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US 2011/0034402 A1Published application
C-aryl glycoside compounds for the treatment of diabetes and obesity
AssigneeTfchem
InventorGéraldine Castelot-Deliencourt-Godefroy
Life of this patent
Estimating the term…
Abstract
This invention relates to a compound of generic formula (I): (I) as well as a pharmaceutically acceptable salt thereof a tautomer, optical isomer or a mixture of optical isomers in any proportion, in particular a mixture of enantiomers, and particularly a racemate mixture, in particular for use thereof as a drug, notably in the treatment of diabetes.
Claims17
Compound of generic formula (I):
- or a pharmaceutically acceptable salt thereof, a tautomer, an isomer or a mixture of isomers in any proportion, in particular a mixture of enantiomers, and particularly a racemate mixture,
- wherein:
- X represents a hydrogen or a fluorine atom;
- R represents a hydrogen or a fluorine atom or a CH3, CH2F, CH2OH, CH2O SiRaRbRc, CH2OR11, CH2OCOR11, CH2OCO2R11, CH2OCONR12R13, CH2OP(O)(OR14)2 or CH2OSO3R14 group;
- R1 and R2 represent, independently from one another, a fluorine atom or an OH, OSiRaRbRc, OR11, OCOR11, OCO2R11 or OCONR12R13 group;
- R3 represents a hydrogen or fluorine atom or an OH, OSiRaRbRc, OR11, OCOR11, OCO2R11, OCONR12R13, NR12R13 or NR12COR11 group;
- R4 represents a hydrogen atom, an halogen atom or an OH, OSiRaRbRc, OR11, OCOR11, OCO2R11, OCONR12R13, NR12R13, (C1-C6)-alkyl or (C2-C6)-alkenyl group;
- R0 represents a hydrogen or an halogen atom or an OH, OSiRaRbRc, OR11, OCOR11, OCO2R11, OCONR12R13, OP(O)(OR14)2 or OSO3R14 group;
- or R and R1, together with the carbon atoms carrying them, form a cyclic acetal having the following formula:
- and/or (R0 and R1), (R1 and R2), (R2 and R3), and/or (R3 and R4), together with the carbon atoms carrying them, form a cyclic acetal having the following formula:
- and
- A represents an aryl, heteroaryl or aryl-(C1-C6)-alkyl-aryl group, possibly substituted by one or more groups chosen among an halogen atom, a CN, SO2, SiRaRbRc, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C7)-cycloalkyl, 5 to 7 ring-membered heterocycloalkyl, aryl, heteroaryl, aryl-(C1-C6)-alkyl, heteroaryl-(C1-C6)-alkyl, (C1-C6)-alkyl-aryl, (C1-C6)-alkyl-heteroaryl, OR11, COR11, OCOR11, CO2R11, NR12R13, NR12COR11, CONR12R13, SR11, SO2R11, CSR11 and OSO3R11 group,
- the whole being possibly substituted by one or more groups chosen among an halogen atom, an OH, (C1-C6)-alkyl, (C1-C6)-alkoxy, COOH and CHO group;
- with:
- R11 representing a (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C7)-cycloalkyl, 5 to 7 ring-membered heterocycloalkyl, aryl, aryl-(C1-C6)-alkyl or (C1-C6)-alkyl-aryl group, this group being possibly substituted by one or more groups chosen among an halogen atom, an OH, COOH and CHO group;
- R12 and R13 representing, independently from one another, a hydrogen atom or a (C1-C6)-alkyl or aryl-(C1-C6)-alkyl group;
- R14 representing a hydrogen atom or a (C1-C6)-alkyl group;
- Ra, Rb and Rc representing, independently from one another, a (C1-C6)-alkyl, aryl or aryl-(C1-C6)-alkyl group;
- and
- Rd and Re representing, independently from one another, a hydrogen atom or a (C1-C6)-alkyl group;
- with the proviso that when R0 is different from a hydrogen atom, then R4 represents a hydrogen atom, and
- with the proviso that the compound of formula (I) is not the following compound:
19 more elements
Compound of generic formula (III) below:
- or a pharmaceutically acceptable salt thereof, a tautomer, an isomer or a mixture of isomers in any proportions, in particular a mixture of enantiomers, and particularly a racemate mixture, wherein:
- R represents a hydrogen or a fluorine atom or CH3, CH2F, CH2OH, CH2OSiRaRbRc, CH2OR11, CH2OCOR11, CH2OCO2R11, CH2OCONR12R13, CH2OP(O)(OR14)2 or CH2OSO3R14 group;
- R1 and R2 and represent, independently from one another, a fluorine atom or an OH, OSiRaRbRc, OR11, OCOR11, OCO2R11 or OCONR12R13 group;
- R3 represents a hydrogen or fluorine atom or an OH, OSiRaRbRc, OR1', OCOR11, OCO2R11, OCONR12R13, NR12R13 or NR12COR11 group;
- or R and R1, together with the carbon atoms carrying them, form a cyclic acetal having the following formula:
- and/or (R2 and R3) or (R1 and R2), together with the carbon atoms carrying them, form a cyclic acetal having the following formula:
- and
- A represents an aryl or heteroaryl group, possibly substituted by one or more groups chosen among an halogen atom, a CN, SO2, SiRaRbRc, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C7)-cycloalkyl, 5 to 7 ring-membered heterocycloalkyl, aryl, heteroaryl, aryl-(C1-C6)-alkyl, hetero aryl-(C1-C6)-alkyl, (C1-C6)-alkyl-aryl, (C1-C6)-alkyl-heteroaryl, OR11, COR11, OCOR11, CO2R11, NR12R13, NR12COR11, CONR12R13, SR11, SO2R11, CSR11 and OSO3R11 group,
- the whole being possibly substituted by one or more groups chosen among an halogen atom, an OH, (C1-C6)-alkyl, (C1-C6)-alkoxy, COOH and CHO group;
- with:
- R11 representing a (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C7)-cycloalkyl, 5 to 7 ring-membered heterocycloalkyl, aryl, aryl-(C1-C6)-alkyl or (C1-C6)-alkyl-aryl, this group being possibly substituted by one or more groups chosen among an halogen atom, an OH, COOH and CHO group;
- R12 and R13 representing, independently from one another, a hydrogen atom or a (C1-C6)-alkyl or aryl-(C1-C6)-alkyle group;
- R14 representing a hydrogen atom or a (C1-C6)-alkyl group;
- Ra, Rb and Rc representing, independently from one another, a (C1-C6)-alkyl, aryl or aryl-(C1-C6)-alkyl group;
- and
- Rd and Re representing, independently from one another, a hydrogen atom or a (C1-C6)-alkyl group.
13 more elements
Dependencies are inferred from the claim text.