Imidazo[1,5-a] pyridine derivatives, method for preparing same and pharmaceutical compositions containing same

A compound of formula I:

• in which:
• R, present on the 5, 6, 7 or 8 positions of the imidazo[1,5-a]pyridine, represents a hydrogen atom, a halogen atom, an alkyl radical of 1 to 5 carbon atoms, a hydroxyl radical, an alkoxy radical of 1 to 5 carbon atoms, a —COOR6 radical or a radical of formula:
• —NR4R5
• —NH—SO2-Alk
• —NH—CO-Alk
• —NR6—CO2-Alk
• —O-Alk-COOR6
• —O-Alk-NR4R5
• —O—(CH2)n-Ph
• —CO—NR4R5, or
• —CO—NH—CH(R7)—(CH2)m—COOR6
• in which:
• Alk represents an alkyl radical or an alkylene radical of 1 to 5 carbon atoms,
• n represents an integer from 1 to 5,
• m represents an integer from 0 to 4,
• R4 and R5 represent, independently of one another, a hydrogen atom, an alkyl radical of 1 to 5 carbon atoms or a benzyl radical,
• R6 represents a hydrogen atom or an alkyl radical of 1 to 5 carbon atoms,
• R7 represents a hydrogen atom, an alkyl radical of 1 to 5 carbon atoms or a radical of formula:
• -Alk-CONR4R5
• -Alk-OR6
• -Alk-NR4R5
• -Ph, or
• —CH2Ph, and
• Ph represents a phenyl radical optionally substituted by one or more groups chosen from halogen atoms, alkoxy radicals of 1 to 5 carbon atoms and —COOR6 radicals where R6 is as defined above;
• R1 represents a hydrogen atom, a halogen atom, a cyano radical, a —COOR6 radical or a radical of formula:
• —NR4R5
• —NH—SO2-Alk
• —NH—CO—CF3
• —NH—CO-Ph
• —NH—CO-Alk
• —NH—CO2-Alk
• —CONR4R5
• a phenyl radical optionally substituted by one or more groups chosen from halogen atoms, alkyl radicals of 1 to 5 carbon atoms, alkoxy radicals of 1 to 5 carbon atoms and —COOR6 radicals,
• a 5-membered heteroaryl radical comprising a heteroatom chosen from a sulfur atom, an oxygen atom or a nitrogen atom and optionally comprising a second nitrogen atom, said heteroaryl optionally being substituted by one or more groups chosen from halogen atoms, alkyl radicals of 1 to 5 carbon atoms, alkoxy radicals of 1 to 5 carbon atoms and —COOR6 radicals, or
• a 6-membered heteroaryl radical comprising 1 or 2 nitrogen atoms and optionally being substituted by one or more groups chosen from halogen atoms, alkyl radicals of 1 to 5 carbon atoms, alkoxy radicals of 1 to 5 carbon atoms and —COOR6 radicals,
• in which Alk, Ph, R4, R5 and R6 are as defined as above;
• R2 and R3 represent, independently of one another, a hydroxyl radical, an alkoxy radical of 1 to 5 carbon atoms, an amino radical, a —COOR6 radical, a nitro radical or a radical of formula:
• —NR4R5
• —NH—CO-Alk
• —NH—CO-Ph
• —NH—CO2-Alk
• —NH—SO2-Alk
• —CO—NR4R5, or
• —CO—NHOH
• in which Alk, Ph, R4, R5 and R6 are as defined as above;
• or else R2 and R3 together form, with the carbon atoms of the phenyl ring to which they are attached, a 6-membered carbon ring comprising a nitrogen atom and an oxygen heteroatom
• in the base or salt form.