7-membered ring compound and method of production and pharmaceutical application thereof

Abstract

A 7-membered heterocyclic compound having the formula (I), or its salt, or a solvate thereof with a chymase inhibitory action and useful for the prevention or treatment of various diseases, in which chymase is involved: a method for producing the same, and a pharmaceutical composition useful for the prevention or treatment of diseases, in which chymase is involved, including the compound of having the formula (I), or its pharmaceutically acceptable salt, or a solvate thereof are provided.

1 - 24 . (canceled) 
     
     
         25 . A compound, or its salt, or a solvate thereof, having the formula (VIa): 
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , and R 3  are the same as defined in claim  1 , P is the same as defined in claim  23 ,
 X′ indicates methylene, or X′ forms —CH=together with R 1 ; 
 P′ indicates a protective group selected from the group consisting of (1) allyl, (2) allyloxycarbonyl, (3) 9-fluorenylmethylcarbonyl, (4) linear or branched C 1  to C 6  alkyloxycarbonyl which may optionally be substituted with 1 to 3 halogen atoms, (5) linear or branched C 1  to C 6  alkylcarbonyl which may optionally be substituted with 1 to 3 halogen atoms, (6) C 7  to C 16  aralkyl which may optionally be substituted with 1 to 3 of (i) a halogen atom, (ii) C 1  to C 6  alkyl, (iii) C 1  to C 6  alkoxy, or (iv) nitro, (7) C 5  to C 16  arylcarbonyl which may optionally be substituted with 1 to 3 of (i) a halogen atom, (ii) C 1  to C 6  alkyl, (iii) C 1  to C 6  alkoxy, or (iv) nitro, (8) C 7  to C 16  aralkyloxycarbonyl which may optionally be substituted with 1 to 3 of (i) a halogen atom, (ii) C 1  to C 6  alkyl, (iii) C 1  to C 6  alkoxy, or (iv) nitro, and (9) C 5  to C 16  arylsulfonyl which may optionally be substituted with 1 to 3 of (i) a halogen atom, (ii) C 1  to C 6  alkyl, (iii) C 1  to C 6  alkoxy, or (iv) nitro, or a hydrogen atom; 
 R 20  is (1) a halogen atom, (2) nitro, (3) cyano, (4) C 1  to C 6  alkyl which may optionally be substituted with 1 to 3 halogen atoms, (5) hydroxyl, or (6) C 1  to C 6  alkoxy which may be substituted with 1 to 3 groups selected from a halogen atom, C 1  to C 6  alkoxy, carboxyl, and C 1  to C 6  alkoxycarbonyl; and 
 R 21 , R 22 , R 23 , and R 24  are, independently, (1) a halogen atom, (2) nitro, (3) cyano, (4) C 1  to C 6  alkyl which may be substituted with 1 to 3 halogen atoms, (5) hydroxyl, or (6) C 1  to C 6  alkoxy which may optionally be substituted with 1 to 3 groups selected from a halogen atom, C 1  to C 6  alkoxy, carboxyl, and C 1  to C 6  alkoxycarbonyl, or a hydrogen atom, except for the following compounds: 
 
       (1) Compounds, wherein R 20  and R 24  are chlorine atoms and R 21 , R 22 , and R 23  are hydrogen atoms, 
       (2) Compounds, wherein R 20 , R 22 , and R 24  are methyl and R 21  and R 23  are hydrogen atoms, and 
       (3) Compounds, wherein R 20  is a chlorine atom or bromine atom and R 21 , R 22 , R 23 , and R 24  are hydrogen atoms. 
     
     
         26 . A compound, or a salt thereof, having the formula 
       
         
           
           
               
               
           
         
       
