Oleic acid derivatives, pharmaceutical composition or food composition comprising said oleic acid derivatives, and their uses
AssigneesUniversité De Bourogne, Inserm (Institut National De La Sante Et De La Recherche Medicale)
InventorsNaim Khan, Sylvain Juge, Aziz Hichami, Jérôme Bayardon, Floriane Mangin, Amira Khan
Life of this patent
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Abstract
Disclosed is an oleic acid derivative including a hydrophobic part C17H33 linked to a particular polar head part “A”, especially for use as a medicament, for instance, for the treatment of a disorder caused by the GPR120 receptor and/or the CD36 receptor, including administering to a subject in need thereof a therapeutically effective amount of the oleic acid derivative or of the pharmaceutical composition. Also disclosed is the use of the oleic acid derivative as a food composition.
Claims19
An oleic acid derivative of Formula (Z)-(I) or (E)-(I):
- wherein group A is selected from A1 to A3 below:
- wherein R1 and R2 are each independently selected from the group consisting of ·H or a saturated or unsaturated, straight or branched alkyl group containing 1 to 8 carbon atoms, or R1 and R2 are linked together to form a divalent radical of formula —R1-R2—, wherein —R1-R2— is —CH2—CH2— or —(CH2)3—;
- with the proviso that:
- when R1 or R2═H, respectively R2 or R1 is different from H and from a straight alkyl group containing 2 or 8 carbon atoms, and
- when R1 or R2═—CH2CH3 or —CH(CH3)2 or —(CH2)3CH3, R1 and R2 are not identical;
- R3 is independently selected from the group consisting of
- wherein R4 is independently selected from the group consisting of a saturated or unsaturated, straight or branched alkyl group containing 1 to 4 carbon atoms, n is an integer selected from 1 to 4, and n′ is an integer that is equal to 0 or 1;
- “*” is the carbon atom which is attached to the oxygen atom of the A2 group;
- R12 is independently selected from the group consisting of a saturated or unsaturated, straight or branched alkyl group containing 1 to 4 carbon atoms, or an aromatic group or —CO2R13 in which R13 is a saturated alkyl group containing 1 to 4 carbon atoms;
- R14, R15, R16 are each independently selected from the group consisting of H or CH3;
- R5, R6 and R7 are each independently selected from the group consisting of H or a saturated or unsaturated, straight or branched alkyl group containing 1 to 4 carbon atoms, or —CO2R8 in which R8 is a saturated or unsaturated, straight or branched alkyl group containing 1 to 4 carbon atoms, with the proviso that when R7 is H or CH3, at least one of R5 and R6 is different from H and CH3;
- or a pharmaceutically acceptable salt or food quality acceptable salt thereof.
A medicament comprising at least an oleic acid derivative of Formula (Z)-(I) or (E)-(I):
- wherein group A is selected from A1 to A3 below:
- wherein
- R1 and R2 are each independently selected from the group consisting of H or a saturated or unsaturated, straight or branched alkyl group containing 1 to 8 carbon atoms, or R1 and R2 are linked together to form a divalent radical of formula —R1-R2— wherein —R1-R2— is —CH2—CH2— or —(CH2)3—;
- with the proviso that:
- when R1 or R2═H, respectively R2 or R1 is different from H and from a straight alkyl group containing 2 or 8 carbon atoms and
- when R1 or R2═—CH2CH3 or —CH(CH3)2 or —(CH2)3CH3, R1 and R2 are not identical,
- R3 is independently selected from the group consisting of:
- wherein R4 is independently selected from the group consisting of a saturated or unsaturated, straight or branched alkyl group containing 1 to 4 carbon atoms, n is an integer selected from 1 to 4, and n′ is an integer that is equal to 0 or 1;
- “*” is the carbon atom which is attached to the oxygen atom of the A2 group;
- R12 is independently selected from the group consisting of an alkyl group containing 1 to 4 carbon atoms, or an aromatic group or —CO2R13 in which R13 is a saturated alkyl group containing 1 to 4 carbon atoms,
- R14, R15, R16 are each independently selected from the group consisting of H or CH3;
- or R14═H or CH3 and R15=R16═H;
- R5, R6 and R7 are each independently selected from the group consisting of H or a saturated or unsaturated, straight or branched alkyl group containing 1 to 4 carbon atoms, or —CO2R8 in which R8 is a saturated or unsaturated, straight or branched alkyl group containing 1 to 4 carbon atoms, with the proviso that when R7 is H or CH3, at least one of R5 and R6 is different from H and CH3;
- or a pharmaceutically acceptable salt or food quality acceptable salt thereof.
Dependencies are inferred from the claim text.