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WO1995029678A1 - Composition pharmaceutique destinee a un apport transdermique - Google Patents

Composition pharmaceutique destinee a un apport transdermique Download PDF

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Publication number
WO1995029678A1
WO1995029678A1 PCT/EP1995/001519 EP9501519W WO9529678A1 WO 1995029678 A1 WO1995029678 A1 WO 1995029678A1 EP 9501519 W EP9501519 W EP 9501519W WO 9529678 A1 WO9529678 A1 WO 9529678A1
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WO
WIPO (PCT)
Prior art keywords
composition
percent
weight
amount
present
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.)
Ceased
Application number
PCT/EP1995/001519
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English (en)
Inventor
Charanjit Rai Behl
Peter Hofmann
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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
Priority claimed from US08/234,214 external-priority patent/US5580574A/en
Priority claimed from US08/234,216 external-priority patent/US5552153A/en
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Priority to AU23456/95A priority Critical patent/AU2345695A/en
Publication of WO1995029678A1 publication Critical patent/WO1995029678A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives thereof

Definitions

  • Benzodiazepines are used as sedative hypnotics, in the treatment of anxiety disorders and in the treatment of seizures.
  • Benzodiazepine antagonists such as, flumazenil, are used for a complete or partial reversal of the sedative effects of benzodiazepines and for the management of benzodiazepine overdose.
  • Benzodiazepines and benzodiazepine antagonists are administered either via gastrointestinal tract or parenterally.
  • a transdermal route of drug delivery can be used.
  • the most critical problem in this route is the lack of adequate absorption of drugs through the skin.
  • a pharmaceutical composition for transdermal delivery comprising an effective amount of an active ingredient selected from a benzodiazepine and a benzodiazepine antagonist, and either a) caprylic acid, ethanol, and oleic acid; or b) isopropanol, propylene glycol, oleic acid, and water.
  • benzodiazepine means any active pharmaceutical compound in the benzodiazepine family, such as, diazepam, chlordiazepoxide, fluazepam, lorazepam and clonazepam, preferably clonazepam.
  • benzodiazepine antagonist means any compound antagonistic to benzodiazepines, such as, preferably flumazenil.
  • the present invention relates to a pharmaceutical composition for transdermal delivery comprising an effective amount of an active ingredient selected from a benzodiazepine and benzodiazepine antagonist; ethanol; caprylic acid; and oleic acid with or without an inert carrier.
  • Ethanol is present preferably in the range of from about 10 to about 95 percent by weight of the compositions.
  • ethanol is present in the composition in the range of from about 24 to about 90 percent by weight of such compositions.
  • caprylic acid is present in such compositions in the range of from about 1 to about 10 percent by weight of the composition, particularly preferred at about 3 percent.
  • oleic acid is present in such compositions in the range of from about 1 to about 10 percent by weight of the composition, particularly preferred at about 3 percent.
  • ethanol is present in such compositions in an amount of from about 10 to about 95 percent by weight of the composition; particularly preferred in an amount of from about 50 to about 70 percent; caprylic acid is present in the composition in an amount of from about 1 to about 10 percent by weight of the composition, particularly preferred in an amount of from about 3 to 5 percent; and oleic acid is present in such compositions in an amount of from about 1 to about 10 percent by weight of the composition, particularly preferred in an amount of from about 3 to 5 percent.
  • ethanol is present in the composition in an amount of from about 10 to about 95 percent by weight of the composition, particularly preferred in an amount of from about 50 to 90 percent; caprylic acid is present in the composition in an amount of from about 1 to about 10 percent by weight of the composition, particularly preferred at about 3 percent; and oleic acid is present in the composition in an amount of from about 1 to about 10 percent by weight of the composition, particularly preferred at about 3 percent.
