EP0741572A1 - SUBSTANCE POUR APPLICATION TRANSDERMIQUE CONTENANT DU 14$g(a),17$g(a)-ETHANOESTRA-1,3,5(10)-TRIENE-3,17$g(b)-DIOL - Google Patents

SUBSTANCE POUR APPLICATION TRANSDERMIQUE CONTENANT DU 14$g(a),17$g(a)-ETHANOESTRA-1,3,5(10)-TRIENE-3,17$g(b)-DIOL

Info

Publication number
EP0741572A1
EP0741572A1 EP94905711A EP94905711A EP0741572A1 EP 0741572 A1 EP0741572 A1 EP 0741572A1 EP 94905711 A EP94905711 A EP 94905711A EP 94905711 A EP94905711 A EP 94905711A EP 0741572 A1 EP0741572 A1 EP 0741572A1
Authority
EP
European Patent Office
Prior art keywords
triene
diol
gestagen
agent
ethanoestra
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.)
Withdrawn
Application number
EP94905711A
Other languages
German (de)
English (en)
Inventor
Clemens Günther
Ralph Lipp
Ulrich Täuber
Jutta Riedl
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.)
Bayer Pharma AG
Original Assignee
Schering 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
Application filed by Schering AG filed Critical Schering AG
Publication of EP0741572A1 publication Critical patent/EP0741572A1/fr
Withdrawn legal-status Critical Current

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
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
    • A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
    • A61K9/7061—Polyacrylates
    • 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
    • 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
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • 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
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
    • A61K9/7069—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. polysiloxane, polyesters, polyurethane, polyethylene oxide
    • 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
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7084—Transdermal patches having a drug layer or reservoir, and one or more separate drug-free skin-adhesive layers, e.g. between drug reservoir and skin, or surrounding the drug reservoir; Liquid-filled reservoir patches