       wherein
 Ar indicates (1) a C 6  to C 14  aromatic hydrocarbon group, (2) a 5- to 8-membered aromatic heterocyclic group including 1 to 4 hetero atoms selected from a nitrogen atom, sulfur atom and oxygen atom, other than a carbon atom, or (3) a bicyclic or tricyclic aromatic group formed by condensation of the above aromatic heterocyclic group and a C 6  to C 14  aromatic hydrocarbon ring, 
 wherein the groups (1) to (3) of the above Ar may optionally be substituted with any 1 to 5 groups selected from the group consisting of (i) a halogen atom, (ii) nitro, (iii) cyano, (iv) C 1  to C 6  alkyl which may optionally be substituted with 1 to 3 halogen atoms, (v) C 2  to C 6  alkenyl which may optionally be substituted with 1 to 3 halogen atoms, (vi) C 2  to C 6  alkynyl which may optionally be substituted with 1 to 3 halogen atoms, (vii) C 3  to C 6  cycloalkyl, (viii) hydroxyl, (ix) C 1  to C 6  alkoxy which may optionally be substituted with 1 to 3 groups selected from a halogen atom, mono- or di-C 1  to C 6  alkylamino, C 1  to C 6  alkoxy, mono- or di-C 1  to C 6  alkylcarbamoyl, mono- or di-C 7  to C 16  aralkylcarbamoyl, mono- or di-C 1  to C 10  heteroaryl-C 1  to C 6  alkylcarbamoyl, carboxyl, and C 1  to C 6  alkoxycarbonyl, (x) C 1  to C 5  alkylenedioxy, (xi) C 1  to C 6  alkylthio which may optionally be substituted with 1 to 3 groups selected from a halogen atom, mono- or di-C 1  to C 6  alkylamino, C 1  to C 6  alkoxy, mono- or di-C 1  to C 6  alkylcarbamoyl, mono- or di-C 7  to C 16  aralkylcarbamoyl, mono- or di-C 1  to C 10  heteroaryl-C 1  to C 6  alkylcarbamoyl, carboxyl and C 1  to C 6  alkoxy-carbonyl, (xii) amino, (xiii) mono-C 1  to C 6  alkylamino, (xiv) di-C 1  to C 6  alkylamino, (xv) 5- to 6-membered cyclic amino, (xvi) C 1  to C 6  alkylcarbonyl, (xvii) carboxyl, (xviii) C 1  to C 6  alkoxycarbonyl, (xix) carbamoyl, (xx) thiocarbamoyl, (xxi) mono-C 1  to C 6  alkylcarbamoyl, (xxii) di-C 1  to C 6  alkylcarbamoyl, (xxiii) 5- to 6-membered cyclic aminocarbonyl, (xxiv) sulfo, (xxv) C 1  to C 6  alkylsulfonyl, (xxvi) C 1  to C 6  alkoxycarbonylamino, (xxvii) C 1  to C 6  alkylcarbonylamino, (xxviii) mono- or di-C 1  to C 6  alkylaminocarbonylamino, (xxix) aminosulfonyl, and (xxx) mono- or di-C 1  to C 6  alkylaminosulfonyl; 
 X indicates (1) a bond, (2) linear or branched C 1  to C 6  alkylene, (3) an oxygen atom, (4) NR 13 , wherein R 13  indicates a hydrogen atom or a C 1  to C 6  alkyl group, or (5) —S(O) m — wherein m indicates an integer of 0 to 2; 
 R 1  indicates (1) a hydrogen atom, (2) a halogen atom, or (3) C 1  to C 6  alkyl, or R 1  forms —CH═ together with X; 
 R 2  and R 3  are independently (1) a hydrogen atom, (2) a halogen atom, or (3) C 1  to C 6  alkyl; 
 R 5  and R 6  are independently (1) a hydrogen atom or (2) C 1  to C 6  alkyl which may optionally be substituted with a group selected from the group consisting of (i) carboxyl, (ii) C 1  to C 6  alkoxy, (iii) C 1  to C 6  alkoxycarbonyl, (iv) C 6  to C 12  aryloxycarbonyl, (v) C 1  to C 10  heteroaryloxycarbonyl, and (vi) amino; 
 R 2  and R 3  and also R 5  and R 6  may independently form a 3- to 8-membered ring; and 
 P indicates a protective group selected from the group consisting of (1) allyl, (2) allyloxycarbonyl, (3) 9-fluorenylmethylcarbonyl, (4) C 1  to C 6  alkyloxycarbonyl which may optionally be substituted with 1 to 3 halogen atoms, (5) C 1  to C 6  alkylcarbonyl which may optionally be substituted with 1 to 3 halogen atoms, (6) C 7  to C 16  aralkyl which may optionally be substituted with 1 to 3 groups selected from (i) a halogen atom, (ii) C 1  to C 6  alkyl, (iii) C 1  to C 6  alkoxy, and (iv) nitro, (7) C 5  to C 16  arylcarbonyl which may optionally be substituted with 1 to 3 groups selected from (i) a halogen atom, (ii) C 1  to C 6  alkyl, (iii) C 1  to C 6  alkoxy, and (iv) nitro, (8) C 7  to C 16  aralkyloxycarbonyl which may optionally be substituted with 1 to 3 groups selected from (i) a halogen atom, (ii) C 1  to C 6  alkyl, (iii) C 1  to C 6  alkoxy, and (iv) nitro, or (9) C 5  to C 16  arylsulfonyl which may optionally be substituted with 1 to 3 groups selected from (i) a halogen atom, (ii) C 1  to C 6  alkyl, (iii) C 1  to C 6  alkoxyl, and (iv) nitro, or R 4 , wherein R 4  indicates a (1) a hydrogen atom, (2) C 1  to C 6  alkylcarbamoyl, or (3) C 1  to C 6  alkyl which may optionally be substituted with 1 to 3 groups selected from the group consisting of (i) carbamoyl, (ii) mono- or di-C 1  to C 6  alkylcarbamoyl, (iii) mono- or di-C 6  to C 12  arylcarbamoyl, (iv) mono- or di-C 1  to C 10  heteroarylcarbamoyl, (v) N—C 1  to C 6  alkyl-N—C 6  to C 12  arylcarbamoyl, (vi) N—C 1  to C 6  alkyl-N—C 1  to C 10  heteroarylcarbamoyl, (vii) mono- or di-C 7  to C 16  aralkylcarbamoyl, (viii) mono- or di-C 1  to C 10  heteroaryl-C 1  to C 6  alkylcarbamoyl, (ix) carboxyl, and (x) C 1  to C 6  alkoxycarbonyl. 
 
