IMIDAZO[1,2-b]PYRIDAZINE COMPOUND

Abstract

The present invention provides a novel compound having an excellent corticotrophin-releasing-factor receptor antagonistic activity. That is, it provides a compound represented by the following formula or a salt thereof. Wherein R 1 denotes a hydrogen atom, a C 1-6 alkyl group, a C 1-6 alkoxy group and the like; R 2 denotes a halogen atom, a cyano group, a nitro group, a C 1-10 alkyl group, a C 2-10 alkenyl group, C 2-10 alkynyl group and the like; R 3 denotes a C 6-14 aromatic hydrocarbon cyclic group or a 5- to 14-membered aromatic heterocyclic group, each of which may have a substituent; and X, Y and X are independent of each other and each denotes N or CR 4 (wherein R 4 denotes a hydrogen atom, a halogen atom, a cyano group, a nitro group, an optionally halogenated C 1-6 alkyl group and the like) and, in this case, at least two of X, Y and Z denote CR 4 .

1 . A compound represented by the formula:  
       
         
           
           
               
               
           
         
       
       (wherein R 1  denotes a hydrogen atom, a halogen atom, a nitro group, a cyano group, a C 1-6  alkyl group, a C 2-8  alkenyl group, a C 2-8  alkynyl group, a C 3-8  cycloalkyl group, a C 3-8  cycloalkenyl group, a C 1-6  alkoxy group, a C 2-6  alkenyloxy group, or a group represented by —NR 1a R 1b  (R 1a  and R 1b  are the same as or different from each other and each denotes a hydrogen atom, a C 1-6  alkyl group, a C 2-6  alkenyl group, a C 2-6  alkynyl group, a C 1-6  alkylsulfinyl group, a C 1-6 alkylsulfonyl group or a C 1-7  aliphatic acyl group), —CO—NR 1a R 1b  (R 1a  and R 1b  have the same meanings as defined above, respectively), —CO-A 1  (A 1  denotes a C 1-6  alkyl group, a C 2-8  alkenyl group or a C 2-8  alkynyl group), -G 1 -A 2  (G 1  denotes —O—CO—, S, SO or SO 2 ; and A 2  denotes a C 1-6  alkyl group or a C 2-6  alkenyl group) or —SO 2 —NR 1a R 1b  (R 1a  and R 1b  have the same meanings as defined above, respectively), and further, the R 1  maybe substituted with at least one group selected from a halogen atom, a cyano group, a C 1-6  alkyl group, a C 2-8  alkenyl group, a C 2-8  alkynyl group, a C 1-6  alkoxy group, a C 1-6  alkenyloxy group, a C 1-6  alkylthio group and a C 2-6  alkenylthio group; 
 R 2  denotes:  
 (a) a halogen atom, a cyano group, a nitro group, a C 1-10  alkyl group, a C 2-10  alkenyl group, a C 2-10  alkynyl group, a C 3-8  cycloalkyl group, a C 3-8  cycloalkenyl group, a C 3-8  cycloalkyl C 1-6  alkyl group, a C 3-8  cycloalkyl C 2-6  alkenyl group, a C 1-10  alkoxy group, a C 2-6  alkenyloxy group, a C 1-10  alkoxy C 1-10  alkyl group, a C 1-6  alkoxy C 2-8  alkenyl group, a C 2-6  alkenyloxy C 1-6  alkyl group, a C 2-6 alkenyloxy C 2-6  alkenyl group, a group represented by —NR 2a R 2b  (R 2a  and R 2b  are independent of each other and each denotes a hydrogen atom, a C 1-8  alkyl group, a C 2-8  alkenyl group, a C 2-6  alkynyl group, a C 1-6  hydroxyalkyl group, a C 1-6  alkyl group substituted with a 5-to 14-membered non-aromatic heterocyclic group, a C 1-6  alkylthio group, a C 1-6  alkylsulfinyl group, a C 1-6  alkylsulfonyl group, a C 1-6  alkoxy C 1-6  alkyl group, a C 1-6  alkylthio C 1-6  alkyl group, an aminocarbonyl C 1-6  alkyl group, a heteroarylcarbonyl group, a C 3-8  cycloalkyl group, a C 3-8  cycloalkyl C 1-6  alkyl group, a heteroaryl C 1-6  alkyl group, an aryl C 1-6  alkyl group, an aryl group, a 5- to 14-membered heterocyclic group, a C 1-6  alkoxycarbonyl group or a C 