Definitions

  • the invention relates to an agent for transdermal application, characterized in that it contains 14 ⁇ , 17 ⁇ -ethanoestra-l, 3,5 (10) -triene-3,17ß-diol, optionally in combination with one or more gestagen (s).
  • transdermally administered drugs have the advantage that they enable a more uniform release of the active ingredient over a longer period of time than is usually possible with agents to be administered differently, such as orally. These properties can be used to advantage in a number of endocrine diseases. For steroid hormones that are difficult to dissolve in water, such as, for example, estrogens, it is generally quite problematic to create transdermal systems which ensure sufficient penetration of the active ingredient through the skin for therapy.
  • Suitable gestagens for the agent according to the invention are, for example, norethisterone, levonorgestrel, gestodene, 3-keto-desogestrel and their esters.
  • the combination preparations according to the invention preferably contain 1 to 3 - in particular 1 to 2 gestagen (s).
  • the active ingredient or the active ingredient mixture can be dissolved or suspended in suitable volatile solvents and / or penetration-enhancing agents.
  • the solutions or suspensions obtained can be mixed with the usual auxiliaries, such as matrix formers and bactericides and, if appropriate, filled into conventional metering containers after sterilization.
  • auxiliaries such as matrix formers and bactericides
  • Suitable volatile solvents are, for example, lower alcohols, ketones or lower carboxylic acid esters such as ethanol, isopropanol, acetone or ethyl acetate, polar ethers such as tetrahydrofuran, lower hydrocarbons such as cyclohexane or petrol or else halogenated hydrocarbons such as dichloromethane, trichloromethane, trichlorotrifluoromethane and trichloromethane. There is no need to explain that mixtures of these solvents are also suitable.
  • Suitable penetration-enhancing agents are, for example, monohydric or polyhydric alcohols, such as ethanol, 1,2-propanediol or benzyl alcohol, saturated and unsaturated fatty alcohols with 8 to 18 carbon atoms, such as lauryl alcohol or cetyl alcohol, hydrocarbons such as mineral oil, saturated and unsaturated fatty acids with 8 to 18 Carbon atoms, such as stearic acid or oleic acid, fatty acid esters with up to 24 carbon atoms or dicarboxylic acid diesters with up to 24 carbon atoms.
  • monohydric or polyhydric alcohols such as ethanol, 1,2-propanediol or benzyl alcohol
  • saturated and unsaturated fatty alcohols with 8 to 18 carbon atoms such as lauryl alcohol or cetyl alcohol
  • hydrocarbons such as mineral oil
  • saturated and unsaturated fatty acids with 8 to 18 Carbon atoms such as stearic acid or oleic acid
  • Fatty acid esters which are suitable for the agent according to the invention are, for example, those of acetic acid, caproic acid, lauric acid, myristic acid, stearic acid and palmitic acid, such as, for example, the methyl esters, ethyl esters, propyl esters, isopropyl esters, butyl esters, sec-butyl esters, isobutyl esters or tert. -Butyl esters of these acids.
  • Particularly preferred esters are those of myristic acid, such as their methyl ester and in particular their isopropyl ester.
  • Suitable dicarboxylic acid diesters are, for example, diisopropyl adipate, diisobutyl adipate and diisopropyl sebacate.
  • Further penetration-enhancing agents are phosphatidyl derivatives such as lecithin, terpenes, amides, ketones, urea and its derivatives or ethers such as diethylene glycol monoethyl ether. No further explanation is required that mixtures of these penetration-enhancing agents are also suitable for producing agent a according to the invention.
  • the concentration at which the active compound or mixture of active compounds is optimally dissolved or suspended in the solvent is usually 0.01 to 25 for 14 ⁇ , 17 ⁇ -ethanoestral, 3.5 (10) -triene-3,17ß-diol Percent by weight.
  • concentration naturally depends on the type of active ingredient used and the desired single dose; in individual cases, it must be determined using selected preliminary agents, such as the determination of the achievable blood plasma concentrations of active ingredient, for selected agents according to the invention become.
  • active substance concentrations of 0.01 to 25 percent by weight of estrogen in the agent according to the invention will also be sufficient here.
  • the weight ratio of 14, 17 -thanoestra-l, 3,5 (10) -triene-3,17ß-diol to the progestogen (s) for the combination preparations is 5: 1 to 1:20.
  • the therapeutically required transdermal daily dose for 14 ⁇ , 17 ⁇ -ethanoestral, 3.5 (10) -triene-3.17ß-diol is a maximum of 250 ⁇ g; thus, with a TTS area of 25 cm 2, an average percutaneous flow of 420 ng / cm 2 / hour is required. In vitro studies using suitable formulations have shown that this can be exceeded by about 10 times with the agents according to the invention.
  • transdermal therapeutic systems are those which are usually used for the percutaneous application of active substances (Yie W. Chien: “Transdermal Controlled Systemic Medications", Marcel Dekker, Inc., New York and Basel, 1987, Dr. Richard Baker: "Analysis of Transdermal Drug Delivery Patents 1934 to 1984 "and” Analysis of Recent Transdermal Delivery Patents, 1984-1986 and Enhancers "Membrane Technology & Research 1030 Hamilton Court Menlo Park CA 94025 (415) 328-2228).
  • transdermal therapeutic system which consists of a) an impermeable top layer, one to three adhering to the top layer, the 14 ⁇ , 17 ⁇ -ethanoestra-l, 3,5 (10) -triene-3,17ß-diol optionally containing the progestogen (s) and, if desired, penetration-enhancing agents , for these components permeable self-adhesive matrix layer (s) or a peelable protective layer covered or surrounded by a skin pressure-sensitive adhesive if desired containing penetration-enhancing agents, or
  • a pressure-sensitive adhesive provided with a penetration-enhancing agent, if desired, one to three (each) leaving a pressure-sensitive adhesive border uncovered and fastened by means of a cover to the pressure-sensitive adhesive, the 14 ⁇ , 17 ⁇ -ethanoestra-l, 3.5 (10) -triene 3,17ß-diol, optionally containing the gestagen (s) and penetration-enhancing matrix layer (s) and a removable protective layer, or
