Substituted nitrogen-containing heterobicycles, the preparation thereof and their use as pharmaceutical compositions

Abstract

The present invention relates to new substituted nitrogen-containing heterobicyclic compounds of general formula wherein B, X 1 to X 3 and R 1 to R 5 are defined as in claim 1 , the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable properties. The compounds of the above general formula I as well as the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, and their stereoisomers have valuable pharmacological properties, particularly an antithrombotic activity and a factor Xa-inhibiting activity.

1 . A substituted nitrogen-containing heterobicyclic compound of formula 
     
       
         
         
             
             
         
       
       wherein 
       R 1  denotes an amino, C 1-5 -alkylamino, C 3-7 -cycloalkylamino or (phenyl-C 1-3 -alkyl)-amino group which may in each case additionally be substituted at the amino nitrogen atom by a phenylcarbonyl or phenylsulphonyl group or by a C 1-5 -alkyl or C 1-5 -alkylcarbonyl group optionally substituted in the alkyl moiety by a hydroxy, C 1-3 -alkoxy or carboxy group, a group which may be converted in vivo into a carboxy group, an amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino or a 4- to 7-membered cycloalkyleneimino group, while in the substitution of the previously mentioned C 1-5 -alkyl group two heteroatoms are separated from one another by at least two carbon atoms, 
       a 4- to 7-membered cycloalkyleneiminocarbonyl or cycloalkyleneiminosulphonyl group, while
 the cycloalkyleneimino moiety may be substituted in the carbon skeleton by one or two C 1-3 -alkyl, C 2-3 -alkenyl, C 2-3 -alkynyl, phenyl-C 1-3 -alkyl, 1,1-diphenyl-C 1-3 -alkyl, hydroxy-C 1-3 -alkyl, C 1-3 -alkyloxy-C 1-3 -alkyl, heteroaryl-C 1-3 -alkyl, carboxy-C 1-3 -alkyl, C 1-3 -alkyloxycarbonyl-C 1-3 -alkyl, amino-C 1-5 -alkyl, C 1-5 -alkylamino-C 1-5 -alkyl, C 3-6 -cycloalkylamino-C 1-3 -alkyl, phenylamino-C 1-3 -alkyl, di-(C 1-5 -alkyl)-amino-C 1-5 -alkyl, N—(C 3-6 -cycloalkyl)-C 1-3 -alkylamino-C 1-3 -alkyl, a 4- to 7-membered cycloalkyleneimino-C 1-5 -alkyl, N—C 1-3 -alkylpiperazin-4-yl-C 1-3 -alkyl, N-(heteroaryl-C 1-3 -alkyl)-C 1-3 -alkylamino-C 1-3 -alkyl, C 1-3 -alkylcarbonylamino-C 1-3 -alkyl, C 1-3 -alkylsulphonylamino-C 1-3 -alkyl, C 1-5 -alkyloxycarbonylamino-C 1-3 -alkyl, aminocarbonylamino-C 1-3 -alkyl, C 1-3 -alkylaminocarbonylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-aminocarbonylamino-C 1-3 -alkyl, C 1-3 -alkylcarbonyl, carboxy, C 1-5 -alkyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl, C 3-6 -cycloalkylaminocarbonyl, di-(C 1-3 -alkyl)-aminocarbonyl, N—(C 3-7 -cycloalkyl)-C 1-5 -alkylaminocarbonyl, N-(phenyl-C 1-3 -alkyl)-C 1-5 -alkylaminocarbonyl, a 4- to 7-membered cycloalkyleneiminocarbonyl, hydroxy, C 1-3 -alkyloxy, allyloxy, propargyloxy, benzyloxy, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, a 4- to 7-membered cycloalkyleneimino, a phenyl or a 5- to 6-membered heteroaryl group, with the proviso that in the substitution of a methylene group adjacent to the imino group two heteroatoms are separated from one another by at least two carbon atoms, and/or 
 a methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be replaced by a sulphur atom, a sulphinyl or sulphonyl group or 
 a methylene group in the 2 position of a 5-membered cycloalkyleneimino group may be replaced by an —NH— group or 
 a methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, a methylidene, carbonyl, sulphinyl or sulphonyl group or by a —NH— group optionally substituted by a C 1-3 -alkyl, hydroxy, formyl, C 1-3 -alkylcarbonyl or phenylcarbonylamino group, while additionally a methylene group adjacent to a previously mentioned —NH— group may be replaced by a carbonyl or sulphonyl group, with the proviso that
 in the substitution of the previously mentioned 6- to 7-membered cycloalkyleneimino groups, wherein a methylene group is replaced by an oxygen or sulphur atom, a sulphinyl or sulphonyl group, two heteroatoms are separated from one another by at least two carbon atoms, 
 
 a —CH 2 —CH 2 — group in a 5- to 7-membered cycloalkyleneimino group may be replaced by an —NH—CO—, —CO—NH—, —CO—N(CH 3 )— or a —N(CH 3 )—CO— group, with the proviso that
 a cycloalkyleneimino group as hereinbefore defined wherein two nitrogen atoms are separated from one another by precisely one —CH 2 — group is excluded, 
 
 
       a 5- to 7-membered cycloalkenyleneiminocarbonyl or cycloalkenyleneiminosulphonyl group optionally substituted by one or two C 1-3 -alkyl, amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl, 4- to 7-membered cycloalkyleneimino-C 1-3 -alkyl, C 3-6 -cycloalkylamino-C 1-3 -alkyl, phenyl, phenyl-C 1-3 -alkyl, heteroaryl, heteroaryl-C 1-3 -alkyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl, di-(C 1-3 -alkyl)-aminocarbonyl or 4- to 7-membered cycloalkyleneiminocarbonyl groups, while the double bond is not bound to a nitrogen atom and may be fused to a 5- or 6-membered heteroaryl group, 
       an aminocarbonyl or aminosulphonyl group optionally substituted by one or two C 1-5 -alkyl, C 3-6 -cycloalkyl, 5- to 7-membered cycloalkyleneimino, pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl or N—C 1-3 -alkyl-piperazinyl groups,
 while the substituents may be identical or different and 
 in each case one of the previously mentioned C 1-5 -alkyl groups may be substituted by one or two hydroxy-C 1-3 -alkyl, C 1-3 -alkoxy-C 1-3 -alkyl, benzyloxy-C 1-3 -alkyl, amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl, 4- to 7-membered cyclo-alkyleneimino, C-pyrrolidinyl, C-piperidinyl, C-morpholinyl, C-piperazinyl, C 1-5 -alkyloxycarbonylamino-C 1-3 -alkyl, C 3-6 -cycloalkylamino-C 1-3 -alkyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl, N—(C 3-7 -cycloalkyl)-C 1-5 -alkylaminocarbonyl, N-(phenyl-C 1-3 -alkyl)-C 1-5 -alkylaminocarbonyl, di-(C 1-3 -alkyl)-aminocarbonyl or 4- to 7-membered cycloalkyleneiminocarbonyl groups, while
 the cycloalkyleneimino groups previously mentioned in the groups may additionally be substituted by a carboxy or C 1-5 -alkyloxycarbonyl group, 
 
 
       a C 1-7 -alkylcarbonyl or C 3-7 -cycloalkylcarbonyl group, while
 the methylene group in the 2, 3 or 4 position in a C 3-7 -cycloalkylcarbonyl group may be replaced by an oxygen or sulphur atom, a carbonyl, sulphinyl, sulphonyl or an —NH— group, wherein 
 the hydrogen atom of the —NH— group may be replaced by a C 1-3 -alkyl or C 1-3 -alkyl-carbonyl group, 
 
       a phenylcarbonyl or heteroarylcarbonyl group which may be substituted in the phenyl or heteroaryl moiety by a fluorine, chlorine or bromine atom, by a trifluoromethyl, C 1-3 -alkyl, amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl, a 4- to 7-membered cycloalkyleneimino-C 1-3 -alkyl or C 1-3 -alkoxy group, 
       a C 1-3 -alkyl group optionally monosubstituted by an amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, hydroxy, phenyl, heteroaryl or a 4- to 7-membered cycloalkyleneimino group, while
 the phenyl moiety may be substituted by a fluorine, chlorine or bromine atom, by a trifluoromethyl, C 1-3 -alkyl, amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl, a 4- to 7-membered cycloalkyleneimino-C 1-3 -alkyl or C 1-3 -alkoxy group and/or 
 a —CH 2 —CH 2 — group in a 5- to 7-membered cycloalkyleneimino group may be replaced by a —NH—CO—, —CO—NH—, —NH—SO 2 —, —SO 2 —NH—, —CO—N(CH 3 )— or a —N(CH 3 )—CO group or 
 a methylene group, which is adjacent to the nitrogen atom, in a 5- to 7-membered cycloalkyleneimino group may be replaced by a carbonyl group, 
 
       or a group of formulae 
     
     
       
         
         
             
             
         
       
       
         wherein in the heterocyclic moiety in each case a hydrogen atom may be replaced by a C 1-3 -alkyloxycarbonyl, C 1-5 -alkyloxycarbonylamino-C 1-3 -alkyl, methylsulphonylmethyl, amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl, aminocarbo-nyl, C 1-3 -alkylaminocarbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group and 
         m denotes the number 1, 2 or 3, 
       
