D-pyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture

1. A D-pyranosyl-substituted phenyl compound of general formula I

wherein

R 1 denotes hydrogen, fluorine, chlorine, bromine, iodine, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 3-10 -cycloalkyl, C 3-10 -cycloalkyl-C 1-3 -alkyl, C 5-10 -cycloalkenyl, C 5-10 -cycloalkenyl-C 1-3 -alkyl, C 1-4 -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-3 -alkyl)aminocarbonyl, pyrrolidin-1-ylcarbonyl, piperidin-1-ylcarbonyl, morpholin-4-ylcarbonyl, piperazin-1-ylcarbonyl, 4-(C 1-4 -alkyl)piperizin-1-ylcarbonyl, C 1-4 -alkoxycarbonyl, amino, C 1-4 -alkylamino, di-(C 1-3 -alkyl)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, piperazin-1-yl, 4-(C 1-4 alkyl)piperazin-1-yl, C 1-4 -alkylcarbonylamino, C 1-6 -alkyloxy, C 3-10 -cycloalkyloxy, C 5-10 -cycloalkenyloxy, aryloxy, C 1-4 -alkylsulphanyl,C 1-4 -alkylsulphinyl, C 1-4 -alkylsulphonyl, C 3-10 -cycloalkylsulphanyl, C 3-10 cycloalkylsulphinyl, C 3-10 -cycloalkylsulphonyl, C 5-10 -cycloalkenylsulphanyl, C 5-10 -cycloalkenylsulphinyl, C 5-10 -cycloalkenylsulphonyl, arylsulphanyl, arylsulphinyl, arylsulphonyl, hydroxy, cyano or nitro,

while alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl groups may be partly or completely fluorinated or may be mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and in cycloalkyl and cycloalkenyl groups one or two methylene groups may be replaced independently of one another by O, S, CO, SO or SO 2 , and in N-heterocycloalkyl groups a methylene group may be replaced by CO or SO 2 , and

R 2 denotes hydrogen, fluorine, chlorine, bromine, hydroxy, C 1-4 -alkyl, C 1-4 -alkoxy, cyano or nitro, while alkyl groups may be mono- or polysubstituted by fluorine, or in the event that R 1 and R 2 are bound to two adjacent C atoms of the phenyl ring, R 1 and R 2 may be joined together such that R 1 and R 2 together form a C 3-5 -alkylene, C 3-5 -alkenylene or butadienylene bridge, which may be partly or completely fluorinated or may be mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and wherein one or two methylene groups may be replaced independently of one another by O, S, CO, SO, SO 2 or NR N , and wherein in the case of a butadienylene bridge one or two methyne groups may be replaced by an N atom,

R 3 denotes hydrogen, fluorine, chlorine, bromine, iodine, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 3-10 -cycloalkyl, C 3-10 -Cycloalkyl-C 1-3 -alkyl, C 5-10 -cycloalkenyl, C 5-10 -cycloalkenyl-C 1-3 -alkyl, aryl, heteroaryl, C 1-4 -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-3 -alkyl)aminocarbonyl, pyrrolidin-1-ylcarbonyl, piperidin-1-ylcarbonyl, morpholin-4-ylcarbonyl, piperazin-1-ylcarbonyl, 4-(C 1-4 -alkyl)piperazin-1-ylcarbonyl, hydroxycarbonyl, C 1-4 -alkoxycarbonyl, C 1-4 -alkylamino, di-(C 1-3 -alkyl)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, piperazin-1-yl, 4-(C 1-4 -alkyl)piperazin-1-yl, C 1-4 -alkylcarbonylamino, arylcarbonylamino, heteroaryl-carbonylamino, C 1-4 -alkylsulphonylamino, arylsulphonylamino, C 1-6 -alkoxy, C 3-7 -cycloalkyloxy, C 5-7 -cycloalkenyloxy, aryloxy, heteroaryloxy, C 1-4 -alkyl-sulphanyl, C 1-4 -alkyl-sulphinyl, C 1-4 -alkylsulphonyl, C 3-10 -cycloalkylsulphanyl, C 3-10 -cycloalkylsulphinyl, C 3-10 -cycloalkylsulphonyl, C 5-10 -cycloalkenylsulphanyl, C 5-10 -cycloalkenylsulphinyl, C 5-10 -cycloalkenylsulphonyl, arylsulphanyl, arylsulphinyl, arylsulphonyl, amino, hydroxy, cyano or nitro,

while alkyl, alkenyl, alkynyl, cycloalkyl- and cycloalkenyl groups may be partly or completely fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and

in cycloalkyl and cycloalkenyl groups one or two methylene groups may be replaced independently of one another by O, S, CO, SO or SO 2 , and

in N-heterocycloalkyl groups a methylene group may be substituted by CO or SO 2 , and

R 4 independently of one another denote hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C 1-3 -alkyl, C 1-3 -alkoxy or methyl or methoxy substituted by 1 to 3 fluorine atoms, or

if R 3 and R 4 are bound to two adjacent C atoms of the phenyl ring, R 3 and R 4 may be joined together such that R 3 and R 4 together form a C 3-5 -alkylene, C 3-5 -alkenylene or butadienylene bridge, which may be partly or completely fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and wherein one or two methylene groups may be replaced independently of one another by O, S, CO, SO, SO 2 or NR N , and wherein in the case of a butadienylene bridge one or two methyne groups may be replaced by an N atom,

R 5 independently of one another denote hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C 1-3 -alkyl, C 1-3 -alkoxy or methyl or methoxy substituted by 1 to 3 fluorine atoms, and

R N denotes H, C 1-4 -alkyl or C 1-4 -alkylcarbonyl,

L are selected independently of one another from among fluorine, chlorine, bromine, iodine, C 1-3 -alkyl, difluoromethyl, trifluoromethyl, C 1-3 -alkoxy, difluoromethoxy, trifluoromethoxy and cyano,

