US 7,381,736 B2
Thiazole and thiadiazole inhibitors of tyrosine phosphatases
Zacharia S. Cheruvallath, San Diego, Calif. (US); Colin J. Loweth, San Diego, Calif. (US); Ruth F. Nutt, Santa Fe, N. Mex. (US); Darryl Rideout, San Diego, Calif. (US); Joseph E. Semple, San Diego, Calif. (US); Jing Wang, San Diego, Calif. (US); Feiyue Wu, Poway, Calif. (US); Shankari Mylvaganam, San Diego, Calif. (US); Hengyi Zhu, San Diego, Calif. (US); and Jianzhong Sun, San Diego, Calif. (US)
Assigned to Metabasis Therapeutics, Inc., La Jolla, Calif. (US)
Filed on Sep. 02, 2005, as Appl. No. 11/219,402.
Claims priority of provisional application 60/642292, filed on Jan. 06, 2005.
Claims priority of provisional application 60/638447, filed on Dec. 22, 2004.
Claims priority of provisional application 60/607034, filed on Sep. 02, 2004.
Prior Publication US 2006/0194768 A1, Aug. 31, 2006
Int. Cl. A61K 31/427 (2006.01); C07D 277/18 (2006.01)
U.S. Cl. 514—370  [548/202; 548/193] 19 Claims
 
1. A compound that has formula II:

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt, ester, enol ether, enol ester, solvate or hydrate thereof, wherein:
D is

OG Complex Work Unit Drawing
E is CH2;
s is 0;
R8 and R9 are H;
R10 is halo;
R11 is halo;
R12 is H;
R13 is CF2PO3H2;
R14 is halo;
R15 is H;
R16 is NHC(O)COOH or COOH;
and
R17 is COO-alkyl.