       R 2  denotes a hydrogen, fluorine, chlorine or bromine atom, a C 1-3 -alkyl group wherein the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a C 2-3 -alkenyl, C 2-3 -alkynyl, nitro, amino, C 1-3 -alkoxy, a mono-, di- or trifluoromethoxy group, 
       R 3  denotes a hydrogen atom or a C 1-3 -alkyl group, 
       R 4  denotes a hydrogen atom or a straight-chain or branched C 1-5 -alkyl group which is optionally substituted by a fluorine atom, a C 2-3 -alkenyl, C 2-3 -alkynyl, mono-, di- or trifluoromethyl, a hydroxy, C 1-5 -alkyloxy, allyloxy, propargyloxy, phenyloxy, heteroaryloxy, benzyloxy, C 1-5 -alkylcarbonyloxy, C 1-5 -alkyloxycarbonyloxy, carboxy-C 1-3 -alkyloxy, C 1-5 -alkyloxycarbonyl-C 1-3 -alkyloxy, C 1-8 -alkyloxycarbonylamino, mercapto, C 1-3 -alkylsulphanyl, C 1-3 -alkylsulphinyl, C 1-3 -alkylsulphonyl, carboxy, C 1-5 -alkyloxycarbonyl, allyloxycarbonyl, propargyloxycarbonyl, benzyloxycarbonyl, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, a 4- to 7-membered cycloalkyleneimino, C 1-5 -alkylcarbonylamino, C 1-3 -alkylsulphonylamino, C 3-6 -cycloalkylcarbonylamino, benzyloxycarbonylamino, phenylcarbonylamino or guanidino group, 
       a group of general formula 
     
     
       
         
         
             
             
         
       
       wherein
 o denotes one of the numbers 1, 2, 3, 4 or 5, 
 p denotes one of the numbers 0, 1, 2 or 3, 
 R 11  denotes a hydrogen atom or a C 1-3 -alkyl group and 
 A denotes a C 3-7 -cycloalkyl group wherein
 the methyne group in the 1 position may be replaced by a nitrogen atom, if p denotes one of the numbers 2, 3, 4 or 5, and/or 
 a methylene group of a previously mentioned cycloalkyl group may be replaced by an oxygen or sulphur atom, a —NH—, —N(OH)—, —N(C 1-3 -alkyl)-, —N(C 1-3 -alkylcarbonyl)- or —N(heteroaryl)-group with the proviso that in a group —N(R 11 )—(CH 2 ) p -A- thus formed two heteroatoms are separated from one another by at least two carbon atoms, and/or 
 a methylene group adjacent to an —NH—, —N(OH)—, —N(C 1-3 -alkyl)-, —N(C 1-3 -alkylcarbonyl)- or —N(heteroaryl)-group may be replaced by a carbonyl, sulphinyl or sulphonyl group, 
 
 
       a 4- to 7-membered cycloalkyleneiminocarbonyl-C 1-5 -alkyl group, while
 a methylene group of the cycloalkyleneimino moiety may be substituted by a C 1-3 -alkyl group optionally substituted by a hydroxy, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, a 4- to 7-membered cycloalkyleneimino, morpholino, piperazinyl, N—(C 1-3 -alkyl)-piperazinyl or C 1-5 -alkyloxycarbonylamino group and a methylene group of the cycloalkyleneimino moiety not adjacent to the imino group may be substituted by a hydroxy, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, aminocarbonyl, C 1-3 -alkylaminocarbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group and/or 
 a methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be replaced by a sulphur atom, a carbonyl, sulphinyl or sulphonyl group or 
 a methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a carbonyl, sulphinyl, sulphonyl or by an —NH— group optionally substituted by a C 1-3 -alkyl or heteroaryl group and additionally a methylene group adjacent to an above-mentioned —NH— or —N(C 1-3 -alkyl)-group may be replaced by a carbonyl group and/or 
 two geminal hydrogen atoms of a methylene group in a previously mentioned cycloalkyleneimino group may be substituted by a 5- to 7-membered carbocyclic group forming a spiro compound, while one or two methylene groups of the previously mentioned carbocyclic group which are not adjacent to each other may independently of one another be replaced by an oxygen or sulphur atom or an —NH—, —N(OH)— or —N(C 1-3 -alkyl)-group and additionally a methylene group of the carbocyclic group adjacent to an —NH—, —N(OH)—, or —N(C 1-3 -alkyl)-group may be replaced by a carbonyl, sulphinyl or sulphonyl group, or 
 a phenyl or heteroaryl group may be fused to two adjacent methylene groups in the 2 and 3 position of a previously mentioned 5-membered cycloalkyleneimino group or in the 3 and 4 position of a previously mentioned 6- to 7-membered cycloalkyleneimino group, 
 
       an aminocarbonyl-C 1-5 -alkyl, aminosulphonyl-C 1-3 -alkyl, C 1-3 -alkylaminocarbonyl-C 1-5 -alkyl or C 1-3 -alkylaminosulphonyl-C 1-3 -alkyl group, while
 the previously mentioned amino groups may additionally be substituted by a C 3-6 -cycloalkyl-C 1-3 -alkyl, phenyl-C 1-3 -alkyl, heteroaryl-C 1-3 -alkyl, heteroarylamino-C 2-3 -alkyl, hydroxy-C 2-3 -alkyl, C 1-3 -alkyloxy-C 2-3 -alkyl, carboxy-C 1-3 -alkyl, C 1-5 -alkyloxycarbonyl-C 1-3 -alkyl, amino-C 2-3 -alkyl, C 1-3 -alkylamino-C 2-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 2-3 -alkyl, aminocarbonyl-C 1-3 -alkyl, C 1-3 -alkylaminocarbonyl-C 1-3 -alkyl, di-(C 1-3 -alkyl)-aminocarbonyl-C 1-3 -alkyl group, 
 
       a phenyl or heteroaryl, phenyl-C 1-3 -alkyl or heteroaryl-C 1-3 -alkyl group which is optionally substituted by a fluorine, chlorine or bromine atom, an amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, hydroxy, C 1-4 -alkyloxy, a mono-, di- or trifluoromethoxy, benzyloxy, carboxy-C 1-3 -alkoxy, C 1-3 -alkyloxycarbonyl-C 1-3 -alkyloxy, aminocarbonyl-C 1-3 -alkyloxy, C 1-3 -alkylaminocarbonyl-C 1-3 -alkyloxy, di-(C 1-3 -alkyl)-aminocarbonyl-C 1-3 -alkyloxy, a 4- to 7-membered cycloalkyleneiminocarbonyl-C 1-3 -alkoxy, carboxy or C 1-3 -alkyloxycarbonyl group, 
       a 4- to 7-membered cycloalkyleneimino-C 1-5 -alkyl group wherein
 a methylene group of the cycloalkyleneimino moiety may be replaced by an oxygen or sulphur atom, a carbonyl, sulphinyl or sulphonyl group, an —NH—, —N(OH)—, —N(C 1-3 -alkyl)- or —N(C 1-3 -alkylcarbonyl)-group, 
 
       a 4- to 7-membered cycloalkyl-C 1-5 -alkyl group wherein in the cyclic moiety a methylene group may be replaced by an —NH— or —N(C 1-3 -alkyl)-group and wherein a methylene group adjacent to the —NH— or —N(C 1-3 -alkyl)-group may be replaced in each case by a carbonyl group, with the proviso that a cycloalkyleneimino group as hereinbefore defined wherein two nitrogen atoms are separated from one another by precisely one —CH 2 — group are excluded, 
       R 5  denotes a hydrogen atom or a C 1-3 -alkyl group or 
       R 4  and R 5  together with the carbon atom to which they are bound denote a C 3-7 -cycloalkyl group, while
 one of the methylene groups of the C 3-7 -cycloalkyl group may be replaced by an imino, C 1-3 -alkylimino, acylimino or sulphonylimino group, 
 
       B denotes a group of formulae 
     
     
       
         
         
             
             
         
       
       wherein
 n denotes the number 1 or 2, 
 R 6  denotes a hydrogen atom or a C 1-3 -alkyl, hydroxy, amino, C 1-3 -alkylamino group, 
 R 7  denotes a hydrogen, fluorine, chlorine or bromine atom, a C 1-3 -alkyl group wherein the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a C 2-3 -alkenyl or C 2-3 -alkynyl, a hydroxy, C 1-3 -alkoxy, trifluoromethoxy or cyano group, and 
 
       X 1  is N 
       X 2 , X 3  is a CH group optionally substituted by a C 1-3 -alkyl group 
       while, unless otherwise stated, the expression “heteroaryl group” mentioned hereinbefore in the definitions denotes a monocyclic 5- or 6-membered heteroaryl group optionally substituted in the carbon skeleton by a C 1-3 -alkyl, carboxy, C 1-3 -alkoxy-carbonyl or C 1-3 -alkoxycarbonylamino group, while
 the 6-membered heteroaryl group contains one, two or three nitrogen atoms and
 the 5-membered heteroaryl group contains one or two imino groups optionally substituted by a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group, or an oxygen or sulphur atom or 
 an imino group optionally substituted by a C 1-3 -alkyl, amino-C 2-3 -alkyl, C 1-3 -alkylamino-C 2-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 2-3 -alkyl, a 4- to 7-membered cycloalkyleneimino-C 1-3 -alkyl or phenyl-C 1-3 -alkyl group, or an oxygen or sulphur atom and additionally a nitrogen atom or 
 an imino group optionally substituted by a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group and two or three nitrogen atoms, 
 and also a phenyl ring may be fused to the above-mentioned monocyclic heteroaryl groups via two adjacent carbon atoms 
 and the bond is effected via a nitrogen atom or via a carbon atom of the heterocyclic moiety or a fused-on phenyl ring, 
 
 
       while unless otherwise stated the alkyl and alkoxy groups contained in the above definitions which have more than two carbon atoms may be straight-chain or branched and the alkyl groups in the above-mentioned dialkylated groups, for example the dialkylamino groups, may be identical or different, 
       and the hydrogen atoms of the methyl or ethyl groups contained in the above-mentioned definitions may be wholly or partly replaced by fluorine atoms, 
       the tautomer, the diastereomer, the enantiomer, mixtures thereof and the salt thereof, 
       while by a group which may be converted in vivo into a carboxy group is meant for example a carboxy group esterified with an alcohol wherein the alcohol moiety is preferably a C 1-6 -alkanol, a phenyl-C 1-3 -alkanol, a C 3-9 -cycloalkanol, a C 5-7 -cycloalkenol, a C 3-5 -alkenol, a phenyl-C 3-5 -alkenol, a C 3-5 -alkynol or phenyl-C 3-5 -alkynol, with the proviso that no bond to the oxygen atom starts from a carbon atom which carries a double or triple bond, a C 3-8 -cycloalkyl-C 1-3 -alkanol or an alcohol of formula
   R 8 —CO—O—(R 9 CR 10 )—OH, 
 
       wherein
 R 5  denotes a C 1-8 -alkyl, C 5-7 -cycloalkyl, phenyl or phenyl-C 1-3 -alkyl group, 
 R 9  denotes a hydrogen atom, a C 1-3 -alkyl, C 5-7 -cycloalkyl or phenyl group and 
 R 10  denotes a hydrogen atom or a C 1-3 -alkyl group. 
 
