US3466370A - Process for treating helminth infestations using benzanilide derivatives and compositions for use therein - Google Patents

Process for treating helminth infestations using benzanilide derivatives and compositions for use therein Download PDF

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US3466370A
US3466370A US386392A US3466370DA US3466370A US 3466370 A US3466370 A US 3466370A US 386392 A US386392 A US 386392A US 3466370D A US3466370D A US 3466370DA US 3466370 A US3466370 A US 3466370A
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parts
infestations
dihydroxybenzanilide
compositions
agents
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Arthur William James Broome
William Glynne Moss Jones
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids

Definitions

  • This invention relates to new pharmaceutical compositions and more particularly it relates to new pharmaceutical compositions which contain as the active ingredients benzanilide derivatives which are of value in the treatment of animals suffering from helminth infestations.
  • compositions characterised by the presence therein as active ingredient(s) of one or more benzanilide derivatives of the formula:
  • W, X, Y, Z, M, P, Q and R which may be the same or different, stand for hydrogen, chlorine or bromine provided that not more than two of W, X, Y and Z, and not more than two of M, P, Q and R, stand for hydrogen, or the pharmaceutically-acceptable salts thereof together with a pharmaceutically-acceptable diluent or carrier therefore.
  • Suitable benzanilide derivatives of the above stated formula are, for example 3,3',5,5',6'pentachloro-2,2-dihydroxybenzanilide, 3,3',5 ,5 ',6-pentachloro-2,2'-dihydroxybenzanilide, 3,3,5,5',6,6'-hexachloro-2,2-dihydroxybenzanilide, 3,3',4,5 ,5 ,6,6-heptachloro-2,2-dihydroxybenzanilide, 3,3 '5 ,5 'tetrachloro-2,2-dihydroxybenzanilide and 3,3',4',5 ,5 ',6'-hexachloro-2,2'-dihydroxybenzanilide.
  • Suitable pharmaceutically-acceptable salts of the benzanilide derivatives used as active ingredients in the compositions of the present invention are, for example, alkali metal and alkaline earth metal salts, for example the sodium and calcium salts, and the salts of non-toxic organic bases, for example piperazine salts.
  • compositions of the invention may be designed either for oral or for parenteral administration and may be, for example, in the form of tablets, boluses, capsules, aqueous or oily solutions, aqueous or oily suspensions, emulsions, sterile injectable aqueous or oily solutions or suspensions, dispersible powders, premixes suitable for addition to animal foodstuffs or mixtures with animal foodstuffs.
  • compositions of the invention may contain standard excipients known to the art to be useful in the formulation of such compositions and they may contain, for example, inert diluents, fillers, disintegrating agents, bac- 3,466,370 Patented Sept. 9, 1969 "ice teriostats, bactericidal agents, sporicidal .agents, stabilising agents, thickening agents, preservatives, wetting agents, dispersing agents, suspending agents and pharmaceuticallyacceptable colouring agents.
  • the compositions may also optionally contain other substances of veterinary utility, for example vitaminaceous materials, drugs of veterinary utility and mineral salts.
  • Suitable tablets and boluses may be formulated by admixture of the activet ingredient(s) with known pharmaceutical excipients, for example inert diluents, for example calcium carbonate, calcium phosphate or lactose, disintegrating agents, for example maize starch or alginic acid, binding agents, for example starch, gelatin or acacia mucilage, lubricating agents, for example magnesium stearate, stearic acid or talc, and wetting agents, for example the alkali metal salts of sulphonated dialkylnaphthalenes.
  • Such tablets may optionally be coated by known techniques in order to delay disintegration in the upper gastrointestinal tract.
  • compositions in the form of capsules may consist, for example, of gelatine capsules containing active ingredient(s) only or the active ingredient(s) in admixture with inert diluents, for example lactose or sorbitol, or, for example, in solution or suspension in a vegetable oil.
  • inert diluents for example lactose or sorbitol
  • the aqueous suspensions, emulsions, oily solutions and suspensions of the invention may contain a sweetening agent, for example glycerol, dextrose or sucrose, and a fiavouring agent, for example vanillin or orange extract, in order to provide a palatable product.
  • a sweetening agent for example glycerol, dextrose or sucrose
  • a fiavouring agent for example vanillin or orange extract
