FR2467630A1 - 7-Bromo-6-chloro-febrifugine ion-exchange resins - having coccidiostatic and anti-leucocytozoonosis activity with low animal toxicity - Google Patents
7-Bromo-6-chloro-febrifugine ion-exchange resins - having coccidiostatic and anti-leucocytozoonosis activity with low animal toxicity Download PDFInfo
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- FR2467630A1 FR2467630A1 FR7926221A FR7926221A FR2467630A1 FR 2467630 A1 FR2467630 A1 FR 2467630A1 FR 7926221 A FR7926221 A FR 7926221A FR 7926221 A FR7926221 A FR 7926221A FR 2467630 A1 FR2467630 A1 FR 2467630A1
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- Prior art keywords
- bromo
- resins
- salified
- chlorofébrifugine
- acid
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- 241001465754 Metazoa Species 0.000 title claims abstract description 13
- 239000003456 ion exchange resin Substances 0.000 title claims abstract description 4
- 229920003303 ion-exchange polymer Polymers 0.000 title claims abstract description 4
- 230000002192 coccidiostatic effect Effects 0.000 title abstract description 4
- 230000000694 effects Effects 0.000 title abstract 3
- 231100000419 toxicity Toxicity 0.000 title description 2
- 230000001988 toxicity Effects 0.000 title description 2
- 229920005989 resin Polymers 0.000 claims abstract description 46
- 239000011347 resin Substances 0.000 claims abstract description 46
- 239000002253 acid Substances 0.000 claims abstract description 14
- 230000002378 acidificating effect Effects 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 235000013305 food Nutrition 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000001110 calcium chloride Substances 0.000 claims description 3
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 235000015097 nutrients Nutrition 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 150000008043 acidic salts Chemical class 0.000 claims description 2
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000009938 salting Methods 0.000 claims 1
- 241000287828 Gallus gallus Species 0.000 abstract description 6
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 241000283690 Bos taurus Species 0.000 abstract description 2
- 241001494479 Pecora Species 0.000 abstract description 2
- 244000144977 poultry Species 0.000 abstract description 2
- UIHLDYLKWIWXAH-UHFFFAOYSA-N Febrifugine Natural products OC1CCNCC1CC(=O)CN2C=Nc3ccccc3C2=O UIHLDYLKWIWXAH-UHFFFAOYSA-N 0.000 abstract 1
- FWVHWDSCPKXMDB-UHFFFAOYSA-N febrifugine dihydrochloride Natural products OC1CCCNC1CC(=O)CN1C(=O)C2=CC=CC=C2N=C1 FWVHWDSCPKXMDB-UHFFFAOYSA-N 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 235000013330 chicken meat Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 208000003495 Coccidiosis Diseases 0.000 description 2
- 206010023076 Isosporiasis Diseases 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 230000002008 hemorrhagic effect Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 210000004877 mucosa Anatomy 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000223932 Eimeria tenella Species 0.000 description 1
- 235000019733 Fish meal Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010037549 Purpura Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- -1 alkali metal salt Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 206010034754 petechiae Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J47/00—Ion-exchange processes in general; Apparatus therefor
- B01J47/016—Modification or after-treatment of ion-exchangers
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
- A61K47/585—Ion exchange resins, e.g. polystyrene sulfonic acid resin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Fodder In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
La présente invention à la réalisation de laquelle ont participé Messieurs Jacques MARTEL, Jean TESSIER,
Pierre GIRAULT et Jean GRANDADAM concerne de nouvelles résines acides, leur procédé de préparation et leur application comme médicament.The present invention, to which Jacques MARTEL, Jean TESSIER, participated,
Pierre GIRAULT and Jean GRANDADAM concern new acid resins, their process of preparation and their application as medicine.
L'invention a pour objet les résines échangeuses d'ions du type acide dont les groupements acides sont au moins partiellement salifiés par. la 7-bromo 6-chlorofébrifugine. The subject of the invention is the acid-type ion exchange resins whose acidic groups are at least partially salified by. 7-bromo 6-chlorofebrifugine.