     
   
   
       2 . The substituted nitrogen-containing heterobicyclic compound of formula I according to  claim 1 , wherein
 R 1  denotes an amino, C 1-5 -alkylamino, C 3-7 -cycloalkylamino or (phenyl-C 1-3 -alkyl)-amino group which may in each case additionally be substituted at the amino nitrogen atom by a C 1-5 -alkyl or C 1-5 -alkylcarbonyl group, optionally substituted in the alkyl moiety by a hydroxy, C 1-3 -alkoxy or carboxy group, a group which may be converted in vivo into a carboxy group, an amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino or a 4- to 7-membered cycloalkyleneimino group, while in the substitution of the previously mentioned C 1-5 -alkyl group two heteroatoms are separated from one another by at least two carbon atoms,   a 4- to 7-membered cycloalkyleneiminocarbonyl or cycloalkyleneiminosulphonyl group, while
 the cycloalkyleneimino moiety in the carbon skeleton may be substituted by one or two C 1-3 -alkyl, phenyl-C 1-3 -alkyl, 1,1-diphenyl-C 1-3 -alkyl, hydroxy-C 1-3 -alkyl, C 1-3 -alkyloxy-C 1-3 -alkyl, heteroaryl-C 1-3 -alkyl, carboxy-C 1-3 -alkyl, C 1-3 -alkyloxycarbonyl-C 1-3 -alkyl, amino-C 1-5 -alkyl, C 1-5 -alkylamino-C 1-5 -alkyl, C 3-6 -cycloalkylamino-C 1-3 -alkyl, phenylamino-C 1-3 -alkyl, di-(C 1-5 -alkyl)-amino-C 1-5 -alkyl, N—(C 3-6 -cycloalkyl)-C 13 -al-kylamino-C 1-3 -alkyl, 4- to 7-membered cycloalkyleneimino-C 1-3 -alkyl, N—C 1-3 -alkyl-piperazin-4-yl-C 1-3 -alkyl, N-(heteroaryl-C 1-3 -alkyl)-C 1-3 -alkylamino-C 1-3 -alkyl, C 1-3 -alkylcarbonylamino-C 1-3 -alkyl, C 1-3 -alkylsulphonylamino-C 1-3 -alkyl, C 1-5 -alkyl-oxycarbonylamino-C 1-3 -alkyl, aminocarbonylamino-C 1-3 -alkyl, C 1-3 -alkylamino-carbonylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-aminocarbonylamino-C 1-3 -alkyl, C 1-3 -alkyl-carbonyl, carboxy, C 1-5 -alkyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl, C 3-6 -cycloalkylaminocarbonyl, di-(C 1-3 -alkyl)-aminocarbonyl, N—(C 3-7 -cycloalkyl)-C 1-5 -alkylaminocarbonyl, N-(phenyl-C 1-3 -alkyl)-C 1-5 -alkylaminocarbonyl, a 4- to 7-membered cycloalkyleneiminocarbonyl, hydroxy, C 1-3 -alkyloxy, allyloxy, propargyloxy, benzyloxy, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, a 4- to 7-membered cycloalkyleneimino, a phenyl or a 5- to 6-membered heteroaryl group, with the proviso that in the substitution of a methylene group adjacent to the imino group two heteroatoms are separated from one another by at least two carbon atoms, and/or 
 a methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be replaced by a sulphur atom, a sulphinyl or sulphonyl group or 
 a methylene group in the 2 position of a 5-membered cycloalkyleneimino group may be replaced by an —NH— group or 
 a methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, a methylidene, carbonyl, sulphinyl or sulphonyl group or by an —NH— group optionally substituted by a C 1-3 -alkyl, hydroxy, formyl, C 1-3 -alkylcarbonyl or phenylcarbonylamino group, while additionally a methylene group adjacent to a previously mentioned —NH— group may be replaced by a carbonyl or sulphonyl group, with the proviso that
 in the substitution of the previously mentioned 6- to 7-membered cycloalkyleneimino groups, wherein a methylene group is replaced by an oxygen or sulphur atom, a sulphinyl or sulphonyl group, two heteroatoms are separated from one another by at least two carbon atoms, and/or 
 
 a —CH 2 —CH 2 — group in a 5- to 7-membered cycloalkyleneimino group may be replaced by a —NH—CO—, —CO—NH—, —CO—N(CH 3 )— or a —N(CH 3 )—CO— group with the proviso that
 a cycloalkyleneimino group as hereinbefore defined wherein two nitrogen atoms are separated from one another by precisely one —CH 2 — group is excluded, 
 
   a 5- to 7-membered cycloalkenyleneiminocarbonyl group optionally substituted by one or two C 1-3 -alkyl, amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl, 4- to 7-membered cycloalkyleneimino-C 1-3 -alkyl or C 3-6 -cycloalkylamino-C 1-3 -alkyl groups, while the double bond is not bound to a nitrogen atom and may be fused to a 5- or 6-membered heteroaryl group,   an aminocarbonyl group optionally substituted by one or two C 1-5 -alkyl, C 3-6 -cycloalkyl, 5- to 7-membered cycloalkyleneimino, pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl or N—C 1-3 -alkylpiperazinyl groups,
 while the substituents may be identical or different and 
 in each case one of the previously mentioned C 1-5 -alkyl groups may be substituted by one or two hydroxy-C 1-3 -alkyl, C 1-3 -alkoxy-C 1-3 -alkyl, benzyloxy-C 1-3 -alkyl, amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl, 4- to 7-membered cyclo-alkyleneimino-C 1-3 -alkyl, C-pyrrolidinyl, C-piperidinyl, C-morpholinyl, C-piperazinyl, C 3-6 -cycloalkylamino-C 1-3 -alkyl or 4- to 7-membered cycloalkyleneiminocarbonyl groups, while
 the cycloalkyleneimino groups previously mentioned in the groups may additionally be substituted by a carboxy or C 1-5 -alkyloxycarbonyl group, 
 
   a phenylcarbonyl or heteroarylcarbonyl group which may be substituted in the phenyl or heteroaryl moiety by a fluorine, chlorine or bromine atom, by a trifluoromethyl, C 1-3 -alkyl, amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl, a 4- to 7-membered cycloalkyleneimino-C 1-3 -alkyl or C 1-3 -alkoxy group,   a C 1-3 -alkyl group optionally monosubstituted by a di-(C 1-3 -alkyl)-amino, heteroaryl or a 4- to 7-membered cycloalkyleneimino group, while
 a —CH 2 —CH 2 — group in a 5- to 7-membered cycloalkyleneimino group may be replaced by a —NH—CO—, —CO—NH—, —NH—SO 2 —, —SO 2 —NH—, —CO—N(CH 3 )— or a —N(CH 3 )—CO— group or 
 a methylene group, which is adjacent to the nitrogen atom, in a 5- to 7-membered cycloalkyleneimino group may be replaced by a carbonyl group, 
   or a group of formulae   
     
       
         
         
             
             
         
       
       
         wherein in the heterocyclic moiety in each case a hydrogen atom may be replaced by a C 1-3 -alkyloxycarbonyl, C 1-5 -alkyloxycarbonylamino-C 1-3 -alkyl, methylsulphonylmethyl, amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl, aminocarbo-nyl, C 1-3 -alkylaminocarbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group and 
         m denotes the number 1, 2 or 3, 
       
       R 2  denotes a chlorine or bromine atom, a C 1-3 -alkyloxy or C 1-3 -alkyl group wherein the hydrogen atoms may be wholly or partly replaced by fluorine atoms, or a C 2-3 -alkenyl group, 
       R 3  denotes a hydrogen atom, 
       R 4  denotes a hydrogen atom or a straight-chain or branched C 1-5 -alkyl group which is optionally substituted by a C 2-3 -alkenyl, C 2-3 -alkynyl, hydroxy, C 1-5 -alkyloxy, phenyloxy, heteroaryloxy, benzyloxy, C 1-5 -alkylcarbonyloxy, carboxy-C 1-3 -alkyloxy, C 1-5 -alkyloxycarbonyl-C 1-3 -alkyloxy, C 1-5 -alkyloxycarbonylamino, mercapto, C 1-3 -alkylsulphanyl, C 1-3 -alkylsulphinyl, C 1-3 -alkylsulphonyl, carboxy, C 1-5 -alkyloxycarbonyl, allyloxycarbonyl, propargyloxycarbonyl, benzyloxycarbonyl, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, a 4- to 7-membered cycloalkyleneimino, C 1-5 -alkylcarbonylamino, C 1-3 -alkylsulphonylamino, C 3-6 -cycloalkylcarbonylamino, benzyloxycarbonylamino or phenylcarbonylamino group, 
       a group of general formula 
     
     
       
         
         
             
             
