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US20030119825A1 - Highly concentrated stable meloxicam solutions for needleless injection - Google Patents

Highly concentrated stable meloxicam solutions for needleless injection Download PDF

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Publication number
US20030119825A1
US20030119825A1 US10/314,586 US31458602A US2003119825A1 US 20030119825 A1 US20030119825 A1 US 20030119825A1 US 31458602 A US31458602 A US 31458602A US 2003119825 A1 US2003119825 A1 US 2003119825A1
Authority
US
United States
Prior art keywords
meloxicam
solution according
aqueous solution
meglumine
salt
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.)
Abandoned
Application number
US10/314,586
Other languages
English (en)
Inventor
Martin Folger
Stefan Henke
Bernhard Hassel
Bernd Zierenberg
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.)
Boehringer Ingelheim Vetmedica GmbH
Original Assignee
Boehringer Ingelheim Vetmedica 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 Boehringer Ingelheim Vetmedica GmbH filed Critical Boehringer Ingelheim Vetmedica GmbH
Assigned to BOEHRINGER INGELHEIM VETMEDICA GMBH reassignment BOEHRINGER INGELHEIM VETMEDICA GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FOLGER, MARTIN ANDREAS, HASSEL, BERNARD, HENKE, STEFAN, ZIERENBERG, BERND
Publication of US20030119825A1 publication Critical patent/US20030119825A1/en
Priority to US11/845,675 priority Critical patent/US20080132493A1/en
Priority to US14/078,962 priority patent/US10098891B2/en
Priority to US14/078,953 priority patent/US8920820B2/en
Priority to US14/526,973 priority patent/US9993485B2/en
Abandoned legal-status Critical Current

