Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
  • A61K31/47—Quinolines; Isoquinolines
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
  • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
  • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
• • C—CHEMISTRY; METALLURGY
  • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
  • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
  • C25B3/00—Electrolytic production of organic compounds
• • C—CHEMISTRY; METALLURGY
  • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
  • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
  • C25B3/00—Electrolytic production of organic compounds
  • C25B3/20—Processes
  • C25B3/23—Oxidation

Definitions

• This invention relates to heterocyclic compounds and more particularly it relates to quinoline derivatives which possess anti-coccidial activity.
• Another preferred group of compounds of the invention comprises those quinoline derivatives wherein R stands for an alkyl radical containing at least 12 and not more than 14 carbon atoms, R stands for the methyl or ethyl radical, and the quinoline nucleus is substituted in the 6-position by an alkyl radical of not more than 6 carbon atoms.
• R when it stands for an alkyl radical there may be mentioned, for example, a straightor branched-chain alkyl radical containing not more than 15 carbon atoms, for example the isopropyl, n-dodecyl or n-tetradecyl radical.
• R when it stands for an aryl radical there may be mentioned, for example, the phenyl radical, optionally substituted by one or more alkyl radicals of not more than 5 carbon atoms, for example methyl radicals.
• R there may pe mentioned, for example, a straightor branched-chain alkyl radical of not more than 4 carbon atoms, for example the methyl ethyl, n-propyl or isopropyl radical.
• additional substituents which may be present on the quinoline nucleus there may be mentioned, for example, one or more substituents selected from alkyl radicals of not more than 10 carbon atoms, alkenyl and alkoxy radicals of not more than 6 carbon atoms, and haolgen atoms.
• substituents which may be present on the quinoline nucleus are, for example, the methyl, ethyl, n-propyl, n-butyl, isobutyl, n-hexyl, n-octyl, allyl, u-methylallyl, methoxy, ethoxy, n-propoxy, isopropoxy and chloro substituents.
• R O' 'N CH-OI-I(COOR% wherein R and 'R have the meanings stated above, and wherein the benzene ring may optionally bear one or more additional substituents.
• the cyclisation may be' carried out by, for example, heating the starting material, conveniently at a temperature above 200 C.
• the cyclisation reaction may be carried out in the presence of an inert diluent or solvent, for
• the esterification may conveniently be carried out by conventional means, for example by the interaction of an alcohol of the formula R .OH, wherein R has the meaning stated above, with the abovementioned acid in the presence of a mineral acid catalyst, for example sulphuric acid or hydrochloric acid; or by the interaction of the said alcohol of the formula R .OH, with an activated derivative of the abovementioned acid, for example the acid halide, for example the acid chloride.
• a mineral acid catalyst for example sulphuric acid or hydrochloric acid
• an activated derivative of the abovementioned acid for example the acid halide, for example the acid chloride.
• the hydrolysis may be carried out under acidic conditions, for example, in the presence of an inorganic acid, for example hydrochloric acid, or it may be carried out under basic conditions, for example, in the presence of an inorganic base, for example an alkali metal hydroxide, for example sodium hydroxide or potassium hydroxide.
• the hydrolysis may conveniently be carried out in the presence of a diluent or solvent, for example ethanol, water or ace tone, and it may be accelerated or completed by the application of heat.
• quinoline nucleus has at least one unsubstituted position in the carbocyclic ring of the quinoline nucleus.
• the halogenation may be effected by the use of an N- halogenated amide, for example an N-halosuccinimide, for example N-chlorosuccinimide, and it may be carried out in an inert diluent or solvent, for example dimethylformamide.
• the reaction may be accelerated or completed by the application of heat.
• the quinoline derivatives of this invention possess valuable anti-coccidial properties. They are especially active against the intestinal species Ez'meria brunetti, and certain of them are also active against the caecal species E. tenella and E. necatrix. They are therefore useful as the active ingredient in veterinary compositions such as concentrated food pre-mixes or medicated foodstuffs for the prophylactic treatment of coccidiosis in poultry or other domestic animals.
• compositions comprising one or more quinoline derivatives of the formula.
