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US 2003/0191108 A1Published application
N-thiolated beta-lactams: novel antibacterial agents for methicillin-resistant staphylococcus aureus
AssigneeUniversity of South Florida
InventorEdward Turos
Life of this patent
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Abstract
The invention relates generally to novel N-thiolated β-lactams. More specially, the invention relates to the use of these novel antibacterial agents in the treatment or inhibition of methicillin-resistant Staphylococcus aureaus.
Claims9
A monocyclic β-lactam compound of the formula:
- 13
- or a salt or hydrate thereof, wherein:
- —C(R1)3 is aryl, or heteroaryl;
- —X(R2)n is hydrogen, methoxy, acetoxy, phenoxy, or X(R2)n and R4 forms a spirocycle;
- R3 is alkynyl, alkenyl, acetyl, aryl, heteroaryl, aryl(C1-C6) alkyl, heteroaryl(C1-C6) alkyl, aryl(C2-C6) alkenyl, heteroaryl(C2-C6)alkenyl, aryl(C2-C6) alkynyl or heteroaryl(C2-C6)alkynyl;
- wherein any aryl or heteroaryl is optionally substituted with halo, nitro, cyano, hydroxy, trifluoromethyl, trifluoromethoxy, (C1-C15)alkyl, (C2-C15)alkenyl, (C2-C15)alkynyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl(C1-C15)alkoxy, (C3-C8)cycloalkyl-(C2-C15) alkenyl, C3-C8)cycloalkyl(C2-C15)alkynyl, (C1-C15)alkoxy, (C1-C15)alkanoyl, (C1-C15)alkanoyloxy, C(O)O(C1-C6)alkyl, C(═O)N((C1-C6)alkyl)2, or N((C1-C6)alkyl)2;
- R4 is hydrogen, or X(R2)n and R4 forms a spirocycle;
- R5 is hydrogen;
- and
- excluding the compounds 3-methoxy-1-methylthio-4-phenylethynyl-2-oxoazetidine, and 4-(1-acetoxy-3-phenyl-2-propynyl)-3-methoxy-2-oxoazetidine.
7 more elements
A mechanism of inhibiting infection comprising administering a N-thiolated β-lactam antibacterial compound to a patient in need thereof, wherein said antibacterial compound affects developmental events within the cytoplasm of the cell.
A method of inhibiting bacterial infection comprising:
- administering an N-thiolated β-lactam antibacterial compound to a patient in need thereof, wherein a biological electrophile activates said antibacterial compound;
- and wherein said agent inactivates biological nucleophiles required for cell growth of said bacterial infection.
A monocyclic β-lactam compound of the formula:
- 14
- or a salt or hydrate thereof, wherein:
- —C(R1)3 is alkyl or heteroalkyl;
- —X(R2)n is OSO2R6;
- R3 is alkynyl, alkenyl, acetyl, aryl, heteroaryl, aryl(C1-C6) alkyl, heteroaryl(C1-C6) alkyl, aryl(C2-C6) alkenyl, heteroaryl(C2-C6)alkenyl, aryl(C2-C6) alkynyl or heteroaryl(C2-C6)alkynyl;
- wherein any aryl or heteroaryl is optionally substituted with halo, nitro, cyano, hydroxy, trifluoromethyl, trifluoromethoxy, (C1-C15)alkyl, (C2-C15)alkenyl, (C2-C15)alkynyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl(C1-C15)alkoxy, (C3-C8)cycloalkyy-(C2-C15) alkenyl, C3-C8)cycloalkyl(C2-C15)alkynyl, (C1-C15)alkoxy, (C1-C15)alkanoyl, (C1-C15)alkanoyloxy, C(O)O(C1-C6)alkyl, C(═O)N((C1-C6)alkyl)2, or N((C1-C6)alkyl)2;
- R4 is hydrogen;
- R5 is hydrogen;
5 more elements
Dependencies are inferred from the claim text.