N-substituted 4-((4′-aminobenzoyl)-oxymethyl)-piperidines having gastric prokinetic properties

US6509339B2 · kind B2 · utility

Assignee

• Janssen Pharmaceutica NA · BE

Inventors

• Jean-Paul René Marie André Bosmans · Rijkevorsel, BE
• Christopher John Love · Deurne, BE
• Marc Gustaaf Celine Verdonck · Lille, BE
• Joannes Adrianus Jacobus Schuurkes · Beerse, BE

Key dates

• Filing date: Aug 20, 2001
• Grant date: Jan 21, 2003
• Expiry date: Aug 20, 2021

Classification

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

Abstract

This invention concerns the compounds of formula the N-oxide forms, the pharmaceutically acceptable acid addition salts and the stereochemically isomeric forms thereof, wherein R1 is C1-6alkyloxy, C2-6alkenyloxy or C2-6alkynyloxy; R2 is hydrogen or C1-6alkyloxy, or when taken together R1 and R2 may form a bivalent radical of formula wherein in said bivalent radicals one or two hydrogen atoms may be substituted with C1-6alkyl, R3 is hydrogen or halo; L is C3-6cycloalkyl, C5-6cycloalkanone, C2-6alkenyl optionally substituted with aryl, or L is a radical of formula -Alk-R4, -Alk-NR5R6, 1-R6-4-piperidinyl, Alk-X—R7, -Alk-Y—C(═O)—R9, or -Alk-Y—C(═O)—NR11R12 wherein each Alk is C1-12alkanediyl; R4 is hydrogen, C1-6alkylsulfonylamino, C3-6cycloalkyl, C5-6cycloalkanone, Ar-, di(Ar)methyl, Ar-oxy- or Het1; R5 is hydrogen or C1-6alkyl; R6 is Het2; R7 is hydrogen, C1-6alkyl, hydroxyC1-6alkyl, C3-6cycloalkyl, Ar or Het2; X is O, S, SO2 or NR8; said R8 being hydrogen, C1-6alkyl or Ar; R9 is hydrogen, C1-6alkyl, C3-6cycloalkyl, Ar, ArC1-6alkyl, di(Ar)methyl, C1-6alkyloxy or hydroxy; Y is NR10 or a direct bond; said R10 being hydrogen, C1-6alkyl or Ar; R11 …