WO2001052897A2 - Therapeutic anti-inflammatory and analgesic composition containing selective cox-2 inhibitors - Google Patents

Therapeutic anti-inflammatory and analgesic composition containing selective cox-2 inhibitors Download PDF

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Publication number
WO2001052897A2
WO2001052897A2 PCT/IN2001/000007 IN0100007W WO0152897A2 WO 2001052897 A2 WO2001052897 A2 WO 2001052897A2 IN 0100007 W IN0100007 W IN 0100007W WO 0152897 A2 WO0152897 A2 WO 0152897A2
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Prior art keywords
composition
topical
agent
inflammatory
percutaneous
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PCT/IN2001/000007
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English (en)
French (fr)
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WO2001052897A3 (en
Inventor
Amarjit Singh
Rajesh Jain
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Panacea Biotec Limited
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Priority to AU44515/01A priority Critical patent/AU4451501A/en
Publication of WO2001052897A2 publication Critical patent/WO2001052897A2/en
Publication of WO2001052897A3 publication Critical patent/WO2001052897A3/en

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    • 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
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • 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
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • 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
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • 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
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • 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
    • A61K9/12—Aerosols; Foams
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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

  • This invention relates to novel therapeutic anti-inflammatory and analgesic pharmaceutical compositions containing Selective COX- 2 inhibitors drugs for use transdermally and a process for the manufacture thereof.
  • COX- 2 inhibitor drugs such as Celecoxib and Rofecoxib are a highly hydrophobic drugs and consequently they are considered poor candidate for transdermal absorption. When applied to the skin, these are absorbed in very minute quantities or not absorbed at all.
  • a transdermal route for administration of anti-inflammatory agents offers various advantages over the oral route such a3 lower dosage, less toxicity/side effects, no G I irritation, no dose dumping in the body and it is more site specific (Chien YW: Novel Drug Delivery System, Marcel Dekker, New York, 1982).
  • COX cyclooxygenase
  • COX-2 activity is "ind ⁇ cible” and generally occurs in response to a specific stimulus to enhance inflammatory actions.
  • Current NSAIDs inhibit both COX-1 and COX-2, although the clinical benefit of NSAIDs appears to be associated with inhibition of COX-
  • COX-2 selective inhibitors have been developed. Current data would suggest that by inhibiting COX-2 action, these agents may have efficacy similar to that of standard NSA1D3 and that by not inhibiting COX-1 activity, they may have less toxicity than standard NSAIDs. Thus, these actions indicate that COX-2 selective inhibitors will have similar clinical efficacy to
  • Celecoxib is a known selective COX-2 inhibitor having analgesic and anti-inflammatory activity, but which has the drawback of having unfavourable chemical-physical characteristics; the main obstacle to the use of celecoxib in topical formulation is in fact its insolubility in water and, on the other hand, its poor solubility in the solvents/raw materials usually employed in such formulation.
  • the chemical structure of Celecoxib and Rofecoxib are given hereinbelow alongwith their chemical names:-
  • Celecoxib - p[5-p-Tolyl-3-(trifluoromethyl) pyrazol-1-yl) benzenesulfonamide.
  • Rofecoxib 4-[4-(methyl sulphonyl) phenyl]-3-phenyl-2(5H)-furanone.
  • the present invention provides a Novel Therapeutic Anti-inflammatory and Analgesic Pharmaceutical composition for topical use which comprises :
  • the said Percutaneous enhancing vehicle base comprises :
  • the percutaneous enhancing base comprises :
  • One or more vehicle/base 5% to 60% w/w.
  • One or more percutaneous enhancers can be used in compositions according to this invention.
  • One or more surfactants can be used in compositions according to this invention.
  • One or more gelling agents/thickening agents can be used in compositions according to this invention.
