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US 5,707,990 AGranted
2-substituted amino and thio alkyl benzoxazine antimicrobial agents
AssigneeOrtho Pharmaceutical Corporation
InventorsRoger Frechette, Michael Beach
Life of this patent
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Abstract
The invention relates to benzoxazine and pyrido-oxazine antibacterial compounds of the general formula: ##STR1## wherein the moiety Q is a fused phenyl or fused pyridyl moiety and R is a substituted amine or substituted thio moiety as herein described, pharmaceutical compositions containing the compounds, methods for their production and their use in treating bacterial infections.
Claims13
A method of treating bacterial infections in mammals by administering to a mammal suffering from such infection a therapeutically effective amount of a compound selected from those of Formula 1:
- ##STR48## wherein the moiety Q is a fused phenyl moiety;
- Z.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, phenyl, hydroxy, amino, nitro, sulfonylamino or trifluoromethyl;
- Z.sub.2 is hydrogen or a halogen;
- X is hydrogen or oxygen;
- A is --C.sub.1 -C.sub.6 alkyl, --C.sub.1 -C.sub.6 alkylaryl or --C.sub.1 -C.sub.6 alkylheterocyclyl where in each case the A moiety is bonded to the nitrogen through the alkyl group;
- wherein aryl is biphenyl, naphthyl or phenyl;
- and heterocyclyl is a 5 or 6 membered saturated or unsaturated heterocyclic group containing 1-4 nitrogen atoms and/or an oxygen or a sulfur atom;
- wherein said aryl or heterocyclyl group is optionally substituted with (C.sub.1 -C.sub.6)alkyl, benzyl, oxybenzyl, phenoxy, hydroxy, alkoxy, halogen, dihalogen, nitro, amino, carboxyl, carbo(C.sub.1 -C.sub.4)alkoxy or methylsulfonylamino;
- R is a moiety selected from:
- ##STR49## wherein R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen, C.sub.1 -C.sub.6 alkyl, t-butoxycarbonyl, or carboxyethylpiperidine;
- R.sub.4 and R.sub.5 are independently t-butoxycarbonyl or hydrogen or R.sub.4 and R.sub.5 may be joined together to form an imidazoline, imidazolyl or pyrimidine ring;
- and the pharmaceutically acceptable salts, esters and pro-drug forms thereof.
9 more elements
A compound for treating bacterial infections in mammals selected from those of Formula 1:
- ##STR51## wherein the moiety Q is fused phenyl;
- Z.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, phenyl, hydroxy, amino, nitro, sulfonylamino or trifluoromethyl;
- Z.sub.2 is hydrogen or, where Z.sub.1 is a halogen, Z.sub.2 is also a halogen;
- X is oxygen;
- A is C.sub.1 -C.sub.5 alkyl, --CH.sub.2 phenyl, --CH.sub.2 thienyl, --CH.sub.2 pyridyl, --CH.sub.2 furyl, or -ethyl piperidine;
- wherein said phenyl, thienyl, pyridyl, furyl or piperidine moiety is optionally substituted with (C.sub.1 -C.sub.6)alkyl, benzyl, oxybenzyl, phenoxy, hydroxy, alkoxy, halogen, dihalogen, nitro, amino, carboxyl or carbomethoxy;
- R is the moiety:
- ##STR52## wherein R.sub.4 and R.sub.5 are independently t-butoxycarbonyl or hydrogen or R.sub.4 and R.sub.5 may be joined together to form an imidazoline, imidazolyl or pyrimidine ring;
- and the pharmaceutically acceptable salts, esters and pro-drug forms thereof.
6 more elements
A method of preparing a compound selected from those of Formula 1:
- ##STR53## wherein the moiety Q is a fused phenyl moiety;
- Z.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, phenyl, hydroxy, amino, nitro, sulfonylamino or trifluoromethyl;
- Z.sub.2 is hydrogen or, where Z.sub.1 is a halogen, Z.sub.2 is also a halogen;
- X is oxygen;
- A is C.sub.1 -C.sub.5 alkyl, --CH.sub.2 phenyl, --CH.sub.2 thienyl, --CH.sub.2 pyridyl, --CH.sub.2 furyl, or -ethyl piperidine;
- wherein said phenyl, thienyl, pyridyl, furyl or piperidine moiety is optionally substituted with (C.sub.1 -C.sub.6)alkyl, benzyl, oxybenzyl, phenoxy, hydroxy, alkoxy, halogen, dihalogen, nitro, amino, carboxyl or carbomethoxy;
- R' is a moiety;
- ##STR54## wherein R.sub.4 and R.sub.5 are independently t-butoxycarbonyl or hydrogen or R.sub.4 and R.sub.5 may be joined together to form an imidazoline, imidazolyl or pyrimidine ring;
- and
- the pharmaceutically acceptable salts, esters and pro-drug forms thereof, which comprises reacting a compound of the formula:
- ##STR55## with a halogenating agent to form a halogenated compound of the formula:
- ##STR56## wherein the moiety Y is a halogen, in a suitable solvent followed by reacting said halogenated compound with compound of the formula HR' wherein R' is as hereinbefore defined and recovering the compound of formula 1.
9 more elements
Dependencies are inferred from the claim text.