)phenyl]-7-(1-methylcyclopropyl)-6-(3-morpholinoprop-1-yn-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(9) 4-amino-6-(4-hydroxy-4-methylpent-1-yn-1-yl)-N-[4-(methoxymethyl)phenyl]-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(10) 4-amino-N-[4-(methoxymethyl)phenyl]-7-(1-methylcyclopropyl)-6-((tetrahydro-2H-pyran-4-yl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(11) 4-amino-N-[4-(methoxymethyl)phenyl]-7-(1-methylcyclopropyl)-6-(3-(pyrrolidin-1-yl)prop-1-yn-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(12) (R)-4-amino-N-[4-(methoxymethyl)phenyl]-7-(1-methylcyclopropyl)-6-((tetrahydrofuran-2-yl)methoxy)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(13) 4-amino-N-[4-(methoxymethyl)phenyl]-6-((1-methyl-1H-pyrazol-4-yl)ethynyl)-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(14) 4-amino-6-(imidazo[1,2-b]pyridazin-3-ylethynyl)-N-[4-(methoxymethyl)phenyl]-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(15) 4-amino-N-(4-(methoxymethyl)phenyl)-6-((1-methyl-1H-pyrazol-3-yl)ethynyl)-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(16) 4-amino-N-(4-(methoxymethyl)phenyl)-6-((1-methyl-1H-imidazol-5-yl)ethynyl)-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(17) 4-amino-N-[4-(methoxymethyl)phenyl]-7-(1-methylcyclopropyl)-6-(pyridin-3-ylethynyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(18) 4-amino-N-(4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-6-(prop-1-yn-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(19) 4-amino-N-[4-(methoxymethyl)phenyl]-7-(1-methylcyclopropyl)-6-(3-(piperidin-1-yl)prop-1-yn-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(20) 4-amino-6-ethoxy-N-(4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(21) 4-amino-6-((1-hydroxycyclopentyl)ethynyl)-N-(4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(22) 4-amino-N-(4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-6-(3-thiomorpholinoprop-1-yn-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(23) 4-amino-N-(4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-6-(3-(tetrahydro-2H-pyran-4-yl)prop-1-yn-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(24) 4-amino-6-((6-aminopyridin-3-yl)ethynyl)-N-(4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(25) 4-amino-6-((1,3-dimethyl-1H-pyrazol-4-yl)ethynyl)-N-(4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(26) 4-amino-N-(4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-6-((1-methylpiperidin-4-yl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(27) 4-amino-6-(3-(dimethylamino)prop-1-yn-1-yl)-N-(4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;

(28) 4-amino-N-(3-fluoro-4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-6-((tetrahydro-2H-pyran-4-yl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide; and

(29) 4-amino-N-(3-fluoro-4-(methoxymethyl)phenyl)-7-(1-methylcyclopropyl)-6-(3-morpholinoprop-1-yn-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide; and

salts of these compounds.

8. A pharmaceutical composition comprising the compound or a salt thereof according to claim 1 .

9. A pharmaceutical composition comprising the compound or a salt thereof according to claim 7 in combination with a pharmaceutical carrier.