  • composition for topical use also comprises a neutralizing agent pH adjusting agent such as herein described in the range of 0.0%
  • the present invention it has been found that it is possible to deliver a highly hydrophobic drugs such as COX-2 inhibitor drugs to the site of action through a transdermal route.
  • the present invention involves the process of incorporation of COX- 2 inhibitor drugs in a formulation which can transport the drug through the skin barriers, in intact condition to the site of action.
  • the percutaneous enhancing base comprises :
  • One or more vehicle/base 5% to 60% w w.
  • the COX-2 inhibitor drugs are in the range of 0.2% to 20% w w.
  • the composition for topical use also comprises a Neutralising agent/ph adjusting agent as herein described in the range of 0.0% to 2.0%.
  • the novel Therapeutic Anti-Inflammatory and Analgesic Composition for topical use is prepared by the process which comprises the following steps :
  • step (c) The mixture obtained in step (a) is added to the homogenised mixture obtained in step (b) under stirring without vortex formation to avoid aeration.
  • the mixture is neutralised or its pH adjusted by addition of 0.0% to 5.0% of neutralizing agent or a pH adjusting agent to being the pH of the product on the acidic side, as herein described, with slow stirring resulting in the preparation of the desired Anti- inflammatory and Analgesic Composition.
  • Percutaneous enhancer any chemical can be used which interacts with the stratum corneum layer of the mammalian skin causing reversible change in its barrier
  • any known Percutaneous enhancer may be used preferably a C 12 - 24 mono or poly-unsaturated fatty acids such as vaccenic, cis- vaccenic, Linoleic, Linolenic, elaidic, oleic, petroselinic, erucic or nervonic acid or any of
  • any pharmaceutically acceptable hydrophilic or lipophilic surfactant or mixture thereof may be used, especially suitable for this purpose are the reaction products of natural or hydrogenated vegetable oils and ethylene glycol i.e. polyoxyethylene glycolated natural or hydrogenated vegetable oils, e.g. polyoxyethylene
  • glycolated natural or hydrogenated castor oils especially various tensides available
  • CREMOPHOR particularly CREMOPHOR RH 40 and
  • CREMOPHOR EL CREMOPHOR EL.
  • various surfactants available under the trade name NIKKOL e.g. NIKKOL HCO-60.
  • Polyoxyethlene-Sorbitan fatty acid esters e.g. mono and trilauryl, palmityl, stearyl and oleyl esters e.g. those available under the trade name TWEEN preferably TWEEN 40
  • Polyoxyethylene-polyoxypropylene block copolymers e.g. especially those available under the trade name POLOXAMER preferably POLOXAMER 188.
  • Polyoxyethylene fatty acid esters for example polyoxyethylene stearic acid esters, commercially available under the trade name MYRJ as well as polyoxyethylene fatty acid esters commercially available under the trade name CEIIOL HE;
  • Propylene glycol mono-and di-fatty acid esters such as propylene glycol dicaprylate, propylene glycol dilaurate, propylene glycol hydroxysterate, pripylene glycol isostearate, propylene glycol laurate, propylene glycol ricinoleater, propylene glycol stearate;
  • Suitable lipophilic surfactants include trans-esterification products of natural vegetable oil triglycerides and polyalkylene polyols. Preferred are products obtained by trans-esterification of 2 molar parts of natural vegetable oil triglycerides with one molar part of polyethylene glycol (e.g. having an average molecular weight of from 200 to
  • trans-estrification product Various forms of such trans-estrification product are commercially available under the trade name LABRAFIL, preferably LABRAFIL M 1944 CS;
  • Sorbitan fatty acid esters commercially available under the trade name SPAN including
  • any known such pharmaceutically acceptable agent may be used including synthetic or semi-synthetic polymeric materials, polyacrylate and polyacrylate co-polymeric resins e.g. polyacrylic acid and polyacrylic acid/methacrylic acid resins, commercially available under the trade name CARBOPOL, particularly CARBOPOL 934, 940 and 941 and EUDRAGIT, particularly EUDRAGIT E, L, S, RL,
  • CARBOPOL particularly CARBOPOL 934, 940 and 941
  • EUDRAGIT particularly EUDRAGIT E, L, S, RL
  • Cellulose and cellulose derivatives including alkyl celluloses e.g. methyl-, ethyl-, and propyl-celluloses; hydroxyalkyl-celluloses e.g. hydroxypropyl cellulose, hydroxypropyl alkylcellulose such as hydroxypropyl-methyl-cellulose, acylated celluloses e.g. cellulose-acetates, cellulose acetate phthalates and salts thereof such as sodium carboxymethyl cellulose;
