Heterocyclic compounds and their use in preventing or treating bacterial infections

A compound of formula (I)

• wherein:
• A-B represents:
• a CH═CH double bond, wherein A is one of the carbon atoms of the CH═CH double bond and B is the other carbon atom of the CH═CH double bond;
• or
• a ring W, unsubstituted or substituted by one or more T and having carbon atoms at the positions corresponding to the positions of A and B, which represents one of the following:
• a phenyl group;
• a 5-membered aromatic heterocycle comprising one, two, or three heteroatom(s) independently selected from the group consisting of O, N, N(R3), S, S(O) or S(O)2;
• or a 6-membered aromatic heterocycle comprising 1, 2, of 3 nitrogen heteroatom(s);
• R1 represents oxazole, isoxazole, thiazole, isothiazole, pyrazole, imidazole, imidazoline, oxadiazole, thiadiazole, triazole, tetrazole, unsubstituted or substituted by one or more T1;
• R2 represents SO3H, CFHCO2H or CF2CO2H;
• R3 independently represents hydrogen;
• —(CH2)m—CN;
• —(CH2)nOC(O)Q1;
• —(CH2)m—C(O)OQ1;
• —(CH2)n—OC(O)OQ1;
• —(CH2)n—OC(O)NQ1Q2;
• —(CH2)m—C(O)NQ1Q2;
• —(CH2)m—C(O)NQ1OQ2;
• —(CH2)m—C(O)NQ1-NQ1Q2;
• —(CH2)n—NQ1C(O)Q2;
• —(CH2)n—NQ1C(O)OQ2;
• —(CH2)n—NQ1C(O)NQ1Q2;
• —(CH2)nOQ1;
• —(CH2)nNQ1Q2;
• —(CH2)n—NH—C(NHQ3)=NQ4;
• —(CH2)n—NH—CH═NQ3;
• —(CH2)m—C(NHQ3)=NQ4;
• —(Y)—C1-C6-alkyl;
• —(Y)—C1-C6-fluoroalkyl;
• —(Y)—C3-C6-cycloalkyl;
• —(Y)—C3-C6-cyclofluoroalkyl;
• —(Y)—(CH2)p—CN;
• —(Y)—(CH2)pOC(O)Q1;
• —(Y)—(CH2)p—C(O)OQ1;
• —(Y)—(CH2)p—OC(O)OQ1;
• —(Y)—(CH2)p—OC(O)NQ1Q2;
• —(Y)—(CH2)p—C(O)NQ1Q2;
• —(Y)—(CH2)p—C(O)NQ1OQ2;
• —(Y)—(CH2)p—C(O)NQ1-NQ1Q2;
• —(Y)—(CH2)p—NQ1C(O)Q2;
• —(Y)—(CH2)p—NQ1C(O)OQ2;
• —(Y)—(CH2)p—NQ1C(O)NQ1Q2;
• —(CH2)nOQ1;
• —(Y)—(CH2)pNQ1Q2;
• —(Y)—(CH2)p—NH—C(NHQ3)=NQ4;
• —(Y)—(CH2)p—NH—CH═NQ3;
• —(Y)—(CH2)p—C(NHQ3)=NQ4;
• or
• R3, unsubstituted or substituted by one or more T2, independently represents-C1-C6-alkyl;
• —C1-C6-fluoroalkyl;
• —C3-C6-cycloalkyl;
• —C3-C6-cyclofluoroalkyl;
• —(CH2)m-(aromatic, totally or partially unsaturated, 4- to 6-membered heterocycle comprising at least one nitrogen heteroatom) or —(Y)—(CH2)m-(aromatic, totally or partially unsaturated, 4- to 6-membered heterocycle comprising at least one nitrogen heteroatom);
• T and T1, identical or different, independently represent a fluorine atom;
• O—C1-C6-fluoroalkyl;
• —(CH2)m—C3-C6-cyclofluoroalkyl;
• —(CH2)m—CN;
• —(CH2)mOC(O)Q1;
• —(CH2)m—C(O)OQ1;
• —(CH2)m—OC(O)OQ1;
• —(CH2)m—OC(O)NQ1Q2;
• —(CH2)m—C(O)NQ1Q2;
• —(CH2)m—C(O)NQ1OQ2;
• —(CH2)m—C(O)NQ1-NQ1Q2;
• —(CH2)m—NQ1C(O)Q2;
• —(CH2)m—NQ1C(O)OQ2;
• —(CH2)m—NQ1C(O)NQ1Q2;
• —(CH2)mOQ1;
• —(CH2)mNQ1Q2;
• —(CH2)m—NH—C(NHQ3)═NQ4;
• —(CH2)m—NH—CH═NQ3;
• —(CH2)m—C(NHQ3)═NQ4;
• -(L)-(CH2)p—CN;
• -(L)-(CH2)nOC(O)Q1;
• -(L)-(CH2)p—C(O)OQ1;
• -(L)-(CH2)n—OC(O)OQ1;
• -(L)-(CH2)n—OC(O)NQ1Q2;
• -(L)-(CH2)p—C(O)NQ1Q2;
• -(L)-(CH2)p—C(O)NQ1OQ2;
• -(L)-(CH2)p—C(O)NQ1-NQ1Q2;
• -(L)-(CH2)n—NQ1C(O)Q2;
• -(L)-(CH2)n—NQ1C(O)OQ2;
• -(L)-(CH2)n—NQ1C(O)NQ1Q2;
• -(L)-(CH2)nOQ1;
• -(L)-(CH2)nNQ1Q2;
• -(L)-(CH2)n—NH—C(NHQ3)═NQ4;
• -(L)-(CH2)n—NH—CH═NQ3;
• -(L)-(CH2)n—C(NHQ3)═NQ4;
• or
• T and T1, identical or different, unsubstituted or substituted by one or more T3, independently represent C1-C6-alkyl;
• C1-C6-fluoroalkyl;
• —(CH2)m—C3-C6-cycloalkyl;
• -(L)-C1-C6-alkyl;
