Streptogramin derivatives, preparation method and compositions containing same

A compound of formula (IX)

• wherein
• (A)—Ra is a methyl group,
• —R5 is chosen from disubstituted methylenyl groups of formula:
• wherein:
• (a) R2 is chosen from a hydrogen atom and C1-C3 alkyl groups and
• R4 is a hydrogen atom, or
• (b) R2 is a hydrogen atom and
• R4 is chosen from a hydrogen atom and dialkylamino groups,
• —Rb, Rc, and Rd axe defined as follows:
• (1)—Rb and Rc are each a hydrogen atom, and
• —Rd is chosen from a hydrogen atom, a methylamino group, and a dimethylamino group, or
• (2)—Rb is a hydrogen atom,
• —Rc is chosen from a hydrogen atom, a chlorine atom, a bromine atom, and C3-C5 alkenyl groups, and
• —Rd is chosen from —N(CH3)R′″ groups, wherein
• —R′″ is chosen from
• (a) alkyl groups, C2-C4 hydroyalkyl groups, and C2-C8 alkenyl groups, wherein said C2-C8 alkenyl groups are optionally substituted with a group chosen from
• (i) an unsubstituied phenyl group, C3-C6 cycloalkyl groups, a methyl group, a benzyl group,
• (ii) a beuzyl group substituted with at least one substituent chosen from halogen atoms, a hydroxyl group, alkyl groups, alkyloxy groups, alkylthio groups, alkylsulphinyl groups, alkylsulphonyl groups, an amino group, aikylamino groups, and dialkylamino groups,
• (iii) heterocyclylmethygroups and heterocyclylethyl groups, wherein said heterocyclyl portions of said heterocyclylmethyl groups and said heterocyclylethyl groups are chosen from saturated and unsaturated 5- to 6-membered heterocyclyl groups comprising from 1 to 2 heteroatoms chosen from a sulphur atom, an oxygen atom, and a nitrogen atom, and wherein said heterocyclyl groups are optionally substituted with a group chosen from alkyl groups, C2-C8 alkenyl groups, C3-C6 cycloalkyl groups, saturated and unsaturated 4- to 6-membered heterocyclyl groups, an unsubstituted phenyl group, a substituted phenyl group as defined above in (a)(ii),
• (b) a cyanomethyl group, and
• (c) —CH2CORe groups, wherein Re is chosen from
• (i) —OR'e groups, wherein R'e is chosen from a hydrogen atom, C1-C6 alkyl groups, C2-C6 alkenyl groups, a beuzyl group, and hererocyclylmethyl groups, wherein said heterocyclyl portion is chosen from 5- to 6-membared heterocyclyl groups comprising from 1 to 2 hereroatoms chosen from a sulphur atom, an oxygen atom, and a nitrogen atom,
• (ii) alkylamino groups, alkylmethylamino groups, heterocyclylamino grouops and heterocyclylmethyl amino groups, wherein said heterocyclyl portion of said heterocyclylamino groups and said heterocyelylmethylamino groups is chosen from 5- to 6-membered saturated hetarocyclyl groups comprising from 1 to 2 heteroatoms chosen from a sulphur atom, an oxygen atom, and a nitrogen atom, and wherein said heterocyclyl groups are optionally substituted with a group chosen from alkyl groups, a benzyl group, and alkyloxycarbonyl groups, or
• (3) —Rb is a hydrogen atom,
• —Rd is chosen from an —NHCH3 group and an —N(CH3)2 group, and Rc is chosen from a chlorine atom, and a bromine atom, or when Rd is an —N(CH3)2 group, Rc is chosen from C3-C5 alkenyl groups, or
• (4)—Rb and Rd are each a hydrogen atom, and
• —Rc is chosen from halogen atoms, alkylamino groups, dialkylamino groups, alkyloxy groups, a trifluoromethoxy group, thioalkyl groups, C1-C6 alkyl groups, and trihalomethyl groups, or
• (5)—Rb and Rc are each a hydrogen atom, and
• —Rd is chosen from halogen atoms, an ethylamino group, a diethylamino group, a methylethylamino group, alkyloxy groups, a trifluoromethoxy group, alkylthio groups, alkylsulphinyl groups, alkylsulphonyl groups, C1-C6 alkyl groups, a phenyl group, and trihalomethyl groups, or
• (6)—Rb is a hydrogen atom,
• —Rc is chosen from halogen atoms, alkylamino groups, dialkylamino groups, alkyloxy groups, a trifluoromethoxy group, thioalkyl groups, and C1-C3 alkyl groups, and
• —Rd is chosen from halogen atoms, an amino group, alkylamino groups, dialkylamino groups, alkyloxy groups, a trifluoromethoxy group, thioalkyl groups, C1-C4 alkyl groups, and trihalomethyl groups, or
• (7)—Re is a hydrogen atom, and
• —Rb and Rd are each a methyl group, or
• (B)—Ra is an ethyl group,
• —Rb, Rc and Rd are defined as above in (2) to (7), and
• —R5 is chosen from disubstituted methylenyl groups of fonnula:
• wherein R2 and R4 are defined as above, or
• (C)—R5 is a hydrogen atom,
• —Ra is a methyl group or an ethyl gronp, and
• —Rb, Rc, and Rd are defined as above in (2), provided that R′″ is not a methyl or an ethyl group when Rb and Rc are hydrogen atoms.