EP1411894A2 - Pharmazeutische zubereitungen enthaltend fluorochinolonbeladene ionentauscherharze - Google Patents

Pharmazeutische zubereitungen enthaltend fluorochinolonbeladene ionentauscherharze

Info

Publication number
EP1411894A2
EP1411894A2 EP02743262A EP02743262A EP1411894A2 EP 1411894 A2 EP1411894 A2 EP 1411894A2 EP 02743262 A EP02743262 A EP 02743262A EP 02743262 A EP02743262 A EP 02743262A EP 1411894 A2 EP1411894 A2 EP 1411894A2
Authority
EP
European Patent Office
Prior art keywords
ion exchanger
pharmaceutical preparation
loaded
preparation according
ion
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.)
Ceased
Application number
EP02743262A
Other languages
German (de)
English (en)
French (fr)
Inventor
Dirk Mertin
Wolfgang Block
Hans-Jürgen HAMANN
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.)
Bayer AG
Original Assignee
Bayer Healthcare AG
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 Bayer Healthcare AG filed Critical Bayer Healthcare AG
Publication of EP1411894A2 publication Critical patent/EP1411894A2/de
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions

Definitions

  • the present invention relates to pharmaceutical preparations which contain one or more active substances which are bound to an ion exchanger.
  • active substance / ion exchanger particles are smaller than 50 ⁇ m.
  • the abovementioned publication describes formulations of bitter-tasting quinolonecarboxylic acid derivatives which are bound to ion-exchange resins, and the preparation thereof.
  • Weakly acidic cationic types can be considered as ion exchange resins, and their matrix can be gel-like or macroporous.
  • the base monomers for the ion exchangers are polymerizable monomers which can be functionalized to form cation exchange resins by means of corresponding side chains.
  • the ion exchangers are known under the trade names Lewatit ® , Amberlite ® , Purolite ® or Dowex ® . Corresponding formulations are described in veterinary medicine as feed medicines for pigs.
  • formulations containing the loaded cation-exchange resins prepared according to EP-A-295 495 still have disadvantages when administered orally to pets, in particular cats, for example in terms of acceptance. These are attributed to a sandy taste sensation due to ion exchange particles that are larger than approx. 50 ⁇ m.
  • No. 3,138,525 describes the improvement of palatabilty by grinding a strongly acidic ion exchanger loaded with amprotropin.
  • the particle reduction described there to a particle size of 40-250 ⁇ m is not sufficient to improve acceptance in cats.
  • WO 89/12 452 describes the grinding of
  • Cholestyramine a strongly basic ion exchanger, described using a cutting mill.
  • the resulting particles are 75% smaller than 65 ⁇ m and 30% smaller than 30 ⁇ m.
  • Cutting mills are suitable for grinding soft polymers, such as cholestyramine, but not for more brittle brittle polymers such as the cation exchange resins described above.
  • the use of attrition mills has also only been described for the comminution of cholestyramine (EP 26 574).
  • acidic ion exchange resins and their formulations can also be ground using suitable grinding methods in such a way that at least 90% of the particles have a size of less than 50 ⁇ m.
  • Preparations containing these ground ion exchange resins have unexpectedly good technical and pharmaceutical properties and are also well accepted, for example, by pets, especially cats.
  • the invention therefore relates to:
  • Cation exchanger-bound active ingredients characterized in that the loaded cation exchanger is dispersed in a carrier medium and at least 90% of the dispersed ion exchange particles have a size of less than 50 ⁇ m.
  • Particles of at least 90% have a size of less than 50 ⁇ m for the production of pharmaceutical preparations for oral administration.
  • the cationic ion exchange resins can for example be a gel or. have a macroporous matrix.
  • the base monomers for the ion exchangers are polymerizable monomers which can be converted into cation exchange resins by appropriate functionalization. Examples of monomers which may be mentioned are (meth) acrylic acid esters, (meth) acrylonitrile and styrene derivatives. Polyvinyl compounds such as divinylbenzene, ethylene glycol dimethacrylate or methylene bisacrylamide are used as further comonomers for the production of the base polymers. Condensation resins which lead to cation exchangers are also suitable, for example phenol-formaldehyde resins with corresponding functional groups.
