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US 2008/0167285 A1Published application
Heterosubstituted n-thiolated beta-lactam compounds and methods of use
AssigneeUniversity of South Florida
InventorsEdward Turos, Praveen Ramaraju
Life of this patent
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Abstract
The invention relates to heterosubstituted N-thiolated beta-lactams, compositions comprising these compounds, methods for their production, and methods of use as antibiotics to inhibit the growth of bacteria. The antibacterial agents of the invention can be administered to a human or animal to treat or inhibit bacterial infection, such as that of Staphylococcus species, including methicillin-resistant Staphylococcus aureus (MRSA).
Claims23
A compound having the structure shown in formula (A):
- wherein R1 is a hydrocarbon group having 1 to 8 carbon atoms;
- R3 is a heteroalkyl, heterocycloalkyl, or heteroaryl, any of which can be optionally substituted with R2, wherein R2 is one or more halides, hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, alkoxy, amido, amino, carboxylic ester group, —CHO, —COOH, or COX, wherein X is Cl, F, Br, or I;
- and
- R4, R5, and R6 are, independently, hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroalkyl, heteroaryl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, halides, hydroxyl, nitro, cyano, alkoxy, amido, amino, carboxylic ester group, —CHO, —COOH, or COX, wherein X is Cl, F, Br, or I, any of which can be optionally substituted with R2, wherein R2 is one or more halides, hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, alkoxy, amido, amino, carboxylic ester group, —CHO, —COOH, or COX, wherein X is Cl, F, Br, or I;
- and
- wherein n=0 or 1;
- or a pharmaceutically acceptable salt, hydrate, ester or amide thereof.
4 more elements
A method of synthesizing a heterosubstituted N-thiolated β-lactam of formula (A) or formula (B), comprising the steps of:
- i) reacting:
- ii) or reacting:
- wherein R1 is a hydrocarbon group having 1 to 8 carbon atoms;
- R3 is a heteroalkyl, heterocycloalkyl or heteroaryl, any of which can be optionally substituted with R2, wherein R2 is one or more halides, hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, alkoxy, amido, amino, carboxylic ester group, —CHO, —COOH, or COX, wherein X is Cl, F, Br, or I;
- and
- , R5, R6, R7, and R8 are, independently, hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroalkyl, heteroaryl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, halides, hydroxyl, nitro, cyano, alkoxy, amido, amino, carboxylic ester group, —CHO, —COOH, or COX, wherein X is Cl, F, Br, or I, any of which can be optionally substituted with R2, wherein R2 is one or more halides, hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, alkoxy, amido, amino, carboxylic ester group, —CHO, —COOH, or COX, wherein X is Cl, F, Br, or I;
- wherein n=0 or 1.
4 more elements
Dependencies are inferred from the claim text.