US2005208582A1PendingUtilityA1

Pyrazole compounds and pharmaceutical compositions comprising the compound

51
Assignee: OHI NORIHITOPriority: May 31, 2002Filed: May 30, 2003Published: Sep 22, 2005
Est. expiryMay 31, 2022(expired)· nominal 20-yr term from priority
Inventors:Norihito OhiNobuaki SatoMotohiro SoejimaTakashi DokoTaro TerauchiYoshimitsu NaoeTakafumi Motoki
A61P 43/00A61P 37/06A61P 37/02A61P 25/16A61P 25/28A61P 3/00A61P 25/02A61P 25/00A61P 25/14A61P 29/00A61K 31/42C07D 471/04A61K 31/5377A61K 31/4184A61K 31/4245A61K 31/497C07D 401/06C07D 413/14C07D 495/04A61K 31/4439A61K 31/437A61K 31/4196A61K 31/4162A61K 31/416C07D 405/06C07D 409/04A61K 31/422C07D 403/06C07D 487/04A61P 21/00C07D 413/04A61K 31/4178A61K 31/4985A61K 31/55A61K 31/407C07D 231/56A61K 31/506A61K 31/43C07D 409/06A61K 31/427A61K 31/454A61K 31/496A61K 31/444C07D 403/04
51
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Claims

Abstract

The present invention provides a novel compound having an excellent JNK inhibitory effect. That is, it provides a compound represented by the following formula, a salt thereof or a hydrate of them. Wherein R 1 designates —(CO h —(NR a ) j —(CR b ═CR c ) k —Ar (wherein R a , R b and R c each independently designate a hydrogen atom, a halogen atom, hydroxyl group, an optionally substituted C 1-6 alkyl group or the like; Cy designates a 5- or 6-membered heteroaryl; and V each independently designate the formula -L-X—Y (wherein L designates a single bond, an optionally substituted C 1-6 alkylene group or the like; X designates a single bond or the formula -A- (wherein A designates NR 2 , O, CO, S, SO or SO 2 ) and so on; and Y designates a hydrogen atom, a halogen atom, nitro group or the like).

Claims

exact text as granted — not AI-modified
1 . A compound represented by the formula (I), a salt thereof or a hydrate of them.  
       
         
           
           
               
               
           
         
       
       Wherein, R 1  designates a group represented by the formula —(CO h —(NR a ) j —(CR b ═CR c ) k —Ar (wherein R a , R b  and R c  each independently designate a hydrogen atom, halogen atom, hydroxyl group, an optionally substituted C 1-6  alkyl group, an optionally substituted C 2-6  alkenyl group, an optionally substituted C 1-6  alkoxy group, an optionally substituted C 2-6  alkenyloxy group, an optionally substituted C 1-6  alkylthio group, an optionally substituted C 2-6  alkenylthio group, an optionally substituted C 3-8  cycloalkenyl group, an optionally substituted 4- to 14-membered non-aromatic heterocyclic group, an optionally substituted C 6-14  aryl group or an optionally substituted 5- to 14-membered heteroaryl group; Ar designates an optionally substituted C 6-14  aryl group or an optionally substituted 5- to 14-membered heteroaryl group; and h, j and k each independently designate 0 or 1); 
 Cy designates a 5- to 6-membered heteroaryl group;  
 V designates a group represented by the formula -L-X—Y (wherein, L designates a single bond, an optionally substituted C 1-6  alkylene group, an optionally substituted C 2-6  alkenylene group or an optionally substituted C 2-6  alkynylene group; X designates a single bond, or a group represented by —NR 7 —, —O—, —CO—, —S—, —SO—, —SO 2 —, —CO—NR 8 -Z-, —C(O)O—, —NR 8 —CO-Z-, —NR 8 —C(O)O—, —NR 8 —S—, —NR 8 —SO—, —NR 8 —SO 2 -Z-, —NR 9 —CO—NR 10 —, —NR 9 —CS—NR 10 —, —S(O) m —NR 11 -Z-, —C(═NR 12 )—NR 13 —, —OC(O)—, —OC(O)—NR 14 — or —CH 2 —NR 8 —COR 7 — (wherein R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13  and R 14  each independently designate a hydrogen atom, halogen atom, hydroxyl group, an optionally substituted C 1-6  alkyl group, an optionally substituted C 2-6  alkenyl group, an optionally substituted C 2-6  alkynyl group, an optionally substituted C 1-6  alkoxy group, an optionally substituted C 2-6  alkenyloxy group, an optionally substituted C 1-6  alkylthio group, an optionally substituted C 2-6  alkenylthio group, an optionally substituted C 3-8 cycloalkyl group, an optionally substituted C 3-8 cycloalkenyl group, an optionally substituted 4- to 14-membered non-aromatic heterocyclic group, an optionally substituted C 6-14  aryl group or an optionally substituted 5- to 14-membered heteroaryl group, Z designates a single bond or an optionally substituted C 1-6  alkylene group, and m designates 0, 1 or 2);  
 Y designates any one group selected from the group consisting of a hydrogen atom, halogen atom, nitro group, hydroxyl group, cyano group, carboxyl group or an optionally substituted C 1-6  alkyl group, an optionally substituted C 2-6  alkenyl group, an optionally substituted C 2-6  alkynyl group, an optionally substituted C 1-6  alkoxy group, an optionally substituted C 3-8  cycloalkyl group, an optionally substituted C 3-8  cycloalkenyl group, an optionally substituted 4- to 14-membered non-aromatic heterocyclic group, an optionally substituted C 6-14  aryl group, an optionally substituted 5- to 14-membered heteroaryl group, an optionally substituted amino group and a group represented by the formula —W—R 15  (wherein W designates CO or SO 2 ; R 15  designates an optionally substituted C 1-6  alkyl group, an optionally substituted amino group, an optionally substituted C 6-14  aryl group or an optionally substituted 5- to 14-membered heteroaryl group)); and  
 n designates 0, 1, 2, 3 or 4, and when n is 2 or more, plural Vs each independently designate -L-X—Y as defined above.  
 
