US 7,465,744 B2
Triazole compounds and the therapeutic use thereof
Dorothea Starck, Ludwigshafen (Germany); Hans-Jörg Treiber, Brühl (Germany); Thomas Zierke, Böhl-Iggelheim (Germany); Georg Kettschau, Berlin (Germany); Hervé Geneste, Neuhofen (Germany); Andreas Haupt, Schwetzingen (Germany); Liliane Unger, Ludwigshafen (Germany); Kai Blumbach, Steinen (Germany); Dietmar Schöbel, Mannheim (Germany); and Hans-Jurgen Teschendorf, Dudenhofen (Germany)
Assigned to Abbott GmbH & Co. KG, Wiesbaden (Germany)
Appl. No. 10/544,550
PCT Filed Feb. 05, 2004, PCT No. PCT/EP2004/001072
§ 371(c)(1), (2), (4) Date Jun. 07, 2006,
PCT Pub. No. WO2004/069830, PCT Pub. Date Aug. 19, 2004.
Claims priority of application No. 103 04 870 (DE), filed on Feb. 06, 2003.
Prior Publication US 2006/0241137 A1, Oct. 26, 2006
Int. Cl. A61K 31/41 (2006.01); C07D 401/02 (2006.01)
U.S. Cl. 514—307  [514/383; 546/148; 548/266.4] 16 Claims
 
1. A triazole compound of the formula I

OG Complex Work Unit Drawing
in which
A is C4-C10-alkylene or C3-C10-alkylene which includes at least one group Z which is selected from O, S, NR5, CONR5, COO and CO, where alkylene may also have a C3-C6-cycloalkylene group and/or a double or triple bond,
B is CH2 or CH2-CH2;
R1 is an aromatic radical which is selected from phenyl and a 5- or 6-membered heteroaromatic radical having 1, 2, 3 or 4 heteroatoms which are selected independently of one another from O, N and S, where the aromatic radical may have one or more substituents which are selected independently of one another from C1-C6-alkyl which is optionally substituted by OH, C1-C4-alkoxy, halogen or phenyl, or C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl which is optionally substituted by halogen or C1-C4-alkyl, or halogen, CN, OR6, COOR6, NR7R8, NO2, SR9, SO2R9, SO2NR7R8, COR10, and phenyl which is optionally substituted by one or two radicals which are selected independently of one another from C1-C4-alkyl, C1-C4-alkoxy, NR7R8, CN, CF3, CHF2 or halogen, where phenyl and the heteroaromatic radical may also be fused to a 5 or 6-membered, aromatic or nonaromatic carbocycle;
R2 is H, C1-C6-alkyl which is optionally substituted by OH, C1-C4-alkoxy, C1-C4-alkylthio, halogen or phenyl, or OH, C1-C6-alkoxy, OCF3, OCHF2, OSO2CF3, SH, C1-C6-alkylthio, C2-C6-alkenyl, C2-C6-alkynyl, halogen, CN or NO2;
R3 is C2-C10-alkyl, C1-C6-haloalkyl, C1-C10-alkyl which is substituted by C1-C4-alkoxy, C1-C4-alkylthio or phenyl which may in turn have one, two or three substituents selected from C1-C4-alkyl, C1-C4-haloalkyl, halogen, CN, OR6, COOR6, NR7R8, NO2, SR9, SO2R9, SO2NR7R8, COR10 and halogen, is C3-C6-cycloalkyl which is optionally substituted by halogen or C1-C4-alkyl, or is an aromatic radical which is selected from phenyl, naphthyl and a 5- or 6-membered heteroaromatic radical having 1, 2, or 3 heteroatoms which are selected independently of one another from O, N and S, where the aromatic radical may have one or two substituents which are selected independently of one another from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, halogen, CN, COOR6, NR7R8, NO2, SO2R9, SO2NR7R8, COR10, CF3, CHF2 or halogen, where R3 may also be methyl if R1 is an optionally substituted heteroaromatic radical;
R4 is H, C1-C6-alkyl which is optionally substituted by OH, C1-C4-alkoxy or phenyl, or C1-C6-haloalkyl, C3-C6-cycloalkyl which is optionally substituted by C1-C4-alkyl or halogen, or phenyl;
R5 is H, C1-C6-alkyl which is optionally substituted by OH, C1-C4-alkoxy or phenyl, or C1-C6-haloalkyl, phenyl or a COR11 group;
R6 to R10 are independently of one another H, C1-C6-alkyl which is optionally substituted by OH, C1-C4-alkoxy or phenyl, or C1-C6-haloalkyl or phenyl, where R8 may also be a COR11 group in which R11 has one of the meanings mentioned for R4;
R7 may also form together with R8 a 5- or 6-membered saturated or unsaturated carbocycle which may have a heteroatom selected from O, S, N and NR12 as ring member, where R12 is hydrogen or C1-C4-alkyl,
or a physiologically tolerated salt of this compound.