US 7,521,557 B2
Pyrrolopyridine-based inhibitors of dipeptidyl peptidase IV and methods
Pratik Devasthale, Plainsboro, N.J. (US); Wei Wang, Princeton, N.J. (US); Lawrence G. Hamann, North Grafton, Mass. (US); and John M. Fevig, Doylestown, Pa. (US)
Assigned to Bristol-Myers Squibb Company, Princeton, N.J. (US)
Filed on May 09, 2006, as Appl. No. 11/430,657.
Claims priority of provisional application 60/682968, filed on May 20, 2005.
Prior Publication US 2006/0264457 A1, Nov. 23, 2006
Int. Cl. C07D 471/02 (2006.01); A01N 43/42 (2006.01)
U.S. Cl. 546—113  [514/300] 19 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Drawing
wherein
represents one or two double bonds in the 5-membered ring of I, and the six-membered ring of I is an aromatic ring;
n is 1 or 2;
R is;
X and Z are the same or different and are independently selected from the group consisting of CH2, CH, C═O, C═CR3R4, C═S, C═NR3, and CR3R4, wherein R3 and R4 are alkyl or aryl;
A is selected from the group consisting of hydrogen (H), alkyl, cycloalkyl which is cyclopentyl phenyl, phenylalkyl, heteroarylalkyl, where heteroaryl is pyrazolyl, oxazolyl or isooxazolyl, cycloheteroalkyl which is pyrrolidinyl, piperidinyl, tetrahydropyranyl or tetrahydrothiopyranyl, cycloheteroalkylalkyl where the cycloheteroalkyl group is tetrahydrofuranyl, pyrrolidinyl, oxazolidinyl, or thiazolidinyl, —C(O)—NR1R2, or —C(O)—OR1, wherein any such group may optionally be substituted with 1 to 3 substituents (where possible) independently selected from the group consisting of hydrogen, halo, alkyl, polyhaloalkyl, alkoxy, haloalkoxy, polyhaloalkoxy, carboxy, alkoxycarbonyl, cycloalkyl, heteroarylamino, cycloheteroalkyl, cycloheteroalkylalkyl, cyclopropylsulfonyl, cycloheteroalkylaminocarbonyl, cycloheteroalkylcarbonyl, heteroarylaminocarbonyl, cycloheteroalkyl(alkyl)aminocarbonyl, cycloalkylsulfonyl(alkyl)amino, hydroxy, hydroxyalkyl, cyano, amino, substituted amino, alkylamino, dialkylamino, alkylthio, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, (where the alkyls are the same or different), alkylcarbonylamino, alkylsulfonylamino, alkylaminocarbonylamino, alkoxycarbonylamino, alkylsulfonyl, phenylsulfonyl, alkylsulfinyl, and sulfonyl;
wherein heteroaryl in the above substituents is pyrazolyl, isooxazolyl, pyridinyl, or pyrimidinyl; and
wherein cycloheteroalkyl in the above substituents is tetrahydrofuranyl, pyrrolidinyl, oxazolidinyl, thiazolidinyl, tetrahydropyranyl, piperidinyl, morpholinyl, piperazinyl, or indolinyl;
R1 and R2 are the same or different and are each indepedently selected from the group consisting of hydrogen (H), alkyl, phenyl, phenylalkyl, heteroaryl which is pyrazolyl, heteroarylalkyl which is pyrazolylalkyl or pyridinylalkyl, cycloheteroalkyl which is tetrahydropyranyl or piperidinyl, wherein such group may optionally be substituted with 1 to 3 substitutents (where possible) independently selected from the group consisting of hydrogen, and alkyl; and
Y is phenyl, wherein said phenyl group may optionally be substituted with 1-5 substituents independently selected from the group consisting of hydrogen, and halo; or a pharmaceutically acceptable salt thereof, all stereoisomers thereof.