Nitrogen-containing condensed cyclic compound having a pyrazolyl group as a substituent group and pharmaceutical composition thereof

A pharmaceutical composition comprising:

• a compound represented by the following formula (I), a salt thereof or a hydrate of them, and
• a pharmaceutically acceptable carrier;
• wherein in the formula, X represents quinoline, isoquinoline, quinazoline or imidazopyridine, and said X has (R4)n as substituent groups whereupon n is 0, 1, 2 or 3, and the substituent groups R4 independently represent a hydrogen atom, halogen atom, cyano group, hydroxyl group, amino group, C1-6 alkyl group, halogenated C1-6 alkyl group, C2-6 alkenyl group, C1-6 alkylsulfonyl group, C1-6 alkylsulfonylamino group, C1-6 alkylsulfinyl group, N—(C1-6 alkyl)amino group, N,N-di(C1-6 alkyl)amino group, C1-6 alkoxy group, C1-6 alkylsulfanyl group, carbamoyl group, N—(C1-6 alkyl)carbamoyl group, N,N-di(C1-6 alkyl)carbamoyl group, sulfamoyl group, phenyl group, heteroaryl group, phenoxy group, heteroallyloxy group, phenyl C1-6 alkylamino group or heteroaryl C1-6 alkylamino group, which is bound to an atom constituting X;
• Y represents a phenyl group, piperazine, pyridine, thiophene, thiazole, oxadiazole or oxathiadiazole;
• (Z)n are n (Z) groups bound to Y, whereupon n is 0, 1, 2 or 3, Z groups are bound to an atom constituting the cyclic group Y and independently represent formula —M1—M2—M3 wherein:
• M1 and M2 each represent a single bond, —(CH2)m—, —CHR5CHR6—, —(CH2)m—CR5R6—(CH2)n—, —CR5═CR6—, —C≡C—, —CR5═CR6—CO—, (CH2)m—O—(CH2)n—, —O—(CH2)n—CR5R6—, —(CH2)m—S—(CH2)n—, —SO(CH2)m—, —SO2(CH2)m—, —CO(CH2)m—, —COO—, —CONR7—, —CONR7CHR8—, —CONR7—CR5R6—, —CONR7—(CH2)m—, —NR7—, —NR7CO—CR5R6—, —NR7CO—CR5R6—CO—, —NR7CO—(CH2)m—, —NR7SO2(CH2)m—, —SO2NR7—(CH2)m—, —SO2NR7—CR5R6—, —NR7CONR8—, or —NR7CSNR8— whereupon n and m are independently 0, 1, 2 or 3, or a group selected from (a) C6-14 aromatic hydrocarbon cyclic group, (b) C3-14 cycloalkyl group, (c) C4-14 cycloalkenyl group, (d) 5- to 14-membered aromatic heterocyclic group, or (e) 4- to 14-membered non-aromatic heterocyclic group, each of which may be substituted with 4 or less groups selected from the substituent group Q,
• M3 represents (i) hydrogen atom, (ii) oxo group, (iii) halogen atom, (iv) hydroxyl group, (v) amino group, (vi) cyano group, (vii) nitro group, (viii) azido group, (viv) cyano group, (x) carboxyl group, (xi) C1-6 alkyl group, (xii) halogenated C1-6 alkyl group, (xiii) C1-6 alkyl group substituted with a hydroxyl or cyano group, (xiv) C2-6 alkenyl group, (xv) C2-6 alkynyl group, (xvi) halogenated C2-6 alkenyl group, (xvii) halogenated C1-6 alkoxy group, (xviii) —OR7, (xviv) —NR7R8, (xx) —NR7COR8, (xxi) —COR7, (xxii) —CONR7R8, (xxiii) —SOR7, (xxiv) —SO2R7, (xxv) —NR7SO2R8, (xxvi) —SO2NR7R8, (xxvii) methylene dioxy group, (xxviii) ethylene dioxy group, or (xxviv) (a) C3-8 cycloalkyl group, (b) C4-8 cycloalkenyl group, (c) 5- to 14-membered non-aromatic heterocyclic group, (d) C6-14 aromatic hydrocarbon cyclic group, (e) 5- to 14-membered aromatic heterocyclic group, (f) phenoxy group, (g) heteroallyoxy group or (h) C3-8 cycloalkyloxy group, which may be substituted with 4 or less groups selected from the substituent group Q;
• the substituent group Q represents an oxo group, halogen atom, hydroxyl group, amino group, cyano group, nitro group, azido group, carboxyl group, C1-6 alkyl group, halogenated C1-4 alkyl group, C1-6 alkyl group substituted with a hydroxyl or cyano group, C2-6 alkenyl group, C2-6 alkynyl group, halogenated C2-6 alkenyl group, halogenated C1-6 alkoxy group, —OR7, —OCH2CONR7R8, —NR7R8, —NR7COR8, —COR7, —CONR7R8, —SOR7, —SO2R7, NR7SO2R8, —SO2NR7R8, methylene dioxy group or ethylene dioxy group (wherein R7 and R8 are the same as or different from each other and each represents a hydrogen atom, a C1-6 alkyl group or a C3-8 cyloalkyl group);