  • an impermeable cover layer one to three on or in the cover layer, the 14 ⁇ , 17 ⁇ -ethanoestral, 3,5 (10) -triene-3,17ß-diol, optionally the gestagen (s) and if desired pharmaceutical reservoir (s) containing penetration-enhancing agents, one to three polymer layer (s) permeable to these components, a permeable skin pressure-sensitive adhesive layer optionally containing penetration-enhancing agents and a removable protective layer.
  • a transdermal therapeutic system according to variant a) represents a simple matrix system. It can be round, oval or rectangular in shape, for example, and can be produced as follows.
  • Suitable solvents and penetration-enhancing agents are, for example, the liquids of this type already mentioned.
  • Suitable medically customary adhesives are, for example, polyacrylates, silicones, polyurethanes, block polymers, styrene-butadiene copolymers and natural or synthetic rubbers.
  • Cellulose ethers, polyvinyl compounds or silicates come into consideration as further matrix formers.
  • the usual additives, such as tackifying resins and oils can be added to the matrix obtained.
  • All films that are commonly used in transdermal therapeutic systems are suitable as a protective layer. Such films are siliconized or fluoropolymer coated, for example.
  • 10 to 100 ⁇ m thick films made of polyethylene or polyester can be used as a top layer, optionally pigmented or metallized.
  • the drug layer applied thereon preferably has a thickness of 20 to 500 ⁇ m.
  • the active ingredients are preferably dispensed over an area of 5 to 100 cm 2 .
  • the 14 ⁇ , 17-ethanoestra-1,3,5 (10) -triene-3,17 ⁇ -diol and, if appropriate, the penetration enhancers can be introduced into the matrix applied to the impermeable cover layer, while the layer or layers underneath which contains estrogens and possibly also penetration enhancers.
  • the penetration enhancers can be introduced into the matrix applied to the impermeable cover layer, while the layer or layers underneath which contains estrogens and possibly also penetration enhancers.
  • a transdermal therapeutic matrix system according to variant b can, for example, also be round, oval or rectangular and can be produced as follows.
  • a cover is coated with a skin pressure sensitive adhesive. Then you glue one to three punched-out areas of this with a non-permeable cover, the 14 ⁇ , 17 ⁇ -ethanoestra-l, 3,5 (10) -triene-3,17ß-diol, optionally the gestagen (s) (e ) and penetration-enhancing agents containing matrix layers so that the cover has a sufficient edge for attachment to the skin and at Several areas also have sufficient gaps and provide them with a removable protective layer.
  • the materials used in this matrix system can be the same as those in variant a.
  • a transdermal therapeutic reservoir system according to variant c can, for example, also be round, oval or rectangular and can be represented as follows;
  • An impermeable film is deformed by heat and / or tension so that one to three 0.1 to 3 ml bulges are formed.
  • This is filled with an active ingredient-containing solution or suspension containing 1-50 percent by weight of active ingredient or mixture of active ingredients with a penetration-enhancing agent.
  • the active ingredient-containing solution or suspension can also be thickened with up to 10 percent by weight of matrix former.
  • a welded-on or glued-on permeable polymer layer serves to cover the reservoir towards the skin, to which a permeable skin pressure-sensitive adhesive layer and a removable protective layer are applied.
  • the above-mentioned penetration enhancing agents can be used in this system.
  • a 20 to 200 ⁇ m thick film made of cellulose esters, cellulose ethers, silicones or polyolefin compounds is used as the permeable polymer layer.
  • the diffusion rate of the active ingredient or mixture of active ingredients can be varied within wide limits by varying this polymer layer.
  • the active ingredient-containing matrix systems or drug reservoirs can contain not only different active ingredients but additionally also different penetration-enhancing agents.
  • the Marix systems according to variant a or b a sufficient distance between the areas must be ensured in order to prevent diffusion of the active substances into the other area.
  • the reservoir systems according to variant c it is possible to provide the individual reservoirs with differently permeable polymer layers in order to adapt the diffusion flow of the individual active ingredients to the respective needs.
  • FIG. 1 shows a cross section through a simple round matrix system according to variant a without the removable protective layer. It consists of the impermeable cover layer 1 and the drug-containing matrix layer 2.
  • Fig. 2 shows a cross section through a matrix system according to variant b without the removable protective layer.
  • Fig. 3 shows the supervision of this system.
  • the system consists of the cover 3, which is provided with a pressure-sensitive adhesive layer 4.
  • Two drug-containing matrix layers 6 and 8 are attached to this pressure-sensitive adhesive layer by means of impervious covers 5 and 7.
  • FIG 4 shows a cross section through a round single-chamber reservoir system according to variant c without the removable protective layer. It consists of the impermeable cover layer 9, the drug reservoir 10, the permeable polymer layer 11 and the skin pressure-sensitive adhesive layer 12.
  • FIG. 5 shows a cross section through a round two-chamber reservoir system according to variant c without the removable protective layer. It consists of the impermeable cover layer 13, the two semicircular drug reservoirs 14 and 15, the permeable polymer layer 16 and the skin pressure-sensitive adhesive layer 17.
  • An emulsion gel for transdermal application consists, for example, of the active ingredient or mixture of active ingredients, penetration-enhancing agents, emulsifiers (where ambiphilic representatives of the penetration-enhancing agents can serve as emulsifiers) and, if appropriate, matrix formers.
