Heterocyclic compounds and their use in preventing or treating bacterial infections

A compound of formula (I)

• wherein:
• W, unsubstituted or substituted by one or more T, is a non-aromatic, unsaturated 5- or 6-member heterocycle comprising at least one N—R2 group and a (X)n group;
• X, identical or different, is independently selected from the group consisting of represents C(O), O, N, N(R2), S, S(O), and S(O)2;
• 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, H, —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 one of the following:
• R2, identical or different, is independently selected from the group consisting of (CH2)qOQ5, —C(O)(CH2)vOQ5, —(C(O))w(CH2)v—CN, —(CH2)qOC(O)Q5, —C(O)—(CH2)vOC(O)Q5, —(C(O))w(CH2)v—C(O)OQ5, —(CH2)q—OC(O)OQ5, —C(O)(CH2)v—OC(O)OQ5, —(CH2)q—OC(O)NQ5Q6, —C(O)(CH2)v—OC(O)NQ5Q6, —(C(O))w(CH2)v—C(O)NQ5Q6, —(C(O))w(CH2)v—C(O)ONQ5, —(C(O))w(CH2)v—C(O)NHOQ5, —(C(O))w(CH2)v—C(O)NH—NHQ5, —(C(O))w(CH2)v—C(O)O—NHQ5, —(CH2)q—NHC(O)Q5, —C(O)(CH2)v—NHC(O)Q5, —(CH2)qNHS(O)2Q5, —C(O)(CH2)vNHS(O)2Q5, —(CH2)qNHS(O)2NQ5Q6, —C(O)(CH2)vNHS(O)2NQ5Q6, (CH2)q—NHC(O)OQ5, —C(O)(CH2)v—NHC(O)OQ5, —(CH2)q—NHC(O)NQ5Q6, —C(O)(CH2)v—NHC(O)NQ5Q6, —(CH2)qNQ5Q6, —C(O)(CH2)vNQ5Q6, —(CH2)q—NH—C(NHQ3)═NQ4, —C(O)(CH2)v—NH—C(NHQ3)═NQ4, (CH2)q—NH—CH═NQ3, —C(O)(CH2)v—NH—CH═NQ3, —(C(O))w(CH2)v—C(NHQ3)═NQ4, —C(O)NQ5Q6, and —C(NHQ3)═NQ4;
• or
• R2, identical or different, is independently selected from the group consisting of (C(O))w—C1-C3-alkyl that is optionally substituted by one or more T2, (C(O))w—C1-C3-fluoroalkyl that is optionally substituted by one or more T2, (C(O))w(CH2)p—C3-C6-cycloalkyl that is optionally substituted by one or more T2, —(C(O))w—(CH2)p—C3-C6-cyclofluoroalkyl that is optionally substituted by one or more T2, and —(C(O))w—(CH2)p-(4- or 5- or 6-member aromatic or saturated or totally unsaturated or partially unsaturated heterocycle) that is optionally substituted by one or more T2;
• R3 is selected from the group consisting of SO3H, CFHCO2H, and 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)qNHQ3, —(CH2)q—NH—C(NHQ3)═NQ4, (CH2)q—NH—CH═NQ3, (CH2)v—C(NHQ3)═NQ4, —(CH2)qOQ3, and —(CH2)vCONHQ3;
• or
• Q1 and Q2, identical or different, are independently elected from the group consisting of a C1-C3 alkyl optionally substituted by one or more T2 and —(CH2)p-(4- or 5- or 6-member heterocycle) optionally substituted by one or more T2;
• or
• Q1 and Q2 and the nitrogen atom to which they are bonded, form a saturated or partially unsaturated 4- or 5- or 6-member heterocycle comprising 1 or 2 or 3 or 4 heteroatoms;
• Q3 and Q4, identical or different, are independently selected from the group consisting of H and a C1-C3 alkyl;
• Q5 and Q6 are one of the following:
• Q5 and Q6, identical or different, are independently selected from the group consisting of H, —(CH2)qNHQ3, —(CH2)q—NH—C(NHQ3)═NQ4, (CH2)q—NH—CH═NQ3, (CH2)v —C(NHQ3)═NQ4, —(CH2)qOQ3;
• and —(CH2)vCONHQ3;
• or
