WO2004080382A2 - Novel compositions containing fentanyl - Google Patents
Novel compositions containing fentanyl Download PDFInfo
- Publication number
- WO2004080382A2 WO2004080382A2 PCT/GB2004/001037 GB2004001037W WO2004080382A2 WO 2004080382 A2 WO2004080382 A2 WO 2004080382A2 GB 2004001037 W GB2004001037 W GB 2004001037W WO 2004080382 A2 WO2004080382 A2 WO 2004080382A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formulation
- formulation according
- fentanyl
- spray
- polar organic
- Prior art date
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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4468—Non condensed piperidines, e.g. piperocaine having a nitrogen directly attached in position 4, e.g. clebopride, fentanyl
-
- 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
- A61P23/00—Anaesthetics
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- 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
Definitions
- This invention relates to formulations of fentanyl, especially pump spray formulations suitable for sublingual delivery.
- Fentanyl is a narcotic alkaloid, which has been used for many years as an anaesthetic and an analgesic, especially in the treatment of moderate to severe pain. Whilst undoubtedly effective for pain relief, and especially in the treatment of pain which is refractive to other treatments, there are a number of issues of clinical management associated with the use of fentanyl in therapy.
- fentanyl Foremost amongst these issues is the potential for serious side effects with fentanyl. It has a much higher potency than commonly known narcotics and therefore it is necessary to ensure that it is being used within the established therapeutically effective range and to monitor patients for evidence of self medication at greater than the recommended amount. Overdosage with fentanyl can lead to a number of undesirable and indeed life-threatening side effects, predominantly hypoventilation and respiratory depression.
- a number of routes of administration of a medicament can be associated with rapid onset of action.
- International Patent Application O90/07333 (Riker Labs) described aerosol formulations of fentanyl, which are adapted for inhalation.
- Riker's formulations suffer disadvantages such as their use of hydrofluorocarbon propellants and delivery effected by metered dose inhalers.
- the disadvantages include high velocity which results in 'bounce back' on administration to the front of the mouth, cold sensations on administration, the risk of inhalation and for the latter, careful co-ordination of breath and actuation by the patient.
- the pharmacology of the medication may be unpredictable due to poor bioavailability following oral administration or may be characterised by a bi-phasic profile (fast initial onset as a result of the inhaled dose and a slower, late effect due to oral absorption of fentanyl).
- manufacture of the bulk formulation involves the preparation of large quantities of pressurised volatile propellant containing a potent narcotic analgesic. Accordingly the precautions required to ensure safe manufacture are onerous and expensive.
- W095/31182 (Aradigm Corp) describes solution formulations of fentanyl in aerosol propellants intended for administration to patients by the pulmonary route.
- WOOl/97780 (Pharmasol Ltd) describes solution formulations of fentanyl free base in propellants, typically HFA134a, for sublingual aerosol administration.
- WO00/47203 (MQS Inc) describes formulations of fentanyl citrate for intra-oral administration employing oral absorption enhancers.
- compositions subhngually are known.
- tablets or liquids may be held under the tongue prior to swallowing.
- spray delivery is preferred as it does not involve holding the composition under the tongue for an extended period of time as, for example, with a lozenge and it reduces the amount of material which is swallowed (and may enter the blood stream in a delayed manner via the gastrointestinal tract).
- compositions for example a fentanyl lozenge cause increased salivation, which facilitates the unwanted swallowing of drug substance.
- Spray delivery having low volume and ability to target the sublingual mucosa, largely mitigates this.
- No propellant free spray formulations of fentanyl which are adapted for subhngual administration have yet been described.
- composition being a partially pressurised liquid spray formulation, which comprises:
- the formulations of the invention are preferably administered subhngually as a spray.
- the formulations are well tolerated when administered to the sensitive subhngual mucosa and the subhngual spray administration will result in rapid onset of the therapeutic effect of the fentanyl.
- the formulations of the present invention are also preferably free of any propellant.
- the formulations are partially pressurised and are free of propellants such as volatile chlorofluorocarbons (e.g. propellant 12), volatile hydrofluoroalkanes (e.g. 1,1,1,2-tetrafluoroethane and 1,1,1,2,3,3,3-heptafluoro-n- propane) and volatile alkanes (e.g. propane, butane) and other substances which have significant vapour pressure at ambient temperature and pressure.
