Heterocyclic compounds and their use in preventing or treating bacterial infections

A compound of formula

• wherein:
• Y is selected from the group consisting of a halogen, —B(OR)2, and SnR3, wherein R is an alkyl or the OR are linked together with the B to form a 5-membered cycle;
• and
• PG, is a protective group selected from the group consisting allyl, benzyl, tertbutyldimethylsilyl (TBDMS), and tert-butoxycarbonyl (Boc).

A compound of formula

• wherein:
• R1 represents a 5-membered heterocycle, optionally substituted by one or more T1, that is saturated, partially unsaturated, or aromatic and that comprises a nitrogen atom, wherein said 5-membered heterocycle is linked to the structure by said nitrogen atom, and wherein said nitrogen atom may be quaternized;
• □T1, identical or different, independently represents a fluorine atom;
• ═O;
• —C(O)Q1;
• —(CH2)m—S(O)2-NQ1Q2;
• —(CH2)m—C(═NOQ1)Q3;
• —(X)—(CH2)p—S(O)2NQ1Q2;
• —C(O)—(CH2)n—S(O)2NQ1Q2;
• —(CH2)m—O—(CH2)p—O—(CH2)p—NQ1Q2;
• —(CH2)mOQ1;
• —(CH2)m—CN;
• —(CH2)m—OC(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)ONQ1Q2;
• —(CH2)m—C(O)NQ1Q2;
• —(CH2)m—C(O)NQ1-NQ1Q2;
• —(CH2)m—NQ1C(O)Q2;
• —(CH2)m—NQ1S(O)2NQ1Q2;
• —(CH2)m—NQ1S(O)2Q2;
• —(CH2)m-NQ1C(O)OQ2;
• —(CH2)mNQ1C(O)NQ1Q2;
• —(CH2)mNQ1Q2;
• —(CH2)m—NH—C(NHQ3)=NQ4;
• —(CH2)mNH—CH═NQ3;
• —(CH2)m—C(NHQ3)=NQ4;
• —(X)—(CH2)pOQ1;
• —(X)—(CH2)n—CN;
• —(X)—(CH2)p—OC(O)Q1;
• —(X)—(CH2)n—C(O)OQ1;
• —(X)—(CH2)p—OC(O)OQ1;
• —(X)—(CH2)p—OC(O)NQ1Q2;
• —(X)—(CH2)n—C(O)NQ1Q2;
• —(X)—(CH2)n—C(O)ONQ1Q2;
• —(X)—(CH2)n—C(O)NQ1OQ2;
• —(X)—(CH2)n—C(O)NQ1NQ2;
• —(X)—(CH2)p-NQ1C(O)Q2;
• —(X)—(CH2)p—NQ1S(O)2NQ1Q2;
• —(X)—(CH2)p—NQ1S(O)2Q2;
• —(X)—(CH2)p—NQ1C(O)OQ2;
• —(X)—(CH2)p—NQ1C(O)NQ1Q2;
• —(X)—(CH2)p—NQ1Q2;
• —(X)—(CH2)p—NH—C(NHQ3)=NQ4;
• —(X)—(CH2)p—NH—CH═NQ3;
• —(X)—(CH2)n—C(NHQ3)=NQ4;
• —C(O)—(CH2)nOQ1;
• —C(O)—(CH2)n—CN;
• —C(O)—(CH2)n—OC(O)Q1;
• —C(O)—(CH2)n—C(O)OQ1;
• —C(O)—(CH2)n—OC(O)OQ1;
• —C(O)—(CH2)n—OC(O)NQ1Q2;
• —C(O)—(CH2)n—C(O)NQ1Q2;
• —C(O)—(CH2)n—C(O)ONQ1Q2;
• —C(O)—(CH2)n—C(O)NQ1OQ2;
• —C(O)—(CH2)n—C(O)NQ1-NQ1Q2;
• —C(O)—(CH2)n—NQ1C(O)Q2;
• —C(O)—(CH2)n—NQ1S(O)2NQ1Q2;
• —C(O)—(CH2)n—NQ1S(O)2Q2;
• —C(O)—(CH2)n—NQ1C(O)OQ2;
• —C(O)—(CH2)n—NQ1C(O)NQ1Q2;
• —C(O)—(CH2)n—NQ1Q2;
• —C(O)—(CH2)n—NH—C(NHQ3)=NQ4;
• —C(O)—(CH2)n—NH—CH═NQ3;
• or —C(O)—(CH2)n—C(NHQ3)=NQ4;
• or
• □T1, identical or different, independently represents an unsubstituted or substituted by one or more T2, —(CH2)m-(4-, 5- or 6-membered saturated, partially or totally unsaturated, or aromatic heterocycle);
• —(X)—(CH2)m-(4-, 5- or 6-membered saturated, partially or totally unsaturated, or aromatic heterocycle);
• (C1-C3)-alkyl;
• (C1-C3)-fluoroalkyl;
• —(X)—(C1-C3)-alkyl;
• —(X)—(C1-C3)-fluoroalkyl;
• —(CH2)m—(C3-C6)-cycloalkyl;
• —(X)—(CH2)m(C3-C6)-cycloalkyl;
• —(CH2)m(C3-C6)-cyclofluoroalkyl;
• —(X)—(CH2)m(C3-C6)-cyclofluoroalkyl;
• —C(O)—(CH2)m-(4-, 5- or 6-membered saturated, partially or totally unsaturated, or aromatic heterocycle);
• —C(O)—(C1-C3)-alkyl;
• —C(O)—(C1-C3)-fluoroalkyl;
• —C(O)O—(C1-C3)-fluoroalkyl;
• —C(O)—(CH2)m(C3-C6)-cycloalkyl;
• —C(O)—(CH2)m(C3-C6)-cycloalkyl;
• —C(O)—(CH2)m(C3-C6)-cyclofluoroalkyl;
• or —C(O)—(CH2)m(C3-C6)-cyclofluoroalkyl;
• T2, identical or different, independently represents —OH;
• —NH2;
• or —CONH2;
• □Q1 and Q2, identical or different, independently represent a hydrogen atom;
• —(CH2)r—NHQ3;
• —(CH2)r—NH—C(NHQ3)=NQ4;
• —(CH2)r—NH—CH═NQ3;
• (CH2)n—C(NHQ3)=NQ4;
• —(CH2)r—OQ3;
• —(CH2)n—CONHQ3;
• an unsubstituted or substituted by one or more T2, (C1-C3)-alkyl;
• (C1-C3)-fluoroalkyl;
• or a saturated, partially or totally unsaturated, or aromatic-(CH2)m(4-, 5- or 6-membered heterocycle comprising at least one nitrogen atom);
• or
• □Q1, Q2, and the nitrogen atom to which they are bonded, form together an unsubstituted or substituted by one or more T2, saturated or partially unsaturated 4-, 5- or 6-membered heterocycle comprising 1, 2, or 3 heteroatoms;
• Q3 and Q4, identical or different, independently represent a hydrogen atom or (C1-C3)-alkyl;
• m, identical or different, independently represents 0, 1, 2 or 3;
• n, identical or different, independently represents 1, 2 or 3;
• p, identical or different, independently represents 2 or 3;
• r is 1, 2 or 3 when the (CH2), is directly linked to a carbon atom or 2 or 3 otherwise;
• and
• X, identical or different, independently represents O;
• S;
• S(O);
• S(O)2 or N(Q3);
• and
• 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 group wherein it is trisubstituted thus forming a tertiary amino group, can be further quaternized by a methyl group.