WO2012007150A1 - Système thérapeutique transdermique doté d'un inhibiteur de la cholinestérase - Google Patents

Système thérapeutique transdermique doté d'un inhibiteur de la cholinestérase Download PDF

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Publication number
WO2012007150A1
WO2012007150A1 PCT/EP2011/003473 EP2011003473W WO2012007150A1 WO 2012007150 A1 WO2012007150 A1 WO 2012007150A1 EP 2011003473 W EP2011003473 W EP 2011003473W WO 2012007150 A1 WO2012007150 A1 WO 2012007150A1
Authority
WO
WIPO (PCT)
Prior art keywords
transdermal therapeutic
therapeutic system
acrylate
reservoir
active ingredient
Prior art date
Application number
PCT/EP2011/003473
Other languages
German (de)
English (en)
Inventor
Katalin Tisa Bostedt
Tobias Pfaller
Wolf-Dieter Vogel
Susanne Lang
Original Assignee
Amw Gmbh
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 Amw Gmbh filed Critical Amw Gmbh
Publication of WO2012007150A1 publication Critical patent/WO2012007150A1/fr

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Classifications

    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • 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
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • 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
    • 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
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7076—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising ingredients of undetermined constitution or reaction products thereof, e.g. rosin or other plant resins
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia

Definitions

  • EP 1 047 409 B1, WO 99/34 782 and the Exelon® patch provide, for example, alpha-tocopherol.
  • the antioxidant alpha-tocopherol is described in the literature as causing allergic contact dermatitis. For example, refer to Dermatitis 2010 June 21 (3): 148-53 (Kosari, P., Alikhan, A., Sockolov, M.
  • DE 38 05 744 C2 and DE 38 44 992 B4 describe the use of the S - (-) - enantiomer of rivastigmine and one of its salts for systemic transdermal
  • EP 1 171 104 B1 and WO 00/64 418 describe a transdermal therapeutic matrix or a reservoir system with a basic or neutral active substance, for example
  • CONFIRMATION COPY Rivastigmine as well as a fully or partially neutralized acidic pressure-sensitive polyacrylate adhesive.
  • EP 2 292 219 A1 EP 1 959 937 and EP 2 286 802 describe a transdermal
  • WO 2011/076 621 A2 describes a transdermal therapeutic system with rivastigmine as the active ingredient in a reservoir with a polymer matrix which has neither hydroxyl nor carboxyl groups.
  • DE 698 30 095 T2 (priority 11. 04. 1997) describes a cosmetic or dermo-pharmaceutical patch for releasing a present in the form of particles water-soluble drug and additionally dissolved in an oil fat-soluble drug in the epidermis [0001].
  • avocado oil is also proposed by DE 198 82 916 Tl (priority 28. 12. 1997) (page 7) also in a list of oils for skin care and skin protection, but here in a gel composition.
  • the device for dispensing cosmetic active ingredients described in DE 199 11 262 A1 can also use the avocado oil, which in turn is listed in a large list of oils.
  • DE 600 28 642 T2 discloses avocado oil in a comprehensive list of oils for incorporation of a solubilized active substance, namely for a plaster containing magnetic particles, which inhibits the penetration of the active ingredient into the Promote skin [0009], wherein the plaster on the skin to achieve a cosmetic effect and / or a pharmaceutical treatment is to be performed [0001].
  • the object of the invention is a transdermal therapeutic system for the treatment of mild to moderate dementia of the type of Alzheimer's disease and containing a carbamate-type cholinesterase inhibitor such as rivastigmine for the treatment of mild-to-moderate dementia of the Alzheimer's type Disease.
  • the transdermal therapeutic system should (1) circumvent the frequent to very common side effects associated with oral administration, especially nausea, diarrhea, and vomiting. (2) Also, the transdermal therapeutic system should have better compliance than oral dosage forms. (3) Thus, the transdermal therapeutic system should allow a comfortable application to the skin and (4) provide good skin compatibility with good comfort and sufficient adhesive power. In addition, it should provide (5) high storage stability and (6) reliable performance. (7) The transdermal therapeutic system should be inexpensive to manufacture. (8) It should be usable for prolonged continuous release of active substances, in particular 1 to 7 days. (9) Finally, the transdermal therapeutic system without antioxidant should be provided.
  • the subject of the invention is now a transdermal therapeutic system
  • a drug-free adhesive layer is a layer that has not been loaded with active ingredient during manufacture.
  • its underlying object is achieved by a transdermal therapeutic system (TDS) with an optional avocado oil content.
  • TDS transdermal therapeutic system
  • a carbamate-type cholinesterase inhibitor such as rivastigmine a skin permeation can be achieved with which plasma levels can be achieved, the one
  • avocado oil and / or the palm oil act as cohesive, solubilizer and / or skin compatibility improver.
  • the active ingredient may also be provided as a physiologically acceptable salt, hydrate, solvate or derivative.
  • rivastigmine and / or at least one other carbamate-type cholinesterase inhibitor may be provided for the transdermal therapeutic system.
  • the transdermal therapeutic system of the invention may comprise one or more carbamate-type cholinesterase inhibitors, rivastigmine being that active agent or one of these agents.
  • the active ingredients can be dissolved in the active substance reservoir or homogeneously dispersed.
  • an active ingredient concentration of 0.1 to 40 and especially to 50 wt .-% and preferably 0.1 to 40 wt .-% (based on the total weight of the drug reservoir) may be provided.
  • an active compound concentration of 15 to 35 wt .-% and in particular about 30 wt .-% (based on the total weight of the drug reservoir) may be provided.
  • the at least one carbamate-type cholinesterase inhibitor may be dissolved in the drug reservoir or dispersed homogeneously.
  • avocado oil and / or palm oil (based on the total weight of the oil) may contain from 0 to 15% by weight
  • Drug reservoirs may be provided.