R 7a , R 7b , R 7c independently of one another have a meaning selected from among hydrogen, (C 1-18 -alkyl)carbonyl, (C 1-18 -alkyl)oxycarbonyl, arylcarbonyl and aryl-(C 1-3 -alkyl)-carbonyl,

X is hydrogen, chlorine, cyano, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 1-6 -alkylsulphonyl, hydroxycarbonyl, C 1-4 -alkoxycarbonyl, aminocarbonyl or C 1-4 alkylaminocarbonyl, while alkyl groups may be mono- or polyfluorinated or monosubstituted by hydroxy or cyano; or

X is mercapto, C 1-5 -alkylsulphanyl, C 2-5 -alkenylsulphanyl, C 2-5 -alkynylsulphanyl, C 3-7 -cycloalkylsulphanyl or arylsulphanyl; or

X is amino, C 1-5 -alkylamino, N—(C 1-5 -alkyl)-N—(C 1-3 -alkyl)-amino, C 1-4 -alkylcarbonylamino, N—(C 1-5 -alkyl)-N—(C 1-4 -alkylcarbonyl)-amino or arylamino; or

X is fluorine; or

X denotes bromine, iodine, C 1-6 -alkylsulphonyloxy, arylsulphonyloxy or aryl-C 1-3 -alkyl-sulphonyloxy,

while the above-mentioned alkyl groups may be partly or completely fluorinated or mono- or dichlorinated and the above-mentioned aryl groups may be mono- or disubstituted by identical or different groups L, and

Z denotes oxygen, methylene, dimethylmethylene, 1,1-cyclopropylene, difluoromethylene or carbonyl;

while by the aryl groups mentioned in the definition of the above-mentioned groups are meant phenyl or naphthyl groups, which may be mono- or disubstituted independently of one another by identical or different groups L; and

by the heteroaryl groups mentioned in the definition of the above-mentioned groups are meant a pyrrolyl, furanyl, thienyl, pyridyl, indolyl, benzofuranyl, benzothiophenyl, quinolinyl or isoquinolinyl group, or a pyrrolyl, furanyl, thienyl or pyridyl group, wherein one or two methyne groups are replaced by nitrogen atoms, or an indolyl, benzofuranyl, benzothiophenyl, quinolinyl or isoquinolinyl group, wherein one to three methyne groups are replaced by nitrogen atoms,

while the above-mentioned heteroaryl groups may independently of one another be mono- or disubstituted by identical or different groups L;

while by the N-heterocycloalkyl group mentioned in the definition of the above-mentioned groups is meant a saturated carbocyclic ring which comprises an imino group in the ring, which may comprise a further imino group or an O or S atom in the ring, and unless otherwise stated, the above-mentioned alkyl groups may be straight-chain or branched, the tautomers, the mixtures thereof and the physiologically acceptable salts thereof.

2. A D-pyranosyl-substituted phenyl compound of claim 1 according to formula IA

wherein R 1 to R 5 , X, Z, R 7a , R 7b , R 7c have the meanings according to claim 1 .

3. A D-pyranosyl-substituted phenyl of claim 1 , according to formula IA.2

wherein R 1 to R 5 , X, Z, R 7a , R 7b , R 7c have the meanings according to claim 1 .

4. A D-pyranosyl-substituted phenyl compound of claim 1 , wherein:

R 1 denotes hydrogen, fluorine, chlorine, bromine, iodine, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 3-7 -cycloalkyl, C 5-7 -cycloalkenyl, C 1-4 -alkylcarbonyl, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-3 -alkyl)aminocarbonyl, C 1-4 -alkoxycarbonyl, C 1-4 -alkylamino, di-(C 1-3 -alkyl)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, C 1-4 -alkylcarbonylamino, C 1-6 -alkyloxy, C 3-7 -cycloalkyloxy, C 5-7 -cycloalkenyloxy, C 1-4 -alkylsulphanyl, C 1-4 -alkylsulphonyl, C 3-7 -cycloalkylsulphanyl, C 3-7 -cycloalkylsulphonyl, C 5-7 -cycloalkenylsulphanyl, C 5-7 -cycloalkenylsulphonyl, hydroxy or cyano,

while alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl groups may be partly or completely fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and

in cycloalkyl and cycloalkenyl groups one or two methylene groups may be replaced independently of one another by O, S, CO, SO or SO 2 , , and

in N-heterocycloalkyl groups a methylene group may be replaced by CO or SO 2 .

5. A D-pyranosyl-substituted phenyl compound of claim 1 , wherein:

R 3 denotes hydrogen, fluorine, chlorine, bromine, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 3-7 -cycloalkyl, C 3-7 -cycloalkyl-methyl, C 5-7 -cycloalkenyl, C 3-7 -cycloalkenyl-methyl, aryl, heteroaryl, C 1-4 -alkylcarbonyl, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-3 -alkyl)aminocarbonyl, C 1-4 -alkoxycarbonyl, di-(C 1-3 -alkyl)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, C 1-4 -alkylcarbonyl-amino, C 1-6 -alkoxy, C 3-7 -cyclo-alkyloxy, C 5-7 -cycloalkenyloxy, aryloxy, hetero-aryloxy, C 1-4 -alkylsulphanyl, C 1-4 -alkylsulphonyl, C 3-7 -cycloalkylsulphanyl, C 3-7 -cycloalkylsulphonyl, C 5-7 -cycloalkenylsulphanyl, C 5-7 -cycloalkenylsulphonyl, hydroxy or cyano,

while alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl groups may be partly or completely fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and

in cycloalkyl and cycloalkenyl groups one or two methylene groups may be replaced independently of one another by O, S, CO, SO or SO 2 , and

in N-heterocycloalkyl groups a methylene group may be replaced by CO or SO 2 , the terms aryl and heteroaryl are as hereinbefore defined and aryl and heteroaryl groups may independently of one another be mono- or disubstituted by identical or different groups L, where L is defined as in claim 1 .