• R stands for an alkyl, aryl or aralkyl radical, any of which may optionally be substituted
• R stands for an alkyl radical
• the quinoline nucleus may optionally bear one or more additional substituents, pro vided that when both R and R stand for alkyl radicals of not more than 4 carbon atoms, then the quinoline nucleus does not bear as sole additional substituent, an alkoxy radical of not more than 4 carbon atoms in the 6- position, together with a non-toxic diluent or carrier.
• the veterinary compositions may be, for example, concentrated food pre-mixes wherein the active ingredient is mixed with an inert diluent, for example kaolin, talc, calcium carbonate, fullers earth, attapulgus clay or ground oyster shells, or is mixed with a foodstuff as diluent, for example whole ground corn, corn distillers dry grain, wheat shorts or corn cob meal. It is intended that the said pre-mixes should be further diluted with an animal foodstuff in order to provide a suitable medicated foodstuff which can be eaten directly by poultry or other domestic animals.
• an inert diluent for example kaolin, talc, calcium carbonate, fullers earth, attapulgus clay or ground oyster shells
• a foodstuff as diluent for example whole ground corn, corn distillers dry grain, wheat shorts or corn cob meal.
• such medicated foodstuff compositions intended for direct feeding to poultry should contain between about 0.00005% and about 0.1% by weight of active ingredient in the composition, and more particularly between 0.0001% and 0.001% by weight in the food of the preferred active ingredients. It is likewise preferred that the concentrated pre-mixes should contain between about 0.1% and about by weight of the active ingredient and more particularly bet-ween 0.2% and 2% by weight of the preferred active ingredients.
• compositions of the invention may additionally contain one or more other compounds of known veterinary utility, for example one or more known anthelmintics, or growth promotors, antibacterials or tranquilisers.
• EXAMPLE 1 93 parts of diethyl 3-benzyloxyanilinomethylenemalonate are added gradually to 450 parts of boiling diphenyl ether. The mixture is heated under reflux for 30 mins. and then cooled. The solid product is filtered off, washed with carbon tetrachloride, and crystallised from dimethylformamide. There is thus obtained ethyl 7-benzyloxy-4-hydroxyquinoline-3-carboxylate, M.P. 295 C.
• the diethyl 3-benzyloxyanilinomethylenemalonate used as starting material may be obtained as follows:
• EXAMPLE 2 17 parts of 3-n-dodecyloxyaniline and 13.5 parts of di ethyl ethoxymethylenemalonate are heated at 100 C. for 2 hours, and the crude diethyl 3-n-dodecyloxyanilinomethylenemalonate so obtained is added gradually to 100 parts of boiling diphenyl ether. The mixture is heated under reflux for 30 minutes and then cooled. The solid product is filtered ofl, washed with carbon tetrachloride, and crystallised from dimethylformamide. There is thus obtained ethyl 7-n-dodecyloxy-4-hydroxyquinoline 3-carboxylate, M.P. 255 C.
• EXAMPLE 4 A mixture of 3.5 parts of 3-benzyloxy-4-n-propylaniline and 3.4 parts of diethyl ethoxymethylenemalonate is heated at 100 C. for 2 hours, and the crude diethyl 3-benzyloxy-4-n-propylanilinomet-hylenemalonate so obtained is added in one portion to 35 parts of stirred, boiling diphenyl ether. The mixture is stirred and heated under reflux for 5 minutes, and then cooled. The solid product is filtered off, washed with petroleum ether (B.P. 4060 C.), and recrystallised from dimethylformamide. There is thus obtained ethyl 7-benzyloxy-4-hydroxy-6-n-propylquinoline- 3-carboxylate, M.P. 299 C.
• the 3-benzyloxy-4-n-propylaniline used as starting material may be obtained as follows:
• EXAMPLE 6 A mixture of 5 parts of 7-benzyloxy-4-hydroxyquinoline-3-carboxylic acid and parts of thionyl chloride is heated under reflux for 2 hours with a catalytic amount of pyridine. The excess of thionyl chloride is evaporated, 25 parts of benzene are added, and the mixture evaporated to dryness. The solid acid chloride so obtained is heated under reflux for 1 hour with 50 parts of dry methanol, and the solution is then evaporated. The solid residue is heated at 100 C. for a few minutes with 50 parts of water, and the resulting mixture cooled and filtered. The solid product is recrystallised from dimethylformamide. There is thus obtained methyl 7-benZyloxy-4-hydroxyquinoline-3- carboxylate, M.P. 273 C.