     
     
         2 . The compound according to  claim 1 , a salt thereof or a hydrate of them, wherein Cy forms a 5-membered heteroaryl group.  
     
     
         3 . The compound according to  claim 1 , a salt thereof or a hydrate of them, wherein Cy forms a thiophene ring.  
     
     
         4 . The compound according to  claim 1 , a salt thereof or a hydrate of them, wherein in the formula (I), the partial structure consisting of Cy and the pyrazole ring adjoining to the Cy is 1H-thieno[2,3-c]pyrazole.  
     
     
         5 . A compound represented by the formula (II), a salt thereof or a hydrate of them.  
       
         
           
           
               
               
           
         
       
       Wherein, 
 Q 1  to Q 4  each independently designate —NV 1 —, —CV 2 ═, —N═, —N(→O)═ or —CO—, and at least one of Q 1  to Q 4  designates —NV 1 — or —N═, —N(→O)═; and  
 R 1  designates a group represented by the formula —(CO) h —(NR a ) j —(CR b ═CR c ) k —Ar (wherein R a , R b  and R c  each independently designate a hydrogen atom, halogen atom, hydroxyl group, an optionally substituted C 1-6  alkyl group, an optionally substituted C 2-6  alkenyl group, an optionally substituted C 1-6  alkoxy group, an optionally substituted C 2-6  alkenyloxy group, an optionally substituted C 1-6  alkylthio group, an optionally substituted C 2-6  alkenylthio group, an optionally substituted C 3-8  cycloalkenyl group, an optionally substituted 4- to 14-membered non-aromatic heterocyclic group, an optionally substituted C 6-14  aryl group or an optionally substituted 5- to 14-membered heteroaryl group; Ar designates an optionally substituted C 6-14  aryl group or an optionally substituted 5- to 14-membered heteroaryl group; and h, j and k each independently designate 0 or 1),  
 V 1  and V 2  each independently designate a group represented by the formula -L-X—Y (wherein, L designates a single bond, an optionally substituted C 1-6  alkylene group, an optionally substituted C 2-6  alkenylene group or an optionally substituted C 2-6  alkynylene group;  
 X designates a single bond, or a group represented by —NR 7 —, —O—, —CO—, —S—, —SO—, —SO 2 —, —CO—NR 8 -Z-, —C(O)O—, —NR 8 —CO-Z-, —NR 8 —C(O)O—, —NR 8 —S—, —NR 8 —SO—, —NR 8 —SO 2 -Z-, —NR 9 —CO—NR 10 —, —NR 9 —CS—NR 10 —, —S(O) m —NR 11 -Z-, —C(═NR 12 )—NR 13 —, —OC(O)—, —OC(O)—NR 14 — or —CH 2 —NR 8 —COR 7 — (wherein R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13  and R 14  each independently designate a hydrogen atom, halogen atom, hydroxyl group, an optionally substituted C 1-6  alkyl group, an optionally substituted C 2-6  alkenyl group, an optionally substituted C 2-6  alkynyl group, an optionally substituted C 1-6  alkoxy group, an optionally substituted C 2-6  alkenyloxy group, an optionally substituted C 1-6  alkylthio group, an optionally substituted C 2-6  alkenylthio group, an optionally substituted C 3-8 cycloalkyl group, an optionally substituted C 3-8 cycloalkenyl group, an optionally substituted 4- to 14-membered non-aromatic heterocyclic group, an optionally substituted C 6-14  aryl group or an optionally substituted 5- to 14-membered heteroaryl group, Z designates a single bond or an optionally substituted C 1-6  alkylene group, and m designates 0, 1 or 2); and  
 Y designates any one group selected from the group consisting of a hydrogen atom, halogen atom, nitro group, hydroxyl group, cyano group, carboxyl group or an optionally substituted C 1-6  alkyl group, an optionally substituted C 2-6  alkenyl group, an optionally substituted C 2-6  alkynyl group, an optionally substituted C 1-6  alkoxy group, an optionally substituted C 3-8  cycloalkyl group, an optionally substituted C 3-8  cycloalkenyl group, an optionally substituted 4- to 14-membered non-aromatic heterocyclic group, an optionally substituted C 6-14  aryl group, an optionally substituted 5- to 14-membered heteroaryl group, an optionally substituted amino group and a group represented by the formula —W—R 15  (wherein W designates CO or SO 2 ; and R 15  designates an optionally substituted C 1-6  alkyl group, an optionally substituted amino group, an optionally substituted C 6-14  aryl group or an optionally substituted 5- to 14-membered heteroaryl group).  
 
