Benzo-fused 5-membered heterocyclic compounds, their production and use

Abstract

A compound represented by the formula: (wherein, R 1 and R 2 are the same or different and each represents a hydrogen atom, hydrocarbon group or heterocyclic group, or R 1 and R 2 may form, together with the adjacent carbon atom, a 3-8 membered iso- or heterocyclic group, R 3 represents a cyclic group, a hydroxy group, a mercapto group that may have oxo, or an amino group, R 4 represents a hydrogen atom, a hydrocarbon group, a hydroxy group, a mercapto group which may have oxo, or an amino group, or R 2 and R 4 may link together to form a double bond, X represents a bond or a linear hydrocarbon group, W represents an oxygen atom or a sulfur atom, ring B represents a 5-8 membered nitrogen-containing heterocyclic group, ring C represents a benzene ring, and represents a single bond or a double bond), or a salt or a prodrug thereof that has excellent neurodegenerative inhibitory activity and brain penetrability, and is useful as an agent for preventing/treating neurodegenerative diseases.

1 . Compounds represented by formula:  
     
       
         
         
             
             
         
       
       (wherein, R 1  and R 2  are the same or different and each represents a hydrogen atom, optionally substituted hydrocarbon group or optionally substituted heterocyclic group, or R 1  and R 2  may form, together with the adjacent carbon atom, a 3-8 membered iso- or heterocyclic group which may optionally substituted, R 3  represents an optionally substituted cyclic group, X represents a bond or a spacer of 1-3 atoms, and R 4  represents a hydrogen atom, an optionally substituted hydrocarbon group, optionally substituted hydroxy group, optionally substituted mercapto group which may have oxo, or an optionally substituted amino group, or R 2  and R 4  may link together to form a double bond, W represents an oxygen atom or a sulfur atom, ring B represents an optionally substituted 4-8 membered nitrogen-containing heterocyclic group, and ring C represents a benzene ring which may also be optionally substituted in addition to the group represented by ring B but not via a nitrogen atom, and   represents a single bond or a double bond), or a salt thereof.  
     
   
   
