Hydroxyester derivatives, a process for their preparation and pharmaceutical compositions containing them

A method of treating a condition requiring a pro-apoptotic agent, including cancer (including cancer of the bladder, brain, breast and uterus, chronic lymphoid leukaemias, cancer of the colon, cesophagus and liver, lymphoblastic leukaemias, acute myeloid leukaemias, lymphomas, melanomas, malignant haemopathies, myelomas, ovarian cancer, non-small-cell lung cancer, prostate cancer, pancreatic cancer and small-cell lung cancer), auto-immune diseases, and immune system diseases, in a subject in need thereof, comprising administration of a compound of formula (VIA):

• alone or in combination with one or more pharmaceutically excipients, wherein:
• R2′, R3′, R4′ and R5′ independently of one another represent a halogen atom, a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a hydroxy(C1-C6)alkyl group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a cyano group, a nitro group, -alkyl(C0-C6)—NR9R9′, —O-alkyl(C1-C6)—NR9R9′, —O-alkyl(C1-C6)—R10, —C(O)—OR9, —O—C(O)—R9, —C(O)—NR9R9′, —NR9—C(O)—R9′, —NR9—C(O)—OR9′, -alkyl(C1-C6)—NR9—C(O)—R9′, —SO2—NR9R9′, —SO2-alkyl(C1-C6),
• T represents a (C1-C6)alkyl group, a (C1-C6)carbonyloxy(C1-C6)alkyl group or a di(C1-C6)alkylaminocarbonyl(C1-C6)alkyl group,
• A represents the group
• wherein 1 is linked to the oxygen atom and 2 is linked to the phenyl ring,
• R1 represents a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a hydroxy(C1-C6)alkyl group, a cyano group, —NR11R11′, -Cy6, or a halogen atom,
• R6 and R7 independently of one another represent a hydrogen atom, a halogen atom, a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a cyano group, a nitro group, -alkyl(C0-C6)—NR9R9′, —O-alkyl(C1-C6)—NR9R9′, —O-Cy1, -alkyl(C0-C6)-Cy1, -alkenyl(C2-C6)-Cy1, -alkynyl(C2-C6)-Cy1, —O-alkyl(C1-C6)—R10, —C(O)—OR9, —O—C(O)—R9, —C(O)—NR9R9′, —NR9—C(O)—R9′, —NR9—C(O)—OR9′, -alkyl(C1-C6)—NR9—C(O)—R9′, —SO2—NR9R9′, —SO2-alkyl(C1-C6), or the substituents of the pair (R6, R7), when grafted onto two adjacent carbon atoms, together with the carbon atoms carrying them, form an aromatic or non-aromatic ring having from 5 to 7 ring members, which ring may contain from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen, wherein the resulting ring may be substituted by a group selected from the group consisting of a linear or branched (C1-C6)alkyl group, —NR11R11′, -alkyl(C0-C6)-Cy1, and oxo,
• R8 represents a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, -Cy3, -alkyl(C1-C6)-Cy3, -alkenyl(C2-C6)-Cy3, -alkynyl(C2-C6)-Cy3, -Cy3-Cy4, -alkynyl(C2-C6)—O-Cy3, -Cy3-alkyl(C0-C6)—O-alkyl(C0-C6)-Cy4, a halogen atom, a cyano group, —C(O)—R12, or —C(O)—NR12R12′,
• R9 and R9′ independently of one another represent a hydrogen atom, a linear or branched (C1-C6)alkyl group, -alkyl(C0-C6)-Cy1,