  • compositions of the above described aspect of the invention may contain additional enhancing materials such as, for example, silicon fluid such as Silicon Dow® 556 (polyphenyl methyl siloxane), preferably in the range of from about 15 to about 25 percent by weight of the composition, particularly preferred at about 20 percent; dimethylsulfoxide, preferably in the range of from about 1 to about 20 percent by weight of the composition, particularly preferred at about 2 percent; acetone, preferably in the range of from about 15 to about 25 percent by weight of the composition, particularly preferred at about 20 percent; caprylic/capric triglyceride such as Miglyol® 840 (propylene glycol diesters of saturated vegetable fatty acids of the chain lengths Cg-C i o, particularly 2% max caproic acid (C6:0) > 65-80% caprylic acid (C8:0), 15-30% capric acid (Ci0:0) > and 3% max.
  • silicon fluid such as Silicon Dow® 556 (polyphenyl methyl siloxane
  • linoleic acid (Ci 8:2) Dynamit Nobel), preferably in the range of from about 25 to about 40 percent by weight of the composition, particularly preferred at about 36 percent; transcutol (diethylene glycol monoethyl ether from Gattefosse) preferably in the range of from about 15 to about 30 percent by weight of the composition, particularly preferred at about 20 percent; and benzyl alcohol, preferably in the range of from about 5 to about 15 percent by weight of the composition, particularly preferred at about 10 percent.
  • transcutol diethylene glycol monoethyl ether from Gattefosse
  • benzyl alcohol preferably in the range of from about 5 to about 15 percent by weight of the composition, particularly preferred at about 10 percent.
  • the present invention relates to a pharma ⁇ ceutical composition for transdermal delivery comprising an effective amount of an active ingredient selected from a benzodiazepine and benzodiazepine antagonist; isopropanol; propylene glycol; oleic acid; and water with or without an inert carrier.
  • isopropanol is present in such compositions in the range of from about 10 to about 95 percent by weight of the composition. In a particularly preferred embodiment, isopropanol is present in the composition in an amount of about 20% by weight of the composition.
  • propylene glycol is present in these compositions in the range of from about 30 to about 50 percent by weight of the composition, particularly preferred in the range of from about 35 to about 45 percent by weight.
  • oleic acid is present in these compositions in the range of from about 1 to about 10 percent by weight of the composition, particularly preferred is about 5 percent by weight.
  • water is present in these compositions in the range of from about 10 to about 30 percent by weight of the composition, particularly preferred in the range of from about 20 to about 25 percent by weight.
  • the active ingredient is a benzodiazepine antagonist such as flumazenil
  • a benzodiazepine antagonist such as flumazenil
  • isopropanol is present in these compositions in an amount of about 20 percent by weight of the composition
  • propylene glycol is present in an amount of from about 38 to about 47 percent by weight of the composition
  • oleic acid is present in an amount of about 5 percent by weight of the composition
  • water is present in an amount of about 20 percent by weight of the composition.
  • composition of the aforesaid aspect of the invention may contain additional enhancing materials such as, for example, Diacetin (glycerol diacetate from Davos Chemical), preferably in the range of from 5 to 15 percent by weight of the composition, particularly preferred in about 10 percent; Cetiol B® (dibutyl adipate from Henkel Co.), preferably in the range of from 1 to 10 percent by weight of the composition, particularly preferred in about 5 percent; caprylic acid, preferably in the range of from 1 to 10 percent of the composition, particularly preferred in about 5 percent; silicon fluid such as, Silicon Dow® 556 (polyphenyl methyl siloxane), preferably in the range of from 5 to 15 percent by weight of the composition, particularly preferred in about 10 percent; caprylic/capric triglyceride, such as Miglyol® 840 (propylene glycol diesters of saturated vegetable fatty acids of the chain lengths C ⁇ -C l O, particularly 2% max caproic acid (C6:0) > 65
