Heterocyclic compounds and their use in preventing or treating bacterial infections

A compound of formula (I)

• wherein:
• W represents an 8- to 10-membered aromatic or partially unsaturated bicycle optionally having one or more heteroatoms chosen independently from the group consisting of O, N, N(T2), S and/or optionally substituted by one or more T1;
• R1 is chosen from the group consisting of H, (CH2)mCN, (CH2)mC(═O)NR2R3, (CH2)mC(═O)NR4NR2R3, (CH2)mC(═O)NR2OR3, (CH2)pOR2, (CH2)pNR2R3, (CH2)pNR4C(═NR4)N(R4)2, (CH2)mC(═NOZ4)NZ1Z2 and (CH2)p-(5 to 6-membered heteroaryl 1 or 4 heteroatoms independently chosen from the group consisting of N, O or S);
• m is an integer from 0 to 6;
• p is an integer from 1 to 6;
• R2 and R3, identical or different, are chosen from the group consisting of H, linear or branched (C1-C6)alkyl, (C3-C11)cycloalkyl, (C6-C10)aryl, 4- to 6-membered heterocyclyl having 1 to 2 heteroatoms chosen independently from the group consisting of N, O or S, 5- to 10-membered heteroaryl having 1 to 4 heteroatoms chosen independently from the group consisting of N, O or S, C(═O)(linear or branched C1-C6)alkyl, C(═O)(4 to 6-membered heterocyclyl having 1 to 2 heteroatoms chosen independently from 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 having 1 to 2 heteroatoms chosen independently from the group consisting of N, O or S, wherein alkyl, cycloalkyl, aryl, heterocyclyl and heteroaryl are optionally substituted by one or more R5;
• R4, each identical or different, is independently chosen from the group consisting of H and linear or branched (C1-C6)alkyl, wherein alkyl is optionally substituted by one or more R5;
• R5, each identical or different, is chosen from the group consisting of OH, O-(linear or branched-C1-C6)alkyl, NH2, NH(linear or branched C1-C6)alkyl, N[(linear or branched C1-C6)Alkyl]2, C(═O)NH2, C(═O)NH (linear or branched C1-C6)alkyl and C(═ON[linear or branched(C1-C6)alkyl]2;
• Y1 is chosen from the group consisting of SO3H, CHFC(═O)Y2, CF2C(═O)Y2, and SO3(C1-C6)alkyl-C(═O)O(C1-C6)alkyl;
• Y2 is chosen from the group consisting of OH, O(C1-C6)alkyl, linear or branched, O(C3-C11)cycloalkyl, O-(4 to 6-membered heterocyclyl having 1 or 2 heteroatoms chosen independently from the group consisting of N, O and S), and NY3Y4, wherein alkyl, cycloalkyl and heterocyclyl are optionally substituted by one or more Y5;
• Y3 and Y4, each identical or different, is chosen from 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 having 1 or 2 heteroatoms chosen independently from 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 having 1 or 2 heteroatoms chosen independently from the group consisting of N, O or S, wherein alkyl, cycloalkyl and heterocyclyl is optionally substituted by one or more Y5;
• and
• Y5, each identical or different, is chosen from 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;
• T1 is chosen from the group consisting of halogen, (CH2)m-CN, (CH2)m-OX1, (CH2)m-C(═O)NX1X2, (CH2)m-C(═O)NX1OX2, (CH2)m-C(═O)NX1NX2X3, (CH2)m-C(═NOX1)X2, (CH2)m-C(═NX1)NX2X3, (CH2)m-NX1X2, (CH2)m-NX1C(═O)X2, (CH2)m-NX1C(═O)NX2X3, (CH2)m-NX1S(═O)2NX2X3, (CH2)m-NX1S(═O)2X2, (CH2)m-NX1C(═NX2)NHX3, (CH2)m-NX1C(═NX2)X2, (CH2)m-S(═O)2NX1X2, linear or branched (C1-C6)alkyl, (C3-C6)cycloalkyl, (CH2)m-aryl, (CH2)m-(5- to 6-membered heteroaryl having from 1 to 4 heteroatoms chosen independently from the group consisting of N, O or S), and (CH2)m-(4- to 6-membered heterocyclyl having from 1 to 2 heteroatoms chosen independently from the group consisting of N, O or S), wherein alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl are optionally substituted by one or more X4;
