Heteroaryl-substituted 1,3-dihydroindol-2-one derivatives and medicaments containing them

Abstract

The present invention relates to novel 1,3-dihydroindol-2-one (oxindole) derivatives of the formula (I) in which A, R 3 , R 4 , R 5 , R 6 and R 7 are defined according to claim 1 , and to medicaments containing them for the treatment of diseases. In particular, the novel oxindole derivaties can be used for the control and/or prophylaxis of various vasopressin-dependent or oxytocin-dependent diseases.

1 . A compound of the formula (I)  
       
         
           
           
               
               
           
         
       
       in which 
 A is an aromatic heteromonocyclic, or an aromatic or partially aromatic heterobicyclic ring, 
 where the heterocycles are 5- or 6-membered rings and comprise up to 4 heteroatoms selected from the group consisting of N, O and S, and up to 2 oxo groups, where not more than one of the heteroatoms is an oxygen atom,  
 and A may be substituted by radicals R 11 , R 12  and/or R 13 , where  
 R 11 , R 12  and R 13  are selected independently of one another from the group consisting of chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 
 R 3  and R 4  are selected independently of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 , or  
 R 3  and R 4  are connected to give —CH═CH—CH═CH—, —(CH 2 ) 4 — or —(CH 2 ) 3 —,  
 R 5  is a radical (W)—(X)—(Y)—Z, where 
 W is selected from the group consisting of C 1 -C 4 -alkylen, C 2 -C 4 -alkenylen, C 2 -C 4 -alkynylen, O, O—(C 1 -C 4 -alkylen), S, S—(C 1 -C 4 -alkylen), NR 54 , NR 54 —(C 1 -C 4 -alkylen) and a bond,  
 X is selected from the group consisting of CO, CO—O, SO 2 , NR 54 , NR 54 —CO, NR 54 —SO 2 , CO—NR 58  and a bond,  
 Y is C 1 -C 6 -alkylen, C 2 -C 6 -alkenylen, C 2 -C 6 -alkynylen, or a bond,  
 Z is selected from the group consisting of hydrogen, E, O—R 52 , NR 51 R 52 , S—R 52 , where  
 E is an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring having a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms and/or 0 to 2 sulfur atoms, said ring may comprise up to two oxo groups, and may be substituted by radicals R 55 , R 56 , R 57 , and/or up to three radicals R 53 ,  
 R 51  is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl and C 1 -C 4 -alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R 53 ,  
 R 52  is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, E and C 1 -C 4 -alkylen-E,  
 R 53  is selected from the group consisting of chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 R 54  is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C6-alkynyl, phenyl and C 1 -C 4 -alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R 59 ,  
 R 55  is selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C6-alkynyl, phenyl, C 1 -C 4 -alkylen-phenyl, where the ring may be substituted by up to two radicals R 60 , and OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 R 56  is a group Q 1 —Q 2 —Q 3 , where  
 Q 1  is selected from the group consisting of a bond, C 1 -C 4 -alkylen, C 2 -C 4 -alkenylen, C 2 -C 4 -alkynylen, C 1 -C 4 -alkylen-N(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl), C 1 -C 4 -alkylen-NH, NH, N(C 1 -C 4 -alkyl)-C 1 -C 4 -alkylen, NH—C 1 -C 4 -alkylen, O, C 1 -C 4 -alkylen-O, O—C 1 -C 4 -alkylen, CO—NH, CO—N(C 1 -C 4 -alkyl), NH—CO, N(C 1 -C 4 -alkyl)-CO, CO, SO 2 , SO, S, O, SO 2 —NH, SO2—N(C 1 -C 4 -alkyl), NH—SO 2 , N(C 1 -C 4 -alkyl)-SO 2 , O—CO—NH, O—CO—N(C 1 -C 4 -alkyl), NH—CO—O, N(C 1 -C 4 -alkyl)-CO—O, N(C 1 -C 4 -alkyl)-CO—N(C 1 -C 4 -alkyl), NH—CO—N(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl)-CO—NH, and NH—CO—NH,  
 Q 2  is selected from the group consisting of C 1 -C 4 -alkylen, C 2 -C 4 -alkenylen, C 2 -C 4 -alkynylen, and a bond,  
 Q 3  is a hydrogen or an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring having a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms and/or 0 to 2 sulfur atoms, which may comprise up to two oxo groups and may be substituted by the radicals R 63 , R 64  and/or R 65 ,  
 R 57  is selected from the group consisting of C 1 -C 6 -alkyl, phenyl, C 1 -C 4 -alkylen-phenyl, COOH, CO—O—C 1 -C 4 -alkyl, CONH 2 , CO—NH—C 1 -C 4 -alkyl, CO—N(C 1 -C 4 -alkyl) 2 , CO—C 1 -C 4 -alkyl, CH 2 —NH 2 , CH 2 —NH—C 1 -C 4 -alkyl and CH 2 —N(C 1 -C 4 -alkyl) 2 ,  
 R 58  is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl and C 1 -C 4 -alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R 62 ,  
 R 59 , R 60  and R 62  are selected independently of one another from the group consisting of chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 R 63 , R 64  and R 65  are selected independently of one another from the group consisting of chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 R 6  and R 7  are selected independently of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 and their tautomeric forms, enantiomeric and diastereomeric forms, and prodrugs thereof.  
 