  • the ion exchangers that can be used are not new. More detailed information on various types of ion exchangers and their production can be found, for example, in Ullmann's Encyclopedia of Industrial Chemistry (Release 2001, 6th Edition).
  • the preferred macroporous resins can have different pore volumes.
  • the degree of crosslinking of the suitable ion exchange resins should preferably be up to
  • the synthetic resins are usually in grain sizes of 1 to 300 ⁇ m, preferably 10 to 200 ⁇ m.
  • Commercial ion exchange resins are e.g. B. Lewatit ® , Amberlite ® , Dowex ® and Purolite ® .
  • the strongly acidic ion exchangers used are preferably those based on poly (styrene, divinylbenzene) sulfonic acid. Examples include:
  • Amberlite IRP 69 poly (styrene, divinylbenzene) sulfonic acid in the Na form, particle size (before grinding): 10-25%> 75 ⁇ m, max. 1%> 150 ⁇ m, K-
  • Purolite C 100 H MR poly (styrene, divinylbenzene) sulfonic acid in the H form, particle size (before grinding): max. 1%> 150 ⁇ m, exchange capacity: at least 3.2 eq / kg
  • Purolite C 100 MR poly (styrene, divinylbenzene) sulfonic acid in the Na form, corresponds to Amberlite IRP 69
  • Lewatit Catalyst K 1481 poly (styrene, divinylbenzene) sulfonic acid in the H-
  • Lewasorb SW 12 poly (styrene, divinylbenzene) sulfonic acid in the Na form, otherwise corresponds to Lewatit K 1481.
  • Weakly acidic cation exchangers are preferably used as ion exchangers, in particular those based on methacrylic acid-divinylbenzene copolymer. Examples are:
  • Amberlite IRP 64 methacrylic acid-divinylbenzene copolymer in the H form, particle size (before grinding): 15-30%> 75 ⁇ m, max. 1%> 150 ⁇ m, exchange capacity: min. 10 eq / kg
  • Purolite C 1 15 H MR methacrylic acid-divinylbenzene copolymer in the H form, otherwise like Purolite C 1 15 K MR.
  • Lewatit CNP 105 macroporous methacrylic acid-divinylbenzene copolymer in the H form, exchange capacity min. 1, 4 eq / 1.
  • Active pharmaceutical ingredients with a basic function that are capable of binding to cation exchangers can be used. This is particularly useful for drugs that smell unpleasant or lead to an unpleasant taste sensation when administered orally.
  • active substances are quinolone antibiotics, as are disclosed, inter alia, in the following documents: US 4,670,444 (Bayer AG), US 4,472,405 (Riker Labs), US 4,730,000 (Abbott), US 4,861,779 ( Pfizer), U.S. 4,382,892 (Daiichi), U.S. 4,704,459
  • the active substance-loaded ion exchange resins are produced in water or polar organic solvents, such as, for example, alcohols, such as methanol or etha- nol, ketones such as acetone or mixtures thereof. Water is particularly preferred.
  • the ion exchanger and active ingredient are stirred in the medium at room temperature or elevated temperature until the active ingredient is completely bound. The dispersion medium is then separated off by filtration, centrifugation or decanting and the residue is dried.
  • the ion exchanger can be ground in the dry state or preferably by wet grinding, examples of which are air jet grinding and grinding with a bead mill.
  • the ion exchanger can be ground unloaded, but grinding in the loaded state is preferred. For this, the
  • the ion exchanger is dispersed and milled in a suitable carrier together with other auxiliaries, such as wetting agents, preservatives or viscosity-increasing substances.
  • auxiliaries such as wetting agents, preservatives or viscosity-increasing substances.
  • Water, organic solvents, mineral, fatty oils or mixtures thereof, but especially fatty oils, are suitable as carrier liquids.
  • the particles are always smaller than 100 ⁇ m, preferably 75 ⁇ m.
  • the particle sizes specified here are always determined by laser scattered light measurement (e.g. with a Malvern Mastersizer or the like).
  • the pharmaceutical preparation according to the invention owing to the small particle size of the charged ion exchanger [D (0.9) ⁇ 50 ⁇ m], was distinguished by an excellent palatabilty, e.g. in cats.
  • the grinding of the ion exchanger in liquid formulations not only significantly delays the formation of a sediment, but the sediment is also very easy to shake again.
