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filingDate 2005-03-16-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_07522d5c705da5887388884dfdeb9ca5
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publicationDate 2006-03-22-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber AR-048041-A1
titleOfInvention BENCH DERIVATIVES REPLACED BY GLUCOPIRANOSILO, PHARMACEUTICAL COMPOSITIONS AND PROCEDURE FOR PREPARATION
abstract Glucopyranosyl substituted benzene derivatives of the general formula (1), in which: R1 is selected from the meanings of group A and if R3 is selected from the meanings of group B, R1 may additionally be selected from the meanings hydrogen, fluorine, chlorine, bromine, iodine, C 1-4 alkyl, C 2-4 alkenyl-C 1-4 alkyl, C 2-4 alkynyl, C 2-4 alkenyl-C 1-4 alkoxy, C 2-4 alkynylC 1-4 alkoxy -4, C3-7 cycloalkyl-C1-4 alkyl, C5-7 cycloalkenyl-C1-4 alkyl, a methyl group substituted by 1 to 3 fluorine atoms, an ethyl group substituted by 1 to 5 fluorine atoms, C1- alkoxy 4, a methoxy group substituted by 1 to 3 fluorine atoms, an ethoxy group substituted by 1 to 5 fluorine atoms, a C1-4 alkyl group, substituted by a hydroxy- or C1-3 alkoxy group, a C2- alkoxy group 4 substituted by a hydroxy or C 1-3 alkoxy, C 3-6 cycloalkyl-C 1-3 alkoxy or hydroxy group, being able to in the cycloalkyl and cycloalkenyl rings mentioned in l or above, be substituted one or two methyl groups, independently of each other, by O or CO; and R2 may be hydrogen, fluorine, chlorine, bromine, hydroxy, C1-4 alkyl, C1-4 alkoxy, cyano or nitro, the alkyl or alkoxy group may be substituted once or several times by fluorine; and R3 is selected from the meanings of Group B and if R1 is selected from among the meanings of Group A, R3 may be additionally selected from the meanings hydrogen, fluorine, chlorine, bromine, iodine, C1-6 alkyl, C2 alkenyl -4-C1-4 alkyl, C2-4 alkynyl-C1-4 alkyl, C2-4 alkenyl-C1-4 alkoxy, C1-4 alkynyl C1-4 cycloalkyl, C5-7 cycloalkenyl, C3-7 cycloalkyl -C 1-4 alkyl, C 5-7 cycloalkenyl-C 1-4 alkyl, C 3-6 cycloalkylidene, hydroxy, C 1-6 alkoxy, C 3-6 cycloalkyl-C 1-3 alkoxy, aryl, C 1-3 arylalkyl, heteroaryl, heteroarylalkyl C 1-3, aryloxy, C 1-3 alkyl arylalkyl, a methyl or methoxy group substituted by 1 to 3 fluorine atoms, a C2-4 alkyl or C2-4 alkoxy group substituted by 1 to 5 fluorine atoms, an alkyl group C1-4 substituted by a cyano group, a C1-4 alkyl group substituted by a hydroxy or C1-3-oxy alkyl, cyano, carboxy, C1-3-alkoxycarbonyl, aminocarbonyl, (C1-3-alkyl) carbonyl group di-amino (C1-3 alkyl) carbonyl, pyrrolidin-1-yl-carbonyl, piperidin-1-yl-carbonyl, morpholin-4-yl-carbonyl, piperazin-1-yl-carbonyl, 4- (C1-3 alkyl) -piperazin -1-yl-carbonyl, C 1-4 alkylcarbonylamino, C 1-4 alkyl sulfonylamino, C 1-4 alkyl sulfanyl, C 1-4 alkyl sulfinyl, C 1-4 alkyl sulfonyl, arylsulfonylamino, C 1-3 alkyl sulfonylamino or arylsulfonyl; R4, R5 are independently of each other, hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C1-3 alkyl, C1-3 alkoxy, methyl or methoxy substituted by 1 to 3 fluorine atoms; A means C2-6-1-yl alkyne, C2-6-1-yl alken, C3-7 cycloalkyl, C5-7 cycloalkenyl, aryl, heteroaryl, C1-4-alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aminocarbonyl, C1- alkyl 4-aminocarbonyl, di-amino (C1-3alkyl) carbonyl, pyrrolidin-1-yl-carbonyl, piperidin-1-yl-carbonyl, morpholin-4-yl-carbonyl, piperazin-1-yl-carbonyl, 4- ( C 1-4 alkyl) piperazin-1-yl-carbonyl, arylaminocarbonyl, heteroarylaminocarbonyl, C 1-4 alkoxycarbonyl, C 1-3 arylalkoxy-alkoxycarbonyl, C 1-3-carbonyl heteroarylalkoxy, amino, C 1-4 alkyl, di - (C1-3 alkyl) amino, pyrrolidin-1-yl, pyrrolidin-2-on-1-yl, piperidin-1- yl, piperidin-2-on-1-yl, morpholin-4-yl, morpholin-3 -on-4-yl, piperazin-1-yl, 4- (C1-3 alkyl) -piperazin-1-yl, C1-4 alkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, C3-7-oxycycloalkenyl, C5 cycloalkenyl -7-oxy, aryloxy, heteroaryloxy, C 1-4 alkyl sulfinyl, C 1-4 alkyl sulfonyl, C 3-7 cycloalkyl sulfanyl, C 3-7 cycloalkyl sulfinyl, cycloalkyl C3-7-sulfonyl, C5-7-cycloalkenyl sulfanyl, C5-7-sulfinyl cycloalkenyl, C5-7-sulfonyl cycloalkenyl, arylsulfanyl, arylsulfinyl, arylsulfonyl, heteroarylsulfanyl, heteroarylsulfinyl, heteroarylsulfonyl, cyano