Nitrogen heterocycle derivatives as proteasome modulators
AssigneesInstitut National De La Sante Et De La Recherche Medicale (Inserm), Centre National De La Recherche Scientifique, Universite Rennes 1, Universite Paris Diderot, Universite Pierre et Marie Curie
InventorsBruno VILLOUTREIX, Michele REBOUD-RAVAUX, Nicolas BASSE, Joelle VIDAL, Matthieu MONTES
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Abstract
A method for treating and/or ameliorating and/or preventing a disease or a disorder, the method comprising administering to an individual in need thereof at least one nitrogen heterocycle derivative of formula (I): The at least one nitrogen heterocycle derivative may also be used as a proteasome activity modulator in the manufacture of a pharmaceutical composition intended to prevent and/or treat a disease condition mediated by the proteasome activity.
Claims27
A method for treating and/or ameliorating and/or preventing a disease or a disorder, the method comprising administering to an individual in need thereof an effective amount of a medicament comprising at least one nitrogen heterocycle derivative of formula (I):
- wherein Het represents a triazole or an oxadiazole radical, optionally substituted with one or more linear or branched, saturated or unsaturated, C1-C4 alkyl group;
- Ar1 represents a C6-C10 aryl group substituted with at least one R group selected from the group consisting of:
- H,
- a halogen group,
- a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkyl group,
- a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkoxy group, and
- a phenoxy group;
- A represents:
- a covalent bond,
- a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkylene group, or
- *-X—C(R4R6)-□,
- with *- representing a covalent bond with Ar1, -□ representing a covalent bond with —C(O)—, X representing a linear or branched, saturated or unsaturated, C1-C5 alkylene group, or a heteroatom, and R4 and R6 being, independently of each other, selected from the group consisting of H and a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkyl group;
- B represents a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkylene group, optionally substituted with one or more C1-C5 hydroxyalkyl group(s), or a C6-C10 arylene group;
- R3 represents H or a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkyl group;
- and
- Z represents —(R5)n—(Ar2)m, with n and m representing, independently of each other, 0 or 1, provided that at least one of n or m is 1, where
- R5 represents a linear, branched or cyclic, saturated or unsaturated C1-C5 alkyl or alkylamido group, optionally comprising one or more heteroatom(s) chosen among O, N or S and being optionally substituted with one or more halogen atom(s), and
- Ar2 represents a C5-C10 aryl group substituted with at least one R group.
A method for the prevention and/or treatment of skin aging, the method comprising administering to an individual in need thereof an effective amount of a cosmetic composition comprising at least one nitrogen heterocycle derivative of formula (I):
- wherein Het represents a triazole or an oxadiazole radical, optionally substituted with one or more linear or branched, saturated or unsaturated, C1-C4 alkyl group;
- Ar1 represents a C6-C10 aryl group substituted with at least one R group selected from the group consisting of:
- H,
- a halogen group,
- a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkyl group,
- a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkoxy group, and
- a phenoxy group;
- A represents:
- a covalent bond,
- a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkylene group, or
- *-X—C(R4R6)-□,
- with *- representing a covalent bond with Ar1, -□ representing a covalent bond with —C(O)—, X representing a linear or branched, saturated or unsaturated, C1-C5 alkylene group, or a heteroatom, and R4 and R6 being, independently of each other, selected from the group consisting of H and a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkyl group;
- B represents a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkylene group, optionally substituted with one or more C1-C5 hydroxyalkyl group(s), or a C6-C10 arylene group;
- R3 represents H or a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkyl group;
- and
- Z represents —(R5)n—(Ar2)m, with n and m representing, independently of each other, 0 or 1, provided that at least one of n or m is 1, where
- R5 represents a linear, branched or cyclic, saturated or unsaturated C1-C5 alkyl or alkylamido group, optionally comprising one or more heteroatom(s) chosen among O, N or S and being optionally substituted with one or more halogen atom(s), and
- Ar2 represents a C5-C10 aryl group substituted with at least one R group.
A kit comprising (i) at least one nitrogen heterocycle derivative of formula (I):
- wherein Het represents a triazole or an oxadiazole radical, optionally substituted with one or more linear or branched, saturated or unsaturated, C1-C4 alkyl group;
- Ar1 represents a C6-C10 aryl group substituted with at least one R group selected from the group consisting of:
- H,
- a halogen group,
- a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkyl group,
- a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkoxy group, and
- a phenoxy group;
- A represents:
- a covalent bond,
- a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkylene group, or
- *-X—C(R4R6)-□,
- with *- representing a covalent bond with Ar1, -□ representing a covalent bond with —C(O)—, X representing a linear or branched, saturated or unsaturated, C1-C5 alkylene group, or a heteroatom, and R4 and R6 being, independently of each other, selected from the group consisting of H and a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkyl group;
- B represents a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkylene group, optionally substituted with one or more C1-C5 hydroxyalkyl group(s), or a C6-C10 arylene group;
- R3 represents H or a linear, branched or cyclic, saturated or unsaturated, C1-C5 alkyl group;
- and
- Z represents —(R5)n—(Ar2)m, with n and m representing, independently of each other, 0 or 1, provided that at least one of n or m is 1, where
- R5 represents a linear, branched or cyclic, saturated or unsaturated C1-C5 alkyl or alkylamido group, optionally comprising one or more heteroatom(s) chosen among O, N or S and being optionally substituted with one or more halogen atom(s), and
- Ar2 represents a C6-C10 aryl group substituted with at least one R group;
- and (ii) at least one agent useful for the prevention and/or the treatment of a cancer condition, said agent being different from said nitrogen heterocycle derivative of formula (I).
Dependencies are inferred from the claim text.