  • the better ability to shake the finely ground ion exchanger in particular was surprising, since Certainly, fine particulate, sedimenting suspensions tend to be poorly redispersible (caking) due to the large specific surface and thus high adhesive forces of the particles.
  • compositions according to the invention are generally suitable for
  • Livestock and breeding animals include mammals such as Cattle, horses, sheep, pigs, goats, camels, water buffalos, donkeys, rabbits, fallow deer, reindeer, fur animals such as Mink, chinchilla, raccoon and birds such as Chickens, geese, turkeys, ducks, pigeons and bird species for home and zoo keeping.
  • Laboratory and experimental animals include mice, rats, guinea pigs, golden hamsters, dogs and cats.
  • Hobby animals include rabbits, hamsters, guinea pigs, mice, horses, reptiles, appropriate bird species, dogs and cats.
  • Fish should also be mentioned, namely commercial, breeding, aquarium and ornamental fish of all ages that live in fresh and salt water.
  • Useful and farmed fish include carp, eel, trout, white fish, salmon, bream, roach, rudd, chub, sole, plaice, halibut, Japanese yellowtail (Seriola quinqueradiata), Japanaal (Anguilla japonica), red seabream (Pagurus major ), Seabass (Dicentrarchus labrax), Gray mullet (Mugilus cephalus), Pompano, Gilthead seabream (Sparus auratus), Tilapia spp., Cichlid species such as Plagioscion, Channel catfish.
  • the agents according to the invention are particularly suitable for the treatment of fish fry, for example carp with a body length of 2 to 4 cm.
  • the agents are also very suitable for eel fattening.
  • the preparations according to the invention are preferably used in hobby animals such as hamsters, rabbits, guinea pigs, cats and dogs. They are particularly suitable for use in cats.
  • the application can be prophylactic as well as therapeutic.
  • the preparations according to the invention are preferably administered orally.
  • compositions suitable for animals are e.g. those in which the improvement in taste plays a role in the intake or in which a delayed release of the active ingredient after the application is sought.
  • solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules, or liquid or semi-solid pharmaceutical forms such as suspensions or pastes, e.g. can be used orally.
  • the latter are produced by suspending the resin loaded with active ingredient in a carrier liquid, optionally with the addition of further auxiliaries such as wetting agents, dyes, absorption-promoting substances, preservatives, antioxidants or light stabilizers.
  • suspensions By adding substances that increase the viscosity, these suspensions can also be used as so-called “semi-solid" preparations, e.g. Ointments are administered.
  • formulations of this type can be used as an oral paste in cats, dogs and horses.
  • the active substance-loading resin is mixed with suitable carriers, if appropriate with the addition of auxiliaries, and brought into the desired shape.
  • Inorganic and organic substances serve as such.
  • Inorganic substances are, for example Table salt, carbonates such as calcium carbonate, hydrogen carbonates, aluminum oxides, silicas, clays, precipitated or colloidal silicon dioxide, phosphates.
  • Organic substances are e.g. Sugar, cellulose, food and feed such as milk powder, animal meal, cereal flour and meal, starches.
  • Excipients are preservatives, antioxidants, dyes, which have already been listed above.
  • auxiliaries are lubricants and lubricants such as Magnesium stearate, stearic acid, talc, bentonite, decay-promoting substances such as starch or cross-linked polyvinylpyrrolidone, binders such as e.g. Starch, gelatin or linear polyvinylpyrrolidone and dry binders such as microcrystalline cellulose.
  • lubricants and lubricants such as Magnesium stearate, stearic acid, talc, bentonite, decay-promoting substances such as starch or cross-linked polyvinylpyrrolidone, binders such as e.g. Starch, gelatin or linear polyvinylpyrrolidone and dry binders such as microcrystalline cellulose.
  • the active substance-loaded resins are distributed as homogeneously as possible in a liquid carrier medium, if appropriate with the aid of other auxiliaries, such as wetting agents, preservatives or viscosity-increasing substances.
  • Carrier liquids are all homogeneous solvents and solvent mixtures, but especially water, paraffin oils and fatty oils, such as. B. Neutral oil.
