Pyrazolo[3,4-d]pyrimidine compound or salt thereof

1. A compound of the following formula (I) or a salt thereof:

wherein X represents an optionally substituted 4- to 10-membered nitrogen-containing saturated heterocyclic group;

Y represents —C(R 4 )═C(R 5 )(R 6 );

Z 1 , Z 2 , Z 3 , and Z 4 are the same as or different from each other and each represent a hydrogen atom, a halogen atom, a cyano group, a C2-C6 alkenyl group, an optionally substituted C1-C6 alkoxy group, an optionally substituted C1-C6 alkyl group, an optionally substituted amino group, an optionally substituted C3-C7 cycloalkyl group, a C6-C14 aromatic hydrocarbon group, or a 4- to 14-membered unsaturated heterocyclic group, or Z 1 and Z 2 , or Z 3 and Z 4 optionally form, together with the respective carbon atoms bonded thereto, a benzene ring or a 5- to 7-membered saturated or unsaturated heterocyclic ring;

W represents —CH 2 —, an oxygen atom, or —NH—;

n represents an integer of from 0 to 2;

R 1 represents an optionally substituted amino group;

R 2 and R 3 are the same as or different from each other and each represent a hydrogen atom, an optionally substituted C1-C6 alkoxy group, an optionally substituted C1-C6 alkyl group, or an optionally substituted C6-C14 aromatic hydrocarbon group, or R 2 and R 3 optionally form, together with the nitrogen atom bonded thereto, an optionally substituted 4- to 8-membered nitrogen-containing saturated heterocyclic group; and

R 4 , R 5 , and R 6 are the same as or different from each other and each represent a hydrogen atom or an optionally substituted C1-C6 alkyl group.

2. The compound according to claim 1 or a salt thereof, wherein

in the formula (I),

X is a 4- to 10-membered nitrogen-containing saturated heterocyclic group optionally having a halogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group, or an amino group as a substituent;

Z 1 , Z 2 , Z 3 , and Z 4 are the same as or different from each other and each are a hydrogen atom, a halogen atom, a cyano group, a C2-C6 alkenyl group, an optionally substituted C1-C6 alkoxy group, an optionally substituted C1-C6 alkyl group, an optionally substituted amino group, an optionally substituted C3-C7 cycloalkyl group, or a 4- to 14-membered unsaturated heterocyclic group, or Z 1 and Z 2 , or Z 3 and Z 4 optionally form, together with the respective carbon atoms bonded thereto, a benzene ring or a 5- to 7-membered saturated or unsaturated heterocyclic ring;

n is 0; and

R 1 is an amino group.

3. The compound according to claim 1 or a salt thereof, wherein

in the formula (I),

X is a 4- to 8-membered nitrogen-containing saturated heterocyclic group optionally having a halogen atom or a C1-C6 alkyl group as a substituent;

Y is —C(R 4 )═C(R 5 )(R 6 );

Z 1 , Z 2 , Z 3 , and Z 4 are the same as or different from each other and each are a hydrogen atom, a halogen atom, a cyano group, a C2-C6 alkenyl group, an optionally halogen atom-substituted C1-C6 alkoxy group, a C1-C6 alkyl group, an optionally C1-C6 alkyl group-substituted amino group, a C3-C7 cycloalkyl group, or a monocyclic 4- to 6-membered unsaturated heterocyclic group having one oxygen atom, or Z 1 and Z 2 , or Z 3 and Z 4 optionally form, together with the respective carbon atoms bonded thereto, a benzene ring or a 5- to 7-membered saturated or unsaturated heterocyclic ring;

W is —CH 2 —, an oxygen atom, or —NH—;

n is 0;

R 1 is an amino group;

R 2 and R 3 are the same as or different from each other and each are a hydrogen atom, a C1-C6 alkoxy group, a C1-C6 alkyl group, or a C6-C14 aromatic hydrocarbon group, or R 2 and R 3 optionally form, together with the nitrogen atom bonded thereto, an optionally hydroxyl group-substituted 4- to 8-membered nitrogen-containing saturated heterocyclic group; and

R 4 , R 5 , and R 6 are the same as or different from each other and each are a hydrogen atom or an optionally di(C1-C6 alkyl)amino group-substituted C1-C6 alkyl group.