         
       
       wherein
 o denotes one of the numbers 1, 2 or 3, 
 p denotes one of the numbers 0, 1, 2 or 3, 
 R 11  denotes a hydrogen atom or a C 1-3 -alkyl group and 
 A denotes a C 3-7 -cycloalkyl group wherein
 the methyne group in the 1 position may be replaced by a nitrogen atom, if p denotes one of the numbers 2 or 3, and/or 
 a methylene group of a previously mentioned cycloalkyl groups may be replaced by an oxygen or sulphur atom, a —NH—, —N(OH)—, —N(C 1-3 -alkyl)-, —N(C 1-3 -alkylcarbonyl)- or —N(heteroaryl)-group, with the proviso that in an —N(R 11 )—(CH 2 ) p -A-group thus formed two heteroatoms are separated from one another by at least two carbon atoms, and/or 
 a methylene group adjacent to a —NH—, —N(OH)—, —N(C 1-3 -alkyl)-, —N(C 1-3 -alkylcarbonyl)- or —N(heteroaryl)-group may be replaced by a carbonyl, sulphinyl or sulphonyl group, 
 
 
       a 4- to 7-membered cycloalkyleneiminocarbonyl-C 1-5 -alkyl group, while
 a methylene group of the cycloalkyleneimino moiety may be substituted by a C 1-3 -alkyl group optionally substituted by a hydroxy, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, a 4- to 7-membered cycloalkyleneimino, morpholino, piperazinyl-N—(C 1-3 -alkyl)-piperazinyl or C 1-5 -alkyloxycarbonylamino group and a methylene group of the cycloalkyleneimino moiety not adjacent to the imino group may be substituted by a hydroxy, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, aminocarbonyl, C 1-3 -alkylaminocarbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group and/or 
 a methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be replaced by a sulphur atom, a carbonyl, sulphinyl or sulphonyl group or 
 a methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a carbonyl, sulphinyl, sulphonyl or by a —NH-group optionally substituted by a C 1-3 -alkyl or heteroaryl group and additionally a methylene group adjacent to an above-mentioned —NH— or —N(C 1-3 -alkyl)-group may be replaced by a carbonyl group and/or 
 two geminal hydrogen atoms of a methylene group in a previously mentioned cycloalkyleneimino group may be substituted by a 5- to 7-membered carbocycle forming a spiro compound, while one or two methylene groups of the aforementioned carbocycle which are not adjacent to one another may independently of one another be replaced by an oxygen or sulphur atom or a —NH—, —N(OH)—, or —N(C 1-3 -alkyl)-group and additionally a methylene group of the carbocyclic group adjacent to an —NH—, —N(OH)—, or —N(C 1-3 -alkyl)-group may be replaced by a carbonyl, sulphinyl or sulphonyl group, or 
 a phenyl or heteroaryl group may be fused to two adjacent methylene groups in the 2 and 3 position of a previously mentioned 5-membered cycloalkyleneimino group or in the 3 and 4 position of a previously mentioned 6- to 7-membered cycloalkyleneimino group, 
 
       an aminocarbonyl-C 1-5 -alkyl, aminosulphonyl-C 1-3 -alkyl, C 1-3 -alkylaminocarbonyl-C 1-5 -alkyl or C 1-3 -alkylaminosulphonyl-C 1-3 -alkyl group, while
 the previously mentioned amino groups may additionally be substituted by a C 3-6 -cycloalkyl-C 1-3 -alkyl, phenyl-C 1-3 -alkyl, heteroaryl-C 1-3 -alkyl, heteroarylamino-C 2-3 -alkyl, hydroxy-C 2-3 -alkyl, C 1-3 -alkyloxy-C 2-3 -alkyl, carboxy-C 1-3 -alkyl, C 1-5 -alkyloxycarbonyl-C 1-3 -alkyl, amino-C 2-3 -alkyl, C 1-3 -alkylamino-C 2-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 2-3 -alkyl, aminocarbonyl-C 1-3 -alkyl, C 1-3 -alkylaminocarbonyl-C 1-3 -alkyl, di-(C 1-3 -alkyl)-aminocarbonyl-C 1-3 -alkyl group, 
 
       a phenyl or heteroaryl, phenyl-C 1-3 -alkyl or heteroaryl-C 1-3 -alkyl group which is optionally substituted by a chlorine atom, a hydroxy, C 1-4 -alkyloxy, trifluoromethoxy, carboxy or C 1-3 -alkyloxycarbonyl group, 
       a 4- to 7-membered cycloalkyleneimino-C 1-5 -alkyl group wherein
 a methylene group of the cycloalkyleneimino moiety may be replaced by an oxygen or sulphur atom, a carbonyl or sulphonyl group, or 
 a 4- to 7-membered cycloalkyl-C 1-5 -alkyl group wherein in the cyclic moiety a methylene group may be replaced by an —NH— or —N(C 1-3 -alkyl)-group and wherein a methylene group adjacent to the —NH— or —N(C 1-3 -alkyl)-group may be replaced by a carbonyl group in each case, with the proviso that a cycloalkyleneimino group as hereinbefore defined wherein two nitrogen atoms are separated from one another by precisely one —CH 2 — group are excluded, 
 
       R 5  denotes a hydrogen atom, 
       B denotes a group of formulae 
     
     
       
         
         
             
             
         
       
       wherein
 n denotes the number 1, 
 R 6  denotes a hydrogen atom or a C 1-3 -alkyl, hydroxy, amino, C 1-3 -alkylamino group, 
 R 7  denotes a hydrogen, fluorine, chlorine or bromine atom and 
 
       X 1  is N 
       X 2 , X 3  is a CH group optionally substituted by a methyl group 
       while, unless otherwise stated, the term “heteroaryl group” mentioned hereinbefore in the definitions denotes a monocyclic 5- or 6-membered heteroaryl group optionally substituted in the carbon skeleton by a C 1-3 -alkyl, carboxy, C 1-3 -alkoxy-carbonyl or C 1-3 -alkoxy-carbonylamino group, while
 the 6-membered heteroaryl group contains one, two or three nitrogen atoms and
 the 5-membered heteroaryl group contains one or two imino groups optionally substituted by a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group, an oxygen or sulphur atom or 
 an imino group optionally substituted by a C 1-3 -alkyl, amino-C 2-3 -alkyl, C 1-3 -alkylamino-C 2-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 2-3 -alkyl, a 4- to 7-membered cycloalkyleneimino-C 1-3 -alkyl or phenyl-C 1-3 -alkyl group or an oxygen or sulphur atom and additionally a nitrogen atom or 
 an imino group optionally substituted by a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group and two or three nitrogen atoms, 
 and moreover a phenyl ring may be fused to the above-mentioned monocyclic heteroaryl groups via two adjacent carbon atoms 
 and the bond is effected via a nitrogen atom or a carbon atom of the heterocyclic moiety or a fused-on phenyl ring, 
 
 
       while the alkyl and alkoxy groups contained in the foregoing definitions, which have more than two carbon atoms, unless otherwise stated, may be straight-chain or branched and the alkyl groups in the previously mentioned dialkylated groups, for example the dialkylamino groups, may be identical or different, 
       and the hydrogen atoms of the methyl or ethyl groups contained in the foregoing definitions may be wholly or partly replaced by fluorine atoms, 
       the tautomer, the enantiomer, the diastereomer, mixtures thereof and the salt thereof. 
     
   
   
       3 . The substituted nitrogen-containing heterobicyclic compound of formula I according to  claim 1 , wherein
 R 1  denotes an amino, C 1-5 -alkylamino, C 3-7 -cycloalkylamino or (phenyl-C 1-3 -alkyl)-amino group which may in each case additionally be substituted at the amino nitrogen atom by a C 1-5 -alkyl or C 1-5 -alkylcarbonyl group optionally substituted in the alkyl moiety by a hydroxy, C 1-3 -alkoxy or carboxy group, a group which may be converted in vivo into a carboxy group, an amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino or a 4- to 7-membered cycloalkyleneimino group, while in the substitution of the previously mentioned C 1-5 -alkyl group two heteroatoms are separated from one another by at least two carbon atoms,   a 4- to 7-membered cycloalkyleneiminocarbonyl or cycloalkyleneiminosulphonyl group, while
 the cycloalkyleneimino moiety in the carbon skeleton may be substituted by one or two C 1-3 -alkyl, phenyl-C 1-3 -alkyl, 1,1-diphenyl-C 1-3 -alkyl, hydroxy-C 1-3 -alkyl, C 1-3 -alkyloxy-C 1-3 -alkyl, carboxy-C 1-3 -alkyl, C 1-3 -alkyloxycarbonyl-C 1-3 -alkyl, amino-C 1-5 -alkyl, C 1-5 -alkylamino-C 1-5 -alkyl, C 3-6 -cycloalkylamino-C 1-3 -alkyl, phenylamino-C 1-3 -alkyl, di-(C 1-5 -alkyl)-amino-C 1-5 -alkyl, N—(C 3-6-cyc loalkyl)-C 1-3 -alkylamino-C 1-3 -alkyl, a 4- to 7-membered cycloalkyleneimino-C 1-5 -alkyl, N—C 1-3 -alkylpiperazin-4-yl-C 1-3 -alkyl, N-(heteroaryl-C 1-3 -alkyl)-C 1-3 -alkylamino-C 1-3 -alkyl, C 1-3 -alkylcarbonylamino-C 1-3 -alkyl, C 1-3 -alkylsulphonylamino-C 1-3 -alkyl, C 1-5 -alkyloxycarbonylamino-C 1-3 -alkyl, C 1-3 -alkylcarbonyl, carboxy, C 1-3 -alkyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl, di-(C 1-3 -alkyl)-aminocarbonyl, hydroxy, C 1-3 -alkyloxy, benzyloxy, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, a 4- to 7-membered cycloalkyleneimino, a phenyl or a 5- to 6-membered heteroaryl group, with the proviso that in the substitution of a methylene group adjacent to the imino group two heteroatoms are separated from each other by at least two carbon atoms, and/or 
 a methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be replaced by a sulphur atom, a sulphinyl or sulphonyl group or 
 a methylene group in the 2 position of a 5-membered cycloalkyleneimino group may be replaced by an —NH— group or 
 a methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, a methylidene, carbonyl, sulphinyl or sulphonyl group or by an —NH— group optionally substituted by a C 1-3 -alkyl, hydroxy, formyl, C 1-3 -alkylcarbonyl or phenylcarbonylamino group, while additionally a methylene group adjacent to a previously mentioned —NH— group may be replaced by a carbonyl or sulphonyl group, with the proviso that
 in the substitution of the previously mentioned 6- to 7-membered cycloalkyleneimino groups, wherein a methylene group is replaced by an oxygen or sulphur atom, a sulphinyl or sulphonyl group, two heteroatoms are separated from one another by at least two carbon atoms, and/or 
 
