EP1993549A1 - Formulations de médicaments contenant des fluoroquinolones - Google Patents

Formulations de médicaments contenant des fluoroquinolones

Info

Publication number
EP1993549A1
EP1993549A1 EP07711642A EP07711642A EP1993549A1 EP 1993549 A1 EP1993549 A1 EP 1993549A1 EP 07711642 A EP07711642 A EP 07711642A EP 07711642 A EP07711642 A EP 07711642A EP 1993549 A1 EP1993549 A1 EP 1993549A1
Authority
EP
European Patent Office
Prior art keywords
sodium
acid
formulation according
pradofloxacin
pharmaceutical formulation
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Withdrawn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
EP07711642A
Other languages
German (de)
English (en)
Inventor
Iris Heep
Kristine Fraatz
Hans-Jürgen HAMANN
Markus Edingloh
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 Intellectual Property GmbH
Original Assignee
Bayer Animal Health GmbH
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 Animal Health GmbH filed Critical Bayer Animal Health GmbH
Publication of EP1993549A1 publication Critical patent/EP1993549A1/fr
Withdrawn legal-status Critical Current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
    • A61K9/08—Solutions
    • 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
    • A61K47/02—Inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • 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
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • 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
    • A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
    • 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
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers

Definitions

  • the invention relates to pharmaceutical formulations in liquid form containing fluroquinolones and antioxidant sulfur compounds.
  • the formulations are particularly suitable for parenteral applications and are u. a. through good compatibility.
  • the chemical stability of solutions may e.g. be increased by using antioxidants. In this case, the oxidative degradation of an ingredient can be prevented. This is also common and especially for injection solutions.
  • Common antioxidants here include u.a. the sulfites.
  • DE-A-19500784, EP-A-0187315 or EP-A-1121933 describe injection solutions with sulphites. Eye drops are also provided as solutions with sulfites, as described in EP-A-0804267.
  • DE-A-2364470 describes the use of sulphites which have a
  • Compatibility for example in cattle, may not necessarily be compatible with e.g. Cats or dogs are closed (WO 01/81358). To ensure broad applicability, it therefore makes sense to improve the local tolerability of injection solutions so that they can also be used in sensitive animal species.
  • freeze-dried products are cumbersome to handle in practice and often only have a shelf life of the reconstituted solution of a maximum of 4 weeks after onset, or must be discarded directly due to the possible particle formation.
  • the advantage is therefore a ready to use solution as an injection solution, also known as "ready to use - formulation”.
  • the subject of the invention is therefore:
  • a pharmaceutical formulation in liquid form comprising:
  • Fluoroquinolones include compounds disclosed in the following documents: US 4,670,444 (Bayer AG), US 4,472,405 (Riker Labs), US 4,730,000 (Abbott), US 4,861
  • Moxifloxacin Moxifloxacin, norfloxacin, ofloxacin, orbifloxacin, pefloxacin, pipemidic acid, temafloxacin, toufloxacin, sarafloxacin, sparfloxacin.
  • fluoroquinolones are those of the formula (I) or (IT): in which
  • X is hydrogen, halogen, C M -alkyl, C M -alkoxy, NH 2 ,
  • R 4 represents optionally substituted by hydroxy or methoxy straight-chain or branched C 1 -C 4 -alkyl, cyclopropyl, acyl having 1 to 3 C-atoms,
  • R 5 is hydrogen, methyl, phenyl, thienyl or pyridyl
  • R 6 is hydrogen or C M -alkyl
  • R 7 is hydrogen or C M -alkyl
  • R 8 is hydrogen or C M -alkyl
  • R 1 is an alkyl radical having 1 to 3 carbon atoms, cyclopropyl, 2-fluoroethyl, methoxy, 4-
  • R 2 is hydrogen or optionally methoxy or 2-methoxyethoxy-substituted alkyl having 1 to 6 carbon atoms and cyclohexyl, benzyl, 2-oxopropyl, phenacyl, ethoxycarbonylmethyl, pivaloyloxymethyl,
  • R 3 is hydrogen, methyl or ethyl
  • R! represents optionally halogen-substituted Cj-C3-alkyl or cyclopropyl
  • R 2 is hydrogen or Ci. 4- alkyl,
  • R 4 represents optionally substituted by hydroxy straight-chain or branched C iC 3 -alkyl, oxalkyl having 1 to 4 C-atoms,
  • R 5 is hydrogen, methyl or phenyl
  • R 6 is hydrogen
  • R 7 is hydrogen or methyl
  • R 8 is hydrogen
  • R! represents cyclopropyl
