Amine-based compound and use thereof

Abstract

Novel amine compounds which are represented by the following formula (1) and efficacious against diseases such as a viral infectious disease with HIV, rheumatism, and cancer metastasis; typically, A 1 and A 2 represent a hydrogen atom or a substitutable monocyclic or polycyclic heteroaromatic ring and W represents a substitutable benzene ring or any group represented by the following formula (10) or (11): where X represents O, CH 2 , C(═O), NR 11 , or CHR 35 and D represents a group represented by the following formula (6): [Formula 4] -Q-Y—B  (6) where Q represents a single bond, NR 12 , or a group represented by the formula (13): and Y represents a group represented by the following formula (7): [Formula 6] —(CR 18 R 19 ) m 3 - or —(CR 20 R 21 ) m 4 - z -(CR 22 R 23 ) m 5 -  (7) where z represents a substitutable monocyclic or polycyclic aromatic ring; and B represents —NR 25 R 26 ; and R 1 to R 26 in the above formulae represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group.

1 . A compound represented by the following general formula (1) or a pharmacologically acceptable salt thereof, or a prodrug thereof: 
       
         
           
           
               
               
           
         
       
       wherein 
       n 1 , n 2 , and n 3  represent an integer of 0 to 3;
 R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  each independently represent a hydrogen atom, a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms, a substitutable alkynyl group having 2 to 15 carbon atoms, or a substitutable cyclic alkyl group having 3 to 15 carbon atoms where R 5  and R 6  each may form a carbonyl group with a carbon atom bound thereto; and 
 A 1  and A 2  each independently represent a hydrogen atom, a substitutable monocyclic or polycyclic heteroaromatic ring, a partly saturated substitutable polycyclic heteroaromatic ring, a substitutable monocyclic or polycyclic aromatic ring, a partially saturated substitutable polycyclic aromatic ring, a substitutable heteroring, or a group represented by the following formula (2): 
 
       
         
           
           
               
               
           
         
       
       wherein
 R 7 , R 8 , R 9 , and R 10  each independently represent a hydrogen atom, a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms, a substitutable alkynyl group having 2 to 15 carbon atoms, or a substitutable cyclic alkyl group having 3 to 15 carbon atoms; 
 W represents any one of a substitutable benzene ring and groups represented by the following formulae (10) and (11): 
 
       
         
           
           
               
               
           
         
       
       wherein
 R 30  represents a hydrogen atom, a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms, a substitutable alkynyl group having 2 to 15 carbon atoms, a substitutable cyclic alkyl group having 3 to 15 carbon atoms, a methanesulfonyl group, a p-toluenesulfonyl group, a phenyl group, an acyl group, a carboxyl group, or a cyano group; 
 m 7  represents an integer of 0 to 2; 
 T 1  and T 2  represent CH 2  or CO; 
 T 3  and T 4  have a relationship of T 3 =NH and T 4 =CO, or T 3 =CO and T 4 =NH; 
 X represents a substitutable monocyclic or polycyclic heteroaromatic ring, a substitutable monocyclic or polycyclic aromatic ring, O, CH 2 , NR 11 , CHR 35 , or a group represented by the following formula (3) or (12); 
 R 11  represents a hydrogen atom, a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms, a substitutable alkynyl group having 2 to 15 carbon atoms, or a substitutable cyclic alkyl group having 3 to 15 carbon atoms; 
 R 35  represents a carboxyl group or an alkoxycarbonyl group: 
 
       
         
           
           
               
               
           
         
       
       wherein
 m 1  represents an integer of 1 or 2: 
 
       
         
           
           
               
               
           
         
       
       wherein
 T 5  represents an oxygen atom or a sulfur atom; 
 R 31  and R 32  represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 31  and R 32  may be coupled to each other to form a ring; 
 D represents a group represented by the following formula (4) or (6): 
 
       
         
           
           
               
               
           
         
       
       wherein
 R 13  represents a hydrogen atom, a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms, a substitutable alkynyl group having 2 to 15 carbon atoms, a substitutable cyclic alkyl group having 3 to 15 carbon atoms, or a group represented by the following formula (5): 
 
