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

A D-Xylopyranosyl-substituted phenyl compound of formula I

• wherein
• R1 denotes hydrogen, fluorine, chlorine, bromine, C1-6-alkyl, C2-6-alkynyl, C2-6-alkenyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, C5-7-cycloalkenyl, C5-7-cycloalkenyl-C1-3-alkyl, C1-4-alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aminocarbonyl, C1-4-alkylaminocarbonyl, di-(C1-3-alkyl)aminocarbonyl, pyrrolidin-1-ylcarbonyl, piperidin-1-ylcarbonyl, morpholin-4-ylcarbonyl, piperazin-1-ylcarbonyl, 4-(C1-4-alkyl)piperazin-1-ylcarbonyl, C1-4-alkoxycarbonyl, amino, C1-4-alkylamino, di-(C1-3-alkyl)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, piperazin-1-yl, 4-(C1-4-alkyl)piperazin-1-yl, C1-4-alkylcarbonylamino, C1-6-alkyloxy, C3-7-cycloalkyloxy, C5-7-cycloalkenyloxy, aryloxy, C1-4-alkylsulphanyl, C1-4-alkylsulphinyl, C1-4-alkylsulphonyl, C3-7-cycloalkylsulphanyl, C3-7-cycloalkylsulphinyl, C3-7-cycloalkylsulphonyl, C5-7-cycloalkenylsulphanyl, C5-7-cycloalkenylsulphinyl, C5-7-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, C1-3-alkoxy and C1-3-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 SO2, and
• in N-heterocycloalkyl groups a methylene group may be replaced by CO or SO2, and
• R2 denotes hydrogen, fluorine, chlorine, bromine, hydroxy, C1-4-alkyl, C1-4-alkoxy, cyano or nitro, while alkyl groups may be mono- or polysubstituted by fluorine, or
• in the event that R1 and R2 are bound to two C atoms of the phenyl ring which are adjacent to one another, R1 and R2 may be joined together in such a way that R1 and R2 together form a C3-5-alkylene or C3-5-alkenylene bridge, which may be partly or totally fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C1-3-alkoxy and C1-3-alkyl and wherein one or two methylene groups may be replaced independently of one another by O, S, CO, SO, SO2 or NRN,
• R3 denotes hydrogen, fluorine, chlorine, bromine, C1-6-alkyl, C2-6-alkynyl, C2-6-alkenyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, C5-7-cycloalkenyl, C5-7-cycloalkenyl-C1-3-alkyl, aryl, heteroaryl, C1-4-alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aminocarbonyl, C1-4-alkylaminocarbonyl, di-(C1-3-alkyl)aminocarbonyl, pyrrolidin-1-ylcarbonyl, piperidin-1-ylcarbonyl, morpholin-4-ylcarbonyl, piperazin-1-ylcarbonyl, 4-(C1-4-alkyl)piperazin-1-ylcarbonyl, hydroxycarbonyl, C1-4-alkoxycarbonyl, C1-4-alkylamino, di-(C1-3-alkyl)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, piperazin-1-yl, 4-(C1-4-alkyl)piperazin-1-yl, C1-4-alkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, C1-4-alkylsulphonylamino, arylsulphonylamino, C1-6-alkoxy, C3-7-cycloalkyloxy, C5-7-cycloalkenyloxy, aryloxy, heteroaryloxy, C1-4-alkylsulphanyl, C1-4-alkylsulphinyl, C1-4-alkylsulphonyl, C3-7-cycloalkylsulphanyl, C3-7-cycloalkylsulphinyl, C3-7-cycloalkylsulphonyl, C5-7-cycloalkenylsulphanyl, C5-7-cycloalkenylsulphinyl, C5-7-cycloalkenylsulphonyl, arylsulphanyl, arylsulphinyl, arylsulphonyl, amino, hydroxy, cyano or nitro,
• while alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl groups may be partly or totally fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C1-3-alkoxy and C1-3-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 SO2, and
• in N-heterocycloalkyl groups a methylene group may be replaced by CO or SO2, and
• R4 denotes hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C1-3-alkyl, C1-3-alkoxy or methyl or methoxy substituted by 1 to 3 fluorine atoms, or
