WO2007074239A1 - Stabilisation de testosterone au sein de dispositifs transdermiques. - Google Patents
Stabilisation de testosterone au sein de dispositifs transdermiques. Download PDFInfo
- Publication number
- WO2007074239A1 WO2007074239A1 PCT/FR2006/002873 FR2006002873W WO2007074239A1 WO 2007074239 A1 WO2007074239 A1 WO 2007074239A1 FR 2006002873 W FR2006002873 W FR 2006002873W WO 2007074239 A1 WO2007074239 A1 WO 2007074239A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- desiccant
- testosterone
- use according
- dta
- adhesive
- 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
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
-
- 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
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61J—CONTAINERS SPECIALLY ADAPTED FOR MEDICAL OR PHARMACEUTICAL PURPOSES; DEVICES OR METHODS SPECIALLY ADAPTED FOR BRINGING PHARMACEUTICAL PRODUCTS INTO PARTICULAR PHYSICAL OR ADMINISTERING FORMS; DEVICES FOR ADMINISTERING FOOD OR MEDICINES ORALLY; BABY COMFORTERS; DEVICES FOR RECEIVING SPITTLE
- A61J1/00—Containers specially adapted for medical or pharmaceutical purposes
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/26—Androgens
Definitions
- the present invention relates to the field of self-adhesive transdermal devices (DTA) for the administration of testosterone and / or at least one derivative and in particular the stabilization of testosterone contained in such devices, in particular when testosterone is present in high concentrations.
- DTA self-adhesive transdermal devices
- Such DTAs are pharmaceutical forms that allow the percutaneous administration of active principles in the context of chronic pathologies or even as a preventive measure.
- DTAs promoting the administration of such hormones, in particular testosterone.
- Testosterone known as systemic nomenclature as 17-hydroxyandrost-7-en-3-one is the main circulating hormone of the androgenic type. Under the action of 5 alpha-reductase, it is converted into dihydro-testosterone, the hormone responsible for sexual differentiation.
- DTAs include tank devices and matrix devices.
- the active ingredient is contained in a gel disposed between a support and a membrane.
- the active ingredient is contained within a matrix layer which is generally itself self-adhesive.
- DTAs One of the problems with DTAs is the slow penetration of the active ingredient through the skin.
- absorption promoters and / or conditions of supersaturation of testosterone so as to cause forced passive diffusion.
- a maximum permitted rate of androstenedione of 3% by weight relative to the amount of testosterone and a rate of other impurities of 3% by weight relative to the amount of testosterone, at the end of the expiration period, are essential prerequisites to meet the registration requirements for a commercially viable product.
- the stability of the testosterone in a DTA is obtained by the joint presence of a very weak amount of another steroid hormone, estrone in the self-adhesive matrix layer.
- estrone is undesirable in the context of a medical application of hormone therapy.
- the DTA is composed of several layers, one layer of which is intended to absorb ambient humidity, since it is composed of polymers such as PVA, PVP and polyvinylacetate. The manufacture of such a device is more complex.
- the present invention addresses the problem of the stability of testosterone within DTA, and more particularly in DTA of the matrix type. Indeed, it has been remarked surprisingly and completely unexpectedly that the use of a desiccant makes it possible to limit the formation of oxidation and hydroxylation impurities.
- the present invention therefore relates to the use of a desiccant to limit the degradation of testosterone present in a self-adhesive transdermal device contained in a substantially sealed package.
- Desiccant means any product having a high affinity for water and capable of fixing the water contained in the internal atmosphere of the package or water likely to penetrate into said packaging.
- degradation of testosterone is meant the formation of oxidation impurities and / or hydroxylation of said testosterone.
- the use according to the present invention is understood to mean disposing within a sachet-type package, preferably waterproof to water vapor and oxygen, containing DTA including testosterone, a desiccant.
- packaging is meant that it is an assembly constituted by the arrangement of materials of any kind intended to contain and protect the DTA during its handling, transport and storage.
