Heterocyclic compounds and their use in preventing or treating bacterial infections

A compound of formula (I)

• wherein:
• R1 is selected from the group consisting of a carbon-linked 4- or 5- or 6-member heterocycle comprising at least one nitrogen atom that is aromatic or saturated or totally unsaturated or partially unsaturated and optionally substituted by one or more T1, —CN, —C(O)NHQ1, —C(O)NHOQ1, —C(O)NH—NHQ1, —C(O)O—NHQ1, —C(O)OQ1, —(CH2)mOC(O)OQ1, —(CH2)mOQ1, —(CH2)mOC(O)Q1, —(CH2)mOC(O)NQ1Q2, —(CH2)m—NHC(O)Q1, —(CH2)mNHS(O)2Q1, —(CH2)mNHS(O)2NQ1Q2, —(CH2)mNHC(O)OQ1,—(CH2)mNHC(O)NQ1Q2, —(CH2)mNHQ3, —(CH2)mNH—C(NHQ3)=NQ4, —(CH2)mNH—CH═NQ3, and —C(NHQ3)=NQ4;
• R2 is O or NOQ5;
• R3 is SO3H, CFHCO2H or CF2CO2H;
• Q1 and Q2 are one of the following:
• Q1 and Q2, identical or different, are independently selected from the group consisting of H, —(CH2)pNHQ3, —(CH2)p—NH—C(NHQ3)═NQ4, (CH2)p—NH—CH=NQ3, (CH2)q—C(NHQ3)=NQ4, —(CH2)pOQ3, and —(CH2)qCONHQ3;
• or
• Q1 and Q2, identical or different, are independently selected from the group consisting of C1-C3 alkyl that is optionally substituted by one or more T2, and —(CH2)n—(4- or 5- or 6-member heterocycle) that is optionally substituted by one or more T2;
• or
• Q1 and Q2 and the nitrogen atom to which they are bonded form together a saturated or partially unsaturated 4- or 5- or 6-member heterocycle comprising 1 or 2 or 3 heteroatoms;
• Q3 and Q4, identical or different, are independently selected from the group consisting of H and C1-C3 alkyl;
• Q5 is one of the following:
• Q5 is selected from the group consisting of C1-C3 alkyl that is optionally substituted by one or more T3, C1-C3 fluoroalkyl;
• —(CH2)n—C3-C6 cycloalkyl that is optionally substituted by one or more T3;
• —(CH2)n—C3-C6 cyclofluoroalkyl that is optionally substituted by one or more T3, and —(CH2)n—(4- or 5- or 6-member heterocycle) that is optionally substituted by one or more T3;
• or
• Q5 is selected from the group consisting of H, (CH2)pOQ6, —(CH2)q—CN, —(CH2)pOC(O)Q6, —(CH2)q—C(O)OQ6, —(CH2)p—OC(O)OQ6, —(CH2)p—OC(O)NQ6Q7, —(CH2)q—C(O)NQ6Q7, —(CH2)q—C(O)NQ6OQ7, —(CH2)q—C(O)NQ6—NQ6Q7, —(CH2)p—NQ6C(O)Q7, —(CH2)pNQ6S(O)2Q7, —(CH2)pNQ6S(O)2NQ6Q7, —(CH2)p—NQ6C(O)OQ6, —(CH2)p—NQ6C(O)NQ6Q7, —(CH2)pNQ6Q7, —(CH2)p—NH—C(NHQ3)=NQ4, —(CH2)p—NH—CH═NQ3, and (CH2)qC(NHQ3)=NQ4;
• T1 is one of the following:
• T1, identical or different, is independently selected from the group consisting of F, —(CH2)nOQ1, —(CH2)n—CN, —(CH2)nOC(O)Q1, —(CH2)n—C(O)OQ1, —(CH2)n—OC(O)OQ1, —(CH2)n—OC(O)NHQ1, —(CH2)n—C(O)NHQ1, —(CH2)n—C(O)NHOQ1, —(CH2)n—C(O)NH—NHQ1, —(CH2)n—C(O)O—NHQ1, —(CH2)n—NHC(O)Q1, —(CH2)nNHS(O)2Q1, —(CH2)nNHS(O)2NQ1Q2, —(CH2)n—NHC(O)OQ1, —(CH2)n—NHC(O)NQ1Q2, —(CH2)nNHQ1, —(CH2)n—NH—C(NHQ3)=NQ4, —(CH2)n—NH—CH═NQ3, and (CH2)n—C(NHQ3)=NQ4;