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Classifications

    • 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
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
    • 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
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
    • 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
    • A61K9/0021—Intradermal administration, e.g. through microneedle arrays, needleless injectors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the present invention relates to highly concentrated stable meloxicam solutions for intracutaneous or subcutaneous needleless injection for treating respiratory diseases and inflammation in mammals.
  • Meloxicam (4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide) is an active substance which belongs to the group of NSAIDs (non-steroidal-anti-inflammatory drugs).
  • NSAIDs non-steroidal-anti-inflammatory drugs.
  • Meloxicam and the sodium and meglumine salt thereof (N-methyl-D-glucamine salt) are described in EP-A-0 002 482.
  • EP-A-0 002 482 shows, inter alia, the example of a 0.2% injectable solution of meloxicam consisting of the meglumine salt of the active substance, sodium chloride and water.
  • EP-A-0 945 134 discloses the pH-dependent solubility characteristics of meloxicam and its salts, i.e. the sodium salt, the ammonium salt and the meglumine salt, in aqueous solution.
  • meloxicam is an active substance which does not dissolve readily in water.
  • the meloxicam salts, particularly the meglumine salt exhibit improved solubility as the pH increases between 4 and 10, as shown in Table 1 of EP-0 945 134.
  • a meloxicam salt e.g.
  • WO9959634 Al describes an eye drop solution containing 0.5% meloxicam but makes no reference to possible meloxicam concentrations over 1%.
  • a commercially available 0.5% meloxicam solution is used in small animals such as dogs, heifers and calves to treat respiratory diseases and inflammation, for example.
  • An active substance for needleless injection makes it possible for the animal keeper himself to administer a sterile solution to the animal.
  • the requirements imposed on an active substance solution for needleless injection include inter alia small injectable volumes, the possibility of weight-related dosage and maximum possible flexibility in the number of actuation processes per treatment unit. Accordingly, injection volumes of 50 ⁇ l per actuation, for example, are technically feasible.
  • a sterile solution may be transferred under aseptic conditions into a sterile cartridge which is then inserted in the metering system.
  • the method of administration by needle-free injection has a relevant effect on bioavailability, which will be greater than with intracutaneous or subcutaneous administration, as transcutaneous absorption also takes place with needle-free injection.
  • Organic solvents, solubilisers and water-soluble substances can only be used in certain concentrations for reasons of drug tolerance.
  • the problem of the present invention is to produce particle-free highly concentrated meloxicam solutions which are stable over long periods, which are suitable for needleless injection.
  • the invention relates, as described in claim 1, to aqueous cyclodextrin-free solutions of meloxicam for needle-free intracutaneous or subcutaneous administration which contain a pharmacologically acceptable meloxicam salt of an organic or inorganic base in a highly concentrated solution with 35 to 100 mg/ml of meloxicam together with suitable excipients.
  • Subclaims 2-14 describe advantageous further features of the invention.
  • the formulation according to the invention overcomes the problem arising from the prior art of providing a solution of the active substance meloxicam which is suitable for needleless injection, by permitting a high concentration of active substance in a particle-free solution which is stable over the long term, having the composition described hereinafter.
  • the formulation according to the invention may contain, as the meloxicam salt, the meglumine, sodium, potassium or ammonium salt, preferably the meloxicam meglumine salt.
  • the solubilisers used may be, for example polyethyleneglycols, polyoxyethylene-polyoxypropylene copolymers (e.g.
  • polyethyleneglycols particularly preferred are polyethyleneglycols, glycofurol and polyoxyethylene-polyoxypropylene-copolymers, but especially polyethyleneglycols (e.g. Macrogol 300) and polyoxyethylene-polyoxypropylene copolymers (e.g. Poloxamer 188).
  • the preservatives used may be, for example, ethanol, benzoic acid and the sodium or potassium salts thereof, sorbic acid and the sodium or potassium salts thereof, chlorobutanol, benzyl alcohol, phenylethanol, methyl, ethyl, propyl or butyl-p-hydroxybenzoates, phenol, m-cresol, p-chloro-m-cresol or benzalkonium chloride.
  • ethanol benzoic acid and the sodium or potassium salts thereof, sorbic acid and the sodium or potassium salts thereof, chlorobutanol, benzylalcohol, phenylethanol and methyl, ethyl, propyl or butyl p-hydroxybenzoates, but preferably ethanol, benzoic acid and the sodium or potassium salts thereof, sorbic acid and the sodium or potassium salts thereof, but especially ethanol.
  • the buffer system used to achieve a pH of between 8 and 10 may be, for example, glycine, a mixture of glycine and HCl, a mixture of glycine and sodium hydroxide solution, and the sodium and potassium salts thereof, a mixture of potassium hydrogen phthalate and hydrochloric acid, a mixture of potassium hydrogen phthalate and sodium hydroxide solution or a mixture of glutamic acid and glutamate.
  • Glycine, a mixture of glycine and HCl and a mixture of glycine/sodium hydroxide solution, especially glycine are particularly preferred.
  • excipients are citric acid, lecithin, gluconic acid, tartaric acid, phosphoric acid and EDTA or the alkali metal salts thereof, preferably tartaric acid and EDTA or the alkali metal salts thereof, particularly disodium EDTA.
  • One embodiment of the invention contains, in addition to the meglumine or sodium salt of the meloxicam, polyethyleneglycols, glycofurol and/or polyoxyethylene-polyoxypropylene copolymers, but particularly polyethyleneglycols (e.g. Macrogol 300) and/or polyoxyethylene-polyoxypropylene copolymers (e.g.
  • Poloxamer 188) as solubiliser, ethanol, benzoic acid and the sodium or potassium salts thereof or sorbic acid and the sodium or potassium salts thereof, but particularly ethanol, as preservative, and glycine, a mixture of glycine/HCl or a mixture of glycine/sodium hydroxide solution, but preferably glycine, as buffer and disodium EDTA as an additional excipient.
