Antimicrobial and antiviral sulfur containing glycerol monoester derivatives

Inventors

Reardan, Dayton T. • Brennan, Paul • Schlievert, Patrick

Assignees

Niche Biopharmaceuticals LLC

Abstract

The disclosure relates generally novel sulfur containing glycerol mono-ester derivatives and methods useful for treating gram positive, gram negative, fungal and envelope viral infections in a patient.

Core Innovation

The invention provides sulfur-containing glycerol monolaurate analogs and sulfur-containing glycerol mono-ester derivatives defined by Formula (I), wherein R1 is alkyl, R2 and R3 are hydrogen, and X is O or S, including pharmaceutically acceptable salts. The compounds are described as analogs of glycerol monolaurate (GML) and related stereoisomers, with sulfur-containing features corresponding to different stereochemical forms.

The disclosure describes conversion of dioxolane-protected methanol derivatives to thiol/thioester intermediates, followed by formation of the final thioether/thiol-lipid structures associated with the sulfur-containing glycerol monolaurate analogs. The intermediates and final structures are presented as leading to the SGML and S2GML compounds and related stereoisomers.

The disclosed derivatives are positioned as antimicrobial agents and pharmaceutical compositions with pharmaceutically acceptable carriers. The document further reports antibacterial and toxin-reduction performance versus native GML, including MIC/MBC results, reduction of TSST-1 (TSS toxin-1), and statements relating the compounds to esterase/lipase susceptibility and enhanced activity relative to GML.

Claims Coverage

The independent claim covers compounds of Formula (I) with structural constraints and a salt option. Dependent claims refine the alkyl nature of R1, specify X as O or S, and extend coverage to pharmaceutical compositions with a pharmaceutically acceptable carrier.

Overall, the claims cover sulfur-containing glycerol mono-ester derivatives defined by Formula (I) with R1 as an alkyl group, R2 and R3 as hydrogen, and X as O or S, including pharmaceutically acceptable salts. Dependent claim coverage narrows R1 to specified unsubstituted alkyl ranges, specifies whether X is O or S, and extends coverage to pharmaceutical compositions with a pharmaceutically acceptable carrier.

Stated Advantages

Documented Applications