WO2000074652A1 - Pharmazeutische zusammensetzung zur nasalen anwendung von wasserlöslichen wirkstoffen - Google Patents
Pharmazeutische zusammensetzung zur nasalen anwendung von wasserlöslichen wirkstoffen Download PDFInfo
- Publication number
- WO2000074652A1 WO2000074652A1 PCT/EP2000/004800 EP0004800W WO0074652A1 WO 2000074652 A1 WO2000074652 A1 WO 2000074652A1 EP 0004800 W EP0004800 W EP 0004800W WO 0074652 A1 WO0074652 A1 WO 0074652A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pharmaceutical composition
- macrogrog
- use according
- nasal use
- acid
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0043—Nose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
Definitions
- the invention relates to a pharmaceutical composition for nasal use, consisting of at least one water-soluble active ingredient, neutral oil and optionally at least one solubilizer, it being possible to dispense with the addition of preservatives and propellants.
- blowing agents are representatives from the group of the fluorochlorohydrocarbons, or fluorohydrocarbons.
- the use of these blowing agents is to be avoided today for reasons of environmental protection, since they destroy the ozone layer. From an economic point of view, the use of blowing agents is an additional cost factor.
- the problem with these aqueous solutions is that sterile manufacture is expensive and difficult. Contamination after opening can hardly be prevented without the addition of a preservative.
- Preservatives often have a high allergy potential, so allergy sufferers often cannot use these medicines.
- all common and approved preservatives are cytotoxic and impair the ciliary function and thus the clearance.
- the addition of preservatives also means that preservation stress tests must be carried out on the pharmaceutical composition in order to achieve a sufficient level To ensure conservation. These tests are lengthy, time-consuming and costly.
- Aqueous solutions are also relatively problematic in terms of their stability.
- the strong pH dependence of the nasal absorption of active substances from aqueous solutions represents a further problem.
- the optimal environment for the cilia of the nasal mucosa is between 7 and 9.
- maximum absorption takes place at a pH ⁇ 6.
- a pH of 4 leads to the destruction of the cilia.
- Many active substances also have an acid instability, so that at the pH value for optimal absorption a large part of the active substance is subject to a change in the chemical structure.
- This chemically modified active ingredient has no pharmacological activity, so that the bioavailability and the therapeutic activity are greatly reduced.
- a nasal application of acid-labile active ingredients has thus far been difficult.
- a liposome formulation is an oil / water or water / oil emulsion.
- the preparation of these liposome formulations is complex. The stability is very low, since the enclosed active ingredient dissolves from these liposomes over time, so that the amount of active ingredient actually applied decreases.
- sterility can hardly be maintained over a longer period without the addition of preservatives, since a not inconsiderable proportion of water is included in the liposomes. This water inclusion poses a great risk of contamination by bacteria, fungi and viruses.
- the object of the invention is to provide a pharmaceutical composition for the nasal application of water-soluble active ingredients in the form of a dispersion or solution, it being possible to dispense with the use of propellants and preservatives and the composition being essentially water-free.
- the object is achieved according to the invention by a pharmaceutical composition which contains at least one water-soluble active ingredient, neutral oil and, if appropriate, a solubilizer.
- the pharmaceutical composition according to the invention can be applied to the nasal mucosa without the addition of propellants by means of devices which can produce a precisely defined dosage.
- the preferred devices include common pump and valve sprays and nasal drops.
- the composition has good absorption, since it adheres well to the nasal mucosa, and due to the neutral oil there is a cell spread and the active ingredient is thus very easily absorbed from the composition by the nasal mucosa.
- the problem of pH in aqueous solutions with regard to optimal absorption does not arise with the composition according to the invention. Maximum absorption can be achieved without destroying the cilia, restricting their function or causing a change in the chemical structure of the active ingredient.