       2 . The compounds as defined in  claim 1 , wherein R 1  and R2 are the same or different and represent (i) a hydrogen atom, (ii) C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C3-8 cycloalkyl group or C6-14 aryl group each of which may have 1-5 substituents selected from (1) halogen, (2) C1-3 alkylenedioxy, (3) nitro, (4) cyano, (5) optionally halogenated C1-6 alkyl, (6) optionally halogenated C2-6 alkenyl, (7) optionally halogenated C2-6 alkynyl, (8) optionally halogenated C3-8 cycloalkyl, (9) optionally halogenated C6-14 aryl, (10) optionally halogenated C1-6 alkoxy, (11) optionally halogenated C1-6 alkylthio or mercapto, (12) hydroxy, (13) amino, (14) mono-C1-6 alkylamino, (15) mono-C6-14 arylamino, (16) di-C1-6 alkylamino, (17) di-C6-14 arylamino, (18) acyl selected from formyl, carboxy, carbamoyl, C1-6 alkyl-carbonyl, C3-8 cycloalkyl-carbonyl, C1-6 alkoxy-carbonyl, C6-14 aryl-carbonyl, C7-16 aralkyl-carbonyl, C6-14 aryloxy-carbonyl, C7-16 aralkyloxy-carbonyl, 5- or 6-membered heterocyclic carbonyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, mono-C1-6 alkyl-carbamoyl, di-C1-6 alkyl-carbamoyl, C6-14 aryl-carbamoyl, thiocarbamoyl, 5- or 6-membered heterocyclic carbamoyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, C1-6 alkylsulfonyl, C6-14 arylsulfonyl, C1-6 alkylsulfinyl and C6-14 arylsulfinyl, (19) acylamino selected from formyl amino, C1-6 alkyl-carboxamide, C6-14 aryl-carboxamide, C1-6 alkoxy-carboxamide, C1-6 alkylsulfonyl amino and C6-14 arylsulfonyl amino, (20) acyloxy which is selected from C1-6 alkyl-carbonyloxy, C6-14 aryl-carbonyloxy, C1-6 alkoxy-carbonyloxy, mono-C1-6 alkyl-carbamoyloxy, di-C1-6 alkyl-carbamoyloxy, C6-14 aryl-carbamoyloxy and nicotinoyloxy, (21) 4-8 membered saturated cyclic amino which may contain 1-3 substituents selected from C1-6 alkyl, C6-14 aryl, and a 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (22) 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (23) sulfo and (24) C6-14 aryloxy, or (iii) 5-14 membered heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, optionally containing 1-5 substituents selected from (1) halogen, (2) C1-3 alkylenedioxy, (3) nitro, (4) cyano, (5) optionally halogenated C1-6 alkyl, (6) optionally halogenated C2-6 alkenyl, (7) optionally halogenated C2-6 alkynyl, (8) optionally halogenated C3-8 cycloalkyl, (9) optionally halogenated C6-14 aryl, (10) optionally halogenated C1-6 alkoxy, (11) optionally halogenated C1-6 alkylthio or mercapto, (12) hydroxy, (13) amino, (14) mono-C1-6 alkylamino, (15) mono-C6-14 arylamino, (16) di-C1-6 alkylamino, (17) di-C6-14 arylamino, (18) acyl which is selected from formyl, carboxy, carbamoyl, C1-6 alkyl-carbonyl, C3-8 cycloalkyl-carbonyl, C1-6 alkoxy-carbonyl, C6-14 aryl-carbonyl, C7-16 aralkyl-carbonyl, C6-14 aryloxy-carbonyl, C7-16 aralkyloxy-carbonyl, 5- or 6-membered heterocyclic carbonyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, mono-C1-6 alkyl-carbamoyl, di-C1-6 alkyl-carbamoyl, C6-14 aryl-carbamoyl, thiocarbamoyl, 5- or 6-membered heterocyclic carbamoyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, C1-6 alkylsulfonyl, C6-14 arylsulfonyl, C1-6 alkylsulfinyl and C6-14 arylsulfinyl, (19) acylamino selected from formyl amino, C1-6 alkyl-carbonylamino, C6-14 aryl-carbonylamino, C1-6 alkoxy-carbonylamino, C1-6 alkylsulfonyl amino and C6-14 arylsulfonyl amino, (20) acyloxy which is selected from C1-6 alkyl-carbonyloxy, C6-14 aryl-carbonyloxy, C1-6 alkoxy-carbonyloxy, mono-C1-6 alkyl-carbamoyloxy, di-C1-6 alkyl-carbamoyloxy, C6-14 aryl-carbamoyloxy and nicotinoyloxy, (21) 4-8 membered saturated cyclic amino optionally containing 1-3 substituents selected from C1-6 alkyl, C6-14 aryl and 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (22) 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (23) sulfo, and (24) C6-14 aryloxy, or 
 (iv) R1 and R2, together with the adjacent carbon atom, may form C3-8 cycloalkane or 3-8 membered heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, which may respectively include 1-5 substituents selected from the following, (1) halogen, (2) C1-3 alkylenedioxy, (3) nitro, (4) cyano, (5) optionally halogenated C1-6 alkyl, (6) optionally halogenated C2-6 alkenyl, (7) optionally halogenated C2-6 alkynyl, (8) optionally halogenated C3-8 cycloalkyl, (9) optionally halogenated C6-14 aryl, (10) optionally halogenated C1-6 alkoxy, (11) optionally halogenated C1-6 alkylthio or mercapto, (12) hydroxy, (13) amino, (14) mono-C1-6 alkylamino, (15) mono-C6-14 arylamino, (16) di-C1-6 alkylamino, (17) di-C6-14 arylamino, (18) acyl which is selected from formyl, carboxy, carbamoyl, C1-6 alkyl-carbonyl, C3-8 cycloalkyl-carbonyl, C1-6 alkoxy-carbonyl, C6-14 aryl-carbonyl, C7-16 aralkyl-carbonyl, C6-14 aryloxy-carbonyl, C7-16 aralkyloxy-carbonyl, 5- or 6-membered heterocyclic carbonyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, mono-C1-6 alkyl-carbamoyl, di-C1-6 alkyl-carbamoyl, thiocarbamoyl, C6-14 aryl-carbamoyl, 5- or 6-membered heterocyclic carbamoyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, C1-6 alkylsulfonyl, C6-14 arylsulfonyl, C1-6 alkylsulfinyl and C6-14 arylsulfinyl, (19) acylamino selected from formyl amino, C1-6 alkyl-carbonylamino, C6-14 aryl-carbonylamino, C1-6 alkoxy-carbonylamino, C1-6 alkylsulfonyl amino, and C6-14 arylsulfonyl amino, (20) acyloxy selected from C1-6 alkyl-carbonyloxy, C6-14 aryl-carbonyloxy, C1-6 alkoxy-carbonyloxy, mono-C1-6 alkyl-carbamoyloxy, di-C1-6 alkyl-carbamoyloxy, C6-14 aryl-carbamoyloxy and nicotinoyloxy, (21) 4-8 membered saturated cyclic amino optionally including 1-3 substituents which are selected from C1-6 alkyl, C6-14 aryl and a 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (22) 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (23) sulfo and (24) C6-14 aryloxy;    R3 represents (1) C6-14 aryl, (2) optionally halogenated C3-8 