EP0406364A1 - Veterinary composition and a process for the preparation thereof - Google Patents

Veterinary composition and a process for the preparation thereof

Info

Publication number
EP0406364A1
EP0406364A1 EP19900900317 EP90900317A EP0406364A1 EP 0406364 A1 EP0406364 A1 EP 0406364A1 EP 19900900317 EP19900900317 EP 19900900317 EP 90900317 A EP90900317 A EP 90900317A EP 0406364 A1 EP0406364 A1 EP 0406364A1
Authority
EP
European Patent Office
Prior art keywords
weight
composition
active ingredient
preparation
polymer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19900900317
Other languages
German (de)
French (fr)
Inventor
Péter S RKÖZY
András SZEGO "
Tamás DETRE
gnes ZSOLDOS
Anikó P LOS
Lajos Rejto "
Viktória KOLL RIK
Zoltán KAR DI
Zoltán SZAB
va MAGYAR DI
János GROSCH
Katalin M Rmarosi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chinoin Private Co Ltd
Original Assignee
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Publication of EP0406364A1 publication Critical patent/EP0406364A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone

Definitions

  • Antimicrobial and antiprotozoal wettable powder compositions having a special composition, containing 5-nitrofurfurylidene-3-amino-2-oxazolidone as active ingredient, and liotropic liquid crystalline compositions, optionally prepared therefrom in situ and a process for the preparation thereof.
  • compositions according to the invention can be used in veterinary therapy.
  • the purpose of the invention was to prepare such compositions that show a satisfactory stability in both concentrated and diluted conditions, have
  • the wettable powder composition of the invention contains 5-nitrofurfurylidene-3-amino-2-oxazolidone in 50 to 90 % by weight, surfactant(s) having more than 7 carbon atoms in 5 to 30 % by weight, a polymer having an a value characteristic of the degree of coiling and of the permeability by medium that is greater than 0.6 in 0.1 to 3 % by weight and, optionally, other well-known additive(s) suitable for use in veterinary therapy, such as gliding and colouring agents.
  • compositions can be prepared by mixing 5-nitrofurfurylidene-3-amino-2-oxazolidone in 50 to 90 % by weight, surfactant(s) having more than 7 carbon atoms in 5 to 30 % by weight, a polymer having an a value characteristic of the degree of coiling and of the permeability by medium that is greater than 0.6 in 0.1 to 3 % by weight and, optionally, other well-known additive(s) suitable for use in veterinary therapy, such as gliding and colouring agents; and by converting this mixture into a wettable powder composition according to methods known per se.
  • composition according to the invention may be prepared by carrying out the dissolution of the auxiliary materials and/or co-surfactants and the grafting with the solid materials simultaneously.
  • surfactants can be used:
  • Anionic materials carboxylic acid salts, e.g. fatty acid soaps; sulfates, e.g. alkyl sulfates, preferably sodium dodecyl sulfate; sulfonic acid salts, e.g.
  • alkyl benzenesulfonates e.g. alkyl phosphates and their salts
  • Cationic materials ammonium salts, e.g. cetyl-trimethyl-ammonium halides; quaternary nitrogen compounds, e.g. N-alkyl pyridinium salts; salts of adducts of alkyl amines or alkyl amides - with ethylene oxide, e.g.
  • Non-ionic materials fatty acid esters of polyhydric alcohols, ethoxylated-dianhydrosorbitol-stearates, o-phosphoric acid-trialkyl esters; ethylene oxide adducts, e.g. fatty acid - polyethylene glycol esters, fatty alcohol - ethylene oxide adducts, adducts of alkyl
  • Amphoteric materials preferably internal salts of betains or phosphoric acid derivatives formed with choline.
  • the following solvents may be used: water, aliphatic and/or aromatic solvents, e.g. mineral oils, low molecular ketones, mono- or polyhydric alcohols and ethers; vegetable and animal oils, saturated or unsaturated carboxylic acid having 1 to 6 carbon atoms or unsaturated carboxylic acids having more than 6 carbon atoms.
  • aliphatic and/or aromatic solvents e.g. mineral oils, low molecular ketones, mono- or polyhydric alcohols and ethers
  • vegetable and animal oils saturated or unsaturated carboxylic acid having 1 to 6 carbon atoms or unsaturated carboxylic acids having more than 6 carbon atoms.
  • esters containing one or more polar groups esters containing one or more polar groups
  • alcohols e.g. iso-octanol, dodecanol may be used.
  • polymer polyelectrolytes neutral polymers, natural macromolecules and derivatives thereof, polypeptides having an a value higher than 0.6, may be used.
  • the wettable compositions according to the invention form stable suspensions that show a liotropic liquid crystalline structure.
  • the present invention also provides antimicrobial and antiprotozal liotropic liquid crystalline compositions, which compositions contain a wettable powder composition according to the invention in 0.1 to 10 % by weight and water in an amount that makes up to 100 % by weight.
  • the liotropic liquid crystalline compositions may, optionally be prepared in situ by mixing an appropriate amount of the wettable powder with the drinking-water of the animals.
  • compositions according to the invention can be applied against the following microorganisms that are infectious for animals:
  • Gram positive bacilli Bacillus anthracis
  • Protozoa Giardia, Trypanosoma, Trichomonas
  • the ready-to-use solutions contain 10 to 40 mg/ml active ingredient.
  • Example 1 The details of the invention are illustrated by the following examples: Example 1
  • the active ingredient and the additives, used optionally, are homogenized.
  • the mixture of the surfactant(s) and the polymer is added to the homogenized powder in small portions. After each addition, the constituents are carefully homogenized.
  • active ingredient 85.5 % by weight aerosil 300 0.2 % by weight polyoxyethylene/20/-sorbitane- monostearate (TWEEN 60) 13.8 % by weight polyethylene oxide (Mw 1 000;
  • composition according to Example 1a is diluted with water to different extent: a/1 a/2 a/3 active ingredient 0.2 % + 0.5 % 2.0 % aerosil 0.0005 % 0.0016 % 0.005 %
  • TWEEN 60 0.032 % 0.08 % 0.32 % polyethylene oxide 0.001 % 0.003 % 0.03 %
  • compositions show a liquid crystalline structure examined with a polarization microscope (using crossed polarizer and analyzer and calcium sulphate red plate).
  • compositions 3a and 3b are diluted to 0.2 % by weight regarding the active agent.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Inorganic Chemistry (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention se rapporte à une composition pulvérulente mouillable à action anti-microbienne et anti-protozoaire, qui comprend comme ingrédient actif 50 à 90 % en poids de 5-nitrofurfurylidène-3-amino-2-oxazolidone ainsi que 5 à 30 % en poids d'un ou de plusieurs agents tensio-actifs ayant plus de 7 atomes de carbone, 0,1 à 3 % en poids d'un polymère ayant une valeur a caractéristique du degré d'enroulement et de la perméabilité à un milieu, qui est supérieure à 0,6, et éventuellement d'autres additifs bien connus appropriés pour leur usage en thérapie vétérinaire, tels que des agents de glissement et des agents colorants.The present invention relates to a wettable pulverulent composition with anti-microbial and anti-protozoal action, which comprises as active ingredient 50 to 90% by weight of 5-nitrofurfurylidene-3-amino-2-oxazolidone as well as 5 to 30% weight of one or more surfactants having more than 7 carbon atoms, 0.1 to 3% by weight of a polymer having a value a characteristic of the degree of coiling and the permeability to a medium, which is greater than 0.6, and possibly other well-known additives suitable for use in veterinary therapy, such as slip agents and coloring agents.

