Tricyclic 5-HT.sub.3 receptor antagonists

US5202333A · kind A · utility

Assignee

• Syntex (U.S.A.) LLC · US

Inventors

• Jacob Berger · Los Altos Hills, US
• Robin Clark · Palo Alto, US
• Richard Eglen · Mountain View, US
• William L. Smith · Mahwah, US
• Klaus Weinhardt · San Francisco, US

Key dates

• Filing date: May 22, 1991
• Grant date: Apr 13, 1993
• Expiry date: May 22, 2011

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D471/08
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present invention is directed to 5-HT.sub.3 receptor antagonist compounds of formula I: ##STR1## in which the dashed line denotes an optional double bond; PA0 n is 1, 2 or 3; PA0 p is 0, 1, 2 or 3; PA0 q is 0, 1 or 2; PA0 each R.sup.1 is independently selected from halogen, hydroxy, lower alkoxy, lower alkyl, nitro, amino, amino carbonyl, (lower alkyl)amino, di(lower alkyl)amino, and (lower alkanoyl)amino; PA0 each R.sup.2 is lower alkyl; and PA0 R.sup.3 is a group selected from Formulae (a), (b), (c) and (d): ##STR2## in which u is 0 or 1; PA0 z is 1, 2 or 3; and PA0 R.sup.4 is C.sub.1-7 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl-C.sub.1-2 alkyl, or a group (CH.sub.2).sub.t R.sup.5 where t is 1 or 2 and R.sup.5 is thienyl, pyrrolyl, or furyl, each optionally further substituted by one or two substituents selected from C.sub.1-6 alkyl, C.sub.1-6 alkoxy, trifluoromethyl or halogen, or is phenyl optionally substituted by one or two substituents selected from C.sub.1-4 alkoxy, trifluoromethyl, halogen, nitro, carboxy, esterified carboxy, and C.sub.1-4 alkyl optionally substituted by hydroxy, C.sub.1-4 alkoxy, carboxy, esterified carboxy or in vivo hydrolyzable acyloxy; and …