cycloalkyl or (3) 5-10 membered heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, which may respectively include 1-5 substituents selected from (1) halogen, (2) C1-3 alkylenedioxy, (3) nitro, (4) cyano, (5) optionally halogenated C1-6 alkyl, (6) optionally halogenated C2-6 alkenyl, (7) optionally halogenated C2-6 alkynyl, (8) optionally halogenated C3-8 cycloalkyl, (9) optionally halogenated C6-14 aryl, (10) optionally halogenated C1-6 alkoxy, (11) optionally halogenated C1-6 alkylthio or mercapto, (12) hydroxy, (13) amino, (14) mono-C1-6 alkylamino, (15) mono-C6-14 arylamino, (16) di-C1-6 alkylamino, (17) di-C6-14 arylamino, (18) acyl which is selected from formyl, carboxy, carbamoyl, C1-6 alkyl-carbonyl, C3-8 cycloalkyl-carbonyl, C1-6 alkoxy-carbonyl, C6-14 aryl-carbonyl, C7-16 aralkyl-carbonyl, C6-14 aryloxy-carbonyl, C7-16 aralkyloxy-carbonyl, 5- or 6-membered heterocyclic carbonyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, mono-C1-6 alkyl-carbamoyl, di-C1-6 alkyl-carbamoyl, C6-14 aryl-carbamoyl, thiocarbamoyl, 5 or 6 membered heterocyclic carbamoyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, C1-6 alkylsulfonyl, C6-14 arylsulfonyl, C1-6 alkylsulfinyl and C6-14 arylsulfinyl, (19) acylamino selected from formyl amino, C1-6 alkyl-carbonylamino, C6-14 aryl-carbonylamino, C1-6 alkoxy-carbonylamino, C1-6 alkylsulfonyl amino and C6-14 arylsulfonyl amino, (20) acyloxy selected from C1-6 alkyl-carbonyloxy, C6-14 aryl-carbonyloxy, C1-6 alkoxy-carbonyloxy, mono-C1-6 alkyl-carbamoyloxy, di-C1-6 alkyl-carbamoyloxy, C6-14 aryl-carbamoyloxy and nicotinoyloxy, (21) 4-8 membered saturated cyclic amino which may contain 1-3 substituents selected from C1-6 alkyl, C6-14 aryl, and 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (22) 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (23) sulfo and (24) C6-14 aryloxy    X is a bond,                          (wherein, R′ and R″ represent a hydrogen atom, C1-6 alkyl group, C3-8 cycloalkyl group or C6-14 aryl group, and n is an integer of 1-3, and when n is 2 or 3, R′ and R″ may be different in each repeating unit), —CO—, —O—, —S—, —SO—, —SO 2 — or NR 5 — (wherein, R 5  represents a hydrogen atom or C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C3-8 cycloalkyl group, C6-14 aryl group, each of which may respectively contain 1-5 substituents selected from (1) halogen, (2) C1-3 alkylenedioxy, (3) nitro, (4) cyano, (5) optionally halogenated C1-6 alkyl, (6) optionally halogenated C2-6 alkenyl, (7) optionally halogenated C2-6 alkynyl, (8) optionally halogenated C3-8 cycloalkyl, (9) optionally halogenated C6-14 aryl, (10) optionally halogenated C1-6 alkoxy, (11) optionally halogenated C1-6 alkylthio or mercapto, (12) hydroxy, (13) amino, (14) mono-C1-6 alkylamino, (15) mono-C6-14 arylamino, (16) di-C1-6 alkylamino, (17) di-C6-14 arylamino, (18) acyl selected from formyl, carboxy, carbamoyl, C1-6 alkyl-carbonyl, C3-8 cycloalkyl-carbonyl, C1-6 alkoxy-carbonyl, C6-14 aryl-carbonyl, C7-16 aralkyl-carbonyl, C6-14 aryloxy-carbonyl, C7-16 aralkyloxy-carbonyl, 5- or 6-membered heterocyclic carbonyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, mono-C1-6 alkyl-carbamoyl, di-C1-6 alkyl-carbamoyl, C6-14 aryl-carbamoyl, thiocarbamoyl, 5- or 6-membered heterocyclic carbamoyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, C1-6 alkylsulfonyl, C6-14 arylsulfonyl, C1-6 alkylsulfinyl and C6-14 arylsulfinyl, (19) acylamino selected from formyl amino, C1-6 alkyl-carboxamide, C6-14 aryl-carboxamide, C1-6 alkoxy-carboxamide, C1-6 alkylsulfonyl amino and C6-14 arylsulfonyl amino, (20) acyloxy which is selected from C1-6 alkyl-carbonyloxy, C6-14 aryl-carbonyloxy, C1-6 alkoxy-carbonyloxy, mono-C1-6 alkyl-carbamoyloxy, di-C1-6 alkyl-carbamoyloxy, C6-14 aryl-carbamoyloxy and nicotinoyloxy, (21) 4-8 membered saturated cyclic amino optionally containing 1-3 substituents selected from C1-6 alkyl, C6-14 aryl and 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (22) 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (23) sulfo, and (24) C6-14 aryloxy), and a divalent group combining 1-3 of these may be formed;    R4 represents a hydrogen atom or C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group or C3-8 cycloalkyl group, C6-14 aryl group, hydroxy group, mercapto group which may have oxo, or amino group, which may respectively include 1-5 substituents selected from (1) halogen, (2) C1-3 alkylenedioxy, (3) nitro, (4) cyano, (5) optionally halogenated C1-6 alkyl, (6) optionally halogenated C2-6 alkenyl, (7) optionally halogenated C2-6 alkynyl, (8) optionally halogenated C3-8 cycloalkyl, (9) optionally halogenated C6-14 aryl, (10) optionally halogenated C1-6 alkoxy, (II) optionally halogenated C1-6 alkylthio or mercapto, (12) hydroxy, (13) amino, (14) mono-C1-6 alkylamino, (15) mono-C6-14 arylamino, (16) di-C1-6 alkylamino, (17) di-C6-14 arylamino, (18) the acyl which is selected from formyl, carboxy, carbamoyl, C1-6 alkyl-carbonyl, C3-8 cycloalkyl-carbonyl, C1-6 alkoxy-carbonyl, C6-14 aryl-carbonyl, C7-16 aralkyl-carbonyl, C6-14 aryloxy-carbonyl, C7-16 aralkyloxy-carbonyl, 5- or 6-membered heterocyclic carbonyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, mono-C1-6 alkyl-carbamoyl, di-C1-6 alkyl-carbamoyl, C6-14 aryl-carbamoyl, thiocarbamoyl, 5- or 6-membered heterocyclic carbamoyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, C1-6 alkylsulfonyl, C6-14 arylsulfonyl, C1-6 alkylsulfinyl and C6-14 arylsulfinyl, (19) acylamino selected from formyl amino, C1-6 alkyl-carbonylamino, C6-14 aryl-carbonylamino, C1-6 alkoxy-carbonylamino, C1-6 alkylsulfonyl amino, and C6-14 arylsulfonyl amino, (20) acyloxy selected from C1-6 alkyl-carbonyloxy, C6-14 aryl-carbonyloxy, C1-6 alkoxy-carbonyloxy, mono-C1-6 alkyl-carbamoyloxy, di-C1-6 alkyl-carbamoyloxy, C6-14 aryl-carbamoyloxy and nicotinoyloxy, (21) 4-8 membered saturated cyclic