  • the aqueous suspensions of the invention may also contain suitable suspending or thickening agents, for example sodium carboxymethylcellulose, wetting agents, for example condensation products of fatty alcohols with ethylene oxide, and suitable preservatives, for example methyl or propyl phydroxybenzoate.
  • the emulsion compositions of the invention may contain the active ingredient(s) dissolved in a suitable fat of vegetable or animal origin, for example arachis oil or cod liver oil, and may also contain sweetening agents and flavouring agents which may with advantage be essential oils.
  • a suitable fat of vegetable or animal origin for example arachis oil or cod liver oil
  • sweetening agents and flavouring agents which may with advantage be essential oils.
  • the emulsions may also contain emulsifying agents and dispersing agents, for example soya bean lecithin, polyoxyethylene sorbitan mono-oleate, gum acacia, gum tragacanth or casein, and preservatives, for example methyl or propyl p-hydroxybenzoate, and anti-oxidants, for example propyl gallate.
  • the oily solutions of the invention likewise may contain the active ingredient(s) in solution in a suitable fat of vegetable or animal origin, and may optionally contain flavouring agents to mask the taste and improve oral acceptability.
  • the oily solutions may also contain sweetening agents, for example icing sugar, in which case the oil phase may in addition contain a suspending agent, for example beeswax, to maintain the redispersion properties of the suspension.
  • the sterile injectable aqueous suspensions of the invention may contain a suspending or thickening agent, for example sodium carboxymethylcellulose, and a wetting or dispersing agent, for example a phenolpolyethylene oxide condensate, for example the condensation prodnot of octylcresol with about 8-l0 moleucular proportions of ethylene oxide.
  • the injectable oily solutions of the invention may be prepared from a non-toxic injectable fat or oil, for example arachis oil or ethyl oleate, and they may additionally contain gelling agents, for, example aluminum stearate, to delay adsorption within the body.
  • These aqueous and oily injectable preparations may contain preservatives such as methyl or npropyl p-hydroxybenzoate or chlorobutenol.
  • the dispersable powders of the invention may contain the active ingredient(s) in admixture with suitable wetting, dispersing and suspending agents.
  • the premixes of the invention preferably contain between 1% and 25% by weight of the active ingredient(s) and may contain the active ingredient in admixture with non-toxic diluents or carriers, for example talc, kaolin, chalk, lactose, urea, corn or meal, ground oyster shells, distillers dried grains and edible vegetable substances, for example commercial animal foodstuffs.
  • non-toxic diluents or carriers for example talc, kaolin, chalk, lactose, urea, corn or meal, ground oyster shells, distillers dried grains and edible vegetable substances, for example commercial animal foodstuffs.
  • the mixtures with animal foodstuffs which are intended to be orally administered as such to domestic animals preferably contain between 0.01% and 2% by weight of the benzanilide derivative(s) used as active ingredient( s)
  • the pharmaceutical compositions of the invention may optionally additionally contain other substances of veterinary utility, for example drugs of veterinary utility.
  • Suitable drugs of veterinary utility are, for example, anthelmintic drugs, for example, phenothiazine or methyridine and antibacterial drugs, for example benzylpenicillin, or sulphaguanidine.
  • benzanilide derivatives used as active ingredients in the compositions of the present invention may be prepared by conventional methods, for example, by interaction of a reactive derivative of an appropriately substituted salicylic acid, for example the corresponding carboxylic chloride, and a suitably substituted o-aminophenol.
  • compositions of the invention are effective in the treatment of helminth infestations, for example they are effective in removing liver fluke from domestic animals.
  • W, X, Y, Z, M, P, Q and R which may be the same or different, stand for hydrogen, chlorine or bromine provided that not more than two of W, X, Y and Z, and not more than two of M, P, Q and R, stand for hydrogen, or the pharmaceutically-acceptable salts there. of.
  • the process for the treatment of domestic animals, particularly sheep and cattle, by administration of the pharmaceutical compositions of the invention will depend upon the weight of the animal to be treated, the severity of the helminth infestations of the animal concerned and its general condition of health at the time of treatment.
