Esters of 3-(3-substituted-amino-2-hydroxypropoxy)-4-substituted-1,2,5-thiadiazole derivatives

US4508725A · kind A · utility

Assignee

• American Hospital Supply Corp. · US

Inventors

• William L. Matier · Libertyville, US
• Paul W. Erhardt · Toledo, US
• Ghanshyam Patil · McKeesport, US

Key dates

• Filing date: Dec 22, 1982
• Grant date: Apr 2, 1985
• Expiry date: Dec 22, 2002

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D285/10
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Novel compounds are disclosed having the formula ##STR1## wherein R is lower alkyl, lower cycloalkyl, lower haloalkyl, lower alkylcarboxymethyl, arylcarboxymethyl, lower alkenyl, lower alkynyl, aryl having from 6 to about 10 carbon atoms, or aralkyl; R.sub.1 is lower alkyl, lower hydroxyalkyl, lower alkenyl, lower alkynyl, aralkyl, or --WB; where W is alkylene containing from 1 to about 10 carbon atoms; and B is --NR.sub.2 COR.sub.3, --NR.sub.2 CONR.sub.3 R.sub.4, --NR.sub.2 SO.sub.2 R.sub.3, --NR.sub.2 SO.sub.2 NR.sub.3 R.sub.4, or --NR.sub.2 COOR.sub.5, where R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, alkoxyaryl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.3 and R.sub.5 are not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.3 or --NR.sub.2 COOR.sub.5, or R.sub.3 and R.sub.4 may together with N form a 5- to 7-membered heterocyclic group; A is a direct bond, lower alkylene, or lower alkene having from 1 to about 10 carbon atoms; and the pharmaceutically acceptable salts thereof. These compounds are useful as .beta.-adrenergic blocking agents and for the treatment of glaucoma.