6. A D-pyranosyl-substituted phenyl compound according to claim 1 , wherein:

X denotes hydrogen, fluorine, chlorine, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, aminocarbonyl, hydroxycarbonyl, C 1-4 -alkoxycarbonyl, C 1-6 -alkylsulphonyl, amino, C 1-5 -alkylamino, N—(C 1-5 -alkyl)-N—(C 1-3 -alkyl)-amino, mercapto or cyano,

while alkyl groups may be partly or completely fluorinated or mono- or dichlorinated, and

the aryl groups may independently of one another be mono- or disubstituted by identical or different groups L, where L is defined as in claim 1 .

7. A D-pyranosyl-substituted phenyl compound according to claim 1 , wherein:

X is hydrogen, chlorine, cyano, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 1-6 -alkylsulphonyl, hydroxycarbonyl, C 1-4 -alkoxycarbonyl, aminocarbonyl or C 1-4 -alkylaminocarbonyl, while alkyl groups may be mono- or polyfluorinated or monosubstituted by hydroxy or cyano.

8. A D-pyranosyl-substituted phenyl compound according to claim 1 , wherein:

X is mercapto, C 1-5 -alkylsulphanyl, C 2-5 -alkenylsulphanyl, C 2-5 -alkynylsulphanyl, C 3-7 -cycloalkylsulphanyl or arylsulphanyl.

9. A D-pyranosyl-substituted phenyl compound according to claim 1 wherein:

X is amino, C 1-5 -alkylamino, N—(C 1-5 -alkyl)-N—(C 1-3 -alkyl)-amino, C 1-4 alkylcarbonylamino, N—(C 1-5 -alkyl)-N—(CN—(C 1-4 -alkylcarbonyl)-amino or arylamino.

10. A D-pyranosyl-substituted phenyl compound according to claim 1 wherein:

X is fluorine.

11. A D-pyranosyl-substituted phenyl compound according to claim 1 wherein:

the group X denotes bromine, iodine, C 1-6 -alkylsulphonyloxy, arylsulphonyloxy or aryl-C 1-3 -alkyl-sulphonyloxy.

12. A D-pyranosyl-substituted phenyl compound according to claim 1 wherein:

R 2 denotes hydrogen, fluorine, chlorine, bromine, methyl, hydroxy, methoxy, ethoxy, trifluoromethoxy, cyano, nitro or methyl substituted by 1 to 3 fluorine atoms.

13. A D-pyranosyl-substituted phenyl compound according to claim 1 wherein:

R 4 and R 5 independently of one another denote hydrogen or fluorine.

14. A D-pyranosyl-substituted phenyl compound according to claim 1 wherein: Z denotes oxygen or methylene.

15. A D-pyranosyl-substituted phenyl compound according to claim 1 wherein: R 7a , R 7b , R 7c independently of one another denote hydrogen, (C 1-6 -alkyl)oxycarbonyl, (C 1-8 -alkyl)carbonyl or benzoyl.

16. A physiologically acceptable salt of a compound according to claim 1 with an inorganic or organic acid.

17. A pharmaceutical composition, comprised of a compound according to claim 1 optionally together with one or more inert carriers and/or diluents.

18. A method of treating a metabolic disorder in a patient wherein the metabolic disorder is selected from the list consisting of type 1 and type 2 diabetes mellitus, complications of diabetes, metabolic acidosis or ketosis, reactive hypoglycaemia, hyperinsulinaemia, glucose metabolic disorder, insulin resistance, metabolic syndrome, dyslipidaemias of different origins, atherosclerosis and related diseases, obesity, high blood pressure, chronic heart failure, oedema and hypemricaemia by administration of a therapeutically effective amount of a compound according to claim 1 or a physiologically acceptable salt thereof.

19. A method of treating the degeneration of pancreatic beta cells and/or improving and/or restoring the functionality of pancreatic beta cells, said method comprised of the step of administering to a patient in need thereof therapeutically effective amount of a compound according to claim 1 or a physiologically acceptable salt thereof.

20. A D-pyranosyl-substituted phenyl compound of general formula I

wherein:

R 1 denotes hydrogen, fluorine, chlorine, bromine, iodine, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 3-10 -cycloalkyl, C 3-10 -cycloalkyl-C 1-3 -alkyl, C 5-10 -cycloalkenyl, C 5-10 -cycloalkenyl-C 1-3 -alkyl, C 1-4 -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-3 -alkyl)aminocarbonyl, pyrrolidin-1-ylcarbonyl, piperidin-1 -ylcarbonyl, morpholin-4-ylcarbonyl, piperazin-1-ylcarbonyl, 4-(C 1-4 -alkyl)piperazin-1-ylcarbonyl, C 1-4 -alkoxycarbonyl, amino, C 1-4 -alkylamino, di-(C 1-3 -alkyl)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, piperazin-1-yl, 4-(C 1-4 -alkyl)piperazin-1-yl, C 1-4 -alkylcarbonylamino, C 1-6 -alkyloxy, C 3-10 -cycloalkyloxy, C 5-10 -cycloalkenyloxy, aryloxy, C 1-4 alkylsulphanyl, C 1-4 -alkylsulphinyl, C 1-4 -alkylsulphonyl, C 3-10 -cycloalkylsulphanyl, C 3-10 -cycloalkylsulphinyl, C 3-10 -cycloalkylsulphonyl, C 5-10 -cycloalkenylsulphanyl, C 5-10 -cycloalkenylsulphinyl, C 5-10 -cycloalkenylsulphonyl, arylsulphanyl, arylsulphinylsulphinyl, arylsulphonyl, hydroxy, cyano or nitro,

while alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl groups may be partly or completely fluorinated or may be mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and in cycloalkyl and cycloalkenyl groups one or two methylene groups may be replaced independently of one another by O, S, CO, SO or SO 2 , and in N-heterocycloalkyl groups a methylene group may be replaced by CO or SO 2 and

