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US 8,575,144 B2Granted
Beta-lactamase inhibitory compounds
AssigneeSouthern Methodist University
InventorsJohn D. Buynak, Anjaneyulu Sheri, Sundar Ram Reddy Pagadala
Life of this patent
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Abstract
Inhibitors of the enzyme beta-lactamase are provided comprising compounds of formula (II) wherein R1 or R2 is a pyridyl group and R5 is a group of formula The compounds are adapted to inhibit beta-lactamase as produced by beta-lactam resistant bacterial strains. Methods of treatment of beta-lactam resistant bacterial infections in patients are provided.
Claims10
A beta-lactamase-inhibitory compound of Formula (II):
- wherein p is 0, 1, or 2;
- R1 and R2 each independently is H or pyridyl, wherein any pyridyl can be independently substituted with 0-3 J;
- J is haloalkyl, (CH2)n—OR′, (CH2)n—OC(O)N(R′)2, (CH2)n—CN, CF3, OCF3, O, S, C(O), S(O), methylenedioxy, ethylenedioxy, (CH2)n—N(R′)2, (CH2)n—SR′, (CH2)n—S(O)R′, (CH2)n—S(O)2R′, (CH2)n—S(O)2N(R′)2, (CH2)n—SO3R′, (CH2)n—C(O)R′, (CH2)n—C(O)C(O)R′, (CH2)n—C(O)CH2C(O)R′, (CH2)n—C(S)R′, (CH2)n—C(O)OR′, (CH2)n—OC(O)R′, (CH2)n—C(O)N(R′)2, (CH2)n—OC(O)N(R′)2, (CH2)n—C(S)N(R′)2, (CH2)n—NHC(O)R′, (CH2)n—N(R′)N(R′)C(O)R′, (CH2)n—N(R′)N(R′)C(O)OR′, (CH2)n—N(R′)N(R′)CON(R′)2, (CH2)n—N(R′)SO2R′, (CH2)n—N(R′)SO2N(R′)2, (CH2)n—N(R′)C(O)OR′, (CH2)n—N(R′)C(O)R′, (CH2), —N(R′)C(S)R′, (CH2)n—N(R′)C(O)N(R′)2, (CH2)n—N(R′)C(S)N(R′)2, (CH2)n—N(R′)C(═NR)N(R′)2, (CH2)n—C(═NR)N(R′)2, (CH2)n—N(COR′)COR′, (CH2)n—N(OR′)R′, (CH2)n—C(═NH)N(R′)2, (CH2)n—C(O)N(OR′)R′, (CH2)nN(R′)C(═NR′)N(R′)2 or (CH2)n—C(═NOR′)R′, wherein n is 0 to 4, and wherein;
- each R′ is independently at each occurrence hydrogen, (C1-C12)-alkyl, (C3-C10)-cycloalkyl or (C3-C10)-cycloalkenyl, [(C3-C10)cycloalkyl or (C3-C10)-cycloalkenyl]-(C1-C12)-alkyl, (C6-C10)-aryl, (C6-C10)-aryl-(C1-C12)-alkyl, (C3-C10)-heterocyclyl, (C3-C10)-heterocyclyl-(C1-C12)-alkyl, (C5-C10)-heteroaryl, or (C5-C10)-heteroaryl-(C1-C12)-alkyl, or, two R′ groups together with a nitrogen atom to which both R′ groups are attached or with two adjacent nitrogen atoms to which each R′ group is respectively attached form a mono- or bicyclic ring system;
- R4 is H, a (C1-C6)alkyl or aryl group, or a pharmaceutically acceptable cation;
- R5 is a group of formula
- or a salt, pharmaceutically acceptable salt, tautomer, or stereoisomer thereof.
4 more elements
Dependencies are inferred from the claim text.