US 7,589,232 B2
Alkynyl aryl carboxamides
Dominique Swinnen, Beaumont (France); Patrick Gerber, Etoy (Switzerland); Jerome Gonzalez, Annemasse (France); Agnes Bombrun, Monnetier-Mornex (France); and Catherine Jorand-Lebrun, Contamine-Sarzin (France)
Assigned to Laboratories Serono S.A., Coinsins (Switzerland)
Appl. No. 10/565,538
PCT Filed Jul. 20, 2004, PCT No. PCT/EP2004/051557
§ 371(c)(1), (2), (4) Date Jan. 23, 2006,
PCT Pub. No. WO2005/012280, PCT Pub. Date Feb. 10, 2005.
Claims priority of provisional application 60/517993, filed on Nov. 06, 2003.
Claims priority of application No. 03102235 (EP), filed on Jul. 21, 2003.
Prior Publication US 2007/0105913 A1, May 10, 2007
Int. Cl. C07C 299/34 (2006.01); A61K 31/195 (2006.01)
U.S. Cl. 562—455  [514/563; 514/403; 514/355; 514/443; 514/452; 514/453; 548/361.1; 546/316; 549/49; 549/232] 25 Claims
 
1. A method of treating at least one disease, in a mammal in need thereof, wherein the at least one disease is selected from the group consisting of diabetes, inadequate glucose tolerance, hyperlipidemia, hypertriglyceridemia, hypercholerstrolemia, obesity, and polycystic ovary syndrome, comprising
administering at least one alkynyl aryl carboxamide of Formula (I′)

OG Complex Work Unit Drawing
as well as its geometrical isomers, its optically active forms as enantiomers, diastereomers and its racemate forms, as well as pharmaceutically acceptable salts thereof, wherein
A is a C2-C15 alkynyl, or C2-C6-alkynyl aryl;
Cy is an aryl;
Cy′ is an aryl, which may optionally be fused by a 3-8 membered cycloalkyl;
n is 0 or 1;
R1 and R2 are independently from each other selected from the group consisting of hydrogen and C1-C6-alkyl;
R3 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkyl amine, C1-C6-alkyl alkoxy, C1-C6-alkyl carboxy, aryl, heteroaryl, saturated or unsaturated 3-8-membered cycloalkyl, 3-8-membered heterocycloalkyl, C1-C6-alkyl aryl, C1-C6-alkyl heteroaryl, C2-C6-alkenyl aryl, C2-C6-alkenyl heteroaryl, C2-C6-alkynyl aryl; C2-C6-alkynyl heteroaryl, C1-C6-alkyl cycloalkyl, C1-C6-alkyl heterocycloalkyl, C2-C6-alkenyl cycloalkyl, C2-C6-alkenyl heterocycloalkyl, C2-C6-alkynyl cycloalkyl, and C2-C6-alkynyl heterocycloalkyl;
R4 and R5 are independently from each other selected from the group consisting of H, hydroxy, fluoro, C1-C6 alkyl, carboxy, C1-C6 alkoxy, C1-C3 alkyl carboxy, C2-C3 alkenyl carboxy, and C2-C3 alkynyl carboxy, wherein at least one of R4 or R5 is neither a hydrogen nor a C1-C6 alkyl; to the mammal in an amount sufficient to treat or prevent the at least one disease.