2-6  alkenyloxycarbonyl group), —CO—NR 2a R 2b  (R 2a  and R 2b  have the same meanings as defined above, respectively), —CO-A 3  (A 3  denotes a hydrogen atom, a hydroxyl group, a C 1-6  alkyl group, a C 2-8  alkenyl group, a C 2-8  alkynyl group, a C 1-6  alkoxy group, a C 2-8  alkenyloxy group, an aryl group or a heteroaryl group), —O—C(O)-A 4  (A 4  denotes a C 1-6  alkyl group, a C 2-8  alkenyl group or a C 2-8  alkynyl group) or -G 2 -A 5  (G 2  denotes S, SO or SO 2 ; and A 5  denotes a C 1-6  alkyl group or a C 2-6  alkenyl group), or a 5- to 14-membered non-aromatic heterocyclic group, or  
 (b) maybe bound together with R 1  to form a cycle, and further, in the case of (a) or (b), R 2  may be substituted with at least one group selected from a halogen atom, a hydroxyl group, a cyano group, a C 1-6  alkyl group, a C 2-6  alkenyl group, a C 2-6  alkynyl group, a C 3-8  cycloalkyl group, a C 3-8  cycloalkenyl group, a C 1-6  alkoxy group, a C 2-6  alkenyloxy group, a C 1-6  alkylthio group, a C 2-6 alkenylthio group, —NR 2a R 2b  (R 2a  and R 2b  have the same meanings as defined above, respectively), an aryl group and a heteroaryl group;  
 R 3  denotes a C 6-14  aromatic hydrocarbon cyclic group or a 5- to 14-membered aromatic heterocyclic group, each of which may have a substituent; and  
 X, Y and Z are independent of each other and each denotes (a) N or (b) CR 4  (wherein R 4  (aa) denotes a hydrogen atom, a halogen atom, a cyano group, a nitro group, an optionally halogenated C 1-6  alkyl group, a C 2-6  alkenyl group, a C 2-6  alkynyl group, a C 3-8  cycloalkyl group, a C 3-8  cycloalkenyl group, a C 1-6  alkoxy group, a C 2-6  alkenyloxy group, —NR 4a R 4b  (wherein R 4a  and R 4b  are independent of each other and each denotes a hydrogen atom, a C 1-8  alkyl group, a C 2-8  alkenyl group, a C 2-6  alkynyl group, a C 1-6  alkylthio group, a C 1-6  alkylsulfinyl group, a C 1-6  alkylsulfonyl group, a C 1-6  alkoxy C 1-6  alkyl group, a C 3-8  cycloalkyl group, a C 3-8  cycloalkyl C 1-6  alkyl group, a heteroaryl C 1-6  alkyl group, an aryl C 1-6  alkyl group, an aryl group, a 5- to 14-membered heterocyclic group, a C 1-6  alkoxycarbonyl group or a C 2-6  alkenyloxycarbonyl group) or -G 3 -A 6  (wherein G 3  denotes S, SO or SO 2 ; A 6  denotes a C 1-6  alkyl group or a C 2-6  alkenyl group), or (bb) R 4 s, or R 2  and R 4  may be bound together to form a ring); in this case, at least two of X, Y and Z denote CR 4  (R 4  has the same meaning as defined above),  
 provided that, in the above definition, compounds in the following cases (1) to (4) are excluded:  
 (1) the case where R 1  and R 2  are a methyl group, X, Y and Z are CH, and R 3  is a 2,4-dichlorophenyl group,  
 (2) the case where R 1  is a trifluoromethyl group, R 2  is a fluorine atom or a bromine atom, X is N, Y is ═C(CH 3 )—, Z is CH, and R 3  is a phenyl group,  
 (3) the case where R 1  is a trifluoromethyl group, R 2  is an ethoxycarbonyl group or an amide group, X is N, Y is ═C(CH 3 )—, Z is CH, and R 3  is a 3-chlorophenyl group, and  
 (4) the case where R 1  is a hydrogen atom, R 2  is a 4-morpholinylmethyl group, X is N, Y is ═CR′— (R 1  denotes a phenyl group), Z is CH, and R 3  is a phenyl group) or a salt thereof.  
 
     
     
         2 . The compound according to  claim 1  or a salt thereof, wherein R 1  is a C 1-6  alkyl group, a C 2-8  alkenyl group, a C 2-8  alkynyl group, a C 1-6  alkoxy group, a C 1-6  alkylthio group, a C 1-6  alkylsulfinyl group or a C 1-6  alkylsulfonyl group.  
     
