Heterocyclic Compounds And Their Use in Preventing or Treating Bacterial Infections

A compound of formula (I), in which:

• wherein:
• R1 is chosen in the group consisting of H, CN, C(═O)NR2R3, C(═O)NR4NR2R3, C(═O)NR2OR3, (CH2)nOR2, (CH2)nNR2R3, (CH2)nNR4C(═NR4)N(R4)2, C(═NOZ4)NZ1Z2, (CH2)n-(5 to 6-membered)heteroaryl comprising 1 or 4 heteroatoms independently chosen in the group consisting of N, O or S;
• n is an integer comprised between 1 and 6;
• R2 and R3, identical or different, are chosen in the group consisting of H, linear or branched (C1-C6)alkyl, (C3-C11)cycloalkyl, (4 to 6-membered)heterocyclyl comprising 1 or 2 heteroatoms independently chosen in the group consisting of N, O or S, (5 to 10-membered)heteroaryl comprising from 1 to 4 heteroatom independently chosen in the group consisting of N, O or S, C(═O)(C1-C6)alkyl, C(═O)(4 to 6-membered)heterocyclyl comprising 1 or 2 heteroatoms independently chosen in the group consisting of N, O or S, or form together with the nitrogen atom to which they are linked a (4 to 6-membered)heterocyclyl comprising 1 or 2 heteroatom independently chosen in the group consisting in N, O or S, wherein the alkyl, cycloalkyl, aryl, heterocyclyl and heteroaryl are optionally substituted by one or more R5;
• R4, each identical or different, is independently chosen in the group consisting of H and linear or branched (C1-C6)alkyl optionally substituted by one or more R5;
• R5, each identical or different, is chosen in the group consisting of OH, O(C1-C6)alkyl, NH2, NH(C1-C6)alkyl, N[(C1-C6)alkyl]2, C(═O)NH2, C(═O)NH(C1-C6)Alkyl, C(═O)N[(C1-C6)Alkyl]2;
• Y1 is chosen in the group consisting of SO3H, CHFC(═O)Y2 and CF2C(═O)Y2, SO3(C1-C6)alkyl-C(═O)O(C1-C6)alkyl;
• Y2 is chosen in the group consisting of OH, O(C1-C6)alkyl linear or branched, O(C3-C11)cycloalkyl, O-(4 to 6-membered)heterocyclyl comprising 1 or 2 heteroatom independently chosen in the group consisting of N, O and S;
• NY3Y4, wherein the alkyl, cycloalkyl and heterocyclyl are optionally substituted by one or more Y5;
• Y3 and Y4, each identical or different, is chosen in the group consisting of linear or branched (C1-C6)alkyl, linear or branched O(C1-C6)alkyl, (C3-C11)cycloalkyl, (4 to 6-membered)heterocyclyl comprising 1 or 2 heteroatoms independently chosen in the group consisting of N, O or S, or form together with the nitrogen atom to which they are linked a (4 to 6-membered)heterocyclyl comprising 1 or 2 heteroatoms independently chosen in the group consisting of N, O or S;
• wherein the alkyl, cycloalkyl and heterocyclyl is optionally substituted by one or more Y5;
• Y5, each identical or different, is chosen in the group consisting of linear or branched (C1-C6)alkyl, (C3-C6)cycloalkyl, linear or branched O(C1-C6)alkyl, linear or branched O(C1-C6)alkyl-O(C1-C6)alkyl, linear or branched (C1-C6)alkyl-O(C1-C6)alkyl;
• and O(C3-C6)cycloalkyl;
• X1═X2 is chosen in the group consisting of N═CX4, CX3=CA1 and CA1=CX4;
• A1 is chosen in the group consisting of H, (CH2)m—C(═O)NA2A3, (CH2)n—NA2A3;
• A2 and A3, each identical or different is chosen in the group consisting of H, linear or branched (C1-C6)alkyl, linear or branched O—(C1-C6)alkyl;
• X3 and X4 is chosen in the group consisting of (CH2)m—C(═O)NX6X7, (CH2)m—C(═NX6)NHX7, (CH2)n—NX6X7, (CH2)n—NX6C(═O)X7, (CH2)n—NHC(═NX6)NHX7, (CH2)n—NHC(═NX6)X7, (CH2)m-(5- to 6-membered heteroaryl comprising from 1 to 4 heteroatom independently chosen in the group consisting of N, O, S), (CH2)m-(4- to 6-membered heterocyclyl comprising from 1 to 2 heteroatom independently chosen in the group consisting of N,O,S), wherein the heteroaryl is substituted at least by one or more Z3 and the heterocyclyl is optionally substituted by Z3;
• m is an integer comprised between 0 and 6;
• X6, X7 and X8, each identical or different, are chosen in the group consisting of H, linear or branched (C1-C6)alkyl-Z3, or form together with the nitrogen atom to which they are linked a 4 to 6-membered heterocyclyl comprising 1 or 2 heteroatoms independently chosen in the group consisting of N, O or S, wherein the heterocyclyl are optionally substituted by Z3;
• Z1 and Z2, each identical or different are chosen in the group consisting of H, linear or branched (C1-C6)alkyl;
• Z3, each identical or different, is chosen in the group consisting of (CH2)m—NZ1Z2, (CH2)m—NHC(═NH)Z1, (CH2)m—NHC(═NH)NHZ1;
• any sulphur atom present within a heterocycle can be oxidized to form a S═O group or a S(O)2 group;
• any nitrogen atom present within a heterocycle or present within group wherein it is trisubstituted thus forming a tertiary amino group, can be further quaternized by a methyl group;
• Z4 represents H or linear or branched (C1-C6)alkyl;
• or
• a racemate, an enantiomer, a diastereoisomer, a geometric isomer or a pharmaceutically acceptable salt thereof, with the exception that if one of X3 or X4 represent (CH2)m—C(═O)NX6X7, or (CH2)n—NX6X7 then at least one of X6 or X7 is different from H.