• T2 is chosen from the group consisting of H, (CH2)n-CN, (CH2)n-OX1, (CH2)m-C(═O)X1, (CH2)m-C(═O)NX1X2, (CH2)m-C(═O)NX1OX2, (CH2)m-C(═O)NX1NX2X3, (CH2)m-C(═NOX1)X2, (CH2)m-C(═NX1)NX2X3, (CH2)n-NX1X2, (CH2)n-NX1C(═O)X2, (CH2)n-NX1C(═O)NX2X3, (CH2)n-NX1S(═O)2NX2X3, (CH2)n-NX1S(═O)2X2, (CH2)n-NX1C(═NX2)NHX3, (CH2)n-NX1C(═NX2)X2, (CH2)m-S(═O)2NX2X3, linear or branched (C1-C6)alkyl, (C3-C6)cycloalkyl, (CH2)m-aryl, (CH2)m-(5- to 6-membered heteroaryl having from 1 to 4 heteroatoms chosen independently from the group consisting of N, O or S), and (CH2)m-(4- to 6-membered heterocyclyl having 1 to 2 heteroatoms chosen independently from the group consisting of N, O or S), wherein alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl are optionally substituted by one or more X4;
• X1, X2 and X3, each identical or different, are chosen from the group consisting of H, linear or branched (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkyl-NZ1Z2, (C2-C6)alkyl-NHC(═NZ1)NHZ2, (C2-C6)alkyl-NHC(═NZ1)Z2, (C2-C6)alkyl-NZ1C(═O)Z2, (C2-C6)alkyl-OZ1, (C1-C6)alkyl-C(═NZ1)NHZ2, (C1-C6)alkyl-CONZ1Z2, (C1-C6)alkyl-COOZ1, (CH2)m-aryl, (CH2)m-(5- to 6-membered heteroaryl having from 1 to 4 heteroatoms chosen independently from the group consisting of N, O and S), and (CH2)m-(4- to 6-membered heterocyclyl having from 1 to 2 heteroatoms chosen independently from the group consisting of N, O and S), or form together with the nitrogen atom to which they are linked a 4- to 6-membered heterocyclyl having 1 or 2 heteroatoms chosen independently from the group consisting of N, O or S, wherein alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl are optionally substituted by one or more Z3;
• X4, each identical or different, is chosen from the group consisting of H, halogen, linear or branched (C1-C6)alkyl, (C3-C6)cycloalkyl, (CH2)m-NZ1Z2, (CH2)m-NHC(═NZ1)NHZ2, (CH2)m-NHC(═NZ1)H, (CH2)m-NZ1C(═O)Z2, (CH2)m-OZ1, (CH2)m-C(═NZ1)NHZ2, (CH2)m-CONZ1Z2, (CH2)m-COOZ1, (CH2)m-aryl, (CH2)m-(5- to 6-membered heteroaryl having from 1 to 4 heteroatoms chosen independently from the group consisting of N, O and S), and (CH2)m-(4- to 6-membered heterocyclyl having from 1 to 2 heteroatoms chosen independently from the group consisting of N, O and S), wherein alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl are optionally substituted by one or more Z3;
• Z1 and Z2, identical or different, are chosen from the group consisting of H, linear or branched (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkyl-N(Z4)2, (C2-C6)alkyl-NZ4C(═O)Z4, (C2-C6)alkyl-OZ4, (C1-C6)alkyl-C(═NH)NHZ4, (C1-C6)alkyl-CON(Z4)2, and (C1-C6)alkyl-COOZ4;
• Z3, each identical or different, is chosen from the group consisting of H, halogen, linear or branched (C1-C6)alkyl, (C3-C6)cycloalkyl, (CH2)m-N(Z4)2, (CH2)m-OZ4C(═O)Z4, (CH2)m-OZ4, (CH2)m-CON(Z4)2, and (CH2)m-COOZ4;
• Z4, each identical or different, is chosen from the group consisting of H, linear or branched (C1-C6)alkyl, and (C3-C6)cycloalkyl,
• n is an integer from 2 to 6;
• 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;
• or
• a racemate, an enantiomer, a diastereoisomer, or a pharmaceutically acceptable salt thereof.