• or the substituents of the pair (R9, R9′), together with the nitrogen atom carrying them, form an aromatic or non-aromatic ring having from 5 to 7 ring members, which ring may contain, in addition to the nitrogen atom, from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen, wherein the nitrogen may be substituted by a hydrogen atom or a linear or branched (C1-C6)alkyl group and wherein one or more of the carbon atoms of the possible substituents, may be deuterated,
• R10 represents -Cy1, -Cy1-alkyl(C0-C6)-Cy2, -Cy1-alkyl(C0-C6)—O-alkyl(C0-C6)-Cy2, -Cy1-alkyl(C0-C6)—NR9-alkyl(C0-C6)-Cy2, -Cy1-Cy2-O-alkyl(C0-C6)-Cy5, —C(O)—NR9R9′, —NR9R9′, —OR9, —NR9—C(O)—R9′, —O-alkyl(C1-C6)—OR9, —SO2—R9, —C(O)—OR9, or —NH—C(O)—NH—R7,
• R11, R11′, R12 and R12′, independently of one another represent a hydrogen atom or an optionally substituted linear or branched (C1-C6)alkyl group,
• R13 represents a hydrogen atom, a hydroxy group, or a hydroxy(C1-C6)alkyl group,
• Cy1, Cy2, Cy3, Cy4, Cy5 and Cy6, independently of one another, represent a cycloalkyl group, a heterocycloalkyl group, an aryl group or a heteroaryl group, and
• n is an integer equal to 0 or 1,
• wherein:
• “aryl” means a phenyl, naphthyl, biphenyl, indanyl or indenyl group,
• “heteroaryl” means any mono- or bi-cyclic group composed of from 5 to 10 ring members, having at least one aromatic moiety and containing from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen,
• “cycloalkyl” means any mono- or bi-cyclic non-aromatic carbocyclic group containing from 3 to 10 ring members,
• “heterocycloalkyl” means any mono- or bi-cyclic non-aromatic carbocyclic group containing from 3 to 10 ring members, and containing from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen, which may include fused, bridged or spiro ring systems,
• wherein the aryl, heteroaryl, cycloalkyl and heterocycloalkyl groups so defined and the alkyl, alkenyl, alkynyl, alkoxy groups, may be substituted by from 1 to 4 groups selected from optionally substituted linear or branched (C1-C6)alkyl, optionally substituted linear or branched (C2-C6)alkenyl group, optionally substituted linear or branched (C2-C6)alkynyl group, optionally substituted linear or branched (C1-C6)alkoxy, optionally substituted (C1-C6)alkyl-S—, hydroxy, oxo (or N-oxide where appropriate), nitro, cyano, —C(O)—OR′, —O—C(O)—R′, —C(O)—NR′R″, —NR′R″, —(C═NR′)—OR″, linear or branched (C1-C6)polyhaloalkyl, trifluoromethoxy, or halogen, wherein R′ and R″, independently of one another, represent a hydrogen atom or an optionally substituted linear or branched (C1-C6)alkyl group, and wherein one or more of the carbon atoms of the preceding possible substituents, may be deuterated,
• its enantiomers, diastereoisomers and atropisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.