R 2 denotes hydrogen, fluorine, chlorine, bromine, hydroxy, C 1-4 -alkyl, C 1-4 -alkoxy, cyano or nitro, while alkyl groups may be mono- or polysubstituted by fluorine, or in the event that R 1 and R 2 are bound to two adjacent C atoms of the phenyl ring, R 1 and R 2 may be joined together such that R 1 and R 2 together form a C 3-5 -alkylene, C 3-5 -alkenylene or butadienylene bridge, which may be partly or completely fluorinated or may be mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 alkoxy and C 1-3 -alkyl, and wherein one or two methylene groups may be replaced independently of one another by O, S, CO, SO, SO 2 or NR N , and wherein in the case of a butadienylene bridge one or two methyne groups may be replaced by an N atom,

R 3 denotes hydrogen, fluorine, chlorine, bromine, iodine, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 3-10 -cycloalkyl, C 3-10 -Cycloalkyl-C 1-3 -alkyl, C 5-10 -cycloalkenyl, C 5-10 -cycloalkenyl-C 1-3 -alkyl, aryl, heteroaryl, C 1-4 -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-3 -alkyl)aminocarbonyl, pyrrolidin-1-ylcarbonyl, piperidin-1-ylcarbonyl, morpholin-4-ylcarbonyl, piperazin-1-ylcarbonyl, 4-(C 1-4 -alkyl)piperazin-1-ylcarbonyl, hydroxycarbonyl, C 1-4 -alkoxycarbonyl, C 1-4 -alkylamino, di-(C 1-3 -alkyl)amino ,pyrrolidin-1- yl, piperidin-1-yl, morpholin-4-yl, piperazin-1-yl, 4-(C 1-4 -alkyl)piperazin-1-yl, C 1-4 -alkylcarbonylamino, arylcarbonylamino, heteroaryl-carbonylamino, C 1-4 -alkysulphonylamino, arylsulphonylamino, C 1-6 -alkoxy, C 3-7 -cycloalkyloxy, C 5-7 -cycloalkenyloxy, aryloxy, heteroaryloxy, C 1-4 -alkyl-sulphanyl, C 1-4 -alkylsulphinyl, C 1-4 alkylsulphonyl, C 3-10 -cycloalkylsulphanyl, C 3-10 -cycloalkylsulphinyl, C 3-10 cycloalkylsulphonyl, C 5-10 -cycloalkenylsulphanyl, C 5-10 -cycloalkenylsulphinyl, C 5-10 -cyclo-alkenylsulphonyl, arylsulphanyl, arylsulphinyl, arylsulphonyl, amino, hydroxy, cyano or nitro,

while alkyl, alkenyl, alkynyl, cycloalkyl- and cycloalkenyl groups may be partly or completely fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and

in cycloalkyl and cycloalkenyl groups one or two methylene groups may be replaced independently of one another by O, S, CO, SO or SO 2 , and

in N-heterocycloalkyl groups a methylene group may be substituted by CO or SO 2 , and

R 4 independently of one another denote hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C 1-3 -alkyl, C 1-3 -alkoxy or methyl or methoxy substituted by 1 to 3 fluorine atoms or

if R 3 and R 4 are bound to two adjacent C atoms of the phenyl ring, R 3 and R 4 may be joined together such that R 3 and R 4 together form a C 3-5 -alkylene, C 3-5 -alkenylene or butadienylene bridge, which may be partly or completely fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl,and wherein one or two methylene groups may be replaced independently of one another by O, S, CO, SO, SO 2 or NR N , and wherein in the case of a butadienylene bridge one or two methyne groups may be replaced by an N atom,

R 5 independently of one another denote hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C 1-3 -alkyl, C 1-3 -alkoxy or methyl or methoxy substituted by 1 to 3 fluorine atoms, and

R N denotes H, C 1-4 -alkyl or C 1-4 -alkylcarbonyl,

L are selected independently of one another from among fluorine, chlorine, bromine, iodine, C 1-3 -alkyl, difluoromethyl, trifluoromethyl, C 1-3 -alkoxy, difluoromethoxy, trifluoromethoxy and cyano,

R 7a , R 7b , R 7c are each hydrogen,

X denotes hydrogen, fluorine, chlorine, bromine, iodine, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 3-7 -cycloalkyl-C 1-3 -alkyl,C 5-7 -cycloalkenyl-C 1-3 -alkyl,aryl-C 1-3 -alkyl, heteroary- 1-3 -alkyl, C 1-6 -alkoxy, C 2-6 -alkenyloxy, C 2-6 -alkynyloxy, C 3-7 -cycloalkyloxy, C 5-7 -cycloalkenyloxy, aryloxy, heteroaryloxy, C 3-7 -cycloalkyl-C 1-3 -alkyloxy, C 5-7 -cycloalkenyl-C 1-3 -alkyloxy, aryl-C 1-3 -alkyloxy, heteroaryl-C 1-3 -alkyloxy, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-3 -alkyl)aminocarbonyl,hydroxycarbonyl, C 1-4 -alkoxycarbonyl, aminocarbonyl-C 1-3 -alkyl, C 1-4 -alkylaminocarbonyl-C 1-3 -alkyl, di-(C 1-3 -alkyl)aminocarbonyl-C 1-3 -alkyl, hydroxycarbonyl-C 1-3 -alkyl, C 1-4 -alkoxycarbonyl-C 1-3 -alkyl, C 3-7 -cycloalkyloxy-C 1-3 -alkyl, C 5-7 -cycloalkenyloxy-C 1-3 -alkyl, aryloxy-C 1-3 -alkyl, heteroaryloxy-C 1-3 -alkyl, C 1-4 -alkylsulphonyloxy, arylsulphonyloxy, aryl-C 1-3 -alkyl-sulphonyloxy or cyano, while a methylene group directly linked to the pyranose ring may be replaced by NR N , S, CO, SO or SO 2 , and

the alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl groups therein may be partly or completely fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, cyano, hydroxy, C 1-3 -alkoxy, C 1-3 -alkylsulphanyl, —NH 2 , —NHR N , —NR N (C 1-3 -alkyl) and C 1-3 -alkyl, and

in the cycloalkyl and cycloalkenyl groups therein one or two methylene groups may be replaced independently of one another by O, S, CO, SO or SO 2 , and