amino which may contain 1-3 substituents selected from C1-6 alkyl, C6-14 aryl and 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (22) 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (23) sulfo and (24) C6-14 aryloxy, or R2 and R4 may link together to form a double bond, and    ring B via —Y— is (i) a hydrogen atom, (ii) halogen, (iii) oxo, (iv) [1] halogen or [2] C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C3-8 cycloalkyl group, C6-14 aryl group or 4-8 membered nitrogen-containing ring which may contain 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, and which may respectively include 1-5 substituents selected from (1) halogen, (2) C1-3 alkylenedioxy, (3) nitro, (4) cyano, (5) optionally halogenated C1-6 alkyl, (6) optionally halogenated C2-6 alkenyl, (7) optionally halogenated C2-6 alkynyl, (8) optionally halogenated C3-8 cycloalkyl, (9) optionally halogenated C6-14 aryl, (10) optionally halogenated C1-6 alkoxy, (11) optionally halogenated C1-6 alkylthio or mercapto, (12) hydroxy, (13) amino, (14) mono-C1-6 alkylamino, (15) mono-C6-14 arylamino, (16) di-C1-6 alkylamino, (17) di-C6-14 arylamino, (18) acyl selected from formyl, carboxy, carbamoyl, C1-6 alkyl-carbonyl, C3-8 cycloalkyl-carbonyl, C1-6 alkoxy-carbonyl, C6-14 aryl-carbonyl, C7-16 aralkyl-carbonyl, C6-14 aryloxy-carbonyl, C7-16 aralkyloxy-carbonyl, 5- or 6-membered heterocyclic carbonyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, mono-C1-6 alkyl-carbamoyl, di-C1-6 alkyl-carbamoyl, C6-14 aryl-carbamoyl, thiocarbamoyl, 5 or 6 membered heterocyclic carbamoyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, C1-6 alkylsulfonyl, C6-14 arylsulfonyl, C1-6 alkylsulfinyl and C6-14 arylsulfinyl, (19) acylamino selected from formyl amino, C1-6 alkyl-carboxamide, C6-14 aryl-carboxamide, C1-6 alkoxy-carboxamide, C1-6 alkylsulfonyl amino and C6-14 arylsulfonyl amino, (20) acyloxy selected from C1-6 alkyl-carbonyloxy, C6-14 aryl-carbonyloxy, C1-6 alkoxy-carbonyloxy, mono-C1-6 alkyl-carbamoyloxy, di-C1-6 alkyl-carbamoyloxy, C6-14 aryl-carbamoyloxy and nicotinoyloxy, (21) 4-8 membered saturated cyclic amino which may contain 1-3 substituents selected from C1-6 alkyl, C6-14 aryl, and 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (22) 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (23) sulfo and (24) C6-14 aryloxy; wherein Y is a bond, —CO—, —O—, —S—, —SO—, —SO 2 — or NR 6 — (in the formula, R 6  represents a hydrogen atom or C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C3-8 cycloalkyl group, C6-14 aryl group, which may respectively contain 1-5 substituents selected from (1) halogen, (2) C1-3 alkylenedioxy, (3) nitro, (4) cyano, (5) optionally halogenated C1-6 alkyl, (6) optionally halogenated C2-6 alkenyl, (7) optionally halogenated C2-6 alkynyl, (8) optionally halogenated C3-8 cycloalkyl, (9) optionally halogenated C6-14 aryl, (10) optionally halogenated C1-6 alkoxy, (11) optionally halogenated C1-6 alkylthio or mercapto, (12) hydroxy, (13) amino, (14) mono-C1-6 alkylamino, (15) mono-C6-14 arylamino, (16) di-C1-6 alkylamino, (17) di-C6-14 arylamino, (18) acyl selected from formyl, carboxy, carbamoyl, C1-6 alkyl-carbonyl, C3-8 cycloalkyl-carbonyl, C1-6 alkoxy-carbonyl, C6-14 aryl-carbonyl, C7-16 aralkyl-carbonyl, C6-14 aryloxy-carbonyl, C7-16 aralkyloxy-carbonyl, 5- or 6-membered heterocyclic carbonyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, mono-C1-6 alkyl-carbamoyl, di-C1-6 alkyl-carbamoyl, C6-14 aryl-carbamoyl, thiocarbamoyl, 5- or 6-membered heterocyclic carbamoyl which includes 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, C1-6 alkylsulfonyl, C6-14 arylsulfonyl, C1-6 alkylsulfinyl and C6-14 arylsulfinyl, (19) acylamino selected from formyl amino, C1-6 alkyl-carboxamide, C6-14 aryl-carboxamide, C1-6 alkoxy-carboxamide, C1-6 alkylsulfonyl amino and C6-14 arylsulfonyl amino, (20) acyloxy selected from C1-6 alkyl-carbonyloxy, C6-14 aryl-carbonyloxy, C1-6 alkoxy-carbonyloxy, mono-C1-6 alkyl-carbamoyloxy, di-C1-6 alkyl-carbamoyloxy, C6-14 aryl-carbamoyloxy and nicotinoyloxy, (21) 4-8 membered saturated cyclic amino which may contain 1-3 substituents selected from C1-6 alkyl, C6-14 aryl, and 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (22) 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (23) sulfo and (24) C6-14 aryloxy), and;    ring C represents a benzene ring which may further include, in addition to ring B, 1-3 substituents selected from (1) halogen, (2) C1-3 alkylenedioxy, (3) nitro, (4) cyano, (5) optionally halogenated C1-8 alkyl, (6) optionally halogenated C2-8 alkenyl, (7) optionally halogenated C2-8 alkynyl, (8) optionally halogenated C3-8 cycloalkyl, (9) optionally halogenated C6-14 aryl, (10) optionally halogenated C1-6 alkoxy, (11) hydroxy, (12) amino, (13) mono-C1-6 alkylamino, (14) mono-C6-14 arylamino, (15) di-C1-6 alkylamino, (16) di-C6-14 arylamino, (17) acyl selected from formyl, carboxy, carbamoyl, C1-6 alkyl-carbonyl, C3-8 cycloalkyl-carbonyl, C1-6 alkoxy-carbonyl, C6-14 aryl-carbonyl, C7-16 aralkyl-carbonyl, C6-14 aryloxy-carbonyl, C7-16 aralkyloxy-carbonyl, 5- or 6-membered heterocyclic carbonyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, mono-C1-6 alkyl-carbamoyl, di-C1-6 alkyl-carbamoyl, C6-14 aryl-carbamoyl, thiocarbamoyl, 5- or 6-membered heterocyclic carbamoyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, C1-6 alkylsulfonyl, C6-14 arylsulfonyl, C1-6 alkylsulfinyl and C6-14 arylsulfinyl, (18) acylamino selected from formyl amino, C1-6 alkyl-carboxamide, C6-14 aryl-carboxamide, C1-6 alkoxy-carboxamide, C1-6 alkylsulfonyl amino and C6-14 arylsulfonyl amino, (19) 4-8 membered saturated cyclic amino optionally containing 1-3 substituents selected from C1-6 alkyl, C6-14 aryl, and 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (20) 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, and (21) sulfo.    
   