- substantially watertight means that said package substantially opposes the passage of oxygen and water vapor from the atmosphere to the interior of said package, and this throughout the storage packed DTA.
- the desiccant is preferentially physically dissociated from the DTA.
- the desiccant may be any type of desiccant known and used in the pharmaceutical industry such as those used in tablet tubes. It may be silica gel or molecular sieve, for example.
- molecular sieves most often composed of sodium or potassium salts of aluminum silicate, silica, magnesium oxide, sodium or aluminum, for example. These products are in the form of a very fine powder whose available size is between 1 and 10 A.
- the desiccant is preferably not intended to form a body with the DTA but to be rather physically independent. In the same way, this desiccating agent can be associated with the packaging and form a body with this one as to be physically independent.
- the desiccant may be disposed within the package containing the DTA in the form of a porous bag, free or glued, containing said desiccant, for example. It may also be, for example, a desiccant label, free or sticky, comprising the desiccant sandwiched between an adhesive support and a porous cover sheet, for example non-woven. Such a label can thus be glued inside the sealed package containing the DTA.
- This label can be physically independent of the DTA as explained above, however it can also be considered that it is glued on the outer face of the support layer of the DTA, for example.
- desiccant particularly suitable include the product DESIMAX ® marketed by MULTISORB Technologies. It is a very thin, moisture-absorbing adhesive label that can easily be placed inside a sealed package containing DTA with testosterone.
- Another particularly suitable type of desiccant is a label consisting of polymers in which the desiccant itself is distributed as homogeneously as possible.
- DTAs containing testosterone may also be packaged in a package having a very low permeability, such as a blister comprising a bottom made of thermoformed plastic material and a delaminable lid in the form of an alumino-plastic sheet or preferably any flexible aluminum. thermocollé.
- the desiccant product can be disposed in the form of a label preferably adhered to an inner face of the blister, either on the bottom or on the delaminable lid.
- the DTAs in question may as well be packaged in a sealed bag, formed by the assembly of multilayer films welded on their periphery.
- Suitable multilayer films are those traditionally used in the pharmaceutical industry, and exemplary are paper / polyethylene / aluminum complexes.
- a porous bag containing a desiccant or a desiccant label optionally adhesive.
- the presence of desiccant thus makes it possible to stabilize the testosterone contained in the DTA over storage periods of up to 12 months, or even 24 months, or even 36 months and this by noting that a very weak generation of degradation products of type androstenedione, compared with a control without desiccant.
- the desiccant may be an integral part of the packaging material. As such, it can be distributed at the weld zone between the multilayer films in the case of a bag or between the delaminable lid and the bottom in the case of a blister.
- the transdermal systems containing testosterone concerned by the present invention are any type of DTA.
- the present invention relates more particularly to devices that are called matrix.
- matrix DTA containing testosterone as an active principle mention may be made of the device described in the patent application FR 2793689 in the name of the applicant. This application describes a DTA comprising in the matrix layer an acrylic type polymer having an acid functionality.
- the acid functionality results from the presence of acrylic acid among the basic monomers; it should be understood that this self-adhesive polymer used in the matrix layer has free carboxylic acid side groups.
- this matrix material which a priori is not favorable to maximum stability of testosterone, the addition of polyvinylpyrrolidone has physically stabilized said testosterone.
- the chemical stability of testosterone in the long term is not optimal. It is also the object of the present invention to ensure the long-term chemical stability of testosterone contained in a matrix DTA, in particular in a matrix-type DTA in which the matrix layer comprises a self-adhesive polymer with acid functionality.
- the present invention therefore aims to stabilize the testosterone contained in a DTA, in particular a matrix-type DTA, preferably comprising at least one acid-functional polymer.
- testosterone means testosterone as such or one of its derivatives.