  • Administration of one or more doses at the rate of 5100 mg. of active ingredient per kg. of body weight of animals and more particularly at a dosage rate of about 550 mg. of active ingredient per kg. of body weight of animal is satisfactory for the treatment of helminth infestations.
  • Example 1 parts of 3,3',5,5,6-pentachloro-2,2-dihydroxybenzanilide, M.P. 224 C., are ball-milled with 90 parts of a solution obtained by dissolving in 1,000 parts of water 1 part of a condensate of 1 molecular proportion of octylcresol with about 9 molecular proportions of ethylene oxide and 1 part of polyglycerolricinoleate.
  • aqueous suspension suitable for oral administration to domestic animals for the control of helminth infestations, for example liver fluke infestations.
  • Example 2 10 parts of 3,3',5,5,6,6-hexachloro-2,2'-dihydroxybenzanilide, M.P. 226 C., are ball-milled with 90 parts of a solution obtained by dissolving in 1,000 parts of water 2.5 parts of a condensate of 1 molecular propor- 4 tion of octycresol with about 9 molecular proportions of ethylene oxide. There is thus obtained a suspension suitable for administration to domestic animals for the treatment of helminth infestations, for example liver fluke infestations.
  • Example 3 100 parts of 3,3',5,5,6-pentachloro-2,2-dihydroxybenzanilide are mixed with 1 part of sodium ligninsulphonate and 2 parts of the sodium salt of a butylated-naphthalene sulphonic acid. The mixture thus obtained is reduced in particle size by passage through a mill. There is thus obtained a dispersible powder which can be added to water to form an aqueous suspension suitable for administration to domestic animals for the treatment of helminth infestations, for example liver fluke infestations.
  • Example 4 A mixture of 5 parts of 3,3',5,5',6,6'-hexachloro-2,2'- dihydroxybenzanilide and parts of maize oil is stirred at 50 C. for 30 minutes and is then. allowed to cool. There is thus obtained an oily solution suitable for administration to domestic animals for the treatment of helminth infestations, for example liver fluke infestations.
  • Example 5 A mixture of parts of 3,3',4',5,5',6,6'-heptachloro- 2,2-dihydroxybenzanilide, M.P. 243 C., and 400 parts of calcium phosphate is passed through a 60-mesb sieve. To the mixture are then added 30 parts of starch in the form of an aqueous paste and the resultant mxiture is blended and compressed into granules. The granules are passed through a lO-mesh sieve and dried at 50 C. The dried granules are passed through a 2O-mesl1 sieve and are then blended with a mixture of 5 parts of gum acacia and 20 parts of starch.
  • Example 6 A mixture of 100 parts of 3,3,5,5',6'pentachloro-2,2- dihydroxybenzanilide, 10 parts of maize starch, 10 parts of lactose and 2 parts of magnesium stearate is compressed into slugs and the slugs are passed through an S-mesh sieve and then through a 16-mesh sieve. The granules thus obtained are then compressed into tablets which are suitable for administration to domestic animals for the treatment of helminth infestations, for example liver fluke infestations.
  • Example 7 2 parts of the piperazine salt of 3,3',5,5,6,6-hexachloro- 2,2'-dihyd.roxybenzanilide are intimately mixed with 80 parts of distillers dried grains. There is thus obtained a premix suitable for addition to animal foodstuffs for the treatment of helminth infestations, for example liver fluke infestations, in domestic animals.
  • Example 8 20 parts of 3,3-5,5'-tetrachloro-2,2'-dihydroxybenzanilide are intimately mixed with 80 parts of wheat standard middling. There is thus obtained a premix suitable for addition to animal foodstuffs for the treatment of heminth infestations, for example liver fluke infestations, in domestic animals.
  • Example 9 100 parts of the calcium salt of 3,3',5,5',6,6-hexachloro- 2,2-dihydroxybenzanilide are mixed with 1 part of sodium ligninsulphonate and 1 part of the sodium salt of a bu-tylated-naphthalene-sulphonic acid. The mixture thus obtained is reduced in particle size by passage through a mill and there is thus obtained a dispersible powder which can be added to water to form an aqueous suspension suitable for administration to domestic animals for the treatment of helminth infestations, for example liver fluke infestations.
  • the amount of drug administered was at the rate of 25 mg./kg. of body weight.
  • the ewes expelled a total for each ewe respectively of 5, 34 and 86 dead adult lever fluke.
  • the ewes were then killed. At post mortem no fluke were found in the livers of two of the animals while in the liver of the third ewe seventeen immature fluke but no adult fluke were found.
  • Example 11 25 parts of the piperazine salt of 3,3',5,5,6-pentachloro- 2,2-dihydroxybenzanilide are intimately mixed with 75 parts of distillers dried grains. There is thus obtained a premix suitable for addition to animal foodstuffs for the treatment of helminth infestations, for example liver fluke infestations.
