US 7,482,336 B2
Aminocyclohexanes as dipeptidyl peptidase-IV inhibitors for the treatment or prevention of diabetes
Tesfaye Biftu, Freehold, N.J. (US); Danqing Feng, Branchburg, N.J. (US); Ying-Duo Gao, Edison, N.J. (US); Suresh Singh, Kendall Park, N.J. (US); and Ann E. Weber, Scotch Plains, N.J. (US)
Assigned to Merck & Co., Inc., Rahway, N.J. (US)
Appl. No. 11/628,686
PCT Filed Jun. 17, 2005, PCT No. PCT/US2005/021556
§ 371(c)(1), (2), (4) Date Dec. 06, 2006,
PCT Pub. No. WO2006/009886, PCT Pub. Date Jan. 26, 2006.
Claims priority of provisional application 60/581536, filed on Jun. 21, 2004.
Prior Publication US 2007/0254865 A1, Nov. 01, 2007
Int. Cl. A01N 43/00 (2006.01); A01N 43/58 (2006.01); A01N 43/60 (2006.01); A01N 43/90 (2006.01); A01N 43/38 (2006.01); A61K 31/00 (2006.01); A61K 31/50 (2006.01); A61K 31/495 (2006.01); A61K 31/519 (2006.01); A61K 31/40 (2006.01); C07D 243/00 (2006.01); C07D 471/00 (2006.01)
U.S. Cl. 514—211.03  [514/249; 514/264.1; 514/416; 540/492; 544/279; 546/117; 548/471] 13 Claims
 
1. A compound of the formula I:

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt thereof; wherein
X is a bond;
Ar is phenyl unsubstituted or substituted with one to five R1 substituents;
each R1 is independently selected from the group consisting of fluorine, chlorine, bromine, methyl, trifluoromethyl, and trifluoromethoxy;
R3 and R4 together with the nitrogen atom to which they are attached form an optionally fused nitrogen-containing heterocyclic ring selected from the group consisting of:

OG Complex Work Unit Drawing

OG Complex Work Unit Drawing

OG Complex Work Unit Drawing
wherein said heterocyclic ring is unsubstituted or substituted with one to three Ra substituents independently selected from oxo, hydroxy, halogen, C3-6 cycloalkyl, C1-4 alkoxy, and C1-4 alkyl, wherein cycloalkyl, alkyl and alkoxy are unsubstituted or substituted with one to five fluorines.