Description

Veterinary composition and a process for the preparation thereof
The subject of the invention:
Antimicrobial and antiprotozoal wettable powder compositions having a special composition, containing 5-nitrofurfurylidene-3-amino-2-oxazolidone as active ingredient, and liotropic liquid crystalline compositions, optionally prepared therefrom in situ and a process for the preparation thereof.
The compositions according to the invention can be used in veterinary therapy.
It is known that 5-nitrofurfurylidene-3--amino-2-oxazolidone exhibits an antimicrobial, antiprotozoal and anticoccidial effect and therefore has an application in the form of different compositions in poultry-farming and for the treatment of enteral infections of newborn animals (pig, calf) (US Patent No. 2 742 462).
The purpose of the invention was to prepare such compositions that show a satisfactory stability in both concentrated and diluted conditions, have
a uniform distribution of the active ingredient which hereby does not precipitate in the course of the application and therefore the danger of toxicosis is diminished.
The wettable powder composition of the invention contains 5-nitrofurfurylidene-3-amino-2-oxazolidone in 50 to 90 % by weight, surfactant(s) having more than 7 carbon atoms in 5 to 30 % by weight, a polymer having an a value characteristic of the degree of coiling and of the permeability by medium that is greater than 0.6 in 0.1 to 3 % by weight and, optionally, other well-known additive(s) suitable for use in veterinary therapy, such as gliding and colouring agents.
The above compositions can be prepared by mixing 5-nitrofurfurylidene-3-amino-2-oxazolidone in 50 to 90 % by weight, surfactant(s) having more than 7 carbon atoms in 5 to 30 % by weight, a polymer having an a value characteristic of the degree of coiling and of the permeability by medium that is greater than 0.6 in 0.1 to 3 % by weight and, optionally, other well-known additive(s) suitable for use in veterinary therapy, such as gliding and colouring agents; and by converting this mixture into a wettable powder composition according to methods known per se.
Alternatively the composition according to the invention may be prepared by carrying out the dissolution of the auxiliary materials and/or co-surfactants and the grafting with the solid materials simultaneously.
According to the invention the following surfactants can be used:
Anionic materials: carboxylic acid salts, e.g. fatty acid soaps; sulfates, e.g. alkyl sulfates, preferably sodium dodecyl sulfate; sulfonic acid salts, e.g.
alkyl benzenesulfonates; phosphates, e.g. alkyl phosphates and their salts; esters of ethoxylated fatty alcohols prepared with inorganic acids, preferably with sulfuric acid, phosphoric acid and their salts, etc.
Cationic materials: ammonium salts, e.g. cetyl-trimethyl-ammonium halides; quaternary nitrogen compounds, e.g. N-alkyl pyridinium salts; salts of adducts of alkyl amines or alkyl amides - with ethylene oxide, e.g.
ethoxylated coconut fatty acid amide.
Non-ionic materials: fatty acid esters of polyhydric alcohols, ethoxylated-dianhydrosorbitol-stearates, o-phosphoric acid-trialkyl esters; ethylene oxide adducts, e.g. fatty acid - polyethylene glycol esters, fatty alcohol - ethylene oxide adducts, adducts of alkyl
phenols and ethylene oxide, preferably alkyl phenol
- polyglycol ether; adducts of alkyl amines or alkyl amides with ethylene oxide; adducts of polypropylene glycols with ethylene oxide; o-phosphoric acid triesters of alkyl polyethylene glycol ethers, etc.
Amphoteric materials: preferably internal salts of betains or phosphoric acid derivatives formed with choline.
In the compositions according to the invention the following solvents may be used: water, aliphatic and/or aromatic solvents, e.g. mineral oils, low molecular ketones, mono- or polyhydric alcohols and ethers; vegetable and animal oils, saturated or unsaturated carboxylic acid having 1 to 6 carbon atoms or unsaturated carboxylic acids having more than 6 carbon atoms.
