Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones, their preparation and their use in medicaments

US6596742B1 · kind B1 · utility

Assignee

• Aventis Pharma Deutschland GmbH · DE

Inventors

• Stefan Petry · Kelkheim, DE
• Karl Schoenafinger · Alzenau, DE
• Guenter Mueller · Pocking, DE
• Karl-Heinz Baringhaus · Blieskastel, DE

Key dates

• Filing date: Sep 5, 2000
• Grant date: Jul 22, 2003
• Expiry date: Sep 5, 2020

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P43/00
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones of the formula 1 in any optically isomeric form, and their physiologically acceptable salts, where R1 is C1-C6-alkyl, C3-C9-cycloalkyl, both of which may be unsubstituted or substituted, and R2 and R3 independently of one another are hydrogen, C6-C10-aryl, C3-C8-cycloalkyl, C6-C10-aryloxymethyl, O-benzyl, O—C6-C10-aryl, O—C3-C8-cycloalkyl, O—C1-C6-alkyl, SO2—NH—C1-C6-alkyl, SO2—NH-(2,2,6,6-tetramethylpiperidin-4-yl), SO2—NH—C3-C8-cycloalkyl, SO2—N(C1-C6-alkyl)2 or COX, where X is O—C1-C6-alkyl, NH—C1-C6-alkyl, NH—C3-C8-cycloalkyl or N(C1-C6-alkyl)2, with the proviso that the substitutents R2 and R3 may in some instances be unsubstituted or substituted and are not both simultaneously hydrogen. A process for their preparation, and their inhibitory effect on the hormone-sensitive lipase, HSL.