US 7,538,109 B2
Quinoxalin-3-one derivatives as orexin receptor antagonists
Hamed Aissaoui, Pulversheim (France); Martine Clozel, Binningen (Switzerland); Thomas Weller, Binningen (Switzerland); Ralf Koberstein, Lörrach (Germany); and Thierry Sifferlen, Guewenheim (France)
Assigned to Actelion Pharmaceuticals Ltd, Allschwil (Switzerland)
Appl. No. 10/555,061
PCT Filed Apr. 26, 2004, PCT No. PCT/EP2004/004374
§ 371(c)(1), (2), (4) Date Oct. 28, 2005,
PCT Pub. No. WO2004/096780, PCT Pub. Date Nov. 11, 2004.
Claims priority of application No. 03/04491 (EP), filed on Apr. 28, 2003.
Prior Publication US 2007/0027157 A1, Feb. 01, 2007
Int. Cl. A01N 43/58 (2006.01); A61K 31/50 (2006.01); A01N 43/60 (2006.01); A61K 31/495 (2006.01); C07D 241/36 (2006.01)
U.S. Cl. 514—249  [544/354] 6 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Drawing
wherein:
X is O;
n is the integer 0;
m is the integer 0, 1, 2, or 3;
R1, R2, R3, R4 represent hydrogen;
R5 represents hydrogen, C1-C5 alkyl, —(CH2)m—CO2-C1-C5 alkyl, —(CH2)m—CONH2, —(CH2)m—CONH—C1-C5 alkyl, or —CON—(C1-C5 alkyl);
R6 represents hydrogen, or C1-C5 alkyl;
R7 represents hydrogen; C1-C5 alkyl; C2-C5 alkenyl; or mono-, di- or tri-substituted phenyl or phenyl-C1-C5 alkyl, whereby the substituents independently are C1-C5 alkyl, C1-C5 alkoxy, C2-C5 alkenyl or halogen; —(CH2)m—OH; —(CH2)m—O—C1-C5 alkyl; —(CH2)m—CO2H; —(CH2)m—CO2—C1-C5 alkyl; —(CH2)m—CONH2; —(CH2)m—CONH—C1-C5 alkyl; or —CON—(C1-C5 alkyl)2;
R8 represents unsubstituted phenyl; or mono-, di- or tri-substituted phenyl, whereby the substituents independently are C1-C5 alkyl, C1-C5 alkoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy or halogen; and
R9 represents mono-, di- or tri-substituted phenyl whereby the substituents independently are C1-C5 alkyl, C1-C5 alkoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy or halogen;
or an optically pure enantiomer, a mixture of enantiomers, a racemate, an optically pure diastereoisomer, a mixture of diastereoisomers, a diastereoisomeric racemate, a mixture of diastereoisomeric racemates, or a meso form, or a pharmaceutically acceptable salt thereof.