     
     
         6 . The compound according to  claim 5 , a salt thereof or a hydrate of them, wherein among Q 1  to Q 4 , either one is —N═, and the others are —CV 2 ═.  
     
     
         7 . The compound according to  claim 5 , a salt thereof or a hydrate of them, wherein among Q 1  to Q 4 , either one of Q 1 , Q 3  and Q 4  is —N═, and the others are —CV 2 ═.  
     
     
         8 . The compound according to  claim 6 , a salt thereof or a hydrate of them, wherein Q 1  is —N═.  
     
     
         9 . The compound according to  claim 6 , a salt thereof or a hydrate of them, wherein Q 2  is —N═.  
     
     
         10 . The compound according to  claim 6 , a salt thereof or a hydrate of them, wherein Q 3  is —N═.  
     
     
         11 . The compound according to  claim 6 , a salt thereof or a hydrate of them, wherein Q 4  is —N═.  
     
     
         12 . The compound according to  claim 5 , a salt thereof or a hydrate of them, wherein among Q 1  to Q 4 , either two are —N═, and the others are —CV 2 ═.  
     
     
         13 . The compound according to  claim 12 , a salt thereof or a hydrate of them, wherein among Q 1  to Q 4 , either two of Q 1 , Q 3  and Q 4  are —N═, and the others are —CV 2 ═.  
     
     
         14 . The compound according to any one of  claims 5  to  13 , a salt thereof or a hydrate of them, wherein when either of Q 1 , Q 3  and Q 4  is —CV 2 ═, the —CV 2 ═ in Q 1 , Q 3  or Q 4  is —CH═.  
     
     
         15 . The compound according to  claim 5 , a salt thereof or a hydrate of them, wherein among Q 1  to Q 4 , either three are —N═, and the other is —CV 2 ═.  
     
     
         16 . The compound according to  claim 15 , a salt thereof or a hydrate of them, wherein Q 1 , Q 3  and Q 4  are —N═.  
     
     
         17 . The compound according to  claim 5 , a salt thereof or a hydrate of them, wherein among Q 1  to Q 4 , at least one is —CO—.  
     
     
         18 . The compound according to  claim 5 , a slat thereof or a hydrate of them, wherein Q 1  is —CO—, Q 2  is —NV 1 —, and Q 3  and Q 4  are —CV 2 ═.  
     
