Substituted thiophenecarboxamides and analogues as antibacterials agents

A compound of formula (Via):

• wherein
• R1 and R2 are identical and are a chlorine atom or a bromine atom;
• R4 is selected from the group consisting of hydrogen atom, C1-C6-alkyl, aralkyl, aralkyl substituted by hydroxyl, C1-C6-alkyl substituted by a C1-C6-alkylsulfanyl and R5 is a hydrogen atom;
• or
• R4 and R5 form, together with the carbon atom to which they are linked, a cyclopropyl;
• R6 is selected from the group consisting of hydrogen atom, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, aryl, aralkyl, 4-, 5- or 6-membered heterocyclyl, —C1-C6-alkyl-Si(C1-C6-alkyl)3 and —C1-C6-alkyl-C3-C8-cycloalkyl;
• U2a is a bromine atom, an iodine atom, a mesylate group, a tosylate group or a triflate group,
• wherein R4 is selected from the group consisting of hydrogen atom, C1-C6-alkyl, aralkyl, aralkyl substituted by hydroxyl, C1-C6-alkyl substituted by a C1-C6-alkylsulfanyl and R5 is a hydrogen atom when R6 is hydrogen atom or C1-C6-alkyl;
• and
• provided that when R1 and R2 are bromine atoms, U2a is not a bromine atom.

A compound of formula (Villa):

• wherein
• R1 and R2 are identical and are a chlorine atom or a bromine atom;
• U1a is an hydroxy group or a C1-C6-alkoxy group;
• and
• U2a is a mesylate group, a tosylate group or a triflate group.

A compound of formula (IXa) or (IXb):

• wherein
• R3 is methyl;
• R4 is selected from the group consisting of hydrogen atom, C1-C6-alkyl, aralkyl, aralkyl substituted by hydroxyl, C1-C6-alkyl substituted by a C1-C6-alkylsulfanyl and R5 is a hydrogen atom;
• or
• R4 and R5 form, together with the carbon atom to which they are linked, a cyclopropyl;
• R6 is selected from the group consisting of hydrogen atom, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, aryl, aralkyl, 4-, 5- or 6-membered heterocyclyl, —C1-C6-alkyl-Si(C1-C6-alkyl)3 and —C1-C6-alkyl-C3-C8-cycloalkyl;
• U4a is a chlorine atom or a bromine atom;
• and
• U5 is a chlorine atom or a bromine atom.

A compound of formula (Xa) or (Xb):

• R1 or R2 is a chlorine atom or a bromine atom;
• R3 is methyl;
• R4 is selected from the group consisting of hydrogen atom, C1-C6-alkyl, aralkyl, aralkyl substituted by hydroxyl, C1-C6-alkyl substituted by a C1-C6-alkylsulfanyl and R5 is a hydrogen atom;
• or
• R4 and R5 form, together with the carbon atom to which they are linked, a cyclopropyl;
• R6 is selected from the group consisting of hydrogen atom, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, aryl, aralkyl, 4-, 5- or 6-membered heterocyclyl, —C1-C6-alkyl-Si(C1-C6-alkyl)3 and —C1-C6-alkyl-C3-C8-cycloalkyl;
• wherein R4 is selected from the group consisting of hydrogen atom, C1-C6-alkyl, aralkyl, aralkyl substituted by hydroxyl, C1-C6-alkyl substituted by a C1-C6-alkylsulfanyl and R5 is a hydrogen atom when R6 is hydrogen atom or C1-C6-alkyl.