- propellants such as volatile chlorofluorocarbons (e.g. propellant 12), volatile hydrofluoroalkanes (e.g. 1,1,1,2-tetrafluoroethane and 1,1,1,2,3,3,3-heptafluoro-n- propane) and volatile alkanes (e.g. propane, butane) and other substances which have significant vapour pressure at ambient temperature and pressure.
- the formulation is a solution, rather than a suspension. Whilst it is possible to spray a suspension, the fact that most suspensions settle means that the amount of active agent included in the dispensed dose will be variable and this can be highly undesirable. Although the effect of the settling of the suspension can be reduced to an extent by shaking the composition prior to spraying, some suspensions can settle very rapidly, so that there is still potential for variation of active agent content between doses.
- formulations of the present invention are characterised by good long-term physical and chemical stability.
- Fentanyl may be employed in the form of a physiologically acceptable salt, which is soluble in water together with a polar organic solvent.
- suitable salts include hydrochloride, chloride, sulphate, tartrate and citrate.
- fentanyl is employed as the free base.
- the fentanyl or physiologically acceptable salt thereof will be employed in the formulation at a concentration of O.lmg/ml to lOmg/ml, preferably 0.5mg/ml to 4.4mg/ml (where weight is expressed as weight of fentanyl free base).
- polar organic solvents that may be used to enhance the solubility of fentanyl, or the physiologically acceptable salt thereof in the water, include: lower alcohols (e.g. C 2 . 4 alcohols) such as ethanol; lower polyols (e.g. C 2 . 4 polyols) such as glycerol and propylene glycol; and polyethylene glycols such as PEG200 and PEG400.
- the preferred polar organic solvent is ethanol.
- the formulation does not include ethanol. Indeed, the formulation may be substantially free of any alcohol, or completely free of alcohol.
- the carrier used is preferably a polyol.
- the preferred polyols include propylene glycol and glycerol.
- the concentration of polar organic solvent is in the range preferably of between 6 and 50%, more preferably 20-45% especially 35-42%.
- the water meets the USP (US Pharmacopoeia), EP (European Pharmacopoeia) "Purified Water” standards.
- the water in the formulation is present in the form of an aqueous buffer.
- the buffer is preferably adapted to stabilise the pH of the formulation at pH 7.4 to 8.5, preferably at pH 8.0 to 8.5, more preferably at 8.1 to 8.3, or around 8.2.
- pH 7.4 to 8.5 preferably at pH 7.4 to 8.5
- pH 8.0 to 8.5 more preferably at 8.1 to 8.3, or around 8.2.
- Example buffer systems include sodium acetate/acetic acid, ammonium acetate/disodium edetate, boric acid/sodium hydroxide, orthophosphoric acid/sodium hydroxide, sodium hydrogen carbonate/sodium carbonate, disodium hydrogen orthophosphate/citric acid (taken from the British Pharmacopoeia).
- a citrate buffer e.g. a buffer comprising citric acid, sodium citrate and sodium hydroxide.
- the concentration of the aqueous component (water or more preferably aqueous buffer) of the formulation of the present invention is preferably 50-94%, more preferably 55-80%, and especially 58-65%.
- Sweeteners for example vanilla, pineapple extract, menthol, saccharin and sodium saccharin.
- Moisturising agents to improve patient comfort and overcome the drying tendency of ethanol and other polar organic solvents
- pineapple extract for example pineapple extract, lanolin, polypropylene glycol, and polyethylene glycol.
- Mucoadherents in order to increase residency time on the mucosa, for example carboxyvinyl polymers, chitosans, polyacrylic acid, gelatin and polyvinyl pyrrohdone.
- Preservatives to improve long term resistance to microbial contamination), for example ethanol, sodium metabisulphite, benzalkonium chloride and Nipas.
- Antioxidants for example Alkyl Gallates, Butylated Hydroxyanisole, Butylated Hydroxytoluene, Nordihydroguaiaretic acid, Tocopherols, Ascorbic acid and Sodium metabisulphite.