 
     
     
         2 . A compound of the formula (II)  
       
         
           
           
               
               
           
         
       
       in which 
 B is selected from the group consisting of thiophene, furan, pyrrole, pyridine, quinoline, tetrahydroquinoline, isoquinoline, tetrahydroisoquinoline, benzothiophene, benzofuran, dihydrobenzofuran, indole, dihydroisoindole,  
 an aromatic heteromonocyclic and an aromatic or partially aromatic heterobicyclic ring, 
 where the heterocycles are 5- or 6-membered rings and comprise 2 to 4 heteroatoms selected from the group consisting of N, O and S, and up to 2 oxo groups, and  
 B may be substituted by the radicals R 21 , R 22  and/or R 23 ,  
 R 21 , R 22  and R 23  are selected independently of one another from the group consisting of chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 , morpholin-4yl, pyrrolidin-1-yl, piperidin-1-yl, 4-piperazin-1-yl, 4-(C 1 -C 4 -alkyl)-piperazin-1-yl,  
 
 R 3  and R 4  are selected independently of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 , or  
 R 3  and R 4  are connected to give —CH═CH—CH═CH—, —(CH 2 ) 4 — or —(CH 2 ) 3 —,  
 R 5  is a radical (W)—(X)—(Y)—Z, where 
 W is selected from the group consisting of C 1 -C 4 -alkylen, C 2 -C 4 -alkenylen, C 2 -C 4 -alkynylen, O, O—(C 1 -C 4 -alkylen), S, S—(C 1 -C 4 -alkylen), NR 54 , NR 54 —(C 1 -C 4 -alkylen) and a bond,  
 X is selected from the group consisting of CO, CO—O, SO 2 , NR 54 , NR 54 —CO, NR 54 —SO 2 , CO—NRC and a bond,  
 Y is C 1 -C 6 -alkylen, C 2 -C 6 -alkenylen, C 2 -C 6 -alkynylen, or a bond,  
 Z is selected from the group consisting of hydrogen, E, O—R 52 , NR 51 R 52 , S—R 52 , where  
 E is an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring having a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms and/or 0 to 2 sulfur atoms, said ring may comprise up to two oxo groups, and may be substituted by radicals R 55 , R 56 , R 57  and/or up to three radicals R 53  and,  
 R 51  is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl and C 1 -C 4 -alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R 53 ,  
 R 52  is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, E and C 1 -C 4 -alkylen-E,  
 R 53  is selected from the group consisting of chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 R 54  is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl and C 1 -C 4 -alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R 59 ,  
 R 55  is selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl, C 1 -C 4 -alkylen-phenyl, where the ring may be substituted by up to two radicals R 60 , and OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 R 56  is a group Q 1 —Q 2 —Q 3 , where  
 Q 1  is selected from the group consisting of a bond, C 1 -C 4 -alkylen, C 2 -C 4 -alkenylen, C 2 -C 4 -alkynylen, C 1 -C 4 -alkylen-N(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl), C 1 -C 4 -alkylen-NH, NH, N(C 1 -C 4 -alkyl)-C 1 -C 4 -alkylen, NH—C 1 -C 4 -alkylen, O, C 1 -C 4 -alkylen-O, O—C 1 -C 4 -alkylen, CO—NH, CO—N(C 1 -C 4 -alkyl), NH—CO, N(C 1 -C 4 -alkyl)-CO, CO, SO 2 , SO, S, O, SO 2 —NH, SO 2 —N(C 1 -C 4 -alkyl), NH—SO 2 , N(C 1 -C 4 -alkyl)-SO 2 , O—CO—NH, O—CO—N(C 1 -C 4 -alkyl), NH—CO—O, N(C 1 -C 4 -alkyl)-CO—O, N(C 1 -C 4 -alkyl)-CO—N(C 1 -C 4 -alkyl), NH—CO—N(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl)-CO—NH, and NH—CO—NH,  
 Q 2  is selected from the group consisting of C 1 -C 4 -alkylen, C 2 -C 4 -alkenylen, C 2 -C 4 -alkynylen, and a bond,  
 Q 3  is a hydrogen or an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring having a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms and/or 0 to 2 sulfur atoms, which may comprise up to two oxo groups and may be substituted by the radicals R 63 , R 64  and/or R 65 ,  
 R 57  is selected from the group consisting of C 1 -C 6 -alkyl, phenyl, C 1 -C 4 -alkylen-phenyl, COOH, CO—O—C 1 -C 4 -alkyl, CONH 2 , CO—NH—C 1 -C 4 -alkyl, CO—N(C 1 -C 4 -alkyl) 2 , CO—C 1 -C 4 -alkyl, CH 2 —NH 2 , CH 2 —NH—C 1 -C 4 -alkyl and CH 2 —N(C 1 -C 4 -alkyl) 2 ,  
 R 58  is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl and C 1 -C 4 -alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R 62 ,  
 R 59 , R 60  and R 62  are selected independently of one another from the group consisting of chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 R 63 , R 64  and R 65  are selected independently of one another from the group consisting of chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 
 R 6  and R 7  are selected independently of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 and their tautomeric forms, enantiomeric and diastereomeric forms, and prodrugs thereof.  
 