Par 7-bromo 6-chlorofébrifugine, on entend le composé racémique tel qutil est décrit dans le brevet français 1 550 956, ou l'un de ses isomères actifs, par exemple, l'isomère dextrogyre décrit dans la demande de brevet fran çais 2 339 402. By 7-bromo 6-chlorofebrifugine is meant the racemic compound as described in French Patent 1,550,956, or one of its active isomers, for example, the dextrorotatory isomer described in French patent application 2. 339,402.
Par résine acide, on entend notamment les résines à groupements sulfoniques, phosphoniques et carboxyliques. By acidic resin is meant in particular resins containing sulfonic, phosphonic and carboxylic groups.
L'invention a plus particulièrement pour objet les résines sulfoniques. The invention more particularly relates to the sulfonic resins.
Toutes les résines sulfoniques acides peuvent convenir pour préparer les produits de l'invention; on peut utiliser, par exemple, des polymérisats sulfonés de composés polyvinylaryliques, tels que décrits dans le brevet américain 2 366 007. All acidic sulfonic resins may be suitable for preparing the products of the invention; for example, sulfonated polymers of polyvinyl aryl compounds as described in US Pat. No. 2,366,007 may be used.
On peut utiliser notamment des polymérisats sulfonés de styrène divinylbenzène. It is possible in particular to use sulphonated polymers of styrene divinylbenzene.
L'invention n'est pas limitée à une catégorie de résine de granulométrie ou de réticulation donnée. The invention is not limited to a class of resin particle size or crosslinking given.
On peut utiliser tout particulièrement les résines Ámberlite"du type de celle utilisée dans la partie expérimentale exposée ci-après, par exemple; mais il va de soi que les autres résines du commerce à groupements acides forts peuvent convenir pour préparer les produits de l'invention. Amberlite resins of the type used in the experimental part described below can be used, for example, but it goes without saying that other commercial resins with strong acidic groups may be suitable for preparing the products of the invention. invention.
L'invention a plus particulièrement pour objet les résines définies précédemment, caractérisées en ce que les groupements acides ne sont que partiellement salifiés par la 7-bromo 6-chlorofébrifugine, notamment celles, caractérisées en ce que les groupements acides non salifiés par la 7-bromo 6-chlorofébrifugine sont salifiés par un métal alcalin et/ou alcalino-terreux. The subject of the invention is more particularly the resins defined above, characterized in that the acidic groups are only partially salified by 7-bromo-6-chloroferbrifugin, in particular those characterized in that the acidic groups not salified by 7- bromo 6-chlorofebrifugine are salified with an alkali metal and / or alkaline earth metal.
Par métal alcalin,on entend de préférence le sodium et le potassium. By alkali metal is preferably meant sodium and potassium.
Par métal alcalino-terreux, on entend de préférence le calcium. By alkaline earth metal is preferably meant calcium.
L'invention a plus spécialement pour objet les résines , caractérisées en ce que les groupements acides non salifiés par la 7-bromo 6-chlorofébriwugine sont salifiés par du sodium, ou par du calcium. The invention more particularly relates to resins, characterized in that the acid groups not salified by 7-bromo 6-chlorofebriugugine are salified with sodium, or with calcium.
L'invention a notamment pour objet les résines, caractérisées en ce qu'elles renferment de 1 à 20 et de préférence de 5 à 10% en poids de 7-bromo 6-chlorofébrifugine. The invention particularly relates to resins, characterized in that they contain from 1 to 20 and preferably from 5 to 10% by weight of 7-bromo 6-chlorofébrifugine.
L'invention a tout spécialement pour objet les résines définies précédemment , caractérisées en ce que la 7-bromo 6-chlorofébrifugine utilisée est le produit racémique. The subject of the invention is especially the resins defined above, characterized in that the 7-bromo 6-chlorofebrifugine used is the racemic product.