  • R 2 is hydrogen, methyl or ethyl
  • R 4 is methyl, optionally substituted by hydroxy ethyl
  • R 5 is hydrogen or methyl
  • R 6 is hydrogen
  • R 7 is hydrogen or methyl
  • R 8 is hydrogen
  • Marbofloxacin may be mentioned as a preferred example of a fluoroquinolone of the formula (II):
  • fluoroquinolones which may be mentioned are the compounds described in WO 97/31001, in particular 8-cyano-1-cyclopropyl-7 - ((1S, 6S) -2,8-diazabicyclo [4.3.0] nonan-8-yl) 6-fluoro, 4-dihydro-4-oxo-3-quinolinecarboxylic acid (pradofloxacin) having the formula
  • Enrofloxacin 1-Cyc! O -propyl-7- (4-ethyl-1-piperazinyl) -6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid is furthermore particularly preferably employed
  • Optically active fluoroquinolones may be in the form of their racemates or in enantiomeric forms. Both the pure enantiomers and mixtures thereof can be used according to the invention.
  • Suitable salts are pharmaceutically usable acid addition salts and basic salts.
  • Suitable pharmaceutically acceptable salts are the salts of hydrochloric acid, sulfuric acid, acetic acid, glycolic acid, lactic acid, succinic acid, citric acid, tartaric acid, methane. sulfonic acid, 4-toluenesulfonic acid, galacturonic acid, gluconic acid, embonic acid, glutamic acid or aspartic acid.
  • the compounds according to the invention can be bound to acidic or basic ion exchangers.
  • Suitable pharmaceutically usable basic salts are the alkali metal salts, for example the sodium or potassium salts, the alkaline earth metal salts, for example the magnesium or calcium salts; the zinc salts, the silver salts and the guanidinium salts.
  • Hydrates are understood as meaning both the hydrates of the fluoroquinolones themselves and the hydrates of their salts.
  • An example is pradofloxacin, which forms a stable trihydrate (see WO 2005/097789).
  • Fluoroquinolones may possibly form different crystal modifications as a solid.
  • compositions of the present invention are those modifications which have corresponding solubility properties.
  • the fluoroquinolone is typically used in an amount for animals with a body weight up to about 80 kg of 0.1 to 15%, preferably 0.5 to 15% and particularly preferably 1 to 15%. In animals with a body weight from about 80 kg, the fluoroquinolone is typically used in a proportion of from 1 to 30%, preferably 3 to 25% and particularly preferably 4 to 20%. The percentages are given as M / V.
  • Antioxidative sulfur compounds are, for example: sulfites (sodium sulfite, potassium sulfite), bisulfates (such as, for example, sodium metabisulfite, potassium metabisulfite, potassium pyrosulfite, sodium pyrosulfite, acetonitrile metabisulfite, acetonitrile bisulfite), thiosulfates (such as, for example, potassium thiosulfate,
  • Sodium thiosulfate as well as organic sulfur compounds (such as sodium formaldehyde sulfoxylate, thiourea, thiosorbitol, cysteine hydrochloride, cystine, cysteine, acetylcysteine, glutathione, cysteamine, methionine, thioglycerol, thioglycolic acid, thiolactic acid).
  • organic sulfur compounds such as sodium formaldehyde sulfoxylate, thiourea, thiosorbitol, cysteine hydrochloride, cystine, cysteine, acetylcysteine, glutathione, cysteamine, methionine, thioglycerol, thioglycolic acid, thiolactic acid).
  • the antioxidant sulfur compounds are usually used in concentrations of 0.05 to 10%, preferably from 0.1 to 8% and particularly preferably from 0.5 to 5%.
  • the liquid formulations may contain other substances which improve the local tolerance when applied.
  • examples include: radical scavengers or antioxidants such as vitamin E, water-soluble vitamin E esters or vitamin C, butylhydroxyanisole or butylhydroxytoluene.
  • Complexing agents such as, for example, sodium EDTA (ethylenediaminetetraacetic acid), polyvinylpyrrolidone or cyclodextrins, of which in particular hydroxypropyl-.beta.-cyclodextrin or sulfobutyl ether .beta.-cyclodextrin, dexpanthenol, salts of Fatty acids such as sodium caprylate, salts of polyvalent cations eg: the alkaline earth metals (Me 2+ or Me 3+ ) and especially magnesium in its salt forms, amino acids and especially arginine or lysine, poloxamers, poloxamines, cosolvents such as n-butanol,
  • Substances which improve the compatibility are usually contained in concentrations of 0.05 to 10%, preferably of 0.1 to 8% and particularly preferably 0.5 to 5%. The percentages are given as M / V.
  • Substances which can prevent particle formation are e.g. Poloxamers, lecithins, polyvinylpyrrolidones, cosolvents, antioxidants, complexing agents or even quaternary ammonium compounds such. Benzethonium chloride or benzalkonium chloride.