     
         3 . The compound according to  claim 1  or a salt thereof, wherein R 1  is a methyl group, an ethyl group, a n-propyl group, an iso-propyl group, a methoxy group, an ethoxy group, a n-propyloxy group, an iso-propyloxy group, a methylthio group, an ethylthio group, an-propylthio group, an iso-propylthio group, a methylsulfinyl group, an ethylsulfinyl group, a methylsulfonyl group or an ethylsulfonyl group.  
     
     
         4 . The compound according to  claim 1  or a salt thereof, wherein R 1  is -G 4 -CH 3  (wherein G 4  denotes a single bond, CH 2 , O or S).  
     
     
         5 . The compound according to  claim 1  or a salt thereof, wherein R denotes a C 1-6 alkyl group, C 1-6 alkoxy C 1-6 alkyl group, a C 1-6 alkylsulfonyl group, a C 2-6 alkenylsulfonyl group or —NR 2a R 2b  (R 2a  and R 2b  have the same meanings as defined above), each of which may be substituted.  
     
     
         6 . The compound according to  claim 1  or a salt thereof, wherein R 2  is —NR 2aa R 2bb  (wherein R 2aa  and R 2bb  are independent of each other and each denotes a hydrogen atom, a C 1-8  alkyl group, a C 2-8  alkenyl group, a C 2-6  alkynyl group, a C 1-6  alkyl group substituted with a 5- to 14-membered non-aromatic heterocyclic group, a C 1-8  alkoxy group, a C 1-8  alkoxy C 1-8  alkyl group, a C 1-6  alkylsulfinyl group, a C 1-6  alkylsulfonyl group, a C 3-8  cycloalkyl group, a C 3-8 cycloalkyl C 1-6 alkyl group or a 5- to 14-membered heterocyclic group, and further, the R 2aa  and R 2bb  are independent of each other and each may be substituted with a halogen atom).  
     
     
         7 . The compound according to  claim 1  or a salt thereof, wherein R 2  is a di(C 1-6 alkyl)amino group.  
     
     
         8 . The compound according to  claim 1  or a salt thereof, wherein R 3  is a phenyl group or a pyridyl group, each of which may be substituted.  
     
     
         9 . The compound according to  claim 1  or a salt thereof, wherein R 3  is a phenyl group or a pyridyl group, each of which may be substituted with 1 to 4 group (s) selected from a halogen atom, a C 1-6  alkyl group, a halogeno-C 1-6  alkyl group, a C 1-6  alkoxy group, a halogeno-C 1-6  alkoxy group, a C 1-6  alkylthio group and a 5- to 8-membered aromatic heterocyclic group.  
     
     
         10 . The compound according to  claim 1  or a salt thereof, wherein R 3  is a phenyl group or a pyridyl group, each of which may be substituted with 1 to 3 group(s) selected from a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, a trifluoromethyl group, a methoxy group, a trifluoromethoxy group, a methylthio group and a pyrrolyl group.  
     
     
         11 . The compound according to  claim 1  or a salt thereof, wherein any one of X, Y and Z is N, and remaining two are CR 4′  (wherein R 4′  denotes a hydrogen atom, a halogen atom, a cyano group, a C 1-6 alkyl group or a C 1-6 alkoxy group).  
     
     
         12 . The compound according to  claim 1  or a salt thereof, wherein X and Y are CR 4′  (wherein R 4′  has the same meaning as defined above); and Z is N.  
     
     
         13 . The compound according to  claim 1  or a salt thereof, wherein X, Y and Z are a group represented by CR 4′  (wherein R 4′  has the same meaning as defined above).  
     
     
         14 . The compound according to any one of  claims 11  to  13  or a salt thereof, wherein R 4′  is a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a methoxy group or an ethoxy group.  
     
     
         15 . The compound according to any one of  claims 11  to  13  or a salt thereof, wherein R 4  is a hydrogen atom.  
     
     
         16 . The compound according to  claim 1  which is represented by the following formula or a salt thereof.  
       
         
           
           
               
               
           
         
       
       Wherein X′ and Z′ are independent of each other and denotes N or CH (in this case, at least one of X′ and Z′ denotes CH) ; and G 4 , R 2  and R 3  have the same meanings as defined above.  
     