  • the ion exchanger loaded with the active ingredient is in the invention
  • Preparations preferably in an amount of 1 to 50 wt .-%, particularly preferably 5 to 25 wt .-% based on the total weight of the preparation.
  • the carrier liquid is used in the amount suitable for setting the necessary consistency, usually this is preferably 50 to 99% by weight, particularly preferably 70 to 95% by weight, based on the total weight of the preparation.
  • wetting agents dispersants
  • anionic surfactants including emulsifiers such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt, lignin sulfonates or dioctyl sulfosuccinate
  • cationic surfactants including emulsifiers such as cetyltrimethylammonium chloride
  • Ampholytic surfactants including emulsifiers such as di-Na-N-lauryl- ⁇ -iminodipropionate or lecithin
  • Non-ionic surfactants including emulsifiers, such as polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethylene stearate, alkylphenol polyglycol ether, polyethylene-polypropylene block copolymers.
  • emulsifiers such as polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethylene stearate, alkylphenol polyglycol ether, polyethylene-polypropylene block copolymers.
  • the nonionic surfactants are particularly preferred.
  • Wetting agents are preferably used in an amount of 0.1 to 10% by weight, particularly preferably 0.5 to 5% by weight, based on the total weight of the preparation.
  • auxiliaries include: • Dyes, ie all dyes approved for use on humans or animals, which can be dissolved or suspended. Dyes are preferably used in an amount of 0.001 to 5% by weight, particularly preferably 0.01 to 2% by weight, based on the total weight of the preparation.
  • Antioxidants such as Sulphites or metabisulphites such as potassium metabisulphite, ascorbic acid, butylated hydroxytoluene, butylated hydroxyanisole, tocopherols. Antioxidants are preferably used in an amount of 0.001 to 5% by weight, particularly preferably 0.01 to 2% by weight, based on the total weight of the preparation.
  • Thickeners or viscosity-increasing substances such as inorganic thickeners such as bentonites, colloidal silica, aluminum monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates, alginates, gelatin,
  • Polyvinyl pyrrolidone Polyethylene glycols, waxes, gum arabic and xanthan gum or mixtures of the listed substances.
  • Thickeners are preferably used in an amount of 0.01 to 10% by weight, particularly preferably 0.01 to 5% by weight, based on the total weight of the preparation.
  • the preparations according to the invention are preferably liquid or semi-liquid suspensions.
  • these suspensions can also be administered as semi-solid preparations such as pastes.
  • formulations of this type can be used as an oral paste in animals.
  • the active substance-loaded ion exchange resins can be added to the feed as such or in the form of premixes or feed concentrates.
  • Premixes and feed concentrates are mixtures of the active ingredient with a suitable carrier.
  • the carrier substances include the feed materials or mixtures thereof, as well as the inert carrier substances mentioned above.
  • Regulate fluidity and miscibility e.g. Silicas, bentonites, lignin sulfonates.
  • antioxidants such as BHT or preservatives such as sorbic acid or calcium propionate can be added.
  • Liquids such as paraffin oils, vegetable oils and propylene glycols can also be added to the premixes for dust binding.
  • the active substance-loaded resins can be present in the formulations alone or in a mixture with other active substances, mineral salts, trace elements, vitamins, protein substances, colorants, fats or flavorings.
  • the active substance-loaded ion exchange resins can be administered together with the feed.
  • the feed includes single feed of vegetable origin such as hay, beets, cereals, grain by-products, single feed of animal origin such as meat,
  • Fats, milk products, bone meal, fish products furthermore the feed materials such as vitamins, proteins, amino acids, e.g. DL-methionine, salts such as lime and table salt.
  • the feed also includes supplementary, finished and compound feed. These contain feed materials in a composition that provides a balanced diet with regard to energy and protein supply as well as the supply of vitamins,