     
     
         27 . A method of producing a compound or a solvate thereof having the formula of 
       
         
           
           
               
               
           
         
       
       wherein
 Ar indicates (1) a C 6  to C 14  aromatic hydrocarbon group, (2) a 5- to 8-membered aromatic heterocyclic group including 1 to 4 hetero atoms selected from a nitrogen atom, sulfur atom and oxygen atom, other than a carbon atom, or (3) a bicyclic or tricyclic aromatic group formed by condensation of the above aromatic heterocyclic group and a C 6  to C 14  aromatic hydrocarbon ring, 
 wherein the groups (1) to (3) of the above Ar may optionally be substituted with any 1 to 5 groups selected from the group consisting of (i) a halogen atom, (ii) nitro, (iii) cyano, (iv) C 1  to C 6  alkyl which may optionally be substituted with 1 to 3 halogen atoms, (v) C 2  to C 6  alkenyl which may optionally be substituted with 1 to 3 halogen atoms, (vi) C 2  to C 6  alkynyl which may optionally be substituted with 1 to 3 halogen atoms, (vii) C 3  to C 6  cycloalkyl, (viii) hydroxyl, (ix) C 1  to C 6  alkoxy which may optionally be substituted with 1 to 3 groups selected from a halogen atom, mono- or di-C 1  to C 6  alkylamino, C 1  to C 6  alkoxy, mono- or di-C 1  to C 6  alkylcarbamoyl, mono- or di-C 7  to C 16  aralkylcarbamoyl, mono- or di-C 1  to C 10  heteroaryl-C 1  to C 6  alkylcarbamoyl, carboxyl, and C 1  to C 6  alkoxycarbonyl, (x) C 1  to C s  alkylenedioxy, (xi) C 1  to C 6  alkylthio which may optionally be substituted with 1 to 3 groups selected from a halogen atom, mono- or di-C 1  to C 6  alkylamino, C 1  to C 6  alkoxy, mono- or di-C 1  to C 6  alkylcarbamoyl, mono- or di-C 7  to C 16  aralkylcarbamoyl, mono- or di-C 1  to C 10  heteroaryl-C 1  to C 6  alkylcarbamoyl, carboxyl and C 1  to C 6  alkoxy-carbonyl, (xii) amino, (xiii) mono-C 1  to C 6  alkylamino, (xiv) di-C 1  to C 6  alkylamino, (xv) 5- to 6-membered cyclic amino, (xvi) C 1  to C 6  alkylcarbonyl, (xvii) carboxyl, (xviii) C 1  to C 6  alkoxycarbonyl, (xix) carbamoyl, (xx) thiocarbamoyl, (xxi) mono-C 1  to C 6  alkylcarbamoyl, (xxii) di-C 1  to C 6  alkylcarbamoyl, (xxiii) 5- to 6-membered cyclic aminocarbonyl, (xxiv) sulfo, (xxv) C 1  to C 6  alkylsulfonyl, (xxvi) C 1  to C 6  alkoxycarbonylamino, (xxvii) C 1  to C 6  alkylcarbonylamino, (xxviii) mono- or di-C 1  to C 6  alkylaminocarbonylamino, (xxix) aminosulfonyl, and (xxx) mono- or di-C 1  to C 6  alkylaminosulfonyl; 
 X indicates (1) a bond, (2) linear or branched C 1  to C 6  alkylene, (3) an oxygen atom, (4) NR 13 , wherein R 13  indicates a hydrogen atom or a C 1  to C 6  alkyl group, or (5) —S(O) m — wherein m indicates an integer of 0 to 2; 
 R 1  indicates (1) a hydrogen atom, (2) a halogen atom, or (3) C 1  to C 6  alkyl, or R 1  forms —CH═ together with X; 
 R 2  and R 3  are independently (1) a hydrogen atom, (2) a halogen atom, or (3) C 1  to C 6  alkyl; 
 R 5  and R 6  are independently (1) a hydrogen atom or (2) C 1  to C 6  alkyl which may optionally be substituted with a group selected from the group consisting of (i) carboxyl, (ii) to C 6  alkoxy, (iii) C 1  to C 6  alkoxycarbonyl, (iv) C 6  to C 12  aryloxycarbonyl, (v) C 1  to C 10  heteroaryloxycarbonyl, and (vi) amino; 
 R 2  and R 3  and also R 5  and R 6  may independently form a 3- to 8-membered ring; 