     
     
         3 . A compound of the formula (III),  
       
         
           
           
               
               
           
         
       
       in which 
 D is an aromatic heteromonocyclic, or an aromatic or partially aromatic heterobicyclic ring, 
 where the heterocycles are 5- or 6-membered rings and comprise up to 4 heteroatoms selected from the group consisting of N, O and S, and up to 2 oxo groups,  
 and D may be substituted by radicals R 21 , R 22  and/or R 23 ,  
 
 G is an aromatic heteromonocyclic, aromatic or partially aromatic heterobicyclic ring, 
 where the heterocycles are 5- or 6-membered rings and comprise up to 4 heteroatoms selected from the group consisting of N, O and S, and up to 2 oxo groups and  
 G may be substituted by radicals R 71 , R 72  and/or R 73 ,  
 R 21 , R 22 , R 23 , R 71 , R 72  and R 73  are selected independently of one another from the group consisting of chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 , morpholin-4-yl, pyrrolidin-1-yl, piperidin-1-yl, 4-piperazin-1-yl, 4-(C 1 -C 4 -alkyl)-piperazin-1-yl,  
 
 R 3  and R 4  are selected independently of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 , or  
 R 3  and R 4  are connected to give —CH═CH—CH═CH—, —(CH 2 ) 4 — or —(CH 2 ) 3 —,  
 R 5  is a radical (W)—(X)—(Y)—Z, where 
 W is selected from the group consisting of C 1 -C 4 -alkylen, C 2 -C 4 -alkenylen, C 2 - C 4 -alkynylen, O, O—(C 1 -C 4 -alkylen), S, S—(C 1 -C 4 -alkylen), NR 54 , NR 54 —(C 1 -C 4 -alkylen) and a bond,  
 X is selected from the group consisting of CO, CO—O, SO 2 , NR 54 , NR 54 —CO, NR 54 —SO 2 , CO—NR 58  and a bond,  
 Y is C 1 -C 6 -alkylen, C 2 -C 6 -alkenylen, C 2 -C 6 -alkynylen, or a bond,  
 Z is selected from the group consisting of hydrogen, E, O—R 52 , NR 51 R 52 , S—R 52 , where  
 E is an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring having a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms and/or 0 to 2 sulfur atoms, which may comprise up to two oxo groups, and E may be substituted by radicals R 55 , R 56 , R 57  and/or up to three radicals R 53 ,  
 R 51  is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl and C 1 -C 4 -alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R 53 ,  
 R 52  is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, E and C 1 -C 4 -alkylen-E,  
 R 53  is selected from the group consisting of chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 R{cube root}is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl and C 1 -C 4 -alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R 59 ,  
 R 55  is selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl, C 1 -C 4 -alkylen-phenyl, where the ring may be substituted by up to two radicals R 60 , and OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 R 56  is a group Q 1 —Q 2 —Q 3 , where  