     
         19 . The compound according to  claim 5 , a slat thereof or a hydrate of them, wherein Q 3  is —CO—, Q 2  is —NV 1 —, and Q 1  and Q 4  are —CV 2 ═.  
     
     
         20 . A compound represented by the formula (III), a salt thereof or a hydrate of them.  
       
         
           
           
               
               
           
         
       
       Wherein 
 R 1  designates a group represented by the formula —(CO) h —(NR a ) j —(CR b ═CR c ) k —Ar (wherein R a , R b  and R c  each independently designate a hydrogen atom, halogen atom, hydroxyl group, an optionally substituted C 1-6  alkyl group, an optionally substituted C 2-6  alkenyl group, an optionally substituted C 1-6  alkoxy group, an optionally substituted C 2-6  alkenyloxy group, an optionally substituted C 1-6  alkylthio group, an optionally substituted C 2-6  alkenylthio group, an optionally substituted C 3-8  cycloalkenyl group, an optionally substituted 4- to 14-membered non-aromatic heterocyclic group, an optionally substituted C 6-14  aryl group or an optionally substituted 5- to 14-membered heteroaryl group; Ar designates an optionally substituted C 6-14  aryl group or an optionally substituted 5- to 14-membered heteroaryl group; and h, j and k each independently designate 0 or 1, provided that when h and j are 0, k is 1);  
 R d , R e  and R f  each independently designate a hydrogen atom, halogen atom, hydroxyl group, cyano group, nitro group, carboxyl group, an optionally substituted C 1-6  alkyl group, an optionally substituted C 1-6  alkoxy group, an optionally substituted C 2-7  acyl group, —CO—NR 2a R 2a , —NR 2b CO—R 2a  or —NR 2a R 2b  (wherein R 2a  and R 2b  each independently designate a hydrogen atom or an optionally substituted C 1-6  alkyl group);  
 L designates a single bond, an optionally substituted C 1-6  alkylene group, an optionally substituted C 2-6  alkenylene group or an optionally substituted C 2-6  alkynylene group;  
 X designates a single bond, or a group represented by —NR 7 —, —O—, —CO—, —S—, —SO—, —SO 2 —, —CO—NR 8 -Z-, —C(O)O—, —NR 8 —CO-Z-, —NR 8 —C(O)O—, —NR 8 —S—, —NR 8 —SO—, —NR 8 —SO 2 -Z-, —NR 9 —CO—NR 10 —, —NR 9 —CS—NR 10 —, —S(O)—NR 11 -Z-, —C(═NR 12 )—NR 13 —, —OC(O)—, —OC(O)—NR 14 — or —CH 2 —NR 8 —COR 7 — (wherein R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13  and R 14  each independently designate a hydrogen atom, halogen atom, hydroxyl group, an optionally substituted C 1-6  alkyl group, an optionally substituted C 2-6  alkenyl group, an optionally substituted C 2-6  alkynyl group, an optionally substituted C 1-6  alkoxy group, an optionally substituted C 2-6  alkenyloxy group, an optionally substituted C 1-6  alkylthio group, an optionally substituted C 2-6  alkenylthio group, an optionally substituted C 3-8 cycloalkyl group, an optionally substituted C 3-8 cycloalkenyl group, an optionally substituted 4- to 14-membered non-aromatic heterocyclic group, an optionally substituted C 6-14  aryl group or an optionally substituted 5- to 14-membered heteroaryl group, Z designates a single bond or an optionally substituted C 1-6  alkylene group, and m designates 0, 1 or 2); and  
 Y designates any one group selected from the group consisting of a hydrogen atom, halogen atom, nitro group, hydroxyl group, cyano group, carboxyl group or an optionally substituted C 1-6  alkyl group, an optionally substituted C 2-6  alkenyl group, an optionally substituted C 2-6  alkynyl group, an optionally substituted C 1-6  alkoxy group, an optionally substituted C 3-8  cycloalkyl group, an optionally substituted C 3-8  cycloalkenyl group, an optionally substituted 4- to 14-membered non-aromatic heterocyclic group, an optionally substituted C 6-14  aryl group, an optionally substituted 5- to 14-membered heteroaryl group, an optionally substituted amino group and a group represented by the formula —W—R 15  (wherein W designates CO or SO 2 ; and R 15  designates an optionally substituted C 1-6  alkyl group, an optionally substituted amino group, an optionally substituted C 6-14  aryl group or an optionally substituted 5- to 14-membered heteroaryl group).  
 