       
         
           
           
               
               
           
         
       
       wherein
 m 2  represents an integer of 2 to 4; 
 R 14 , R 15 , R 16 , and R 17  each independently represent a hydrogen atom, a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms, a substitutable alkynyl group having 2 to 15 carbon atoms, or a substitutable cyclic alkyl group having 3 to 15 carbon atoms:
   [Formula 9] 
   -Q-Y—B  (6)
 
 
 
       wherein
 Q represents a single bond when X is O, a single bond or a group represented by the formula (3) when X is NR 11 , or a single bond, S, O, or NR 12 , or a group represented by the formula (13) when X is a substitutable monocyclic or polycyclic heteroaromatic ring, a substitutable monocyclic or polycyclic aromatic ring, CH 2  or is represented by the formula (3) or (12): 
 
       
         
           
           
               
               
           
         
         R 12  represents a hydrogen atom, a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms, a substitutable alkynyl group having 2 to 15 carbon atoms, a substitutable cyclic alkyl group having 3 to 15 carbon atoms, a methanesulfonyl group, a p-toluenesulfonyl group, a phenyl group, an acyl group, a carboxyl group, a cyano group, or a group represented by the formula (15): 
       
       
         
           
           
               
               
           
         
         R 34  represents a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable cyclic alkyl group having 3 to 15 carbon atoms, or a phenyl group; 
         Y represents a group represented by the following formula (7):
   [Formula 12] 
   —(CR 18 R 19 ) m   3 -
 
   or 
   —(CR 20 R 21 ) m   4 - z -(CR 22 R 23 ) m   5 -  (7)
 
 
       
       wherein
 m 3  represents an integer of 0 to 6; 
 R 18  and R 19  each independently represent a hydrogen atom, a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms, a substitutable alkynyl group having 2 to 15 carbon atoms, a substitutable cyclic alkyl group having 3 to 15 carbon atoms, or a substitutable aromatic ring, and R 12  and R 18  may form a ring; 
 m 4  and m 5  represent an integer of 0 to 2; 
 R 20 , R 21 , R 22 , and R 23  each independently represent a hydrogen atom, a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms, a substitutable alkynyl group having 2 to 15 carbon atoms, or a substitutable cyclic alkyl group having 3 to 15 carbon atoms; 
 z represents a substitutable cyclic alkylene group having 3 to 15 carbon atoms, a substitutable monocyclic or polycyclic heteroaromatic ring, a partly saturated substitutable polycyclic heteroaromatic ring, a substitutable monocyclic or polycyclic aromatic ring, a partly saturated substitutable polycyclic aromatic ring, a substitutable heterocycle, S, O, NR 12 , S═O, O═S═O, or the formula (16): 
 
       
         
           
           
               
               
           
         
         B represents any one of the groups represented by the following formulae (8) and (14): 
       
       
         
           
           
               
               
           
         
       
       wherein
 Q 1  represents S, O, or NH and Q 2  represents S, O, or NR 27 ; 
 R 24  and R 27  each independently represent a hydrogen atom, a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms, a substitutable alkynyl group having 2 to 15 carbon atoms, a substitutable cyclic alkyl group having 3 to 15 carbon atoms, or a substitutable aromatic ring, and R 24  and R 27  may form a ring; 
 R 25  and R 26 , when above X is CH 2 , each independently represent a hydrogen atom, a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable cyclic alkyl group having 3 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms and having 1 to 3 double bonds, or a substitutable alkynyl group having 2 to 15 carbon atoms and having 1 to 3 triple bonds, and R 25  and R 26  may form a ring and, depending on circumstances, the ring may be formed by binding through a heteroatom, a cyclic alkyl group, an aromatic ring, a heteroaromatic ring, or a heterocycle; 
 R 25  and R 26 , when above X is not CH 2 , each independently represent a hydrogen atom, a substituent represented by the following formula (9), a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable cyclic alkyl group having 3 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms and having 1 to 3 double bonds, or a substitutable alkynyl group having 2 to 15 carbon atoms and having 1 to 3 triple bonds, and R 25  and R 26  may form a ring and, depending on circumstances, the ring may be formed by binding through a heteroatom, a cyclic alkyl group, an aromatic ring, a heteroaromatic ring, or a heterocycle: 
 