     
         17 . The compound according to  claim 16  or a salt thereof, wherein R 2  is —NR 2aa R 2bb  (wherein R 2aa  and R 2bb  are independent of each other and each denotes a hydrogen atom, a C 1-8  alkyl group, a C 2-8  alkenyl group, a C 2-6  alkynyl group, a C 1-6  alkyl group which may be substituted with a 5- to 14-membered non-aromatic heterocyclic group, a C 1-8  alkoxy group, a C 1-8  alkoxy C 1-8  alkyl group, a C 1-6  alkylsulfinyl group, a C 1-6  alkylsulfonyl group, a C 3-8  cycloalkyl group, a C 3-8  cycloalkyl C 1-6  alkyl group or a 5- to 14-membered heterocyclic group, and further, the R 2aa  and R 2bb  are independent of each other and each may be substituted with a halogen atom).  
     
     
         18 . The compound according to  claim 16  or a salt thereof, wherein R 2  is a di(C 1-6 alkyl)amino group.  
     
     
         19 . The compound according to  claim 16  or a salt thereof, wherein R 3  is a phenyl group or a pyridyl group, each of which may be substituted.  
     
     
         20 . The compound according to  claim 16  or a salt thereof, wherein R 3  is a phenyl group or a pyridyl group, each of which may be substituted with 1 to 4 group(s) selected from a halogen group, a C 1-6 alkyl group, a halogeno-C 1-6 alkyl group, a halogeno-C 1-6 alkoxy group, a C 1-6 alkoxy group, a C 1-6 alkylthio group and a 5- to 8-membered aromatic heterocyclic group.  
     
     
         21 . The compound according to  claim 1  which is represented by the following formula or a salt thereof.  
       
         
           
           
               
               
           
         
       
       Wherein Z denotes N or CH; the ring M denotes a benzene ring which may further have a substituent; and G 4 , R 2  and R 2b  have the same meanings as defined above.  
     
     
         22 . The compound according to  claim 21  or a salt thereof, wherein R 2a  and R 2b  are independent of each other and each represents a hydrogen atom, a C 1-8  alkyl group, a C 2-8  alkenyl group, a C 2-6  alkynyl group, a C 1-6  alkyl group which may be substituted with a 5- to 14-membered non-aromatic heterocyclic group, a C 1-8  alkoxy C 1-8  alkyl group, a C 3-8  cycloalkyl group or a C 3-8  cycloalkyl C 1-6  alkyl group, and further, each of which may be substituted with a halogen atom.  
     
     
         23 . The compound according to  claim 21  or a salt thereof, wherein R 2a  and R 2b  are a C 1-6 alkyl group.  
     
     
         24 . The compound according to  claim 21  or a salt thereof, wherein the ring M is a benzene ring which may be further substituted with 1 to 3 group(s) selected from a halogen atom, a C 1-6 alkyl group, a C 1-6 alkoxy group, a halogeno-C 1-6 alkyl group and a halogeno-C 1-6 alkoxy group.  
     