 P indicates a protective group selected from the group consisting of (1) allyl, (2) allyloxycarbonyl, (3) 9-fluorenylmethylcarbonyl, (4) C 1  to C 6  alkyloxycarbonyl which may optionally be substituted with 1 to 3 halogen atoms, (5) C 1  to C 6  alkylcarbonyl which may optionally be substituted with 1 to 3 halogen atoms, (6) C 7  to C 16  aralkyl which may optionally be substituted with 1 to 3 groups selected from (i) a halogen atom, (ii) C 1  to C 6  alkyl, (iii) C 1  to C 6  alkoxy, and (iv) nitro, (7) C 5  to C 16  arylcarbonyl which may optionally be substituted with 1 to 3 groups selected from (i) a halogen atom, (ii) C 1  to C 6  alkyl, (iii) C 1  to C 6  alkoxy, and (iv) nitro, (8) C 7  to C 16  aralkyloxycarbonyl which may optionally be substituted with 1 to 3 groups selected from (i) a halogen atom, (ii) C 1  to C 6  alkyl, (iii) C 1  to C 6  alkoxy, and (iv) nitro, or (9) C 5  to C 16  arylsulfonyl which may optionally be substituted with 1 to 3 groups selected from (i) a halogen atom, (ii) C 1  to C 6  alkyl, (iii) C 1  to C 6  alkoxyl, and (iv) nitro, or R 4 , 
 wherein R 4  indicates a (1) a hydrogen atom, (2) C 1  to C 6  alkylcarbamoyl, or (3) C 1  to C 6  alkyl which may optionally be substituted with 1 to 3 groups selected from the group consisting of (i) carbamoyl, (ii) mono- or di-C 1  to C 6  alkylcarbamoyl, (iii) mono- or di-C 6  to C 12  arylcarbamoyl, (iv) mono- or di-C 1  to C 10  heteroarylcarbamoyl, (v) N—C 1  to C 6  alkyl-N—C 6  to C 12  arylcarbamoyl, (vi) N—C 1  to C 6  alkyl-N—C 1  to C 10  heteroarylcarbamoyl, (vii) mono- or di-C 7  to C 16  aralkylcarbamoyl, (viii) mono- or di-C 1  to C 10  heteroaryl-C 1  to C 6  alkylcarbamoyl, (ix) carboxyl, and (x) C 1  to C 6  alkoxycarbonyl; 
 W indicates (1) a hydrogen atom, (2) a C 6  to C 14  aromatic hydrocarbon group, (3) a 5- to 8-membered aromatic heterocyclic group including 1 to 4 hetero atoms selected from a nitrogen atom, a sulfur atom, and an oxygen atom, other than a carbon atom, (4) a bicyclic or tricyclic aromatic group formed by condensation of the above aromatic heterocyclic group and a C 6  to C 14  aromatic hydrocarbon ring, and (5) C 1  to C 6  alkyl, or (6) a 5- to 7-membered heterocycloalkyl group which may optionally be substituted with 1 to 3 groups selected from oxo and phenyl, 
 wherein each of the groups (2) to (4) of the above W may optionally be substituted with 1 to 5 groups selected from the group consisting of (i) a halogen atom, (ii) nitro, (iii) cyano, (iv) C 1  to C 6  alkyl which may optionally be substituted with a halogen atom, amino, C 1  to C 6  alkoxycarbonyl, C 1  to C 6  alkoxycarbonylamino, and carboxyl, (v) C 2  to C 6  alkenyl which may optionally be substituted with 1 to 3 halogen atoms, (vi) C 2  to C 6  alkynyl which may optionally be substituted with 1 to 3 halogen atoms, (vii) C 3  to C 6  cycloalkyl, (viii) hydroxyl, (ix) C 1  to C 6  alkoxy which may optionally be substituted with 1 to 3 groups selected from a halogen atom, hydroxyl, C 1  to C 6  alkoxy, amino, and mono- or di-C 1  to C 6  alkylamino, (x) C 1  to C 5  alkylenedioxy, (xi) C 1  to C 6  alkylthio which may optionally be substituted with 1 to 3 groups selected from a halogen atom, hydroxyl, C 1  to C 6  alkoxy, amino, and mono- or di-C 1  to C 6  alkylamino, (xii) amino, (xiii) mono-C 1  to C 6  alkylamino, (xiv) di-C 1  to C 6  alkylamino, (xv) 5- to 6-membered cyclic amino, (xvi) C 1  to C 6  alkylcarbonyl, (xvii) carboxyl, (xviii) C 1  to C 6  alkoxycarbonyl which may optionally be substituted