Heterocyclic Compound as a Protein Kinase Inhibitor

A compound represented by a following formula 1, a stereoisomer thereof or a pharmaceutically acceptable salt thereof:

• wherein
• X is C-A3 or N;
• Y is C-A4 or N;
• Z is N or N—O;
• A1 to A4 are each independently H or C1-C6 alkyl, C1-C6 alkoxy, C1-C6 hydroxyalkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C(═O)—OH, C(═O)—O—C1-C6 alkyl, S(═O)2—C1-C6 alkyl, aryl or heteroaryl;
• B1 is —(CH2)m—, —C(═O)—, —C(═S)—, —C(═NR1)—, —C(═O)—NR1—, —S(═O)2— or null, wherein at least one H of —(CH2)m— may be substituted with C1-C6 alkyl, halogen or cyano, or may be linked to each other along with at least one carbon atom to form a ring;
• B2 is H, C1-C6 alkyl, C3-C7 cycloalkyl, 5-6 membered heterocycloalkyl, aryl, heteroaryl, C1-C6 alkyl-aryl or C1-C6 alkyl-heteroaryl, wherein at least one H of C3-C7 cycloalkyl, 5-6 membered heterocycloalkyl, aryl, heteroaryl, C1-C6 alkyl-aryl or C1-C6 alkyl-heteroaryl may be substituted with C1-C6 alkyl, hydroxy or halogen;
• B3 is H or C1-C6 alkyl;
• Cyclic linker is C3-C7 cycloalkyl, C3-C7 cycloalkenyl, 5-6 membered heterocycloalkyl, 5-6 membered heterocycloalkenyl, aryl or heteroaryl;
• C1 and C2 are each independently H, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 hydroxyalkyl, C1-C6 cyanoalkyl, C1-C6 haloalkyl, hydroxy, cyano, halogen, C(═O)—OH, C(═O)—O—C1-C6 alkyl, S(═O)2—C1-C6 alkyl, aryl or heteroaryl,
• or C1 and C2 may be linked to each other through at least one carbon atom to make a bicyclic ring or spiro ring;
• D1 is —(CH2)m—, —(CH2)m—NR1—, —NR1—, —O—,
• or null, wherein at least one H of —(CH2)m— or —(CH2)m—NR1— may be substituted with C1-C6 alkyl, halogen or cyano, or may be linked to each other along with at least one carbon atom to form a ring;
• and at least one H of
• may be substituted with C1-C6 alkyl, C1-C6 hydroxyalkyl, C1-C6 haloalkyl or C1-C6 cyanoalkyl;
• D2 is —C(═O)—, —C(═O)—CH2—C(═O)—, —C(═S)—, —S(═O)2— or null, wherein at least one H of —C(═O)—CH2—C(═O)— may be substituted with C1-C6 alkyl or halogen;
• D3 is —(CH2)m—, —(CH2)m—NR1—, —NR1—, —O—,
• or null, wherein at least one H of —(CH2)m— or —(CH2)m—NR1— may be substituted with C1-C6 alkyl, halogen or cyano, or may be linked to each other along with at least one carbon atom to form a ring;
• D4 is H, C1-C6 alkyl, C1-C6 alkenyl, C1-C6 alkoxyalkyl, C1-C6 hydroxyalkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, S(═O)2—C1-C6 alkyl, C3-C7 cycloalkyl,
• aryl or heteroaryl,
• wherein at least one H of C1-C6 alkyl, C1-C6 alkenyl, C1-C6 alkoxyalkyl, C1-C6 hydroxyalkyl, C1-C6 haloalkyl or C1-C6 cyanoalkyl may be substituted with C3-C7 cycloalkyl;
• at least one H of C3-C7 cycloalkyl or
• may be substituted with C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, cyano, halogen, —C(═O)—R4 or —C(═O)—O—R4;
• and
• at least one H of aryl or heteroaryl may be substituted with C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C1-C6 cyanoalkyl, C1-C6 thioalkyl, hydroxy, cyano, nitro, halogen, —C(═O)—R4, —C(═O)—NR1—R4, —S(═O)2—R4, —S(═O)2—NR1—R4, —NR1—R5,
• aryl or heteroaryl, wherein, at this time, at least one H of
• may be substituted with C1-C6 alkyl or (═O));
• R1 and R2 are each independently H or C1-C6 alkyl;
• R3 is H, C1-C6 alkyl, —C(═O)—R4, —C(═O)—O—R4, —S(═O)2—R4 or —S(═O)2—NR1—R4, wherein in case W is —O—, —C(═O)— or —S(═O)2—, R3 is null;
• R4 is H, C1-C6 alkyl or C1-C6 haloalkyl;
• R5 is H, C1-C6 alkyl,
• aryl or heteroaryl, wherein at least one H of
• may be substituted with C1-C6 alkyl or (═O);
• and at least one H of aryl or heteroaryl may be substituted with C1-C6 alkyl or halogen;
• V is —CH— or —N—;
• W is —CH—, —N—, —O—, —S—, —C(═O)—, —S(═O)— or —S(═O)2—, wherein in case V is —CH—, W is not —CH—;
• a to d are each independently 1, 2 or 3;
• and
• m is 1, 2 or 3.