• in the event that R3 and R4 are bound to two C atoms of the phenyl ring which are adjacent to one another, R3 and R4 may be joined together in such a way that R3 and R4 together form a C3-5-alkylene or C3-5-alkenylene bridge, which may be partly or totally fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, hydroxy, C1-3-alkoxy and C1-3-alkyl and wherein one or two methylene groups may be replaced independently of one another by O, S, CO, SO, SO2 or NRN,
• R5 denotes hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C1-3-alkyl, C1-3-alkoxy or methyl or methoxy substituted by 1 to 3 fluorine atoms, and
• RN independently of one another denote H or C1-4-alkyl,
• L are selected independently of one another from among fluorine, chlorine, bromine, iodine, C1-3-alkyl, difluoromethyl, trifluoromethyl, C1-3-alkoxy, difluoromethoxy, trifluoromethoxy and cyano,
• R7a, R7b, and
• R7c independently of one another have a meaning selected from among hydrogen, (C1-18-alkyl)carbonyl, (C1-18-alkyl)oxycarbonyl, arylcarbonyl and aryl-(C1-3-alkyl)-carbonyl,
• X denotes hydrogen, C1-6-alkyl, C2-6-alkynyl, C2-6-alkenyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, C5-7-cycloalkenyl, C5-7-cycloalkenyl-C1-3-alkyl, aryl, aryl-C1-3-alkyl, heteroaryl, heteroaryl-C1-3-alkyl, C1-4-alkylcarbonyl, arylcarbonyl, aminocarbonyl, C1-4-alkylaminocarbonyl, di-(C1-3-alkyl)aminocarbonyl, (aryl-C1-3-alkyl)aminocarbonyl, pyrrolidin-1-ylcarbonyl, piperidin-1-ylcarbonyl, morpholin-4-ylcarbonyl, hydroxycarbonyl, C1-4-alkoxycarbonyl, C1-4-alkylcarbonylamino-C1-3-alkyl, N-(C1-4-alkylcarbonyl)-N-(C1-3-alkyl)-amino-C1-3-alkyl, arylcarbonylamino-C1-3-alkyl, C1-4-alkylsulphonylamino-C1-3-alkyl, arylsulphonylamino-C1-3-alkyl, C1-6-alkoxy-C1-3-alkyl, C3-7-cycloalkyloxy-C1-3-alkyl, C5-7-cycloalkenyloxy-C1-3-alkyl, aryloxy-C1-3-alkyl, heteroaryloxy-C1-3-alkyl, C1-4-alkylsulphanyl-C1-3-alkyl, C1-4-alkylsulphinyl-C1-3-alkyl, C1-4-alkylsulphinyl, C1-4-alkylsulphonyl, C1-4-alkylsulphonyl-C1-3-alkyl, C1-4-arylsulphanyl-C1-3-alkyl, arylsulphonyl-C1-3-alkyl, aryl-C1-3-alkyl-sulphonyl-C1-3-alkyl, C1-4-alkylsulphonyloxy-C1-3-alkyl, arylsulphonyloxy-C1-3-alkyl, aryl-C1-3-alkyl-sulphonyloxy-C1-3-alkyl, C3-7-cycloalkylsulphanyl-C1-3-alkyl, C3-7-cycloalkylsulphinyl, C3-7-cycloalkylsulphonyl, C5-7-cycloalkenylsulphanyl-C1-3-alkyl, C5-7-cycloalkenylsulphinyl, C5-7-cycloalkenylsulphonyl, C1-4-alkylcarbonylsulphanyl-C1-3-alkyl or cyano,
• while alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl groups may be partly or totally fluorinated or mono- or disubstituted by identical or different substituents selected from chlorine, cyano, hydroxy, mercapto, C1-3-alkoxy and C1-3-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 SO2, and
• in N-heterocycloalkyl groups a methylene group may be replaced by CO or SO2, and
• provided that X representing hydroxymethyl is excluded,
• Z denotes oxygen, methylene, dimethylmethylene, difluoromethylene or carbonyl;
• while the term aryl groups used in the definition of the above groups denotes phenyl or naphthyl groups, which may be mono- or disubstituted independently of one another by identical or different groups L;
• and
• the term heteroaryl groups used in the definition of the above-mentioned groups denotes a pyrrolyl, furanyl, thienyl, pyridyl, indolyl, benzofuranyl, benzothiophenyl, quinolinyl or isoquinolinyl group,
• or a pyrrolyl, furanyl, thienyl, pyridyl or imidazolyl 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 be mono- or disubstituted independently of one another 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 another optionally substituted 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,
• or a tautomer or stereoisomer thereof or mixtures thereof or a salt thereof.