- Anionic surfactants for example Magnesium Stearate, Sodium Cetostearyl sulphate, Sodium Lauryl sulphate, Sulphated caster oil, Sodium oleate, Sodium stearyl Fumarate and Sodium Tetradecyl Sulphate.
- Nonionic surfactants for example Glyceryl Monostearate, Macrogol Cetostearyl Ethers, Poloxamers, Polyoxyl Stearates, Polysorbates, Sorbitan Esters, Sucrose Esters, Tyloxapol, Propylene Glycol Monostearate, Quillaia, Polyoxyl Caster Oils, Nonoxinols, Lecithins and derivatives, Oleic acid and derivatives, Oleyl alcohol and derivatives.
- Nonionic surfactants for example Glyceryl Monostearate, Macrogol Cetostearyl Ethers, Poloxamers, Polyoxyl Stearates, Polysorbates, Sorbitan Esters, Sucrose Esters, Tyloxapol, Propylene Glycol Monostearate, Quillaia, Polyoxyl Caster Oils, Nonoxinols, Lecithins and derivatives, Oleic acid and derivatives, Oleyl alcohol and derivatives.
- Foaming agents for example Alginic Acid and salts, Propylene Glycol Alginate, Sodium Lauryl sulphate, Sodium Cetostearyl sulphate, carbomers, Hydroxyethylcellulose
- Suitable moisturising agents include, for example, the polar organic solvents such as glycols, especially propylene glycol, and the liquid polyethylene glycols, glycerol, methylcellulose, hypromellose, hydroxypropylcellulose, and many other substituted celluloses.
- a versatile component which improves the acceptabihty and other properties of the formulation, is menthol.
- Menthol, as well as flavouring the formulation, has moisturising effect. It may also have effect as a penetration enhancer.
- menthol is employed in a concentration range of 0.25% to 7.5%.
- menthol is compatible with fentanyl in a spray formulation unlike peppermint oil (of which menthol is one component), which causes fentanyl to degrade.
- the formulation contains a sweetener.
- the preferred sweetener is saccharin or a physiologically acceptable salt thereof such as saccharin sodium.
- concentration of sodium saccharin or physiologically acceptable salt thereof is around 0.1-0.5%, e.g. around 0.28%.
- the formulation contains saccharin.
- saccharin Surprisingly, we have found that the longer-term stability of formulations containing saccharin is better than the stability of those containing saccharin sodium. It has been discovered that it is not generally necessary to include a preservative in the formulation when ethanol is present due to its preservative qualities.
- Formulations of the invention are useful in analgesia and in the treatment of pain.
- formulations according to the first aspect of the invention are provided for use in the treatment of moderate to severe pain.
- the use of the formulations according to the invention in the manufacture of a medicament for analgesia or for the treatment of pain is provided.
- a therapeutically effective amount of a formulation for the treatment of pain according to the invention is used.
- Formulations according to the invention are preferably packaged as a bulk solution containing multiple doses in a pump spray system comprising a sealed container fitted with a metering pump.
- a sealed container containing a plurality of doses of a formulation according to the invention.
- the container will preferably contain between 20 to 200 doses.
- Example containers are those made out of plastics, glass and metal (e.g. aluminium) however glass containers are preferred. Glass containers have the advantage that the contents of the container can be seen (i.e. it is possible to determine visually when the contents are about to run out). Furthermore glass containers are less susceptible to tampering, which is an important consideration for narcotic substances.
- single or multiple use devices comprising a single or multiple dose of the formulation of the invention is envisaged.
- the glass container will be coated on the exterior with a suitable moulded film of plastic to protect against shattering.
- the film may be of polypropylene.
- the material may be coloured and contain a UV absorber.
- the interior of the containers can be coated to enhance stability of the product.
- Coatings include polymers and lacquers but also silicone dioxide can be used to line the inside of the container with an unreactive coating.
- Another aspect of the invention is a metered dose dispensing system comprising a sealed container containing a formulation of the invention fitted with a metering pump, an actuator and a channelling device.
- the metered dose dispensing system is preferably adapted for subhngual administration.
- Suitable metering pumps include those adapted for dispensation with the container in the upright or inverted orientation.
- the metering chamber is adapted for dispensation with the container in the upright orientation since this facilitates administration under the tongue. Accordingly the metering chamber will be in communication with the bulk formulation by means of a dip-tube.