  • Substances which improve stability, e.g. can avoid particle formation are usually used in concentrations of 0.001 to 10%, preferably 0.005 to 6% and more preferably 0.001 to 3%. The percentages are given as M / V.
  • the liquid formulation may contain water or water-miscible substances.
  • examples which may be mentioned are glycerol, propylene glycol, polyethylene glycols, compatible alcohols such as ethanol, benzyl alcohol or n-butanol, ethyl lactate, ethyl acetate, triacetin, N-methylpyrrolidone, propylene carbonate, propylene glycol, glycofurol, dimethylacetamide, 2-pyrrolidone,
  • Isopropylidene glycerol, or glycerol formal It is also possible to use mixtures of different solvents. Preference is given to water-based formulations in which, of course, further solvents and co-solvents may be present.
  • the liquid formulation can also contain oils in the form of an emulsion in addition to water or water-miscible substances.
  • oils include the vegetable, animal and synthetic oils such as cottonseed oil, sesame oil, soybean oil, medium-chain triglycerides of a chain length of Ci 2 -Ci 8 , propylene glycol octanoate decanoate or paraffin called.
  • the solvency is usually in concentrations of 99.8 to 72% or 98.9 to 55%, preferably 99.4 to 81% or 96.9 to 67% and particularly preferably 98.8 to 87% or 94.5 to 77% used.
  • the percentages are given as M / V.
  • the pH of the liquid formulations is usually 2-11, preferably 3-8 and more preferably 4-8.
  • the medicaments may also contain co-solvents, preferably when the formulations contain water. These are usually used in proportions of 1 to 10 wt .-%, preferably from 3 to 8%.
  • cosolvents are: pharmaceutically acceptable alcohols, dimethyl sulfoxide, ethyl lactate, ethyl acetate, triacetin, N-methylpyrrolidone, propylene carbonate, propylene glycol, glycofurol, dimethylacetamide, 2-pyrrolidone, isopropylideneglycerol, glycerol formal, glycerol and polyethylene glycols.
  • Kosolvenz are particularly suitable pharmaceutically acceptable alcohols, such as. As ethanol, benzyl alcohol or n-butanol. Mixtures of the abovementioned solvents can also be used as cosolvents.
  • Preservatives may be included in the liquid formulation, e.g. aliphatic
  • Alcohols such as benzyl alcohol, ethanol, n-butanol, phenol, cresols, chlorobutanol, para-hydroxybenzoic acid esters (in particular the methyl and propyl esters), salts or the free acids of the carboxylic acids, such as sorbic acid, benzoic acid, lactic acid or propionic acid, benzalkonium chloride, benzethonium chloride or cetylpyridinium chloride.
  • carboxylic acids such as sorbic acid, benzoic acid, lactic acid or propionic acid, benzalkonium chloride, benzethonium chloride or cetylpyridinium chloride.
  • the medicaments according to the invention may contain further customary pharmaceutically acceptable additives and auxiliaries. As examples may be mentioned
  • antioxidants such as phenols (tocopherols, as well as vitamin E and vitamin E TPGS (d-alpha-tocopheryl polyethylene glycol lOOO succinate)), butylhydroxyanisole, butylhydroxytoluene, octyl and dodecyl gallate), organic acids (ascorbic acid, citric acid .
  • Wetting agents such as, for example, fatty acid salts, fatty alkyl sulfates, fatty alkyl sulfonates, linear alkylbenzenesulfonates, fatty alkyl polyethylene glycol ether sulfates, fatty alkyl polyethylene glycol ethers, alkylphenol polyethylene glycol ethers, alkyl polyglycosides, fatty acid N-methylglucamides, polysorbates, sorbitan fatty acid esters and poloxamers.
  • fatty acid salts such as, for example, fatty acid salts, fatty alkyl sulfates, fatty alkyl sulfonates, linear alkylbenzenesulfonates, fatty alkyl polyethylene glycol ether sulfates, fatty alkyl polyethylene glycol ethers, alkylphenol polyethylene glycol ethers, alkyl polyglycosides, fatty acid N-methylglucamides, polysorbates,
  • substances for isotonization e.g. Sodium chloride, glucose or glycerin.
  • the formulations according to the invention may contain further pharmaceutical active ingredients.
  • the fluoroquinolones can also be used in combination, for example, with analgesics, in particular the so-called NSAIDs (nonsteroidal, anti-inflammatory substances) are used.
  • NSAEDs nonsteroidal, anti-inflammatory substances
  • Such NSAEDs may be, for example: meloxicam, flunixin, ketoprofen, carprofen, metamizole or (acetyl) salicylic acid.
  • the medicaments according to the invention can be prepared by dispersing the fluoroquinolone in the solvent after the antioxidative sulfur compound, and also adding further substances to improve the compatibility and, if appropriate, to avoid particle formation.
