US 7,320,979 B2
N-[(piperazinyl)hetaryl]arylsulfonamide compounds
Wilfried M. Braje, Rintein (Germany); Andreas Haupt, Schwetzingen (Germany); Wilfried Lubisch, Heidelberg (Germany); Roland Grandel, Dossenheim (Germany); Karla Drescher, Dossenheim (Germany); Hervé Geneste, Neuhofen (Germany); Liliane Unger, Ludwigshafen (Germany); Daryl R. Sauer, Trevor, Wis. (US); and Sean C. Turner, Mannheim (Germany)
Assigned to Abbott GmbH & Co. KG., Wiesbaden (Germany)
Filed on Apr. 13, 2004, as Appl. No. 10/823,317.
Claims priority of provisional application 60/462782, filed on Apr. 14, 2003.
Prior Publication US 2006/0160809 A1, Jul. 20, 2006
Int. Cl. A61K 31/496 (2006.01); A61K 31/506 (2006.01); C07D 213/72 (2006.01); C07D 213/74 (2006.01); C07D 239/48 (2006.01)
U.S. Cl. 514—252.14  [514/253.01; 544/295; 544/360] 22 Claims
 
1. An N-[(piperazinyl)hetaryl]arylsulfonamide compound of the general formula I

OG Complex Work Unit Drawing
in which
R is oxygen, a group N—R3 or a group CR3aR3b;
Q is a bivalent, 6-membered heteroaromatic radical selected from pyridindiyl and pyrimidindiyl, and which optionally carries one or two substituents Ra which is/are selected, independently of each other, from halogen, CN, NO2, CO2R4, COR5, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, NH2, NHR6, NR6R7 and C1-C4-haloalkoxy;
Ar is phenyl or a 6-membered heteroaromatic radical selected from pyridinyl and pyrimidinyl, and which carries one or two substituents Rb, which is/are selected from halogen, NO2, CN, CO2R4, COR5, NHR6, NR6R7, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl and C1-C4-haloalkyl, with it also being possible for two radicals Rb which are bonded to adjacent C atoms of Ar to be together C3-C4-alkylene;
n 0, 1 or 2;
R1 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C4-alkenyl or C3-C4-alkynyl;
R2 is C1-C4-alkyl or, together with R1, is C2-C5-alkylene or, in the case of n=2, the two radicals R2 can together be C1-C4-alkylene;
R3 is hydrogen or C1-C4-alkyl;
R3a, R3b are, independently of each other, hydrogen or C1-C4-alkyl;
R4 is C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl C3-C6-cycloalkyl, C3 -C6-cycloalkyl-C1-C4-alkyl, phenyl or benzyl; and
R5 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl or benzyl;
R6, R7 are each independently selected from C1-C4-alkyl, C1-C4-haloalkyl or together with the nitrogen to which they are bound form a saturated 3-, 4-, 5- or 6-membered heterocycle, which additionally may comprise an oxygen atom or an additional nitrogen atom as a ring member and which may carry 1, 2, 3 or 4 C1-C4 alkyl groups;
the N-oxides thereof and the physiologically tolerated acid addition salts of these compounds;
with the exception of the compounds: 4-methyl-N-[6-(4-methylpiperazin-1-yl)pyridin-3-yl) benzenesulfonamide and 4-chloro-N-[6-(4-methylpiperazin-1-yl)pyridin-3-yl) benzenesulfonamide.