  • capric acid (Ci 0:0). and 3% max. linoleic acid (Cl 8 :2) Dynamit Nobel) preferably in the range of from 5 to 15 percent by weight of the composition, particularly preferred in about 10 percent; transcutol (diethylene glycol monoethyl ether from Gattefosse), preferably in the range of from 5 to 15 percent by weight of the composition, particularly preferred in about 10 percent.
  • compositions in accordance with this invention can be formulated to additionally contain conventional additives or supplementary ingredients in the usual amounts for such materials.
  • the composition can be in the form of a gel, as well as, in the form of a solution, preferably a thickened solution.
  • additives or supplements include the following.
  • Gelling agents which can be used include, for example, hydroxy methyl cellulose, preferably in the range of from 1 to 4 percent by weight of the composition; tragacanth preferably in the range of from 2 to 5 percent by weight of the composition; sodium alginate, preferably in the range of from 2 to 10 percent by weight of the composition; gelatin, preferably in the range of from 2 to 15 percent by weight of the composition; methylcellulose, preferably in the range of from 2 to 4 percent by weight of the composition; sodium carboxymethylcellulose, preferably in the range of from 2 to 5 percent by weight of the composition; and polyvinyl alcohols, preferably in the range of from 10 to 20 percent by weight of the composition.
  • a particularly preferred gelling agent is Klucel® .
  • Klucel HF is a hydroxypropyl cellulose (Hercules Inc.) with a molecular weight in the 1 ,000,000 range and moisture content of 17% for 1 ,500-2,500. Hydroxypropyl cellulose is preferably present in the composition in the range of from 1.0 to 5.0 percent by weight, particularly preferred in the range of from 1.0 to 4.0 percent by weight. Generally, enough Klucel is added to provide a reasonably good gel-consistency to the product.
  • the preservatives which can be used in the invention include, for example, parabens, preferably at about 0.2%; benzoic acid, preferably at about 0.2%; and, chlorocresol, preferably at about 0.1 %.
  • antioxidants can be used in the gel formulations to improve the stability of the drug.
  • antioxidants include, for example, ascorbyl palmitate, butylated hydroxyanisole, butylated hydroxytoluene, potassium sorbate, sodium bisulfate, sorbic acid, propyl gallate and sodium metabisulfite.
  • the pharmaceutical composition of the invention are administered to a host in need of such treatment in a transdermal patch of a reservoir type.
  • Adhesives used in making transdermal patches for use with the invention include, for example, preferably poly-isobutylene, silicone based adhesives and acrylic polymers.
  • the adhesive polymers can be mixed with other excipients such as mineral oil to make them more suitable for a given purpose.
  • the backing membrane of a transdermal patch constitutes the upper part (exposed to the environment) of a transdermal patch and is made of materials such as, for example, preferably polyester films, ethyl vinyl acetate, polypropylene, polyethylene and polyvinyl- chloride.
  • a rate controlling membrane of a transdermal patch is placed in contact with the pharmaceutical composition of the invention and its other side is in contact with the skin of a host.
  • the rate controlling membrane is made of materials such as, for example, preferably, dimethylpolysiloxane, polyacetate, polyurethane and ethylene-vinyl acetate copolymer and polypropylene.
  • a protective liner is placed in contact with the adhesive layer. This liner protects against the drug release from the formulation reservoir until the liner is peeled off the patch and applied on the skin surface of the host.
  • Such liners are made of materials including preferably polyethylene terephthalate film, polyester membrane and polycarbonate film.
  • transdermal patches which are called monolithic or adhesive type patches.
