Piperazine thiazole derivatives useful in the treatment of tauopathies such as Alzheimer's disease

US9808456B2 · kind B2 · utility

Assignee

• ReMYND N.V. · BE

Inventors

• Gerard Griffioen · Linden, BE
• Giuseppe Cecere · Basel, CH
• Matthias Nettekoven · Weil am Rhein, DE
• Katrien Princen · Heverlee, BE
• Hasane Ratni · Habsheim, FR
• Mark Rogers-Evans · Bottmingen, CH
• Walter Vifian · Gelterkinden, CH

Key dates

• Filing date: Oct 15, 2015
• Grant date: Nov 7, 2017
• Expiry date: Oct 15, 2035

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D417/14
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present invention relates to a compound of formula (IA), 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; benzyloxyethyl; 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; or to a pharmaceutically active salt thereof, to a stereoisomeric form, including an individual diastereoisomer or enantiomer of the compound of formula (IA) as well as to a racemic or non-racemic mixture thereof. The present inve…