L'invention a tout spécialement pour objet les produits dont la préparation est donnée ci-après dans la partie expérimentale. The subject of the invention is especially the products whose preparation is given below in the experimental part.
Les produits de l'invention présentent d'intéressantes propriétés pharmacologiques et notamment une très bonne activité coccidiostatique ainsi qu'une faible toxicité. The products of the invention have interesting pharmacological properties and in particular a very good coccidiostatic activity and low toxicity.
L'invention a donc pour objet les produits de l'invention à titre de médicament. The subject of the invention is therefore the products of the invention as a medicament.
Les médicaments de l'invention peuvent être utilisés en particulier chez la volaille, les ovins et les bovins pour lutter contre la coccidiose. The drugs of the invention can be used especially in poultry, sheep and cattle to fight coccidiosis.
L'invention a également pour objet les compositions pharmaceutiques renfermant comme principe actif au moins un médicament défini précédemment. The invention also relates to pharmaceutical compositions containing as active ingredient at least one drug defined above.
Ces compositions sont utilisées, de préférence, par voie orale; elles peuvent être présentées sous forme de poudres, de comprimés, de comprimés enrobés, de cachets, de capsules, de granulés, d'émulsions ou de sirops. These compositions are preferably used orally; they may be presented in the form of powders, tablets, coated tablets, cachets, capsules, granules, emulsions or syrups.
Le ou les principes actifs, peuvent dtre incorporés à des excipients habituellement employés dans ces compositions, tels que le talc, la gomme arabique, le lactose, l'amidon, le stéarate de magnésium, les véhicules aqueux ou non, les corps gras d'origine animale ou végétale, les dérivés paraffiniques, les glycols, les divers agents mouillants, dispersants ou émulsifiants, les conservateurs. The active ingredient (s) may be incorporated into excipients usually employed in these compositions, such as talc, gum arabic, lactose, starch, magnesium stearate, aqueous or non-aqueous vehicles, fatty substances of the invention. animal or vegetable origin, paraffinic derivatives, glycols, various wetting, dispersing or emulsifying agents, preservatives.
La posologie utile est habituellement comprise entre 5 et 100 parties des produits de l'invention par million de la quantité de nourriture ingérée par l'animal. La posologie est donc comprise, par exemple, entre 100 et 200 00yIBe produit actif pour un poulet mangeant entre 20 et 200 g de nourriture par jour. The useful dosage is usually between 5 and 100 parts of the products of the invention per million of the amount of food ingested by the animal. The dosage is therefore, for example, between 100 and 20000IBI active product for a chicken eating between 20 and 200 g of food per day.
Les produits de l'invention sont très souvent incorpores aux compositions alimentaires qui renferment alors au moins un produit défini ci-dessus associé à un mélange nutritif adapté à l'alimentation animale. Le mélange nutritif peut varier selon l'espèce animale il peut renfermer des céréales, des sucres et graines, des tourteaux de soja, d'arachide et de tournesol, des farines d'origine animale, par exemple farines de poissons, des acides aminés de synthèse, des sels minéraux, des vitamines, des antioxydants. The products of the invention are very often incorporated into food compositions which then contain at least one product defined above associated with a nutrient mixture suitable for animal feed. The nutrient mixture may vary according to the animal species it may contain cereals, sugars and seeds, soya cake, peanut and sunflower, animal meal, for example fish meal, amino acids of synthesis, minerals, vitamins, antioxidants.
L'invention a donc ainsi pour objet les compositions alimentaires définies ci-dessus. The subject of the invention is thus the food compositions defined above.
L'invention a également pour objet un procédé de pré parution des résines définies ci-dessus, caractérisées en ce que l'on salifie au moins partiellement une résine par la 7-bromo 6-chlorofébrifugine et obtient ainsi le produit recherché. The subject of the invention is also a process for the preparation of the resins defined above, characterized in that at least partially a resin is salified with 7-bromo-6-chlorofebrifugine and thus obtaining the desired product.