  • Kosolventien and other ingredients such. Preservatives may already be added to the solvent or added later.
  • cosolvents, preservatives, substances which influence the compatibility or particle formation can also first be dissolved in the solvent and subsequently the fluoroquinolone can be added first.
  • the antioxidant sulfur compound can be dispersed with or after the fluoroquinolone.
  • the pharmaceutical preparations according to the invention are generally suitable for use in humans and animals. They are preferably used in animal husbandry and animal breeding in livestock, breeding, zoo, laboratory, experimental and hobby animals.
  • the livestock and breeding animals include mammals such as e.g. Cattle, Horses, Sheep, Pigs,
  • Laboratory and experimental animals include mice, rats, guinea pigs, golden hamsters, dogs and cats.
  • the hobby animals include rabbits, hamsters, guinea pigs, mice, horses, reptiles, corresponding birds, dogs and cats.
  • fish are called, namely useful, breeding, aquarium and ornamental fish of all ages, living in fresh and salt water.
  • the preparations according to the invention are preferably used in hobby animals such as horses, cats and dogs. In particular, they are suitable for use in cats and dogs.
  • Examples of preferred farm animals are beef, sheep, pork, goat and chicken. Particularly preferred farm animals are beef and pork.
  • the application can be both prophylactic and therapeutic.
  • the formulations described herein can be delivered in various ways to the target organism (human or animal). They can be administered, for example, parenterally, in particular by injection (eg subcutaneously, intramuscularly, intravenously, intramammary, intraperitoneally), dermally, orally, rectally, vaginally or nasally, with parenteral administration-in particular by injection-being preferred.
  • the formulations are preferably added as solutions, suspensions or emulsions.
  • the medicaments according to the invention are distinguished by good stability and good solubility of the active ingredient. Furthermore, they have good compatibility and suitable serum kinetics in animals, in particular after parenteral administration.
  • the formulations of the following examples are prepared by mixing or dissolving the indicated starting materials in Aqua per injections.
  • the pH of the solutions can be adjusted by adding acids or bases.
  • the solutions for injection are sterile filtered and transferred into suitable containers.
  • Pradofloxacin can be used as anhydrate or as
  • Trihydrate are used; the numerical values are calculated respectively for the anhydrate.
  • pradofloxacin 3.0 g of pradofloxacin, 0.1 g of poloxamer, 0.2 g of sodium disulfite, 3 g of n-butanol, 2.7 g of sodium chloride are dissolved in about 80 g of aqua per injection, the pH is checked and optionally 1, 6 g of 1N sodium hydroxide adjusted to pH 7.4. It is then adjusted to the final weight of 100 ml with the remaining Aqua per injection.
  • pradofloxacin trihydrate, calculated as pure pradofloxacin
  • the remaining weight per injection is set to the final weight of 100 ml.
  • 80 g of Aqua per injection are mixed with 0.5 g of sodium bisulfite, 3 g of n-butanol, 2.6 g of sodium chloride and 0.1 g of poloxamer. It dissolves 2 pradofloxacin (trihydrate, calculated as pure pradofloxacin). If necessary, it is adjusted to a pH of 7.4 with approx. 2.4 g sodium hydroxide and the remaining weight per injection is adjusted to the final weight of 100 ml.
  • the formulation has an influence on the serum pharmacokinetic (PK) profile. Different formulations show significant differences in the serum concentration-time curve. For quinolones, fast absorption, high peak concentration, and long elimination phase curves are preferred. Table 2 below lists various formulations and shows their influence on the PK profile.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne des formulations de médicaments sous forme liquide contenant des fluoroquinolones et des composés de soufre antioxydants. Ces formulations sont particulièrement adaptées à des applications par voie parentérale et elles se caractérisent entre autres par une bonne tolérance.
EP07711642A 2006-03-08 2007-02-23 Formulations de médicaments contenant des fluoroquinolones Withdrawn EP1993549A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006010642A DE102006010642A1 (de) 2006-03-08 2006-03-08 Arzneimittelformulierungen, enthaltend Fluorchinolone
PCT/EP2007/001568 WO2007101560A1 (fr) 2006-03-08 2007-02-23 Formulations de médicaments contenant des fluoroquinolones