As co-surfactants alcohols, ketones and
esters containing one or more polar groups; fatty
alcohols, e.g. iso-octanol, dodecanol may be used.
As polymer polyelectrolytes, neutral polymers, natural macromolecules and derivatives thereof, polypeptides having an a value higher than 0.6, may be used.
As polymer polyvinyl pyrrolidone (Mw = 18 000 -- 25000; a = 0.77 - 0,85), polyethylene oxide
(Mw = 1 000; a = 0.82), polyvinyl alcohol (Mw = 78 000; a = 0.77), polyethylene amine (Mw = 12 000; a = 0.89), polyacrylate (Mw = 500 000; a = 0.91), oligodextrane (Mw = 2 000; a = 0.60) and polyethylene oxide - polypropylene oxide (Mw = 10 000; a = 0.84) may preferably be used.
The wettable compositions according to the invention form stable suspensions that show a liotropic liquid crystalline structure. The present invention also provides antimicrobial and antiprotozal liotropic liquid crystalline compositions, which compositions contain a wettable powder composition according to the invention in 0.1 to 10 % by weight and water in an amount that makes up to 100 % by weight. The liotropic liquid crystalline compositions may, optionally be prepared in situ by mixing an appropriate amount of the wettable powder with the drinking-water of the animals.
The compositions according to the invention can be applied against the following microorganisms that are infectious for animals:
Gram positive cocci: Streptococcus haemolyticus
Stretpcoccus faecalis
Gram negative cocci: Neisseriae
Gram positive bacilli: Bacillus anthracis
Clostridium perfringens
Corynebacteria
Gram negative bacilli: Aerobacter aerogenes
Escherichia coli
Klebsiellae, Salmonellae, Shingellae, Proteae
Protozoa: Giardia, Trypanosoma, Trichomonas
Fungi
The ready-to-use solutions contain 10 to 40 mg/ml active ingredient.
The details of the invention are illustrated by the following examples: Example 1
Wettable powder composition
The active ingredient and the additives, used optionally, are homogenized. The mixture of the surfactant(s) and the polymer is added to the homogenized powder in small portions. After each addition, the constituents are carefully homogenized. a) active ingredient 85.5 % by weight aerosil 300 0.2 % by weight polyoxyethylene/20/-sorbitane- monostearate (TWEEN 60) 13.8 % by weight polyethylene oxide (Mw = 1 000;
a = 0.82) 0.5 % by weight b) active ingredient 50 % by weight aerosil 300 0.3 % by weight polyoxyethylene/20/-sorbitanetristearate (TWEEN 65) 13.3 % by weight polyvinyl pyrrolidone (Mw = 25 000;
a = 0.85) 1 % by weight saccharose ad 100 % by weight c) active ingredient 90 % by weight Tween 60 9.5 % by weight polyacrylic acid (Mw = 500 000,
a = 0.91) 0.5 % by weight Example 2
Liotropic liquid crystalline composition
The composition according to Example 1a is diluted with water to different extent: a/1 a/2 a/3 active ingredient 0.2 %+ 0.5 % 2.0 % aerosil 0.0005 % 0.0016 % 0.005 %
TWEEN 60 0.032 % 0.08 % 0.32 % polyethylene oxide 0.001 % 0.003 % 0.03 %
(Mw = 1 000; a = 0.82)
water ad 100 ad 100 % ad 100 by weight
2 hours after the dilution the above compositions show a liquid crystalline structure examined with a polarization microscope (using crossed polarizer and analyzer and calcium sulphate red plate).
Example 3
Comparative composition
a) active ingredient 85.5 % by weight aerosil 300 0.2 % by weight polyoxyethylene-sorbitol-septaoleate 8.3 % by weight (HLB 9.5)
ethoxylated nonylphenol polyglycol
ether (E0 = 10) 4.5 % by weight saccharose 1.5 % by weight b) active ingredient 50 % by weight aerosil 300 0.3 % by weight polyoxyethylene-sorbitol-septaloate (HLB 9.5) 7.0 % by weight ethoxylated nonylphenol polyglycol
ether (E0 = 10) 5.0 % by weight soybean lecithine 2.0 % by weight saccharose ad 100 % by weight c) active ingredient 90 % by weight
Tween 60 10 % by weight
The compositions 3a and 3b are diluted to 0.2 % by weight regarding the active agent.
2 hours after the dilution the diluted compositions do not show any liquid crystalline structure.