     
         25 . The compound according to  claim 1  or a salt thereof, wherein the compound is: 
 N-(2-ethyl-8-mesitylimidazo[1,2-a]pyrazin-3-yl)-N,N-dipropylamine hydrochloride,    N-(2-ethyl-8-mesitylimidazo[1,2-a]pyrazin-3-yl)-N-(1-ethylpropyl)amine,    N-[8-(2-chloro-4-methoxyphenyl)-2-ethylimdazo[1,2-a]pyrazin-3-yl]-N,N-dipropylamine hydrochloride,    N-cyclopropylmethyl-N-[8-(2,4-dichlorophenyl)-2-ethylimidazo[1,2-a]pyrazin-3-yl]-N-isobutylamine,    N-[8-(2,4-dichlorophenyl)-2-ethylimidazo[1,2-a]pyrazin-3-yl]-N-propyl-N-tetrahydro-3-thiophenylamine,    N3,N3-dipropyl-2-isopropyl-8-(2-methoxy-4,6-dimethylphenyl)imidazo[1,2-a]pyrazin-3-amine,    N-[2-ethyl-8-(6-methyl-1,3-benzodioxol-5-yl)imidazo[1,2-a]pyrazin-3-yl]-N,N-dipropylamine,    N-[2-ethyl-8-(4-methoxy-2,5-dimethylphenyl)imidazo[1,2-a]pyrazin-3-yl]-N,N-dipropylamine,    N-cyclopropylmethyl-N-[8-(2,4-dichlorophenyl)-2-ethylimidazo-[1,2-a]pyrazin-3-yl]-N-(2-methoxyethyl)amine hydrochloride,    N-[8-(2-chloro-4-methoxyphenyl)-2-ethylimidazo[1,2-a]pyrazin-3-yl]-N,N-dicyclopropylmethylamine,    N-8-[5-chloro-4-(2,5-dimethyl-1H-1-pyrroyl)-2-methoxyphenyl]-2-ethylimidazo[1,2-a]pyrazin-3-yl-N,N-dicyclopropylmethylamine,    N-[8-(2,4-dichlorophenyl)-2-ethyl-6-methylimidazo[1,2-a]pyrazin-3-yl]-N,N-dipropylamine hydrochloride,    N3,N3-dipropyl-5-bromo-8-(2,4-dichlorophenyl)-2-ethylimidazo[1,2-a]pyrazin-3-amine,    8-(2,4-dichlorophenyl)-3-(dipropylamino)-2-ethylimidazo[1,2-a]pyrazin-6-yl cyanide,    N-[8-(2,4-dichlorophenyl)-2-ethyl-6-methoxyimidazo[1,2-a]pyrazin-3-yl]-N,N-dipropylamine,    N-[6-chloro-2-ethyl-8-(2-methoxy-4,6-dimethylphenyl)imidazo[1,2-a]pyrazin-3-yl]-N,N-dipropylamine,    N3,N3-dipropyl-8-(2,4-dichlorophenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-amine,    N,N-dicyclopropylmethyl-N-[8-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]amine,    N-[8-(2-chloro-4-methoxyphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylmethyl-N-propylamine,    N-[8-(2-bromo-4-methoxyphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylmethyl-N-(3-fluoropropyl)amine,    N-[8-(2-chloro-6-methoxy-4-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]-N,N-dicyclopropylmethylamine,    N-[8-(2-chloro-4-methoxyphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylmethyl-N-isobutylamine    N-cyclopropylmethyl-N-[8-[2-methyl-4-(methylsulfinyl)phenyl]-2-(methylsulfinyl)imidazo[1,2-a]pyrazin-3-yl]-N-propylamine,    N-[8-(2-chloro-4-methoxyphenyl)-2-(methylsulfonyl)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylmethyl-N-propylamine,    N-[8-[2-chloro-4-(trifluoromethoxy)phenyl]-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]-N,N-dicyclopropylmethylamine,    1-[[8-[2-chloro-4-(trifluoromethoxy)phenyl]-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl](cyclopropylmethyl)amino]-2-propanol,    2-[[8-[2-chloro-4-(trifluoromethoxy)phenyl]-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl](cyclopropylmethyl)amino]acetamide,    4-[3-[di(cyclopropylmethyl)amino]-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-8-yl]-3-methoxybenzonitrile,    N,N-dicyclopropylmethyl-N-[8-(2-methoxy-4-tetrahydro-1H-1-pyrrolylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]amine,    N2-[8-[2-chloro-4-(trifluoromethoxy)phenyl]-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]-N2-cyclopropylmethyl-2-furamide,    N-[8-[2-chloro-4-(trifluoromethoxy)phenyl]-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylmethyl-N-(2-furylmethyl)amine,    N-[8-[2-chloro-4-(trifluoromethoxy)phenyl]-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylmethyl-N-(2-morpholinoethyl)amine,    N-[8-[2-chloro-4-(trifluoromethoxy)phenyl]-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylmethyl-N-[2-(1H-1-pyrazoyl)ethyl]amine,    N-[8-[2-chloro-4-(trifluoromethoxy)phenyl]-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylmethyl-N-[2-(1H-1-imidazoyl)ethyl]amine,    2-[2-ethyl-3-(1-ethylpropyl)imidazo[1,2-a]pyrazin-8-yl]-3,5-dimethylphenyl methyl ether,    3-(1-ethoxybutyl)-2-ethyl-8-(2-methoxy-4,6-dimethylphenyl)imidazo[1,2-a]pyrazine,    1-[8-(2-chloro-4-methoxyphenyl)-2-ethylimidazo[1,2-a]pyrazin-3-yl]-1-butanone O1-methyloxime,    3-(1-ethoxybutyl)-8-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyrazine,    N-[8-(2-chloro-4-methoxyphenyl)-2-methoxyimidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylmethyl-N-propylamine,    N-[2-ethyl-8-(4-methoxy-2-methylphenyl)imidazo[1,2-b]pyridazin-3-yl]-N,N-dipropylamine,    N-[2-ethyl-8-(2-methoxy-4,6-dimethylphenyl)imidazo[1,2-b]pridazin-3-yl]-N,N-dipropylamine,    N,N-dicyclopropylmethyl-N-[2-ethyl-8-(2-methoxy-4,6-dimethylphenyl)imidazo[1,2-b]pyridazin-3-yl]amine,    N-[8-(4-methoxy-2-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-b]pyridazin-3-yl]-N,N-dipropylamine,    N-[8-(2,4-dichlorophenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylamine,    N-[8-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylamine,    N-[8-(2,6-dimethoxy-4-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylamine,    N-[8-(2,4-dimethoxy-6-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylamine,    N-[8-(2-chloro-6-methoxy-4-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylamine,    N-[8-(2,4-dichlorophenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-propyl-N-(2-propynyl)amine,    N-[8-(4-chloro-2-methoxyphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylamine,    N-[8-(2,6-dimethoxy-4-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl-N-propyl-N-(3-thienyl)amine,    N-[8-(4-methoxy-2-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylamine,    N-cyclobutylmethyl-N-[8-(2,6-dimethoxy-4-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-propylamine,    N-[8-(4-chloro-2,6-dimethoxyphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylamine,    N-[8-(4-chloro-2,6-dimethoxyphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-cyclobutylmethyl-N-propylamine,    N-butyl-N-cyclobutylmethyl-N-[8-(2,6-dimethoxy-4-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]amine    N-cyclobutylmethyl-N-cyclopropylmethyl-N-[8-(2,6-dimethoxy-4-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]amine,    N3,N3-dipropyl-8-[6-(dimethylamino)-4-methyl-3-pyridyl]-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-amine,    N-[8-(2,6-dimethoxy-4-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-propyl-N-tetrahydro-2H-4-pyranylamine,    N3-cyclobutylmethyl-N3-propyl-8-[6-(dimethylamino)-4-methyl-3-pyridyl]-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-amine,    N3-cyclobutylmethyl-N3-(3-fluoropropyl)-8-[6-(dimethylamino)-4-methyl-3-pyridyl]-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-amine,    N3,N3-dicyclopropylmethyl-8-[6-(dimethylamino)-4-methyl-3-pyridyl]-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-amine,    N3-propyl-N3-tetrahydro-2H-4-pyranyl-8-[6-(dimethylamino)-4-methyl-3-pyridyl]-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-amine,    N-[8-(2,6-dimethoxy-4-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-cyclobutylmethyl-N-tetrahydro-2H-4-pyranylamine, or    N-cyclopropylmethyl-N-[8-(2,6-dimethoxy-4-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-tetrahydro-2H-4-pyranylamine.    
     
