Barbituric acid derivatives, processes for their production and pharmaceutical agents containing these compounds

US6472396B1 · kind B1 · utility

Assignee

• Roche Diagnostics GMBH · DE

Inventors

• Elmar Bosies · Weinheim, DE
• Angelika Esswein · Büttelborn, DE
• Frank Grams · Mannheim, DE
• Hans-Willi Krell · Penzberg, DE
• Ernesto Menta · Parma, IT

Key dates

• Filing date: Jun 16, 2000
• Grant date: Oct 29, 2002
• Expiry date: Jun 16, 2020

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D239/62
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Compounds of formula I, useful as matrix metalloprotease inhibitors, whereinX, Y and Z are each oxygen;R1 is selected from the group consisting of (a) n-octyl, (b) n-decyl, (c) biphenyl and (d) (4-phenoxy)phenyl, wherein the terminal monocycle for moieties (c)-(d) is unsubstituted or substituted by a substituent selected from the group consisting of —NH2, —NO2, —SO2NH2, —SO2CH3, acetyl, hydroxy, methoxy, ethoxy, cyano and halogen;R2 and R3 are each hydrogen; andR4 and R5, together with the nitrogen atom to which they are bound, form a piperazinyl or piperidyl ring, wherein the piperazinyl ring is substituted in the 4-position with a substituent selected from the group consisting of (a) a 6-membered aromatic monocycle having 0, 1 or 2 nitrogen atoms and the remainder of the atoms in the monocycle being carbon and (b) hydroxy-C1-C6 alkyl, wherein the monocycle is unsubstituted or substituted by a substituent selected from the group consisting of halogen, —NH2, —NO2, —SO2NH2, —SO2CH3, acetyl and cyano.