L'invention a notamment pour objet un procédé, caractérisé en ce que l'on soumet une résine acide dont les groupements acides sont salifiés par un métal alcalin à l'action d'un sel acide de 7-bromo 6-chlorofébrifugine pour obtenir un sel mixte de métal alcalin et de 7-bromo 6-chlorofébrifugine de la résine acide, que l'on soumet, si désiré, à l'action d'un halogénure de métal alcalino-terreux pour obtenir un sel mixte de la 7-bromo 6-chlorofébrifugine et de métal alcalinoterreux. The invention particularly relates to a method, characterized in that an acidic resin whose acidic groups are salified with an alkali metal is subjected to the action of an acid salt of 7-bromo 6-chlorofebrifugine to obtain an mixed alkali metal salt and 7-bromo 6-chlorofebrifugin acid resin, which is subjected, if desired, to the action of an alkaline earth metal halide to obtain a mixed salt of 7-bromo 6-chlorofebrifugine and alkaline earth metal.
Par résine acide, on entend comme on l'a déjà indiqué de préférence une résine sulfonique. By acidic resin is meant as already indicated preferably a sulfonic resin.
Par sel acide, on entend de préférence un bromhydrate ou un chlorhydrate. By acidic salt is preferably meant a hydrobromide or a hydrochloride.
Par halogénure on entend,de préférence un chlorure ou un bromure. By halide is meant, preferably a chloride or bromide.
L'invention a tout spncialement pour objet un procédé caractérisé en ce que l'on soumet une résine sulfonique dont les groupements sulfoniques sont salifiés par du sodium à l'action du bromhydrate de 7-bromo 6-chlorofébrifugine pour obtenir un sel mixte de sodium et de 7-bromo 6-chlorofébrifugine de la résine acide, que l'on soumet, si désiré à l'action du chlorure de calcium, pour obtenir un sel mixte de calcium et de 7-bromo 6-chlorofébrifugine de la résine acide. The subject of the invention is especially a process characterized in that a sulphonic resin whose sulphonic groups are salified by sodium is subjected to the action of 7-bromo-6-chlorofebrifugine hydrobromide to obtain a mixed sodium salt. and 7-bromo 6-chlorofebrifugin acid resin, which is subjected, if desired to the action of calcium chloride, to obtain a mixed salt of calcium and 7-bromo 6-chlorofébrifugine acid resin.
Les exemples suivants illustrent l'invention sans toutefois la limiter
Exemple 1 : Sel mixte de sodium et de 7-bromo 6-chlorofébrifugine de résine sulfonique.The following examples illustrate the invention without limiting it
Example 1: Mixed salt of sodium and 7-bromo 6-chloroferbrifugine sulfonic resin.
On agite à 20'o250C pendant 16 heures, un mélange renfermant 100 g de résine Amberlite IRP69(Na+), un litre d'eau et 10 g de bromohydrate de 7-bromo 6-chlorofébrifugine racémique micronisé. On essore, lave à 11 eau, et sêche. On obtient un produit titrant 8,8% en poids de 7-bromo 6-chlorofébrifugine. A mixture containing 100 g of Amberlite IRP69 (Na +) resin, one liter of water and 10 g of micronized 7-bromo-6-chloroferrifugine bromohydrate is stirred at 20 ° C. for 16 hours. It is drained, washed with water and dried. A product titrating 8.8% by weight of 7-bromo 6-chlorofebrifugine is obtained.
Exemple 2 : Sel mixte de calcium et de 7-bromo 6-chlorofébrifugine.Example 2: Mixed salt of calcium and 7-bromo 6-chlorofébrifugine.
Dans 500 ml d'eau distillée, on agite pendant 20 heures à 20~ 250C, un mélange renfermant 20 g de produit préparé à l'exemple 1 et 20 g de chlorure de calcium. On filtre, lave à l'eau jusqu'à disparition d'halogène et seche. On obtient 20 g de produit titrant 7,9,' en poids de 7-bromo 6-chlorofébrifugine. In 500 ml of distilled water is stirred for 20 hours at 20 ~ 250C, a mixture containing 20 g of product prepared in Example 1 and 20 g of calcium chloride. Filtered, washed with water until halogen disappeared and dried. 20 g of product containing 7.9% by weight of 7-bromo-6-chloroferrifugin are obtained.