• R1 represents (1) hydrogen atom, (2) halogen atom, (3) hydroxyl group, (4) nitro group, (5) cyano group, (6) halogenated C1-6 alkyl group, (7) C2-6 alkyl group substituted with a hydroxyl or cyano group, (8) C2-6 alkenyl group, or (9) formula —L1—L2—L3,
• wherein 1) —L1 represents a single bond, —(CH2)m—, —(CH2)m—CR5R6—(CH2)n—, —CR5═CR6—, —CH═CR5—CO—, —(CH2)m—O—(CH2)n—, —CO(CH2)m—, —COO—, —NR7—, —CO—NR7—, —NR7CO—, —NR7CO—(CH2)m—, —NR7CONR8—, whereupon n and m are independently 0, 1, 2 or 3, or (a) C3-8 cycloalkyl group, (b) C4-8 cycloalkenyl group, (c) 5- to 14-membered non-aromatic heterocyclic group, (d) C6-14 aromatic hydrocarbon cyclic group or (e) 5- to 14-membered aromatic heterocyclic group, which may be substituted with 4 or less substituent groups selected from the substituent group Q;
• 2) L represents a single bond, —(CH2)m—, —CR5R6—, —(CH2)m—CR5R6—(CH2)n—, —CR5═CR6—, —C≡C—, —CR═CR5—CO—, —O—, —S—, —SO—, —SO2—, —SO2—(CH2)m—, —(CH2)m—O—(CH2)n—, —O—(CH2)n—CR5R6—, —CO—(CH2)m—, —COO—, —NR7, —CO—NR7—, —CO—NR7(CH2)m—, —NR7CO—, —NR7CO—(CH2)m—, —NR7SO2—, —SO2NR7—, —NR7CONR8—, or —NR7CSNR8— whereupon n and m are independently 0, 1, 2 or 3, or (a) C3-8 cycloalkyl group, (b) C4-8 cycloalkenyl group, (c) 5- to 14-membered non-aromatic heterocyclic group, (d) C6-14 aromatic hydrocarbon cyclic group or (e) 5- to 14-membered aromatic heterocyclic group, which may be substituted with 4 or less substituent groups selected from the substituent group Q;
• 3) L3 represents (i) hydrogen atom, (ii) oxo group, (iii) halogen atom, (iv) hydroxyl group, (v) amino group, (vi) cyano group, (vii) nitro group, (viii) azido group, (viv) cyano group, (x) carboxyl group, (xi) C1-6 alkyl group, (xii) halogenated C1-6 alkyl group, (xiii) C1-6 alkyl group substituted with a hydroxyl or cyano group, (xiv) C2-6 alkenyl group, (xv) C2-6 alkynyl group, (xvi) halogenated C2-6 alkenyl group, (xvii) halogenated C1-6 alkoxy group, (xviii) —OR7, (xviv) —NR7R8, (xx) —NR7COR8, (xxi) —COR7, (xxii) —CONR7R8, (xxiii) —SOR7, (xxiv) —SO2R7, (xxv) —NR7SO2R8, (xxvi) —SO2NR7R8, (xxvii) methylene dioxy group, (xxviii) ethylene dioxy group, or (xxviv) (a) C3-8 cycloalkyl group, (b) C4-8 cycloalkenyl group, (c) 5- to 14-membered non-aromatic heterocyclic group, (d) C6-14 aromatic hydrocarbon cyclic group, (e) 5- to 14-membered aromatic heterocyclic group, (f) phenoxy group, (g) heteroallyoxy group or (h) C3-8 cycloalkyloxy group, each of which may be substituted with 4 or less groups selected from the substituent group Q;
• R2 represents a hydrogen atom;
• R3 represents a hydrogen atom, halogen atom, cyano group, amino group, C1-4 alkyl group or halogenated C1-4 alkyl group,
• wherein the above-mentioned R5 and R6 are the same or different and each represent 1) hydrogen atom, 2) halogen atom, 3) hydroxyl group, 4) cyano group, 5) C1-6 alkyl group, 6) C1-6 alkyl group substituted with a halogen atom, hydroxy group or cyano group, 7) C3-8 cycloalkyl group, 8) phenyl group which may be substituted with 3 or less groups selected from the substituent group Q, 9) 5- to 6-membered aromatic heterocyclic group which may be substituted with 3 or less groups selected from the substituent group Q, or 10) C3-8 cycloalkyl group formed by combining R5 with R6, and
• the above-mentioned R7 and R8 are the same or different and each represent a hydrogen atom, C1-6 alkyl group, halogenated C1-6 alkyl group, C3-8 cycloalkyl group, phenyl group or 5- to 6-membered aromatic heterocyclic group.