     
     
         21 . The compound according to  claim 20 , a salt thereof or a hydrate of them, wherein at least one of R d , R e  and R f  is not a hydrogen atom.  
     
     
         22 . The compound according to  claim 20 , a salt threof or a hydrate of them, wherein either one of R d , R e  and R f  is a halogen atom or an optionally substituted C 1-6  alkoxy group.  
     
     
         23 . The compound according to any one of  claims 20  to  22 , a salt thereof or a hydrate of them, wherein at least one of R b  and R c  is not a hydrogen atom, and L is a single bond, an optionally substituted C 2-6  alkenylene group or an optionally substituted C 2-6  alkynylene group, provided that, when L is a single bond, the case where X is a single bond, and Y is an optionally substituted C 1-6  alkyl group, an optionally substituted C 3-8  cycloalkyl group, an optionally substituted C 3-8  cycloalkenyl group, an optionally substituted 4- to 14-membered non-aromatic heterocyclic group, an optionally substituted C 6-14  aryl group or an optionally substituted 5- to 14-membered heteroaryl group is excluded.  
     
     
         24 . The compound according to any one of  claims 1  to  22 , a salt thereof or a hydrate of them, wherein at least either h or j is 1.  
     
     
         25 . The compound according to any one of  claims 1  to  22 , a salt thereof or a hydrate of them, wherein h and j are 0, and k is 1.  
     
     
         26 . The compound according to any one of  claims 1  to  19 , a salt thereof or a hydrate of them, wherein h, j and k are 0.  
     
     
         27 . The compound according to any one of claims  24  and  25 , a salt thereof or a hydrate of them, wherein R b  and/or R c  are(is) a hydrogen atom.  
     
     
         28 . The compound according to  claim 27 , a salt thereof or a hydrate of them, wherein R b  and R c  are a hydrogen atom.  
     
     
         29 . The compound according to any one of  claims 1  to  28 , a salt thereof or a hydrate of them, wherein Ar is a C 6-14  aryl group or a 5- to 14-membered heteroaryl group, and Ar is a group which may be substituted with 1 to 3 group(s) selected from the following substituent group (a):  
       <Substituent group a> the group consisting of (1) each optionally substituted (a) C 1-6  alkyl groups, (b) C 1-6  alkoxy groups, (c) C 1-7  acyl groups, (d) amide group, (e) amino group, (f) C 3-8  cycloalkyl groups, (2) halogen atom, (3) hydroxyl group, (4) nitro group, (5) cyano group, and (6) carboxyl group.  
     
     
         30 . The compound according to  claim 29 , a salt thereof or a hydrate of them, wherein Ar is a phenyl group, naphthyl group or a 5- to 10-membered heteroaryl group, and Ar is a group optionally substituted with 1 to 3 group(s) selected from Substituent group A described in  claim 29 .  
     
     
         31 . The compound according to  claim 29 , a salt thereof or a hydrate of them, wherein Ar is a phenyl group, 2-naphthyl group, pyridyl group, 2-thienyl group, 2-furyl group, 2-benzofuryl group, 2-quinolyl group or 2-benzothienyl group, and Ar is a group optionally substituted with 1 to 3 group(s) selected from Substituent group A described in  claim 29 .  
     
     
         32 . The compound according to  claim 29 , a salt thereof or a hydrate of them, wherein Ar is a phenyl group, pyridyl group, 2-thienyl group or 2-furyl group, and Ar is a group optionally substituted with 1 to 3 group(s) selected from Substituent group A described in  claim 29 .  
     
     
         33 . The compound according to  claim 29 , a salt thereof or a hydrate of them, wherein Ar is a 2-naphthyl group, 2-benzofuryl group, 2-quinolyl group or 2-benzothienyl group, and Ar is a group optionally substituted with 1 to 3 group(s) selected from Substituent group a described in  claim 29 .  
     
     
         34 . The compound according to any one of  claims 29  to  33 , a salt thereof or a hydrate of them, wherein Substituent group A is the group consisting of (1) C 1-6  alkyl groups each optionally substituted with 1 to 3 group(s) selected from the group consisting of a halogen atom, hydroxyl group and cyano group, (2) C 1-6  alkoxy groups optionally substituted with 1 to 3 group(s) selected from the group consisting of a halogen atom, hydroxyl group and cyano group, (3) halogen atom, (4) hydroxyl group, (5) cyano group, and (6) C 1-7  acyl groups.  
     