  • the drug is dispersed either in a suitable adhesive or in a suitable non-adhesive polymer and then the mixture is layered onto a membrane. A protective membrane is placed on the adhesive.
  • HGP Hairless guinea pigs
  • the side sites of the animals were cleaned with water.
  • Zero time blood samples were withdrawn from the ocular site.
  • the transdermal drug delivery systems were placed on the skin, two per animal providing a total area of 9.0 to 10.0 sq. cm., precisely measured.
  • the animals were allowed to come out of anesthesia in between blood samples.
  • Blood samples were withdrawn at 1.0, 2.0, 3.0, 4.0, and 6.0 hours.
  • the blood was allowed to clot and then centrifuged to obtain serum.
  • the drug concentration was determined by using an HPLC method. After the last sample point, the transdermal drug delivery system was removed from the animal's skin and the site was examined for any "obvious" signs of irritation/reddening .
  • Serum Collection The animals were bled from the eye into Microtainer serum separator tubes (Becton Dickinson, 5960). The blood (0.6 mL) was centrifuged at 4,000 rpm for 15 minutes (4,400 g) on a Beckman J-6M centrifuge with a JS-4.2 rotor. Serum was separated and frozen until the HPLC analysis. Before sample preparation, the serum was thawed and centrifuged again.
  • Sample Preparation Two hundred and fifty microliters of serum were mixed with 250 mcL of water and 25 mcL of an internal standard, flunitrazepam 1 mcg/mL in methanol, were added. The sample was purified on a solid phase mini column, Adsorbex RP-18 (100 mg; EM Science) using the sample preparation unit Adsorbex SPU). The columns were treated before with 2 mL of methanol and washed with 4 mL of water. Samples were applied and the columns were washed with 4 mL of water. The columns were dried under vacuum (5" Hg) and eluted with two portions of 125 mcL of aceto- nitrile:water (1 : 1).
  • the retention times of the inernal standard, flunitrazepam, and clonazepam or flumazenil were 5.5 and 4.5 minutes, respectively.
  • the HPLC system is connected to a computer where a program was used to determine the area under the curve of the drug and the internal standard .
  • the chromatogram of the HGP serum shows no peak at the retention time of clonazepam indicating an interference free detection of the drug.
  • Sensitivity And Linearity Of Response A standard curve was made by adding clonazepam or. flumazenil and the internal standard to HGP serum. A linear relationship was observed between the observed response and concentration of clonazepam in the range of 5 to 500 ng/mL. The recovery of the drug in these experiments was 75 ⁇ 15%, and was corrected using the internal standard. Apparent limit of quantification was found to be about 5 ng/mL of clonazepam or flumazenil in the HGP serum.
  • HPLC data were computed in terms of drug concentration per unit volume of the serum and were plotted as a function of time. In such experiments, the blood levels are expected to rise to a maximum and then decline due to a decrease in the chemical potential of the drug in the patch. No rate controlling membrane was placed at the bottom of the contemporary transdermal delivery dosage system.
  • Control A contained 11 mg of clonazepam in a formulation comprised of 97% ethanol and 3% Klucel HF applied to an area of 9.8 cm 2
  • Control B contained 12 mg of flumazenil in a formulation comprised of 97% ethanol and 3% Klucel HF applied to an area of 5.0 cm 2 .
  • Example 10 762
  • Example 1 1 73 3
  • Example 12 753
  • Example 13 200
  • Example 14 3
  • Example 15 249
  • Example 16 530 Control A b 15
  • a Drug concentration was 10 mg/Gm
  • Control A contained 12 mg of flumazenil in a formulation comprised of 97% ethanol and 3% Klucel HF
  • compositions in accordance with this invention are set forth below. While clonazepam and flumazenil, the preferred benzodiazepine and benzodiazepine antagonist for the non-aqueous compositions and flumazenil, the preferred benzodiazepine antagonist for the aqueous compositions of this invention, are used to illustrate the compositions, it should be understood that other benzodiazepine and benzodiazepine antagonists may be substituted in appropriate amounts.

