Gem-difluorinated C-isopropylgalactoside derivates

摘要

The present invention concerns compounds of the following formula (I) or a pharmaceutically acceptable salt thereof, a stereoisomer or a mixture of stereoisomers in any proportion, in particular a mixture of enantiomers, and particularly a racemate mixture, in which R represents H, OH or OR19, as well as processes for preparing these compounds and their use as inducer for the transcription of genes under control of the lac promoter.;

主权项

1. A compound of formula (I):or a pharmaceutically acceptable salt thereof, wherein:
R represents H, OH or OR19, R1 represents H, R5, C(O)R5, P(O)(OR6)(OR7), SiR8R9R10, or a O-protecting group, and R2, R3 and R4 represent, independently from one another, H, R11, C(O)R11, SiR12R13R14, or a O-protecting group,
or (R1and R2) form together a chain —CR15R16— linking the oxygen atom carrying them, and/or (R3 and R4) or (R2 and R3) form a chain —CR17R18—linking the oxygen atom carrying them,with:
R5 and R11 representing, independently of one another, a (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C7)cycloalkyl, 5- to 7-membered heterocycloalkyl, aryl, aryl-(C1-C6)alkyl or (C1-C6)alkyl-aryl group, this group being optionally substituted with one or more groups selected from a halogen atom, OH, COOH and CHO, R6 and R7 representing, independently of one another, a hydrogen atom or a (C1-C6)alkyl group, R8, R9, R10, R12, R13, and R14 representing, independently of each other, a (C1-C6)alkyl, aryl or aryl-(C1-C6)alkyl group, and R15, R16, R17, and R18 representing, independently of each other, a hydrogen atom, or a (C1-C6)alkyl, aryl or aryl-(C1-C6)alkyl group, R19 representing COCOOR20, and R20 representing a (C1-C6)alkyl group.