  • Polyvinyl resins including polyvinylacetates and alcohols as well as other polymeric materials including alginates e.g. alginic acid and salts thereof e.g. sodium alginate and propylene glycol alginate.
  • alginates e.g. alginic acid and salts thereof e.g. sodium alginate and propylene glycol alginate.
  • neutralising pH adjusting agent any such conventional such agent may be used including sodium bicarbonate, sodium hydroxide, potassium hydroxide, borax, disodium hydrogen phosphate and sodium dihydrogen phosphate.
  • polar organic amines like diethylamine, diisopropanolamine, trithylamine and triethanolamine may be used, acidifying agents including hydrochloric acid, lactic acid, malic acid, tartaric acid
  • Lower (having C ⁇ s) alkanols particularly ethanol; water soluble macrogels like polyethylene glycol having an average molecular weight from 200 to 600: 1 , 2-propylene carbonate, pro ⁇ ane-1, 2-diol and 1, 2-propylene glycol; glycerol triacetate or (1 ,2,3,)-triacetin; lower ketones, particularly acetone and 1,2,3 - propanetriol may be incorporated. Water in varying concentration may be added to
  • Ci alkyl or tetra hydrofurfuryl di or partial ether of a low molecular weight mono or polyoxy-alkanediol particularly those available under the trade names TRANSCUTOL and GLYCOFUROL.
  • fatty acid triglycerides preferably medium chain fatty acid triglycerides; vegetable oils like coconut oil3, olive oil, castor oil and their derivatives; and ethyl oleate may be used.
  • base for the preparation of the said therapeutic composition in the form of an ointment, fatty acids, fats, oils and waxes of animal origin like bees wax, spermacetii, wool fat, waxes of vegetable origin or mineral origin like hard, soft and liquid paraffin
  • topical dosage forms are formulated suitably such that the resultant product is easy
  • propellants such as chlorofluoro carbons e.g. the Propellant 11 , Propellant 12, Propellant 114; Hydrocarbon propellants like n-butane, isobutane and propane; compressed gas propellants e.g. Nitrous oxide,
  • novel therapeutic composition according to the present invention may be used in the following forms :
  • Oil-irv-water or water-in-oil emulsion or micro-emulsion or cream 1.
  • Aerosol formulation for topical applications The therapeutic composition according to the present invention may be applied on the skin by utilising a physical form of energy like electrical energy or ultrasonic energy to effect better percutaneous absorption of the drug.
  • Step (a) Dimethylacetamide is mixed with ethyl alcohol and acetone at 30 ⁇ C. in a container with stirring. To the mixture obtained Celecoxib is added and stirred till
  • Step (b) Propylene glycol, polyethylene glycol 400 and water are mixed in homogenizer.
  • 1.5% w/w of carbopol 934 is added in small amounts at a time at room temperature and the speed of the homogenizer is kept at
  • Step ⁇ The mixture obtained in step (a) is added to the mixture obtained in step (b) under stirring without vortex formation to avoid aeration preferably under vacuum (25 mm of Hg).
  • the mixture obtained is neutralised by slow addition of diethylamine with slow stirring at a temperature of 25 ⁇ - 30 ⁇ C and under vacuum (25 mm of Hg) to affect
  • Cremophor RH 40 4.0 g Propylene glycol 38.0 g 7. Polyethylene glycol 400 48.8 g 8. Carbopol 934 4.0 g 9. Water 30.0 g
  • Step (b) Propylene glycol, polyethylene glycol 400 and water are mixed in homogenizer.
  • 1.5% w/w of carbopol 934 is added in small amounts at a time at room temperature and the speed of the homogenizer is kept at
  • Step ⁇ The mixture obtained in step (a) is added to the mixture obtained in step (b) under stirring without vortex formation to avoid aeration preferably under vacuum (25 mm of Hg).
  • the mixture obtained is neutralised by slow addition of diethylamine with slow stirring at a temperature of 25° - 30°C and under vacuum (25 mm of Hg) to affect
  • Celecoxib 1.0 g 2. Dimethyl formamide 10.0 g 3. Poloxamer 188 2.0 g 4. Ethyl alcohol 20.0 g 5. Propylene glycol 25.0 g 6. Polyethylene glycol 400 42.0 g 7. Hydroxypropylmethyl 1.0 g cellulose
  • Rofecoxib is dissolved in (2) with stirring and (3), (4), (5), (6), (7) and (8) are added to
  • Step 1 Mix 1 and 2 is a jacketted vessel.
  • Step 2 Mix ingredients 3 to 11 separately at 40 - 60°C
  • Step 3 Mix phases of step 1 and 2 using a homegenizer EXAMPLE 14
  • Step 1 Mix 1 and 2 is a jacketted vessel.
  • Step 2 Mix ingredients 3 to 11 separately at 40 - 60°C
  • Step 3 Mix phases of s tep 1 and 2 using a homegenizer

