US 7,601,695 B2
Antibacterial agents
Chang-Hsing Liang, San Diego, Calif. (US); Jonathan Duffield, San Diego, Calif. (US); Alex Romero, San Diego, Calif. (US); Yu-Hung Chiu, San Diego, Calif. (US); David Rabuka, San Diego, Calif. (US); Sulan Yao, San Diego, Calif. (US); Steve Sucheck, Maumee, Ohio (US); Kenneth Marby, San Diego, Calif. (US); Youe-kong Shue, San Diego, Calif. (US); Yoshi Ichikawa, San Diego, Calif. (US); and Chan-Kou Hwang, San Diego, Calif. (US)
Assigned to Optimer Pharmaceuticals, Inc., San Diego, Calif. (US)
Appl. No. 10/548,698
PCT Filed Mar. 05, 2004, PCT No. PCT/US2004/006645
§ 371(c)(1), (2), (4) Date Sep. 09, 2005,
PCT Pub. No. WO2004/080391, PCT Pub. Date Sep. 23, 2004.
Claims priority of provisional application 60/453601, filed on Mar. 10, 2003.
Claims priority of provisional application 60/468242, filed on May 06, 2003.
Prior Publication US 2006/0100164 A1, May 11, 2006
Int. Cl. A61K 31/70 (2006.01); C07H 17/08 (2006.01)
U.S. Cl. 514—29  [536/7.2; 536/7.4] 30 Claims
 
1. A compound according to Formula 1 or Formula 2, or pharmaceutically acceptable salts, hydrates, solvates, esters or prodrugs thereof

OG Complex Work Unit Drawing
wherein:
R1 is selected from the group consisting of H, cyclic and acyclic alkyl, cyclic and acyclic alkyl-hydroxyamine, aryl, aryl-hydroxyamine, cyclic and acyclic acyl, cyclic and acyclic acyl-hydroxyamine, heteroalkyl, heteroalkyl-hydroxyamine, heteroaryl, heteroaryl-hydroxyamine, acylaryl, acylaryl-hydroxyamine, acylheteroaryl, acylheteroaryl-hydroxyamine, alkylaryl, alkylaryl-hydroxyamine, alkylheteroaryl, alkylheteroaryl-hydroxyamine, sulfonylalkyl, sulfonylalkyl-hydroxyamine, acylalkoxylsulfonylalkyl, and acylalkoxylsulfonylalkyl-hydroxyamine;
or R1 is —C(O)—NR4R5, where R4 and R5 are each independently selected from the group consisting of hydrogen, hydroxy, alkyl, aralkyl, alkylaryl, alkoxy, heteroalkyl, aryl, heteroaryl, dimethylaminoalkyl, acyl, sulfonyl, ureido, and carbamoyl;
or R1 is a monosaccharide, a disaccharide or a trisaccharide, providing that R1 is not desosamine or an oxidized, reduced or substituted desosamine;
R2 and R3 are each OH, or R2 and R3 are taken together with the attached carbons to form a heterocycle of the formula:

OG Complex Work Unit Drawing
where Z is O, or —N(R6); where R6 is hydrogen, hydroxy, alkyl, alkoxy, heteroalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, dimethylaminoalkyl, acyl, or sulfonyl;
X is H; and Y is OR7; where R7 is a monosaccharide or disaccharide, alkyl, aryl, heteroaryl, acyl-, or —C(O)—NR8R9, where R8 and R9 are each independently selected from the group consisting of hydrogen, hydroxy, alkyl, aralkyl, alkylaryl, heteroalkyl, aryl, heteroaryl, alkoxy, dimethylaminoalkyl, acyl, sulfonyl, ureido, and carbamoyl;
or X and Y are taken together with the attached carbon to form carbonyl;
V is —C(O)—, —C(═NR11)—, —CH(NR12, R13)—, or —N(R14)CH2—, where N(R14) is attached to the C-10 carbon of the compounds of Formulae 1 and 2; wherein R11 is hydroxy or alkoxy, R12 and R13 are each independently selected from the group consisting of hydrogen, hydroxy, alkyl, aralkyl, alkylaryl, alkoxy, heteroalkyl, aryl, heteroaryl, dimethylaminoalkyl, acyl, sulfonyl, ureido, and carbamoyl; R14 is hydrogen, hydroxy, alkyl, aralkyl, alkylaryl, alkoxy, heteroalkyl, aryl, heteroaryl, dimethylaminoalkyl, acyl, sulfonyl, ureido, or carbamoyl;
W is H, F, Cl, Br, I, or OH;
A is —CH2—, —C(O)—, —C(O)O—, —C(O)NH—, —S(O)2—, —S(O)2NH—, or —C(O)NHS(O)2—;
B is —(CH2)n— where n is an integer ranging from 0-10, or B is an unsaturated carbon chain of 2-10 carbons;
C is hydrogen, hydroxy, alkyl, aralkyl, alkylaryl, alkoxy, heteroalkyl, aryl, heteroaryl, aminoaryl, alkylaminoaryl, acyl, acyloxy, sulfonyl, ureido, or carbamoyl; and R10 is hydrogen or acyl.