Flavagline derivatives
AssigneePierre Fabre Medicament
InventorsFrédéric Marion, El Bachir Kaloun, Frédéric Lieby-Muller, Michel Perez, Jean-Philippe Annereau, Laurent Creancier
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Abstract
The invention relates to compounds of the following general formula (I) in the form of one of the enantiomers thereof or a mixture of the enantiomers thereof, and the pharmaceutically acceptable salts and/or solvates thereof, especially for the use thereof as a medicament, more specifically in cancer treatment. The invention also relates to pharmaceutical compositions containing same and to the methods for the production thereof.
Claims11
A method for treating cancer, comprising administering to a person in need of said treatment an effective dose of a compound of the following formula (I):
- in the form of one of the enantiomers thereof or a mixture of the enantiomers thereof,
- or a pharmaceutically acceptable salt and/or solvate thereof,
- wherein:
- the solvate is an ethanolate or hydrate,
- represents a single bond or a double bond,
- n represents an integer between 1 and 10,
- R1 represents CO2R10, CONH2, NR11R12, NR13COR14, NR15CONR16R17, NR18CSNR19R20, NR21SO2R22, NR23CO2R24 or an optionally substituted heteroaryl,
- R2 represents OH, or
- R1 and R2 together form, with the carbon atoms which bear them, an optionally substituted heterocycle, the optionally substituted heterocycle not being:
- carbon 1 designating the carbon atom bearing the group R1 and carbon 2 designating the carbon atom bearing the group R2,
- R3 represents H, OR25, CHOHCH2OH, CHO, N3, NR26R27, CO2R28, CONR29R30, NR38COR39, (O(CH2)mO(CH2)p)r(CH2)qR31, (NR32(CH2)wNR33(CH2)x)y(CH2)zR34, ONR84R85, optionally substituted aryl or optionally substituted heteroaryl,
- R4 is absent when represents a double bond and R4 represents H or OH when represents a single bond,
- R10 to R30, R32, R33, R38 and R39 represent, independently of each other, H or a (C1-C6)alkyl, aryl, aryl-(C1-C6)alkyl or (C1-C6)alkylaryl group, said (C1-C6)alkyl, aryl, aryl-(C1-C6)alkyl or (C1-C6)alkylaryl group being optionally substituted by one or more groups selected from (C1-C6)alkyl, OR35 and NR36R37, or
- R11 and R12, or R16 and R17, or R19 and R20, or R26 and R27, or R29 and R30, together form, with the nitrogen atom which bears them, an optionally substituted nitrogen-containing heterocycle,
- R31 and R34 represent, independently of each other, H, OR35, NR36R37 or a (C1-C6)alkyl, aryl, aryl-(C1-C6)alkyl, ONR86R87 or (C1-C6)alkylaryl group, said group being optionally substituted by one or more groups selected from (C1-C6)alkyl, OR35 and NR36R37,
- R35 to R37 and R84 to R87 represent, independently of each other, H or a (C1-C6)alkyl, aryl or aryl-(C1-C6)alkyl group,
- Ra represents a halogen atom, CN or a (C1-C6)alkoxy group,
- Rb represents H or a (C1-C6)alkoxy group, or
- Ra and Rb together form an —OCH2O— chain, and
- m, p, r, q, w, x, y, and z represent, independently of each other, an integer between 1 and 4, provided that when R1 represents CO2R10 or CONH2, R3 represents CHOHCH2OH, CHO, N3, NR26R27, CO2R28, CONR29R30, NR38COR39, (O(CH2)mO(CH2)p)r(CH2)qR31 or (NR32(CH2)wNR33(CH2)x)y(CH2)zR34.
Dependencies are inferred from the claim text.