Bicyclic heteroaryl derivatives

US10647721B2 · kind B2 · utility

Assignee

• Hoffmann-La Roche Inc. · US

Inventors

• Bjoern Bartels · Schopfheim, DE
• Roland Jakob-Roetne · Inzlingen, DE
• Anja Limberg · Penzberg, DE
• Werner Neidhart · Hagenthal-le-Bas, FR
• Hasane Ratni · Habsheim, FR
• Michael Reutlinger · Glückstadt, DE
• Greta Vastakaite · Basel, CH

Key dates

• Filing date: Oct 2, 2017
• Grant date: May 12, 2020
• Expiry date: Oct 2, 2037

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P25/28
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to a compound of formula (I), wherein R1 is hydrogen, lower alkyl, lower alkyl substituted by halogen, halogen, lower alkoxy or lower alkoxy substituted by halogen; and R1 may be different if n is 2 or 3; R2 is hydrogen, lower alkyl, lower alkyl substituted by halogen, halogen, CN, lower alkoxy or lower alkoxy substituted by halogen; X is CH or N; m is 1, 2 or 3; -( )m is —(CH2)m—; n is 1, 2 or 3; Ar is a five membered heteroaryl group, selected from formula (A), (B), (C), (D), (E) or (F), wherein R3 is hydrogen, methyl or chloro; R4 is hydrogen or methyl; R5 is F, Cl, CHF2 or CF3; or to pharmaceutically active acid addition salts thereof. The compounds may be used for the treatment of Alzheimer's disease, cerebral amyloid angiopathy, hereditary cerebral hemorrhage with amyloidosis, Dutch-type (HCHWA-D), multi-infarct dementia, dementia pugilistica or Down syndrome.