Z denotes oxygen, methylene, dimethylmethylene, 1,1-cyclopropylene, difluoromethylene or carbonyl;

while by the aryl groups mentioned in the definition of the above-mentioned groups are meant phenyl or naphthyl groups, which may be mono- or disubstituted independently of one another by identical or different groups L; and

by the heteroaryl groups mentioned in the definition of the above-mentioned groups are meant a pyrrolyl, furanyl, thienyl, pyridyl, indolyl, benzofuranyl, benzothiophenyl, qiuinolinyl or isoguinolinyl group, or a pyrrolyl, furanyl, thienyl or pyridyl group, wherein one or two methyne groups are replaced by nitrogen atoms, or an indolyl, benzofuranyl, benzothiophenyl, qiuinolinyl or isoquinolinyl group, wherein one to three methyne groups are replaced by nitrogen atoms,

while the above-mentioned heteroaryl groups may independently of one another be mono- or disubstituted by identical or different groups L;

while by the N-heterocycloalkyl group mentioned in the definition of the above-mentioned groups is meant a saturated carbocyclic ring which comprises an imino group in the ring, which may comprise a further imino group or an O or S atom in the ring, and unless otherwise stated, the above-mentioned alkyl groups may be straight-chain or branched, the tautomers, the mixtures thereof and the physiologically acceptable salts thereof.

21. A D-pyranosyl-substituted phenyl compound of general formula IB

wherein:

R 1 denotes hydrogen, fluorine, chlorine, bromine, iodine, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 3-10 -cycloalkyl, C 3-10 -cycloalkyl-C 1-3 -alkyl, C 5-10 -cycloalkenyl, C 5-10 -cycloalkenyl-C 1-3 -alkyl,C 1-4 -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-3 -alkyl)aminocarbonyl, pyrrolidin-1-ylcarbonyl, piperidin-1-ylcarbonyl, morpholin-4-ylcarbonyl, piperazin-1-ylcarbonyl, 4-(C 1-4 -alkyl)piperazin-1-ylcarbonyl, C 1-4 -alkoxycarbonyl, amino, C 1-4 -alkylamino, di-(C 1-3 -alkyl)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, piperazin-1-yl, 4-(C 1-4 -alkyl)piperazin-1-yl, C 1-4 -alkylcarbonylamino, C 1-6 -alkyloxy, C 3-10 -cycloalkyloxy, C 5-10 -cycloalkenyloxy, aryloxy, C 1-4 -alkylsulphanyl, C 1-4 -alkylsulphinyl, C 1-4 -alkylsulphonyl, C 3-10 -cycloalkylsulphanyl, C 3-10 -cycloalkylsulphinyl, C 3-10 -cycloalkylsulphonyl, C 5-10 -cycloalkenylsulphanyl, C 5-10 -cycloalkenylsulphinyl, C 5-10 -cycloalkenylsulphonyl, arylsulphanyl, arylsulphinyl, arylsulphonyl, hydroxy, cyano or nitro,

while alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl groups may be partly or completely fluorinated or may be mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and in cycloalkyl and cycloalkenyl groups one or two methylene groups may be replaced independently of one another by O, S, CO, SO or SO 2 , and

in N-heterocycloalkyl groups a methylene group may be replaced by CO or SO 2 , and

R 2 denotes hydrogen, fluorine, chlorine, bromine, hydroxy, C 1-4 -alkyl, C 1-4 -alkoxy, cyano or nitro, while alkyl groups may be mono- or polysubstituted by fluorine, or in the event that R 1 and R 2 are bound to two adjacent C atoms of the phenyl ring, R 1 and R 2 may be joined together such that R 1 and R 2 together form a C 3-5 -alkylene, C 3-5 -alkenylene or butadienylene bridge, which may be partly or completely fluorinated or may be mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and wherein one or two methylene groups may be replaced independently of one another by O, S, CO, SO, SO 2 or NR N , and wherein in the case of a butadienylene bridge one or two methyne groups may be replaced by an N atom,

R 3 denotes hydrogen, fluorine, chlorine, bromine, iodine, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 3-10 -cycloalkyl, C 3-10 -Cycloalkyl-C 1-3 -alkyl, C 5-10 -cycloalkenyl, C 5-10 -cycloalkenyl-C 1-3 -alkyl, aryl, heteroaryl, C 1-4 -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-3 -alkyl)aminocarbonyl, pyrrolidin-1-ylcarbonyl, piperidin-1-ylcarbonyl, morpholin-4-ylcarbonyl, piperazin-1-ylcarbonyl, 4-(C 1-4 -alkyl) piperazin-1-ylcarbonyl, hydroxycarbonyl, C 1-4 -alkoxycarbonyl, C 1-4 -alkylamino, di-(C 1-3 -alkyl)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, piperazin-1-yl, 4-(C 1-4 -alkyl)piperazin-1-yl, C 1-4 -alkylcarbonylamino, arylcarbonylamino, heteroaryl-carbonylamino, C 1-4 -alkylsulphonylamino, arylsulphonylamino, C 1-6 -alkoxy, C 3-7 -cycloalkyloxy, C 5-7 -cycloalkenyloxy, aryloxy, heteroaryloxy, C 1-4 -alkyl-sulphanyl, C 1-4 -alkylsulphinyl, C 1-4 -alkylsulphonyl, C 3-10 -cycloalkylsulphanyl, C 3-10 -cycloalkylsulphinyl, C 3-10 -cycloalkylsulphonyl, C 5-10 -cycloalkenylsulphanyl, C 5-10 -cycloalkenylsulphinyl, C 5-10 -cycloalkenylsulphonyl, arylsulphanyl, arylsulphinyl, arylsulphonyl, amino, hydroxy, cyano or nitro,