• the 7-benzyloxy-4-hydroxyquinoline 3 carboxylic acid used as starting material may be obtained as follows:
• EXAMPLE 7 The procedure described in Example 6 is repeated except that the 5 parts of 7-benzyloxy-4-hydroxyquinoline- 3-carboxylic acid are replaced by 5 parts of 7-benzyloxy- 4-hydroxy-6-n-propylquinoline-3-carboxylic acid. There is thus obtained methyl 7-benzyloxy-4-hydroxy-6-n-propylquinoline-3-carboxylate, M.P. 292 C.
• the 7 benzyloxy-4-hydroxy-6-n-propylquinoline-3-car- 'boxylic acid used as starting material may be obtained as follows:
• EXAMPLE 8 A mixture of 5 parts of 4-allyl-3-benzyloxyaniline and 3.85 parts of dimethyl methoxyrnethylenemalonate is heated at 100 C. for 2 hours.
• the solid reaction product is crystallised from a mixture of benzene and petroleum ether, B.P. 6080 C.
• dimethyl 4- allyl-3-benzyloxyanilinomethylenemalonate M.P. 92 C.
• 5 parts of this latter compound are added in one portion to parts of stirred, boiling diphenyl ether.
• the mixture is stirred and heated under reflux for 5 minutes, and then cooled.
• the solid product is filtered off, washed with petroleum ether (B.P. 4060 C.), and recrystallised from dimethylformamide.
• M.P. 283 C The 4-allyl-3-benzyloxyaniline used as starting material may be obtained as follows:
• EXAMPLE 9 The process of Example 2 is repeated except that the 17 parts of 3-n-dodecyloxyaniline are replaced by 9.3 parts of 3-isopropylaniline. There is thus obtained ethyl 4hydroxy-7-isopropoxyquinoline-3-carboxylate, M.P. 246 C.
• EXAMPLE 10 8 parts of 3-n-dodecyloxyaniline and 4.5 parts of dimethyl methoxymethylenemalonate are heated at 100 C. for 2 hours.
• the solid reaction product is crystallised from petroleum ether (B.P. 4060 C.) 8 parts of the dimethyl 3-n-dodecyloxyanilinomethylenemalonate, M.P. 58 C. so obtained are added to parts of boiling diphenyl ether.
• the mixture is heated under reflux for 20 minutes and then cooled.
• the solid product is heated in boiling carbon tetrachloride, and the mixture is then cooled and filtered.
• the solid product is crystallised from dimethyl formamide, and there is thus obtained methyl 7-n-dodecycloxy- 4-hydroxyquinoline-3-carboxylate, M.P. 255 C.
• the 3-benzyloxy-4-(a-methylallyDaniline used as starting material may be prepared as follows:
• EXAMPLE 12 The procedure described in Example 6 is repeated except that the 50 parts of methanol are replaced by 50 parts of n-propanol. There is thus obtained n-propyl 7 benzyloxy 4 hydroxyquinoline-3-carboxylate, M.P. 293 C.
• EXAMPLE 13 The procedure described in Example 6 is repeated except that the 50 parts of methanol are replaced by 50 parts of isopropanol. There is thus obtained isopropyl 7 benzyloxy 4 hydroxyquinoline 3 carboxylate, M.P. 297 C.
• EXAMPLE 14 4 parts of 3-(3-phenylpropoxy)aniline and 3 parts of dimethyl methoxymethylenemalonate are heated at 100 C. for 3 hours, and the crude dimethyl 3-(3-phenylpropoxy)anilinomethylenemalonate so obtained is added to 40 parts of boiling diphenyl ether. The mixture is heated under refiux for 5 minutes and then cooled. The solid product is filtered off, washed With petroleum ether (B.P. 4060 C.), and crystallised from 2-ethoxyethanol. There is thus obtained methyl 4-hydroxy-7-(3-phenylpropoxy)quinoline-3-carboxylate, M.P. 255 C.
