US 12,286,418 B2
Compounds and methods for treating or preventing bacterial infections
Timothy Palzkill, Houston, TX (US); Doris Taylor, Houston, TX (US); Justin Anglin, Houston, TX (US); Nicholas Simmons, Houston, TX (US); John Faver, Houston, TX (US); Yong Wang, Houston, TX (US); Zhuang Jin, Houston, TX (US); and Martin Matzuk, Houston, TX (US)
Assigned to Baylor College of Medicine, Houston, TX (US)
Appl. No. 17/618,017
Filed by Baylor College of Medicine, Houston, TX (US)
PCT Filed Jun. 20, 2020, PCT No. PCT/US2020/038845
§ 371(c)(1), (2) Date Dec. 10, 2021,
PCT Pub. No. WO2020/257734, PCT Pub. Date Dec. 24, 2020.
Claims priority of provisional application 62/864,029, filed on Jun. 20, 2019.
Prior Publication US 2022/0267303 A1, Aug. 25, 2022
Int. Cl. C07D 401/14 (2006.01); C07D 401/04 (2006.01)
CPC C07D 401/14 (2013.01) [C07D 401/04 (2013.01)] 8 Claims
 
1. A compound of formula (I), or a salt, solvate, stereoisomer, tautomer, geometric isomer, C1-C6 alkyl ester, and/or C3-C8 cycloalkyl ester thereof, and any mixtures thereof:

OG Complex Work Unit Chemistry
wherein:
A1 is CH, C (halogen), or N;
A2 is CH, C (halogen), or N;
A3 is CH, C (halogen), or N;
R1 is selected from the group consisting of —C(═O) OH, 1H-tetrazolyl, —S(═O) 2OH, and —S(═O) 2NH (C1-C6 acyl);
R1′ is selected from the group consisting of H, F, Cl, Br, I, C1-C6 alkyl, and NRa1Ra2, wherein Ra1 and Ra2 are independently selected from the group consisting of H; C1-C6 alkyl optionally substituted with at least one of —OH, O (C1-C6 alkyl), —NH2, —NH (C1-C6 alkyl), and —N(C1-C6 alkyl) (C1-C6 alkyl); C1-C6 acyl optionally substituted with at least one of —OH, O (C1-C6 alkyl), —NH2, —NH (C1-C6 alkyl), and —N(C1-C6 alkyl) (C1-C6 alkyl); C-linked amino acid; and C-linked dipeptide;
R2 is selected from the group consisting of

OG Complex Work Unit Chemistry
 -C(═O) OH, —(C1-C6 alkylene) C(═O) OH, —N(Rb2) (C1-C6 alkylene) A4Rb1, —N(Rb2) (C1-C6 alkylene) C(═O) OH, —O (C1-C6 alkylene) A4Rb1, —O (C1-C6 alkylene) C(═O) OH, —N(C1-C6 alkyl)-(C1-C6 alkylene) C(═O) OH, and

OG Complex Work Unit Chemistry
wherein each occurrence of A4 is independently a bond, —CH2—, —O—, —NH—, or —NH (C1-C6 alkyl)-,
wherein each occurrence of Rb1 is independently H, C1-C6 alkyl, or phenyl optionally substituted with at least one of C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C3-C8 cycloalkoxy, —S(C1-C6 alkyl), —SO (C1-C6 alkyl), and —SO2(C1-C6 alkyl),
wherein each of the alkyl, alkoxy, cycloalkyl, and cycloalkoxy in Rb1 is optionally substituted with at least of F, Cl, Br, I, —OH, C1-C6 alkoxy, —NH2, —NH (C1-C6 alkyl), and —N(C1-C6 alkyl) (C1-C6 alkyl),
wherein each occurrence of Rb2 is independently selected from the group consisting of H and C1-C6 alkyl;
R3 is selected from the group consisting of H and —NRc1Rc2,
wherein each occurrence of Rc1 is independently selected from the group consisting of H and C1-C6 alkyl optionally substituted with at least one of —OH, —O(C1-C6 alkyl), —NH2, —NH (C1-C6 alkyl), or —N(C1-C6 alkyl) (C1-C6 alkyl), and
wherein each occurrence of Rc2 is independently H, C1-C6 alkyl, optionally substituted phenyl, optionally substituted benzoyl, C-linked amino acid, or C-linked dipeptide.