Antimicrobial compounds and methods
OwnerPaul R. Sebahar, Ryan E. Looper +6inventors
InventorsPaul R. Sebahar, Ryan E. Looper, Seth Grant, Hariprasada R. Kanna Reddy, Ben Isaac C. Tresco, Travis J. Haussener, Daniel Feodore Zigar, Charles A. Testa
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Abstract
The invention is directed to compounds that are active as antibacterial agents. The invention compounds are active against gram-positive and gram-negative bacteria and can be used to treat infections caused by gram-positive and gram-negative bacteria. Also disclosed are processes and intermediates for making the compounds.
Claims61
A compound of formula I:
- or a single stereoisomer or mixture of stereoisomers thereof, or a pharmaceutically acceptable salt thereof, wherein:
- ring A is a 3-8 membered monocyclic heterocycloalkylene optionally substituted with up to three substituents independently selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halo, CN, C1-C6 haloalkyl, phenyl, OH, NH2, NH(C1-C6 alkyl), N(C1-C6 alkyl)2, COOH, COO(C1-C6 alkyl), CONH2, CONH(C1-C6 alkyl), CON(C1-C6 alkyl)2, and oxo;
- J is C1-C6 alkylene or C3-C8 cycloalkylene, either of which is optionally substituted with halo, OH, or C1-C6 alkoxy, wherein up to two methylene units of the C1-C6 alkylene are optionally and independently replaced with O, S, SO, SO2, or C═O;
- Y is a bond or C1-C6 alkylene optionally substituted with OH, NH2, CN, halo, or C1-C6 alkoxy, wherein up to two methylene units of the C1-C6 alkylene are optionally and independently replaced by O, NH, N—(C1-C6 alkyl), N—(C1-C6 hydroxyalkyl), N—(C1-C6 haloalkyl), N—(C1-6 alkylene-C3-8 cycloalkyl), N—(C3-8 cycloalkyl), NH(C═O), N—(C1-6 alkyl)(C═O), or (C═O);
- ring B is a 3-8 membered monocyclic cycloalkylene, 3-8 membered monocyclic heterocycloalkylene, 6-12 membered bicyclic cycloalkylene, or a 6-12 membered bicyclic heterocycloalkylene, each of which is optionally substituted with up to three substituents independently selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halo, CN, C1-C6 haloalkyl, OH, COOH, COO(C1-C6 alkyl), CONH2, CONH(C1-C6 alkyl), CON(C1-C6 alkyl)2, and C1-C6 hydroxyalkyl;
- L is a bond or C1-C6 alkylene, wherein up to two methylene units of the C1-C6 alkylene may independently be replaced with 0, NH, (C═O), NH(C═O), N—(C1-6 alkyl)(C═O), (C═NH), NH(C═N), or N—(C1-6 alkyl);
- R1 and R2 are each independently selected from the group consisting of C1-C6 alkyl, halo, CN, OH, NH2, O(C1-C6 haloalkyl), NH(C1-C6 alkyl), N(C1-C6 alkyl)2, —COO(C1-C6 alkyl), CONH2, C1-C6 haloalkyl, C1-C6 alkoxy, and C1-C6 haloalkoxy;
- Rx, Ry, Rx′, and Ry′ are each independently H, C1-C6 alkyl, or an amino protecting group;
- m and n are each independently 0, 1, 2, or 3;
- and
- represents a single bond or a double bond.
A compound, or a single stereoisomer or mixture of stereoisomers thereof, or a pharmaceutically acceptable salt thereof, which is listed in Table 1 and Table 2.
A compound, or a single stereoisomer or mixture of stereoisomers thereof, or a pharmaceutically acceptable salt thereof, which is listed in Table 2.
Dependencies are inferred from the claim text.