Publications (1)

Publication Number Publication Date
EP1993549A1 true EP1993549A1 (fr) 2008-11-26

Family

ID=37907814

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07711642A Withdrawn EP1993549A1 (fr) 2006-03-08 2007-02-23 Formulations de médicaments contenant des fluoroquinolones

Country Status (17)

Country Link
US (2) US20090163484A1 (fr)
EP (1) EP1993549A1 (fr)
JP (1) JP2009529014A (fr)
KR (1) KR20080110599A (fr)
CN (1) CN101400351A (fr)
AU (1) AU2007222676A1 (fr)
BR (1) BRPI0708692A2 (fr)
CA (1) CA2644981C (fr)
CR (1) CR10274A (fr)
DE (1) DE102006010642A1 (fr)
EC (1) ECSP088722A (fr)
MX (1) MX2008011489A (fr)
NZ (1) NZ571047A (fr)
RU (1) RU2008139633A (fr)
SV (1) SV2008003018A (fr)
WO (1) WO2007101560A1 (fr)
ZA (1) ZA200807486B (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010069493A1 (fr) * 2008-12-18 2010-06-24 Bayer Animal Health Gmbh Combinaison améliorée de principes actifs contenant un antibiotique et un médicament anti-inflammatoire non stéroïdien (nsaid)
EP2332916A3 (fr) 2009-11-19 2011-08-03 Krka Tovarna Zdravil, D.D., Novo Mesto Procede de la preparation du marbofloxacin et produits intermediares
GB2480276A (en) * 2010-05-11 2011-11-16 Michael Hilary Burke Process for the preparation of an aqueous injectable enrofloxacin antimicrobial formulation
CN101810569B (zh) * 2010-05-22 2011-09-21 鼎正动物药业（天津）有限公司 一种恩诺沙星注射液及其制备方法
GB201021186D0 (en) 2010-12-14 2011-01-26 Novabiotics Ltd Composition
KR101473979B1 (ko) * 2013-01-18 2014-12-26 한국썸벧(주) 마보플록사신을 포함하는 약제학적 조성물
GR1008168B (el) * 2013-03-14 2014-04-08 "Φαρματεν Α.Β.Ε.Ε.", Παρεντερικο σκευασμα αντιβακτηριακου παραγοντα φθοριοκινολονης και μεθοδος για την παρασκευη αυτου
JP6358868B2 (ja) * 2014-06-17 2018-07-18 Ｄｓファーマアニマルヘルス株式会社 オルビフロキサシンを含有する製剤組成物
MX2019009572A (es) * 2017-02-13 2019-10-02 Bayer Animal Health Gmbh Composicion liquida que contiene pradofloxacina.

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008025380A1 (fr) * 2006-03-08 2008-03-06 Bayer Animal Health Gmbh Médicament contenant de la fluoroquinolone