- testosterone derivatives is meant according to the present invention not only its esters, such as, for example, the acetate, enanthate, propionate, isobutyrate, undecanoate and cypionate forms, but also derivatives such as those having a substituent at least in the 6-a position. or 7-a.
- a desiccant in combination with a DTA containing testosterone has thus considerably improved the chemical stability of the testosterone contained in such a device.
- a desiccant of DESIMAX ® type transdermal device as described in the patent application French FR2793689, there has been a decreased androstenedione content by half and other impurities divided by a factor of almost 4 , this compared to a control without desiccant, when stored for 30 months at 25 ° C / 60% Relative Humidity (RH).
- RH Relative Humidity
- the present invention is particularly unexpected and surprising because indeed, it seems difficult to explain the limitation of the oxidation and hydroxylation of testosterone due to the presence of a desiccant within the package containing DTA to testosterone.
- One hypothesis put forward is that the total dehydration of the adhesive matrix containing testosterone makes it possible to significantly reduce the activity of the residual water at this matrix and at the same time reduces the kinetics of formation of the oxidation and hydroxylation products. .
- the present invention more particularly relates to the chemical stabilization of testosterone contained in a self-adhesive matrix-type transdermal device containing at least one acid-functional polymer.
- the presence of desiccant seems to counteract the deleterious effect including acid functions of the polymer.
- compositions in the form of a self-adhesive transdermal device containing testosterone, being disposed in a sealed package together containing a desiccant, said composition being characterized in that after 12 months of storage at 25 ° C. and 60% relative humidity, preferably 24 months, more preferably still
- the amount of androstenedione contained in the device is less than 3% by weight, or even less than
- the transdermal device is a matrix-type device containing at least one acid-functional self-adhesive polymer.
- said acid-functional self-adhesive polymer is a polymer of the (meth) acrylic acid monomer and at least one monomer selected from the group consisting of the monomers
- C6 hexyl (meth) acrylate, vinyl acetate, glycidyl (meth) acrylate, and 2-hydroxy (C1-C6) alkyl (meth) acrylate More preferably still it may be a polymer of the (meth) acrylic acid monomer and at least one monomer selected from the group consisting of the monomers
- acrylic polymer is for example the DUROTAK ® 387-2052 or 87-2052 from National Starch.
- the present invention thus makes it possible to ensure the storage of a DTA containing testosterone packaged in a sealed package and this thanks to the presence of a desiccant within this package.
- This makes it possible to maintain at a temperature of the order of 25 ° C. and at a RH of the order of 60%, DTAs containing testosterone for periods of up to 12, even 24 or even 36 months and this without observing exceeding the threshold of androstenedione content by about 3% by weight of the amount of testosterone.
- Example 1 Results Obtained with a Desiccant Desiccant Label (Desimax ® ) 0.145 g on testosterone-based DTA pilot batches
- A (% androstenedione,% by weight relative to the amount of testosterone) O (% other impurities,% by weight relative to the amount of testosterone)
- compositions CM851E01 and CM852E02 are 2 batches of testosterone-based DTA of the following composition: 69% by weight of a self-adhesive polymer of the monomers acrylic acid, 2-ethylhexylacrylate, vinyl acetate and butyl acrylate, this polymer being crosslinked and having an acid number of between 10 and 70 and a glass transition temperature of between -100 ° C. and -10 ° C.
- DUROTAK 387-2052 15% by weight of DTA, polyvinylpyrrolidone of molecular mass between 44000 and 54000, 11% by weight of DTA, N, N-diethyl-m-toluamide, 5% by weight of DTA, testosterone DTA are packaged in a waterproof pouch consisting of two thermosealed Paper / Aluminum / PolyEthylene tri-layer leaflets. The desiccant label is placed on an inner side of the sachet.