  • the formulation according to the invention may contain meloxicam in a concentration of 35-100 mg/ml, preferably 40-80 mg/ml, preferably 45-70 mg/ml, particularly preferably 50-60 mg/ml, especially 55 mg/ml.
  • the meglumine concentration may be between 30 and 50 mg/ml, preferably 35-45 mg/ml, preferably 38-42 mg/ml, especially about 40 mg/ml.
  • the possible sodium, potassium and ammonium concentrations are calculated accordingly.
  • the concentration of the solubilisers may be in the range from 20-200 mg/ml, preferably 30-150 mg/ml, preferably 40-130 mg/ml, more preferably 5Q-120 mg/ml, especially 70-100 mg/ml.
  • the concentration of the preservative ethanol may be in the range from 100-200 mg/ml, preferably 120-180 mg/ml, more preferably about 150 mg/ml.
  • the concentration of the preservatives benzoic acid and the sodium or potassium salts thereof, sorbic acid and the sodium or potassium salts thereof, chlorobutanol, benzyl alcohol, phenylethanol, phenol, m-cresol and p-chloro-m-cresol may be in the range from 0.5-50 mg/ml, preferably 1-10 mg/ml, more preferably 3-5 mg/ml.
  • the concentration of the preservatives benzalkonium chloride, phenylmercury nitrate and methyl-, ethyl-, propyl- or butyl-p-hydroxybenzoates may be in the range from 0.01-4 mg/ml, preferably 0.02-3 mg/ml, more preferably 0.1-0.5 mg/ml.
  • the concentration of the buffer substances may be between 4 and 138 mg/ml, preferably between 5 and 20 mg/ml, more preferably between 8 and 10 mg/ml.
  • the concentration of the other excipients mentioned above, i.e. EDTA, citric acid, lecithin, gluconic acid, tartaric acid and phosphoric acid or the salts thereof may be in the range from 0.2-3 mg/ml, preferably 0.3-2.5 mg/ml, preferably 0.5-2 mg/ml, most preferably 0.6-1.5 mg/ml, and in particular 0.7-1.0 mg/ml.
  • Meglumine and meloxicam may be used in a molar ratio of between 9:8 and 12:8, preferably in a molar ratio of 11:8, but especially in a molar ratio of 10:8.
  • meloxicam and the other excipient, particularly disodium EDTA may be present in a weight ratio of between 100:1 and 35:1, preferably between 80:1 and 40:1, preferably between 70:1 and 45:1, more preferably between 60:1 and 50:1, most preferably between 58:1 and 52:1, in particular about 55:1.
  • the formulation according to the invention may have a shelf-life after opening of 28 days or more.
  • the shelf-life of the solution in the sealed original packaging may be 1 month or more, in particular between 1 month and 24 months, but at least between 1 month and 18 months, preferably between 1 month and 12 months, more preferably between 1 month and 9 months, most preferably between 1 month and 6 months, particularly between 1 month and 3 months.
  • the formulation according to the invention should have a pH of between 8 and 10, preferably between 8.5 and 9, more preferably a pH between 8.7 and 8.9, particularly 8.8.
  • the formulation according to the invention is suitable for treating pain, inflammation, fever, acute mastitis, diarrhoea, lameness, oncological indications, problems with the locomotor apparatus, and respiratory complaints in animals, preferably acute mastitis, diarrhoea, lameness, problems with the locomotor apparatus and respiratory complaints, especially acute mastitis, diarrhoea, lameness, problems with the locomotor apparatus and respiratory complaints, most preferably respiratory complaints and oncological indications.
  • the treatment may be given in conjunction with antibiotic therapy.
  • the formulation according to the invention is suitable for treating animals, preferably mammals, more particularly domestic pets, working animals or farm animals.
  • the formulation according to the invention is suitable for treating animals, preferably animals up to 500 kg, particularly domestic pets from 1 kg upwards, more preferably from 2 to 70 kg, most preferably 5 to 60 kg, or large animals up to 750 kg, preferably 50 kg to 500 kg, most preferably 100 to 400 kg.
  • the dosage of the formulation according to the invention should correspond to 0.1 to 1.0 mg of active substance per kg of bodyweight, preferably 0.4 to 0.8 mg/kg of bodyweight, more preferably 0.5 to 0.7 mg/kg of bodyweight, particularly preferably 0.6 mg/kg of bodyweight.
  • the formulation according to the invention may be prepared using the methods of preparing aqueous liquid formulations known from the literature.
  • the appropriate excipients may be added to a meloxicam salt solution.
  • aqueous liquid formulations which will allow sealing under inert gas and/or final sterilisation by autoclaving in the finished container may be used as a packaging material for the formulation according to the invention.
  • Such materials include for example ampoules or glass vials, particularly glass vials, e.g. 50 ml or 100 ml glass vials of glass Type I (according to Pharm. Eur/USP) in conjunction with rubber stoppers made of ethylenepropylenenorbornene terpolymer (EPDM) and aluminium caps.
  • Vials made of plastics, particularly COC (Cyclic Olefin Copolymer), and other types of rubber stoppers are also suitable.
  • 4% meloxicam solution Ingredients: g/100 ml Meloxicam 4.0 Meglumine 2.8 Macrogol 300* 1 15.0 Poloxamer 188* 2 5.0 Ethanol 15.6 Glycine 0.5 EDTA-Na 0.1 1M HCl q.s. ad pH 8.8 1M NaOH q.s. ad pH 8.8 Water for injections ad 100 ml
  • dogs may be treated by needle-free injection with a 4% meloxicam solution according to the invention in a metered volume of 50 ⁇ l per spray jet in a precise dosage related to body weight.
  • a dog weighing 10 kg can be treated with a dose of 0.2 mg of meloxicam per kg of body weight with precisely one spray jet. Therapeutic accuracy is ensured in this case in steps of 10 kg.
  • meloxicam 4 g are dissolved in 50 ml of an aqueous meglumine solution (1.4 g/50 ml) at 90° C.
  • the other excipients are added one after another to the solution according to the recipe given above.
  • the pH is then adjusted to 8.8 using 1 M hydrochloric acid and 1 M sodium hydroxide solution. Water is added to the solution until a volume of 100 ml is obtained.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pulmonology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US10/314,586 2001-12-12 2002-12-09 Highly concentrated stable meloxicam solutions for needleless injection Abandoned US20030119825A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US11/845,675 US20080132493A1 (en) 2001-12-12 2007-08-27 Highly concentrated stable meloxicam solutions for needleless injection
US14/078,962 US10098891B2 (en) 2001-12-12 2013-11-13 Highly concentrated stable meloxicam solutions for needleless injection
US14/078,953 US8920820B2 (en) 2001-12-12 2013-11-13 Highly concentrated stable meloxicam solutions for needleless injection
US14/526,973 US9993485B2 (en) 2001-12-12 2014-10-29 Highly concentrated stable meloxicam solutions for needleless injection

