Patent GB-1121104-A (GB)
Title: Quinoxaline derivatives
IPC: C07D241/52
Filed: 1965-08-12
Abstract: Novel quinoxaline di-N-oxides of the general formula <FORM:1121104/C2/1> where R1 is hydrogen, -CHO, C1- 10 alkyl, a -hydroxy lower alkyl wherein the alkyl group contains at least 2 carbon atoms, a -lower alkanoyloxy lower alkyl wherein the alkyl group contains at least 2 carbon atoms, a -lower alkanoyloxy methyl wherein the alkanoyloxy group contains at least 3 carbon atoms or a -lower alkoxy lower alkyl wherein the alkyl group contains at least 2 carbon atoms; R2 is C1- 10 alkyl with the proviso that when R1 is H, R2 is at least C3 alkyl, and when R1 is alkyl, R2 is at least C6 alkyl, or R2 is -CHO, a -lower alkanoyloxy lower alkyl, a -hydroxy lower alkyl, a -lower alkoxy lower alkyl or a -lower alkanoyl providing that when R1 is H or Me, R2 is alkanoyl of at least 2 carbon atoms; and X1, X2, X3 and X4 are each hydrogen or lower alkyl; wherein said lower alkyl, lower alkanoyloxy, lower alkanoyl and lower alkoxy groups contain 1 to 6 carbon atoms; with the proviso that when R1 is -CHO and X1 to X4 are each hydrogen, R2 is other than H or Me, and when at least one of X1 to X4 is lower alkyl, R1 and R2 are as defined above, are prepared by reacting the corresponding N,N1 - unsubstituted quinoxaline compound with a percarboxylic acid.  The compounds are useful in the control of chromic respiratory disease in poultry.  2 - Lower alkanoyl - 3 - alkyl - quinoxaline di-N-oxides are prepared by selenium dioxide oxidation of the corresponding 2,3-dialkyl compounds.  2 - (a  - Hydroxyethyl) - 3 - (lower alkyl)-quinoxaline is prepared by reacting 2-formyl-3-lower alkyl-quinoxaline with methyl magnesium bromide.  2 - (a  - Acetoxy - lower alkyl) - 3 - lower alkyl quinoxaline is prepared by treating 2,3-di-lower alkyl quinoxaline with m-chloroperbenzoic acid and reacting the resulting 2,3-di-lower alkyl-quinoxaline mono-N-oxide with acetic anhydride.  2 - (a  - Hydroxy lower alkyl) - 3 - lower alkyl - quinoxaline - di - N - oxide is prepared by standing the corresponding 2-(a -acetoxy-lower alkyl) compound in methanol and 20% H2SO4.  2 - (a  - Methoxy lower alkyl) - 3 - lower alkyl quinoxaline is prepared by reacting the sodium salt of 2-(a -hydroxy lower alkyl)-3-lower alkyl quinoxaline with dimethyl sulphate.  2,3 - Di - (a  - lower alkoxy lower alkyl) quinoxaline is prepared by re-arrangement and hydrolysis of 2,3-di-lower alkyl quinoxaline di-N-oxide and treatment of the resulting 2,3 - di - (a  - hydroxy lower alkyl) quinoxaline with sodium hydride and the appropriate lower alkyl bromide.ALSO:Compositions useful in the control of chromic respiratory diseases in poultry comprise a compound of the general formula:  <FORM:1121104/A5-A6/1> where R1 is hydrogen, alkyl of up to 10 carbon atoms, a -hydroxy lower alkyl, a -lower alkanoyloxy lower alkyl, a -lower alkoxy lower alkyl or -CHO1 R2 is alkyl or up to 10 carbon atoms, lower alkanoyl, a -hydroxy lower alkyl, a -lower alkanoyloxy lower alkyl, a -lower alkoxy lower alkyl, or -CHO1 X1, X2, X3 and X4 are H or lower alkyl.  The compositions which also exhibit anthelmintic activity may be administered orally or parenterally and may be formulated as animal feed or drink compositions, aqueous and non-aqueous solutions, concentrates, capsules, tablets or liquid mixtures.  They may contain additives such as hyaluronidase, buffering agents, local anaesthetics and inorganic salts and may be used in combination with other drugs such as the tetracycline-type anti biotics, carbomycin, neomycin, bacitracin and tylosin.