  • a typical recipe consists of 0.1 - 25 % By weight of active ingredient or mixture of active ingredients, 0-10% by weight of emulsifier, 0-5% by weight of matrix former, 0 to 50% by weight of penetration-enhancing agents and water at 100% by weight.
  • the agent is emulsified in the usual way and, if necessary, the usual antioxidants, preservatives, etc. are added.
  • Single-phase gels are obtained, for example, by dissolving or suspending the active ingredient or the active ingredient mixture in solvents such as water, lower alcohols or mixtures thereof, optionally with the addition of penetration-enhancing agents and thickening with matrix formers.
  • Typical formulations for such gels contain 0.01-25 percent by weight of active ingredient or mixture of active ingredients, 1-20 percent by weight of matrix former, 0 to 40 percent by weight of penetration-enhancing agents supplemented with the solvent to 100 percent by weight.
  • these gels can also contain antioxidants, preservatives, etc.
  • a typical spray formulation is, for example:
  • the blowing agent can be dispensed with.
  • the 14 ⁇ , 17 ⁇ -ethanoestra-1,3,5 (10) -triene-3,17ß-diol-containing agents according to the invention for transdermal application can be used to treat the same diseases as the previously known agents, for example to be administered orally which contain highly effective estrogens.
  • the preparations containing progestin, if any, according to the invention can also be used to prevent conception.
  • the agents according to the invention have particular advantages in the treatment of diseases which require long-term treatment with a relatively high dosage of the active ingredients.
  • the application frequency can be reduced significantly and a substantially uniform blood plasma gel can be achieved. It is also advantageous that gastrointestinal side effects are not to be expected and the first passage through the liver is avoided.
  • progestogen-free monotherapeutics of the present invention appear particularly suitable.
  • hormone replacement therapy for menopausal symptoms, atrophic vaginitis, caurosis vulvae, treatment of estrogen-dependent tumors for osteoporosis prophylaxis or treatment, or for the treatment of other diseases for which estrogen substitution is indicated.
  • transdermal use of progestogens in sequential or continuous combination with 14, 17 ⁇ -ethanoestra-l, 3,5 (10) -triene-3,17ß-diol offers particular advantages, for example for the treatment of menopausal symptoms, for the prevention of osteoporosis, for cycle regulation and for cycle stabilization, transdermal contraception and for the treatment of other diseases in which a combined estrogen / progestogen replacement is indicated.
  • Polyester film 0.074 mm thick (Skotchpak ®1009 from the manufacturer 3M; polypropylene film (Celgard ®2500) from the manufacturer Celanese, liner film Skotchpak® 1022 and 1360 from the manufacturer 3M; transfer adhesive 9871 from the manufacturer 3M, polyacrylate adhesive of the type Sichello ® J 6610-21 made by Henkel KG, polyacrylate adhesive type Gelva ®788 made by Monsanto, silicone adhesive type X-7-2960 made by Dow Corning and hydroxypropyl cellulose type Klucel ®HXF made by Hercules.
  • the mixture is applied to polyester film by means of a coating device in such a way that, after removal of the volatile solvent, a uniform film of 40 g / m 2 of solids is formed. It is then laminated with a fluoropolymer-coated polyester liner.
  • the laminate thus obtained is divided into round individual plasters with an area of 10 cm 2 by means of a punching device and packed in aluminum foil.
  • Fig. 1 shows a cross section through this plaster without polyester liner. The patch adheres to the skin after the liner film has been removed.
  • the content determination gives an even distribution of active ingredient of 0.08 mg / cm 2 on average.
  • the solution is applied to polyester film by means of a coating device in such a way that, after removal of the volatile solvents, a uniform film of 100 g / m 2 of solids is formed. It is then laminated with a siliconized, active ingredient-free liner film.
  • the laminate obtained in this way is divided into individual plasters with an area of 10 cm 2 by means of a punching device and packed in aluminum foil. The patch adheres to the skin after the liner film has been removed.
  • the content of 14 ⁇ , 17 -thanoestra-1,3,5 (10) -triene-3,17ß-diol is on average 0.5 mg / cm 2 . ⁇
  • the mixture is applied to polyester film by means of a coating device in such a way that, after removal of the volatile solvents, a uniform film of 70 g / m 2 of solids is formed. It is then laminated with a siliconized, active ingredient-free liner film.
  • the laminate obtained in this way is divided into individual plasters with an area of 10 cm 2 by means of a punching device and packed in aluminum foil. The patch adheres to the skin after the liner film has been removed.
  • the matrix system I consists of the matrix layer 8 provided with a polyester film 7 of the following composition
  • the matrix system II consists of the matrix layer 6 provided with a polyester film 5 of the following composition 2.0 mg gestoden
  • Both matrix systems are glued to a cover film coated with skin pressure sensitive adhesive, as shown in FIG. 3. After lamination and punching out, plasters of the type shown in FIGS. 2 and 3 are produced.
  • a 7.4 cm diameter polyester film is deformed by means of tension and heat so that a round bulge of 10 cm 2 area is formed. This is mixed with 1 ml of a suspension of
  • Fig. 4 shows a cross section through a plaster of this type without a liner.
  • Example 5 Analogously to Example 5, a polyester film is deformed in such a way that two semicircular bulges, each separated by a web, of 7.5 cm 2 in area are formed.
  • Reservoir I is filled with 0.75 ml of a suspension of
  • Fig. 5 shows a cross section through such a plaster without a liner.
  • the salary reduction results in a homogeneous active ingredient distribution in the gel with values of 95% at 105% of the target value.