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

Abstract

Composition pharmaceutique destinée à un apport transdermique, comprenant une quantité efficace d'un principe actif choisi parmi une benzodiazépine et un antagoniste des benzodiazépines, ainsi que soit de l'éthanol, de l'acide octanoïque et de l'acide oléique, soit de l'isopropanol, du propylèneglycol, de l'acide oléique et de l'eau. En outre, cette composition peut contenir un composé fluide de silicium, de l'alcool de benzyle, du transcutol ou du diméthylsulfoxyde.
PCT/EP1995/001519 1994-04-28 1995-04-21 Composition pharmaceutique destinee a un apport transdermique Ceased WO1995029678A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU23456/95A AU2345695A (en) 1994-04-28 1995-04-21 Pharmaceutical composition for transdermal delivery

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US234,216 1994-04-28
US08/234,214 US5580574A (en) 1994-04-28 1994-04-28 Pharmaceutical composition for transdermal delivery
US08/234,216 US5552153A (en) 1994-04-28 1994-04-28 Pharmaceutical composition for transdermal delivery
US234,214 1994-04-28

Publications (1)

Publication Number Publication Date
WO1995029678A1 true WO1995029678A1 (fr) 1995-11-09

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WO (1) WO1995029678A1 (fr)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0913158A1 (fr) * 1997-09-17 1999-05-06 Permatec Technologie Ag Patch transdermal comprenant une combinaison de deux ou plus de deux acides ou alcools gras comme agents favorisant la pénétration cutanée
EP1030668A4 (fr) * 1997-11-10 2002-09-25 Cellegy Pharma Inc Systeme ameliorant l'administration de medicaments et reduisant les irritations
US6465017B1 (en) 1997-08-26 2002-10-15 Unipharm Ltd. Process for the preparation of solid oral dosage forms comprising alendronic acid
WO2005039531A1 (fr) * 2003-10-10 2005-05-06 Antares Pharma Ipl Ag Formulation pharmaceutique transdermique visant a reduire les residus sur la peau
JP2007505769A (ja) * 2003-09-18 2007-03-15 ユナイテッド・ステイツ・ジプサム・カンパニー 繊維によって強化されている構造用セメントパネルを生産するスラリー供給装置
WO2008027357A3 (fr) * 2006-08-28 2008-04-17 Jazz Pharmaceuticals Compositions pharmaceutiques de clonazépam et procédés d'utilisation de celles-ci
US7387788B1 (en) 2003-10-10 2008-06-17 Antares Pharma Ipl Ag Pharmaceutical compositions of nicotine and methods of use thereof
US7404965B2 (en) 2000-08-03 2008-07-29 Antares Pharma Ipl Ag Composition for transdermal and/or transmucosal administration of active compounds that ensures adequate therapeutic levels
US7425340B2 (en) 2004-05-07 2008-09-16 Antares Pharma Ipl Ag Permeation enhancing compositions for anticholinergic agents
US7470433B2 (en) 2000-08-03 2008-12-30 Antares Pharma Ipl Ag Formulations for transdermal or transmucosal application
WO2010008600A1 (fr) * 2008-07-16 2010-01-21 Dermworx Incorporated Système d'apport de médicament topique
US7704403B2 (en) 1999-10-13 2010-04-27 Electromagnetic Corporation Composition of matter tailoring: system I
WO2010094074A1 (fr) * 2009-02-20 2010-08-26 Palmaya Pty Ltd Préparation pharmaceutique et système d'administation
US8067399B2 (en) 2005-05-27 2011-11-29 Antares Pharma Ipl Ag Method and apparatus for transdermal or transmucosal application of testosterone
US8268346B2 (en) 2006-04-21 2012-09-18 Antares Pharma Ipl Ag Methods of treating hot flashes with formulations for transdermal or transmucosal application
US8652491B2 (en) 2000-08-03 2014-02-18 Antares Pharma Ipl Ag Transdermal compositions for anticholinergic agents
US9790574B2 (en) 2010-11-22 2017-10-17 Electromagnetics Corporation Devices for tailoring materials
AU2011279557B2 (en) * 2010-07-16 2018-09-27 Verita Research Pte Ltd Pharmaceutical compositions for sustained delivery of benzodiazepine antagonists

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH634749A5 (de) * 1978-06-07 1983-02-28 Kali Chemie Pharma Gmbh Arzneimittelzubereitung mit verbesserter resorptionseigenschaft und verfahren zu deren herstellung.
EP0159167A2 (fr) * 1984-04-05 1985-10-23 Takeda Chemical Industries, Ltd. Base pour onguents

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH634749A5 (de) * 1978-06-07 1983-02-28 Kali Chemie Pharma Gmbh Arzneimittelzubereitung mit verbesserter resorptionseigenschaft und verfahren zu deren herstellung.
EP0159167A2 (fr) * 1984-04-05 1985-10-23 Takeda Chemical Industries, Ltd. Base pour onguents