- Example metering pumps are those manufactured by Valois and illustrated in International Patent Application No. WO01/66089.
- the metering pump is preferably a non-venting type with a dip tube.
- Such non- venting metering pumps may have, for example, a lOO ⁇ l metering chamber capacity.
- the materials of construction include polypropylene and polyethylene.
- Suitable sealing materials, e.g. thermoplastic crimp gaskets suitable for the purpose will be employed.
- a suitable aluminium ferrule purposely designed for crimping on to glass containers may suitably be employed.
- Suitable grade stainless steel springs will preferably be adopted.
- the actuator will be designed to deliver a subhngually effective dose.
- the package may be further enhanced by the fitting of a lock-out system to promote compliance by patients.
- a patient is treated by administration subhnguaUy of 1 to 4 actuations, e.g. 1 or 2 actuations from the spray pump.
- subhnguaUy of 1 to 4 actuations, e.g. 1 or 2 actuations from the spray pump.
- Another advantage of subhngual spray delivery is the ability to easily titrate patients by 1 or 2 doses as required by a single actuation. This is not the case with other forms of drug dehvery (patches, lozenges, tablets, suppositories).
- Figure 1 is a flow-chart showing the first stage of the method of preparing a formulation comprising 400 ⁇ g fentanyl.
- Figure 2 is a flow-chart showing the second stage of the method.
- formulations of the invention may be prepared by analogous methods, or methods known to a skilled person.
- Weight percentage values given herein are expressed as w/w.
- formulations and products of the invention have better physical and chemical stability, are more environmentally friendly, are more conveniently or safely administered to patients, are more conveniently or safely manufactured, are more economical to manufacture, or have other advantages relative to prior art formulations and products.
- Citrate buffer when employed contained: Citric acid 2.0 %
- the target dose is 400 ⁇ g per actuation.
- the target dose is 400 ⁇ g per actuation of lOO ⁇ l.
- the target dose is 400 ⁇ g per actuation of lOO ⁇ l.
- the target dose is 400 ⁇ g per actuation of lOO ⁇ l.
- the target dose is 200 ⁇ g per actuation of lOO ⁇ l.
- the example formulations may be packaged into a suitable coated glass container and fitted with a suitable non-venting metered dose pump.
- An actuator suitable for subhngual dehvery may be fitted.
- Example 1 The formulation of Example 1 was subjected to the following tests. Units were placed on stabihty storage at 5°C, 25°C/60% RH, 30°C/65% RH and 40°C/75% RH. For each test 3 replicates were assessed.
- Example 2 The formulation of Example 2 was subjected to the same tests, with the following results:
- Condition A 2-8°C, ambient humidity Condition B: 25°C, 60% relative humidity Condition C: 30°C, 60% relative humidity Condition D: 40°C, 75% relative humidity
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NZ541781A NZ541781A (en) | 2003-03-11 | 2004-03-11 | Novel compositions containing fentanyl |
EP04719527A EP1608372A2 (en) | 2003-03-11 | 2004-03-11 | Compositions containing fentanyl |
BRPI0408209-5A BRPI0408209A (en) | 2003-03-11 | 2004-03-11 | new compositions |
CN2004800051154A CN1784228B (en) | 2003-03-11 | 2004-03-11 | Novel compositions |
CA002516338A CA2516338A1 (en) | 2003-03-11 | 2004-03-11 | Novel compositions containing fentanyl |
AU2004218876A AU2004218876B2 (en) | 2003-03-11 | 2004-03-11 | Novel compositions containing fentanyl |
MXPA05009602A MXPA05009602A (en) | 2003-03-11 | 2004-03-11 | Novel compositions containing fentanyl. |
