US 9,809,573 B2
Substituted pyridine derivatives useful as GSK-3 inhibitors
Guanglin Luo, Madison, CT (US); Ling Chen, Middletown, CT (US); Gene M. Dubowchik, Middlefield, CT (US); Swanee E. Jacutin-Porte, Madison, CT (US); Prasanna Sivaprakasam, Middletown, CT (US); and John E. Macor, Washington Crossing, PA (US)
Assigned to Bristol-Myers Squibb Company, Princeton, NJ (US)
Appl. No. 15/33,770
Filed by BRISTOL-MYERS SQUIBB COMPANY, Princeton, NJ (US)
PCT Filed Nov. 3, 2014, PCT No. PCT/US2014/063666
§ 371(c)(1), (2) Date May 2, 2016,
PCT Pub. No. WO2015/069593, PCT Pub. Date May 14, 2015.
Claims priority of provisional application 61/900,547, filed on Nov. 6, 2013.
Prior Publication US 2016/0289210 A1, Oct. 6, 2016
Int. Cl. C07D 401/12 (2006.01); C07D 401/14 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 413/14 (2006.01); C07D 417/12 (2006.01); C07D 417/14 (2006.01); C07D 487/08 (2006.01); C07D 513/04 (2006.01); C07D 213/81 (2006.01); C07D 401/04 (2006.01); C07D 405/04 (2006.01); C07D 409/04 (2006.01); C07D 413/04 (2006.01); C07D 417/04 (2006.01)
CPC C07D 401/12 (2013.01) [C07D 213/81 (2013.01); C07D 401/04 (2013.01); C07D 401/14 (2013.01); C07D 405/04 (2013.01); C07D 405/14 (2013.01); C07D 409/04 (2013.01); C07D 409/14 (2013.01); C07D 413/04 (2013.01); C07D 413/14 (2013.01); C07D 417/04 (2013.01); C07D 417/12 (2013.01); C07D 417/14 (2013.01); C07D 487/08 (2013.01); C07D 513/04 (2013.01)] 3 Claims
 
1. A compound of formula I

OG Complex Work Unit Drawing
where:
R1 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl alkylcycloalkyl, dialkylcycloalkyl, phenylcycloalkyl, hydroxycycloalkyl, or ketocycloalkyl;
R2 is hydrogen or alkyl;
R3 is hydrogen or alkyl;
or N(R2)(R3) taken together is azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, or azabicycloheptane, and is substituted with 0-4 halo or alkyl substituents;
Ar1 is 3-pyridinyl substituted with 0-3 substituents selected from cyano, halo, alkyl, haloalkyl, hydroxyalkyl, (hydroxyl)haloalkyl, alkoxyalkyl, (N(R2)(R3))alkyl, benzyl, alkenyl, cycloalkyl, hydroxy, alkoxy, haloalkoxy, (hydroxyl)alkoxy, (alkoxy)alkoxy, (cycloalkyl)alkoxy, phenoxy, alkylcarbonyl, (haloalkyl)carbonyl, phenylcarbonyl, alkoxycarbonyl, carboxy, aminocarbonyl, acetamido, N(R2)(R3) and Ar2; and
Ar2 is phenyl, naphthalenyl, pyrrolyl, furanyl, thienyl, pyrrazolyl, imidazolyl, thiazolyl, pyridinyl, pyrimidinyl, indolyl, benzofuranyl, benzothiophenyl, quinolinyl, and is substituted with 0-1 substituents selected from the group consisting of cyano, halo, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylcarbonyl, and N(R2)(R3);
or a pharmaceutically acceptable salt thereof.