F2 derivatives as antibacterial agents
AssigneeThe Penn State Research Foundation
InventorsKenneth Charles Keiler, John Nandwa Alumasa
Life of this patent
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Abstract
A compound or its pharmaceutically acceptable salt, as well as a pharmaceutical, composition containing that compound or salt dissolved or dispersed in a pharmaceutically acceptable carrier, and a method of using that compound or salt in an antibacterial treatment. A contemplated compound corresponds in structure to structural Formula I or a pharmaceutically acceptable salt of that compound, wherein V is O or NR9, Y is halogen, OR10, C1-C4 hydrocarbyl or NHR10, Z is NR2—X—R1 or CH2—R8, n is 1-6, X is H, S(O)2, C(O), C(O)NR7, C(NH)NR7 or C(O)O, and R1, R2, R7, R8, R9 and R10 are defined within.
Claims25
A compound corresponding in structure to structural Formula I or a pharmaceutically acceptable salt of that compound
- wherein n is 1-6;
- V is O or NR9;
- R9 is hydrido (H) or C1-C4 hydrocarbyl;
- Z is NR2—X—R1 or CH2—R8;
- X is hydrido (H), S(O)2, C(O), C(O)NR7, C(NH)NR7 or C(O)O, with the proviso that when X is H, R1 and CH2—R8 are absent;
- Y is halogen, OR10, C1-C4 hydrocarbyl or NHR10;
- R10 is hydrido or C1-C4 hydrocarbyl;
- R1 and R8 are the same or different and are an aliphatic, aromatic or heteroaromatic ring system containing one ring or two fused rings each having 5-7 atoms in the ring, said ring system containing up to three substituents other than hydrogen that themselves can be the same or different (R1a, R1b, and R1c), and wherein each of those three groups, R1a-c, is separately selected from the group consisting of C1-C6 hydrocarbyl, C1-C6 hydrocarbyloxy, C1-C6 hydrocarbyloxycarbonyl, trifluoromethyl, trifluoromethoxy, C1-C7 hydrocarboyl, hydroxy-, halogen, halogen-substituted C1-C7 hydrocarboyl, C1-C7 hydrocarbylsulfonyl, C1-C6 hydrocarbyloxysulfonyl, nitro, phenyl, benzyl, cyano, carboxyl, C1-C7 hydrocarbyl carboxylate, carboxamide or sulfonamide wherein the amido nitrogen in either group has the formula NR3R4 in which R3 and R4 are the same or different and are H, C1-C4 hydrocarbyl, or R3 and R4 together with the depicted nitrogen form a 5-7-membered ring that optionally contains 1 or 2 additional hetero atoms that independently are nitrogen, oxygen or sulfur, MAr, where M is —CH2—, —O— or —N═N— and Ar is a single-ringed aryl group, and NR5R6 wherein R5 and R6 are the same or different and are H, C1-C4 hydrocarbyl, C1-C4 acyl, C1-C4 hydrocarbylsulfonyl, or R5 and R6 together with the depicted nitrogen form a 5-7-membered ring that optionally contains 1 or 2 additional hetero atoms that independently are nitrogen, oxygen or sulfur;
- and
- R2 and R7 are the same or different and are hydrido or C1-C4 hydrocarbyl.
A compound corresponding in structure to structural Formula IIA or a pharmaceutically acceptable salt of that compound
- wherein
- X is S(O)2, C(O), C(O)NR7, C(NH)NR7 or C(O)O;
- R1 is an aliphatic, aromatic or heteroaromatic ring system containing one ring or two fused rings each having 5-7 atoms in the ring, said ring system containing up to three substituents other than hydrogen that themselves can be the same or different (R1a, R1b, and R1c), and wherein each of those three groups, R1a-c, is separately selected from the group consisting of C1-C6 hydrocarbyl, C1-C6 hydrocarbyloxy, C1-C6 hydrocarbyloxycarbonyl, trifluoromethyl, trifluoromethoxy, C1-C7 hydrocarboyl, hydroxy-, halogen, halogen-substituted C1-C7 hydrocarboyl, C1-C6 hydrocarbylsulfonyl, C1-C6 hydrocarbyloxysulfonyl, nitro, phenyl, benzyl, cyano, carboxyl, C1-C7 hydrocarbyl carboxylate, carboxamide or sulfonamide wherein the amido nitrogen in either group has the formula NR3R4 in which R3 and R4 are the same or different and are H, C1-C4 hydrocarbyl, or R3 and R4 together with the depicted nitrogen form a 5-7-membered ring that optionally contains 1 or 2 additional hetero atoms that independently are nitrogen, oxygen or sulfur, MAr, where M is —CH2—, —O— or —N═N— and Ar is a single-ringed aryl group, and NR5R6 wherein R5 and R6 are the same or different and are H, C1-C4 hydrocarbyl, C1-C4 acyl, C1-C4 hydrocarbylsulfonyl, or R5 and R6 together with the depicted nitrogen form a 5-7-membered ring that optionally contains 1 or 2 additional hetero atoms that independently are nitrogen, oxygen or sulfur;
- and
- R2 and R7 are the same or different and are hydrido or C1-C4 hydrocarbyl.
The method according to claim 17, wherein said Gram positive bacteria are M. tuberculosis.
Dependencies are inferred from the claim text.