• the 3-(3-phenylpropoxy)aniline used as starting material may be obtained as follows:
• EXAMPLE 8.5 parts of 3-(4-methylbenzyloxy)aniline and 7 parts of dimethyl methoxymethylenemalonate are heated at 100 C. for 3 hours, and the crude dimethyl 3-(4-methylbenzyloxy anilinomethylenemalonate so obtained is added to 80 parts of boiling diphenyl ether.
• the mixture is heated under reflux for minutes, cooled, and diluted with 100 parts of petroleum ether (B.P. 6080 C.).
• the solid which separates is filtered off, and boiled with methanol and then crystallised from dimethylforrnarnide. There is thus obtained methyl 4-hydroxy-7-(4-methylbenzyloxy)quinoline-3-carboxylate, M.P. 254 C.
• the 3-(4-methylbenzyloxy)aniline used as starting material may be prepared as follows:
• EXAMPLE 16 1 part of 7-benzyloxy-4-hydroxyquinoline-3-carboxylic acid is heated under reflux with 1 part of concentrated sulphuric acid in 50 parts of absolute ethanol for 24 hours. The cooled solution is diluted with water and the separated solid is washed with alcohol and crystallised from dimethylformamide. There is thus obtained ethyl 7 benzyloxy 4-hydroxyquinoline-3-carboxylate, M.P. 295 C.
• EXAMPLE 17 A mixture of 7.6 parts of 3-(4-chlorobenzy1oxy)-4-npropylaniline and 5.7 parts of dimethyl methoxymethylenemalonate is heated at C. for 2 hours and then cooled. The crude dimethyl 3-(4-chlorobenzyloxy)-4-npropylanilinomethylenemalonate so obtained is added to 48 parts of stirred, boiling Dowtherm A. (Dowtherm is a trademark). The solution is stirred and heated under reflux for 5 mins. and then cooled. The crystalline product which separates is filtered off, washed with methanol and recrystallised from dimethyl formamide. There is thus obtained methyl 7-(4-chlorobenzyloxy)-4- hydroxy-6-n-propylquinoline-3-carboxylate, M.P. 295 C.
• the 3-(4-chlorobenzyloxy)-4-n-propylaniline may be obtained as follows:
• EXAMPLE 18 A mixture of 5.1 parts of 3-(4-methylphenoxy)-aniline and 6.4 parts of diethyl ethoxymethylenemalonate is heated at 100 C. for 2 hours and then cooled. The crude diethyl 3 (4 methylphenoxy)anilinomethylenemalonate so obtained is added to 40 parts of stirred, boiling Dowtherm A (Dowtherm is a trademark). The solution is stirred and boiled for 15 mins. and then cooled. The product is filtered off, washed with ethanol and recrystallised from dimethyl formamide. There is thus obtained ethyl 4 hydroxy 7 (4 methylphenoxy)quinoline 3 carboxylate, M.P. 260 C.
• the 3-t4-methylphenoxy)aniline may be obtained as follows:
• EXAMPLE 19 The procedure described in Example 17 is repeated except that the 7.6 parts of 3-(4-chlorobenzyloxy)-4-npropylaniline are replaced by 7.6 parts of 3-(2-chlorobenzyloxy)-4-n-propylaniline. There is thus obtained methyl 7 (2 chlorobenzyloxy) 4 hydroxy 6 n propylquinoline-3-carboxylate, M.P. 283 C.
• EXAMPLE 20 The procedure described in Example 17 is repeated except that the 7.6 parts of 3-(4-chlorobenzyloxy)-4-n-propylaniline are replaced by 8.5 parts of 3-(2,4-dichlorobenzyloxy)-4-n-propylaniline or 5.3 parts of 3-phenoxyaniline. There is thus obtained methyl 7-(2,4-dichlorobenzyloxy)-4-n-propylaniline, 8.8 parts of 3-dodecyloxy- 4-n-propylaniline or 5.3 parts of 3phenoxyaniline. There is thus obtained methyl 7 (2,4 dichlorobenzyloxy)-4- hydroxy-6-npropylquinoline-3-carboxylate, M.P.