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

Abstract

Cette substance pour application transdermique se caractérise par le fait qu'elle contient du 14 alpha ,17 alpha -éthanoestra-1,3,5(10)-triène-3,17 beta -diol, en association avec un ou deux progestatif(s) le cas échéant.
EP94905711A 1994-01-27 1994-01-27 SUBSTANCE POUR APPLICATION TRANSDERMIQUE CONTENANT DU 14$g(a),17$g(a)-ETHANOESTRA-1,3,5(10)-TRIENE-3,17$g(b)-DIOL Withdrawn EP0741572A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP1994/000213 WO1995020392A1 (fr) 1994-01-27 1994-01-27 SUBSTANCE POUR APPLICATION TRANSDERMIQUE CONTENANT DU 14α,17α-ETHANOESTRA-1,3,5(10)-TRIENE-3,17β-DIOL

Publications (1)

Publication Number Publication Date
EP0741572A1 true EP0741572A1 (fr) 1996-11-13

Family

ID=8165820

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94905711A Withdrawn EP0741572A1 (fr) 1994-01-27 1994-01-27 SUBSTANCE POUR APPLICATION TRANSDERMIQUE CONTENANT DU 14$g(a),17$g(a)-ETHANOESTRA-1,3,5(10)-TRIENE-3,17$g(b)-DIOL

Country Status (6)

Country Link
EP (1) EP0741572A1 (fr)
JP (1) JPH09510697A (fr)
AU (1) AU5971294A (fr)
FI (1) FI962993A (fr)
NO (1) NO963128D0 (fr)
WO (1) WO1995020392A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19526864A1 (de) * 1995-07-22 1997-01-23 Labtec Gmbh Hormonpflaster
AU2002340659B2 (en) * 2001-11-09 2008-04-10 Qlt Inc. Photodynamic therapy for the treatment of hair loss

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4883669A (en) * 1985-02-25 1989-11-28 Rutgers, The State University Of New Jersey Transdermal absorption dosage unit for estradiol and other estrogenic steroids and process for administration
CH674618A5 (fr) * 1987-04-02 1990-06-29 Ciba Geigy Ag
HU210549B (en) * 1988-10-27 1995-05-29 Schering Ag Process for producing transdermally applicable pharmaceutical composition containing gestodene
DE3838779A1 (de) * 1988-11-11 1990-05-17 Schering Ag 14(alpha),17(alpha)-ethano-estratriene
DE4227989A1 (de) * 1992-08-21 1994-06-09 Schering Ag Mittel zur transdermalen Applikation enthaltend 3-Keto-desogestrel

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9520392A1 *

Also Published As

Publication number Publication date
AU5971294A (en) 1995-08-15
NO963128L (no) 1996-07-26
NO963128D0 (no) 1996-07-26
FI962993A0 (fi) 1996-07-26
WO1995020392A1 (fr) 1995-08-03
FI962993A (fi) 1996-07-26
JPH09510697A (ja) 1997-10-28

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