US 9,809,598 B2
Heterocyclyl-butanamide derivatives
Hans-Peter Buchstaller, Griesheim (DE); and Dieter Dorsch, Ober-Ramstadt (DE)
Assigned to MERCK PATENT GMBH, Darmstadt (DE)
Appl. No. 15/308,974
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Apr. 16, 2015, PCT No. PCT/EP2015/000793
§ 371(c)(1), (2) Date Nov. 4, 2016,
PCT Pub. No. WO2015/169421, PCT Pub. Date Nov. 12, 2015.
Claims priority of application No. 14001613 (EP), filed on May 7, 2014.
Prior Publication US 2017/0073347 A1, Mar. 16, 2017
Int. Cl. C07D 487/04 (2006.01); A61K 31/517 (2006.01); C07D 491/052 (2006.01); A61K 31/502 (2006.01); A61K 31/501 (2006.01); A61K 31/4985 (2006.01); A61K 31/454 (2006.01); C07D 413/06 (2006.01); C07D 401/14 (2006.01); C07D 491/04 (2006.01); C07D 495/04 (2006.01); C07D 413/04 (2006.01); C07D 401/06 (2006.01); C07D 471/04 (2006.01); A61K 31/519 (2006.01)
CPC C07D 487/04 (2013.01) [A61K 31/454 (2013.01); A61K 31/4985 (2013.01); A61K 31/501 (2013.01); A61K 31/502 (2013.01); A61K 31/517 (2013.01); A61K 31/519 (2013.01); C07D 401/06 (2013.01); C07D 401/14 (2013.01); C07D 413/04 (2013.01); C07D 413/06 (2013.01); C07D 471/04 (2013.01); C07D 491/04 (2013.01); C07D 491/052 (2013.01); C07D 495/04 (2013.01)] 20 Claims
 
1. A compound of formula I

OG Complex Work Unit Drawing
in which
W denotes

OG Complex Work Unit Drawing
wherein * indicates the point of attachment to the propylene moiety,
X denotes O, CO or is absent,
Y denotes Ar or Het1,
R1 denotes H, F, Cl, CN, CH3, CF3, CHF2, CH2OH or OCH3,
R2 denotes H or CH3,
Ar denotes phenyl, which is unsubstituted, or mono-, di- or trisubstituted by Hal, NO2, CN, A, OR3, S(O)mR3, N(R3)2, COA, COOR3, CON(R3)2, SO2N(R3)2, NR3COR3, NR3SO2A, NR3CON(R3)2 and/or Het2,
Het1 denotes furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidyl or pyridazinyl, each of which is unsubstituted or mono- or disubstituted by Hal, NO2, Ar1, CN, A, OR3, N(R3)2, CON(R3)2, Het2 and/or ═O,
Het2 denotes furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidyl or pyridazinyl, each of which is unsubstituted or mono- or disubstituted by Hal, NO2, Ar1, CN, A, OR3, N(R3)2, CON(R3)2 and/or ═O,
Ar1 denotes phenyl, which is unsubstituted, or mono-, di- or trisubstituted by Hal, NO2, CN, A, OR3, S(O)mR3, N(R3)2, COA, COOR3, CON(R3)2, NR3COR3 and/or NR3SO2A,
A denotes unbranched or branched alkyl with 1-8 C-Atoms, wherein one or two non-adjacent CH- and/or CH2-groups may each be replaced by N- or O-atoms and wherein 1-7 H-atoms may each be replaced by F, Cl or OH,
R3 denotes H or unbranched or branched alkyl with 1, 2, 3 or 4 C-Atoms,
Hal denotes F, Cl, Br or I,
m denotes 0, 1 or 2,
n denotes 1 or 2,
and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.