| 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. |
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| 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,
![]() (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.
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