Use of isoquinolones for preparing drugs, novel isoquinolones and method for synthesising same

37) A compound of general formula (I) below:

• in which:
• 1) the bond between carbon 1 and the X group is single or double, the bond between nitrogen 2 and carbon 1 can be single or double
• it being understood that:
• a) when the bond between X and said carbon 1 is double, then the bond between nitrogen 2 and carbon 1 is single:
• and,
• b) when the bond between X and said carbon 1 is single, then the bond between nitrogen 2 and carbon 1 is double and formula I corresponds to an aromatic system of formula I-A below:
• 2) n represents 0 or 1,
• 3) X represents:
• a) when n=1:
• O, S, NH, N—(C1-C6)alkyl,
• b) when n=0:
• OH, OPO3H2, OPO—(O—(C1-C2)alkyl)2, the alkyl being optionally substituted by one or more fluorines, O—(C1-C6)alkyl, in particular OCH3, the alkyl being optionally substituted by one or more fluorines, O(C3-C6)cycloalkyl, NH2, NH—(C1-C6)alkyl, N—[(C1-C6)alkyl]2, NH—(C3-C6)cycloalkyl, N—[(C3-C6)cycloalkyl]2, SH, S—(C1-C6)alkyl, the alkyl being optionally substituted by one or more fluorines, in particular SCH3, S(C3-C6)cycloalkyl, SO3H, NH—CH2-aryl or heteroaryl, OPh, SPh, OCH2Ph, SCH2Ph, the phenyl of these four groups being able to be substituted or not by one or more (C1-C6)alkyls, the alkyl being optionally substituted by one or more fluorines,
• 4) R1 represents:
• H, a halogen, OH, OPO3H2, OPO—(O—(C1-C2)alkyl)2, the alkyl being optionally substituted by one or more fluorines,
• CF3, CH2OR′, R′ representing H or (C1-C6)alkyl, the alkyl being optionally substituted by one or more fluorines, CHO,
• CO2R″, R″ representing H, (C1-C6)alkyl, the alkyl being optionally substituted by one or more fluorines, CONRcRd, CH2SO2NRcRd, CH2NHSO2Rc, Rc and Rd representing independently of each other:
• H, a C1-C6 alkyl, and NRcRd represents an amino acid bound by its amine function, in particular a serine or a threonine, a C3-C6 cycloalkyl, or Rc and Rd represent together a C2-C6 alkyl,
• NO2, N3, ≡, CN, C(═N)NH2, SO3H, SO2NH2, SO2NHCH3, NHSO2CH3, CH2SO2NRcRd, CH2NHSO2Rc, SO2—NRaRb, SO2-imidazole,
• NRaRb, where:
• Ra and Rb represent independently of each other:
• H, a C1-C6 alkyl, a C3-C6 cycloalkyl, or
• Ra is H, a C1-C6 alkyl, a C3-C6 cycloalkyl, and Rb═CORf, COORf or CONRfRf′Rf and Rf′ representing H, a C1-C6 alkyl, a C3-C6 cycloalkyl or an amino acid chain (such as CH(CH2OH)NH2 for serine) Ra and Rb represent together a C2-C6 alkyl,
• Ra and Rb can form a C5 to C7 ring, in particular a pyrrolidine, a piperazine, a morpholine, a thiomorpholine,
• a heteroaryl, substituted or not, in particular a pyridine, an imidazole, an oxazole, a triazole, a pyrrole, a tetrazole.
• 5) R2 represents:
• a phenyl substituted or not by one to three substituents chosen from:
• a halogen, an OH, NHRa,
• ORe, Re representing a benzyl, a methylene triazole, substituted or not, in particular by a C1-C6 alkyl, OPO3H2, OPO—(O—(C1-C2)alkyl)2, the alkyl being optionally substituted by one or more fluorines, an NH2,
• an NH—CORc group in which Rc represents H, a C1-C6 alkyl, a C3-C6 cycloalkyl or an amino acid chain (such as CH(CH2OH)NH2 for serine),
• an O—(C1-C6)alkyl, in particular OCH3, the alkyl being optionally substituted by one or more fluorines,
• an O—COR4 where R1 represents O—(C1-C6)alkyl, or NRiRii, Ri and Rii being able to be C1-C6 alkyl,
• a C2-C4 alkyl group, the alkyl group being optionally substituted by one or more fluorines, a C2-C4 alkenyl group, substituted or not,
• a C2-C4 alkynyl group, substituted or not, in particular by a trimethylsilyl, a tert-butyl, a hydroxy-2-propyl or an isopropyl,
• a heteroaryl, substituted or not, in particular a pyridine, an imidazole, an oxazole, a triazole, a pyrrole, a benzofuran, a thiophene, a benzothiophene, an indole, a cyclohexyl, a piperazine, a morpholine, a thiomorpholine, a piperidine,
• a 4-(NH2—(CH2—CH2O)p)Ph group in which p is an integer from 1 to 6
• 6) R3 represents:
• H, (C1-C6)alkyl, the alkyl being optionally substituted by one or more fluorines, (C3-C6)cycloalkyl, OH, OPO3H2, OPO—(O—(C1-C2)alkyl)2, OSO3H, SO3H, O—(C1 to C6)alkyl, NH2, NH—(C1-C6) alkyl, N—[(C1-C6)alkyl]2, NH—(C3-C6)cycloalkyl, N—[(C3-C6)cycloalkyl]2, a propargyl group, CH2CN, (CH2)pOH, p varying from 1 to 6, CH2OPO3H2, CH2OPO—(O—(C1-C2)alkyl)2, CH2CH2F, CH2CHF2, CH2CF3,
• 7) R4 and R5 represent independently of each other:
• H, OH, OPO3H2, OPO—(O—(C1-C2)alkyl)2, the alkyl being optionally substituted by one or more fluorines, an O—(C1-C6)alkyl, in particular OCH3, the alkyl being optionally substituted by one or more fluorines, a C1-C6 alkyl, the alkyl being optionally substituted by one or more fluorines, a C3-C6 cycloalkyl, a halogen,
• R4 and R5 represent together a (C1-C2) alkenyl dioxy optionally substituted by one or more fluorines, and the pharmaceutically acceptable salts.