Lipid-A analogs: monosaccharide and dissaccharide compounds for inhibiting binding of lipid A receptors to lipid A receptors

US5593969A · kind A · utility

Assignee

• IGEN Co., LTD · US

Inventors

• Balreddy Kamireddy · Rockville, US
• Michael J. Darsley · Rockville, US
• David M. Simpson · Murfreesboro, US
• Richard J. Massey · Rockville, US

Key dates

• Filing date: Sep 17, 1993
• Grant date: Jan 14, 1997
• Expiry date: Sep 17, 2013

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61K38/00
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

A compound of the formula: ##STR1## wherein: each of R.sub.1, R.sub.1 ', R.sub.2 and R.sub.2 ' independent of each other is a substituted or unsubstituted, branched or linear C.sub.1-12 alkyl, alkene or alkyne group, R.sub.3 is OH, OCH.sub.3, CH.sub.2 COOH or ##STR2## wherein each of R.sub.2" and R.sub.2 '41 independent of each other is a substituted or unsubstituted, branched or linear C.sub.1-12 alkyl, alkene or alkyne group and: PA1 A=NH.sub.2, X=P(OH), Y=Z=C, B=OCH.sub.3, or PA1 A=OH, X=P(OH), X=Z=C, B (if present)=OCH.sub.3, or PA1 A=OCO(CH.sub.2).sub.n NH.sub.2, X=P(OH), Y=Z=C, B=OCH.sub.3, wherein n=1-10, or PA1 A=OH, X=P(OH), Y=Z=C, B=O(CH.sub.2).sub.n CO.sub.2 H, wherein n=1-10, or PA1 A=OH, X=P(OH), Y=Z=C, B=(CH.sub.2).sub.n CO.sub.2 H, wherein n=1-10, or PA1 A=NH.sub.2, X=Z=C, Y=P(OH), B=OCH.sub.3, or PA1 A=OH, X=Z=C, Y=P(OH), B (if present)=OCH.sub.3, or PA1 A=OCO(CH.sub.2).sub.n NH.sub.2, X=Z=C, Y=P(OH), B=OCH.sub.3, wherein n=1-10, or PA1 A=OH, X=Z=C, Y=P(OH), B=O(CH.sub.2).sub.n CO.sub.2 H, wherein n=1-10, or PA1 A=OH, X=Z=C, Y=P(OH), B=(CH.sub.2).sub.n CO.sub.2 H, wherein n=1-11, or PA1 A=NH.sub.2, X=Y=C, Z=P(OH), B=OCH.sub.3, or PA1 A=OH, X=Y=C, Z=P(OH), B (if pres…