     
         26 . A pharmaceutical composition comprising the compound according to  claim 1  or a salt thereof, and a pharmacologically acceptable carrier.  
     
     
         27 . The composition according to  claim 26 , which is an agent for treating or preventing a disease to which corticotrophin-releasing factor (hereinafter, referred to as “CRF”) and/or a CRF receptor relate.  
     
     
         28 . The composition according to  claim 26 , which is a CRF receptor antagonist.  
     
     
         29 . The composition according to  claim 26 , which is an antagonist for a CRF1 receptor or CRF2 receptor.  
     
     
         30 . The composition according to  claim 26 , which is an agent for treating or preventing depression, depressive symptom, mania, anxiety, generalized anxiety disorder, panic disorder, phobia, compulsive disorder, post traumatic stress disorder, Tourette syndrome, autism, emotional disorder, sentimental disorder, bipolar disorder, cyclothymia or schizophrenia.  
     
     
         31 . The composition according to  claim 30 , which is an agent for treating or preventing depressive symptoms which is great depression, monostotic depression, recurrent depression, infant tyrannism by depression or postpartum depression.  
     
     
         32 . The composition according to  claim 26 , which is an agent for treating or preventing peptic ulcer, irritable bowel syndrome, ulcerative colitis, Crohn's disease, diarrhea, coprostasis, postoperational ileus, gastrointestinal function abnormality associated with stress or neural vomiting.  
     
     
         33 . The composition according to  claim 26 , which is an agent for treating or preventing Alzheimer's disease, Alzheimer-type senile dementia, neurodegenerative disease, multi-infarct dementia, senile dementia, neurotic anorexia, diet disorder, obesity, diabetes, alcohol dependence, pharmacophilia, drug abstinence symptoms, alcohol abstinence symptoms, sleep disorder, insomnia, migraine, stress headache, myotonic headache, ischemic neuropathy, excitation toxic neuropathy, cerebral apoplexy, progressive supranuclear palsy, amyotrophic lateral sclerosis, multiple sclerosis, muscular convulsion, chronic fatigue syndrome, mental social growth failure, epilepsy, head trauma, spinal trauma, graphospasm, spasmodic torticollis, muscular convulsion, neck-shoulder-arm syndrome, primary glaucoma, Meniere syndrome, autonomic imbalance, alopecia, neurosis, hypertension, cardiovascular disorder, tachycardia, congestive cardioplegia, hyperpnea syndrome, bronchial asthma, apnea syndrome, infant sudden death syndrome, inflammatory disorder, pain, allergic disease, impotence, climacteric disorder, fertilization disorder, infertility, cancer, immunefunction abnormality upon infection with HIV, immune function abnormality by stress, hemorrhagic stress, Cushing syndrome, thyroid function disorder, encephalomyelitis, acromegaly, incontinence or osteoporosis.  
     