Exemple3 : Etude de l'activité coccidiostatique du produit préparé à l'exemple 1. Example 3 Study of the Coccidiostatic Activity of the Product Prepared in Example 1
On utilisé des poulets agies de 4 semaines. On les répartit en groupes de 20 animaux. La veille du jour de l'infestation, on donne aux poulets une ration alimentaire contenant ou ne contenant pas de produit de l'exemple 1; le jour J on infeste les poulets avec des coccidies Eimeria tenella souche sensible. Un groupe témoin n'est pas infesté. Active chickens of 4 weeks old were used. They are divided into groups of 20 animals. The day before the infestation, the chickens are given a food ration containing or not containing the product of Example 1; D-day infesting chickens with coccidia Eimeria tenella strain sensitive. A control group is not infested.
Le jour J + 7, les animaux sont pesés et sacrifiés. On day D + 7, the animals are weighed and sacrificed.
On prélève les coeca, on les ouvre, on les lave et on note les lésions en tenant compte des contenus coecaux (consistance, présence ou non d'hémorragies) selon le barême suivant
Note O : pas de lésion : coeca normaux.The coeca are removed, opened, washed and the lesions are recorded taking into account the coecal contents (consistency, presence or absence of hemorrhages) according to the following scale.
Note O: no lesion: normal coeca.
Note I : présence de pétéchies sur la muqueuse coecale. Note I: presence of petechiae on the mucosa coecale.
Note 2 : muqueuse coecale hémorragique, légérement épaissie, coeca de taille normale.Note 2: hemorrhagic coecal mucosa, slightly thickened, coeca of normal size.
Note 3 : muqueuse coecale hémorragique, épaissie, coeca raccourcie.Note 3: mucous coecal hemorrhagic, thickened, shortened coec.
Les résultats sont les suivants
<tb> <SEP> témoins <SEP> sains <SEP> témoins <SEP> Poulets <SEP> ayant
<tb> <SEP> contaminés <SEP> réçu <SEP> le <SEP> produit
<tb> <SEP> étudié <SEP> à <SEP> la
<tb> <SEP> dose <SEP> de <SEP> 42,86
<tb> <SEP> mg/kg
<tb> note <SEP> de <SEP> lésion <SEP> 0 <SEP> 2,7 <SEP> 0,05
<tb>
Conclusion : Le produit étudié est très actif contre la coccidiose, au bout d'une semaine de traitement les animaux infestés sont revenus à l'état normal.<tb><SEP> controls <SEP> healthy <SEP> controls <SEP> Chicken <SEP> having
<tb><SEP> Contaminated <SEP> Received <SEP><SEP> Product
<tb><SEP> studied <SEP> to <SEP> la
<tb><SEP> dose <SEP> of <SEP> 42.86
<tb><SEP> mg / kg
<tb> note <SEP> of <SEP> lesion <SEP> 0 <SEP> 2.7 <SEP> 0.05
<Tb>
Conclusion: The studied product is very active against the coccidiosis, after a week of treatment the infested animals returned to the normal state.
Exemple 4 : Etude de la toxicité.Example 4: Study of the toxicity.
La toxicité aigüe par voin orale du produit de l'exem ple 1 a été déterminée chez des souris miles et femelles selon la méthode de Finney. Oral acute toxicity of the product of Example 1 was determined in both female and female mice according to Finney's method.