     
         35 . The compound according to any one of  claims 29  to  33 , a salt thereof or a hydrate of them, wherein Substituent group A is a halogen atom.  
     
     
         36 . The compound according to any one of  claims 1  to  35 , a salt thereof or a hydrate of them, wherein L is a single bond or methylene group.  
     
     
         37 . The compound according to  claim 36 , a salt thereof or a hydrate of them, wherein L is a single bond.  
     
     
         38 . The compound according to any one of  claims 1  to  37 , a salt thereof or a hydrate of them, wherein X is a group represented by —CO—NR 8 -Z-, —NR 8 —CO-Z- or —NR 8 —SO 2 -Z- (wherein R 8  and Z have the same meanings as defined for R 8  and Z in  claim 1) .  
     
     
         39 . The compound according to  claim 38 , a salt thereof or a hydrate of them, wherein R 8  is a hydrogen atom.  
     
     
         40 . The compound according to  claim 38 , a salt thereof or a hydrate of them, wherein X is a group represented by —CO—NH—(CH 2 ) t — (wherein t designates 0 or 1).  
     
     
         41 . The compound according to  claim 38 , a salt thereof or a hydrate of them, wherein X is a group represented by —NH—CO—(CH 2 ) t — (wherein t designates 0 or 1).  
     
     
         42 . The compound according to any one of  claims 1  to  37 , a salt thereof or a hydrate of them, wherein X is a single bond.  
     
     
         43 . The compound according to any one of  claims 1  to  42 , a salt thereof or a hydrate of them, wherein Y is a C 1-6  alkyl group, a C 6-14  aryl group, a C 1-6  alkoxy group, a C 3-8  cycloalkyl group, a 4- to 14-membered non-aromatic heterocyclic group or a 5- to 14-membered heteroaryl group, and Y is a group optionally substituted with 1 to 3 group(s) selected from the following Substituent group a2:  
       <Substituent group a2> the group consisting of (1) each optionally substituted (a) C 1-6  alkyl groups, (b) C 2-6  alkenyl groups, (c) C 2-6  alkynyl groups, (d) C 1-6  alkoxy groups, (e) C 2-7  acyl groups, (f) amide group, (g) amino group, (h) C 3-8 cycloalkyl groups, (i) C 3-8  cycloalkenyl groups, (j) C 6-14  aryl groups, (k)  5 - to 14-membered heteroaryl groups, (1) C 6-14  aryloxy groups, and (m) 4- to 14-membered non-aromatic heterocyclic groups, (2) halogen atom, (3) hydroxyl group, (4) nitro group, (5) cyano group, and (6) carboxyl group.  
     
     
         44 . The compound according to  claim 43 , a salt thereof or a hydrate of them, wherein Y is a C 3-8  cycloalkyl group, phenyl group, a 5- or 6-membered non-aromatic heterocyclic group, or a 5- or 6-membered heteroaryl group, and Y is a group optionally substituted with 1 to 3 group(s) selected from Substituent group a2 described in  claim 43 .  
     
     
         45 . The compound according to any one of  claims 1  to  42 , a salt thereof or a hydrate of them, wherein Y is a furyl group, thienyl group, pyrrolyl group, phenyl group, pyridyl group, C 3-8  cycloalkyl group, tetrahydrofuran-yl group, tetrahydrothiophene-yl group, pyrrolidinyl group, tetrahydrofuran-2-on-yl group, pyrrolidine-2-on-yl group or a group represented by the formula:  
       
         
           
           
               
               
           
         
       
       (wherein Y 2a  designates a group represented by —CONH 2  or —CH 2 OH, Y 2b  and Y 2c  each independently designate a hydrogen atom, an optionally substituted phenyl group or an optionally substituted C 1-6  alkyl group), and Y is a group optionally substituted with 1 to 3 group(s) selected from Substituent group a2 described in  claim 43 .  
     
     
         46 . The compound according to  claim 43 , a salt thereof or a hydrate of them, wherein Y is a furyl group or thienyl group, and Y is a group optionally substituted with 1 to 3 group(s) selected from Substituent group a2 described in  claim 43 .  
     