4. The compound according to claim 1 or a salt thereof, wherein

in the formula (I),

X is a pyrrolidinyl group optionally having a C1-C6 alkyl group as a substituent, or a piperidinyl group optionally having a halogen atom as a substituent;

Y is —C(R 4 )═C(R 5 )(R 6 ); and

R 4 , R 5 , and R 6 are the same as or different from each other and each are a hydrogen atom or a dimethylaminomethyl group.

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

in the formula (I),

X is a pyrrolidinyl group, a methylpyrrolidinyl group, a piperidinyl group, or a fluoropiperidinyl group;

Y is

and

R 2 and R 3 are the same as or different from each other and each are a hydrogen atom, a methoxy group, a methyl group, or a phenyl group, or R 2 and R 3 optionally form, together with the nitrogen atom bonded thereto, an azetidinyl group optionally having a hydroxyl group as a substituent, a pyrrolidinyl group, or a piperidinyl group.

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

in the formula (I),

X is a pyrrolidinyl group, a methylpyrrolidinyl group, a piperidinyl group, or a fluoropiperidinyl group;

Y is

Z 1 , Z 2 , Z 3 , and Z 4 are the same as or different from each other and each are a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a cyano group, a vinyl group, a methoxy group, a fluoromethoxy group, a difluoromethoxy group, a methyl group, an ethyl group, a dimethylamino group, a cyclopropyl group, or a furyl group, or Z 1 and Z 2 or Z 3 and Z 4 optionally form, together with the respective carbon atoms bonded thereto, a benzene ring, a pyridine ring, or a dioxolane ring;

W is —CH 2 —, an oxygen atom, or —NH—;

n is 0;

R 1 is an amino group; and

R 2 and R 3 are the same as or different from each other and each are a methoxy group, a methyl group, or a phenyl group, or R 2 and R 3 optionally form, together with the nitrogen atom bonded thereto, a hydroxyazetidinyl group, a pyrrolidinyl group, or a piperidinyl group.

7. The compound according to claim 1 or a salt thereof, wherein the compound is selected from the group consisting of the following (1) to (20):

(1) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(5-bromo-4-(2-(dimethylamino)-2-oxoethyl)-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(2) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(2-chloro-4-(2-(dimethylamino)-2-oxoethyl)-5-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(3) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(2-chloro-4-(2-(dimethylamino)-2-oxoethyl)-3-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(4) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(4-(2-(dimethylamino)-2-oxoethyl)-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(5) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(4-(2-(dimethylamino)-2-oxoethyl)naphthalen-1-yl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(6) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(2-chloro-4-(2-(dimethylamino)-2-oxoethyl)phenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(7) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(4-(2-(dimethylamino)-2-oxoethyl)-2-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(8) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(3-chloro-4-(2-(dimethylamino)-2-oxoethyl)phenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(9) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(5-chloro-4-(2-(dimethylamino)-2-oxoethyl)-2-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(10) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(4-(2-(dimethylamino)-2-oxoethyl)-5-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(11) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(3-chloro-4-(2-(dimethylamino)-2-oxoethyl)-2-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(12) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(4-(2-(dimethylamino)-2-oxoethyl)-3-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(13) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(4-(2-(dimethylamino)-2-oxoethyl)-2,3-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(14) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(4-(2-(dimethylamino)-2-oxoethyl)-3-fluoro-2-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(15) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(2-(difluoromethoxy)-4-(2-(dimethylamino)-2-oxoethyl)phenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(16) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(4-(2-(dim ethyl amino)-2-oxoethyl)-2-(fluoromethoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(17) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(2-bromo-4-(2-(dimethylamino)-2-oxoethyl)phenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(18) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(2-chloro-4-(2-(dimethylamino)-2-oxoethyl)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide,

(19) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(5-chloro-4-(2-(dimethylamino)-2-oxoethyl)-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide, and

(20) (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(2,5-dichloro-4-(2-(dimethylamino)-2-oxoethyl)phenyl)-1H-pyrazol o[3,4-d]pyrimidine-3-carboxamide.

8. A pharmaceutical composition comprising the compound according to claim 1 or a salt thereof, and a pharmaceutically acceptable carrier.