A compound represented by the following formula (I), or a salt thereof or a hydrate thereof:

• wherein X represents quinoline, isoquinoline, quinazoline or imidazopyridine, and said X has (R4)n as substituent groups whereupon n is 0, 1, 2 or 3, and the substituent groups (R4)n independently represent a hydrogen atom, halogen atom, cyano group, hydroxyl group, amino group, C1-6 alkyl group, halogenated C1-6 alkyl group, C2-6 alkenyl group, C1-6 alkylsulfonyl group, C1-6 alkylsulfonylamino group, C1-6 alkylsulfinyl group, N—(C1-6 alkyl)amino group, N,N-di(C1-6 alkyl)amino group, C1-6 alkoxy group, C1-6 alkylsulfanyl group, carbamoyl group, N—(C1-6 alkyl)carbamoyl group, N,N-di(C1-6 alkyl)carbamoyl group, sulfamoyl group, phenyl group, heteroaryl group, phenoxy group, heteroallyloxy group, phenyl C1-6 alkylamino group or heteroaryl C1-6 alkylamino group, which is bound to an atom constituting X;
• Y represents a phenyl group, piperazine, pyridine, thiophene, thiazole, oxadiazole or oxathiadiazole;
• (Z)n are n (Z) groups bound to Y, whereupon n is 0, 1, 2 or 3, Z groups are bound to an atom constituting the cyclic group Y and independently represent a group selected from the group consisting of (1) hydrogen atom, (2) amino group, (3) halogen atom, (4) hydroxyl group, (5) nitro group, (6) cyano group, (7) azido group, (8) formyl group, (9) hydroxyamino group, (10) sulfamoyl group, (11) guanodino group, (12) oxo group, (13) C2-6 alkenyl group, (14) C1-6 alkoxy group, (15) C1-6 alkylhydroxyamino group, (16) halogenated C1-6 alkyl group and (17) halogenated C2-6 alkenyl group;
• R1 represents (1) hydrogen atom, (2) halogen atom, (3) hydroxyl group, (4) nitro group, (5) cyano group, (6) halogenated C1-6 alkyl group, (7) C2-6 alkyl group substituted with a hydroxyl or cyano group, (8) C2-6 alkenyl group, or (9) formula —L1—L2—L3,
• wherein 1) —L1 represents a single bond, —(CH2)m—, —(CH2)m—CR5R6—CH2)n—, —CR5═CR6—, —CH═CR5—CO—, —(CH2)m—O—(CH2)n—, —CO(CH2)m—, —COO—, —NR7—, —CO—NR7—, —NR7CO—, —NR7CO—(CH2)m—, —NR7CONR8—, whereupon n and m are independently 0, 1, 2 or 3, or (a) C3-8 cycloalkyl group, (b) C4-8 cycloalkenyl group, (c) 5- to 14-membered non-aromatic heterocyclic group, (d) C6-14 aromatic hydrocarbon cyclic group or (e) 5- to 14-membered aromatic heterocyclic group, which may be substituted with 4 or less substituent groups selected from the substituent group Q;
• 2) L2 represents a single bond, —(CH2)m—, —CR5R6—, —(CH2)m—CR5R6—(CH2)n—, —CR5═CR6—, —C≡C—, —CR═CR5—CO—, —O—, —S—, —SO—, —SO2—, —SO2—(CH2)m—, —(CH2)m—O—(CH2)n—, —O—(CH2)n—CR5R6—, —CO—(CH2)m—, —COO—, —NR7—, —CO—NR7—, —CO—NR7(CH2)m—, —NR7CO—, —NR7CO—(CH2)m—, —NR7SO2—, —SO2NR7—, —NR7CONR8—, or —NR7CSNR8— whereupon n and m are independently 0, 1, 2 or 3, or (a) C3-8 cycloalkyl group, (b) C4-8 cycloalkenyl group, (c) 5- to 14-membered non-aromatic heterocyclic group, (d) C6-14 aromatic hydrocarbon cyclic group or (e) 5- to 14-membered aromatic heterocyclic group which may be substituted with 4 or less substituent groups selected from the substituent group Q;