     
         47 . The compound according to any one of  claims 43  to  46 , a salt thereof or a hydrate of them, wherein Substituent group a2 is the group consisting of (1) (a) C 1-6  alkyl groups, (b) C 1-6  alkoxy groups, (C)C 1-7  acyl groups, (d) amide group, (e) amino group, (f) C 3-8 cycloalkyl groups, each of which may be substituted with 1 to 3 group(s) selected from the following Substituent group b2, (2) halogen atom, (3) hydroxyl group, (4) nitro group, (5) cyano group, and (6) carboxyl group, and <Substituent group b2> is the group consisting of C 1-6  alkyl groups, halogen atom, hydroxyl group, nitro group, cyano group and carboxyl group.  
     
     
         48 . The compound according to any one of  claims 43  to  46 , a salt thereof or a hydrate of them, wherein Substituent group a2 is the group consisting of (1) C 1-6  alkoxy groups, (2) halogen atoms and (3) cyano groups.  
     
     
         49 . The compound according to any one of  claims 20  to  35 , a salt thereof or a hydrate of them, wherein L and X are a single bond, Y is a 5- to 6-membered heteroaryl group, and Y is a group optionally substituted with 1 to 3 group(s) selected from Substituent group a2 described in  claim 43 .  
     
     
         50 . A pharmaceutical composition comprising the compound according to anyone of  claims 1  to  49 , a salt thereof or a hydrate of them, and a pharmaceutically acceptable carrier.  
     
     
         51 . A c-Jun amino-terminal kinase (JNKs) inhibitor comprising the compound according to any one of  claims 1  to  49 , a salt thereof or a hydrate of them.  
     
     
         52 . A c-Jun amino-terminal kinase 1 (JNK 1), c-Jun amino-terminal kinase 2 (JNK 2) and/or c-Jun amino-terminal kinase 3 (JNK 3) inhibitor, comprising the compound according to any one of  claims 1  to  49 , a salt thereof or a hydrate of them.  
     
     
         53 . An agent for treating or preventing immunological diseases, inflammatory diseases or metabolic disorders, which comprises the compound according to any one of  claims 1  to  49 , a salt thereof or a hydrate of them.  
     
     
         54 . An agent for treating or preventing neurodegenerative diseases, which comprises the compound according to any one of  claims 1  to  49 , a salt thereof or a hydrate of them.  
     
     
         55 . An agent for treating or preventing Alzheimer's disease, Parkinson's disease, Huntington's chorea, amyotrophic lateral sclerosis, multiple sclerosis or spinocerebellar degeneration, which comprises the compound according to any one of  claims 1  to  49 , a salt thereof or a hydrate of them.  
     
     
         56 . Use of the compound according to any one of  claims 1  to  49 , a salt thereof or a hydrate of them for prevention or treatment of immunological diseases, inflammatory diseases, metabolic disorders and/or neurodegenerative diseases.  
     
     
         57 . Use of the compound according to any one of  claims 1  to  49 , a salt thereof or a hydrate of them, for producing an agent for treating or preventing a disease based on JNK action against which inhibition of a c-Jun amino-terminal kinase (JNK) is effective for prevention or treatment, immunological diseases, inflammatory diseases, metablic disorders or neurodegenerative diseases.  
     
     
         58 . The use according to  claim 57 , wherein the disease is Alzheimer's disease, Parkinson's disease, Huntington's chorea, amyotrophic lateral sclerosis, multiple sclerosis or spinocerebellar degeneration.  
     
     
         59 . A method for treating or preventing a disease based on JNK 3 action against which inhibition of a c-Jun amino-terminal kinase 3 (JNK 3) is effective for prevention or treatment, immunological diseases, inflammatory diseases, metablic disorders and/or neurodegenerative diseases, which comprises adiministering a pharmacologically effective amount of the compound according to any one of  claims 1  to  49 , a salt thereof or a hydrate of them to a patient.  
     
     
         60 . A method for treating or preventing a disease based on JNK action against which inhibition of a c-Jun amino-terminal kinase (JNK) is effective for prevention or treatment, immunological diseases, inflammatory diseases, metablic disorders or neurodegenerative diseases, which comprises adiministering a pharmacologically effective amount of the compound according to any one of  claims 1  to  49 , a salt thereof or a hydrate of them to a patient.  
     
     
         61 . The method according to  claim 60 , wherein the disease is Alzheimer's disease, Parkinson's disease, Huntington's chorea, amyotrophic lateral sclerosis, multiple sclerosis or spinocerebellar degeneration.

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