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Dermatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/IN2001/000007 2000-01-21 2001-01-19 Therapeutic anti-inflammatory and analgesic composition containing selective cox-2 inhibitors WO2001052897A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU44515/01A AU4451501A (en) 2000-01-21 2001-01-19 Therapeutic anti-inflammatory and analgesic composition containing selective cox-2 inhibitor drugs for use transdermally and a process for the manufacture thereof

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IN46DE2000 IN191512B (enrdf_load_stackoverflow) 2000-01-21 2000-01-21
IN46/DEL/2000 2000-01-21

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WO2001052897A3 WO2001052897A3 (en) 2002-03-14

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Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002002111A1 (de) * 2000-07-01 2002-01-10 Lts Lohmann Therapie-System Ag Dermales therapeutisches system enthaltend nichtsteroidale antiphlogistika mit selektiver cox-2-hemmung
WO2002096435A3 (en) * 2001-05-31 2003-05-01 Pharmacia Corp Skin-permeable composition comprising a selective cyclooxygenase-2 inhibitor a monohydric alcohol
WO2004026313A1 (en) * 2002-09-17 2004-04-01 Nippon Boehringer Ingelheim Co., Ltd. Pharmaceutical composition for topical delivery of meloxicam comprising an amine or amine as penetration enhancer.
WO2004047815A1 (en) * 2002-11-21 2004-06-10 Pharmacia Corporation Dermal delivery of a water-soluble selective cyclooxygenase-2 inhibitor, e.g. parecoxib and valdecoxib
WO2004047814A1 (en) * 2002-11-21 2004-06-10 Pharmacia Corporation Dermal delivery of a water-soluble selective cyclooxygenase-2 inhibitor, e.g. parecoxib, valdecoxib and benzopyran derivatives
WO2004047816A1 (en) * 2002-11-21 2004-06-10 Pharmacia Corporation Selective cyclooxygenase-2 inhibitor patch
WO2005044227A1 (en) * 2003-11-05 2005-05-19 Glenmark Pharmaceuticals Limited Topical pharmaceutical compositions
EP1315500A4 (en) * 2000-08-29 2006-05-31 Ranbaxy Lab Ltd PHARMACEUTICAL COMPOSITIONS FOR TOPICAL ADMINISTRATION OF CYCLOOXYGENASE-2 INHIBITORS
WO2008075993A1 (en) * 2006-12-19 2008-06-26 Ion Fulga The use of diethylamine as analgesic in pharmaceutical preparations
EP2266533A3 (en) * 2002-06-25 2011-12-14 Acrux DDS Pty Ltd Transdermal delivery rate control using amorphous pharmaceutical compositions
US8920820B2 (en) 2001-12-12 2014-12-30 Boehringer Ingelheim Vetmedica Gmbh Highly concentrated stable meloxicam solutions for needleless injection
US8992980B2 (en) 2002-10-25 2015-03-31 Boehringer Ingelheim Vetmedica Gmbh Water-soluble meloxicam granules
US9101529B2 (en) 2009-10-12 2015-08-11 Boehringer Ingelheim Vetmedica Gmbh Containers for compositions comprising meloxicam
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
WO2016015094A1 (en) * 2014-07-31 2016-02-04 Acrux Dds Pty Ltd Topical composition
EA023000B1 (ru) * 2012-10-25 2016-04-29 Закрытое Акционерное Общество "Фармфирма "Сотекс" Наружное средство для лечения болезней суставов и мягких тканей
US9795568B2 (en) 2010-05-05 2017-10-24 Boehringer Ingelheim Vetmedica Gmbh Low concentration meloxicam tablets
US9993557B2 (en) 2000-06-20 2018-06-12 Boehringer Ingelheim Vetmedica Gmbh Highly concentrated stable meloxicam solutions
JP2018516279A (ja) * 2015-05-29 2018-06-21 コーダドース・インコーポレーテッド 経口投与用のセレコキシブの液状配合物
EP3458031A4 (en) * 2016-05-16 2020-01-22 Delivra Inc. TRANSDERMAL FORMULATIONS FOR THE DELIVERY OF CELECOXIB AND THEIR USE IN THE TREATMENT OF CELCOXIB-SENSITIVE DISEASES AND CONDITIONS
US10548901B2 (en) 2004-02-23 2020-02-04 Boehringer Ingelheim Vetmedica Gmbh Meloxicam for the treatment of respiratory diseases in pigs
JP2023510354A (ja) * 2020-01-10 2023-03-13 ブリオリ バイオテック，エルエルシー ロフェコキシブを含有する外用組成物並びにそれを製造及び使用する方法