     
         34 . Use of the compound according to  claim 1  or a salt thereof for producing an antagonist for a CRF receptor.  
     
     
         35 . Use of the compound according to  claim 1  or a salt thereof for producing an antagonist for a CRF1 receptor or a CRF2 receptor.  
     
     
         36 . Use of the compound according to  claim 1  or a salt thereof for producing an agent for treating or preventing depression, depressive symptom, mania, anxiety, generalized anxiety disorder, panic disorder, phobia, compulsive disorder, posttraumatic stress disorder, Tourette syndrome, autism, emotional disorder, sentimental disorder, bipolar disorder, cyclothymia, schizophrenia, peptic ulcer, irritable bowel syndrome, ulcerative colitis, Crohn's disease, diarrhea, coprostasis, postoperational ileus, gastrointestinal function abnormality associated with stress or neural vomiting.  
     
     
         37 . A method for treating or preventing a disease to which a CRF receptor relate, which comprises administering a therapeutically effective amount of the compound according to  claim 1  or a salt thereof once or multiple times to a patient who is suffering from a disease to which a CRF receptor relate.  
     
     
         38 . A medicine comprising the compound according to  claim 1  or a salt thereof as the active ingredient.  
     
     
         39 . The medicine according to  claim 38 , which is an agent for treating or preventing a disease to which a CRF and/or CRF receptor relate.  
     
     
         40 . The medicine according to  claim 38 , which is a CRF receptor antagonist.  
     
     
         41 . The medicine according to  claim 38 , which is an antagonist for a CRF1 receptor or a CRF2 receptor.  
     
     
         42 . The medicine according to  claim 38 , which is an agent for treating or preventing depressive symptom, mania, anxiety, generalized anxiety disorder, panic disorder, phobia, compulsive disorder, posttraumatic stress disorder, Tourette syndrome, autism, emotional disorder, sentimental disorder, bipolar disorder, cyclothymia or schizophrenia.  
     
     
         43 . The medicine according to  claim 42 , which is an agent for treating or preventing depressive symptoms which is great depression, monostotic depression, recurrent depression, infant tyrannism by depression or postpartum depression.  
     
     
         44 . The medicine according to  claim 38 , which is an agent for treating or preventing peptic ulcer, irritable bowel syndrome, ulcerative colitis, Crohn's disease, diarrhea, coprostasis, postoperational ileus, gastrointestinal function abnormality associated with stress or neural vomiting.  
     
     
         45 . The medicine according to  claim 38 , which is an agent for treating or preventing Alzheimer's disease, Alzheimer-type senile dementia, neurodegenerative disease, multi-infarct dementia, senile dementia, neurotic anorexia, diet disorder, obesity, diabetes, alcohol dependence, pharmacophilia, drug abstinence symptoms, alcohol abstinence symptoms, sleep disorder, insomnia, migraine, stress headache, myotonic headache, ischemic neuropathy, excitation toxic neuropathy, cerebral apoplexy, progressive supranuclear palsy, amyotrophic lateral sclerosis, multiple sclerosis, muscular convulsion, chronic fatigue syndrome, mental social growth failure, epilepsy, head trauma, spinal trauma, graphospasm, spasmodic torticollis, muscular convulsion, neck-shoulder-arm syndrome, primary glaucoma, Meniere syndrome, autonomic imbalance, alopecia, neurosis, hypertension, cardiovascular disorder, tachycardia, congestive cardioplegia, hyperpnea syndrome, bronchial asthma, apnea syndrome, infant sudden death syndrome, inflammatory disorder, pain, allergic disease, impotence, climacteric disorder, fertilization disorder, infertility, cancer, immune function abnormality upon infection with HIV, immune function abnormality by stress, hemorrhagic stress, Cushing syndrome, thyroid function disorder, encephalomyelitis, acromegaly, incontinence or osteoporosis.  
     
     
         46 . Use of the compound according to  claim 1  or a salt thereof, for producing an agent for treating or preventing a disease to which a CRF and/or CRF receptor relate.  
     