  • the transdermal therapeutic system according to the invention may have a content of avocado oil and / or palm oil and an additional content of at least one further optional adjuvant, which contributes, for example, to opatisionsverêtung or to solubility improvement, in particular to improved solubility of the active ingredient.
  • the avocado oil and / or palm oil and the optional additional adjuvant can be dissolved in the active substance reservoir or homogeneously dispersed.
  • the active substance reservoir and / or the optional adhesive layer may comprise a pressure-sensitive polymer, in particular from the group of polyacrylates, silicones, block copolymers, polyisobutylenes, acrylate-hydrocarbon graft copolymers, in particular acrylate rubber graft copolymers, or comprise or consist of a pressure-sensitive mixture of several of these polymers.
  • the polyacrylate may, for example, be uncrosslinked polyacrylate and, in particular, uncrosslinked polyacrylate having carboxyl groups, such as DuroTak DT 87-235A.
  • Such uncrosslinked polyacrylate may be present, for example, in admixture with an uncrosslinked acrylate copolymer, for example a
  • Butyl methacrylate / methyl methacrylate copolymer such as Plastoid B.
  • the drug reservoir and / or the optional adhesive layer can be an acrylate [poly (ethylene butylene)] graft copolymer, acrylate [poly (ethylene propylene)] graft copolymer or acrylate- [poly (ethylene-butylene-propylene)] graft copolymer as acrylate-hydrocarbon graft copolymer or styrene-butadiene-styrene as block copolymer or consist thereof.
  • Acrylate hydrocarbon graft copolymers or acrylate rubber graft copolymers are known, for example, from US 5 625 005, US 6 642 298, US 6 670 417 and US 2020/0 068 515 Al.
  • a hydroxyl-functionalized acrylate polymer as the grafting base of the grafted hydrocarbon of the graft copolymer and or
  • a poly (ethylene-butylene) -macromer as a grafted hydrocarbon, in particular a Mw of about 4000 to 7200 (weight average),
  • transdermal therapeutic system of the invention for the drug reservoir and / or the optional adhesive layer
  • the poly (ethylene-butylene) macromers have terminal acrylic or acrylate groups and / or
  • acrylate hydrocarbon graft copolymers to be used according to the invention are an acrylate polymer having hydroxyl functional groups
  • Methacrylate groups (weight average Mw of macromolecular weight about 4000 to 7200), in particular an acrylate-hydrocarbon graft copolymer (hybrid adhesive) according to US 2010/0 068 515 AI Example 2 Sample B (weight average Mw of macromolecular weight about 4000 to 7200).
  • the acrylate-hydrocarbon graft copolymer may be modified with a natural or synthetic hydrocarbon-based tackifier.
  • adhesives include EP 0 836 506 B1 (eg [0016]), WO 95/018 603 A (eg pages 30-31) and US 2010/0 068 515 A1 (eg [0038] to [0039]).
  • the transdermal therapeutic system of the invention may have a content of a solubilizer, in particular a content of 1, 2-propanediol, dimethylacetamide and / or N-methylpyrrolidone.
  • the transdermal therapeutic system according to the invention may have a content of cohesion promoter, in particular a content of polysiloxane.
  • the transdermal therapeutic system according to the invention may have a content of adhesion promoter, in particular a content of one or more resins of natural or synthetic origin.
  • the transdermal therapeutic system according to the invention may have a content of a permeation enhancer.
  • the transdermal therapeutic system of the present invention need not have an antioxidant content, and thus may be free thereof, for example, when the drug reservoir comprises or consists of a carboxyl-containing uncrosslinked polyacrylate such as DuroTak DT 87-235A.
  • transdermal therapeutic system of the present invention can be adjusted for drug skin permeation in vitro from 10 ⁇ g (micrograms) / (hr and system) to 5 mg / hr and system.
  • the level of active ingredient may be adjusted to a continuous release of active ingredient for a period of whole days ranging from 1 to 7 days.
  • the transdermal therapeutic system according to the invention can be provided with an active ingredient-containing basis weight or with a weight of the active substance-containing surface or a weight per unit area of the active substance reservoir of 30 to 150 g / m 2 .
  • the transdermal therapeutic system according to the invention may have a skin-facing active substance-free layer, which may be provided with a basis weight of 10 to 40 g / m 2 and in particular 10 to 30 g / m 2 .
  • This layer may consist of an acrylate Vinyl acetate adhesive, which is preferably uncrosslinked, such as DuroTak DT 87- 4287.
  • This drug-free layer can improve the adhesive properties of the system. This layer has therefore not been loaded with active substance during production.
  • the stripping layer may be an active-substance-impermeable protective layer, for example a siliconized polyester film, which is peeled off before application to the skin
  • Rivastigmine was diluted in ethyl acetate. To the resulting solution was added an acrylate-hydrocarbon graft copolymer (hybrid adhesive), followed by
  • Solvent by the film was spread with coated homogenizer for 15 min at 60 ° C. On the dried adhesive film was a siliconized
  • a thin film of a surface weight of 10 to a maximum of 40 g / m 2 is applied to the skin side, which is a polymer from the group of polyacrylates, silicones, block copolymers, polyisobutylenes, acrylate Rubber hybrids or a pressure-sensitive mixture comprises or consists of a plurality of these polymers.
  • the acrylate-hydrocarbon graft copolymer (hybrid adhesive) was an acrylate polymer having functional hydroxyl groups as a graft base with grafted ethylene-butylene macromer terminated with methacrylate groups
  • Example 3 Weight average Mw of macromolecular weight about 4000, wherein the graft copolymer in Example 3 was crosslinked. Incidentally, reference can be made to Example 1.
  • Example 2 an acrylate-hydrocarbon graft copolymer (hybrid adhesive) according to US 2010/0 068 515 AI Example 2 Sample B (weight average Mw of macromolecular weight about 4000) was used. Incidentally, reference can be made to Example 1.
  • Rivastigmine was dissolved in ethyl acetate.
  • a polymer mixture namely non-crosslinked acidic acrylate adhesive (eg DuroTak DT 87-235A) with a butyl methacrylate / methyl methacrylate copolymer (eg Plastoid B), was added and homogenized. Thereafter, the obtained mixture was spread on a polyester film to a weight of 60 g / m 2 . The solvent was removed by drying the laminate at 60 ° C for 15 minutes.
  • Adhesive layer