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5746986A (en) * 1980-09-02 1982-03-17 Dai Ichi Seiyaku Co Ltd Pyrido(1,2,3-de)(1,4)benzoxazine derivative
US4670444B1 (en) * 1980-09-03 1999-02-09 Bayer Ag and-naphthyridine-3-carboxylic acids and antibacte7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-rial agents containing these compounds
US4472405A (en) * 1982-11-12 1984-09-18 Riker Laboratories, Inc. Antimicrobial 6,7-dihydro-5,8-dimethyl-9 fluoro-1-oxo-1H, 5H-benzo (ij) quinolizine-2-carboxylic acid and derivatives
US4730000A (en) * 1984-04-09 1988-03-08 Abbott Laboratories Quinoline antibacterial compounds
DE3517709A1 (de) * 1985-01-05 1986-07-10 Bayer Ag Basische zubereitungen von chinoloncarbonsaeuren
AT392789B (de) * 1985-01-23 1991-06-10 Toyama Chemical Co Ltd Verfahren zur herstellung von 1-substituierten aryl-1,4-dihydro-4-oxonaphthyridinderivaten
US4614572A (en) * 1985-07-08 1986-09-30 The Dow Chemical Company Liquid phase chlorination of chlorinated methanes
IN166416B (fr) * 1985-09-18 1990-05-05 Pfizer
KR930001302B1 (ko) * 1990-12-07 1993-02-25 주식회사 중외제약 시플로플록사신의 주사용 조성물 및 그 제조방법
DE19500784A1 (de) * 1995-01-13 1996-07-18 Bayer Ag Enrofloxacin-Injektions- oder Infusionslösungen
SK284412B6 (sk) * 1995-12-21 2005-03-04 Pfizer Inc. Vodný farmaceutický roztok vhodný na injekčné podávanie hostiteľovi
DE19729879C2 (de) * 1997-07-11 1999-07-08 Mann Gerhard Chem Pharm Fab Lagerstabile ophthalmische Zusammensetzungen, umfassend Diclofenac und Ofloxacin
US6482799B1 (en) * 1999-05-25 2002-11-19 The Regents Of The University Of California Self-preserving multipurpose ophthalmic solutions incorporating a polypeptide antimicrobial
EP1121933A1 (fr) * 2000-02-02 2001-08-08 Pfizer Products Inc. Compositions prémélangées injectables d'alatrofloxacin
BR0110382A (pt) * 2000-04-27 2003-06-24 Pfizer Prod Inc Utilização de composições antibióticas azalida para o tratamento ou prevenção de uma infecção causada por bactérias ou protozoários em mamìferos
US7083802B2 (en) * 2003-07-31 2006-08-01 Advanced Ocular Systems Limited Treatment of ocular disease
DE102004015981A1 (de) * 2004-04-01 2005-10-20 Bayer Healthcare Ag Neue kirstalline Form von 8-Cyan-1-cyclopropyl-7-(1S,6S-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäure
JP4792032B2 (ja) * 2004-08-13 2011-10-12 シェーリング−プラウ・リミテッド 抗生物質、トリアゾールおよびコルチコステロイドを含む薬学的処方物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008025380A1 (fr) * 2006-03-08 2008-03-06 Bayer Animal Health Gmbh Médicament contenant de la fluoroquinolone

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO2007101560A1 *

Also Published As

Publication number Publication date
SV2008003018A (es) 2009-11-26
DE102006010642A1 (de) 2007-09-27
US20090163484A1 (en) 2009-06-25
ZA200807486B (en) 2009-11-25
US20150080387A1 (en) 2015-03-19
JP2009529014A (ja) 2009-08-13
RU2008139633A (ru) 2010-04-20
KR20080110599A (ko) 2008-12-18
AU2007222676A1 (en) 2007-09-13
BRPI0708692A2 (pt) 2011-06-14
CR10274A (es) 2009-03-18
ECSP088722A (es) 2008-11-27
WO2007101560A1 (fr) 2007-09-13
NZ571047A (en) 2012-03-30
CA2644981A1 (fr) 2007-09-13
MX2008011489A (es) 2008-11-14
CN101400351A (zh) 2009-04-01
CA2644981C (fr) 2015-04-28

Similar Documents

Publication Publication Date Title
EP2340809B1 (fr) Formulations de médicaments contenant des fluoroquinolones
EP2121024B1 (fr) Stabilisation de vitamine b12
EP1993549A1 (fr) Formulations de médicaments contenant des fluoroquinolones
EP1608335B1 (fr) Systeme de liberation controlee contenant de l'acetate isobutyrate de saccharose
WO2010069493A1 (fr) Combinaison améliorée de principes actifs contenant un antibiotique et un médicament anti-inflammatoire non stéroïdien (nsaid)

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20081008

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

17Q First examination report despatched

Effective date: 20090819

DAX Request for extension of the european patent (deleted)
RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BAYER INTELLECTUAL PROPERTY GMBH

RIC1 Information provided on ipc code assigned before grant

Ipc: A61K 9/08 20060101AFI20150910BHEP

Ipc: A61K 47/16 20060101ALI20150910BHEP

Ipc: A61K 47/20 20060101ALI20150910BHEP

Ipc: A61K 31/4709 20060101ALI20150910BHEP

Ipc: A61K 47/10 20060101ALI20150910BHEP

Ipc: A61P 31/04 20060101ALI20150910BHEP

Ipc: A61K 47/02 20060101ALI20150910BHEP

Ipc: A61K 47/34 20060101ALI20150910BHEP

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

INTG Intention to grant announced

Effective date: 20151020

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20160301