       
         
           
           
               
               
           
         
       
       wherein
 m 6  represents 0 or 1, where when m 6 =0, Q 3  represents CH or N and Q 4  represents N, S, or O, and when m 6 =1, Q3 and Q4 each G represents a substitutable alkylene group having 1 to 15 carbon atoms or a substitutable alkenylene group having 2 to 15 carbon atoms; 
 R 28  represents an alkyl group having 1 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms, a substitutable alkynyl group having 2 to 15 carbon atoms, an alkoxy group, a haloalkyl group, a haloalkoxy group, a hydroxyalkoxy group, a halogen atom, an amino group, an alkylamino group, a carboxyl group, an alkoxycarbonyl group, a carbamoyl group, an alkylcarbamoyl group, a saturated heterocycle, or a heteroaromatic ring, which is substituted at any position except a nitrogen atom which may be present on the ring or may represent a hydrogen atom when m 6 =1 and Q 3  and Q 2  simultaneously represent CH; 
 R 29  represents a hydrogen atom or the same group as R 24 , and may be coupled with G to form a ring: 
 
       
         
           
           
               
               
           
         
       
       wherein
 R 33  represents the same group as that of above R 12 , 
 
       wherein one or two or more asymmetric carbon atoms may exist in the compound represented by the general formula (1), where when one asymmetric carbon atom exists, the compound may be in the form of any one of a pure optically-active substance represented by the absolute configuration R or S, a mixture thereof in a predetermined ratio, and a racemic mixture thereof or when two or more asymmetric carbon atoms exist, the compound may be in the form of any one of an optically pure diastereomer, a racemic mixture thereof, and a combination thereof in a predetermined ratio. 
     
     
         2 . A compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 , wherein n 1 , n 2 , and n 3  represent an integer of 1 and R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  represent a hydrogen atom. 
     
     
         3 . A compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 , wherein A 1  and A 2  each independently represent a hydrogen atom or a substitutable monocyclic or polycyclic heteroaromatic ring. 
     
     
         4 . A compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 , wherein W represents a group represented by the formula (10). 
     
     
         5 . A compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 , wherein W represents a benzene ring and X represents a group represented by the formula (12). 
     
     
         6 . A compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 , wherein W represents a benzene ring, X represents —CH 2 —, and D represents a group represented by the formula (6) where Q represents a group represented by NR 12  and R 12  is based on the same definition as described above. 
     
     
         7 . A compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 ,
 wherein D represents a group represented by the formula (6), in the formula   Q represents NR 12  where R 12  is based on the same definition as described above; and   Y represents a group represented by —(CR 18 R 19 )m 3 - where R 18 , R 19 , and m 3  are based on the same definition as described above.   
     
     
         8 . A compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 , wherein:
 D represents a group represented by the formula (6), in the formula Q represents any one of the groups represented by the formula (13) where R 12  is based on the same definition as described above; and   Y represents a group represented by —(CR 18 R 19 )m 3 - where R 18 , R 19 , and m 3  are based on the same definition as described above.   
     
     
         9 . A compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 , wherein D represents a group represented by the formula (6) where B represents —NR 25 R 26  where R 25  and R 26  are based on the same definition as described above. 
     
     
         10 . A compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 , wherein D represents a group represented by the formula (6) where B represents any one of the groups represented by the formula (14). 
     