 a —CH 2 —CH 2 — group in a 5- to 6-membered cycloalkyleneimino group may be replaced by a —NH—CO—, —CO—NH—, —CO—N(CH 3 )— or a —N(CH 3 )—CO— group with the proviso that
 a cycloalkyleneimino group as hereinbefore defined wherein two nitrogen atoms are separated from one another by precisely one —CH 2 — group is excluded, 
 
   a 5- to 7-membered cycloalkenyleneiminocarbonyl group optionally substituted by one or two C 1-3 -alkyl, amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl, 5- to 6-membered cycloalkyleneimino-C 1-3 -alkyl or C 3-6 -cycloalkylamino-C 1-3 -alkyl groups, while the double bond is not bound to a nitrogen atom and may be fused to a 5- or 6-membered heteroaryl group,   an aminocarbonyl group optionally substituted by one or two C 1-5 -alkyl, C 3-6 -cycloalkyl, 5- to 7-membered cycloalkyleneimino or piperidinyl groups,
 while the substituents may be identical or different and 
 in each case one of the previously mentioned C 1-5 -alkyl groups may be substituted by one or two hydroxy-C 1-3 -alkyl, C 1-3 -alkoxy-C 1-3 -alkyl, benzyloxy-C 1-3 -alkyl, amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl, 4- to 7-membered cyclo-alkyleneimino-C 1-3 -alkyl, C-pyrrolidinyl, C 3-6 -cycloalkylamino-C 1-3 -alkyl or 4- to 7-membered cycloalkyleneiminocarbonyl groups, while
 the cycloalkyleneimino groups previously mentioned in the groups may additionally be substituted by a carboxy or C 1-5 -alkyloxycarbonyl group, 
 
   or a group of formula   
     
       
         
         
             
             
         
       
       wherein
 m denotes the number 1, 2 or 3, 
 
       R 2  denotes a chlorine or bromine atom, a C 1-3 -alkyloxy or C 1-3 -alkyl group wherein the hydrogen atoms may be wholly or partly replaced by fluorine atoms, 
       R 3  denotes a hydrogen atom, 
       R 4  denotes a hydrogen atom or a straight-chain or branched C 1-5 -alkyl group which is optionally substituted by a C 2-3 -alkenyl, C 2-3 -alkynyl, hydroxy, C 1-5 -alkyloxy, phenyloxy, heteroaryloxy, benzyloxy, C 1-5 -alkylcarbonyloxy, carboxy-C 1-3 -alkyloxy, C 1-5 -alkyloxycarbonyl-C 1-3 -alkyloxy, C 1-8 -alkyloxycarbonylamino, mercapto, C 1-3 -alkylsulphanyl, C 1-3 -alkylsulphinyl, C 1-3 -alkylsulphonyl, carboxy, C 1-5 -alkyloxycarbonyl, allyloxycarbonyl, propargyloxycarbonyl, benzyloxycarbonyl, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, a 4- to 7-membered cycloalkyleneimino, C 1-5 -alkylcarbonylamino, C 1-3 -alkylsulphonylamino, C 3-6 -cycloalkylcarbonylamino, benzyloxycarbonylamino or phenylcarbonylamino group, 
       a group of general formula 
     
     
       
         
         
             
             
         
       
       wherein
 o denotes one of the numbers 1, 2 or 3, 
 p denotes one of the numbers 0, 1, 2 or 3, 
 R 11  denotes a hydrogen atom or a C 1-3 -alkyl group and 
 A denotes a C 3-7 -cycloalkyl group wherein
 the methyne group in the 1 position may be replaced by a nitrogen atom, if p denotes one of the numbers 2 or 3, and/or 
 a methylene group of a previously mentioned cycloalkyl group may be replaced by an oxygen or sulphur atom, a —NH—, —N(OH)—, —N(C 1-3 -alkyl)-, —N(C 1-3 -alkylcarbonyl)- or —N(heteroaryl)-group, with the proviso that in a —N(R 11 )—(CH 2 ) p -A-group thus formed two heteroatoms are separated from one another by at least two carbon atoms, and/or 
 a methylene group adjacent to a —NH—, —N(OH)—, —N(C 1-3 -alkyl)-, —N(C 1-3 -alkylcarbonyl)- or —N(heteroaryl)-group may be replaced by a carbonyl, sulphinyl or sulphonyl group, 
 
 
       a 4- to 7-membered cycloalkyleneiminocarbonyl-C 1-5 -alkyl group, while
 a methylene group of the cycloalkyleneimino moiety may be substituted by a C 1-3 -alkyl group optionally substituted by a hydroxy, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, a 4- to 7-membered cycloalkyleneimino, morpholino, piperazinyl, N—(C 1-3 -alkyl)-piperazinyl or C 1-5 -alkyloxycarbonylamino group and a methylene group of the cycloalkyleneimino moiety not adjacent to the imino group may be substituted by a hydroxy, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, aminocarbonyl, C 1-3 -alkylaminocarbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group and/or 
 a methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be replaced by a sulphur atom, a carbonyl, sulphinyl or sulphonyl group or 
 a methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a carbonyl, sulphinyl, sulphonyl or by an —NH— group optionally substituted by a C 1-3 -alkyl or heteroaryl group and additionally a methylene group adjacent to an above-mentioned —NH— or —N(C 1-3 -alkyl)-group may be replaced by a carbonyl group and/or 
 two geminal hydrogen atoms of a methylene group in a previously mentioned cycloalkyleneimino group may be substituted by a 5- to 7-membered carbocycle forming a spiro compound, while one or two methylene groups of the aforementioned carbocycle which are not adjacent to one another may be replaced independently of one another by an oxygen or sulphur atom or an —NH—, —N(OH)—, or —N(C 1-3 -alkyl)-group and additionally a methylene group of the carbocyclic group adjacent to an —NH—, —N(OH)—, or —N(C 1-3 -alkyl)-group may be replaced by a carbonyl, sulphinyl or sulphonyl group, or 
 a phenyl or heteroaryl group may be fused to two adjacent methylene groups in the 2 and 3 position of a previously mentioned 5-membered cycloalkyleneimino group or in the 3 and 4 position of a previously mentioned 6- to 7-membered cycloalkyleneimino group, 
 
       an aminocarbonyl-C 1-5 -alkyl, aminosulphonyl-C 1-3 -alkyl, C 1-3 -alkylaminocarbonyl-C 1-5 -alkyl or C 1-3 -alkylaminosulphonyl-C 1-3 -alkyl group, while
 the previously mentioned amino groups may additionally be substituted by a C 3-6 -cycloalkyl-C 1-3 -alkyl, phenyl-C 1-3 -alkyl, heteroaryl-C 1-3 -alkyl, heteroarylamino-C 2-3 -alkyl, hydroxy-C 2-3 -alkyl, C 1-3 -alkyloxy-C 2-3 -alkyl, carboxy-C 1-3 -alkyl, C 1-5 -alkyloxycarbonyl-C 1-3 -alkyl, amino-C 2-3 -alkyl, C 1-3 -alkylamino-C 2-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 2-3 -alkyl, aminocarbonyl-C 1-3 -alkyl, C 1-3 -alkylaminocarbonyl-C 1-3 -alkyl, di-(C 1-3 -alkyl)-aminocarbonyl-C 1-3 -alkyl group, 
 
       a phenyl or heteroaryl, phenyl-C 1-3 -alkyl or heteroaryl-C 1-3 -alkyl group which is optionally substituted by a chlorine atom, a hydroxy, C 1-4 -alkyloxy, carboxy or C 1-3 -alkyloxycarbonyl group, 
       a 4- to 7-membered cycloalkyleneimino-C 1-3 -alkyl group wherein
 a methylene group of the cycloalkyleneimino moiety may be replaced by an oxygen or sulphur atom, a carbonyl or sulphonyl group, or 
 
       a 4- to 7-membered cycloalkyl-C 1-3 -alkyl group wherein in the cyclic moiety a methylene group may be replaced by an —NH— or —N(C 1-3 -alkyl)-group and wherein a methylene group adjacent to the —NH— or —N(C 1-3 -alkyl)-group may be replaced in each case by a carbonyl group, with the proviso that a cycloalkyleneimino group as hereinbefore defined wherein two nitrogen atoms are separated from one another by precisely one —CH 2 — group are excluded, 
       R 5  denotes a hydrogen atom, 
       B denotes a group of formulae 
     
     
       
         
         
             
             
         
       
       wherein
 n denotes the number 1, 
 R 6  denotes a hydrogen atom, 
 R 7  denotes a fluorine, chlorine or bromine atom, and 
 
       X 1  is N 
       X 2 , X 3  is a CH group 
       while, unless otherwise stated, the term “heteroaryl group” mentioned hereinbefore in the definitions refers to a monocyclic 5- or 6-membered heteroaryl group optionally substituted in the carbon skeleton by a C 1-3 -alkyl group, while
 the 6-membered heteroaryl group contains one, two or three nitrogen atoms and
 the 5-membered heteroaryl group contains one or two imino groups optionally substituted by a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group or a sulphur atom or 
 an imino group optionally substituted by a C 1-3 -alkyl, amino-C 2-3 -alkyl, C 1-3 -alkylamino-C 2-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 2-3 -alkyl or phenyl-C 1-3 -alkyl group or a sulphur atom and additionally a nitrogen atom or 
 an imino group optionally substituted by a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group and two or three nitrogen atoms, 
 and moreover a phenyl ring may be fused to the above-mentioned monocyclic heteroaryl groups via two adjacent carbon atoms 
 and the bond is effected via a nitrogen atom or a carbon atom of the heterocyclic moiety or a fused-on phenyl ring, 
 
 
       while, unless otherwise stated, the alkyl and alkoxy groups contained in the foregoing definitions which have more than two carbon atoms may be straight-chain or branched and the alkyl groups in the previously mentioned dialkylated groups, for example the dialkylamino group, may be identical or different, 
       and the hydrogen atoms of the methyl or ethyl groups contained in the foregoing definitions may be wholly or partly replaced by fluorine atoms, 
       the tautomer, the enantiomer, the diastereomer, mixtures thereof and the salt thereof. 
     
