Patent GB-989578-A (GB)
Title: Quinolyl-(8)-oxy-acetamide derivatives and their use in animal feeds
IPC: A23K50/30
Filed: 1963-05-06
Abstract: The invention comprises compounds of the general formula <FORM:0989578/C2/1> wherein R1 and R2 independently of each other represent hydrogen, substituted or unsubstituted alkyl radicals, alkenyl radicals, phenyl radicals or halogenated phenyl radicals, or R1 and R2 together with the adjacent nitrogen atom form a heterocyclic ring which may further contain oxygen or a second nitrogen atom, or, in cases where R1 represents hydrogen, R2 can also represent an amino group, X and Y independently of each other represent alkyl, halogenoalkyl, aryl or aralkyl radicals, halogen atoms, aliphatic or aromatic acyl radicals, the nitro group, the amino group, or acylamino, alkylamino or dialkylamino groups, and m and n each represent whole numbers from 0 to 3, and their water-soluble non-toxic salts with inorganic and organic acids. Numerous preferred values of R1, R2, X and Y are specified.  The compounds may be prepared (i) by reacting a compound of the general formula <FORM:0989578/C2/2> with a compound of the general formula <FORM:0989578/C2/3> wherein R1, R2, X, Y, m and n are as defined above, M represents hydrogen, an alkali metal atom or the equivalent of an alkaline earth metal atom, and Z represents a halogen atom, a phenylsulphonyloxy group or a p-toluene-sulphonyloxy group, or (ii) by reacting a compound of the general formula <FORM:0989578/C2/4> with a compound of the general formula <FORM:0989578/C2/5> or a reactive functional derivative thereof, wherein R1, R2, X, Y, m and n are as defined above and Q represents an alkoxy radical, a hydroxy radical or a halogen atom.  Salts are obtained by dissolving compounds of the general Formula I in an alcohol and/or a ketone and then adding at least the equivalent amount of an organic or inorganic acid. Examples are given. a -(Quinolyl-(8)-oxy)-acetic acid ethyl ester, a -(2-methylquinolyl-(8)-oxy)-acetic acid ethyl ester and a -(5,7-dibromoquinolyl-(8)-oxy)-acetic acid methyl ester are prepared by reacting the appropriate 8-hydroxyquinoline with the appropriate ester of chloro-acetic acid. a -(5,7-Dichloroquinolyl-(8)-oxy)-acetic acid ethyl ester is prepared from the potassium salt of 8-hydroxy-5,7-dichloroquinoline and chloroacetic acid ethyl ester.ALSO:A growth-promoting feed supplement for dogs, pigs, cattle, sheep and fowls, which is also a coccidiostat, is a quinolyl-(8)-oxyacetic acid derivative of formula <FORM:0989578/A1-A3/1> or a non-toxic acid addition salt thereof, wherein R1 and R2, independently of each other, represent hydrogen, substituted or unsubstituted alkyl radicals, alkenyl radicals, phenyl radicals or halogenated phenyl radicals, or R1 and R2 together with the adjacent nitrogen atom form a heterocyclic ring which may further contain oxygen or a second nitrogen atom, or, in cases where R1 represents hydrogen, R2 can also represent an amino group, X and Y independently of each other represent alkyl, halogenoalkyl, aryl or aralkyl radicals, halogen atoms, oliphatic or aromatic aryl radicals, the nitro group, the amino group, or arylamino, alkylamino or dialkylamino groups, and m and n each represent whole numbers from 0 to 3.  Examples of the derivatives are a -[2 methyl-quinolyl-(8)-oxy]-acetic acid amide, a -[2,5,-dimethylquinolyl-(8)-oxy]-acetic acid amide, the phosphoric acid salt of a -[2-methylquinolyl-(8)-oxy]-acetic acid amide, a -[5-benzoyl-quinolyl-(8)-oxy]-acetic acid amide, a -[2-methyl-5, 7-dichlorquinolyl-(8)-oxy]-acetic acid hydroxide, the hydrochloride of a -[2-methylquinolyl-(8)-oxy]-acetic acid amide, and a -[5-acetylquinolyl-(8)-oxy]-acetic acid morpholide. Numerous other compounds and salts thereof are specified.  The derivative may be added to the feed directly in solid form or in solution.  A preparation of 5-10% of the derivative in meal may be mixed in the feed to give an ultimate concentration of 0.01-0.03%.  A mixture of the derivative and sugar or dextrin may be added to milk for calves.