   
       3 . The compounds as defined in  claim 1 , wherein W is an oxygen atom.  
   
   
       4 . The compounds as defined in  claim 1 , wherein X is a bond.  
   
   
       5 . The compounds as defined in  claim 1 , wherein X is  
     
       
         
         
             
             
         
       
     
     (wherein, R′ and R″ represent a hydrogen atom, C1-6 alkyl group, C3-8 cycloalkyl group or C6-14 aryl group, and n is an integer of 1-3, and when n is 2 or 3, R′ and R″ may be different in each repeating unit).  
   
   
       6 . The compounds as defined in  claim 1 , wherein   is a single bond.  
   
   
       7 . The compounds as defined in  claim 1 , wherein R3 is a optionally substituted C6-14 aryl group.  
   
   
       8 . The compounds as defined in  claim 1 , wherein R3 is an optionally substituted heterocyclic group.  
   
   
       9 . The compounds as defined in  claim 1 , wherein X is a bond, and R3 is an optionally substituted phenyl group.  
   
   
       10 . The compounds as defined in  claim 1 , wherein X is a bond, R3 is a phenyl group which may respectively contain 1-5 substituents selected from (1) halogen, (2) optionally halogenated C1-6 alkyl, (3) optionally halogenated C6-14 aryl, (4) optionally halogenated C1-6 alkoxy, and (5) di-C1-6 alkylamino.  
   
   
       11 . The compounds as defined in  claim 1 , wherein X is a bond, R3 is a 5-8 membered heterocyclic group including 1-3 nitrogen atoms, as heteroatoms, on the ring structure, and which may also contain 1-5 substituents selected from (1) halogen, (2) C1-3 alkylenedioxy, (3) nitro, (4) cyano, (5) optionally halogenated C1-6 alkyl, (6) optionally halogenated C2-6 alkenyl, (7) optionally halogenated C2-6 alkynyl, (8) optionally halogenated C3-8 cycloalkyl, (9) optionally halogenated C6-14 aryl, (10) optionally halogenated C1-6 alkoxy, (11) optionally halogenated C1-6 alkylthio or mercapto, (12) hydroxy, (13) amino, (14) mono-C1-6 alkylamino, (15) mono-C6-14 arylamino, (16) di-C1-6 alkylamino, (17) di-C6-14 arylamino, (18) acyl selected from formyl, carboxy, carbamoyl, C1-6 alkyl-carbonyl, C3-8 cycloalkyl-carbonyl, C1-6 alkoxy-carbonyl, C6-14 aryl-carbonyl, C7-16 aralkyl-carbonyl, C6-14 aryloxy-carbonyl, C7-16 aralkyloxy-carbonyl, 5- or 6-membered heterocyclic carbonyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, mono-C1-6 alkyl-carbamoyl, di-C1-6 alkyl-carbamoyl, C6-14 aryl-carbamoyl, thiocarbamoyl, 5- or 6-membered heterocyclic carbamoyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, C1-6 alkylsulfonyl, C6-14 arylsulfonyl, C1-6 alkylsulfinyl and C6-14 arylsulfinyl, (19) acylamino selected from formyl amino, C1-6 alkyl-carbonylamino, C6-14 aryl-carbonylamino, C1-6 alkoxy-carbonylamino, C1-6 alkylsulfonyl amino and C6-14 arylsulfonyl amino, (20) acyloxy selected from C1-6 alkyl-carbonyloxy, C6-14 aryl-carbonyloxy, C1-6 alkoxy-carbonyloxy, mono-C1-6 alkyl-carbamoyloxy, di-C1-6 alkyl-carbamoyloxy, C6-14 aryl-carbamoyloxy and nicotinoyloxy, (21) 4-8 membered saturated cyclic amino which may contain 1-3 substituents selected from C1-6 alkyl, C6-14 aryl and 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (22) 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (23) sulfo and (24) C6-14 aryloxy.  
   