- the composition can be easily filtered, so that a sterile solution (OJ ⁇ m pore size) can be prepared without great effort using a sterile filtration. If a dispersion is present, sterility can be achieved without any problems by first filtering the neutral oil in a sterile manner and then preparing the dispersion in a closed circuit.
- the stability is very high, since even in the event of subsequent contamination, it is not possible for human-pathogenic microorganisms such as bacteria, fungi and viruses to multiply and survive in the neutral oil. Due to this fact, no preservative has to be added. Damage to the nasal mucosa and impairment of the ciliary function by preservatives can thus be prevented, especially with long-term treatment, and complex, lengthy preservation stress tests can be dispensed with.
- the tolerance of the composition according to the invention on the nasal mucosa is very good, so that irritation of the mucous membrane caused by the active ingredient and / or the auxiliary substances is minimized and patient compliance can thus be increased.
- the production is simple and inexpensive, since no further additives are necessary and the neutral oil as a carrier is cheap.
- Essentially water-free is understood here to mean a water content in the composition which can result from water of hydration, water of crystallization and / or residual moisture in the neutral oil, the active ingredients and / or the auxiliaries.
- neutral oil means medium-chain triglycerides. These can be achieved by esterifying medium-chain fatty acids such as Capronic, capric, caprylic, lauric, myristic, linoleic and succinic acid, in particular capric, caprylic, linoleic and
- Succinic acid can be obtained with glycerol and / or propylene glycol (Miglyol 810, 812,
- the viscosity of the neutral oils used is 1-40 mPa s, in particular 5-20 mPa s, a viscosity of 8-15 mPa s is preferred.
- the preferred neutral oil according to the invention is Miglyol 840.
- the pharmaceutical composition according to the invention can contain water-soluble corticoids, 5-HT, antagonists, sympatholytics / sympathomimetics, anticholinergics,
- Weaning agents, analgesics, calcium antagonists, antiemetics, pituitary / hypothalamic hormones, opiate antagonists, anticoagulants, antiparkinson agents, ACE inhibitors, insulin, polihexanide, allicin, sildenafil citrate, lidocaine HCl, oxytocin and / or possible co-enzyme components contain Q.
- the pharmaceutical composition according to the invention can be selected from the group of corticoids e.g. B. beclomethasone, budesonide propionate, flunisolide acetate, triamcinolone, fluticasone, betamethasone 17-valerate, glycic acid, fluocortolone and / or their derivatives as an active ingredient component.
- corticoids e.g. B. beclomethasone, budesonide propionate, flunisolide acetate, triamcinolone, fluticasone, betamethasone 17-valerate, glycic acid, fluocortolone and / or their derivatives as an active ingredient component.
- the pharmaceutical composition according to the invention can contain, for example, sumatriptan hydrogen succinate, rizatriptan benzoate and / or their derivatives from the group of 5-HT, antagonists as active ingredient.
- the pharmaceutical composition according to the invention can be selected from the group of the sympatholytic / sympathomimetic, for example acebutolol hydrochloride, adimolol hydrochloride, adrenaline hydrogen tartrate, amosulalol hydrochloride, arotinolol monohydrochloride, betaxolol hydrochloride, bevantolol hydrochloride, bisoprolololololate, baterolololololate, baterolololololate, baterolololololate, baterolololololate, baterolololololate, baterolololololate, baterolololol
- the pharmaceutical composition according to the invention can from the group of anticholinergics, for example ipratropium bromide, oxitropium bromide, atropine methyl bromide, atropine methyl nitrate, atropine sulfate, atropine valerianate, scopolamine hydrobromide, scopolamine hydrochloride, scopolamine hydroiodide and / or contain derivatives thereof as active ingredient.
- the pharmaceutical composition according to the invention can contain, for example, nicotine, disulfiram and / or their derivatives, in particular nicotine, as an active ingredient component from the group of weaning agents.
