Benzoxazinedione derivatives, method of producing them and uses thereof

US6013647A · kind A · utility

Assignee

• Gruenenthal GmbH · DE

Inventors

• Lothar Heinisch · Jena, DE
• Steffen Wittmann · Jena, DE
• Ute Moellmann · Jena, DE
• Rolf Reissbrodt · Wernigerode, DE

Key dates

• Filing date: Mar 5, 1998
• Grant date: Jan 11, 2000
• Expiry date: Mar 5, 2018

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02A50/30
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

This invention relates to new benzoxazinedione derivatives corresponding to the formula I: ##STR1## wherein R.sup.1 =H or carboxyalkyl, R.sup.2 =H, alkyl or phenyl, and R.sup.3 represents different acid groups derived from amino acids, dipeptides and hydrazones or conjugates thereof with active ingredients, e.g. antibiotics. The compounds may be present as free acids, in the form of their salts or as readily cleavable esters. The compounds according to the invention constitute heterocyclically protected catechol derivatives and are effective as siderophores against gram-negative bacterial strains, particularly against Pseudomonads and strains of E. coli and Salmonella. In the form of their conjugates with active ingredients, e.g. antibiotics (as "siderophore-antibiotic conjugates"), they can transport the latter into bacterial cells and can improve or extend the antibacterial effect thereof, sometimes even in relation to bacterial strains which are resistant to other .beta.-lactams. In addition, said compounds, as potential prodrug forms for iron chelating agents, are suitable for use against diseases which are caused by a disorder of the iron metabolism. The invention can be emplo…