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6465017B1 (en) 1997-08-26 2002-10-15 Unipharm Ltd. Process for the preparation of solid oral dosage forms comprising alendronic acid
US6231885B1 (en) 1997-09-17 2001-05-15 Permatec Technologie Ag Composition for controlled and sustained transdermal administration
EP0913158A1 (fr) * 1997-09-17 1999-05-06 Permatec Technologie Ag Patch transdermal comprenant une combinaison de deux ou plus de deux acides ou alcools gras comme agents favorisant la pénétration cutanée
EP1030668A4 (fr) * 1997-11-10 2002-09-25 Cellegy Pharma Inc Systeme ameliorant l'administration de medicaments et reduisant les irritations
US6579865B2 (en) 1997-11-10 2003-06-17 Cellegy Pharmaceuticals, Inc. Penetration enhancing and irritation reducing systems
US7157097B2 (en) 1997-11-10 2007-01-02 Cellegy Pharmaceuticals Inc. Penetration enhancing and irritation reducing systems
US7704403B2 (en) 1999-10-13 2010-04-27 Electromagnetic Corporation Composition of matter tailoring: system I
US8652491B2 (en) 2000-08-03 2014-02-18 Antares Pharma Ipl Ag Transdermal compositions for anticholinergic agents
US7470433B2 (en) 2000-08-03 2008-12-30 Antares Pharma Ipl Ag Formulations for transdermal or transmucosal application
US8980290B2 (en) 2000-08-03 2015-03-17 Antares Pharma Ipl Ag Transdermal compositions for anticholinergic agents
US7404965B2 (en) 2000-08-03 2008-07-29 Antares Pharma Ipl Ag Composition for transdermal and/or transmucosal administration of active compounds that ensures adequate therapeutic levels
JP2007505769A (ja) * 2003-09-18 2007-03-15 ユナイテッド・ステイツ・ジプサム・カンパニー 繊維によって強化されている構造用セメントパネルを生産するスラリー供給装置
US8980309B2 (en) 2003-10-10 2015-03-17 Antares Pharma Ipl Ag Transdermal testosterone formulation for minimizing skin residues
AU2004283431B2 (en) * 2003-10-10 2009-09-10 Antares Pharma Ipl Ag Transdermal pharmaceutical formulation for minimizing skin residues
US7335379B2 (en) 2003-10-10 2008-02-26 Antares Pharma Ipl Ag Transdermal pharmaceutical formulation for minimizing skin residues
US7387788B1 (en) 2003-10-10 2008-06-17 Antares Pharma Ipl Ag Pharmaceutical compositions of nicotine and methods of use thereof
WO2005039531A1 (fr) * 2003-10-10 2005-05-06 Antares Pharma Ipl Ag Formulation pharmaceutique transdermique visant a reduire les residus sur la peau
US7425340B2 (en) 2004-05-07 2008-09-16 Antares Pharma Ipl Ag Permeation enhancing compositions for anticholinergic agents
US8338400B2 (en) 2005-05-27 2012-12-25 Antares Pharma Ipl Ag Methods and apparatus for transdermal or transmucosal application of testosterone
US8067399B2 (en) 2005-05-27 2011-11-29 Antares Pharma Ipl Ag Method and apparatus for transdermal or transmucosal application of testosterone
US8647665B2 (en) 2006-04-21 2014-02-11 Antares Pharma Ipl Ag Methods of treating hot flashes with formulations for transdermal or transmucosal application
US8268346B2 (en) 2006-04-21 2012-09-18 Antares Pharma Ipl Ag Methods of treating hot flashes with formulations for transdermal or transmucosal application
US8609651B2 (en) 2006-08-28 2013-12-17 Jazz Pharmaceuticals, Inc. Pharmaceutical compositions of benzodiazepines and method of use thereof
AU2007290589B2 (en) * 2006-08-28 2012-04-05 Jazz Pharmaceuticals, Inc. Pharmaceutical compositions of clonazepam and methods of use thereof
US8716279B2 (en) 2006-08-28 2014-05-06 Jazz Pharmaceuticals, Inc. Pharmaceutical compositions of clonazepam and method of use thereof
WO2008027357A3 (fr) * 2006-08-28 2008-04-17 Jazz Pharmaceuticals Compositions pharmaceutiques de clonazépam et procédés d'utilisation de celles-ci
WO2010008600A1 (fr) * 2008-07-16 2010-01-21 Dermworx Incorporated Système d'apport de médicament topique
US9050293B2 (en) 2008-07-16 2015-06-09 Juventio, Llc Small molecule solubilization system
WO2010094074A1 (fr) * 2009-02-20 2010-08-26 Palmaya Pty Ltd Préparation pharmaceutique et système d'administation
AU2010215075B2 (en) * 2009-02-20 2015-08-20 Palmaya Pty Ltd Pharmaceutical preparation and delivery system
US9283212B2 (en) 2009-02-20 2016-03-15 Palmaya Pty Ltd Pharmaceutical preparation and delivery system
AU2011279557B2 (en) * 2010-07-16 2018-09-27 Verita Research Pte Ltd Pharmaceutical compositions for sustained delivery of benzodiazepine antagonists
US9790574B2 (en) 2010-11-22 2017-10-17 Electromagnetics Corporation Devices for tailoring materials

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