A method of treating a condition requiring a pro-apoptotic agent, including cancer (including cancer of the bladder, brain, breast and uterus, chronic lymphoid leukaemias, cancer of the colon, oesophagus and liver, lymphoblastic leukaemias, acute myeloid leukaemias, lymphomas, melanomas, malignant haemopathies, myelomas, ovarian cancer, non-small-cell lung cancer, prostate cancer, pancreatic cancer and small-cell lung cancer), auto-immune diseases, and immune system diseases, in a subject in need thereof, comprising administration of a compound of formula (VIIA):

• alone or in combination with one or more pharmaceutically excipients, wherein:
• R2′, R3′, R4′ and R5′ independently of one another represent a halogen atom, a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a hydroxy(C1-C6)alkyl group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a cyano group, a nitro group, -alkyl(C0-C6)—NR9R9′, —O-alkyl(C1-C6)—NR9R9′, —O-alkyl(C1-C6)—R10, —C(O)—OR9, —O—C(O)—R9, —C(O)—NR9R9′, —NR9—C(O)—R9′, —NR9—C(O)—OR9′, -alkyl(C 1-C6)—NR9—C(O)—R9′, —SO2—NR9R9′, —SO2-alkyl(C 1-C6),
• A represents the group
• wherein 1 is linked to the oxygen atom and 2 is linked to the phenyl ring,
• R1 represents a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a hydroxy(C1-C6)alkyl group, a cyano group, —NR11R11′, -Cy6, or a halogen atom,
• R6 and R7 independently of one another represent a hydrogen atom, a halogen atom, a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a cyano group, a nitro group, -alkyl(C0-C6)—NR9R9′, —O-alkyl(C1-C6)—NR9R9′, —O-Cy1, -alkyl(C0-C6)-CY1, -alkenyl(C2-C6)-Cy1, -alkynyl(C2-C6)-Cy1, —O-alkyl(C1-C6)—R10, —C(O)—OR9, —O—C(O)—R9, —C(O)—NR9R9′, —NR9—C(O)—R9′, —NR9—C(O)—OR9′, -alkyl(C1-C6)—NR9—C(O)—R9′, —SO2—NR9R9′, —SO2-alkyl(C1-C6),
• or the substituents of the pair (R6, R7), when grafted onto two adjacent carbon atoms, together with the carbon atoms carrying them, form an aromatic or non-aromatic ring having from 5 to 7 ring members, which ring may contain from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen, wherein the resulting ring may be substituted by a group selected from the group consisting of a linear or branched (C1-C6)alkyl group, —NR11R11′, -alkyl(C0-C6)-Cy1, and oxo,
• R8 represents a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, -Cy3, -alkyl(C1-C6)-Cy3, -alkenyl(C2-C6)-Cy3, -alkynyl(C2-C6)-Cy3, -Cy3-Cy4, -alkynyl(C2-C6)—O-Cy3, -Cy3-alkyl(C0-C6)—O-alkyl(C0-C6)-Cy4, a halogen atom, a cyano group, —C(O)—R12, or —C(O)—NR12R12′,
• R9 and R9′ independently of one another represent a hydrogen atom, a linear or branched (C1-C6)alkyl group, -alkyl(C0-C6)-Cy1,
• or the substituents of the pair (R9, R9′), together with the nitrogen atom carrying them, form an aromatic or non-aromatic ring having from 5 to 7 ring members, which ring may contain, in addition to the nitrogen atom, from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen, wherein the nitrogen may be substituted by a hydrogen atom or a linear or branched (C1-C6)alkyl group and wherein one or more of the carbon atoms of the possible substituents, may be deuterated,
• R10 represents -Cy1, -Cy1-alkyl(C0-C6)-Cy2, -Cy1-alkyl(C0-C6)—O-alkyl(C0-C6)-Cy2, -Cy1-alkyl(C0-C6)—NR9-alkyl(C0-C6)-Cy2, -Cy1-Cy2-O-alkyl(C0-C6)-Cy5, —C(O)—NR9R9′, —NR9R9′, —OR9, —NR9—C(O)—R9′, —O-alkyl(C1-C6)—OR9, —SO2—R9, —C(O)—OR9, or —NH—C(O)—NH—R7,
• R11, R11′, R12 and R12′, independently of one another represent a hydrogen atom or an optionally substituted linear or branched (C1-C6)alkyl group,
• R13 represents a hydrogen atom, a hydroxy group, or a hydroxy(C1-C6)alkyl group,
• Cy1, Cy2, Cy3, Cy4, Cy5 and Cy6, independently of one another, represent a cycloalkyl group, a heterocycloalkyl group, an aryl group or a heteroaryl group, and
• n is an integer equal to 0 or 1,
• wherein:
• “aryl” means a phenyl, naphthyl, biphenyl, indanyl or indenyl group,
• “heteroaryl” means any mono- or bi-cyclic group composed of from 5 to 10 ring members, having at least one aromatic moiety and containing from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen,
• “cycloalkyl” means any mono- or bi-cyclic non-aromatic carbocyclic group containing from 3 to 10 ring members,
• “heterocycloalkyl” means any mono- or bi-cyclic non-aromatic carbocyclic group containing from 3 to 10 ring members, and containing from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen, which may include fused, bridged or spiro ring systems,
• wherein the aryl, heteroaryl, cycloalkyl and heterocycloalkyl groups so defined and the alkyl, alkenyl, alkynyl, alkoxy groups, may be substituted by from 1 to 4 groups selected from optionally substituted linear or branched (C1-C6)alkyl, optionally substituted linear or branched (C2-C6)alkenyl group, optionally substituted linear or branched (C2-C6)alkynyl group, optionally substituted linear or branched (C1-C6)alkoxy, optionally substituted (C1-C6)alkyl-S—, hydroxy, oxo (or N-oxide where appropriate), nitro, cyano, —C(O)—OR′, —O—C(O)—R′, —C(O)—NR′R″, —NR′R″, —(C═NR′)—OR″, linear or branched (C1-C6)polyhaloalkyl, trifluoromethoxy, or halogen, wherein R′ and R″, independently of one another, represent a hydrogen atom or an optionally substituted linear or branched (C1-C6)alkyl group, and wherein one or more of the carbon atoms of the preceding possible substituents, may be deuterated,
• its enantiomers, diastereoisomers and atropisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.

A method of treating a condition requiring a pro-apoptotic agent, including cancer (including cancer of the bladder, brain, breast and uterus, chronic lymphoid leukaemias, cancer of the colon, oesophagus and liver, lymphoblastic leukaemias, acute myeloid leukaemias, lymphomas, melanomas, malignant haemopathies, myelomas, ovarian cancer, non-small-cell lung cancer, prostate cancer, pancreatic cancer and small-cell lung cancer), auto-immune diseases, and immune system diseases, in a subject in need thereof, comprising administration of a compound of formula (VIB):

• alone or in combination with one or more pharmaceutically excipients, wherein:
• R5′ represents a halogen atom, a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a hydroxy(C1-C6)alkyl group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a cyano group, a nitro group, -alkyl(C0-C6)—NR9R9′, —O-alkyl(C1-C6)—NR9R9′, —O-alkyl(C1-C6)—R10, —C(O)—OR9, —O—C(O)—R9, —C(O)—NR9R9′, —NR9—C(O)—R9′, —NR9—C(O)—OR9′, -alkyl(C1-C6)—NR9—C(O)—R9′, —SO2—NR9R9′, —SO2-alkyl(C1-C6),
• T represents a (C1-C6)alkyl group, a (C1-C6)carbonyloxy(C1-C6)alkyl group or a di(C1-C6)alkylaminocarbonyl(C1-C6)alkyl group,
• A represents the group
• wherein 1 is linked to the oxygen atom and 2 is linked to the phenyl ring,
• R1 represents a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a hydroxy(C1-C6)alkyl group, a cyano group, —NR11R11′, -Cy6, or a halogen atom,
• R3 represents a hydrogen atom, a halogen atom, a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a hydroxy(C1-C6)alkyl group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a cyano group, a nitro group, -alkyl(C0-C6)—NR9R9′, —O-alkyl(C1-C6)—NR9R9′, —O-alkyl(C1-C6)—R10, —C(O)—OR9, —O—C(O)—R9, —C(O)—NR9R9′, —NR9—C(O)—R9′, —NR9—C(O)—OR9′, -alkyl(C1-C6)—NR9—C(O)—R9′, —SO2—NR9R9′, —SO2-alkyl(C1-C6),
• R6 and R7 independently of one another represent a hydrogen atom, a halogen atom, a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a cyano group, a nitro group, -alkyl(C0-C6)—NR9R9′, —O-alkyl(C1-C6)—NR9R9′, —O-Cy1, -alkyl(C0-C6)-Cy1, -alkenyl(C2-C6)-Cy1, -alkynyl(C2-C6)-Cy1, —O-alkyl(C1-C6)—R10, —C(O)—OR9, —O—C(O)—R9, —C(O)—NR9R9′, —NR9—C(O)—R9′, —NR9—C(O)—OR9′, -alkyl(C1-C6)—NR9—C(O)—R9′, —SO2—NR9R9′, —SO2-alkyl(C1-C6),