Les résultats exprimés en DL 50 (la DL 50 étant la dose qui provoque la mortalité de 50% des animaux) ont été les suivants
<tb> Souris <SEP> mâles <SEP> Produit <SEP> de <SEP> l'exemple <SEP> 1 <SEP> DL <SEP> 50 <SEP> = <SEP> 66,09 <SEP> mg/kg
<tb> Souris <SEP> femelles <SEP> Produit <SEP> de <SEP> l'exemple <SEP> 1 <SEP> DL <SEP> 50 <SEP> = <SEP> 56,91 <SEP> mg/kg
<tb>
Conclusion : Le produit étudié présente une faible toxicité.<tb> Mice <SEP> males <SEP> Product <SEP> of <SEP> Example <SEP> 1 <SEP> DL <SEP> 50 <SEP> = <SEP> 66.09 <SEP> mg / kg
<tb> Mice <SEP> females <SEP> Product <SEP> of <SEP> Example <SEP> 1 <SEP> DL <SEP> 50 <SEP> = <SEP> 56.91 <SEP> mg / kg
<Tb>
Conclusion: The studied product has low toxicity.
Exemple 5 : Exemples de compositions pharmaceutiques.Example 5: Examples of pharmaceutical compositions.
Produit de l'exemple 1 ...................... 80g
Excipient à base de carbonate de chaux q.sp. ....... 1000g
Cette composition est à incorporer à raison de 500 g par tonne d'aliment complet. Product of Example 1 ...................... 80g
Excipient based on carbonate of lime q.sp. ....... 1000g
This composition is to be incorporated at the rate of 500 g per ton of complete feed.
Claims (12)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7926221A FR2467630A1 (en) | 1979-10-23 | 1979-10-23 | 7-Bromo-6-chloro-febrifugine ion-exchange resins - having coccidiostatic and anti-leucocytozoonosis activity with low animal toxicity |
| JP946480A JPS5662543A (en) | 1979-10-23 | 1980-01-31 | Novel acid type ion exchange resin* its manufacture and use as its chemical |
| US06/194,907 US4364928A (en) | 1979-10-23 | 1980-10-07 | Novel salts of ion exchange resins of the acid type |
| ES495937A ES8107049A1 (en) | 1979-10-23 | 1980-10-15 | Acid-type ion exchange resins, their preparation, their use as medicines and compositions containing them. |
| EP80401486A EP0027768B1 (en) | 1979-10-23 | 1980-10-20 | Acid-type ion exchange resins, their preparation, their use as medicines and compositions containing them |
| DE8080401486T DE3064539D1 (en) | 1979-10-23 | 1980-10-20 | Acid-type ion exchange resins, their preparation, their use as medicines and compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7926221A FR2467630A1 (en) | 1979-10-23 | 1979-10-23 | 7-Bromo-6-chloro-febrifugine ion-exchange resins - having coccidiostatic and anti-leucocytozoonosis activity with low animal toxicity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2467630A1 true FR2467630A1 (en) | 1981-04-30 |
| FR2467630B1 FR2467630B1 (en) | 1981-10-30 |
Family
ID=9230918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7926221A Granted FR2467630A1 (en) | 1979-10-23 | 1979-10-23 | 7-Bromo-6-chloro-febrifugine ion-exchange resins - having coccidiostatic and anti-leucocytozoonosis activity with low animal toxicity |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5662543A (en) |
| FR (1) | FR2467630A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6027821A (en) * | 1983-07-25 | 1985-02-12 | Shimadzu Corp | electronic balance |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1550956A (en) * | 1964-07-20 | 1968-12-27 | ||
| USRE26833E (en) * | 1968-05-15 | 1970-03-24 | Table vii |
-
1979
- 1979-10-23 FR FR7926221A patent/FR2467630A1/en active Granted
-
1980
- 1980-01-31 JP JP946480A patent/JPS5662543A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1550956A (en) * | 1964-07-20 | 1968-12-27 | ||
| USRE26833E (en) * | 1968-05-15 | 1970-03-24 | Table vii |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2467630B1 (en) | 1981-10-30 |
| JPS5662543A (en) | 1981-05-28 |
| JPS6360751B2 (en) | 1988-11-25 |
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