- the use of desiccant DesiMax ® label according to the present invention can significantly reduce the evolution of impurities; for example, at 12 months 30 0 C / 65% RH, and in the absence of Desimax, the mean values of androstenedione and other impurities are respectively 1.9% and 2.17%, by weight of the amount of testosterone . Under the same storage conditions and at the same time, the amounts of androstenedione are reduced by half and the other impurities by about 70%, in the presence of the DesiMax ® desiccant label.
- Example 2 Results obtained with a self-adhesive label-type desiccant Desimax ® 0.145 g on industrial batches of testosterone-based DTA
- A (% androstenedione, in% by weight of the amount of testosterone)
- the compositions 7043524, 7043534, 7043554 and 7043564 are testosterone-based DTAs corresponding to the compositions described according to example 1 and packaged in the same manner as described in example 1.
- the DesiMax ® desiccant label according to the invention also makes it possible to improve the stability of DTA manufactured on an industrial scale. For example, during the first 9 months of stability at 25 ° C / 60% RH, the presence of this label makes it possible to slow down the evolution of the degradation products; the amounts of androstenedione and other impurities decrease by half; the physical stability of the DTAs is excellent.
- Example 3 the use of the DesiMax ® label according to the invention makes it possible to dehydrate DTA almost completely: the initial average water content before packaging (0.8%) drops rapidly to reach a threshold of less than 0 , 1%.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008548013A JP2009522243A (ja) | 2005-12-29 | 2006-12-26 | 経皮デバイス中のテストステロンの安定化 |
CA002635422A CA2635422A1 (fr) | 2005-12-29 | 2006-12-26 | Stabilisation de testosterone au sein de dispositifs transdermiques. |
NZ568658A NZ568658A (en) | 2005-12-29 | 2006-12-26 | Testosterone stabilisation in transdermal devices |
US12/086,964 US20080317859A1 (en) | 2005-12-29 | 2006-12-26 | Stabilization of Testosterone Within Transdermal Devices |
EP06847141A EP1965749A1 (fr) | 2005-12-29 | 2006-12-26 | Stabilisation de testosterone au sein de dispositifs transdermiques |
UAA200809847A UA97354C2 (ru) | 2005-12-29 | 2006-12-26 | Стабилизация тестостерона в устройствах чрескожного воздействия |
AU2006329751A AU2006329751A1 (en) | 2005-12-29 | 2006-12-26 | Testosterone stabilisation in transdermal devices |
BRPI0620839-8A BRPI0620839A2 (pt) | 2005-12-29 | 2006-12-26 | estabilização de testosterona no seio de dispositivos transdérmicos |
IL192406A IL192406A0 (en) | 2005-12-29 | 2008-06-23 | Testosterone stabilisation in transdermal devices |
TNP2008000286A TNSN08286A1 (fr) | 2005-12-29 | 2008-06-27 | Stabilisation de testosterone au sein de dispositifs transdermiques |
NO20083306A NO20083306L (no) | 2005-12-29 | 2008-07-25 | Testosteronstabilisering i transdermale anordninger |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0513435 | 2005-12-29 | ||
FR0513435A FR2895679B1 (fr) | 2005-12-29 | 2005-12-29 | Stabilisation de testosterone au sein de dispositifs transdermiques |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2007074239A1 true WO2007074239A1 (fr) | 2007-07-05 |
Family
ID=37075280