• the 3-(2-methylphenoxy)aniline, B.P. 126-136 C./0.6 mm. may be obtained by repeating the process described in the second part of Example 18 except that the 42 parts of p-cresol are replaced by 42 parts of o-cresol.
• EXAMPLE 22 A mixture of 5.4 parts of 3-benzyloxy-4-n-hexyl aniline and 4.4 parts of diethyl ethoxymethylenemalonate are heated at 100 C. for 1 hour and the crude diethyl 3- benzyloxy-4-n-hexylanilinomethylenemalonate so obtained is added in one portion to 10 parts of stirred, boiling diphenyl ether. The mixture is stirred and heated under reflux for 5 minutes, and then cooled. The solid product is filtered off, Washed with carbon tetrachloride, and recrystallised from dimethyl formamide. There is thus obtained ethyl 7-benzyloxy-4-hydroxy-6-n-hexylquinoline-3- carboxylate, M.P. 283285 C.
• the 3-benzyloxy-4-n-hexylaniline used as starting material may be obtained as follows:
• EXAMPLE 23 The proceduce described in Example 22 is repeated except that the 5.4 parts of 3-benzyloxy-4-n-hexylaniline are replaced by 4.4 parts of 3-benzyloxy-4-methylaniline, 6.1 parts of 3-benzyloxy-4-n-butylaniline, or 5.8 parts of 3-benzyloxy-4-n-octylaniline. There is thus obtained ethyl 7 benzyloxy-4-hydroxy-6-methylquinoline-3 carboxylate, M.P. 32l323 C., ethyl 7-benzyloxy-6-n-butyl-4-hydroxyquinoline-3-carboxylate, M.P. 297-298 C., or ethyl 7- benzyloxy-4-hydroxy-6-n-octylquinoline 3 carboxylate, M.P. 261-262 C. respectively.
• EXAMPLE 24 The procedure described in Example 22 is repeated except that the 4.4 parts of diethyl ethoxymethylenemalonate are replaced by 2.6 parts of dimethyl methoxymethylenemalonate. There is thus obtained methyl 7-benzyloxy- 4-hydroxy-6-n-hexylquinoline-3 carboxylate, M.P. 278- 280 C.
• EXAMPLE 26 3.7 parts of 3-benzyloxy-4-methoxyaniline and 3.0 parts of dimethyl methoxymethylenemalonate are heated at C. for 3 hours and the crude dimethyl 3-benzyloxy- 4-methoxyanilinomethylenemalonate so obtained is added carefully to 21 parts of stirred, boiling diphenylether. The mixture is stirred and heated under reflux for 3 minutes and then cooled rapidly. The solid product is filtered, washed with petroleum ether (B.P. 40-60 C.) and crystallised from dimethylformamide. There is thus obtained methyl 7-benzyloxy-4-hydroxy-6-methoxyquinoline-3-car- :boxylate, M.P. 287288 C.
• EXAMPLE 27 7.7 parts of dimethyl 3-benzyloxy-4-ethoxyanilinomethylenemalonate are added carefully to 30 parts of stirred, boiling diphenyl ether. The mixture is stirred and heated under reflux for 3 minutes and then cooled rapidly. The solid product is filtered, Washed with petroleum ether (B.P. 40-60 C.) and crystallised from dimethylforrnamide. There is thus obtained methyl 7-benzyloxy-4-hydroxy-6-ethoxyquinoline-3-carboxylate, M.P. 281-282 C.
• the 3-benzyloxy 4 ethoxyaniline may be obtained as follows:
• the 3-benzyloxy-4 ethoxynitrobenzene may be obtained as follows:
• the 3-benzyloxy-4 n propoxynitrobenzene may be obtained by repeating the procedure described in Example 27 for the preparation of 3-benzyloxy-4-ethoxynitrobenzene except that the 57 parts of ethyl chloride are replaced by 52 parts of n-propyl iodide. There is thus obtained 3-benzyloxy-4-n-propoxynitrobenzene, M.P. 73- 74 C.
