US 7,579,357 B2
Dipeptidyl peptidase inhibitors
Jun Feng, Carlsbad, Calif. (US); Stephen L. Gwaltney, II, San Diego, Calif. (US); Stephen W. Kaldor, San Diego, Calif. (US); Jeffrey A. Stafford, San Diego, Calif. (US); Michael B. Wallace, San Diego, Calif. (US); and Zhlyuan Zhang, San Diego, Calif. (US)
Assigned to Takeda Pharmaceutical Company Limited, Osaka (Japan)
Filed on Aug. 12, 2004, as Appl. No. 10/918,326.
Claims priority of provisional application 60/495238, filed on Aug. 13, 2003.
Prior Publication US 2005/0070706 A1, Mar. 31, 2005
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/04 (2006.01); A61K 31/506 (2006.01)
U.S. Cl. 514—269  [544/319] 44 Claims
 
1. A compound having Formula XV:

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt thereof, wherein
Q is selected from the group consisting of CO, and C═NR4;
R2 and R3 are each independently selected from the group consisting of hydrogen, halo, perhalo(C1-10)alkyl, amino, cyano, nitro, thio, (C1-10)alkyl, alkene, alkyne, (C3-12)cycloalkyl, hetero(C3-12)cycloalkyl, aryl(C1-10)alkyl, heteroaryl(C1-5)alkyl, (C9-12)bicycloaryl, hetero(C8-12)bicycloaryl, carbonyl(C1-3)alkyl, thiocarbonyl(C1-3)alkyl, sulfonyl(C1-3)alkyl, sulfinyl (C1-3)alkyl, imino(C1-3)alkyl, aryl, heteroaryl, hydroxy, alkoxy, aryloxy, heteroaryloxy, alkenyl, and alkynyl, each substituted or unsubstituted;
R4 is selected from the group consisting of hydrogen, (C1-10)alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, bicycloaryl, heterobicycloaryl, each substituted or unsubstituted;
M and R19 are taken together to form a moiety selected from the group consisting of 3-amino-piperidinyl-1-yl, 3-aminomethyl-pyrrolidin-1-yl, 2-aminoazetidin-1-yl, 3-aminoazetidin-1-yl, 3-amino-3-methylpiperidin-1-yl, 3-aminocyclopent-1-yl, 3-aminomethylcyclopent-1-yl, 3-aminomethylcyclohex-1-yl, 3-aminohexahydroazepin-1-yl, 3-amino-cyclohex-1-yl, piperazin-1-yl, homopiperazin-1-yl, 3-amino-pyrrolidin-1-yl, and R-3-aminopiperiden-1-yl, each substituted or unsubstituted;
L and X are taken together to form a substituted or unsubstituted —(CH2)-(2-cyano)-phenyl.