   
       12 . The compounds as defined in  claim 1 , wherein X is a bond, and R3 is piperidino, morpholino, piperazinyl, pyridyl or pyrrolidinyl group which may respectively contain 1-3 substituents selected from (1) halogen, (2) optionally halogenated C1-6 alkyl, (3) optionally halogenated C6-14 aryl and (4) acyl selected from formyl, carboxy, carbamoyl, C1-6 alkyl-carbonyl, C3-8 cycloalkyl-carbonyl, C1-6 alkoxy-carbonyl, C6-14 aryl-carbonyl, C7-16 aralkyl-carbonyl, C6-14 aryloxy-carbonyl and C7-16 aralkyloxy-carbonyl.  
   
   
       13 . The compounds as defined in  claim 1 , wherein ring B includes 1-4 groups (that may be respectively the same or different when a plurality is included) represented by the formula —Y—Ar [wherein, Y represents —(CH 2 ) m — (m represents an integer of 1 to 6), —CO—, —O—, —S—, —SO—, —SO 2 — or —NR 6 — (wherein R 6  represents a hydrogen atom or optionally substituted hydrocarbon group) or a bond, and Ar represents optionally substituted aromatic group].  
   
   
       14 . The compounds as defined in  claim 1 , wherein ring B is a piperidine ring, piperazine ring or pyrrolidine ring.  
   
   
       15 . The compounds as defined in  claim 1 , wherein ring B is substituted in the 5 position of a (dihydro) benzo thiophene ring or a (dihydro) benzofuran ring.  
   
   
       16 . The compound as defined in  claim 13 , wherein the aromatic ring represented by Ar is a optionally substituted phenyl group.  
   
   
       17 . The compound as defined in  claim 13 , wherein Y is a bond.  
   
   
       18 . The compounds as defined in  claim 1 , wherein R1 and R2 are respectively C1-6 alkyl group.  
   
   
       19 . The compounds as defined in  claim 1 , wherein R4 is a hydrogen atom.  
   
   
       20 . The compounds as defined in  claim 1 , wherein ring C further includes, in addition to ring B, 1-3 substituents selected from (1) halogen, (2) C1-3 alkylenedioxy, (3) nitro, (4) cyano, (5) optionally halogenated C1-8 alkyl, (6) optionally halogenated C2-8 alkenyl, (7) optionally halogenated C2-8 alkynyl, (8) optionally halogenated C3-8 cycloalkyl, (9) optionally halogenated C6-14 aryl, (10) optionally halogenated C1-6 alkoxy, (II) hydroxy, (12) amino, (13) mono-C1-6 alkylamino, (14) mono-C6-14 arylamino, (15) di-C1-6 alkylamino, (16) di-C6-14 arylamino, (17) acyl selected from formyl, carboxy, carbamoyl, C1-6 alkyl-carbonyl, C3-8 cycloalkyl-carbonyl, C1-6 alkoxy-carbonyl, C6-14 aryl-carbonyl, C7-16 aralkyl-carbonyl, C6-14 aryloxy-carbonyl, C7-16 aralkyloxy-carbonyl, 5- or 6-membered heterocyclic carbonyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, mono-C1-6 alkyl-carbamoyl, di-C1-6 alkyl-carbamoyl, C6-14 aryl-carbamoyl, thiocarbamoyl, 5- or 6-membered heterocyclic carbamoyl including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, C1-6 alkylsulfonyl, C6-14 arylsulfonyl, C1-6 alkylsulfinyl and C6-14 arylsulfinyl, (18) acylamino selected from formyl amino, C1-6 alkyl-carboxamide, C6-14 aryl-carboxamide, C1-6 alkoxy-carboxamide, C1-6 alkylsulfonylamino, and C6-14 arylsulfonylamino, (19) 4-8 membered saturated cyclic amino which may contain 1-3 substituents selected from C1-6 alkyl, C6-14 aryl, and 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, (20) 5-10 membered aromatic heterocyclic group including, other than carbon atoms, 1-4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms, and (21) sulfo.  
   