while alkyl, alkenyl, alkynyl, cycloalkyl- and cycloalkenyl groups may be partly or completely fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and

in cycloalkyl and cycloalkenyl groups one or two methylene groups may be replaced independently of one another by O, S, CO, SO or SO 2 , and

in N-heterocycloalkyl groups a methylene group may be substituted by CO or S 0 2 , and

R 4 independently of one another denote hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C 1-3 -alkyl, C 1-3 -alkoxy or methyl or methoxy substituted by 1 to 3 fluorine atoms, or

if R 3 and R 4 are bound to two adjacent C atoms of the phenyl ring, R 3 and R 4 may be joined together such that R 3 and R 4 together form a C 3-5 -alkylene, C 3-5 -alkenylene or butadienylene bridge, which may be partly or completely fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and wherein one or two methylene groups may be replaced independently of one another by O, S, CO, SO, SO 2 or NR N, and wherein in the case of a butadienylene bridge one or two methyne groups may be replaced by an N atom,

R 5 independently of one another denote hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C 1-3 -alkyl, C 1-3 -alkoxy or methyl or methoxy substituted by 1 to 3 fluorine atoms, and

R N denotes H, C 1-4 -alkyl or C 1-4 -alkylcarbonyl,

L are selected independently of one another from among fluorine, chlorine, bromine, iodine, C 1-3 -alkyl, difluoromethyl, trifluoromethyl, C 1-3 -alkoxy, difluoromethoxy, trifluoromethoxy and cyano,

R 7a , R 7b , R 7c independently of one another have a meaning selected from among hydrogen, (C 1-18 -alkyl)carbonyl, (C 1-18 -alkyl)oxycarbonyl, arylcarbonyl and aryl-(C 1-3 -alkyl)-carbonyl,

X denotes hydrogen, fluorine, chlorine, bromine, iodine, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 3-7 -cycloalkyl-C 1-3 -alkyl, C 5-7 -cycloalkenyl-C 1-3 -alkyl, aryl-C 1-3 -alkyl, heteroaryl-C 1-3 -alkyl, C 1-6 -alkoxy, C 2-6 -alkenyloxy, C 2-6 -alkynyloxy, C 3-7 -cycloalkyloxy, C 5-7 -cycloalkenyloxy, aryloxy, heteroaryloxy, C 3-7 -cycloalkyl-C 1-3 -alkyloxy, C 5-7 -cycloalkenyl-C 1-3 -alkyloxy, aryl-C 1-3 -alkyloxy, heteroaryl-C 1-3 -alkyloxy, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-3 -alkyl)aminocarbonyl, hydroxycarbonyl, C 1-4 -alkoxycarbonyl, aminocarbonyl-C 1-3 -alkyl, C 1-4 -alkylaminocarbonyl-C 1-3 -alkyl, di-(C 1-3 -alkyl)aminocarbonyl-C 1-3 -alkyl, hydroxycarbonyl-C 1-3 -alkyl, C 1-4 -alkoxycarbonyl-C 1-3 -alkyl, C 3-7 -cycloalkyloxy-C 1-3 -alkyl, C 5-7 -cycloalkenyloxy-C 1-3 -alkyl, aryloxy-C 1-3 -alkyl, heteroaryloxy-C 1-3 -alkyl, C 1-4 -alkylsulphonyloxy, arylsulphonyloxy, aryl-C 1-3 -alkyl-sulphonyloxy or cyano,

while a methylene group directly linked to the pyranose ring may be replaced by NR N , S, CO, SO or SO 2 , and

alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl groups may be partly or completely fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, cyano, hydroxy, C 1-3 -alkoxy, C 1-3 -alkylsulphanyl, —NH 2 , —NHR N , —NR N (C 1-3 -alkyl) and C 1-3 -alkyl, and

in cycloalkyl and cycloalkenyl groups one or two methylene groups may be replaced independently of one another by O, S, CO, SO or SO 2 ,

and

Z denotes oxygen, methylene, dimethylmethylene, 1,1-cyclopropylene, difluoromethylene or carbonyl;

while by the aryl groups mentioned in the definition of the above-mentioned groups are meant phenyl or naphthyl groups, which may be mono- or disubstituted independently of one another by identical or different groups L; and

by the heteroaryl groups mentioned in the definition of the above-mentioned groups are meant a pyrrolyl, furanyl, thienyl, pyridyl, indolyl, benzofuranyl, benzothiophenyl, quinolinyl or isoquinolinyl group, or a pyrrolyl, furanyl, thienyl or pyridyl group, wherein one or two methyne groups are replaced by nitrogen atoms, or an indolyl, benzofuranyl, benzothiophenyl, quinolinyl or isoquinolinyl group, wherein one to three methyne groups are replaced by nitrogen atoms,

while the above-mentioned heteroaryl groups may independently of one another be mono- or disubstituted by identical or different groups L;

while by the N-heterocycloalkyl group mentioned in the definition of the above-mentioned groups is meant a saturated carbocyclic ring which comprises an imino group in the ring, which may comprise a further imino group or an O or S atom in the ring, and unless otherwise stated, the above-mentioned alkyl groups may be straight-chain or branched, the tautomers, the mixtures thereof and the physiologically acceptable salts thereof.

22. A pharmaceutical composition, comprised of a compound according to claim 20 optionally together with one or more inert carriers and/or diluents.