Claims

C l a i m s
1. An antimicrobial and antiprotozal wettable powder composition, comprising as active ingredient 50 to 90 % by weight of 5-nitrofurfurylidene--3-amino-2-oxazolidone and surfactant(s) having more than 7 carbon atoms in 5 to 30 % by weight, a polymer having an a value characteristic of the degree of coiling and of the permeability by medium that is greater than 0.6 in 0.1 to 3 % by weight and, optionally, other well-known additives suitable for the use in veterinary therapy, such as gliding and colouring agents.
2. A process for the preparation of the composition in Claim 1, wherein 5-nitrofurfurylidene--3-amino-2-oxazolidone in 50 to 90 % by weight, surfactant(s) having more than 7 carbon atoms in 5 to 30 % by weight, a polymer having an a value characteristic ofthe degree of coiling and of the permeability by medium that is greater than 0.6 in 0.1 to 3 % by weight and, optionally, other well-known additives suitable for use in veterinary therapy, such as gliding and colouring agents are mixed together and converted into a wettable powder composition by methods known per se.
3. An antimicrobial and antiprotozoal inoculated liotropic liquid crystalline composition, comprising the composition of claim 1 in 0.1 to 10 % by weight and an additional amount of water that makes up to
100 % by weight.
4. A process for the preparation of the composition of Claim 3, comprising admixing the composition of Claim 1 in 0.1 to 10 % by weight with an additional amount of water that makes up to 100 % by weight.
EP19900900317 1988-12-22 1989-12-20 Veterinary composition and a process for the preparation thereof Withdrawn EP0406364A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU655988A HU204697B (en) 1988-12-22 1988-12-22 Process for producing veterinary composition comprising n-(5-nitrofufurilidene)-3-amino-2-oxazolidone
HU655988 1988-12-22

Publications (1)

Publication Number Publication Date
EP0406364A1 true EP0406364A1 (en) 1991-01-09

Family

ID=10971813

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19900900317 Withdrawn EP0406364A1 (en) 1988-12-22 1989-12-20 Veterinary composition and a process for the preparation thereof

Country Status (4)

Country Link
EP (1) EP0406364A1 (en)
BR (1) BR8907256A (en)
HU (1) HU204697B (en)
WO (1) WO1990006752A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103536624B (en) * 2013-10-31 2016-08-17 成都乾坤动物药业有限公司 A kind of wettable three-ingredient white composition powder and preparation method thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3075876A (en) * 1961-06-07 1963-01-29 Norwich Pharma Co Alimentary composition for combatting enteric infection in monkeys and method of using same
NL6509059A (en) * 1964-07-22 1966-01-24
DE1232703B (en) * 1965-03-27 1967-01-19 Boehringer & Soehne Gmbh Process for the production of a preparation form of N- (5-nitro-2-furfurylidene) -3-amino-2-oxazolidone which is easily suspendable in water
EP0012523B2 (en) * 1978-11-20 1988-02-03 American Home Products Corporation Therapeutic compositions with enhanced bioavailability and process for their preparation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9006752A1 *

Also Published As

Publication number Publication date
HUT53803A (en) 1990-12-28
HU204697B (en) 1992-02-28
WO1990006752A1 (en) 1990-06-28
BR8907256A (en) 1991-04-23

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