     
         11 . A compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1  which is selected from the group consisting of:
 2-[(4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-ethanol; 
 [4-(6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1H-benzimidazol-2-yl)-butyl]-dipropyl-amine: 
 [4-(6-{[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl}-1-propyl-1H-benzimidazol-2-yl)-butyl]-dipropyl-amine; 
 [4-(6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1-propyl-1H-benzimidazol-2-yl)-butyl]-dipropyl-amine; 
 [4-(5-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1-propyl-1H-benzimidazol-2-yl)-butyl]-dipropyl-amine; 
 4-{[N-(1H-imidazol-2-ylmethyl)-amino]-methyl-N-(4-dipropylamino-butyl)-benzamide; 
 2-(4-dipropylamino-butyl)-5-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-2,3-dihydro-isoindol-1-one; 
 2-(4-dipropylamino-butyl)-6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-2,3-dihydro-isoindol-1-one; 
 N-(4-{[(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-N-methyl-N′,N′-dipropyl-butane-1,4-diamine; 
 N-methyl-N-[4-({[1-(1-methyl-1H-imidazol-2-ylmethyl)-1H-imidazol-2-ylmethyl]-amino}-methyl)-benzyl-N′,N′-dipropylbutane-1,4-diamine; 
 [4-(6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1H-inden-2-yl)-butyl]-dipropyl-amine; 
 1-(4-dipropylaminobutyl)-3-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-urea; 
 [4-(6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1-methyl-1H-benzimidazol-2-yl)-butyl]-dipropyl-amine; 
 3-(3-dipropylaminopropyl)-8-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-3,4-dihydro-1H-benzo[e][1,4]diazepin-2,5-dione; 
 4-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethyl-phenyl)-benzamide; 
 4-{[(5-ethyl-pyridin-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethyl-phenyl)-benzamide; 
 [4-(6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-3,4-dihydro-1H-isoquinolin-2-yl)-butyl]-dipropyl-amine; 
 [3-(6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1-methyl-1H-benzimidazol-2-yl)-benzyl]-dipropyl-amine; 
 6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amide; 
 N-(4-dipropylamino-butyl)-4-{[(1-methyl-1H-imidazol-2-ylmethyl)-(5-methyl-pyridin-2-ylmethyl)-amino]-methyl}-benzamide; 
 N-(4-dipropylamino-butyl)-N-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-methanesulfonamide; 
 N-(4-dipropylamino-butyl)-N-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-4-methyl-benzenesulfonamide; 
 N-ethyl-N-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-N′,N′-dipropyl-butane-1,4-diamine; 
 N-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-N-phenyl-N′,N′-dipropyl-butane-1,4-diamine; 
 N-(4-dipropylamino-butyl)-N-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-acetamide; 
 1-(4-dipropylamino-butyl)-3-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-1-methyl-urea; 
 1-(4-dipropylamino-butyl)-3-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-1,3-dimethyl-urea; 
 N-methyl-N-[4-({(1-methyl-1H-imidazol-2-ylmethyl)-[1-(toluene-4-sulfonyl)-1H-imidazol-2-ylmethyl]-amino}-methyl)-benzyl]-N″,N″-dipropyl-butane-1,4-diamine; 
 [4-(6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1-methyl-1H-benzimidazol-2-yl)-benzyl]-dipropyl-amine; 
 6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-imidazo[1,2-a]pyridine-2-carboxylate-(4-dipropyl)-amino-butyl)-amide; 
 N-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino}-methyl]-benzyl)-N′,N′-dipropyl-N-(2,2,2-trifluoro-ethyl)-butane-1,4-diamine; 
 N-(4-{[(1-methanesulfonyl-1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-N-methyl-N″,N″-dipropyl-butane-1,4-diamine; 
 3-[(4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionitrile; 
 3-[(4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid methyl ester; 
 1-(4-dipropylamino-butyl)-3-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-thiourea; 
 {3-[6-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-pyridin-2-yl]-propyl}-dipropyl-amine; 
 N-(4-dipropylamino-butyl)-2,2,2-trifluoro-N-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-acetamide; 
 [4-(5-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1,3-dihydro-isoindol-2-yl)-butyl]-dipropyl-amine; 
 {4-(1E)-[2-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-vinyl]-benzyl}-dipropyl-amine; 
 {[4-((1Z)-2-{4-[(dipropylamino)-methyl]-phenyl}-vinyl)-phenyl]-methyl}-(imidazol-2-ylmethyl)-[(1-methylimidazol-2-yl)-methyl]-amine; 
 {[4-((1E)-2-{4-[2-(dipropylamino)-ethyl]-phenyl}-vinyl)-phenyl]-methyl}-(imidazol-2-ylmethyl)-[(1-methylimidazol-2-yl)-methyl]-amine; 
 {[4-((1E)-2-{4-[(dipropylamino)-methyl]-phenyl}-vinyl)-phenyl]-methyl}-bis-(imidazol-2-ylmethyl)-amine; 
 [4-(6-{[(1H-imidazol-2-yl-methyl)-(1-methyl-imidazol-2-yl-methyl)-amino]-methyl}-benzothiazol-2-yl)-benzyl]-dipropyl-amine; 
 (4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-methyl-(4-piperidin-1-ylbutyl)amine; 
 2-(2-(4-dipropylamino-butyl)-6-[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl)-benzimidazol-1-yl)-ethanol; 
 [3-(6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1-propyl-1H-benzimidazol-2-yl)-propyl]-dipropyl-amine; 
 [4-(6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1-isopropyl-1H-benzimidazol-2-yl)-butyl]-dipropyl-amine; 
 [5-(6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1-propyl-1H-benzimidazol-2-yl)-pentyl]-dipropyl-amine; 
 N-(4-{[(1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-N-methyl-N′,N′-dipropyl-butane-1,4-diamine; 
 N-(4-dipropylamino-butyl)-N-(4-{[(1H-imidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-methanesulfonamide; 
 3-[(4-dipropylamino-butyl)-(4-[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl)-benzyl)-amino]-propionic acid; 
 (4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-cyanamide; 
 (4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-formamide; 
 [(4-{[(1-carboxymethyl-1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(4-dipropylamino-butyl)amino]-acetic acid; and 
 [4-(1-benzyl-6-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-1H-benzimidazol-2-yl)-butyl]-dipropyl-amine. 
 