JP2006500257A JP2006519770A (en) | 2003-03-11 | 2004-03-11 | New composition |
NO20054172A NO20054172L (en) | 2003-03-11 | 2005-09-07 | New mixtures |
US11/224,383 US20060062812A1 (en) | 2003-03-11 | 2005-09-12 | Novel compositions |
HK05112165.9A HK1084012A1 (en) | 2003-03-11 | 2005-12-30 | Compositions containing fentanyl |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0305579.5 | 2003-03-11 | ||
GBGB0305579.5A GB0305579D0 (en) | 2003-03-11 | 2003-03-11 | Pharmaceutical compositions |
GB0328023.7 | 2003-12-03 | ||
GB0328023A GB2399286A (en) | 2003-03-11 | 2003-12-03 | Sub-lingual fentanyl formulation |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/224,383 Continuation-In-Part US20060062812A1 (en) | 2003-03-11 | 2005-09-12 | Novel compositions |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2004080382A2 true WO2004080382A2 (en) | 2004-09-23 |
WO2004080382A3 WO2004080382A3 (en) | 2005-03-24 |
Family
ID=32992592
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2004/001037 WO2004080382A2 (en) | 2003-03-11 | 2004-03-11 | Novel compositions containing fentanyl |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP1608372A2 (en) |
JP (1) | JP2006519770A (en) |
KR (1) | KR20050115276A (en) |
AU (1) | AU2004218876B2 (en) |
BR (1) | BRPI0408209A (en) |
CA (1) | CA2516338A1 (en) |
MX (1) | MXPA05009602A (en) |
NO (1) | NO20054172L (en) |
NZ (1) | NZ541781A (en) |
WO (1) | WO2004080382A2 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007007059A1 (en) | 2005-07-08 | 2007-01-18 | Sosei R & D Ltd. | Fentanyl formulation containing an essential oil |
JP2008530233A (en) * | 2005-02-17 | 2008-08-07 | ベルセラ ファーマシューティカルズ | Transmucosal administration of pharmaceutical compositions for treating and preventing disorders in animals |
EP1976521A2 (en) * | 2006-01-25 | 2008-10-08 | Insys Therapeutics, Inc. | Sublingual fentanyl spray |
WO2011077169A3 (en) * | 2009-12-24 | 2012-03-15 | Norwich Pharma Technologies Limited | Pharmaceutical preparation comprising sufentanil |
US8486973B2 (en) | 2007-08-02 | 2013-07-16 | Insys Therapeutics, Inc. | Sublingual fentanyl spray |
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WO2000016751A1 (en) * | 1998-09-24 | 2000-03-30 | Diabact Ab | Fentanyl composition for the treatment of acute pain |
WO2000047203A1 (en) * | 1999-02-12 | 2000-08-17 | Mqs, Inc. | Formulation and system for intra-oral delivery of pharmaceutical agents |
WO2002011778A1 (en) * | 2000-05-10 | 2002-02-14 | University Of Kentucky Research Foundation | System and method for intranasal administration of opioids |
WO2002051380A1 (en) * | 2000-12-22 | 2002-07-04 | Audit Institute For Medical Services And Quality Assurance Gmbh | Novel pharmaceutical composition consisting of water-soluble or poorly water-soluble active substances |
US20030035831A1 (en) * | 1998-12-21 | 2003-02-20 | Pankaj Modi | Pharmaceutical compositions for buccal delivery of pain relief medications |
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WO1999016417A1 (en) * | 1997-10-01 | 1999-04-08 | Flemington Pharmaceutical Corporation | Buccal, polar and non-polar spray or capsule |
-
2004
- 2004-03-11 BR BRPI0408209-5A patent/BRPI0408209A/en not_active IP Right Cessation
- 2004-03-11 KR KR1020057016853A patent/KR20050115276A/en not_active Application Discontinuation
- 2004-03-11 MX MXPA05009602A patent/MXPA05009602A/en not_active Application Discontinuation
- 2004-03-11 EP EP04719527A patent/EP1608372A2/en not_active Withdrawn
- 2004-03-11 AU AU2004218876A patent/AU2004218876B2/en not_active Ceased
- 2004-03-11 JP JP2006500257A patent/JP2006519770A/en active Pending
- 2004-03-11 WO PCT/GB2004/001037 patent/WO2004080382A2/en active IP Right Grant
