Antibacterial agents

Inventors

Brown, David Ryall • Collins, Ian • Czaplewski, Lloyd George • Haydon, David John

Assignees

TAXIS PHARMACEUTICALS Inc • Biots Scientific Management Pty Ltd

Abstract

Compounds of formula (I) have antibacterial activity: wherein R represents hydrogen or 1, 2 or 3 optional substituents; W is ═C(R1)— or ═N—; R1 is hydrogen or an optional substituent and R2 is hydrogen, methyl, or fluorine; or R1 and R2 taken together are —CH2—, —CH2CH2—, —O—, or, in either orientation, —O—CH2— or —OCH2CH2—; R3 is a radical of formula -(Alk1)m-(Z)p-(Alk2)n-Q wherein m, p and n are independently 0 or 1, provided that at least one of m, p and n is 1, Z is —O—, —S—, —S(O)—, —S(O2)—, —NH—, —N(CH3)—, —N(CH2CH3)—, —C(═O)—, —O—(C═O)—, —C(═O)—O—, or an optionally substituted divalent monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted divalent bicyclic heterocyclic radical having 5 to 10 ring atoms; Alk1 and Alk2 are optionally substituted C1-C6 alkylene, C2-C6 alkenylene, or C2-C6 alkynylene radicals, which may optionally terminate with or be interrupted by —O—, —S—, —S(O)—, —S(O2)—, —NH—, —N(CH3)—, or —N(CH2CH3)—; and Q is hydrogen, halogen, nitrile, or hydroxyl or an optionally substituted monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted bicyclic heterocyclic radical having 5 to 10 ring atoms.

Core Innovation

The document describes a broad compound set within the formula I benzenecarboxamide scaffold, including fluorinated benzenecarboxamides, aminocarbonyl phenoxyacetic acid and ester derivatives, and related benzenecarboxamide compounds prepared as products containing oxazole, thiazole, benzothiazole, [1,2,4]oxadiazole, quinoline, benzofuran, and benzothiophene heterocycles. The derivatives include aryl hydroxyl or alkoxy substitution patterns, difluoro positional isomers, long-chain or unsaturated alkoxy variants, and ether-linked architectures in which the heterocycle is connected through a methoxy or methylene linker to the benzamide or benzenecarboxamide core.

Named examples include 2-chloro-6-fluoro-3-hydroxybenzenecarboxamide, 2-chloro-6-fluoro-3-(hexyloxy)benzenecarboxamide, 2-chloro-6-fluoro-3-(nonyloxy)benzenecarboxamide, 2,4,6-trifluoro-3-methoxybenzenecarboxamide, 2,4-difluoro-3-(hexyloxy)benzenecarboxamide, 2,6-difluoro-3-[(E)-2-nonenyloxy]benzenecarboxamide, 2-[3-(aminocarbonyl)-2,4-difluorophenoxy]acetic acid, and Hexyl 2-[3-(aminocarbonyl)-2,4-difluorophenoxy]acetate. Additional named examples include 2,6-Difluoro-3-[2-(4-fluoro-phenyl)-thiazol-4-ylmethoxy]-benzamide, 3-[4-(4-Chloro-phenyl)-oxazol-2-ylmethoxy]-2,6-difluoro-benzamide, 3-[(5-bromo-1,3-benzothiazol-2-yl)methoxy]-2,6-difluorobenzenecarboxamide, and 2,6-difluoro-3-[(5-phenyl-1,2,4-oxadiazol-5-yl)methoxy]benzenecarboxamide.

The document provides chemical structures and synthetic or characterization data for multiple members of these series, including reported yields, melting points, HPLC-MS information such as m/z, [M+H]+ or [M-H]+, and retention times, together with some 1H NMR reporting. It references preparation from starting hydroxy, methoxy, or phenoxy carboxamides via described schemes and methods, and includes example ranges and scheme references across the substituted fluorinated benzenecarboxamide, phenoxyacetate, and related aromatic amide families.

Claims Coverage

The provided material repeatedly identifies one independent claim covering a compound defined as formula I or a salt thereof. The claim coverage is limited to that formula-level chemical scope, and no additional dependent claim features are provided in the input items.

Across the provided items, the claim coverage remains limited to a compound defined by formula I and salts thereof, with no further inventive feature refinements visible in the supplied claim text.

Stated Advantages

Documented Applications