• or the substituents of the pair (R6, R7), when grafted onto two adjacent carbon atoms, together with the carbon atoms carrying them, form an aromatic or non-aromatic ring having from 5 to 7 ring members, which ring may contain from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen, wherein the resulting ring may be substituted by a group selected from the group consisting of a linear or branched (C1-C6)alkyl group, —NR11R11′, -alkyl(C0-C6)-Cy1, and oxo,
• R8 represents a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, -Cy3, -alkyl(C1-C6)-Cy3, -alkenyl(C2-C6)-Cy3, -alkynyl(C2-C6)-Cy3, -Cy3-Cy4, -alkynyl(C2-C6)—O-Cy3, -Cy3-alkyl(C0-C6)—O-alkyl(C0-C6)-Cy4, a halogen atom, a cyano group, —C(O)—R12, or —C(O)—NR12R12′,
• R9 and R9′ independently of one another represent a hydrogen atom, a linear or branched (C1-C6)alkyl group, -alkyl(C0-C6)-Cy1,
• or the substituents of the pair (R9, R9′), together with the nitrogen atom carrying them, form an aromatic or non-aromatic ring having from 5 to 7 ring members, which ring may contain, in addition to the nitrogen atom, from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen, wherein the nitrogen may be substituted by a hydrogen atom or a linear or branched (C1-C6)alkyl group and wherein one or more of the carbon atoms of the possible substituents, may be deuterated,
• R10 represents -Cy1, -Cy1-alkyl(C0-C6)-Cy2, -Cy1-alkyl(C0-C6)—O-alkyl(C0-C6)-Cy2, -Cy1-alkyl(C0-C6)—NR9-alkyl(C0-C6)-Cy2, -Cy1-Cy2—O-alkyl(C0-C6)-Cy5, —C(O)—NR9R9′, —NR9R9′, —OR9, —NR9—C(O)—R9′, —O-alkyl(C1-C6)—OR9, —SO2—R9, —C(O)—OR9, or —NH—C(O)—NH—R7,
• R11, R11′, R12 and R12′, independently of one another represent a hydrogen atom or an optionally substituted linear or branched (C1-C6)alkyl group,
• R13 represents a hydrogen atom, a hydroxy group, or a hydroxy(C1-C6)alkyl group,
• Cy1, Cy2, Cy3, Cy4, Cy5 and Cy6, independently of one another, represent a cycloalkyl group, a heterocycloalkyl group, an aryl group or a heteroaryl group, and
• n is an integer equal to 0 or 1,
• wherein:
• “aryl” means a phenyl, naphthyl, biphenyl, indanyl or indenyl group,
• “heteroaryl” means any mono- or bi-cyclic group composed of from 5 to 10 ring members, having at least one aromatic moiety and containing from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen,
• “cycloalkyl” means any mono- or bi-cyclic non-aromatic carbocyclic group containing from 3 to 10 ring members,
• “heterocycloalkyl” means any mono- or bi-cyclic non-aromatic carbocyclic group containing from 3 to 10 ring members, and containing from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen, which may include fused, bridged or spiro ring systems,
• wherein the aryl, heteroaryl, cycloalkyl and heterocycloalkyl groups so defined and the alkyl, alkenyl, alkynyl, alkoxy groups, may be substituted by from 1 to 4 groups selected from optionally substituted linear or branched (C1-C6)alkyl, optionally substituted linear or branched (C2-C6)alkenyl group, optionally substituted linear or branched (C2-C6)alkynyl group, optionally substituted linear or branched (C1-C6)alkoxy, optionally substituted (C1-C6)alkyl-S—, hydroxy, oxo (or N-oxide where appropriate), nitro, cyano, —C(O)—OR′, —O—C(O)—R′, —C(O)—NR′R″, —NR′R″, —(C═NR′)—OR″, linear or branched (C1-C6)polyhaloalkyl, trifluoromethoxy, or halogen, wherein R′ and R″, independently of one another, represent a hydrogen atom or an optionally substituted linear or branched (C1-C6)alkyl group, and wherein one or more of the carbon atoms of the preceding possible substituents, may be deuterated,
• and wherein the substituents of the pair (R1, R5′) are identical,
• its enantiomers, diastereoisomers and atropisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.