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2006/002873 WO2007074239A1 (fr) | 2005-12-29 | 2006-12-26 | Stabilisation de testosterone au sein de dispositifs transdermiques. |
Country Status (18)
Country | Link |
---|---|
US (1) | US20080317859A1 (fr) |
EP (1) | EP1965749A1 (fr) |
JP (1) | JP2009522243A (fr) |
KR (1) | KR20080081166A (fr) |
CN (1) | CN101351180A (fr) |
AU (1) | AU2006329751A1 (fr) |
BR (1) | BRPI0620839A2 (fr) |
CA (1) | CA2635422A1 (fr) |
FR (1) | FR2895679B1 (fr) |
IL (1) | IL192406A0 (fr) |
MA (1) | MA30015B1 (fr) |
NO (1) | NO20083306L (fr) |
NZ (1) | NZ568658A (fr) |
RU (1) | RU2419436C2 (fr) |
TN (1) | TNSN08286A1 (fr) |
UA (1) | UA97354C2 (fr) |
WO (1) | WO2007074239A1 (fr) |
ZA (1) | ZA200805157B (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20180153904A1 (en) | 2010-11-30 | 2018-06-07 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
US9034858B2 (en) | 2010-11-30 | 2015-05-19 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
US20170246187A1 (en) | 2014-08-28 | 2017-08-31 | Lipocine Inc. | (17-ß)-3-OXOANDROST-4-EN-17-YL TRIDECANOATE COMPOSITIONS AND METHODS OF THEIR PREPARATION AND USE |
WO2018098501A1 (fr) | 2016-11-28 | 2018-05-31 | Lipocine Inc. | Traitement oral à base d'undécanoate de testostérone |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19517145C1 (de) * | 1995-05-10 | 1996-11-28 | Hexal Pharmaforschung Gmbh | Transdermales therapeutisches System (TTS) zur Verabreichung von Testosteron |
US5698217A (en) * | 1995-05-31 | 1997-12-16 | Minnesota Mining And Manufacturing Company | Transdermal drug delivery device containing a desiccant |
WO1998024393A1 (fr) * | 1996-12-03 | 1998-06-11 | Minnesota Mining And Manufacturing Company | Distributeurs de timbres transdermiques/transmuqueux |
WO1999015156A1 (fr) * | 1997-09-25 | 1999-04-01 | Ethical Pharmaceuticals South America S.A. | Inhibition de la cristallisation dans des dispositifs transdermiques |
FR2793689A1 (fr) * | 1999-05-19 | 2000-11-24 | Pf Medicament | Dispositif transdermique pour l'administration de testosterone ou d'un de ses derives |
WO2000074933A1 (fr) * | 1999-06-04 | 2000-12-14 | Lts Lohmann Therapie-Systeme Ag | Stratifie composite et son procede de fabrication |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5656286A (en) * | 1988-03-04 | 1997-08-12 | Noven Pharmaceuticals, Inc. | Solubility parameter based drug delivery system and method for altering drug saturation concentration |
DE19913761B4 (de) * | 1999-03-26 | 2005-02-10 | Lts Lohmann Therapie-Systeme Ag | Trocknungsvorrichtung und Verfahren zu ihrer Herstellung sowie ihre Verwendung |
US6905016B2 (en) * | 2000-03-14 | 2005-06-14 | Noven Pharmaceuticals, Inc. | Packaging system for transdermal drug delivery systems |
-
2005
- 2005-12-29 FR FR0513435A patent/FR2895679B1/fr not_active Expired - Fee Related
-
2006
- 2006-12-26 BR BRPI0620839-8A patent/BRPI0620839A2/pt not_active IP Right Cessation
- 2006-12-26 JP JP2008548013A patent/JP2009522243A/ja active Pending
- 2006-12-26 WO PCT/FR2006/002873 patent/WO2007074239A1/fr active Application Filing
- 2006-12-26 RU RU2008131064/15A patent/RU2419436C2/ru not_active IP Right Cessation
- 2006-12-26 NZ NZ568658A patent/NZ568658A/en not_active IP Right Cessation
- 2006-12-26 EP EP06847141A patent/EP1965749A1/fr not_active Withdrawn