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Botany (AREA)
  • Emergency Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne un système thérapeutique transdermique doté d'un inhibiteur de la cholinestérase pour le traitement de démence de gravité faible à moyenne du type maladie d'Alzheimer.
PCT/EP2011/003473 2010-07-12 2011-07-12 Système thérapeutique transdermique doté d'un inhibiteur de la cholinestérase WO2012007150A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102010026903A DE102010026903A1 (de) 2010-07-12 2010-07-12 Transdermales therapeutisches System mit Avocadoöl oder Palmöl als Hilfsstoff
DE102010026903.4 2010-07-12

Publications (1)

Publication Number Publication Date
WO2012007150A1 true WO2012007150A1 (fr) 2012-01-19

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DE (1) DE102010026903A1 (fr)
WO (1) WO2012007150A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2614820A1 (fr) * 2012-01-11 2013-07-17 AMW GmbH Système thérapeutique transdermique doté d'un inhibiteur de la cholinestérase
EP2859892A4 (fr) * 2012-06-12 2015-11-18 Km Transderm Ltd Timbre
WO2017021448A1 (fr) 2015-08-04 2017-02-09 Repsol, S.A. Nouvelles formulations d'adhésifs sensibles à la pression

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105263488A (zh) * 2013-03-15 2016-01-20 纳尔制药有限公司 含卡巴拉汀的经皮给药系统

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EP0836506B1 (fr) 1995-06-07 2002-12-18 Ortho-McNeil Pharmaceutical, Inc. Timbre transdermique pour l'administration de 17-deacetyl norgestimate, seul ou en combinaison avec un estrogene
DE69830095T2 (de) 1997-04-11 2006-01-19 L'oreal Pharmazeutisches, kosmetisches oder dermo-pharmazeutisches Pflaster zur Ab- gabe mehrerer verschiedenartiger Wirkstoffe.
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WO2011034323A2 (fr) * 2009-09-16 2011-03-24 Samyang Corporation Système de distribution transdermique, son procédé de fabrication, et procédé de distribution transdermique utilisant le système
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Publication number Priority date Publication date Assignee Title
EP2614820A1 (fr) * 2012-01-11 2013-07-17 AMW GmbH Système thérapeutique transdermique doté d'un inhibiteur de la cholinestérase
EP2859892A4 (fr) * 2012-06-12 2015-11-18 Km Transderm Ltd Timbre
US10758494B2 (en) 2012-06-12 2020-09-01 KM Transderm Ltd. Rivastigmine-containing adhesive patch
WO2017021448A1 (fr) 2015-08-04 2017-02-09 Repsol, S.A. Nouvelles formulations d'adhésifs sensibles à la pression

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