• -(L)-C1-C6-fluoroalkyl;
• -(L)-C3-C6-cycloalkyl;
• -(L)-C3-C6-cyclofluoroalkyl;
• —(CH2)m-(aromatic, totally or partially unsaturated, 4- to 6-membered heterocycle comprising one, two, or three nitrogen heteroatoms(s);
• -(L)-(CH2)p-(aromatic, totally or partially unsaturated, 4- to 6-membered heterocycle comprising one, two, or three nitrogen heteroatoms(s);
• Q1 and Q2, identical or different, independently represent a hydrogen atom;
• —(CH2)nNHQ3;
• —(CH2)n—NH—C(NHQ3)═NQ4;
• (CH2)n—NH—CH═NQ3;
• (CH2)p—C(NHQ3)═NQ4;
• —(CH2)nOQ3;
• —(CH2)pCONHQ3;
• —(CH2)n—NHCONHQ3 or Q1 and Q2, identical or different, unsubstituted or substituted by one or more T3, independently represent a C1-C3-alkyl;
• —(CH2)m-(aromatic, totally or partially unsaturated, 4-, 5- or 6-membered heterocycle comprising one, two, or three nitrogen heteroatoms(s);
• or
• Q1, Q2 and the nitrogen atom to which they are bonded, form an unsubstituted or substituted by one or more T3, aromatic, saturated or partially unsaturated, 4-, 5- or 6-membered heterocycle comprising one nitrogen heteroatom and optionally comprising 1, 2, or 3 further nitrogen heteroatoms;
• Q3 and Q4, identical or different, independently represent a hydrogen atom or a C1-C3-alkyl;
• T2 and T3, identical or different, independently represent a fluorine atom;
• C1-C6-alkyl;
• C1-C6-fluoroalkyl;
• O—C1-C6-fluoroalkyl;
• —(CH2)m—C3-C6-cycloalkyl;
• —(CH2)m—C3-C6-cyclofluoroalkyl;
• —(CH2)m—CN;
• —(CH2)mOC(O)Q3;
• —(CH2)m—C(O)OQ3;
• —(CH2)m—OC(O)OQ3;
• —(CH2)m—OC(O)NQ3Q4;
• —(CH2)m—C(O)NQ3Q4;
• —(CH2)m—C(O)NQ3OQ4;
• —(CH2)m—C(O)NQ3-NQ3Q4;
• —(CH2)m—NQ3C(O)Q4;
• —(CH2)m—NQ3C(O)OQ4;
• —(CH2)m—NQ3C(O)NQ3Q4;
• —(CH2)mOQ1;
• —(CH2)mNQ3Q4;
• —(CH2)m—NH—C(NHQ3)═NQ4;
• —(CH2)m—NH—CH═NQ3;
• —(CH2)m—C(NHQ3)═NQ4;
• -(L)-(CH2)p—C3-C6-cycloalkyl;
• -(L)-(CH2)p—C3-C6-cyclofluoroalkyl;
• -(L)-(CH2)p—CN;
• -(L)-(CH2)nOC(O)Q3;
• -(L)-(CH2)p—C(O)OQ3;
• -(L)-(CH2)n—OC(O)OQ3;
• -(L)-(CH2)n—OC(O)NQ3Q4;
• -(L)-(CH2)p—C(O)NQ3Q4;
• -(L)-(CH2)p—C(O)NQ3OQ4;
• -(L)-(CH2)p—C(O)NQ3-NQ3Q4;
• -(L)-(CH2)n—NQ3C(O)Q4;
• -(L)-(CH2)n—NQ3C(O)OQ4;
• -(L)-(CH2)n—NQ3C(O)NQ3Q4;
• -(L)-(CH2)nOQ1;
• -(L)-(CH2)nNQ3Q4;
• -(L)-(CH2)n—NH—C(NHQ3)═NQ4;
• -(L)-(CH2)n—NH—CH═NQ3;
• -(L)-(CH2)n—C(NHQ3)═NQ4;
• Y, identical or different, independently represents C═O or S(O)2;
• L, identical or different, independently represents O, S, N(R3), S(O) or S(O)2;
• m independently represents 0, 1, 2, 3 or 4;
• n independently represents 2, 3 or 4;
• p independently represents 1, 2, 3 or 4 when Y is C═O or 2, 3 or 4 when Y is S(O)2;
• wherein:
• any carbon atom present within a group selected from alkyl, cycloalkyl, fluoroalkyl, cyclofluoroalkyl and heterocycle can be oxidized to form a C═O group;
• any sulphur atom present within a heterocycle can be oxidized to form a S═O group or a S(O)2 group;
• and
• any nitrogen atom present within a heterocycle or present within a group that is trisubstituted thus forming a tertiary amino group can be further quaternized by a methyl group such that the quaternized amino group in conjunction with a counter ion maintains the pharmaceutical acceptability of the pharmaceutical compound;
• or a pharmaceutically acceptable salt, a zwitterion, an optical isomer, a racemate, a diastereoisomer, an enantiomer, a geometric isomer or a tautomer thereof.