Antibacterial agents

Inventors

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

Assignees

TAXIS PHARMACEUTICALS Inc • Biota Scientific 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)—; R1 is hydrogen 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—; and R3 is a radical of formula -(Alk1)m-(Z)p-(Alk2)n-Q.

Core Innovation

The invention relates to substituted benzamide compounds of formula (I), (IA), and (IC), or salts, hydrates, or solvates thereof, for use in treating bacterial infection. The compounds are defined by specific substituent relationships, including W as C(R1), R1 as hydrogen, R2 as hydrogen, methyl, or fluorine, and a divalent radical Z linked to Q, where Q is an optionally substituted phenyl. The structural definition also includes R as hydrogen or optional substituents and R3 as a radical of formula -(Alk1)m-(Z)p-(Alk2)n-Q with m and n independently 0 and p is 1.

The divalent radical Z is selected from optionally substituted radicals in either orientation, and the meaning of optionally substituted is defined by an enumerated set of substituents, including alkyl, alkenyl, alkynyl, alkoxy, hydroxy, mercapto, halo, fully or partially fluorinated alkyl, nitro, nitrile, oxo, phenyl, phenoxy, monocyclic heteroaryl, heteroaryloxy, and carbonyl-, sulfonyl-, amino-, nitrogen-containing, and related substituent classes. For Q, the optional substitution is limited to up to four substituents from the same defined classes, and any vacant ring position or unsubstituted ring carbon is optionally substituted in the related embodiments.

The patent further includes embodiments in which R4 and R5 are independently fluoro or chloro, or one of R4 and R5 is hydrogen while the other is fluoro or chloro. In these embodiments, R3 is selected from radicals of formulae A-H, including heteroaryl and phenyl-containing options, and the disclosure also frames the compounds in pharmaceutical and antibacterial compositions with a pharmaceutically acceptable carrier and an amount effective to inhibit bacterial growth.

Claims Coverage

The content includes three independent claim groupings. Across these claims, the core coverage is defined by substituted benzamide compounds with constrained W, R1, R2, R4, R5, and R3/Z-Q substituent patterns, and one independent claim expressly recites use in treating bacterial infection.

The claims are centered on substituted benzamide scaffolds with tightly defined linkage and substituent constraints, including fixed hydrogen at R1, constrained R2 and R4/R5 selections, and R3 selected from formulae A-H within a Z-Q framework where Q is an optionally substituted phenyl. The claim set also includes bacterial infection treatment use and antibacterial composition context.

Stated Advantages

Documented Applications