or nitro groups mentioned in the above, be substituted once or several times by fluorine or chlorine, and the alkynyl and alkenyl groups mentioned above may be substituted once or twice by the same or different L1 moieties, and the cycloalkyl and cycloalkenyl rings may be mentioned above, be substituted once or twice, independently of each other, by substituents selected from fluorine and C1-3alkyl, and may in the above-mentioned cycloalkyl and alkenyl rings be substituted once or two methylene groups once or twice, independently of each other, by O, S, CO, SO, SO2 or NRN; B means tri- (C1-4 alkyl) silyl-C1-6 alkyl, C2-6-1-yl alkyne, C2-6-1-yl alkyne, amino, C1-3-amino alkyl, di- (C1- alkyl 3) amino, pyrrolidin-1-yl, pyrrolidin-2-on-1-yl, piperidin-1-yl, piperidin-2-on-1-yl, morpholin-4-yl, morpholin-3-on-4- ilo, piperazin-1-yl, 4- (C1-3 alkyl) piperazin-1-yl, arylcarbonylamino, heteroarylcarbonylamino, nitro, C3-10-cycloalkyl, C5-10-oxycycloalkenyl, C3-10-sulfanyl, cycloalkyl C3-10-sulfinyl, cycloalkyl C3-10-sulfonyl, cycloalkenyl C5-10-sulfanyl, cycloalkenyl C5-10-sulfinyl, cycloalkenyl C5-10-sulfonyl, arylsulfanyl, arylsulfinyl, heteroarylsulfanyl or heteroarylsulfinyl, the alkynyl and alkenyl groups being mentioned the foregoing being substituted once or several times by fluorine or chlorine, and the alkynyl and alkenyl groups mentioned above being able to be substituted once or twice by the same or different L1 moieties, the cycloalkyl and cycloalkenyl rings mentioned herein may be that It may be substituted fluorine or chlorine, independently of each other, once or twice by substituents selected from fluorine and C1-3alkyl, and may in the above-mentioned cycloalkyl and alkenyl rings, one or two groups of methylene be substituted, independently of each other, by O, S, CO, SO, SO2 or NRN; RN is H, C1-4 alkyl, C1-4 alkylcarbonyl or C1-4 alkyl sulfonyl; L1 independently of each other, selected from the group consisting of hydroxy, cyano, nitro, C3-7 cycloalkyl, aryl, heteroaryl, C1-4alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aminocarbonyl, C1-4alkylcarbonyl-, di-amino (C1-3 alkyl) carbonyl, pyrrolidin-1-yl-carbonyl, piperidin-1-yl-carbonyl, morpholin-4-yl-carbonyl, arylaminocarbonyl, heteroarylaminocarbonyl, C1-4 alkoxycarbonyl, C1-3 arylalkoxy -carbonyl, C1-3 heteroarylalkoxycarbonyl, C1-4-oxy alkyl, aryloxy, heteroaryloxy, C1-4 alkyl sulfanyl, arylsulfanyl, heteroarylsulfanyl, C1-4 alkyl sulfinyl, arylsulfinyl, heteroarylsulfinyl, C1-4 alkyl sulfonyl, arylsulfonyl and heteroarylsulfonyl; and L2 independently of each other, selected from the group consisting of fluorine, chlorine, bromine, iodine, C1-3 alkyl, difluoromethyl, trifluoromethyl, C1-3 alkoxy, difluoromethoxy, trifluoromethoxy and cyano; and R6, R7a, R7b, R7c have, independently of one another, a meaning selected from the hydrogen group, (C1-18 alkyl) carbonyl, (C1-18 alkyl) oxycarbonyl, arylcarbonyl and aryl- (C1-3 alkyl ) -carbonyl, the aryl groups mentioned in the definition of the named residues mentioned above being understood as phenyl or naphthyl groups, which, independently of each other, may be substituted once or twice by the same or different L2 residues ; and the heteroaryl groups mentioned in the definition of the moieties named above should be understood as a pyrrolyl, furanyl, thienyl, pyridyl, indolyl, benzofuranyl, benzothiophenyl, quinolinyl, isoquinolinyl or tetrazolyl group, or a pyrrolyl, furanyl group, thienyl or pyridyl, in which one or two methine groups are replaced by nitrogen atoms, or an indolyl, benzofuranyl, benzothiophenyl, quilnolinyl or isoquinolinyl group, in which one to three methine groups are replaced by nitrogen atoms, whereby the heteroaryl groups mentioned above, be substituted, independently of each other, once or twice with the same or different L2 moieties; being able, as soon as something different is not indicated, the alkyl groups mentioned above, being straight or branched chains, their tautomers, their stereoisomers, their mixtures and their salts. The compounds according to the present are suitable for the treatment of metabolic diseases.
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