   
       21 . The compounds as defined in  claim 1 , wherein ring C further includes, in addition to ring B, 1-3 substituents selected from (1) halogen, (2) C1-3 alkylenedioxy, (3) nitro, (4) cyano, (5) C1-8 alkyl, (6) C2-8 alkenyl, (7) C2-8 alkynyl, (8) optionally halogenated C3-8 cycloalkyl, (9) optionally halogenated C6-14 aryl, (10) C1-6 alkoxy, (11) hydroxy, (12) amino, (13) mono-C1-6 alkylamino, (14) mono-C6-14 arylamino, (15) di-C1-6 alkylamino, (16) di-C6-14 arylamino, (17) acyl selected from formyl, carboxy, carbamoyl, C1-6 alkyl-carbonyl, C3-8 cycloalkyl-carbonyl, C1-6 alkoxy-carbonyl, C6-14 aryl-carbonyl, C7-16 aralkyl-carbonyl, C6-14 aryloxy-carbonyl, C7-16 aralkyloxy-carbonyl, mono-C1-6 alkyl-carbamoyl, di-C1-6 alkyl-carbamoyl, C6-14 aryl-carbamoyl, thiocarbamoyl, C1-6 alkylsulfonyl, C6-14 arylsulfonyl, C1-6 alkylsulfinyl and C6-14 arylsulfinyl, (18) acylamino selected from formyl amino, C1-6 alkyl-carboxamide, C6-14 aryl-carboxamide, C1-6 alkoxy-carboxamide, C1-6 alkylsulfonyl amino, and C6-14 arylsulfonyl amino and (19) sulfo.  
   
   
       22 . The compounds as defined in  claim 1 , wherein ring C further includes, in addition to ring B, 1 to 3 C1-6 alkyl groups.  
   
   
       23 . The compounds as defined in  claim 1 , wherein ring C further includes, in addition to ring B, 3 C1-6 alkyl groups.  
   
   
       24 . The compounds as defined in  claim 1 , wherein ring C includes, in addition to ring B, 3 methyl groups.  
   
   
       25 . 4-(3,4-dimethoxyphenyl)-1-(2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)piperazine, 
 (3R)-4-(4-methoxyphenyl)-1-(2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)piperidine,    1-(2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine,    N-phenyl-5-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-amine,    4-(4-methoxyphenyl)-1-(2,2,4,6,7-pentamethyl-3-piperidino-2,3-dihydro-1-benzofuran-5-yl)piperazine,    1-(3-(4-(trifluoromethyl)phenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine,    4-(3,4-dimethoxyphenyl)-1-(3-(4-methylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperidine,    1-(3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(3,4-dimethoxyphenyl)piperidine,    1-(4-methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-3-[pyrrolidin-1-yl]-2,3-dihydro-1-benzofuran-5-yl)piperazine,    1-(5-(4-(4-methoxyphenyl)1-piperazinyl)-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl)indoline,    1-(4-methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-3-pyridine-2-yl-2,3-dihydro-1-benzofuran-5-yl)piperazine,    1-(3-(6-fluoropyridin-3-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine,    1-(3,4-dimethoxyphenyl)-4-(2,2,4,6,7-pentamethyl-3-piperidino-2,3-dihydro-1-benzofuran-5-yl)piperazine,    1-(4-methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-3-(6-methyl-3-pyridinyl)-2,3-dihydro-1-benzofuran-5-yl)piperazine,    4-(4-methoxyphenyl)-1-(2,2,4,5,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-6-yl)piperazine,    1-(3-benzyl-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine, or    1-(4-methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-3-((4-phenoxy)methyl)-2,3-dihydro-1-benzofuran-5-yl)piperazine,    
   
   
       26 . Prodrugs of the compounds as defined in  claim 1 .  
   
   
       27 . A neurodegeneration inhibitor which includes a compound as defined in  claim 1 , a salt thereof, or a prodrug thereof.  
   
   
       28 . The inhibitor as defined in  claim 27 , which is a β-amyloid toxicity inhibitor.  
   
   
       29 . The inhibitor as defined in  claim 27 , which is a neurotrophic factor like agent.  
   
   
       30 . The inhibitor as defined in  claim 27 , which is an agent for preventing/treating neurodegenerative diseases.  
   
   
       31 . The inhibitor as defined in  claim 27 , which is an agent for preventing/treating Alzheimer's disease or Parkinson's disease.  
   
   
       32 . A inhibitor as defined in  claim 27 , which is a therapeutic agent for mild cognitive impairment or mild memory loss.  
   
   
       33 . A neurogenesis promotion agent or a neuroregeneration promotion agent that includes a compound as defined in  claim 1 , a salt thereof, or a prodrug thereof.  
   
   
       34 . The agent as defined in  claim 33 , which is a proliferation/differentiation promotion agent for stem cells and/or neural precursor cells.  
   
   
       35 . The agent as defined in  claim 33 , wherein the stem cells are embryonic stem cells or neural stem cells.  
   
   
       36 . The agent as defined in  claim 33 , which is a survival/differentiation promotion agent for neural stem cells and/or nerve cell grafts.  
   
   
       37 . The agent as defined in  claim 33 , which is a proliferation/differentiation promotion agent for neural stem cells and/or neural cells.  
   
   
       38 . The agent as defined in  claim 33 , which is a proliferation/differentiation promotion agent for endogenous neural stem cells.  
   
   
       39 . The agent as defined in  claim 33 , which is for preventing/treating central nervous system diseases.  
   