• or
• T1, identical or different, is independently selected from the group consisting of C1-C3 alkyl that is optionally substituted by one or more T2, C1-C3 fluoroalkyl that is optionally substituted by one or more T2, O—C1-C3 fluoroalkyl that is optionally substituted by one or more T2, and —(CH2)n—(4- or 5- or 6-member comprising at least one nitrogen atom that is aromatic or saturated or totally unsaturated or partially unsaturated) that is optionally substituted by one or more T2;
• T2, identical or different, is independently selected from the group consisting of OH, NH2, and CONH2;
• T3, identical or different, is independently selected from the group consisting of H, F, C1-C3 alkyl, C1-C3 fluoroalkyl, O—C1-C3 fluoroalkyl, —(CH2)nOQ6, —(CH2)n—C3-C6 cycloalkyl, —(CH2)n—C3-C6 cyclofluoroalkyl, —(CH2)n-heterocycle, —(CH2)n—CN,—(CH2)nOC(O)Q6, —(CH2)n—C(O)OQ6, —(CH2)n—OC(O)OQ6, —(CH2)n—OC(O)NQ6Q7, —(CH2)n—C(O)NQ6Q7, —(CH2)n—C(O)NQ6OQ7, —(CH2)n—C(O)NQ6—NQ6Q7, —(CH2)n—C(O)O—NHQ6, —(CH2)n—NQ6C(O)Q7, —(CH2)nNQ6S(O)2Q7, —(CH2)nNQ6S(O)2NQ6Q7, —(CH2)n—NQ6C(O)OQ7, —(CH2)n—NQ6C(O)NQ6Q7, —(CH2)nNQ6Q7, —(CH2)n—NH—C(NHQ3)=NQ4, —(CH2)n—NH—CH═NQ3, and —(CH2)n—C(NHQ3)=NQ4;
• Q6 and Q7 are one of the following:
• Q6 and Q7, identical or different, are independently selected from the group consisting of H, C1-C3 alkyl, —(CH2)pNHQ3, —(CH2)p—NH—C(NHQ3)=NQ4, (CH2)p—NH—CH═NQ3, (CH2)q—C(NHQ3)=NQ4, —(CH2)pOQ3, —(CH2)qC(O)NQ3Q4, and —(CH2)n—(4- or 5- or 6-member heterocycle comprising at least one nitrogen atom that is aromatic or saturated or totally unsaturated or partially unsaturated);
• or
• Q6 and Q7 and the nitrogen atom to which they are bonded form together a saturated or partially unsaturated 4- or 5- or 6-membered heterocycle comprising 1 or 2 or 3 heteroatoms;
• m, identical or different, is independently selected from the group consisting of 1 and 2;
• n, identical or different, is independently selected from the group consisting of 0, 1, 2, and 3;
• p, identical or different, is independently selected from the group consisting 2 and 3;
• q, identical or different, is independently selected from the group consisting of 1, 2, and 3;
• wherein any carbon atom present within any of the foregoing alkyls, cycloalkyls, fluoroalkyls, cyclofluoroalkyls, and heterocycles can be oxidized to form a C═O group;
• wherein any sulphur atom present within any of the foregoing heterocycles can be oxidized to form a S═O group or a S(O)2 group;
• and
• wherein any nitrogen atom, within a heterocycle or within a tertiary amino group, can be further quaternized by a methyl group;
• or
• a racemate, an enantiomer, a diastereoisomer, a geometric isomer, or a pharmaceutically acceptable salt of formula (I).