Patent ID: 8338465

Claim:
A method of treating infection with Mycobacterium tuberculosis comprising administering to a subject a therapeutically effective amount of a compound of formula I: wherein: A is chosen from oxygen and sulfur; X is chosen from the group consisting of a direct bond, (C 1 -C 6 )alkylene in which one of the hydrogens is optionally replaced with a group —(CH 2 ) q COOH wherein q is 0-6, —NH—, —NHSO 2 —, and —NHC(═O)—; Y is chosen from the group consisting of (C 1 -C 10 )alkylene, (C 1 -C 10 )oxaalkylene, (C 1 -C 10 )alkylene in which one or more hydrogens is replaced with (C 1 -C 6 )alkyl, substituted (C 1 -C 6 )alkyl, aryl, substituted aryl or heteroaryl, aryl, substituted aryl, heterocyclyl, and cycloalkyl; Z is (CH 2 ) p —R 1 where p is 0-6; Q is chosen from the group consisting of a direct bond, -oxygen-, —CH 2 —, —CH 2 O—, —CH 2 S—, —O—C(═O)—, —C(═O)O— and —C(═O)—NR 13 —; R 1 is chosen from the group consisting of —COOR 3 , —OR 4 , —P(═O)(OR 5 ) 2 , —O—C(═O)NR 6 R 7 , —SO 2 NR 8 R 9 , —CONR 10 R 11 , —OCH 2 —COOR 3 , —CO—(C 1 -C 6 alkyl), —CO—(C 1 -C 6 alkyl)-OH, and —CO—(C 1 -C 6 alkyl)COOH; R 3 is chosen from the group consisting of H, (C 1 -C 10 )alkyl, (C 1 -C 10 )oxaalkyl, hydroxy(C 1 -C 10 )alkyl, hydroxy(C 1 -C 10 )oxaalkyl, (C 1 -C 10 )azaalkyl, hydroxy(C 1 -C 10 )azaalkyl and (C 1 -C 10 )alkyl-OPO 3 H; R 4 , R 5 , R 6 , R 7 , R 8 , and R 13 are chosen from H and (C 1 -C 6 )alkyl; R 9 is chosen from the group consisting of H, (C 1 -C 6 )alkyl and —C(═O)R 12 ; R 10 and R 11 are each independently chosen from the group consisting of H, (C 1 -C 6 )alkyl and (C 1 -C 6 )hydroxyalkyl; R 12 is chosen from the group consisting of (C 1 -C 6 )alkyl, aryl and heteroaryl; P is chosen from the group consisting of H, (C 1 -C 6 )alkyl, O(C 1 -C 6 )alkyl and F; Het is a 5-membered or 6-membered heterocyclic ring; and R is chosen from optionally substituted aryl and heterocyclyl; with the provisos that when —X—Y—Z is CH 2 CH 2 COOH, -Het-Q-R is not 5-(3-trifluoromethylphenyl)-furan-2-yl, and when —X—Y—Z is CH 2 COOH, -Het-Q-R is not 5-(2,3-dichlorophenyl)-furan-2-yl.