Phenylethylamines and condensed rings variants as prodrugs of catecholamines, and their use

US6998405B2 · kind B2 · utility

Assignee

• H. LUNDBECK A/S · DK

Inventors

• Hakan V. Wikstrom · Mölndal, SE
• Durk Dijkstra · Bedum, NL
• Bastiaan Johan Venhuis · Groningen, NL

Key dates

• Filing date: Dec 18, 2003
• Grant date: Feb 14, 2006
• Expiry date: Dec 18, 2023

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2603/26
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Compounds of the general formula I wherein rings B, C, D and E may be present or not and, when present, are combined with A as A+C, A+E, A+B+C, A+B+D, A+B+E, A+C+E, A+B+C+D or A+B+C+D+E, rings B, C and E being aliphatic whereas ring D may be aliphatic or aromatic/heteroaromatic, and wherein X is —(CH2)m—, in which m is an integer 1–3, to form a ring E or, when E is absent, a group R1 bound to the nitrogen atom, wherein R1 is selected from the group consisting of a hydrogen atom, alkyl or haloalkyl groups of 1 to 3 carbon atoms, cycloalkyl(alkyl) groups of 3 to 5 carbon atoms (i.e. including cyclopropyl, cyclopropylmethyl, cyclobutyl and cyclobutylmethyl) and wherein Y is —(CH2)n—, in which n is an integer 1–3, to form a ring C or when C is absent, a group R2 bound to the nitrogen atom, wherein R2 is selected from the group consisting of a hydrogen atom, alkyl or haloalkyl groups of 1 to 7 carbon atoms, cycloalkyl(alkyl) groups of 3 to 7 carbon atoms, alkenyl or alkylnyl groups of 3 to 6 carbon atoms, arylalkyl, heteroarylalkyl having 1 to 3 carbon atoms in the alkyl moiety, whilst the aryl/heteroaryl nucleus may be substituted, provided that when rings B, C, D and E are absent NR1R…