- the pharmaceutical composition according to the invention can be selected from the group of analgesics e.g. Codeine, Codein Hydrochloride, Codeine Phosphate, Tilidine, Tilidine Mesylate, Tilidine Hydrochloride, Metamizole Sodium, Dextropropoxyphenhydrochloride, Diclofenac Sodium, Aceclofenac Sodium, Amfenac Sodium, Bromfenac Sodium, Clidanac Sodium, Etodolac Sodium, Felbinac Sodium, F Lonazolac sodium, mofezolac sodium, oxindanac sodium, tifurac sodium, indomethacin sodium, acemetacin sodium, piroxicam, ampiroxicam, meloxicam cyclodextrin, isoxicam, lornoxicam, tenoxicam, bupreno hydrochloride, morphine acetate, morphine acetate, morphine acetate
- the pharmaceutical composition according to the invention can be selected from the group of calcium antagonists e.g. Contain diltiazem hydrochloride, clentiazem hydrochloride and / or their derivatives as active ingredient.
- calcium antagonists e.g. Contain diltiazem hydrochloride, clentiazem hydrochloride and / or their derivatives as active ingredient.
- the pharmaceutical composition according to the invention can be selected from the group of antiemetics e.g. Alizaprid hydrochloride, batanopride hydrochloride, cleboprid hydrochloride, dazoprid hydrochloride, metoclopramide hydrochloride, pancoprid hydrochloride and / or their derivatives as an active ingredient component.
- antiemetics e.g. Alizaprid hydrochloride, batanopride hydrochloride, cleboprid hydrochloride, dazoprid hydrochloride, metoclopramide hydrochloride, pancoprid hydrochloride and / or their derivatives as an active ingredient component.
- the pharmaceutical composition according to the invention can be selected from the group of the pituitary / hypothalamic hormones e.g. Contain tetracosactide acetate, choringonadotrophin, follitropin, menotropin, somatropin, desmopressin acetate, nafarelin acetate, leuprorelin acetate, buserelin acetate, deslorelin acetate, goserelin acetate, triptorelin acetate and / or their derivatives as an active ingredient.
- the pituitary / hypothalamic hormones e.g. Contain tetracosactide acetate, choringonadotrophin, follitropin, menotropin, somatropin, desmopressin acetate, nafarelin acetate, leuprorelin acetate, buserelin acetate, deslorelin acetate, goserelin
- the pharmaceutical composition according to the invention can from the group of opiate antagonists z. B. naloxone, naltrexone and / or their derivatives, especially naloxone as an active ingredient component.
- the pharmaceutical composition according to the invention can contain, for example, heparin sodium, certoparin, dalteparin, danaparoid, enoxaparin, nadroparin, reviparin, tinzaparin, heparinoids and / or their derivatives as active ingredient components from the group of anticoagulants.
- the pharmaceutical composition according to the invention can be selected from the group of antiparkinsonian agents, the water-soluble salts of e.g. Aptiganel, Budipin, Cabergolin, Droxidopa, Etacapon, Idazoxan, Lazabemid, Milacemid, Mofegilin, Pergolid (Pergolidmesylat, Pergolidhydrochlorid), Pramipexol, Quineloran, Rasagelin, Remacemid, Ropinorol, Seleginhydonol or their component ( contain.
- the water-soluble salts e.g. Aptiganel, Budipin, Cabergolin, Droxidopa, Etacapon, Idazoxan, Lazabemid, Milacemid, Mofegilin, Pergolid (Pergolidmesylat, Pergolidhydrochlorid), Pramipexol, Quineloran, Rasagelin, Remacemid, Ropinorol, Seleginhydonol or their
- the pharmaceutical composition according to the invention can be selected from the group of ACE inhibitors e.g. Alacepril, benazepril, captopril, ceronapril, cilazapril, denapril, enalapril, enalapril maleate, fosinopril, imidapril, lisinopril, moexipril, moveltipril, perindopril, derinaprilap, riliprilap, biliprilap included as active ingredient.
