2-oxy-4H-3,1-benzoxazin-4-ones and related compounds and pharmaceutical use

US4745116A · kind A · utility

Assignee

• Syntex (U.S.A.) LLC · US

Inventors

• Alexander Krantz · San Francisco, US
• Robin Spencer · Mississauga, CA
• Tim Fat Tam · Vaughan, CA
• Teng J. Liak · Mississauga, CA

Key dates

• Filing date: Dec 23, 1986
• Grant date: May 17, 1988
• Expiry date: Dec 23, 2006

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07F9/65335
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

2-Oxy-4H-3,1-benzoxazin-4-ones, useful as serine protease inhibitors, represented by the formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein: PA0 a is an integer of 1 to 4; PA0 A is a bond, or alkylene having one to eight carbon atoms; PA0 R is hydrogen, phenyl, imidazolyl or cycloalkyl having three to six carbon atoms, wherein the phenyl, imidazolyl or cycloalkyl ring is optionally substituted with 1 to 3 substituents independently selected from the group consisting of lower alkyl having one to four carbon atoms, lower alkoxy having one to four carbon atoms, --N(R.sup.1).sub.2, --NO.sub.2, halo or lower alkylthio having one to four carbon atoms, and, PA0 each R' is independently selected from the group consisting of hydroxy, benzyloxy, lower alkyl having one to six atoms, lower alkenyl having two to six carbon atoms, lower alkoxy having one to six carbon atoms, lower alkylthio or halo-lower alkyl having one to six carbon atoms, halo, --NO.sub.2, --N(R.sup.1).sub.2, --NR.sup.1 CO.sub.2 R.sup.2, --NR.sup.1 COR.sup.2, and --NR.sup.1 C(O)N(R.sup.1).sub.2, PA0 in which PA1 each R.sup.1 is independently hydrogen or lower alkyl having one to four ca…