A method of treating a condition requiring a pro-apoptotic agent, including cancer (including cancer of the bladder, brain, breast and uterus, chronic lymphoid leukaemias, cancer of the colon, oesophagus and liver, lymphoblastic leukaemias, acute myeloid leukaemias, lymphomas, melanomas, malignant haemopathies, myelomas, ovarian cancer, non-small-cell lung cancer, prostate cancer, pancreatic cancer and small-cell lung cancer), auto-immune diseases, and immune system diseases, in a subject in need thereof, comprising administration of a compound of formula (VIIB):

• alone or in combination with one or more pharmaceutically excipients, wherein:
• R5′ represents a halogen atom, a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a hydroxy(C1-C6)alkyl group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a cyano group, a nitro group, -alkyl(C0-C6)—NR9R9′, —O-alkyl(C1-C6)—NR9R9′, —O-alkyl(C1-C6)—R10, —C(O)—OR9, —O—C(O)—R9, —C(O)—NR9R9′, —NR9—C(O)—R9′, —NR9—C(O)—OR9′, -alkyl(C1-C6)—NR9—C(O)—R9′, —SO2—NR9R9′, —SO2-alkyl(C1-C6),
• A represents the group
• wherein 1 is linked to the oxygen atom and 2 is linked to the phenyl ring,
• R1 represents a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a hydroxy(C1-C6)alkyl group, a cyano group, —NR11R11′, -Cy6, or a halogen atom,
• R3 represents a hydrogen atom, a halogen atom, a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a hydroxy(C1-C6)alkyl group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a cyano group, a nitro group, -alkyl(C0-C6)—NR9R9′, —O-alkyl(C1-C6)—NR9R9′, —O-alkyl(C1-C6)—R10, —C(O)—OR9, —O—C(O)—R9, —C(O)—NR9R9′, —NR9—C(O)—R9′, —NR9—C(O)—OR9′, -alkyl(C1-C6)—NR9—C(O)—R9′, —SO2—NR9R9′, —SO2-alkyl(C1-C6),
• R6 and R7 independently of one another represent a hydrogen atom, a halogen atom, a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a linear or branched (C1-C6)polyhaloalkyl, a hydroxy group, a linear or branched (C1-C6)alkoxy group, a —S—(C1-C6)alkyl group, a cyano group, a nitro group, -alkyl(C0-C6)—NR9R9′, —O-alkyl(C1-C6)—NR9R9′, —O-Cy1, -alkyl(C0-C6)-Cy1, -alkenyl(C2-C6)-Cy1, -alkynyl(C2-C6)-Cy1, —O-alkyl(C1-C6)—R10, —C(O)—OR9, —O—C(O)—R9, —C(O)—NR9R9′, —NR9—C(O)—R9′, —NR9—C(O)—OR9′, -alkyl(C1-C6)—NR9—C(O)—R9′, —SO2—NR9R9′, —SO2-alkyl(C1-C6),
• or the substituents of the pair (R6, R7), when grafted onto two adjacent carbon atoms, together with the carbon atoms carrying them, form an aromatic or non-aromatic ring having from 5 to 7 ring members, which ring may contain from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen, wherein the resulting ring may be substituted by a group selected from the group consisting of a linear or branched (C1-C6)alkyl group, —NR11R11′, -alkyl(C0-C6)-Cy1, and oxo,
• R8 represents a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, -Cy3, -alkyl(C1-C6)-Cy3, -alkenyl(C2-C6)-Cy3, -alkynyl(C2-C6)-Cy3, -Cy3-Cy4, -alkynyl(C2-C6)—O-Cy3, -Cy3-alkyl(C0-C6)—O-alkyl(C0-C6)-Cy4, a halogen atom, a cyano group, —C(O)—R12, or —C(O)—NR12R12′,
