ESTERS OF 2-QUINOXALINECARBOXYLIC ACID DI N-OXIDE

摘要

1377306 Esters of 3-methyl-quinoxaline-2- carboxylic acid-di-N-oxides PFIZER Inc 31 Jan 1972 [20 April 1971] 4505/72 Addition to 1330151 Heading C2C Novel esters of 3-methyl-2-quinoxaline carboxylic acid, 1,4-dioxide of general Formula I: in which X is a 6- or 7-position substituent selected from hydrogen, chloro, bromo, fluoro, methyl, methoxy or trifluoromethyl A is alkylene of 2-5 C atoms and Z is acyloxy of formula O 2 CR where R is C 4-10 alkyl, C 1-4 alkoxy, C 1-4 alkylamino, C 2-8 carboxyalkyl or substituted C 1-4 alkyl (in which the substituent is chlorine, bromine or di-C 1-3 alkyl-amino) and where appropriate acid addition salts, pharmaceutically acceptable basic salts and C 1-3 alkyl quaternary salts with a pharmaceutically acceptable anion are prepared by (1) reacting a benzofuran of general Formula II: with either CH 3 -CO-CH 2 -O-O-A-Z or CH 3 -CH 2 -CO-CO-O-A-Z in the presence of a base or (2) reacting an ester 2-quinoxaline carboxylic acid, 1,4-di-N-oxide of general Formula III: in which M is alkyl or phenyl or a 2-cyanoquinoxaline-di-N-oxide of general Formula IV: with an alkanol of general Formula HO-A-Z Compounds of general Formula I, in which Z is carboxyacyloxy or acyloxy, may be prepared from compounds III in which M is 2-hydroxyethyl, by reaction with the appropriate anhydride or acid chloride. Compounds of general Formula I in which Z is alkyl carbamoyl may be prepared from compounds III in which M is 2- hydroxyethyl by reaction with the appropriate isocyanate. Compounds of general Formula I in which Z is dialkylaminoacyloxy are prepared by reaction of a secondary amine with a compound of general Formula I in which Z is alkyl substituted by chlorine or bromine. Preferred compounds are 3-methyl-2-quinoxaline carboxylic acid, 2-(3-carboxypropionyloxy)ethyl ester, di - N - oxide; 3 - methyl - 2 - quinoxaline carboxylic acid, 2 - (4 - carboxybutyryloxy)ethyl ester, di - N - oxide; 3 - methyl - 2 - quinoxaline carboxylic acid, 2 - (octanoyloxy)ethyl ester, di - N- oxide; 3 - methyl 2 - quinoxaline carboxylic acid, 2 - [(ethoxycarbonyl)oxy]ethyl ester, di - N - oxide. Compounds of formula are anti-microbials and may be used in water treatment, paint and wood preservation, as a disinfectant and as an antibiotic. They form with a suitable carrier a pharmaceutical composition which may be administered orally, parenterally or topically. Compounds of Formula I also may be added to an animal feed for promoting growth and improving feed efficiency.