   
       40 . A proliferation/differentiation promotion agent for culturing neural stem cells and/or neural precursor cells for transplantation which includes a compound as defined in  claim 1  or a salt thereof.  
   
   
       41 . Use of compounds as defined in  claim 1  or salts thereof as a proliferation/differentiation promotion agent when culturing neural stem cells and/or neural precursor cells for transplantation.  
   
   
       42 . Protein kinase B (PKB) activator which includes a compound defined in  claim 1 , a salt thereof, or a prodrug thereof.  
   
   
       43 . The PKB activator as defined in  claim 42 , which is an agent for preventing/treating Parkinson's disease, Alzheimer's disease, amyotrophic lateral sclerosis (ALS) or Huntington's disease.  
   
   
       44 . The PKB activator as defined in  claim 42 , which is an agent for preventing/treating depression, anxiety, manic depression or PTSD (post-traumatic stress disorder).  
   
   
       45 . Use of the PKB activator as defined in  claim 42  for the production of an agent for preventing/treating Parkinson's disease, Alzheimer's disease, ALS or Huntington's disease.  
   
   
       46 . A process for treating or preventing Parkinson's disease, Alzheimer's disease, ALS or Huntingdon's disease in a mammal, comprising the administration of the PKB activator as defined in  claim 42  to a mammal requiring prevention/treatment of Parkinson's disease, Alzheimer's disease, ALS or Huntington's disease.  
   
   
       47 . Use of the PKB activator as defined in  claim 42  for the production of an agent for preventing/treating depression, anxiety, manic depression or PTSD.  
   
   
       48 . A process for the prevention/treatment of depression, anxiety, manic depression or PTSD in a mammal, comprising the administration of the PBK activator as defined in  claim 42  to a mammal requiring prevention/treatment of depression, anxiety, manic depression or PTSD.  
   
   
       49 . A neurodegeneration inhibitor that includes a compound represented by the formula  
     
       
         
         
             
             
         
       
     
     (wherein, ring B represents an optionally substituted 5-8 membered nitrogen-containing heterocyclic group, ring C represents a benzene ring which may further contain substituents in addition to the group represented by ring B, ring D represents an optionally substituted 5-membered ring, Z represents a carbon atom, nitrogen atom, oxygen atom or sulfur atom, and   represents a single bond or a double bond), a salt thereof, or a prodrug thereof.  
   
   
       50 . The inhibitor as defined in  claim 49 , wherein Z is an oxygen atom.  
   
   
       51 . The inhibitor as defined in  claim 49 , which is a β-amyloid toxicity inhibitor.  
   
   
       52 . The inhibitor as defined in  claim 49 , which is a neurotrophic factor like agent.  
   
   
       53 . The inhibitor as defined in  claim 49 , which is an agent for preventing/treating neurodegenerative diseases.  
   
   
       54 . The inhibitor as defined in  claim 49 , which is an agent for preventing/treating Alzheimer's disease, Parkinson's disease, ALS or Huntington's disease.  
   
   
       55 . The inhibitor as defined in  claim 49 , which is a therapeutic agent for mild cognitive impairment or mild memory loss.  
   
   
       56 . A PKB activator which includes a compound as defined in  claim 49 , a salt thereof, or prodrug thereof.  
   
   
       57 . A neurogenesis promotion agent or a neuroregeneration promotion agent which includes a compound as defined in  claim 49 , a salt thereof, or prodrug thereof.  
   
   
       58 . The agent as defined in  claim 57 , which is a proliferation/differentiation promotion agent for stem cells and/or neural precursor cells.  
   
   
       59 . The agent as defined in  claim 57 , wherein Z is an oxygen atom.  
   
   
       60 . The agent as defined in  claim 57 , wherein the stem cells are embryonic stem cells or neural stem cells.  
   
   
       61 . The agent as defined in  claim 57 , which is a survive/differentiation promotion agent for neural stem cells and/or neural cell grafts.  
   
   
       62 . The agent as defined in  claim 57 , which is a proliferation/differentiation promotion agent for neural stem cells and/or neural cells for transplantation.  
   
   
       63 . The agent as defined in  claim 57 , which is a proliferation/differentiation promotion agent for endogenous neural stem cells.  
   
   
       64 . The agent as defined in  claim 57 , which is for preventing/treating central nervous system diseases.  
   
   
       65 . A proliferation/differentiation promotion agent for stem cells and/or neural precursor cells for neural stem cell culture that include a compound as defined in  claim 49 , or a salt thereof.  
   
   
       66 . The agent as defined in  claim 65 , wherein Z is an oxygen atom.  
   
   
       67 . Use of compounds as defined in  claim 49  or salts thereof as a proliferation/differentiation promotion agent for stem cells and/or neural precursor cells for neural stem cell culture.  
   
   
       68 . The use as defined in  claim 67 , wherein Z is an oxygen atom.  
   
   
       69 . A process for producing compounds as defined in  claim 1  or salts thereof, comprising the step of reacting compounds represented by the formula:  
     
       
         
         
             
             
         
       
     
     (wherein each symbol has the same meaning as in  claim 1)  or salts thereof with compounds represented by the formula:  
       L 1 -E-L 2    
     (wherein, L 1  and L 2  represent leaving groups, and E represents a partial sequence of the ring structure of ring B other than the nitrogen atom) or salts thereof.  
   
   
       70 . The production process as defined in  claim 69 , in which the reaction occurs in the presence of base.