   
   
       4 . The substituted nitrogen-containing heterobicyclic compound of formula I according to  claim 1 , wherein
 R 1  denotes a 4- to 7-membered cycloalkyleneiminocarbonyl group, while
 the cycloalkyleneimino moiety in the carbon skeleton may be substituted by one or two C 1-3 -alkyl, phenyl-C 1-3 -alkyl, 1,1-diphenyl-C 1-3 -alkyl, hydroxy-C 1-3 -alkyl, C 1-3 -alkyloxy-C 1-3 -alkyl, carboxy-C 1-3 -alkyl, C 1-3 -alkyloxycarbonyl-C 1-3 -alkyl, amino-C 1-5 -alkyl, C 1-5 -alkylamino-C 1-5 -alkyl, C 3-6 -cycloalkylamino-C 1-3 -alkyl, phenylamino-C 1-3 -alkyl, di-(C 1-5 -alkyl)-amino-C 1-5 -alkyl, N—(C 3-6-cyc loalkyl)-C 1-3 -alkylamino-C 1-3 -alkyl, a 4- to 7-membered cycloalkyleneimino-C 1-5 -alkyl, N—C 1-3 -alkylpiperazin-4-yl-C 1-3 -alkyl, N-(piperidin-2-yl-C 1-3 -alkyl)-C 1-3 -alkylamino-C 1-3 -alkyl, C 1-3 -alkylcarbonylamino-C 1-3 -alkyl, C 1-3 -alkylsulphonylamino-C 1-3 -alkyl, C 1-5 -alkyloxycarbonylamino-C 1-3 -alkyl, C 1-3 -alkylcarbonyl, carboxy, C 1-5 -alkyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, C 1-3 -alkylamino-carbonyl, di-(C 1-3 -alkyl)-aminocarbonyl, hydroxy, C 1-3 -alkyloxy, benzyloxy, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, a 4- to 7-membered cycloalkyleneimino, a phenyl or a 5- to 6-membered heteroaryl group, with the proviso that in the substitution of a methylene group adjacent to the imino group two heteroatoms are separated from one another by at least two carbon atoms, and/or 
 a methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be replaced by a sulphur atom, a sulphinyl or sulphonyl group or 
 a methylene group in the 2 position of a 5-membered cycloalkyleneimino group may be replaced by an —NH— group or 
 a methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, a methylidene, carbonyl, sulphinyl or sulphonyl group or by an —NH— group optionally substituted by a C 1-3 -alkyl, hydroxy, formyl, C 1-3 -alkylcarbonyl or phenylcarbonylamino group, while additionally a methylene group adjacent to a previously mentioned —NH— group may be replaced by a carbonyl or sulphonyl group, with the proviso that
 in the substitution of the previously mentioned 6- to 7-membered cycloalkyleneimino groups, wherein a methylene group is replaced by an oxygen or sulphur atom, a sulphinyl or sulphonyl group, two heteroatoms are separated from one another by at least two carbon atoms, and/or 
 
 a —CH 2 —CH 2 — group in a 5- to 6-membered cycloalkyleneimino group may be replaced by an —NH—CO—, —CO—NH—, —CO—N(CH 3 )— or a —N(CH 3 )—CO— group, with the proviso that
 a cycloalkyleneimino group as hereinbefore defined wherein two nitrogen atoms are separated from one another by precisely one —CH 2 — group is excluded, 
 
   a 5- to 7-membered cycloalkenyleneiminocarbonyl group optionally substituted by one or two C 1-3 -alkyl, amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl, 5- to 6-membered cycloalkyleneimino-C 1-3 -alkyl or C 3-6 -cycloalkylamino-C 1-3 -alkyl groups, while the double bond is not bound to a nitrogen atom and may be fused to a 5- or 6-membered heteroaryl group,   an aminocarbonyl group optionally substituted by one or two C 1-5 -alkyl, C 3-6 -cycloalkyl, 5- to 7-membered cycloalkyleneimino or piperidinyl groups,
 while the substituents may be identical or different and 
 in each case one of the previously mentioned C 1-5 -alkyl groups may be substituted by one or two amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl, 4- to 7-membered cycloalkyleneimino-C 1-3 -alkyl, C-pyrrolidinyl, C 3-6 -cycloalkylamino-C 1-3 -alkyl or 4- to 7-membered cycloalkyleneiminocarbonyl groups, while
 the cycloalkyleneimino groups previously mentioned in the groups may additionally be substituted by a carboxy or C 1-5 -alkyloxycarbonyl group, 
 
   or a group of formula   
     
       
         
         
             
             
         
       
       wherein
 m denotes the number 1, 2 or 3, 
 
       R 3  denotes a chlorine or bromine atom, a C 1-3 -alkyloxy or C 1-3 -alkyl group wherein the hydrogen atoms may be wholly or partly replaced by fluorine atoms, 
       R 3  denotes a hydrogen atom, 
       R 4  denotes a hydrogen atom or a straight-chain or branched C 1-5 -alkyl group which is optionally substituted by a C 2-3 -alkynyl, hydroxy, C 1-5 -alkyloxy, benzyloxy, C 1-5 -alkylcarbonyloxy, carboxy-C 1-3 -alkyloxy, C 1-5 -alkyloxycarbonyl-C 1-3 -alkyloxy, C 1-3 -alkylsulphanyl, C 1-3 -alkylsulphinyl, C 1-3 -alkylsulphonyl, carboxy, C 1-5 -alkyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, a 4- to 7-membered cycloalkyleneimino, C 1-5 -alkylcarbonylamino, C 1-3 -alkylsulphonylamino, C 3-6 -cycloalkylcarbonylamino, benzyloxycarbonylamino or phenylcarbonylamino group, 
       a group of general formula 
     
     
       
         
         
             
             
         
       
       wherein
 o denotes one of the numbers 1, 2 or 3, 
 p denotes one of the numbers 0, 1, 2 or 3, 
 R 11  denotes a hydrogen atom or a C 1-3 -alkyl group and 
 A denotes a C 3-7 -cycloalkyl group wherein
 the methyne group in the 1 position may be replaced by a nitrogen atom, if p denotes one of the numbers 2 or 3, and/or 
 a methylene group of a previously mentioned cycloalkyl group may be replaced by an oxygen or sulphur atom, a —NH—, —N(OH)—, —N(C 1-3 -alkyl)-, —N(C 1-3 -alkylcarbonyl)- or —N(heteroaryl)-group, with the proviso that in a group —N(R 11 )—(CH 2 ) p -A- thus formed two heteroatoms are separated from one another by at least two carbon atoms, and/or 
 a methylene group adjacent to an —NH—, —N(OH)—, —N(C 1-3 -alkyl)-, —N(C 1-3 -alkylcarbonyl)- or —N(heteroaryl)-group may be replaced by a carbonyl, sulphinyl or sulphonyl group, 
 
 
       a 5- to 6-membered cycloalkyleneiminocarbonyl-C 1-5 -alkyl group, while
 a methylene group of the cycloalkyleneimino moiety may be substituted by a C 1-3 -alkyl group optionally substituted by a hydroxy, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, a 4- to 7-membered cycloalkyleneimino, morpholino, piperazinyl, N—(C 1-3 -alkyl)-piperazinyl or C 1-5 -alkyloxycarbonylamino group and a methylene group of the cycloalkyleneimino moiety not adjacent to the imino group may be substituted by a hydroxy, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, aminocarbonyl, C 1-3 -alkylaminocarbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group and/or 
 a methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be replaced by a sulphur atom, a carbonyl, sulphinyl or sulphonyl group or 
 a methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a carbonyl, sulphinyl, sulphonyl or by a-NH-group optionally substituted by a C 1-3 -alkyl or heteroaryl group and additionally a methylene group adjacent to an above-mentioned —NH— or —N(C 1-3 -alkyl)-group may be replaced by a carbonyl group and/or 
 two geminal hydrogen atoms of a methylene group in a previously mentioned cycloalkyleneimino group may be substituted by a 5- to 7-membered carbocycle forming a spiro compound, while one or two methylene groups of the aforementioned carbocycle which are not adjacent to one another may be replaced independently of one another by an oxygen or sulphur atom or an —NH—, —N(OH)—, or —N(C 1-3 -alkyl)-group and additionally a methylene group of the carbocyclic group adjacent to an —NH—, —N(OH)—, or —N(C 1-3 -alkyl)-group may be replaced by a carbonyl, sulphinyl or sulphonyl group, or 
 a phenyl or heteroaryl group may be fused to two adjacent methylene groups in the 2 and 3 position of a previously mentioned 5-membered cycloalkyleneimino group or in the 3 and 4 position of a previously mentioned 6- to 7-membered cycloalkyleneimino group, 
 