- ACE inhibitors e.g. Alacepril, benazepril, captopril, ceronapril, cilazapril, denapril, enalapril, enalapril maleate, fosinopril, imidapril, lisinopril, moexipril, moveltipril, perindopril, derinaprilap, riliprilap, bil
- the pharmaceutical composition according to the invention can have an active substance content of 0.01-15% by weight, in particular 0.08-5% by weight, preferably 0J, 0J, 0.5 and 1% by weight.
- the percentages relate to the total amount of the pharmaceutical composition.
- the pharmaceutical composition according to the invention may optionally also contain antioxidants such as, for example, ⁇ -tocopherol, ⁇ -tocopherol esters, ascorbic acid, ascorbic acid esters (myristate, palmitate and stearate), ⁇ -carotene, cysteine, acetylcysteine, folic acid (vitamin B 2 group), Phytic acid, ice and / or trans-urocanoic acid, carnosine (N-ß-alanine-L-histidine), histidine, flavones, flavonoids, lycopene, tyrosine, glutathione, glutathione esters, ⁇ -lipoic acid, ubiquinone, nordihydroguaiaretic acid (NDGA), gallic acid esters (Ethyl, propyl, octyl, dodecyl gallate), phosphoric acid derivatives (monophosphates, polyphosphates), butylated hydroxyto
- the content of the optionally added antioxidants can be 0.001-1% by weight, based on the total amount of the pharmaceutical composition.
- the pharmaceutical composition according to the invention can optionally also provide solubilizers such as e.g. Lysophosphatidylcholine, lysophosphatidylglycerol, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol (ol) e, spingophospholipids, sodium dodecyl sulfate, sodium cetylstearyl sulfate, sodium dioctyl sulfosuccinate,
- solubilizers such as e.g. Lysophosphatidylcholine, lysophosphatidylglycerol, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol (ol) e, spingophospholipids, sodium dodecyl sulfate, sodium cetylstearyl sulfate, sodium dioctyl sulfosucc
- Glycerol monooleate macrogol stearate, polyoxyl 40 stearate, polyoxyl 50 stearate,
- solubilizers can support or enable a solution of the water-soluble active ingredient in the neutral oil and, among other things, Prevent any adsorption compound of the active ingredient from occurring with the wall of the container (deposit).
- the pharmaceutical composition according to the invention can optionally also be absorption enhancers such as e.g. Dimethyl-ß-cyclodextrin, permethyl-ß-cyclodextrin, hydroxypropyl-ß-cyclodextrin, randomized methylated ß-cyclodextrin, carboxymethyl-ß-cyclodextrin, maltosyl-ß-cycodextrin, ⁇ -cyclodextrin, sodium taurofusidate,
- absorption enhancers such as e.g. Dimethyl-ß-cyclodextrin, permethyl-ß-cyclodextrin, hydroxypropyl-ß-cyclodextrin, randomized methylated ß-cyclodextrin, carboxymethyl-ß-cyclodextrin, maltosyl-ß-cycodextrin, ⁇ -cyclodextrin, sodium taurofusidate,
- Example 1 The invention is illustrated in more detail by the following examples, but without restricting the scope of the invention.
- Example 1 The invention is illustrated in more detail by the following examples, but without restricting the scope of the invention.
- 1 g (-) - nicotine is introduced into 100 ml Miglyol 840. This composition is sterilized and filled into a pump spray with a dose volume of 50 ⁇ l.
- the active substance concentration for a 50 ⁇ l spray is 500 ⁇ g (-) - nicotine.
- Concentrate of polyhexanide 20 g of polyhexanide are introduced into 100 ml of Miglyol 840 (20% formulation).