• EXAMPLE 31 15 parts of ethyl 7-benzyloxy-4-hydroxyquinoline-3- carboxylate are dissolved in 2400 parts of dry dimethylformamide. 40.5 parts of N-chlorosuccinimide are added, and the mixture is heated at 100 C. for 6 /2 hours. The dimethylformamide is removed by distillation, and the residue extracted with 400 parts of boiling ethanol and filtered rapidly. The separated solid is crystallised from dimethylformamide. There is thus obtained ethyl 7-benzyloxy-4-hydroxy 6,8 dichloroquinoline 3 carboxylate, M.P. 285-287" C.
• EXAMPLE 33 The process of Example 32 is repeated except that the 6.6 parts of dimethyl methoxymethylenemalonate are replaced by 10 parts of diethyl ethoxymethylenemalonate. There is thus obtained ethyl 7-n-tetradecyloxy-4-hydroxyquinoline-3-carboxylate, M.P. 243245 C- EXAMP-LE 34 EXAMPLE 35 11 parts of 3-(4-nitrobenzyloxy) aniline and 8.2 parts of dimethyl methoxymethylenemalonate are intimately mixed and heated at 100 C. for 2 hours. The product is cooled and crystallised from dimethylformamide to give dimethyl (4 nitrobenzyloxy)anilinomethylenemalonate, M.P.
• the 3-(4-nitrobenzyloxy)aniline used as starting material may be obtained as follows:
• EXAMPLE 36 9 parts of N-chlorosuccinimide are added to a solution of 3.3 parts of methyl 7-(2,4-dichlorobenzyloxy)-4-hydroxy-6n-propylquinoline-3-carboxylate in 1500 parts of dry dimethylformamide, and the mixture is heated at 100 C. for 12 hours. The mixture is cooled and evaporated, and the residue is crystallised from ethanol. There is thus obtained methyl 8-chloro-7-(2,4-dichlorobenzyloxy)-6-npropylquinoline-3-carboxylate, M.P. 309-311 C.
• EXAMPLE 40 1 part of a concentrated food pre-mix, obtained as described in Example 39, is uniformly dispersed in 2000 parts of a commercial poultry starting mash. There is thus obtained a medicated foodstuff suitable for feeding t poult y for the prophylactic control of coccidiosis.
• a veterinary composition comprising, as the essential active component, an effective amount of a quinoline-3-carboxylic ester selecter from the group consisting of compounds of the formula:
• R is selected from the group consisting of benzyl and chlorobenzyl
• R is alkyl of 14 carbon atoms
• X is selected from the group consisting of hydrogen, alkyl of 1-6 carbon atoms, alkenyl of up to 4 carbon atoms and alkoxy of 1-4 carbon atoms, and compounds of the formula:
• R has the meaning stated above and Y is selected from the group consisting of hydrogen and alkyl of 1-4 carbon atoms, in admixture with a major amount of a non-toxic veterinary carrier therefor.
• composition as claimed in claim 1 wherein the quinoline-3-carboxylic ester is methyl 7-benzyloxy-6-nbutyl-4-hydroxyquinoline-3-carboxylate.
• composition according to claim 1 which is in the form of a concentrated food pre-mix.
• composition according to claim 1 which is in the form of a medicated foodstuff.
• R is selected from the group consisting of benzyl and chlorobenyl
• R is alkyl of 1-4 carbon atoms
• X is selected from the group consisting of hydrogen, alkyl of 1-6 carbon atoms, alkenyl of up to 4 carbon atoms and alkoxy of l4 carbon atoms, and compounds of the formula:
• R has the meaning stated above and Y is selected from the group consisting of hydrogen and alkyl of 14 carbon atoms.
• quinoli'ne-3-carboxylic ester is methyl 7-benzyloxy-6-nbutyl-4 hydroxyquinoline-3-carboxylate.

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• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Electrochemistry (AREA)
• Materials Engineering (AREA)
• Metallurgy (AREA)
• Medicinal Chemistry (AREA)
• Pharmacology & Pharmacy (AREA)
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• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Quinoline Compounds (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

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Cited By (1)

• 1966
  • 1966-02-17 NL NL6602067A patent/NL6602067A/xx unknown
• 1968
  • 1968-06-10 US US735533A patent/US3557283A/en not_active Expired - Lifetime

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