with a halogen atom, (xix) C 7  to C 16  aralkyloxycarbonyl which may optionally be substituted with a halogen atom, (xx) carbamoyl, (xxi) mono-C 1  to C 6  alkylcarbamoyl which may optionally be substituted with 1 to 3 groups selected from a halogen atom, hydroxyl, carboxyl, C 1  to C 6  alkoxy, amino, and mono- or di-C 1  to C 6  alkylamino, (xxii) di-C 1  to C 6  alkylcarbamoyl which may optionally be substituted with hydroxyl, (xxiii) 5- to 6-membered cyclic aminocarbonyl which may optionally be substituted with C 1  to C 6  alkoxycarbonyl, (xxiv) C 6  to C 10  arylcarbamoyl, (xxv) C 1  to C 10  heteroarylcarbamoyl, (xxvi) C 7  to C 16  aralkylcarbamoyl, (xxvii) C 1  to C 10  heteroaryl-C 1  to C 6  alkylcarbamoyl, (xxviii) N—C 1  to C 6  alkyl-N—C 6  to C 12  arylcarbamoyl, (xxix) C 3  to C 6  cycloalkylcarbamoyl, (xxx) sulfo, (xxxi) C 1  to C 6  alkylsulfonyl, (xxxii) C 1  to C 6  alkylsulfonylamino, (xxxiii) C 6  to C 12  arylsulfonylamino which may optionally be substituted with C 1  to C 6  alkyl, (xxxiv) C 1  to C 10  heteroarylsulfonylamino, (xxxv) C 1  to C 6  alkoxycarbonylamino, (xxxvi) C 1  to C 6  alkylcarbonylamino, (xxxvii) mono- or di-C 1  to C 6  alkylaminocarbonylamino, (xxxviii) C 6  to C 12  aryl, (xxxix) C 1  to C 10  heteroaryl, (xl) C 6  to C 10  aryloxy, (xli) C 1  to C 10  heteroaryloxy, (xlii) C 7  to C 16  aralkyloxy, (xliii) C 1  to C 10  heteroaryl-C 1  to C 6  alkyloxy, (xliv) aminosulfonyl, (xlv) mono- or di-C 1  to C 6  alkylaminosulfonyl, (xlvi) C 7  to C 16  aralkyloxycarbamoyl, and (xlvii) C 1  to C 10  heteroaryl-C 1  to C 6  alkyloxycarbamoyl; and 
 Z indicates (1) a bond or (2) CR 7 R 8  wherein R 7  and R 8  are, independently, 
 (A) a hydrogen atom, 
 (B) C 1  to C 6  alkyl which may optionally be substituted with 1 to 5 groups selected from the group consisting of (i) carboxyl, (ii) C 1  to C 6  alkoxycarbonyl, (iii) phenyl, (iv) hydroxyl, (v) C 1  to C 6  alkoxy, and (vi) a halogen atom, 
 (C) C 6  to C 12  aryl or C 1  to C 10  heteroaryl, which may optionally be substituted with 1 to 5 groups selected from the group consisting of (i) a halogen atom and (ii) an alkyl group which may optionally be substituted with 1 to 3 halogen atoms, 
 (D) C 3  to C 6  cycloalkyl which may optionally be substituted with 1 to 5 groups selected from (i) a halogen atom and (ii) an alkyl group which may optionally be substituted with 1 to 3 halogen atoms, 
 (E) —COOR S  wherein R 9  indicates a hydrogen atom or C 1  to C 6  alkyl, or 
 (F) CONR 10 R 11  wherein R 10  and R 11  are, independently,
 (a) a hydrogen atom, 
 (b) C 1  to C 6  alkyl which may optionally be substituted with 1 to 3 groups selected from the group consisting of (i) a halogen atom, (ii) C 3  to C 6  cycloalkyl, (iii) carboxyl, (iv) C 1  to C 6  alkoxycarbonyl, (v) C 1  to C 6  alkylcarbonyl, (vi) carbamoyl, (vii) mono-C 1  to C 6  alkylcarbamoyl, (viii) di-C 1  to C 6  alkylcarbamoyl, (ix) C 6  to C 12  aryl, and (x) C 1  to C 10  heteroaryl, 
 (c) OR 12  wherein R 12  indicates a hydrogen atom or C 1  to C 6  alkyl, or 
 (d) (1) a C 6  to C 14  aromatic hydrocarbon group, (2) a 5- to 8-membered aromatic heterocyclic group including 1 to 4 hetero atoms selected from a nitrogen atom, a sulfur atom, and an oxygen atom, other than a carbon atom, or (3) a bicyclic or tricyclic aromatic group formed by condensation of the above aromatic heterocyclic group and a C 6  to C 14  aromatic hydrocarbon ring, 
 