• Q5 and Q6, identical or different, are independently selected from the group consisting of a C1-C4 alkyl optionally substituted by one or more T2 and —(CH2)p-(4- or 5- or 6-member heterocycle) optionally substituted by one or more T2;
• or
• Q5 and Q6 and the nitrogen atom to which they are bonded form a saturated or partially unsaturated 4- or 5- or 6-member heterocycle comprising 1 or 2 or 3 or 4 heteroatoms;
• T1 is one of the following:
• T1, identical or different, is independently selected from the group consisting of F, —(CH2)pOQ1, —(CH2)p—CN, —(CH2)pOC(O)Q1, —(CH2)p—C(O)OQ1, —(CH2)p—OC(O)OQ1, (CH2)p—OC(O)NHQ1, —(CH2)p—C(O)NHQ1, —(CH2)p—C(O)NHOQ1, —CH2)p—C(O)NH—NHQ1, —(CH2)p—C(O)O—NHQ1, —(CH2)p—NHC(O)Q1, —(CH2)pNHS(O)2Q1, —(CH2)pNHS(O)2NQ1Q2, —(CH2)p—NHC(O)OQ1, —(CH2)p—NHC(O)NQ1Q2, —(CH2)pNHQ1, —(CH2)p—NH—C(NHQ3)═NQ4, —(CH2)pNH—CH═NQ3, and (CH2)p—C(NHQ3)═NQ4;
• or
• T1, identical or different, is independently selected from the group consisting of C1-C3 alkyl optionally substituted by one or more T2, C1-C3 fluoroalkyl optionally substituted by one or more T2, O—C1-C3-fluoroalkyl optionally substituted by one or more T2, and —(CH2)p-(4- or 5- or 6-member heterocycle comprising at least one nitrogen atom that is aromatic or saturated or totally unsaturated or partially unsaturated) optionally substituted by one or more T2;
• T2, identical or different, is independently selected from the group consisting of OH, NH2, and CONH2;
• T, identical or different, is independently selected from the group consisting of F, C1-C3 alkyl, C1-C3 fluoroalkyl, O—C1-C3 fluoroalkyl, -(L)w-(CH2)p—C3-C6 cycloalkyl;
• -(L)w-(CH2)p—C3-C6 cyclofluoroalkyl, -(L)w-(CH2)p-heterocycle, -(L)w-(CH2)p—CN, -(L)w-(CH2)pOC(O)Q5, -(L)w-(CH2)p—C(O)OQ5, -(L)w-(CH2)pOC(O)OQ5, -(L)w-(CH2)p—OC(O)NQ5Q6, -(L)w-(CH2)p—C(O)NQ5Q6, -(L)w-(CH2)p—C(O)NQ5OQ6, -(L)w-(CH2)p—C(O)NQ5—NQ5Q6, -(L)w-(CH2)p—NQ5C(O)Q6, -(L)w-(CH2)pNQ5Q(O)2Q6, -(L)w-(CH2)p—NQ5C(O)OQ6, -(L)w-(CH2)p—NQ5C(O)NQ5Q6, -(L)w-(CH2)pNQ5Q6, -(L)w-(CH2)p—NH—C(NHQ3)═NQ4, -(L)w-(CH2)p—NH—CH═NQ3, and -(L)w(CH2)p—C(NHQ3)═NQ4;
• L, identical or different, is independently selected from the group consisting of O, S, N(R2), S(O), and S(O)2;
• m is 1 or 2;
• n is 0, 1, or 2;
• p, identical or different, is independently selected from the group consisting of 0, 1, 2, and 3;
• q, identical or different, is independently selected from the group consisting of 2 and 3;
• v, identical or different, is independently selected from the group consisting of 1, 2, and 3;
• w, identical or different, is independently selected from the group consisting of 0 and 1;
• 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 a heterocycle can be oxidized to form a S═O group or a S(O)2 group;
• and
• wherein any nitrogen atom present within a heterocycle or a tertiary amino group can be further quaternized by a methyl group;
• or
• a pharmaceutically acceptable salt, a zwitterion, a racemate, a diastereoisomer, an enantiomer, a geometric isomer, or a tautomer of formula (I).