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10161077.7 2001-12-12
DE10161077A DE10161077A1 (de) 2001-12-12 2001-12-12 Hochkonzentrierte stabile Meloxicamlösungen zur nadellosen Injektion

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US11/845,675 Continuation US20080132493A1 (en) 2001-12-12 2007-08-27 Highly concentrated stable meloxicam solutions for needleless injection

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US20030119825A1 true US20030119825A1 (en) 2003-06-26

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ID=7708961

Family Applications (5)

Application Number Title Priority Date Filing Date
US10/314,586 Abandoned US20030119825A1 (en) 2001-12-12 2002-12-09 Highly concentrated stable meloxicam solutions for needleless injection
US11/845,675 Abandoned US20080132493A1 (en) 2001-12-12 2007-08-27 Highly concentrated stable meloxicam solutions for needleless injection
US14/078,953 Expired - Lifetime US8920820B2 (en) 2001-12-12 2013-11-13 Highly concentrated stable meloxicam solutions for needleless injection
US14/078,962 Expired - Lifetime US10098891B2 (en) 2001-12-12 2013-11-13 Highly concentrated stable meloxicam solutions for needleless injection
US14/526,973 Expired - Lifetime US9993485B2 (en) 2001-12-12 2014-10-29 Highly concentrated stable meloxicam solutions for needleless injection

Family Applications After (4)

Application Number Title Priority Date Filing Date
US11/845,675 Abandoned US20080132493A1 (en) 2001-12-12 2007-08-27 Highly concentrated stable meloxicam solutions for needleless injection
US14/078,953 Expired - Lifetime US8920820B2 (en) 2001-12-12 2013-11-13 Highly concentrated stable meloxicam solutions for needleless injection
US14/078,962 Expired - Lifetime US10098891B2 (en) 2001-12-12 2013-11-13 Highly concentrated stable meloxicam solutions for needleless injection
US14/526,973 Expired - Lifetime US9993485B2 (en) 2001-12-12 2014-10-29 Highly concentrated stable meloxicam solutions for needleless injection

Country Status (17)

Country Link
US (5) US20030119825A1 (es)
EP (1) EP1455782B1 (es)
JP (1) JP5348818B2 (es)
AR (1) AR037789A1 (es)
AT (1) ATE357232T1 (es)
AU (1) AU2002361035A1 (es)
CA (1) CA2469588C (es)
CY (1) CY1106637T1 (es)
DE (2) DE10161077A1 (es)
DK (1) DK1455782T3 (es)
ES (1) ES2283634T3 (es)
PE (1) PE20030575A1 (es)
PT (1) PT1455782E (es)
SI (1) SI1455782T1 (es)
TW (1) TW200302720A (es)
UY (1) UY27575A1 (es)
WO (1) WO2003049733A1 (es)

Cited By (35)

