US 7,592,477 B2
Substituted methylene amide derivatives as modulators of protein tyrosine phosphatases (PTPs)
Dominique Swinnen, Beaumont (France); Agnes Bombrun, Monnetier-Mornex (France); Jerome Gonzalez, Annemasse (France); Patrick Gerber, Villars-sous-Yens (Switzerland); and Pierre-Andre Pittet, Gilly (Switzerland)
Assigned to Laboratoires Serono SA, Coinsins (Switzerland)
Appl. No. 10/501,344
PCT Filed Jan. 27, 2003, PCT No. PCT/EP03/00808
§ 371(c)(1), (2), (4) Date Jan. 26, 2005,
PCT Pub. No. WO03/064376, PCT Pub. Date Aug. 07, 2003.
Claims priority of application No. 02100078 (EP), filed on Jan. 29, 2002; and application No. 02100410 (EP), filed on Apr. 25, 2002.
Prior Publication US 2005/0124656 A1, Jun. 09, 2005
Int. Cl. C07C 229/00 (2006.01); C07D 271/06 (2006.01)
U.S. Cl. 560—37  [548/131] 15 Claims
 
1. A substituted methylene amide of Formula (I):
as well as its geometrical isomers, its optically active forms as enantiomers,

OG Complex Work Unit Drawing
diastereomers and its racemate forms, as well as pharmaceutically acceptable salts thereof, wherein
(I)
R1 is CH2—CH2-phenyl, CH2—CH2-napthyl, CH2-phenyl, or CH2-napthyl;
R2a and R2b are each independently are H or (C1-C12)alkyl;
Cy is a phenyl substituted by (1), (2) or (3):
(1) an oxadiazole group;
(2) 1 or 2 moieties selected from the group consisting of —NH—CO—R3, —SO2—NR3R3′ and —CO—NR3R3′ wherein R3 and R3′ are independently selected from H and (C1-C15)alkyl; or
(3) B-R4 wherein B is an ethynyl group and R4 is a (C1-C12)alkyl phenyl;
(II)
R2a and R2b are each H, R1 is —CH2-A with A being phenyl optionally substituted by cyano, halogen, methoxy, hydroxyl, phenoxy, —NO2, or trifluoromethyl, and Cy is phenyl or biphenyl substituted by —SO2R3, or —CO—NR3R3′ where R3′ is H and R3 is (C7-C12)alkyl or (C7-C15)alkyl; or
(III)
R2a and R2b are each H, R1 is selected from the group consisting of phenyl, benzyl, phenethyl, or 1-methylbenzyl which may be substituted by (C1-C6)alkyl or cycloalkyl, and Cy is phenyl or biphenyl substituted by —SO2R3, or —CO—NR3R3 where R3 is (C7-C1 5)alkyl.