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU50720/00A AU5072000A (en) | 1999-06-02 | 2000-05-26 | Pharmaceutical composition for nasally administering water-soluble active substances |
JP2001501189A JP2005505491A (ja) | 1999-06-02 | 2000-05-26 | 水溶性活性物質の鼻腔内投与用医薬組成物 |
EP00935121A EP1189596A1 (de) | 1999-06-02 | 2000-05-26 | Pharmazeutische zusammensetzung zur nasalen anwendung von wasserlöslichen wirkstoffen |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19925289.0 | 1999-06-02 | ||
DE1999125289 DE19925289A1 (de) | 1999-06-02 | 1999-06-02 | Neue pharmazeutische Zusammensetzung zur nasalen Anwendung von wasserlöslichen Wirkstoffen |
DE1999136545 DE19936545A1 (de) | 1999-08-03 | 1999-08-03 | Neue pharmazeutische Zusammensetzung zur nasalen Anwendung von wasserlöslichen Wirkstoffen |
DE19936545.8 | 1999-08-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000074652A1 true WO2000074652A1 (de) | 2000-12-14 |
Family
ID=26053615
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/004800 WO2000074652A1 (de) | 1999-06-02 | 2000-05-26 | Pharmazeutische zusammensetzung zur nasalen anwendung von wasserlöslichen wirkstoffen |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1189596A1 (de) |
JP (1) | JP2005505491A (de) |
AU (1) | AU5072000A (de) |
WO (1) | WO2000074652A1 (de) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2856302A1 (fr) * | 2003-06-20 | 2004-12-24 | Anben Pharma | Composition pharmaceutique utilisee en tant qu'agent anti-infectueux des voies respiratoires superieures |
JP2006522105A (ja) * | 2003-03-31 | 2006-09-28 | アボット・ラボラトリーズ | α−ヒドロキシ酸エステル薬剤送達組成物及び使用方法 |
WO2007125318A1 (en) * | 2006-04-25 | 2007-11-08 | Optinose As | Non-aqueous liquid formulation for nasal or buccal administration |
US9192570B2 (en) | 2013-12-20 | 2015-11-24 | AntiOP, Inc. | Intranasal naloxone compositions and methods of making and using same |
US9211253B2 (en) | 2014-03-14 | 2015-12-15 | Lightlake Therapeutics Inc. | Nasal drug products and methods of their use |
US9468747B2 (en) | 2014-03-14 | 2016-10-18 | Opiant Pharmaceuticals, Inc. | Nasal drug products and methods of their use |
US9561177B2 (en) | 2014-03-14 | 2017-02-07 | Adapt Pharma Limited | Nasal drug products and methods of their use |
US10085937B2 (en) | 2014-03-14 | 2018-10-02 | Adapt Pharma Limited | Nasal drug products and methods of their use |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0301392A1 (de) * | 1987-07-30 | 1989-02-01 | Pierrel S.p.A. | Pharmazeutische Zusammensetzung zur intranasalen Verabreichung, die GHRH, einen cholinergischen Agonisten und gegebenenfalls ein Gallensalz enthält |
WO1991016929A1 (en) * | 1990-05-10 | 1991-11-14 | Novo Nordisk A/S | A pharmaceutical preparation containing n-glycofurols and n-ethylene glycols |
EP0474453A2 (de) * | 1990-09-03 | 1992-03-11 | Takeda Chemical Industries, Ltd. | Proteine oder wirksame Peptide und hitzelabiles Enterotoxin B enthaltende pharmazeutische Zusammensetzung und ihre Anwendung durch die Schleimhaut |
WO1997038663A2 (en) * | 1996-04-12 | 1997-10-23 | Flemington Pharmaceutical Corporation | Buccal, non-polar spray or capsule |
-
2000
- 2000-05-26 JP JP2001501189A patent/JP2005505491A/ja active Pending
- 2000-05-26 AU AU50720/00A patent/AU5072000A/en not_active Abandoned