 Q 1  is selected from the group consisting of a bond, C 1 -C 4 -alkylen, C 2 -C 4 -alkenylen, C 2 -C 4 -alkynylen, C 1 -C 4 -alkylen-N(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl), C 1 -C 4 -alkylen-NH, NH, N(C 1 -C 4 -alkyl)-C 1 -C 4 -alkylen, NH—C 1 -C 4 -alkylen, O, C 1 -C 4 -alkylen-O, O—C 1 -C 4 -alkylen, CO—NH, CO—N(C 1 -C 4 -alkyl), NH—CO, N(C 1 -C 4 -alkyl)-CO, CO, SO 2 , SO, S, O, SO 2 —NH, SO 2 —N(C 1 -C 4 -alkyl), NH—SO 2 , N(C 1 -C 4 -alkyl)-SO 2 , O—CO—NH, O—CO—N(C 1 -C 4 -alkyl), NH—CO—O, N(C 1 -C 4 -alkyl)-CO—O, N(C 1 -C 4 -alkyl)-CO—N(C 1 -C 4 -alkyl), NH—CO—N(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl)-CO—NH, and NH—CO—NH,  
 Q 2  is selected from the group consisting of C 1 -C 4 -alkylen, C 2 -C 4 -alkenylen, C 2 -C 4 -alkynylen, and a bond,  
 Q 3  is a hydrogen or an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring having a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms and/or 0 to 2 sulfur atoms, which may comprise up to two oxo groups and may be substituted by the radicals R 63 , R 64  and/or R 65 ,  
 R 57  is selected from the group consisting of C 1 -C 6 -alkyl, phenyl, C 1 -C 4 -alkylen-phenyl, COOH, CO—O—C 1 -C 4 -alkyl, CONH 2 , CO—NH—C 1 -C 4 -alkyl, CO—N(C 1 -C 4 -alkyl) 2 , CO—C 1 -C 4 -alkyl, CH 2 —NH 2 , CH 2 —NH—C 1 -C 4 -alkyl and CH 2 —N(C 1 -C 4 -alkyl) 2 ,  
 R 58  is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl and C 1 -C 4 -alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R 62 ,  
 R 59 , R 60  and R 62  are selected independently of one another from the group consisting of chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 R 63 , R 64  and R 65  are selected independently of one another from the group consisting of chlorine, bromine, iodine, fluorine, CN, CF 3 , OCF 3 , NO 2 , OH, O—C 1 -C 4 -alkyl, O-phenyl, O—C 1 -C 4 -alkylen-phenyl, phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, NH 2 , NH(C 1 -C 4 -alkyl) and N(C 1 -C 4 -alkyl) 2 ,  
 and their tautomeric forms, enantiomeric and diastereomeric forms, and prodrugs thereof.  
 
 
     
     
         4 . A medicament comprising a compound as claimed in  claim 1 .  
     
     
         5 . The use of a compound as claimed in  claim 1  for the control and/or prophylaxis of various vasopressin-dependent or oxytocin-dependent diseases.  
     
     
         6 . A method for the therapeutic and/or prophylactic treatment of a mammal requiring a treatment by administering a compound as claimed in  claim 1  for the treatment of diseases.  
     
     
         7 . The use of a compound as claimed in  claim 1  for the treatment of depressions and/or bipolar disorders such as, for example, dysthymic disorders, subsyndromal depression, seasonal affected disorders, premenstrual dysphoric disorders and/or psychotic disorders.  
     
     
         8 . The use of a compound as claimed in  claim 1  for the treatment of anxiety and/or stress-related disorders such as, for example, general anxiety disorders, panic disorders, obsessive-compulsive disorders, post-traumatic disorders, acute stress disorders and/or social phobia.  
     
     
         9 . The use of a compound as claimed in  claim 1  for the treatment of memory disorders and/or Alzheimer's disease.  
     
     
         10 . The use of a compound as claimed in  claim 1  for the treatment of psychoses and/or psychotic disorders.  
     
     
         11 . The use of a compound as claimed in  claim 1  for the treatment of Cushing's syndrome.