  • Example 12 A- mixture of 150 parts of the calcium salt of 3,3',5,5,6- pentachloro-2,2-dihydroxybenzanilide and 350 parts of calcium phosphate is passed through a 60-mesh sieve. To the mixture are then added 25 parts of starch in the form of an aqueous paste and the resultant mixture is blended and compressed into granules. The granules are passed through a IO-mesh sieve and dried at 50 C. The dried granules are further passed through a ZO-mesh sieve and are mixed with a mixture of 5 parts of gum acacia and 20 parts of starch. To the mixture thus obtained there are added 18 parts of talc and 1 part of magnesium stearate and the resulting mixture is blended and then compressed into tablets which are suitable for administration to domestic animals for the treatment of helminth infestation, for example liver fluke infestations.
  • Example 13 10 parts of 3,3',5,5',6-pentachloro-2,2'-dihydroxybenzanilide are dissolved in a solution of 2 parts of sodium hydroxide in 50 parts of water. Dilute hydrochloric acid is then added to the solution until the pH of the solution is 10 and the solution is thereafter filtered through a Seitz filter and the filtrate is filled into ampoules. There is thus obtained a sterile solution suitable for parenteral administration to animals for the treatment of helminth infestations.
  • Example 14 Two ewes, each with a liver fluke infestation, were treated by oral administration of 3,3',5,5',6-pentachloro- 2,2'-dihydroxybenzanilide as a suspension prepared as described in Example 1. The drug was administered at the rate of 10 mg./ kg. of body weight in the case of the first ewe and 15 mg./kg. of body weight in the case of the second ewe. During the six days following treatment the first ewe expelled a total of 94 fluke and the second ewe expelled a total of 100 fluke. The ewes were then killed. At post mortem no fluke were found in the livers of either ewe.
  • Example 15 Three cows, each with a liver fluke infestation, were treated by oral administration of 3,3',5,5',6-pentachloro- 2,2-dihydroxybenzanilide as a suspension prepared as described in Example 1. The amount of drug administered was at the rate of 10 mg./kg. of body weight. During the three days following treatment the cows expelled a total for each cow respectively of 94, 100 and 88 flukes The cows were killed six days following treatment. No flukes were found in the livers of the animals on post mortem examination.
  • composition for the treatment of helminth infestations comprising as active ingredient, an anthelmintically effective amount of at least one compound selected from the group consisting of benzanilide derivatives of the formula:
  • W, X, Y, Z, M, P, Q and R are selected from the group consisting of hydrogen, chlorine and bromine provided that at least two of W, X, Y and Z are selected from the group consisting of chlorine and bromine and that at least two of M, P, Q and R are selected from the group consisting of chlorine and bromine, and the alkali metal, alkaline earth metal and nontoxic pharmaceutically-acceptable organic base salts thereof, together with a pharmaceutically-acceptable carrier therefor.
  • composition as claimed in claim 1, wherein the benzanilide derivatives are selected from the group consisting of 3,3',5,5,6'-pentachloro-2,2-dihydroxybenzanilide, 3,3,5,5',6-pentachloro-2,2-dihydroxybenzanilide, 3, 3,5,5,6,6 hexachloro 2,2'-dihydr0xybenzanilide, 3,3, 4,5,5',6,6 heptachloro-Z,2-dihydroxybenzanilide, 3,3,5, 5-tetrachloro 2,2-dihydroxybenzanlide and 3,3,4',5,5', 6-hexachloro-2,2'-dihydroxybenzanilide.
  • A- composition as claimed in claim 1 wherein the salts are selected from the group consisting of sodium, calcium and piperazine salts.
  • a composition as claimed in claim 1 which is in a form selected from the group consisting of tablets, boluses, capsules, aqueous and oily solutions, dispersible powders, and mixtures with animal feeds.
  • composition as claimed in claim 1 which contains between 1% and 25% by weight of the active ingredient.
  • a composition as claimed in claim 5 which is an aqueous suspension and which contains as active ingredient 3,3,5,5.6 pentachloro 2,2 dihydroxybenzanilide together with a wetting agent which is a condensation produce of a fatty alcohol with ethylene oxide.
  • W, X, Y, Z, M, P, Q and R are selected from the group consisting of hydrogen, chlorine and'bromine provided that at least two of W, X, Y and Z are selected 3,466,370 7 8 from the group consisting of chlorine and bromine and References Cited at least two of M, P, Q and R are selected from the group UNITED STATES PATENTS consisting of chlorine and bromine, and the alkali metal,