 wherein each of the groups (1) to (3) may optionally be substituted with 1 to 5 groups selected from the group consisting of (i) a halogen atom, (ii) nitro, (iii) cyano, (iv) C 1  to C 6  alkyl which may optionally be substituted with 1 to 3 halogen atoms, (v) C 2  to C 6  alkenyl which may optionally be substituted with 1 to 3 halogen atoms, (vi) C 2  to C 6  alkynyl which may optionally be substituted with 1 to 3 halogen atoms, (vii) C 3  to C 6  cycloalkyl, (viii) hydroxyl, (ix) C 1  to C 6  alkoxy which may optionally be substituted with 1 to 3 halogen atoms, (x) C 1  to C 5  alkylenedioxy, (xi) C 1  to C 6  alkylthio which may optionally be substituted with 1 to 3 halogen atoms, (xii) amino, (xiii) mono-C 1  to C 6  alkylamino, (xiv) di-C 1  to C 6  alkylamino, (xv) 5- to 6-membered cyclic amino, (xvi) C 1  to C 6  alkylcarbonyl, (xvii) carboxyl, (xviii) C 1  to C 6  alkoxycarbonyl, (xix) carbamoyl, (xx) thiocarbamoyl, (xxi) mono-C 1  to C 6  alkylcarbamoyl, (xxii) di-C 1  to C 6  alkylcarbamoyl, (xxiii) C 6  to C 10  arylcarbamoyl, (xxiv) C 1  to C 10  heteroarylcarbamoyl, (xxv) sulfo, (xxvi) C 1  to C 6  alkylsulfonyl, (xxvii) aminosulfonyl, and (xxviii) mono- or di-C 1  to C 6  alkylaminosulfonyl; 
 
       comprising undergoing a coupling reaction of the compound or a salt thereof having the formula (III): 
       
         
           
           
               
               
           
         
       
       with the compound or a salt thereof having the formula (IV) 
       
         
           
           
               
               
           
         
       
       wherein Q 2  and Q 3  independently indicate C 6  to C 10  aryloxy group which may optionally be substituted with 1 to 3 halogen atoms or nitro, or a halogen atom, and Y′ indicates —S(O) n — (wherein n indicates an integer of 1 or 2) or C(═O), 
       and the compound or salt thereof having the formula (V)