       an aminocarbonyl-C 1-5 -alkyl or C 1-3 -alkylaminocarbonyl-C 1-5 -alkyl group, while
 the previously mentioned amino groups may additionally be substituted by a C 3-6 -cycloalkyl-C 1-3 -alkyl, phenyl-C 1-3 -alkyl, heteroaryl-C 1-3 -alkyl, heteroarylamino-C 2-3 -alkyl, hydroxy-C 2-3 -alkyl, C 1-3 -alkyloxy-C 2-3 -alkyl, carboxy-C 1-3 -alkyl, C 1-5 -alkyloxycarbonyl-C 1-3 -alkyl, amino-C 2-3 -alkyl, C 1-3 -alkylamino-C 2-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 2-3 -alkyl, aminocarbonyl-C 1-3 -alkyl, C 1-3 -alkylaminocarbonyl-C 1-3 -alkyl, di-(C 1-3 -alkyl)-aminocarbonyl-C 1-3 -alkyl group, 
 
       a phenyl or heteroaryl, phenyl-C 1-3 -alkyl or heteroaryl-C 1-3 -alkyl group which is optionally substituted by a chlorine atom, a hydroxy, C 1-4 -alkyloxy, trifluoromethoxy, carboxy or C 1-3 -alkyloxycarbonyl group, 
       a 4- to 7-membered cycloalkyleneimino-C 1-5 -alkyl group wherein
 a methylene group of the cycloalkyleneimino moiety may be replaced by an oxygen or sulphur atom, a carbonyl or sulphonyl group, 
 
       R 5  denotes a hydrogen atom, 
       B denotes a group of formulae 
     
     
       
         
         
             
             
         
       
       wherein
 n denotes the number 1, 
 R 6  denotes a hydrogen atom, 
 R 7  denotes a chlorine or bromine atom and 
 
       X 1  is N 
       X 2 , X 3  is a CH group 
       while, unless otherwise stated, the term “heteroaryl group” mentioned hereinbefore in the definitions denotes a monocyclic 5- or 6-membered heteroaryl group optionally substituted in the carbon skeleton by a C 1-3 -alkyl group, while
 the 6-membered heteroaryl group contains one, two or three nitrogen atoms and
 the 5-membered heteroaryl group contains one or two imino groups optionally substituted by a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group or a sulphur atom or 
 an imino group optionally substituted by a C 1-3 -alkyl, amino-C 2-3 -alkyl, C 1-3 -alkylamino-C 2-3 -alkyl, di-(C 1-3 -alkyl)-amino-C 2-3 -alkyl or phenyl-C 1-3 -alkyl group or a sulphur atom and additionally a nitrogen atom or 
 an imino group optionally substituted by a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group and two or three nitrogen atoms, 
 and moreover a phenyl ring may be fused to the above-mentioned monocyclic heteroaryl groups via two adjacent carbon atoms 
 and the bond is effected via a nitrogen atom or a carbon atom of the heterocyclic moiety or a fused-on phenyl ring, 
 
 
       while, unless otherwise stated, the alkyl and alkoxy groups contained in the foregoing definitions which have more than two carbon atoms may be straight-chain or branched and the alkyl groups in the previously mentioned dialkylated groups, for example the dialkylamino groups, may be identical or different, 
       and the hydrogen atoms of the methyl or ethyl groups contained in the foregoing definitions may be wholly or partly replaced by fluorine atoms, 
       the tautomer, the enantiomer, the diastereomer, mixtures thereof and the salt thereof. 
     
   
   