     
     
         12 . A compound, a pharmacologically acceptable salt thereof, or a pro-drug thereof according to  claim 1  which is selected from the group consisting of:
 3-[(4-dipropyl amino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid ethyl ester; 
 3-[(4-dipropyl amino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid isopropyl ester; 
 3-[(4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid benzyl ester; 
 3-[(4-dipropyl amino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid butyl ester; 
 3-[(4-dipropyl amino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid-5-methyl-2-oxo-[1,3]-dioxol-4-ylmethyl ester; 
 3-[(4-dipropyl amino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid-1-ethyl-propoxycarbonyloxy methyl ester; 
 3-[(4-dipropyl amino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid-1-(cyclohexyloxycarbonyloxy)-ethyl ester; 
 3-[(4-dipropyl amino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid-methoxycarbonyloxy methyl ester; 
 3-[(4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid-ethoxycarbonyloxy methyl ester; 
 2,2-dimethyl-propionic acid-3-[(4-dipropyl amino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionyloxy methyl ester; 
 3-[(4-dipropyl amino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid-3-oxo-1,3-dihydro-isobenzofuran-1-yl ester; 
 Hexanoic acid-3-[(4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionyloxymethyl ester; 
 3-[(4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid-3-cyclopentyl-propionyloxymethyl ester; 
 3-[(4-dipropyl amino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid-diethylcarbamoyloxy methyl ester; 
 3-[(4-dipropyl amino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-propionic acid t-butoxycarbonyl methyl ester; 
 3-[(4-dipropylamino-butyl)-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-amino]-N-ethyl-propionamide; 
 3-[(4-{[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(4-dipropylamino-butyl)-amino]-propionic acid; 
 3-[(4-{[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(4-dipropylamino-butyl)-amino]-propionate; 
 3-[(4-{[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(4-dipropylamino-butyl)-amino]-propionic acid-5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester; 
 3-[(4-{[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(4-dipropylamino-butyl)-amino]-propionic acid-1-(cyclohexyloxycarbonyloxy)-ethyl ester; 
 2,2-dimethyl-propionic acid-3-[(4-{[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(4-dipropylamino-butyl)-amino]-propionyloxymethyl ester; 
 3-[(4-{[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(4-dipropylamino-butyl)-amino]-propionic acid-3-oxo-1,3-dihydro-isobenzofuran-1-yl ester; 
 3-[(4-{[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(4-dipropylamino-butyl)-amino]-propionic acid-diethylcarbamoyloxy methyl ester; and 
 3-[(4-{[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(4-dipropyl amino-butyl)-amino]-N-ethyl-propionamide. 
 
