Bicyclic heterocycles, pharmaceutical compositions containing them, their use, and processes for preparing them

US6653305B2 · kind B2 · utility

Assignee

• BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG · DE

Inventors

• Frank Himmelsbach · Mittelbiberach, DE
• Elke Langkopf · Biberach an der Riß, DE
• Birgit Jung · Laupheim, DE
• Stefan Blech · Warthausen, DE
• Flavio Solca · Wien, AT

Key dates

• Filing date: Aug 15, 2001
• Grant date: Nov 25, 2003
• Expiry date: Aug 15, 2021

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D413/14
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

A compound of formula (I) wherein:Ra is a benzyl or 1-phenylethyl group or a phenyl group substituted by the groups R1 and R2, wherein:R1 is a hydrogen, fluorine, chlorine, or bromine atom, or a methyl, trifluoromethyl, cyano, or ethynyl group, andR2 is a hydrogen or fluorine atom;Rb is an R3O—CO—CH2—N—CH2—CH2—OH group optionally substituted at the methylene groups by 1 or 2 methyl or ethyl groups, wherein R3 is a hydrogen atom or a C1-4-alkyl group, a 2-oxomorpholin-4-yl group optionally substituted by 1 or 2 methyl or ethyl groups, or a N-[(1,3-dioxolan-2-yl)methyl]methylamino group;Rc is a hydrogen atom, or a methoxy, ethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, tetrahydrofuran-3-yloxy, tetrahydropyran-3-yloxy, tetrahydropyran-4-yloxy, tetrahydrofuranylmethoxy, or tetrahydropyranylmethoxy group; andn is 1, 2, or 3, the tautomers, stereoisomers, and salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases which have valuable pharmacological properties, their use in the t…