Mannose derivatives for treating bacterial infections

A compound of Formula I

• or a pharmaceutically acceptable salt thereof, wherein
• each M and M2 is independently
• or M together with Ring A form a spiro-fused tricyclic ring as shown below:
• or M2 together with Ring A2 form a spiro-fused tricyclic ring as shown below:
• wherein:
• Y1 is —O—, —O(C1-C4 aliphatic)-, —O(haloC1-C4 aliphatic)-, —S—, —S(C1-C4 aliphatic)-, —S(O)p—, —S(O)p(C1-C4 aliphatic)-, or —(C1-C6)aliphatic;
• Y2 is —O(C1-C4 aliphatic)-, —O(haloC1-C4 aliphatic)-, —S(C1-C4 aliphatic)-, —SO2(C1-C4 aliphatic)-, or —(C1-C6) aliphatic;
• Y3 is —O—, —O(C1-C4 aliphatic)-, —O(haloC1-C4 aliphatic)-, —S—, —S(C1-C4 aliphatic)-, —S(O)p—, —S(O)p(C1-C4 aliphatic)-, or —(C1-C6)aliphatic;
• each Z2, Z3, Z4, and Z6 is independently OH or F;
• provided that at least one of Z2, Z3, Z4, and Z6 is F;
• X1 is —U1—V1;
• X1 is optionally substituted with 1-4 occurrences of halo;
• U1 is —(CH2)q— or —C(O)—;
• V1 is a C1-C10 aliphatic wherein up to four methylene units can be optionally replaced with —O—, —NR2—, —S—, —C(O)—, —S(O)—, —S(O)2—, or P(O);
• X2 is H, C1-C10 aliphatic, —U2—V2, or —U2—V2-Q;
• U2 is —(CH2)q— or —C(O)—;
• V2 is a C1-C10 aliphatic wherein up to four methylene units can be optionally replaced with —O—, —NR2—, —S—, —C(O)—, —S(O)—, —S(O)2—, or P(O);
• Q is a 3-8 membered saturated, partially unsaturated, or aromatic ring having 0-4 heteroatoms selected from oxygen, nitrogen, or sulfur;
• wherein X2 is optionally substituted with 1-4 occurrences of halo, CN, NO2, or C1-C10aliphatic wherein up to three methylene units of the C1-C10aliphatic can be optionally replaced with —NR—, —O—, —S—, —C(O)—, or —S(O)—, or —S(O)2—;
• each X3, X4, X5, and X6 is independently H or C1-3alkyl;
• provided that only one of X2, X3, X4, X5, and X6 is not H;
• Ring A is C3-C10 cycloalkyl, 3-12 membered heterocyclyl, C6-10 aryl, or 5-14 membered heteroaryl;
• wherein the heterocyclyl or heteroaryl independently has 1-6 heteroatoms selected from oxygen, nitrogen, or sulfur;
• Ring A2 is optionally absent, C3-C10 cycloalkyl, 3-12 membered heterocyclyl, C6-10 aryl, or 5-14 membered heteroaryl;
• Z is —CH═CH—, —C≡C—, or Ring B;
• Ring B is C3-C10 cycloalkyl, 3-12 membered heterocyclyl, C6-10 aryl, or 5-14 membered heteroaryl;
• wherein said heterocyclyl or heterocyclyl independently has 1-6 heteroatoms selected from oxygen, nitrogen, or sulfur;
• each JA, JA2, and JB is independently halogen, CN, NO2, oxo, C3-8 cycloalkyl, 3-8 membered heterocyclyl, C6-10 aryl, 5-10 membered heteroaryl, (C6-10 aryl)-(C1-C6alkyl)-, (5-10 membered heteroaryl)-(C1-C6alkyl)-, (C3-8 cycloalkyl)-(C1-C6alkyl)-, (3-8 membered heterocyclyl)-(C1-C6alkyl)-, or a C1-C12 aliphatic;
• wherein up to four methylene units of the C1-C12 aliphatic or up to three methylene units of the C1-C6alkyl can be optionally replaced with —NR, —O, —S—, —C(O)—, —S(O)—, —S(O)2—, or P(O);
• each JA, JA2, and JB is independently and optionally substituted with 1-5 occurrences of halo, CN, NO2, or C1-C10aliphatic wherein up to three methylene units of the C1-C10aliphatic can be optionally replaced with —NR—, —O—, —S—, —C(O)—, or —S(O)—, or —S(O)2—;
• R and R2 are each independently H, C1-C6 aliphatic, or C3-6cycloalkyl;
• each m, n, and u is independently 0, 1, 2, 3, or 4;
• each t and r is independently 0 or 1;
• and
• each p and q is independently 1 or 2.