Antimicrobial compounds and methods of making and using the same
Inventors
Kanyo, Zoltan F. • Bhattacharjee, Ashoke • Duffy, Erin M. • Marra, Andrea
Assignees
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Publication Number
US-10106543-B2
Publication Date
2018-10-23
Expiration Date
Abstract
The present invention 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.
Core Innovation
The invention relates to compounds of Formula (I), including tautomers thereof, and pharmaceutically acceptable salts, esters, and prodrugs of said compound or tautomer. The compounds are defined by extensive structural variability through substituent variables R1 to R15 and framework variables X, Y, Z, and W, together with ring-forming combinations that determine heterocycloalkyl and heteroaryl structures and their permitted ring sizes and heteroatom counts.
The structural definition includes conditional relationships among substituents, including cases where R1 is H or F with corresponding constraints on R2 and R3, and further options for R4, R5, R6, R7, R11, R12, R14, and R15. The scaffold also permits fluorinated and halogenated substituent patterns, including CF3, OCF3, SCF3, SOCF3, halo, Cl, and alkyl or alkoxyl options, together with ring-forming combinations that generate 5- to 8-membered, 5- to 12-membered, and related saturated heterocycloalkyl or heteroaryl systems.
A further structural proviso restricts certain combinations of X, R6, and R14 by requiring that at least one of a listed set of substituents is not H under a defined condition. The disclosure also includes pharmaceutical compositions comprising a pharmaceutically acceptable carrier and a compound of Formula (I) or a tautomer, salt, ester, or prodrug thereof, and describes antibacterial use contexts and ribosome-binding antimicrobial agents.
Claims Coverage
The provided material identifies one independent claim directed to a compound of Formula (I) and its tautomer, pharmaceutically acceptable salt, ester, and prodrug forms. The independent claim is defined by extensive substituent and ring-forming variables and includes one conditional proviso excluding a specific all-H configuration under a defined set of X, R6, and R14 values.
Formula (I) compound scaffold with derivative forms
A compound of Formula (I) or a tautomer thereof, or a pharmaceutically acceptable salt, ester, or prodrug of said compound or tautomer, defined by substituent variables R1 to R15 and framework variables X, Y, Z, and W.
Conditional R1 to R3 substitution pattern
R1 is H or F, with corresponding constraints on R2 and R3, including CF3, OCF3, SCF3, SOCF3, halo, Cl, and C1-C6 alkyl or halo-substituted alkyl options.
Ring-forming constraints controlled by X, Y, and Z
R4, R5, R6, R7, R8, R10, R11, and R12 are defined with options for open substituents or ring-forming combinations that produce 5- to 8-membered or 5- to 12-membered heterocycloalkyl or saturated heterocycloalkyl rings, with specified heteroatom counts and optional oxo substitution.
Q1-T1 and related substituent framework
R11 is Q1-T1 with Q1 as a bond or C1-C3 alkyl linker and T1 selected from defined substituent classes; related variables Q2 and T2, together with Rc and A, further expand the allowed heteroatom-containing substituent space.
Conditional proviso excluding a specific structural combination
Provided that when R14 is C(=NR16)NH2, X is CH2, and R6 is CH2OCH3, then at least one of R4, R5, R7, R8, R10, R11, R12, or R15 is not H.
Pharmaceutical composition with pharmaceutically acceptable carrier
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of Formula (I), including tautomer, salt, ester, or prodrug forms.
Claim coverage centers on a broad Formula (I) scaffold with conditional substituent logic, ring-forming constraints, and a specific proviso limiting one structural combination. The claim set also includes a pharmaceutical composition with a pharmaceutically acceptable carrier.
Stated Advantages
Antibacterial activity targeting bacterial ribosomes.
Used for treating, preventing, reducing risk of, and delaying the onset of microbial infections.
Therapeutic use is stated for gram-positive and gram-negative microorganisms, including resistant isolates.
Documented Applications
Antibacterial treatment against microbial infections, including infections associated with gram-positive and gram-negative microorganisms and resistant isolates.
Treating or preventing microbial infections.
Use contexts include CAP, cSSSI, cUTI, HAP, VAP, complicated intra-abdominal infection, and stents.
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