     
     
         13 . A compound, a pharmacologically acceptable salt thereof, or a pro-drug thereof according to  claim 1  which is selected from the group consisting of:
 (1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-[2-(4-piperidin-1-yl-butyl)-3-propyl-3H-benzimidazol-5-ylmethyl]-amine; 
 3-[(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-(4-piperidin-1-yl-butyl)-amino]-propionic acid; 
 [(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetonitrile; 
 [(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid methyl ester; 
 [(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid; 
 3-[(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-propionic acid-1-isopropoxycarbonyloxy-ethyl ester; 
 3-[(4-[[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-(4-dipropylamino-butyl)-amino]-propionic acid methyl ester; 
 [(4-[[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-(4-dipropylamino-butyl)-amino]-acetic acid methyl ester; 
 [(4-[[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-(4-dipropylamino-butyl)-amino]-acetic acid; 
 [(4-dipropyl amino-butyl)-([[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid benzyl ester; 
 [(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid-2-morpholin-4-yl-ethyl ester; 
 [[4-(dipropyl-amino)-butyl]-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid ethyl ester; 
 [(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid-2-methoxy-ethyl ester; 
 [(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid cinnamyl ester; 
 [(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid-2-(2-hydroxy-ethoxy)-ethyl ester; 
 (4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-carbamic acid t-butyl ester; 
 N-(2-chloro-4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-N-methyl-N′,N′-dipropyl-butane-1,4-diamine; 
 [(4-[[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-(4-dipropylamino-butyl)-amino]-acetic acid ethyl ester; 
 [(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid-3,7,11-trimethyl-dodeca-2,6,10-trienyl ester; 
 2-[(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-N,N-dimethyl-acetamide; 
 [(4-[[bis-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-(4-dipropyl amino-butyl)-amino]-acetic acid; 
 [(4-[[bis-(1-methyl-1-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-(4-dipropyl amino-butyl)-amino]-acetic acid ethyl ester; 
 [(4-dipropylamino-butyl)-([[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid-(R)-(−)-tetrahydrofuran-2-ylmethyl ester; 
 ([4-[(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-methyl-amino]-butyl]-propyl-amino)-acetic acid; 
 ([4-[carboxymethyl-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-butyl]-propyl-amino)-acetic acid; 
 (2-[[(1-carboxymethyl-1H-imidazol-2-ylmethyl)-(4-[[(4-dipropylamino-butyl)-methyl-amino]-methyl]-benzyl)-amino]-methyl]-imidazol-1-yl)-acetic acid; 
 (2-[[(4-[[(4-dipropylamino-butyl)-methyl-amino]-methyl]-benzyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-imidazol-1-yl)-acetic acid; 
 4-[[(4-dipropylamino-butyl)-methyl-amino]-methyl]-N-(1H-imidazol-2-ylmethyl)-N-(1-methyl-1H-imidazol-2-ylmethyl)-benzamide; and 
 2-[(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-malonic acid diethyl ester. 
 
     
     