       5 . The substituted nitrogen-containing heterobicyclic compound of formula I according to  claim 1 , wherein
 R 1  denotes a 2,5-dihydro-1H-pyrrol-1-yl-carbonyl, pyrrolidin-1-yl-carbonyl, 2-(aminomethyl)-pyrrolidin-1-yl-carbonyl, 2-(N-tert.-butyloxycarbonylaminomethyl)-pyrrolidin-1-yl-carbonyl, 3-oxo-piperazin-1-yl-carbonyl, morpholin-4-yl-carbonyl, carboxy, 3-aminomethyl-pyrrolidin-1-yl-carbonyl, thiazolidin-3-yl-carbonyl, 3-aminomethyl-pyrrolidin-1-yl-carbonyl, pyrazolidin-3-on-1-yl-carbonyl, pyrrolidin-2-ylmethylamino-carbonyl, 1-tert.-butyloxycarbonyl-pyrrolidin-2-yl-methylamino-carbonyl, 2-(acetylamino-methyl)-pyrrolidin-1-yl-carbonyl, 2-(pyrrolidin-1-yl-methyl)-pyrrolidin-1-yl-carbonyl, 2-(tert.-butyloxycarbonyl-aminomethyl)-thiazolidin-1-yl-carbonyl, 2-(pyridin-4-yl)-pyrrolidin-1-yl-carbonyl, 2-aminomethyl-thiazolidinyl-carbonyl, 2-(methanesulphonyl-aminomethyl)-pyrrolidin-1-yl-carbonyl, 2-acetaminomethyl-thiazolidin-1-yl-carbonyl, 5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3a]pyridin-4-yl, 2-(pyridin-4-yl)-thiazolidin-3-yl-carbonyl, 2-(2,2,2-trifluorethyl)-thiazolidin-3-yl-carbonyl, 2-(2-aminoethyl)-pyrrolidin-1-yl-carbonyl, 2-ethoxycarbonyl-piperidin-1-yl-carbonyl, 4,5,6,7-tetrahydro-thieno[3,2-c]pyridin-5-yl-carbonyl, 2-benzhydryl-pyrrolidin-1-yl-carbonyl, [1,4]diazepan-1-yl-carbonyl, 2-(2-ethoxycarbonyl-ethyl)-piperidin-1-yl-carbonyl, 2-methylaminocarbonyl-pyrrolidin-1-yl-carbonyl, 3-(3-diethylamino-propyl)-piperidin-1-yl-carbonyl, 4-methyl-piperidin-1-yl-carbonyl, 2-(phenylaminomethyl)-pyrrolidin-1-yl-carbonyl, 2-benzyl-pyrrolidin-1-yl-carbonyl, 3-hydroxy-piperidin-1-yl-carbonyl, 2-dimethylaminocarbonyl-pyrrolidin-1-yl-carbonyl, piperidin-1-yl-carbonyl, 4-oxo-piperidin-1-yl-carbonyl, 4-methylene-piperidin-1-yl-carbonyl, 2-methyl-piperidin-1-yl-carbonyl, 2-benzyloxycarbonyl-pyrrolidin-1-yl-carbonyl, N-(3-amino-propyl)-N-ethyl-amino-carbonyl, N-cyclopropyl-N-methylamino-carbonyl, 2-methoxymethyl-pyrrolidin-1-yl-carbonyl, 3-(1H-benzimidazol-2-yl)-piperidin-1-yl]-carbonyl, 3-dimethylamino-pyrrolidin-1-yl-carbonyl, 2,5-dimethyl-2,5-dihydro-1H-pyrrol-1-yl)-carbonyl, 2-isopropyl-pyrrolidin-1-yl-carbonyl, 2-aminomethyl-piperidin-1-yl-carbonyl], 3-aminomethyl-piperidin-1-yl-carbonyl, 2-ethoxycarbonyl-pyrrolidin-1-yl-carbonyl, 3-(dimethylamino-methyl)-piperidin-1-yl-carbonyl, 2-(2-phenyl-ethyl)-pyrrolidin-1-yl-carbonyl, 2-(pyridin-2-yl)-pyrrolidin-1-yl-carbonyl, 2-(2-amino-ethyl)-piperidin-1-yl-carbonyl, 4-acetyl-piperazin-1-yl-carbonyl, N-(2-amino-ethyl)-N-ethyl-amino-carbonyl, 2-(pyridin-3-yl)-piperidin-1-yl-carbonyl, 2,5-dimethyl-pyrrolidin-1-yl-carbonyl, 4-aminocarbonyl-piperidin-1-yl-carbonyl, 4-hydroxy-piperidin-1-yl-carbonyl, 2-ethoxycarbonyl-piperidin-1-yl-carbonyl, 1-(1,4,6,7-tetrahydro-pyrazolo[4,3]pyridin-5-yl)-carbonyl, 2,5-dimethoxymethyl-pyrrolidin-1-yl-carbonyl, 2-methoxycarbonyl-pyrrolidin-1-yl-carbonyl, pyrazolidin-1-yl-carbonyl, 1-oxo-thiomorpholin-4-yl-carbonyl, 2-[(N-butyl-N-ethyl-amino)-methyl]-piperidin-1-yl-carbonyl, N-ethyl-N-(piperidin-4-yl)-aminocarbonyl, 4-formyl-piperazin-1-yl-carbonyl, 2-(2-dimethylamino-ethyl)-piperidin-1-yl-carbonyl, 2-(2-diethylamino-ethyl)-piperidin-1-yl-carbonyl, 1,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl-carbonyl, 3,6-dihydro-2H-pyridin-1-yl-carbonyl, 2-[(N-butyl-N-methyl-amino)-methyl]-piperidin-1-yl-carbonyl, 2-methyl-morpholin-4-yl-carbonyl, thiomorpholin-4-yl-carbonyl, 2-(2-amino-ethyl)-piperidin-1-yl-carbonyl, 2-ethyl-piperidin-1-yl-carbonyl, 3-amino-pyrrolidin-1-yl-carbonyl, 4-trifluoromethyl-piperidin-1-yl-carbonyl, 3-[4-(pyrrolidin-1-yl)-butyl]-pyrrolidin-1-yl-carbonyl, 2-[(N-methyl-N-(pyridin-2-ylmethyl)-amino)-methyl]-piperidin-1-yl-carbonyl, 4-hydroxy-piperazin-1-yl-carbonyl, 3-(pyrrolidin-1-ylmethyl)-piperidin-1-yl-carbonyl, 2-diethylaminomethyl-piperidin-1-yl-carbonyl, 2-(4-diethylamino-butyl)-piperidin-1-yl-carbonyl, 2-hydroxymethyl-pyrrolidin-1-yl-carbonyl, 2-(N-ethyl-N-methyl-aminomethyl)-piperidin-1-yl-carbonyl, 2-aminocarbonyl-pyrrolidin-1-yl-carbonyl, 2-(4-methyl-piperazin-1-ylmethyl)-piperidin-1-yl-carbonyl, 2-methoxymethyl-pyrrolidin-1-yl-carbonyl, 2-(3-dimethylamino-propyl)-piperidin-1-yl-carbonyl, 2-diethylaminocarbonyl-piperidin-1-yl-carbonyl, 2-[(N-cyclo-hexyl-N-methyl-amino)-methyl]-piperidin-1-yl-carbonyl, 2-piperidin-1-ylmethyl-piperidin-1-yl-carbonyl, 2-(1-methyl-1H-pyrazol-4-yl)-thiazolidinyl-carbonyl or 6,7,8,9-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-4-yl-group,   R 2  denotes a hydrogen, chlorine or bromine atom, a C 1-3 -alkyloxy or a C 1-3 -alkyl group wherein the hydrogen atoms may be wholly or partly replaced by fluorine atoms,   R 3  denotes a hydrogen atom,   R 4  denotes a hydrogen atom, a methyl, propyl, 2-methylsulphanyl-ethyl, 2-methylsulphonyl-ethyl, hydroxymethyl, 2-carboxyethyl, 2-benzyloxycarbonyl-ethyl, 2-methoxy-ethyl, 2-methylsulphinyl-ethyl, tert.-butyloxycarbonylmethoxy-methyl, 2-ethoxycarbonyl-ethyl, carboxymethoxy-methyl, o-chlorophenyl, p-chlorophenyl, methoxymethyl, 2-diethyl-aminocarbonyl-ethyl, 2-propargyloxycarbonyl-ethyl, 2-(pyrrolidin-1-yl-carbonyl)-ethyl, 2-[N-methyl-N-piperidin-4-yl-amino]-carbonyl-ethyl, 2-[4-methyl-piperazin-1-yl]-carbonyl-ethyl, 2-(C-piperidin-4-yl-methylamino)-carbonyl-ethyl, 2-(N-benzyl-N-methyl-amino)-carbonyl-ethyl, 3-tert.-butyloxycarbonyl-propyl, 2-benzyloxycarbonylamino-ethyl, 2-[(1,2,3,4-tetrahydroisoquinolin-1-yl)-carbonyl-ethyl, 2-(benzylamino-carbonyl)-ethyl, 2-[(N-methyl-N-phenethyl-amino-carbonyl)-ethyl, 2-(hydroxyethylamino-carbonyl)-ethyl, 2-[(C-pyridin-3-yl-methylamino-carbonyl)-propyl, 2-[(1-oxa-3,8-diaza-spiro[4.5]decan-2-on-8-yl)-carbonyl]-ethyl, 2-(morpholin-4-yl-carbonyl)-ethyl, 2-(C-cyclohexyl-methylamino-carbonyl)-ethyl, 2-(methoxyethylamino-carbonyl)-ethyl, 2-(dimethylaminoethyl-amino-carbonyl)-ethyl, 2-(cyclopropylamino-carbonyl)-ethyl, 2-[C-2-tetrahydrofuran-2-yl-methylamino-carbonyl)-ethyl, 2-(dimethylaminopropylamino-carbonyl)-ethyl, 2-(aminoethylamino-carbonyl)-ethyl, 2-(hydroxycarbonylmethyl-methyl-amino-carbonyl)-ethyl, 2-((3-(pyrrolidin-2-on-1-yl)-propyl)-amino-carbonyl)-ethyl, 2-[(1-[1,3,5]triazin-2-yl-piperidin-4-ylamino)-carbonyl]-ethyl, 2-[(2-imidazol-1-yl-ethylamino)-carbonyl)-ethyl, 2-[C-(1H-imidazol-2-yl)-methylamino-carbonyl)-ethyl, 2-(2,2,2-trifluoroethylamino-carbonyl)-ethyl, 2-[N-(2-dimethylamino-ethyl)-N-methyl-amino-carbonyl]-ethyl, 2-[1-phenyl-ethylamino-carbonyl]-ethyl, 2-[2-(4-methyl-piperazin-1-ylmethyl)-piperidin-1-yl-carbonyl]-ethyl, 2-(N-aminocarbonylmethyl-N-methyl-amino-carbonyl)-ethyl, 2-(4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-5-yl-carbonyl)-ethyl, 2-(1-oxo-thiomorpholin-4-yl-carbonyl)-ethyl, 2-(N-dimethylaminocarbonylmethyl-N-methyl-amino-carbonyl)-ethyl, 2-(N-hydroxycarbonylethyl-N-methyl-amino-carbonyl)-ethyl, 2-[C-(1-methyl-1H-imidazol-2-yl)-methylamino-carbonyl)-ethyl, 2-(N-piperidin-2-yl-aminocarbonyl)-ethyl, 2-[C-(tetrahydropyran-4-yl)-methylamino-carbonyl]-ethyl, 2-(4-hydroxypiperidin-1-yl-carbonyl)-ethyl, 2-[C-(pyridin-4-yl)-methylamino-carbonyl]-ethyl, 2-(N-methylaminocarbonylmethyl-N-methyl-amino-carbonyl)-ethyl, 2-[N-(2-(1H)-imidazol-4-yl)-ethyl)-N-methyl-amino-carbonyl]-ethyl, 2-(1-thiazolidin-3-yl-carbonyl)-ethyl, 2-(N-cyclopropyl-N-methyl-amino-carbonyl)-ethyl, 2-(cyclopentylamino-carbonyl)-ethyl, 2-(N-piperidin-4-yl-aminocarbonyl)-ethyl, 2-[C-(pyridin-2-yl)-methylamino-carbonyl]-ethyl, 2-(4-thiazol-2-yl-piperazin-1-yl-carbonyl)-ethyl, 2-(piperidin-1-yl-carbonyl)-ethyl, 2-amino-ethyl, thiophen-3-yl, 2-(2-oxo-pyrrolidin-1-yl)-ethyl, 2-(1,1-dioxo-isothiazolidin-2-yl)-ethyl, isopropylcarbonyloxy-methyl, 3-carboxy-propyl, 2-methylsulphonylamino-ethyl, methylsulphanyl-methyl, benzyloxy-methyl, 2-[2-(pyridin-4-yl-amino)-ethylamino-carbonyl]-ethyl, but-3-yn-1-yl, 1-methoxy-ethyl, 1-tert.-butyloxy-ethyl or 1-hydroxy-ethyl group,   R 5  denotes a hydrogen atom,   B denotes a group of formulae   
     
       
         
         
             
             
         
       
       wherein
 R 6  denotes a hydrogen atom, 
 R 7  denotes a chlorine or bromine atom, and 
 
       X 1  is N 
       X 2 , X 3  is a CH group) 
       the tautomer, the enantiomer, the diastereomer, mixtures thereof and the salt thereof. 
     
   
   
       6 . The compound of formula I according to  claim 1  selected from the following compounds, or a tautomer, stereoisomer or salt thereof: 
     (1) 4-[(5-chloro-1H-benzimidazol-2-yl)-methylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinoline, 
     (11) 4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinoline, 
     (12) 4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulphanyl-propylamino]-6-methyl-7-(pyrrolidin-1-yl-carbonyl)-quinoline, 
     (13) 4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-6-methyl-7-(pyrrolidin-1-yl-carbonyl)-quinoline, 
     (14) 4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-6-methyl-7-(3-oxo-piperazin-1-yl-carbonyl)-quinoline, 
     (15) 4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-6-methyl-7-[(2R)-2-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinoline, 
     (16) 4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulphanyl-propylamino]-6-methyl-7-(3-oxo-piperazin-1-yl-carbonyl)-quinoline, and 
     (17) 4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-methanesulphonyl-propylamino]-6-methyl-7-(pyrrolidin-1-yl-carbonyl)-quinoline. 
   
   
       7 . The compound of formula I according to  claim 1  selected from the following compounds, or a 
     tautomer, stereoisomer or salt thereof: 
     (1) 4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulphanyl-propylamino]-6-methyl-7-(pyrrolidin-1-yl-carbonyl)-quinoline, 
     (2) 4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-6-methyl-7-(pyrrolidin-1-yl-carbonyl)-quinoline, 
     (3) 4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-6-methyl-7-(3-oxo-piperazin-1-yl-carbonyl)-quinoline, 
     (4) 4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-6-methyl-7-[(2R)-2-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinoline, 
     (5) 4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulphanyl-propylamino]-6-methyl-7-(3-oxo-piperazin-1-yl-carbonyl)-quinoline, and 
     (6) 4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-methanesulphonyl-propylamino]-6-methyl-7-(pyrrolidin-1-yl-carbonyl)-quinoline. 
     the tautomers, the stereoisomers and the salts thereof. 
   
   
       8 . A physiologically acceptable salt of the compound according to  claim 1 . 
   
   
       9 . A pharmaceutical composition comprising a compound according to  claim 1  together with one or more inert carriers or diluents.