Antimicrobials methods of making and using the same
Inventors
Duffy, Erin M. • Bhattacharjee, Ashoke • Kanyo, Zoltan F. • Ippolito, Joseph A.
Assignees
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Publication Number
US-11999739-B2
Publication Date
2024-06-04
Expiration Date
Abstract
The present disclosure relates generally to the field of antimicrobial compounds and to methods of making and using them. These compounds are useful for treating, preventing, reducing the risk of, and delaying the onset of microbial infections in humans and animals. In some embodiments, the present disclosure provides a compound of Formula (I) or tautomer thereof or a pharmaceutically acceptable salt of the compound or tautomer
Core Innovation
The invention relates to compounds of Formula (II), including a tautomer thereof or a pharmaceutically acceptable salt of the compound or tautomer. The compounds are defined by multiple variable groups, including R1, R2, R3, W, R4 through R14, X, L, and additional independently selected substituent groups, with extensive substitution possibilities while maintaining the Formula (II) framework.
The disclosed structures share a common polycyclic heteroaromatic core region, including fused heterocycles with carbonyl features, and a substituted aryl region bearing halogenation patterns such as fluoro and chloro. The substituent framework includes heteroatom-containing groups, terminal primary amines or amino groups, hydroxyl groups, methoxy or alkoxy-like substituents, and sulfur-containing substituents, together with stereochemical variations shown by wedge/dash bonds in the examples.
The patent further emphasizes ring-forming relationships among variables such as R6, R7A, X, and W/R5 that generate 5- to 6-membered heterocycloalkyl structures containing 1 to 3 heteroatoms selected from N, O, and S, optionally substituted with oxo. The disclosed scope also includes structural instantiations of the general scaffold through related Formula (I) and Formula (II) variants and multiple specific chemical structures of closely related Formula (II)-type compounds.
Claims Coverage
The independent claim defines a compound of Formula (II), including a tautomer or pharmaceutically acceptable salt, by specifying a large set of allowable substituent choices across multiple variables. Across the input items, the main inventive features center on the Formula (II) scaffold, explicit substituent definitions, and heterocycloalkyl ring-formation constraints; dependent refinements further narrow selected substituent choices and can add stereochemical constraints.
Formula (II) compound definition with variable substituents
A compound of Formula (II), or a tautomer thereof, or a pharmaceutically acceptable salt of the compound or tautomer, wherein R1, R2, R3, W, R4 through R14, X, L, and additional substituent groups are selected according to enumerated group definitions and interdependent ring-formation relationships.
Heterocycloalkyl ring formation through R6, R7A, and X
R6 and R7A together with the carbon atoms to which they are attached and the X atom connecting the two carbon atoms form a 5- to 6-membered heterocycloalkyl containing 1-3 heteroatoms selected from N, O and S, optionally substituted with oxo; in related definitions, R6 and R7A together with the carbon atoms to which they are attached form a group selected from oxo and C3-6 cycloalkyl.
W and X linkage and heteroatom selection
W is selected from N and CR4; X is selected from O and NR8; R5 is halo; and the framework permits heteroatom-linked substitutions together with selected R4 through R14 options, including halo, alkyl, haloalkyl, cycloalkyl, heteroaryl, and heterocycloalkyl choices.
Additional substituent variable definitions
R2 is selected from H, halo, C1-6 alkyl, C1-4 haloalkyl, and ORa1; R3 is selected from H, C1-6 alkyl, C1-4 haloalkyl, and C(O)ORa1; R8 and R8A are selected from H, C1-6 alkyl, C1-4 haloalkyl, 5- to 6-membered heteroaryl, and ORa3 options; and R9 through R14 and RB are defined by further enumerated substituent selections, including optional cycloalkyl and heterocycloalkyl formation.
Stereochemical constraint for a selected R6/R7A arrangement
In selected forms, R6 is H and R7A is methyl, and the carbon atom to which R7A is attached has (5) configuration per Cahn-Ingold-Prelog nomenclature.
Overall, the claim coverage centers on a Formula (II) scaffold defined by extensive enumerated substituent choices and explicit ring-formation relationships involving R6, R7A, X, and W/R5. The dependent refinements narrow specific variable selections and, in at least one case, impose a Cahn-Ingold-Prelog (5) stereochemical configuration for a defined variable pattern.
Stated Advantages
Treating or preventing microbial infection in humans or animals.
Reducing risk of microbial infection in humans or animals.
Delaying onset of microbial infection in humans or animals.
Documented Applications
Pharmaceutical compositions containing the described compounds.
Treating microbial infection in humans or animals.
Preventing microbial infection in humans or animals.
Reducing risk of microbial infection in humans or animals.
Delaying onset of microbial infection in humans or animals.
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