* Cited by examiner, † Cited by third party
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US20040180092A1 (en) * 2002-10-25 2004-09-16 Boehringer Ingelheim Vetmedica Gmbh Water-soluble meloxicam granules
US20040229038A1 (en) * 2003-03-03 2004-11-18 Elan Pharma International Ltd. Nanoparticulate meloxicam formulations
WO2005021041A1 (en) * 2003-08-30 2005-03-10 Archimedes Development Limited Intranasal formulations of meloxicam
US20050187213A1 (en) * 2004-02-23 2005-08-25 Boehringer Ingelheim Vetmedica Gmbh Meloxicam for the treatment of respiratory diseases in pigs
US20050187212A1 (en) * 2002-09-17 2005-08-25 Nippon Boehringer Ingelheim Co., Ltd. Pharmaceutical composition for topical delivery of meloxicam
US20050245510A1 (en) * 2004-04-29 2005-11-03 Boehringer Ingelheim Vetmedica Gmbh Use of meloxicam formulations in veterinary medicine
US20050277634A1 (en) * 2004-05-19 2005-12-15 Boehringer Ingelheim Vetmedica Gmbh Liquid composition for veterinary medicine and process for the preparation and use thereof
US20050288280A1 (en) * 2004-06-23 2005-12-29 Boehringer Ingelheim Vetmedica Gmbh Meloxicam in veterinary medicine
US20060079516A1 (en) * 2000-06-20 2006-04-13 Boehringer Ingelheim Vetmedica Gmbh Highly concentrated stable meloxicam solutions
KR100620239B1 (ko) * 2004-01-05 2006-09-13 신일제약주식회사 용해도 및 안정성이 향상된 경구투여용 멜록시캄 고형제조성물
US20060211982A1 (en) * 2002-12-20 2006-09-21 Steven Prestrelski Intracutaneous injection
US20070077296A1 (en) * 2005-09-30 2007-04-05 Folger Martin A Pharmaceutical Preparation containing Meloxicam
US20070092539A1 (en) * 2003-07-10 2007-04-26 Arturo Jimenez-Bayardo Method of preparing an aqueous meloxicam solution and aqueous solution thus produced
US20080132493A1 (en) * 2001-12-12 2008-06-05 Martin Andreas Folger Highly concentrated stable meloxicam solutions for needleless injection
US20090143762A1 (en) * 2007-11-29 2009-06-04 Alltranz Inc. Methods and Compositions for Enhancing the Viability Of Microneedle Pores
EP2191820A1 (en) 2008-12-01 2010-06-02 Sanovel Ilac Sanayi ve Ticaret A.S. Pharmaceutical formulations of meloxicam
US20100297252A1 (en) * 2003-03-03 2010-11-25 Elan Pharma International Ltd. Nanoparticulate meloxicam formulations
US20100316725A1 (en) * 2009-05-27 2010-12-16 Elan Pharma International Ltd. Reduction of flake-like aggregation in nanoparticulate active agent compositions
US20110083985A1 (en) * 2009-10-12 2011-04-14 Boehringer Ingelheim Vetmedica Gmbh Containers for compositions comprising meloxicam
US20110086097A1 (en) * 2008-06-13 2011-04-14 Daniel Kaufmann Manufacture process for the preparation of an iron containing phosphate adsorbent
CN102846558A (zh) * 2012-09-20 2013-01-02 浙江亚太药业股份有限公司 一种氯诺昔康冻干制剂及其制备方法
US8697644B2 (en) 2011-03-10 2014-04-15 Xeris Pharmaceuticals, Inc. Stable formulations for parenteral injection of peptide drugs
US9018162B2 (en) 2013-02-06 2015-04-28 Xeris Pharmaceuticals, Inc. Methods for rapidly treating severe hypoglycemia
US9090571B2 (en) 2010-09-30 2015-07-28 Toyama Chemical Co., Ltd. Meglumine salt of 6-fluoro-3-hydroxy-2-pyrazine carboxamide
US9125805B2 (en) 2012-06-27 2015-09-08 Xeris Pharmaceuticals, Inc. Stable formulations for parenteral injection of small molecule drugs
US9138479B2 (en) 2011-10-31 2015-09-22 Xeris Pharmaceuticals, Inc. Formulations for the treatment of diabetes
US9149480B2 (en) 2010-03-03 2015-10-06 Boehringer Ingeleheim Vetmedica GmbH Use of meloxicam for the long-term treatment of musculoskeletal disorders in cats
US9649364B2 (en) 2015-09-25 2017-05-16 Xeris Pharmaceuticals, Inc. Methods for producing stable therapeutic formulations in aprotic polar solvents
US9687527B2 (en) 2010-07-19 2017-06-27 The Regents Of The University Of Colorado, A Body Corporate Stable glucagon formulations for the treatment of hypoglycemia
US9795568B2 (en) 2010-05-05 2017-10-24 Boehringer Ingelheim Vetmedica Gmbh Low concentration meloxicam tablets
WO2019214715A1 (zh) * 2018-05-11 2019-11-14 南京清普生物科技有限公司 一种美洛昔康组合物、制剂及其制备方法与应用
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AR037789A1 (es) 2004-12-01
US20140113893A1 (en) 2014-04-24
US20080132493A1 (en) 2008-06-05
US20150051198A1 (en) 2015-02-19
US10098891B2 (en) 2018-10-16
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ATE357232T1 (de) 2007-04-15
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