- 2004-03-11 NZ NZ541781A patent/NZ541781A/en unknown
- 2004-03-11 CA CA002516338A patent/CA2516338A1/en not_active Abandoned
-
2005
- 2005-09-07 NO NO20054172A patent/NO20054172L/en not_active Application Discontinuation
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US5958379A (en) * | 1994-09-30 | 1999-09-28 | Mika Pharma Gesellschaft Fuer Die Entwicklung Und Vermarktung Pharmazeutischer Producte Mbh | Pharmaceutical composition |
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WO2000016751A1 (en) * | 1998-09-24 | 2000-03-30 | Diabact Ab | Fentanyl composition for the treatment of acute pain |
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WO2000047203A1 (en) * | 1999-02-12 | 2000-08-17 | Mqs, Inc. | Formulation and system for intra-oral delivery of pharmaceutical agents |
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Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008530233A (en) * | 2005-02-17 | 2008-08-07 | ベルセラ ファーマシューティカルズ | Transmucosal administration of pharmaceutical compositions for treating and preventing disorders in animals |
US8940271B2 (en) | 2005-02-17 | 2015-01-27 | Abbott Laboratories | Transmucosal administration of drug compositions for treating and preventing disorders in animals |
WO2007007059A1 (en) | 2005-07-08 | 2007-01-18 | Sosei R & D Ltd. | Fentanyl formulation containing an essential oil |
JP2009500387A (en) * | 2005-07-08 | 2009-01-08 | ソーセイ アールアンドディ リミテッド | Fentanyl formulation containing essential oil |
JP2009528272A (en) * | 2006-01-25 | 2009-08-06 | インシス セラピューティクス インコーポレイテッド | Sublingual fentanyl spray |
US9289387B2 (en) | 2006-01-25 | 2016-03-22 | Insys Development Company, Inc. | Method of treating pain by administering sublingual fentanyl spray |
US10016403B2 (en) | 2006-01-25 | 2018-07-10 | Insys Development Company, Inc. | Sublingual fentanyl spray |
US8486972B2 (en) | 2006-01-25 | 2013-07-16 | Insys Therapeutics, Inc. | Sublingual fentanyl spray |
US9642797B2 (en) | 2006-01-25 | 2017-05-09 | Insys Development Company, Inc. | Sublingual fentanyl spray and methods of use to treat pain |
EP2641595A1 (en) * | 2006-01-25 | 2013-09-25 | Insys Therapeutics, Inc. | Sublingual fentanyl spray |
EP1976521A4 (en) * | 2006-01-25 | 2010-11-03 | Insys Therapeutics Inc | Sublingual fentanyl spray |
US8835460B2 (en) | 2006-01-25 | 2014-09-16 | Insys Therapeutics, Inc. | Sublingual fentanyl spray and methods of treating pain |
EP1976521A2 (en) * | 2006-01-25 | 2008-10-08 | Insys Therapeutics, Inc. | Sublingual fentanyl spray |
US9241935B2 (en) | 2007-08-02 | 2016-01-26 | Insys Pharma, Inc. | Sublingual fentanyl spray |
US8835459B2 (en) | 2007-08-02 | 2014-09-16 | Insys Therapeutics, Inc. | Sublingual fentanyl spray |
US8486973B2 (en) | 2007-08-02 | 2013-07-16 | Insys Therapeutics, Inc. | Sublingual fentanyl spray |
US9642844B2 (en) | 2007-08-02 | 2017-05-09 | Insys Development Company, Inc. | Sublingual fentanyl spray |
US10610523B2 (en) | 2007-08-02 | 2020-04-07 | Btcp Pharma, Llc | Sublingual fentanyl spray |
WO2011077169A3 (en) * | 2009-12-24 | 2012-03-15 | Norwich Pharma Technologies Limited | Pharmaceutical preparation comprising sufentanil |
Also Published As
Publication number | Publication date |
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KR20050115276A (en) | 2005-12-07 |
BRPI0408209A (en) | 2006-02-14 |
NO20054172D0 (en) | 2005-09-07 |
EP1608372A2 (en) | 2005-12-28 |
MXPA05009602A (en) | 2005-11-08 |
AU2004218876A1 (en) | 2004-09-23 |
AU2004218876B2 (en) | 2007-08-02 |
NO20054172L (en) | 2005-10-06 |
JP2006519770A (en) | 2006-08-31 |
CA2516338A1 (en) | 2004-09-23 |
NZ541781A (en) | 2008-04-30 |
WO2004080382A3 (en) | 2005-03-24 |
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