| US 7,589,088 B2 | ||
| Pyrimidine-based inhibitors of dipeptidyl peptidase IV and methods | ||
| Wei Meng, Pennington, N.J. (US); Lawrence G. Hamann, Cherry Hill, N.J. (US); and Robert Brigance, Levittown, Pa. (US) | ||
| Assigned to Bristol-Myers Squibb Company, Princeton, N.J. (US) | ||
| Filed on Dec. 21, 2005, as Appl. No. 11/314,795. | ||
| Claims priority of provisional application 60/640110, filed on Dec. 29, 2004. | ||
| Prior Publication US 2006/0142576 A1, Jun. 29, 2006 | ||
| Int. Cl. C07D 239/26 (2006.01); A61K 31/505 (2006.01) | ||
| U.S. Cl. 514—227.8 [514/256; 544/60; 544/242] | 15 Claims |
1. A compound of formula (I)
 n =1;
R is a substituent selected from the group consisting of hydrogen (H), halogen, cyano (CN), CF3, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, bicycloalkyl, bicycloalkylalkyl, alkylthioalkyl, arylalkylthioalkyl,
cycloalkenyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloheteroalkyl and cycloheteroalkylalkyl, wherein any such substituent
may optionally be substituted through available carbon atoms with 1, 2, 3, 4 or 5 groups selected from hydrogen, halo, alkyl,
polyhaloalkyl, alkoxy, haloalkoxy, polyhaloalkoxy, alkoxycarbonyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, polycycloalkyl,
heteroarylamino, arylamino, cycloheteroalkyl, cycloheteroalkylalkyl, hydroxy, hydroxyalkyl, nitro, cyano, amino, substituted
amino, alkylamino, dialkylamino, thiol, alkylthio, alkylcarbonyl, acyl, alkoxycarbonyl, aminocarbonyl, alkynylaminocarbonyl,
alkylaminocarbonyl, alkenylaminocarbonyl, alkylcarbonyloxy, alkylcarbonylamino, arylcarbonylamino, alkylsulfonylamino, alkylaminocarbonylamino,
alkoxycarbonylamino, alkylsulfonyl, aminosulfonyl, alkylsulfinyl, sulfonamido and sulfonyl;
B is a bond;
X is a substituent selected from the group consisting of hydrogen (H), alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl,
bicycloalkyl, bicycloalkylalkyl, alkylthioalkyl, arylalkylthioalkyl, cycloalkenyl, aryl, arylalkyl, heteroarylalkyl, saturated
cycloheteroalkyl and cycloheteroalkylalkyl, wherein any such substituent may optionally be substituted through available carbon
atoms with 1, 2, 3, 4 or 5 groups selected from hydrogen, halo, alkyl, polyhaloalkyl, alkoxy, haloalkoxy, polyhaloalkoxy,
alkoxycarbonyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, polycycloalkyl, heteroarylamino, arylamino, cycloheteroalkyl,
cycloheteroalkylalkyl, hydroxy, hydroxyalkyl, nitro, cyano, amino, substituted amino, alkylamino, dialkylamino, thiol, alkylthio,
alkylcarbonyl, acyl, alkoxycarbonyl, aminocarbonyl, alkynylaminocarbonyl, alkylaminocarbonyl, alkenylaminocarbonyl, alkylcarbonyloxy,
alkylcarbonylamino, arylcarbonylamino, alkylsulfonylamino, alkylaminocarbonylamino, alkoxycarbonylamino, alkylsulfonyl, aminosulfonyl,
alkylsulfinyl, sulfonamido and sulfonyl; or
B—X taken together can be a halogen; and
Y is aryl, optionally substituted with 1, 2, 3, 4 or 5 groups selected from hydrogen, halo, alkyl, polyhaloalkyl, alkoxy,
haloalkoxy, polyhaloalkoxy, alkoxycarbonyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, polycycloalkyl, heteroarylamino,
arylamino, cycloheteroalkyl, cycloheteroalkylalkyl, hydroxy, hydroxyalkyl, nitro, cyano, amino, substituted amino, alkylamino,
dialkylamino, thiol, alkylthio, alkylcarbonyl, acyl, alkoxycarbonyl, aminocarbonyl, alkynylaminocarbonyl, alkylaminocarbonyl,
alkenylaminocarbonyl, alkylcarbonyloxy, alkylcarbonylamino, arylcarbonylamino, alkylsulfonylamino, alkylaminocarbonylamino,
alkoxycarbonylamino, alkylsulfonyl, aminosulfonyl, alkylsulfinyl, sulfonamido and sulfonyl;
including pharmaceutically acceptable salts thereof, and all stereoisomers thereof.
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