     
         47 . The use according to  claim 36 , wherein the depressive symptom is great depression, monostotic depression, recurrent depression, infant tyrannism by depression or postpartum depression.  
     
     
         48 . Use of the compound according to  claim 1  or a salt thereof, for producing an agent for treating or preventing Alzheimer's disease, Alzheimer-type senile dementia, neurodegenerative disease, multi-infarct dementia, senile dementia, neurotic anorexia, diet disorder, obesity, diabetes, alcohol dependence, pharmacophilia, drug abstinence symptoms, alcohol abstinence symptoms, sleep disorder, insomnia, migraine, stress headache, myotonic headache, ischemic neuropathy, excitation toxic neuropathy, cerebral apoplexy, progressive supranuclear palsy, amyotrophic lateral sclerosis, multiple sclerosis, muscular convulsion, chronic fatigue syndrome, mental social growth failure, epilepsy, head trauma, spinal trauma, graphospasm, spasmodic torticollis, muscular convulsion, neck-shoulder-arm syndrome, primary glaucoma, Meniere syndrome, autonomic imbalance, alopecia, neurosis, hypertension, cardiovascular disorder, tachycardia, congestive cardioplegia, hyperpnea syndrome, bronchial asthma, apnea syndrome, infant sudden death syndrome, inflammatory disorder, pain, allergic disease, impotence, climacteric disorder, fertilization disorder, infertility, cancer, immune function abnormality upon infection with HIV, immunefunction abnormality by stress, hemorrhagic stress, Cushing syndrome, thyroid function disorder, encephalomyelitis, acromegaly, incontinence or osteoporosis.  
     
     
         49 . A method for treating or preventing a disease to which a CRF and/or CRF receptor relate, by administering a pharmacologically effective amount of the compound according to  claim 1  or a salt thereof to a patient.  
     
     
         50 . A method for treating or preventing a disease against which the CRF receptor antagonistic activity is efficacious for treatment or prevention, by administering a pharmacologically effective amount of the compound as defined in  claim 1  or a salt thereof to a patient.  
     
     
         51 . A method for treating or preventing a disease against which a CRF1 receptor or CRF2 receptor antagonistic activity is efficacious for treatment or prevention, by administering a pharmacologically effective amount of the compound as defined in  claim 1  or a salt thereof to a patient.  
     
     
         52 . A method for treating or preventing depression, depressive symptom, mania, anxiety, generalized anxiety disorder, panic disorder, phobia, compulsive disorder, posttraumatic stress disorder, Tourette syndrome, autism, emotional disorder, sentimental disorder, bipolar disorder, cyclothymia, schizophrenia, peptic ulcer, irritable bowel syndrome, ulcerative colitis, Crohn's disease, diarrhea, coprostasis, postoperational ileus, gastrointestinal function abnormality associated with stress or neural vomiting, by administering a pharmacologically effective amount of the compound according to  claim 1  or a salt thereof to a patient.  
     
     
         53 . The method according to  claim 52 , wherein the depressive symptom is great depression, monostotic depression, recurrent depression, infant tyrannism by depression or postpartum depression.  
     
     
         54 . A method for treating or preventing Alzheimer's disease, Alzheimer-type senile dementia, neurodegenerative disease, multi-infarct dementia, senile dementia, neurotic anorexia, diet disorder, obesity, diabetes, alcohol dependence, pharmacophilia, drug abstinence symptoms, alcohol abstinence symptoms, sleep disorder, insomnia, migraine, stress headache, myotonic headache, ischemic neuropathy, excitation toxic neuropathy, cerebral apoplexy, progressive supranuclear palsy, amyotrophic lateral sclerosis, multiple sclerosis, muscular convulsion, chronic fatigue syndrome, mental social growth failure, epilepsy, head trauma, spinal trauma, graphospasm, spasmodic torticollis, muscular convulsion, neck-shoulder-arm syndrome, primary glaucoma, Meniere syndrome, autonomic imbalance, alopecia, neurosis, hypertension, cardiovascular disorder, tachycardia, congestive cardioplegia, hyperpnea syndrome, bronchial asthma, apnea syndrome, infant sudden death syndrome, inflammatory disorder, pain, allergic disease, impotence, climacteric disorder, fertilization disorder, infertility, cancer, immune function abnormality upon infection with HIV, immune function abnormality by stress, hemorrhagic stress, Cushing syndrome, thyroid function disorder, encephalomyelitis, acromegaly, incontinence or osteoporosis, by administering a pharmacologically effective amount of the compound according to  claim 1  or a salt thereof to a patient.