- 2006-12-26 US US12/086,964 patent/US20080317859A1/en not_active Abandoned
- 2006-12-26 CN CNA2006800495563A patent/CN101351180A/zh active Pending
- 2006-12-26 AU AU2006329751A patent/AU2006329751A1/en not_active Abandoned
- 2006-12-26 UA UAA200809847A patent/UA97354C2/ru unknown
- 2006-12-26 CA CA002635422A patent/CA2635422A1/fr not_active Abandoned
- 2006-12-26 KR KR1020087016196A patent/KR20080081166A/ko not_active Application Discontinuation
-
2008
- 2008-06-02 MA MA30982A patent/MA30015B1/fr unknown
- 2008-06-12 ZA ZA200805157A patent/ZA200805157B/xx unknown
- 2008-06-23 IL IL192406A patent/IL192406A0/en unknown
- 2008-06-27 TN TNP2008000286A patent/TNSN08286A1/fr unknown
- 2008-07-25 NO NO20083306A patent/NO20083306L/no not_active Application Discontinuation
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19517145C1 (de) * | 1995-05-10 | 1996-11-28 | Hexal Pharmaforschung Gmbh | Transdermales therapeutisches System (TTS) zur Verabreichung von Testosteron |
US5698217A (en) * | 1995-05-31 | 1997-12-16 | Minnesota Mining And Manufacturing Company | Transdermal drug delivery device containing a desiccant |
WO1998024393A1 (fr) * | 1996-12-03 | 1998-06-11 | Minnesota Mining And Manufacturing Company | Distributeurs de timbres transdermiques/transmuqueux |
WO1999015156A1 (fr) * | 1997-09-25 | 1999-04-01 | Ethical Pharmaceuticals South America S.A. | Inhibition de la cristallisation dans des dispositifs transdermiques |
FR2793689A1 (fr) * | 1999-05-19 | 2000-11-24 | Pf Medicament | Dispositif transdermique pour l'administration de testosterone ou d'un de ses derives |
WO2000074933A1 (fr) * | 1999-06-04 | 2000-12-14 | Lts Lohmann Therapie-Systeme Ag | Stratifie composite et son procede de fabrication |
Non-Patent Citations (3)
Title |
---|
MULTISORB TECHNOLOGIES: "DesiMax", 15 December 2005 (2005-12-15), pages 1 - 1, XP002407122, Retrieved from the Internet <URL:http://web.archive.org/web/20051215145150/www.saddleform.com/applications/products/desiccants/labels/desimax_html> [retrieved on 20061113] * |
MULTISORB TECHNOLOGIES: "Pharmaceutical/Diagnostic", 18 December 2005 (2005-12-18), pages 1 - 1, XP002407121, Retrieved from the Internet <URL:http://web.archive.org/web/20051218003820/http://multisorb.com/applications/pharmaceutical_html> [retrieved on 20061113] * |
RX LIST THE INTERNET DRUG INDEX: "testosterone (transdermal)", 28 December 2005 (2005-12-28), pages 1 - 2, XP002407120, Retrieved from the Internet <URL:http://web.archive.org/web/20051228151044/http://www.rxlist.com/cgi/generic2/testod.htm> [retrieved on 20061113] * |
Also Published As
Publication number | Publication date |
---|---|
EP1965749A1 (fr) | 2008-09-10 |
RU2419436C2 (ru) | 2011-05-27 |
KR20080081166A (ko) | 2008-09-08 |
AU2006329751A1 (en) | 2007-07-05 |
CA2635422A1 (fr) | 2007-07-05 |
FR2895679B1 (fr) | 2012-06-08 |
ZA200805157B (en) | 2009-06-24 |
NO20083306L (no) | 2008-09-16 |
FR2895679A1 (fr) | 2007-07-06 |
US20080317859A1 (en) | 2008-12-25 |
UA97354C2 (ru) | 2012-02-10 |
MA30015B1 (fr) | 2008-12-01 |
IL192406A0 (en) | 2008-12-29 |
CN101351180A (zh) | 2009-01-21 |
JP2009522243A (ja) | 2009-06-11 |
RU2008131064A (ru) | 2010-02-10 |
NZ568658A (en) | 2011-10-28 |
TNSN08286A1 (fr) | 2009-10-30 |
BRPI0620839A2 (pt) | 2011-11-29 |
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