Landscapes

  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
EP02743262A 2001-07-17 2002-07-04 Pharmazeutische zubereitungen enthaltend fluorochinolonbeladene ionentauscherharze Ceased EP1411894A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10134719A DE10134719A1 (de) 2001-07-17 2001-07-17 Pharmazeutische Zubereitungen enthaltend wirkstoffbeladene Ionentauscherharze
DE10134719 2001-07-17
PCT/EP2002/007417 WO2003007995A2 (de) 2001-07-17 2002-07-04 Pharmazeutische zubereitungen enthaltend fluorochinolonbeladene ionentauscherharze

Publications (1)

Publication Number Publication Date
EP1411894A2 true EP1411894A2 (de) 2004-04-28

Family

ID=7692081

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02743262A Ceased EP1411894A2 (de) 2001-07-17 2002-07-04 Pharmazeutische zubereitungen enthaltend fluorochinolonbeladene ionentauscherharze

Country Status (13)

Country Link
US (1) US20040247560A1 (https=)
EP (1) EP1411894A2 (https=)
JP (1) JP2005500332A (https=)
AR (1) AR034777A1 (https=)
AU (1) AU2002345086B2 (https=)
BR (1) BR0211149A (https=)
CA (1) CA2453616A1 (https=)
DE (1) DE10134719A1 (https=)
MX (1) MXPA04000332A (https=)
NO (1) NO20040205L (https=)
NZ (1) NZ530604A (https=)
WO (1) WO2003007995A2 (https=)
ZA (1) ZA200400269B (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010034853A1 (es) 2008-09-23 2010-04-01 Laboratorio Jaer, S.A. Utilización de exilitol o sus derivados para el enmascaramiento gustativo de quimioterapicos del grupo del ácido quinolon-o-naftiridoncarboxilico administrados en alimentos destinados a ganado porcino

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10224086A1 (de) * 2002-05-31 2003-12-11 Bayer Ag Pharmazeutische Zubereitungen zur oralen Anwendung enthaltend wirkstoffbeladene Ionentauscherharze sowie strukturviskose Gelbildner als Verdicker
DE102006049520A1 (de) 2006-10-20 2008-04-24 Bayer Healthcare Ag Verfahren zur Herstellung von Pradofloxacin
DE102012021559A1 (de) 2012-11-02 2014-05-08 Technische Universität Bergakademie Freiberg Verfahren zur Herstellung von submikronen makroporösen Ionenaustauschermaterialien durch mechansiche Zerkleinerung
US9669010B2 (en) 2012-12-06 2017-06-06 Bio Health Solutions, Llc Treatment for chronic kidney disease
DK2928461T3 (da) * 2012-12-06 2019-11-25 Bio Health Solutions Llc Behandling til kronisk nyresygdom
EP2808319A1 (en) * 2013-05-31 2014-12-03 Arevipharma GmbH 3-[3-(Dimethylamino)-1-ethyl-2-methylpropyl]phenol resin complex
CA3098060A1 (en) 2018-04-25 2019-10-31 Bayer Animal Health Gmbh Process for the hydrolysis of quinolone carboxylic esters

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA804914B (en) * 1979-08-29 1981-08-26 Rohm & Haas The production of powdered resin and the powdered resin so produced
DE3719764A1 (de) * 1987-06-13 1988-12-22 Bayer Ag Ionenaustauscherharze beladen mit chinoloncarbonsaeurederivaten, ihre herstellung und verwendung

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03007995A2 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010034853A1 (es) 2008-09-23 2010-04-01 Laboratorio Jaer, S.A. Utilización de exilitol o sus derivados para el enmascaramiento gustativo de quimioterapicos del grupo del ácido quinolon-o-naftiridoncarboxilico administrados en alimentos destinados a ganado porcino

Also Published As

Publication number Publication date
BR0211149A (pt) 2004-06-29
NZ530604A (en) 2006-09-29
CA2453616A1 (en) 2003-01-30
ZA200400269B (en) 2005-03-30
AU2002345086B2 (en) 2007-05-24
US20040247560A1 (en) 2004-12-09
DE10134719A1 (de) 2003-02-06
WO2003007995A2 (de) 2003-01-30
WO2003007995A3 (de) 2003-07-31
JP2005500332A (ja) 2005-01-06
MXPA04000332A (es) 2005-04-19
NO20040205L (no) 2004-01-16
AR034777A1 (es) 2004-03-17

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