2-Hydroxymethyl-quinoxaline-1,4-dioxide derivatives, a process f

Details 2-Hydroxymethyl-quinoxaline-1,4-dioxide derivatives, a process f 2-Hydroxymethyl-quinoxaline-1,4-dioxide derivatives, a process f

1984-03-27

1985-04-16

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

544295, C07D24152, C07D40312, C07D40112, A61K 31495

Patent

active

045117179

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The invention relates to new 2-hydroxymethyl-quinoxaline-1,4-dioxide derivatives, a process for the preparation thereof and compositions--particularly feed additives, fodder concentrates and animal feeds--containing the same.


BACKGROUND OF THE INVENTION

It is known that certain quinoxaline-1,4-dioxide derivatives possess antimicrobial and weight-gain increasing properties. Such compounds are described in U.S. Pat. No. 3,371,900 and British patent No. 1,479,239.


DESCRIPTION OF THE INVENTION

According to the present invention there are provided new 2-hydroxymethyl-quinoxaline-1,4-dioxide derivatives of the formula (I) ##STR2## wherein A represents an amino group, or a group of the formula --NH--COOR.sub.1, wherein R.sub.1 stands for a C.sub.2-4 alkyl group, or a group of the formula --NH--CX--NH.sub.2, wherein X denotes an oxygen or sulfur atom, or a group of the formula --NH--C(.dbd.NH)--NH.sub.2, or a group of the formula --NH--R.sub.2, wherein R.sub.2 represents a C.sub.1-6 alkyl, a phenyl, a benzyl, a hydroxyl or a hydroxy-(C.sub.2-4 alkyl) group, or a group of the formula --NH--CO--R.sub.3, wherein R.sub.3 stands for a C.sub.1-20 alkyl group or a phenyl group optionally substituted by one, two or three identical or different substituents selected from the group consisting of nitro, hydroxyl, amino, C.sub.1-3 alkoxy and halogen; a naphthyl group optionally substituted by a hydroxyl group, a phenyl-(C.sub.1-3 alkyl) group, a pyridyl, a piperidyl, a pyrazinyl, a pyrimidyl, a 1,2,4-triazinyl, a furyl, a nitrofuryl or an .alpha.,.alpha.-diphenyl-.alpha.-hydroxymethyl group.
The term "alkyl group" used in the specification and claims covers straight-chained and branched saturated aliphatic hydrocarbyl groups, such as methyl, ethyl, n-propyl, isopropyl, and n-butyl, isobutyl, tert.-butyl. The term "C.sub.1-3 alkoxy group" relates to straight or branched lower alkylether groups, such as methoxy, ethoxy, n-propoxy or isopropoxy. The term "halogen atom" encompasses all the four halogen atoms, ie. the fluorine, chlorine, bromine and iodine. Preferred representatives of the "hydroxy-(C.sub.2-4 alkyl) group" are the hydroxyethyl, hydroxypropyl, hydroxyisopropyl and hydroxybutyl groups. The "phenyl-(C.sub.1-3 alkyl) group" may represent benzyl, .alpha.-phenylethyl, .beta.-phenylethyl, .beta.,.beta.-diphenylethyl.
According to a further feature of the invention there is provided a process for the preparation of the compounds of the formula (I), characterized by
a. reacting a quinoxaline-1,4-dioxide derivative of the formula (II) ##STR3## wherein Q represents an oxygen atom or two C.sub.1-4 alkoxy groups, with a compound of the formula (III)
b. to prepare a compound of the formula (I), in which A is a group of the formula --NH--COOR.sub.1 or --NH--CO--R.sub.3, wherein R.sub.1 and R.sub.3 have the same meanings as above, reacting 2-(.alpha.-hydrazino-.alpha.-hydroxymethyl)-quinoxaline-1,4-dioxide of the formula (IV) ##STR4## with a carboxylic acid derivative of the formula (V) defined above, or R.sub.4 represents a group of the formula --OR.sub.1, wherein R.sub.1 is as defined above, and X stands for a leaving group, preferably chlorine.
According to variant a. of the process according to the invention a compound of the formula (II) is reacted with a compound of the formula (III). The reaction is generally performed below 30.degree. C., preferably at about 10.degree. C. to 30.degree. C., in the presence of water or an indifferent organic solvent, such as dimethyl-acetamide, dimethyl-formamide, etc. The reaction is preferably carried out in the presence of a catalyst. As catalyst, preferably mineral acids, such as hydrochloric, sulfuric or phosphoric acid; organic acids, such as p-toluenesulfonic acid; organic bases, such as triethylamine, piperidine, pyrrolidine, morpholine, etc. are used.
When using 2-formyl-quinoxaline-1,4-dioxide-dialkyl-acetal, e.g. dimethyl-acetal as the starting substance of the formula (II), one can also perform the reaction by boiling it in acidic medium for a short

REFERENCES:
patent: 3433871 (1964-03-01), Johnston
patent: 3649363 (1972-02-01), Kim
patent: 3926992 (1975-12-01), McFarland
patent: 4100284 (1978-07-01), Cue
patent: 4221791 (1980-09-01), Young et al.

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