23. A pharmaceutical composition, comprised of a compound according to claim 21 optionally together with one or more inert carriers and/or diluents.

24. A pharmaceutical composition, comprised of a compound of general formula I

wherein:

R 1 denotes hydrogen, fluorine, chlorine, bromine, iodine, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 3-10 -cycloalkyl, C 3-10 -cycloalkyl-C 1-3 -alkyl, C 5-10 -cycloalkenyl, C 5-10 -cycloalkenyl-C 1-3 -alkyl, C 1-4 -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-3 -alkyl)aminocarbonyl, pyrrolidin-1-ylcarbonyl, piperidin-1-ylcarbonyl, morpholin-4-ylcarbonyl, piperazin-1-ylcarbonyl, 4-(C 1-4 -alkyl)piperazin-1-ylcarbonyl, C 1-4 -alkoxycarbonyl, amino, C 1-4 -alkylamino, di-(C 1-3 -alkyl)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, piperazin-1-yl, 4-(C 1-4 -alkyl)piperazin-1-yl, C 1-4 -alkylcarbonylamino, C 1-6 -alkyloxy, C 3-10 -cycloalkyloxy, C 5-10 -cycloalkenyloxy, aryloxy, C 1-4 -alkylsulphanyl, C 1-4 -alkylsulphinyl, C 1-4 -alkylsulphonyl, C 3-10 -cycloalkylsulphanyl, C 3-10 -cycloalkylsulphinyl, C 3-10 -cycloalkylsulphonyl, C 5-10 -cycloalkenylsulphanyl, C 5-10 -cycloalkenylsulphinyl, C 5-10 -cycloalkenylsulphonyl, arylsulphanyl, arylsulphinyl, arylsulphonyl, hydroxy, cyano or nitro,

while alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl groups may be partly or completely fluorinated or may be mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and in cycloalkyl and cycloalkenyl groups one or two methylene groups may be replaced independently of one another by O, S, CO, SO or SO 2 , and in N-heterocycloalkyl groups a methylene group may be replaced by CO or SO 2 , and

R 2 denotes hydrogen, fluorine, chlorine, bromine, hydroxy, C 1-4 -alkyl, C 1-4 -alkoxy, cyano or nitro, while alkyl groups may be mono- or polysubstituted by fluorine, or in the event that R 1 and R 2 are bound to two adjacent C atoms of the phenyl ring, R 1 and R 2 may be joined together such that R 1 and R 2 together form a C 3-5 -alkylene, C 3-5 -alkenylene or butadienylene bridge, which may be partly or completely fluorinated or may be mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and wherein one or two methylene groups may be replaced independently of one another by O, S, CO, SO, SO 2 or NR N , and wherein in the case of a butadienylene bridge one or two methyne groups may be replaced by an N atom,

R 3 denotes hydrogen, fluorine, chlorine, bromine, iodine, C 1-6 -alkyl, C 2-6 -alkynyl, C 2-6 -alkenyl, C 3-10 -cycloalkyl, C 3-10 -Cycloalkyl-C 1-3 -alkyl, C 5-10 -cycloalkenyl, C 5-10 -cycloalkenyl-C 1-3 -alkyl, aryl, heteroaryl, C 1-4 -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-3 -alkyl)aminocarbonyl, pyrrolidin-1-ylcarbonyl, piperidin-1-ylcarbonyl, morpholin-4-ylcarbonyl, piperazin-1-ylcarbonyl, 4-(C 1-4 -alkyl)piperazin-1-ylcarbonyl, hydroxycarbonyl, C 1-4 -alkoxycarbonyl, C 1-4 -alkylamino, di-(C 1-3 -alkyl)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, piperazin-1-yl, 4-(C 1-4 -alkyl)piperazin-1-yl, C 1-4 -alkylcarbonylamino, arylcarbonylamino, heteroaryl-carbonylamino, C 1-4 -alkylsulphonylamino, arylsulphonylamino, C 1-6 -alkoxy, C 3-7 -cycloalkyloxy, C 5-7 -cycloalkenyloxy, aryloxy, heteroaryloxy, C 1-4 -alkyl-sulphanyl, C 1-4 -alkylsulphinyl, C 1-4 -alkylsulphonyl, C 3-10 -cycloalkylsulphanyl, C 3-10 -cycloalkylsulphinyl, C 3-10 -cycloalkylsulphonyl, C 5-10 -cycloalkenylsulphanyl, C 5-10 -cycloalkenylsulphinyl, C 5-10 -cycloalkenylsulphonyl, arylsulphanyl, arylsulphinyl, arylsulphonyl, amino, hydroxy, cyano or nitro,

while alkyl, alkenyl, alkynyl, cycloalkyl- and cycloalkenyl groups may be partly or completely fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and

in cycloalkyl and cycloalkenyl groups one or two methylene groups may be replaced independently of one another by O, S, CO, SO or SO 2 , and

in N-heterocycloalkyl groups a methylene group may be substituted by CO or SO 2 , and

R 4 independently of one another denote hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C 1-3 -alkyl, C 1-3 -alkoxy or methyl or methoxy substituted by1 to 3 fluorine atoms, or

if R 3 and R 4 are bound to two adjacent C atoms of the phenyl ring, R 3 and R 4 may be joined together such that R 3 and R 4 together form a C 3-5 -alkylene, C 3-5 -alkenylene or butadienylene bridge, which may be partly or completely fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C 1-3 -alkoxy and C 1-3 -alkyl, and wherein one or two methylene groups may be replaced independently of one another by O, S, CO, SO, SO 2 or NR N , and wherein in the case of a butadienylene bridge one or two methyne groups may be replaced by an N atom,

R 5 independently of one another denote hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C 1-3 -alkyl, C 1-3 -alkoxy or methyl or methoxy substituted by 1 to 3 fluorine atoms, and