• R9 and R9′ independently of one another represent a hydrogen atom, a linear or branched (C1-C6)alkyl group, -alkyl(C0-C6)-Cy1,
• or the substituents of the pair (R9, R9′), together with the nitrogen atom carrying them, form an aromatic or non-aromatic ring having from 5 to 7 ring members, which ring may contain, in addition to the nitrogen atom, from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen, wherein the nitrogen may be substituted by a hydrogen atom or a linear or branched (C1-C6)alkyl group and wherein one or more of the carbon atoms of the possible substituents, may be deuterated,
• R10 represents -Cy1, -Cy1-alkyl(C0-C6)-Cy2, -Cy1-alkyl(C0-C6)—O-alkyl(C0-C6)-Cy2, -Cy1-alkyl(C0-C6)—NR9-alkyl(C0-C6)-Cy2, -Cy1-Cy2—O-alkyl(C0-C6)-Cy5, —C(O)—NR9R9′, —NR9R9′, —OR9, —NR9—C(O)—R9′, —O-alkyl(C1-C6)—OR9, —SO2—R9, —C(O)—OR9, or —NH—C(O)—NH—R7,
• R11, R11′, R12 and R12′, independently of one another represent a hydrogen atom or an optionally substituted linear or branched (C1-C6)alkyl group,
• R13 represents a hydrogen atom, a hydroxy group, or a hydroxy(C1-C6)alkyl group,
• Cy1, Cy2, Cy3, Cy4, Cy5 and Cy6, independently of one another, represent a cycloalkyl group, a heterocycloalkyl group, an aryl group or a heteroaryl group, and
• n is an integer equal to 0 or 1,
• wherein:
• “aryl” means a phenyl, naphthyl, biphenyl, indanyl or indenyl group,
• “heteroaryl” means any mono- or bi-cyclic group composed of from 5 to 10 ring members, having at least one aromatic moiety and containing from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen,
• “cycloalkyl” means any mono- or bi-cyclic non-aromatic carbocyclic group containing from 3 to 10 ring members,
• “heterocycloalkyl” means any mono- or bi-cyclic non-aromatic carbocyclic group containing from 3 to 10 ring members, and containing from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen, which may include fused, bridged or spiro ring systems,
• wherein the aryl, heteroaryl, cycloalkyl and heterocycloalkyl groups so defined and the alkyl, alkenyl, alkynyl, alkoxy groups, may be substituted by from 1 to 4 groups selected from optionally substituted linear or branched (C1-C6)alkyl, optionally substituted linear or branched (C2-C6)alkenyl group, optionally substituted linear or branched (C2-C6)alkynyl group, optionally substituted linear or branched (C1-C6)alkoxy, optionally substituted (C1-C6)alkyl-S—, hydroxy, oxo (or N-oxide where appropriate), nitro, cyano, —C(O)—OR′, —O—C(O)—R′, —C(O)—NR′R″, —NR′R″, —(C═NR′)—OR″, linear or branched (C1-C6)polyhaloalkyl, trifluoromethoxy, or halogen, wherein R′ and R″, independently of one another, represent a hydrogen atom or an optionally substituted linear or branched (C1-C6)alkyl group, and wherein one or more of the carbon atoms of the preceding possible substituents, may be deuterated,
• and wherein the substituents of the pair (R1, R5′) are identical,
• its enantiomers, diastereoisomers and atropisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.