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HUP9601443A3 (en) * 1996-05-29 1999-03-29 Panacea Biotec Ltd Injectable analgetic pharmaceutical compositions for intramuscular use containing nimesulid, and process for producing them
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Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9993557B2 (en) 2000-06-20 2018-06-12 Boehringer Ingelheim Vetmedica Gmbh Highly concentrated stable meloxicam solutions
WO2002002111A1 (de) * 2000-07-01 2002-01-10 Lts Lohmann Therapie-System Ag Dermales therapeutisches system enthaltend nichtsteroidale antiphlogistika mit selektiver cox-2-hemmung
EP1315500A4 (en) * 2000-08-29 2006-05-31 Ranbaxy Lab Ltd PHARMACEUTICAL COMPOSITIONS FOR TOPICAL ADMINISTRATION OF CYCLOOXYGENASE-2 INHIBITORS
WO2002096435A3 (en) * 2001-05-31 2003-05-01 Pharmacia Corp Skin-permeable composition comprising a selective cyclooxygenase-2 inhibitor a monohydric alcohol
US10098891B2 (en) 2001-12-12 2018-10-16 Boehringer Ingelheim Vetmedica Gmbh Highly concentrated stable meloxicam solutions for needleless injection
US8920820B2 (en) 2001-12-12 2014-12-30 Boehringer Ingelheim Vetmedica Gmbh Highly concentrated stable meloxicam solutions for needleless injection
EP1534235B1 (en) * 2002-06-25 2016-07-27 Acrux DDS Pty Ltd Transdermal delivery rate control using amorphous pharmaceutical compositions
US8784878B2 (en) 2002-06-25 2014-07-22 Acrux DDS Pty Ltc. Transdermal delivery rate control using amorphous pharmaceutical compositions
EP2266533A3 (en) * 2002-06-25 2011-12-14 Acrux DDS Pty Ltd Transdermal delivery rate control using amorphous pharmaceutical compositions
US8357393B2 (en) 2002-06-25 2013-01-22 Acrux Dds Pty Ltd. Transdermal delivery rate control using amorphous pharmaceutical compositions
WO2004026313A1 (en) * 2002-09-17 2004-04-01 Nippon Boehringer Ingelheim Co., Ltd. Pharmaceutical composition for topical delivery of meloxicam comprising an amine or amine as penetration enhancer.
US9066955B2 (en) 2002-10-25 2015-06-30 Boehringer Ingelheim Vetmedica Gmbh Water-soluble meloxicam granules
US8992980B2 (en) 2002-10-25 2015-03-31 Boehringer Ingelheim Vetmedica Gmbh Water-soluble meloxicam granules
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WO2004047814A1 (en) * 2002-11-21 2004-06-10 Pharmacia Corporation Dermal delivery of a water-soluble selective cyclooxygenase-2 inhibitor, e.g. parecoxib, valdecoxib and benzopyran derivatives
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