- 2000-05-26 WO PCT/EP2000/004800 patent/WO2000074652A1/de not_active Application Discontinuation
- 2000-05-26 EP EP00935121A patent/EP1189596A1/de not_active Withdrawn
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0301392A1 (de) * | 1987-07-30 | 1989-02-01 | Pierrel S.p.A. | Pharmazeutische Zusammensetzung zur intranasalen Verabreichung, die GHRH, einen cholinergischen Agonisten und gegebenenfalls ein Gallensalz enthält |
WO1991016929A1 (en) * | 1990-05-10 | 1991-11-14 | Novo Nordisk A/S | A pharmaceutical preparation containing n-glycofurols and n-ethylene glycols |
EP0474453A2 (de) * | 1990-09-03 | 1992-03-11 | Takeda Chemical Industries, Ltd. | Proteine oder wirksame Peptide und hitzelabiles Enterotoxin B enthaltende pharmazeutische Zusammensetzung und ihre Anwendung durch die Schleimhaut |
WO1997038663A2 (en) * | 1996-04-12 | 1997-10-23 | Flemington Pharmaceutical Corporation | Buccal, non-polar spray or capsule |
Non-Patent Citations (2)
Title |
---|
DOLDER R: "Rhinologische Präparate (Kapitel 17.2)" * |
SUCKER H, ET AL: "Pharmazeutische Technologie", 1991, GEORG THIEME VERLAG, STUTTGART, DE, ISBN: 3-13-395802, XP002149442 * |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006522105A (ja) * | 2003-03-31 | 2006-09-28 | アボット・ラボラトリーズ | α−ヒドロキシ酸エステル薬剤送達組成物及び使用方法 |
JP2012136521A (ja) * | 2003-03-31 | 2012-07-19 | Abbott Lab | α−ヒドロキシ酸エステル薬剤送達組成物及び使用方法 |
EP1493444A1 (de) * | 2003-06-20 | 2005-01-05 | Anben Pharma SARL | Pharmazeutische Zusammensetzung zur Verwendung als Antiinfektivum der oberen Atemwege |
FR2856302A1 (fr) * | 2003-06-20 | 2004-12-24 | Anben Pharma | Composition pharmaceutique utilisee en tant qu'agent anti-infectueux des voies respiratoires superieures |
WO2007125318A1 (en) * | 2006-04-25 | 2007-11-08 | Optinose As | Non-aqueous liquid formulation for nasal or buccal administration |
US9289425B2 (en) | 2013-12-20 | 2016-03-22 | AntiOP, Inc. | Intranasal naloxone compositions and methods of making and using same |
US9192570B2 (en) | 2013-12-20 | 2015-11-24 | AntiOP, Inc. | Intranasal naloxone compositions and methods of making and using same |
US9211253B2 (en) | 2014-03-14 | 2015-12-15 | Lightlake Therapeutics Inc. | Nasal drug products and methods of their use |
US9468747B2 (en) | 2014-03-14 | 2016-10-18 | Opiant Pharmaceuticals, Inc. | Nasal drug products and methods of their use |
US9480644B2 (en) | 2014-03-14 | 2016-11-01 | Opiant Pharmaceuticals, Inc. | Nasal drug products and methods of their use |
US9561177B2 (en) | 2014-03-14 | 2017-02-07 | Adapt Pharma Limited | Nasal drug products and methods of their use |
US9629965B2 (en) | 2014-03-14 | 2017-04-25 | Opiant Pharmaceuticals, Inc. | Nasal drug products and methods of their use |
US9707226B2 (en) | 2014-03-14 | 2017-07-18 | Adapt Pharma Limited | Nasal drug products and methods of their use |
US9775838B2 (en) | 2014-03-14 | 2017-10-03 | Adapt Pharma Limited | Nasal drug products and methods of their use |
US10085937B2 (en) | 2014-03-14 | 2018-10-02 | Adapt Pharma Limited | Nasal drug products and methods of their use |
Also Published As
Publication number | Publication date |
---|---|
AU5072000A (en) | 2000-12-28 |
EP1189596A1 (de) | 2002-03-27 |
JP2005505491A (ja) | 2005-02-24 |
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