R N denotes H, C 1-4 -alkyl or C 1-4 -alkylcarbonyl,

L are selected independently of one another from among fluorine, chlorine, bromine, iodine, C 1-3 -alkyl, difluoromethyl, trifluoromethyl, C 1-3 -alkoxy, difluoromethoxy, trifluoromethoxy and cyano,

R 7a , R 7b , R 7c independently of one another have a meaning selected from among hydrogen, (C 1-18 -alkyl)carbonyl, (C 1-18 -alkyl)oxycarbonyl, arylcarbonyl and aryl-(C 1-3 -alkyl)-carbonyl,

X denotes hydrogen, fluorine, chlorine, bromine, iodine, C 1-6 -alkyl, C 2-6 -alkynyl, C 3-7 -cycloalkyl-C 1-3 -alkyl, C 5-7 -cycloalkenyl-C 1-3 -alkyl, aryl-C 1-3 -alkyl, heteroaryl-C 1-3 -alkyl, C 1-6 -alkoxy, C 2-6 -alkenyloxy, C 2-6 -alkynyloxy, C 3-7 -cycloalkyloxy, C 5-7 -cycloalkenyloxy, aryloxy, heteroaryloxy, C 3-7 -cycloalkyl-C 1-3 -alkyloxy, C 5-7 -cycloalkenyl-C 1-3 -alkyloxy, aryl-C 1-3 -alkyloxy, heteroaryl-C 1-3 -alkyloxy, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-3 -alkyl)aminocarbonyl, hydroxycarbonyl, C 1-4 -alkoxycarbonyl, aminocarbonyl-C 1-3 -alkyl, C 1-4 -alkylaminocarbonyl-C 1-3 -alkyl, di-(C 1-3 -alkyl)aminocarbonyl-C 1-3 -alkyl, hydroxycarbonyl-C 1-3 -alkyl, C 1-4 -alkoxycarbonyl-C 1-3 -alkyl, C 3-7 -cycloalkyloxy-C 1-3 -alkyl,C 5-7 -cycloalkenyloxy-C 1-3 -alkyl, aryloxy-C 1-3 -alkyl, heteroaryloxy-C 1-3 -alkyl, C 1-4 -alkylsulphonyloxy, arylsulphonyloxy, aryl-C 1-3 -alkyl-sulphonyloxy or cyano,

while a methylene group directly linked to the pyranose ring may be replaced by NR N , S, CO, SO or SO 2 , and

alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl groups may be partly or completely fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, cyano, hydroxy, C 1-3 -alkoxy, C 1-3 -alkylsulphanyl, —NH 2 , —NHR N , —NR N (C 1-3 -alkyl) andC13-alkyl, and

in cycloalkyl and cycloalkenyl groups one or two methylene groups may be replaced independently of one another by O, S, CO, SO or SO 2 ,

and

Z denotes oxygen, methylene, dimethylmethylene, 1,1 -cyclopropylene, difluoromethylene or carbonyl;

while by the aryl groups mentioned in the definition of the above-mentioned groups are meant phenyl or naphthyl groups, which may be mono- or disubstituted independently of one another by identical or different groups L; and

by the heteroaryl groups mentioned in the definition of the above-mentioned groups are meant a pyrrolyl, furanyl, thienyl, pyridyl, indolyl, benzofuranyl, benzothiophenyl, quinolinyl or isoquinolinyl group, or a pyrrolyl, furanyl, thienyl or pyridyl group, wherein one or two methyne groups are replaced by nitrogen atoms, or an indolyl, benzofuranyl, benzothiophenyl, quinolinyl or isoquinolinyl group, wherein one to three methyne groups are replaced by nitrogen atoms,

while the above-mentioned heteroaryl groups may independently of one another be mono- or disubstituted by identical or different groups L;

while by the N-heterocycloalkyl group mentioned in the definition of the above-mentioned groups is meant a saturated carbocyclic ring which comprises an imino group in the ring, which may comprise a further imino group or an O or S atom in the ring, and unless otherwise stated, the above-mentioned alkyl groups may be straight-chain or branched, the tautomers, the mixtures thereof and the physiologically acceptable salts thereof, together with one or more inert carriers and/or diluents.

25. A method of treating a metabolic disorder in a patient wherein the metabolic disorder is selected from the list consisting of type 1 and type 2 diabetes mellitus, complications of diabetes, metabolic acidosis or ketosis, reactive hypoglycaemia, hyperinsulinaemia, glucose metabolic disorder, insulin resistance, metabolic syndrome, dyslipidaemias of different origins, atherosclerosis and related diseases, obesity, high blood pressure, chronic heart failure, oedema and hypemricaemia by administration of a therapeutically effective amount of a compound according to claim 20 or a physiologically acceptable salt thereof.

26. A method of treating the degeneration of pancreatic beta cells and/or improving and/or restoring the functionality of pancreatic beta cells, said method comprised of the step of administering to a patient in need thereof therapeutically effective amount of a compound according to claim 20 or a physiologically acceptable salt thereof.

27. A method of treating a metabolic disorder in a patient wherein the metabolic disorder is selected from the list consisting of type 1 and type 2 diabetes mellitus, complications of diabetes, metabolic acidosis or ketosis, reactive hypoglycaemia, hyperinsulinaemia, glucose metabolic disorder, insulin resistance, metabolic syndrome, dyslipidaemias of different origins, atherosclerosis and related diseases, obesity, high blood pressure, chronic heart failure, oedema and hypemricaemia by administration of a therapeutically effective amount of a compound according to claim 21 or a physiologically acceptable salt thereof.

28. A method of treating the degeneration of pancreatic beta cells and/or improving and/or restoring the functionality of pancreatic beta cells, said method comprised of the step of administering to a patient in need thereof therapeutically effective amount of a compound according to claim 21 or a physiologically acceptable salt thereof.