         14 . A compound, a pharmacologically acceptable salt thereof, or a pro-drug thereof according to  claim 1  which is selected from the group consisting of:
 (2-{2-[(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-methyl-amino]-ethoxy}-ethyl)-dipropyl-amine; 
 N-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-N′,N′-dipropyl-N-(1H-tetrazol-5-ylmethyl)-butane-1,4-diamine; 
 5-dipropylamino-(2S)-[(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-methyl-amino]-pentanoic acid ethyl ester; 
 5-dipropylamino-(2S)-[(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-methyl-amino]-pentanoic acid; 
 (2S)-dipropylamino-5-[(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-methyl-amino]-pentanoic acid ethyl ester; 
 (2S)-dipropylamino-5-[(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-methyl-amino]-pentanoic acid; 
 5-dipropylamino-(2R)-[(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-methyl-amino]-pentanoic acid ethyl ester; 
 5-dipropylamino-(2R)-[(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-methyl-amino]-pentanoic acid; 
 (2R)-dipropylamino-5-[(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-methyl-amino]-pentanoic acid ethyl ester; 
 (2R)-dipropylamino-5-[(4-[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl)-benzyl)-methyl-amino]-pentanoic acid; 
 [(4-dipropylamino-butyl)-methyl-amino]-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-acetic acid ethyl ester; 
 [(4-dipropylamino-butyl)-methyl-amino]-(4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-acetic acid; 
 2-{[(4-dipropylamino-butyl)-methyl-amino]-methyl}-5-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzoic acid ethyl ester; and 
 2-{[(4-dipropylamino-butyl)-methyl-amino]-methyl}-5-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzoic acid. 
 
     
     
         15 . A medical composition, comprising as an active ingredient a compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 . 
     
     
         16 . A method for treating a CXCR4 associated disease comprising administering to a patient in need of such treatment a pharmaceutically effective amount of a compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 . 
     
     
         17 . A method for treating a viral infectious disease comprising administering to a patient in need of such treatment a pharmaceutically effective amount of a compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 . 
     
     
         18 . A method for treating a rheumatic disease, comprising administering to a patient in need of such treatment a pharmaceutically effective amount of a compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 . 
     
     
         19 . A method for treating cancer metastatic disease, comprising administering to a patient in need of such treatment a pharmaceutically effective amount of a compound, a pharmacologically acceptable salt thereof, or a prodrug thereof according to  claim 1 . 
     
     
         20 . A compound represented by the following general formula (1) or a pharmacologically acceptable salt thereof: 
       
         
           
           
               
               
           
         
         wherein
 n 1 , n 2 , and n 3  represent an integer of 1; 
 R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  each independently represent a hydrogen atom; 
 A 1  and A 2  each independently represent a hydrogen atom, a substitutable monocyclic or polycyclic heteroaromatic ring, a partly saturated substitutable polycyclic heteroaromatic ring, a substitutable monocyclic or polycyclic aromatic ring, a partially saturated substitutable polycyclic aromatic ring, a substitutable heteroring, or a group represented by the following formula (2): 
 
       
       
         
           
           
               
               
           
         
         wherein
 R 7 , R 8 , R 9 , and R 10  each independently represent a hydrogen atom, a substitutable alkyl group having 1 to 15 carbon atoms, a substitutable alkenyl group having 2 to 15 carbon atoms, a substitutable alkynyl group having 2 to 15 carbon atoms, or a substitutable cyclic alkyl group having 3 to 15 carbon atoms; 
 W represents a phenyl group; 
 X represents CH 2 ; 
 D represents a group represented by the following formula (6):
   -Q-Y—B  (6)
 
 
 
         wherein
 Q represents NR 12 , wherein R 12  represents —(CH 2 ) m COOR 36 , wherein m represents an integer of 1 or 2 and R 36  represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; 
 Y represents —(CH 2 ) m3 — wherein m3 represents an integer of 0 to 6; and 
 B represents NR 25 R 26  wherein R 25  and R 26  each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms. 
 
       
     
     
         21 - 27 . (canceled) 
     
     
         28 . A rheumatic disease ameliorating agent based on a CXCR4 antagonism, comprising as an active ingredient the compound, or the pharmacologically acceptable salt thereof, according to  claim 20 . 
     
     
         29 . A cancer metastatic disease ameliorating agent based on a CXCR4 antagonism, comprising as an active ingredient the compound, or the pharmacologically acceptable salt thereof according to  claim 20 . 
     
     
         30 . A method of treating a cancer metastatic disease comprising administering the compound or the pharmacologically acceptable salt thereof according to  claim 20 . 
     
     
         31 . A method of treating a rheumatic disease comprising administering the compound or the pharmacologically acceptable salt thereof according to  claim 20 . 
     
     
         32 - 34 . (canceled)