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US386392A 1963-08-14 1964-07-30 Process for treating helminth infestations using benzanilide derivatives and compositions for use therein Expired - Lifetime US3466370A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3973038A (en) * 1973-04-20 1976-08-03 Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai Treatment of elevated histamine and uric acid levels
US3976784A (en) * 1974-02-04 1976-08-24 Imperial Chemical Industries Limited Method of treatment of liver fluke infections
WO2009019593A1 (en) * 2007-08-08 2009-02-12 Sanypet S.P.A. Pellet for animals and method for its production

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4659738A (en) * 1985-02-15 1987-04-21 The United States Of America As Represented By The Secretary Of The Army Topical prophylaxis against schistosomal infections

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2703322A (en) * 1951-03-17 1955-03-01 Hoffmann La Roche Derivatives of isonicotinyl hydrazine
US3072573A (en) * 1959-05-13 1963-01-08 Goodyear Tire & Rubber Stabilization of organic compositions with metal deactivators
US3305575A (en) * 1962-09-19 1967-02-21 Rhone Poulenc Sa Benzanilide derivatives

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2703322A (en) * 1951-03-17 1955-03-01 Hoffmann La Roche Derivatives of isonicotinyl hydrazine
US3072573A (en) * 1959-05-13 1963-01-08 Goodyear Tire & Rubber Stabilization of organic compositions with metal deactivators
US3305575A (en) * 1962-09-19 1967-02-21 Rhone Poulenc Sa Benzanilide derivatives

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3973038A (en) * 1973-04-20 1976-08-03 Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai Treatment of elevated histamine and uric acid levels
US3976784A (en) * 1974-02-04 1976-08-24 Imperial Chemical Industries Limited Method of treatment of liver fluke infections
WO2009019593A1 (en) * 2007-08-08 2009-02-12 Sanypet S.P.A. Pellet for animals and method for its production
US20100209572A1 (en) * 2007-08-08 2010-08-19 Sanypet S.P.A Process for producing a product for feeding animals

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GB1050767A (enrdf_load_stackoverflow)

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