US 9,808,456 B2
Piperazine thiazole derivatives useful in the treatment of tauopathies such as Alzheimer's disease
Gerard Griffioen, Linden (BE); Giuseppe Cecere, Basel (CH); Matthias Nettekoven, Grenzach-Wyhlen (DE); Katrien Princen, Heverlee (BE); Hasane Ratni, Habsheim (FR); Mark Rogers-Evans, Bottmingen (CH); and Walter Vifian, Gelterkinden (CH)
Assigned to REMYND NV, Leuven (BE)
Filed by REMYND NV, Leuven (BE)
Filed on Oct. 15, 2015, as Appl. No. 14/884,689.
Application 14/884,689 is a continuation of application No. 14/238,905, granted, now 9,187,440, previously published as PCT/EP2012/066136, filed on Aug. 17, 2012.
Claims priority of application No. 11177742 (EP), filed on Aug. 17, 2011.
Prior Publication US 2016/0101102 A1, Apr. 14, 2016
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/496 (2006.01); C07D 417/04 (2006.01); C07D 417/12 (2006.01); C07D 285/08 (2006.01); C07D 417/14 (2006.01)
CPC A61K 31/496 (2013.01) [C07D 285/08 (2013.01); C07D 417/04 (2013.01); C07D 417/12 (2013.01); C07D 417/14 (2013.01)] 30 Claims
 
1. A method for treating a patient suffering from Alzheimer's disease, which method comprises administering an effective amount of a compound of formula IA or a pharmaceutically active salt thereof, a stereoisomeric form, including an individual diastereoisomer or enantiomer of the compound of formula IA as well as a racemic or non-racemic mixture thereof; to the patient, thereby treating the disease;

OG Complex Work Unit Drawing
wherein
G1 is lower alkyl; lower alkyl substituted by one or more halogens; cycloalkyl; tetrahydropyran-4-yl; phenethyl; phenethyl substituted by one or more halogens; phenoxymethyl; phenoxymethyl substituted by one or more halogens; benzyloxy-ethyl; benzyloxy-ethyl substituted by one or more halogens; or is —NR2R3;
R2 is hydrogen or lower alkyl;
R3 is lower alkyl, tetrahydropyran-4-yl, —CH2-cycloalkyl or cycloalkyl optionally substituted by lower alkyl substituted by one or more halogens; or R2 and R3 form together with the N-atom to which they are attached a heterocycloalkyl group with 4 or 5 carbon atoms, which is optionally substituted by one or more substituents selected from halogen or lower alkyl substituted by one or more halogens;
X is —CH2— or —(CH2)2—;
Ar is phenyl or pyridinyl;
R4 is halogen; lower alkyl; lower alkyl substituted by one or more halogens; or lower alkoxy;
n is 1 or 2;
with the proviso that said compound is not:
5-(4-(3-fluorobenzyl)piperazin-1-yl)-3-methyl-1,2,4-thiadiazole or
3-isopropyl-5-(4-(3-(trifluoromethyl)benzyl)piperazin-1-yl)-1,2,4-thiadiazole.