• 3) L3 represents (i) hydrogen atom, (ii) oxo group, (iii) halogen atom, (iv) hydroxyl group, (v) amino group, (vi) cyano group, (vii) nitro group, (viii) azido group, (viv) cyano group, (x) carboxyl group, (xi) C1-6 alkyl group, (xii) halogenated C1-6 alkyl group, (xiii) C1-6 alkyl group substituted with a hydroxyl or cyano group, (xiv) C2 alkenyl group, (xv) C2-6 alkynyl group, (xvi) halogenated C2-6 alkenyl group, (xvii) halogenated C1-6 alkoxy group, (xviii) —OR7, (xviv) —NR7R8, (xx) —NR7COR8, (xxi) —COR7, (xxii) —CONR7R8, (xxiii) —SOR7, (xxiv) —SO2R7, (xxv) —NR7SO2R8, (xxvi) —SO2NR7R8, (xxvii) methylene dioxy group, (xxviii) ethylene dioxy group, or (xxviv) (a) C3-8 cycloalkyl group, (b) C4-8 cycloalkenyl group, (c) 5- to 14-membered non-aromatic heterocyclic group, (d) C6-14 aromatic hydrocarbon cyclic group, (e) 5- to 14-membered aromatic heterocyclic group, (f) phenoxy group, (g) heteroallyoxy group or (h) C3-8 cycloalkyloxy group, which may be substituted with 4 or less groups selected from the substituent group Q;
• and
• the substituent group Q represents an oxo group, halogen atom, hydroxyl group, amino group, cyano group, nitro group, azido group, carboxyl group, C1-6 alkyl group, halogenated C1-6 alkyl group, C1-6 alkyl group substituted with a hydroxyl or cyano group, C2-6 alkenyl group, C2-6 alkynyl group, halogenated C2-6 alkenyl group, halogenated C1-6 alkoxy group, —OR7, —OCH2CONR7R8, —NR7R8, —NR7COR8, —COR7, —CONR7R8, —SOR7, —SO2R7, —NR7SO2R8, —SO2NR7R8, methylene dioxy group or ethylene dioxy group;
• R2 represents a hydrogen atom or a group for protecting pyrazole nitrogen,
• R3 represents a hydrogen atom, halogen atom, cyano group, amino group, C1-4 alkyl group or halogenated C1-4 alkyl group,
• wherein the above-mentioned R5 and R6 are the same or different and each represent 1) hydrogen atom, 2) halogen atom, 3) hydroxyl group, 4) cyano group, 5) C1-6 alkyl group, 6) C1-6 alkyl group substituted with a halogen atom, hydroxy group or cyano group, 7) C3-8 cycloalkyl group, 8) phenyl group which may be substituted with 3 or less groups selected from the substituent group Q, 9) 5- to 6-membered aromatic heterocyclic group which may be substituted with 3 or less groups selected from the substituent group Q, or 10) C3-8 cycloalkyl group formed by combining R5 with R6, and
• the above-mentioned R7 and R8 are the same or different and each represent a hydrogen atom, C1-6 alkyl group, halogenated C1-6 alkyl group, C3-8 cycloalkyl group, phenyl group or 5 to 6-membered aromatic heterocyclic group.