WO2011137894A1 - Comprimé soluble comprenant un triptane ou un neuroleptique atypique - Google Patents

Comprimé soluble comprenant un triptane ou un neuroleptique atypique Download PDF

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Publication number
WO2011137894A1
WO2011137894A1 PCT/DE2011/001022 DE2011001022W WO2011137894A1 WO 2011137894 A1 WO2011137894 A1 WO 2011137894A1 DE 2011001022 W DE2011001022 W DE 2011001022W WO 2011137894 A1 WO2011137894 A1 WO 2011137894A1
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WO
WIPO (PCT)
Prior art keywords
tablet
orodispersible
orodispersible tablet
tablets
tablet according
Prior art date
Application number
PCT/DE2011/001022
Other languages
German (de)
English (en)
Inventor
Staša Vuković
Biljana Stupar
Tijana Mihajlović
Original Assignee
Stada Arzneimittel 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 Stada Arzneimittel Ag filed Critical Stada Arzneimittel Ag
Priority to EP11738393A priority Critical patent/EP2566452A1/fr
Publication of WO2011137894A1 publication Critical patent/WO2011137894A1/fr

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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
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • 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
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4196—1,2,4-Triazoles
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines containing further heterocyclic rings

Definitions

  • Orodispersible tablet comprising a triptan or an atypical
  • the present invention relates to an orodispersible tablet comprising a triotan or an antiviral neuroleic acid as a pharmaceutical active ingredient.
  • Orodispersible tablets are tablets that dissolve relatively quickly in the mouth. They have the advantage that they are also used by persons with dysphagia as well as lying down
  • orodispersible tablets have the advantage that for their ingestion a Wegrinken of water is usually not required, so that orodispersible tablets for the
  • Lacquer tablets are called - are tablets for
  • Film-coated tablets consist of a tablet core coated with a very thin layer of polymer.
  • the polymer layer can improve the
  • Triptans and atonic neuroleptics are known in the art. They are used in particular for the treatment of migraine or for the treatment of psychotic symptoms, especially in schizophrenics.
  • Triptans and atypical neuroleptics are offered both in the form of film and coated tablets.
  • Antipsychotics olanzapine and aripiprazole are considered under the brand name Zyprexa ® and Abilify ®
  • melt and film tablets of an active ingredient are formulated differently from each other, wherein the film, in contrast to the tablets are still coated with a Poiymerfilm.
  • the separate production of enamel and film-coated tablets is complicated and cost-intensive.
  • triptan or an atypical neuroleptic drug as a pharmaceutical agent which can be administered both as orodine tablet as well as a conventional tablet for swallowing.
  • Orodispersible tablet according to the invention can be administered both as a fused tablet and as a conventional swallow tablet.
  • the relatively high mechanical strength of the orodispersible tablet according to the invention causes a
  • Melted tablets and corresponding film tablets can be configured.
  • the orodispersible tablet according to the invention has the advantage that, as evidenced by its relatively high breaking strength F, it is relatively stable mechanically and therefore less, as is usual with orodispersible tablets, too
  • melt tablet according to the invention can therefore be offered, for example, in blister packs by blistering and does not have to be packaged in unpractical blisters with a peel film, as is otherwise customary, which increases patient acceptance.
  • the tablet according to the invention is an orodispersible tablet.
  • the European Pharmacopoeia ⁇ Ph.Eur defines orodispersible tablets as uncoated tablets that are kept in the mouth where they quickly disperse before being swallowed, with orodispersible tablets having a disintegration time according to Ph. Eur. 2.9.1 of less than or equal to 3 minutes.
  • the orodispersible tablet according to the invention satisfies this definition, although alternatively it can also be swallowed before it spreads in the mouth.
  • orodispersible tablet is understood to mean an uncoated tablet which is retained in the mouth, where it is rapidly distributed, before it is swallowed, or swallowed before it has spread in the mouth, being a
  • a triptane in the tablet according to the invention, can be contained as an active ingredient.
  • Triptans are known in the art (see Mutschier et al.
  • Triptans are 5-HT 1B / 1D receptor agonists and are preferably used for the acute treatment of migraine and cluster headache. Their mechanism of action is based on selective stimulation of Serotoni (5-hydroxytryptamine (5-HT)) receptors of subtype 5
  • an atypical neuroleptic may be included as an active ingredient in the orodispersible tablet according to the invention.
  • Diphenylbutylpiperidinen either barely or at least
  • the triptane or atypical antipsychotic may be in the form of the free base or in the form of a pharmaceutically acceptable Salt in the fusible tablet according to the invention
  • the orodispersible tablet according to the invention has a
  • Breaking strength F of greater than or equal to 25 N on.
  • Breaking strength F is according to Ph.Eur. 2.9.8 to determine. It is inventively preferred that the breaking strength F is measured by means of a tablet hardness tester by uniaxial vertical load between two horizontal jaws with plane-parallel surfaces by recording a controlled force-displacement curve, wherein placed in the measurement, the sample on the lower jaw and whereupon the upper jaw is progressively lowered. According to the invention, it is particularly preferred that the breaking strength F is determined by means of a tablet hardness tester from ERWEKA International AG, Switzerland,
  • TBH 250 IC is determined.
  • Round tablets i. Tablets having a circular cross-section such as e.g. round flat biplane tablets, are used at the
  • Orodispersible tablet a fracture strength F according to Ph.Eur. 2.9.8 greater than or equal to 25N. In this context it is
  • Breaking strength F measured forces are in a range of 20 N to 60 N, more preferably in a range of 25 N to 55 N. According to a preferred embodiment of
  • the orodispersible tablet has a breaking strength F of greater than or equal to 25 N to 55 N, preferably a breaking strength F of 27 N to 45 N and particularly preferably a breaking strength F of 30 N to 40 N.
  • the breaking strength F of invention For example, Schrne1 z abletfce can be sorted by type and. Amount of binder used and the size of the
  • applied pressing force can be adjusted in the tableting.
  • the breaking strength F of a tablet may depend on its shape and dimensions. It may therefore be preferred according to the invention, the mechanical strength of
  • the compressive strength ⁇ is calculated by means of the experimentally determined fracture strength F.
  • F fracture strength
  • D is the tablet diameter
  • the compressive strength ⁇ is calculated by means of the following mathematical relationship (see “The tablet”, A. Ritschel et al., 2nd edition, Editio-Cantor-Verlag, 2002, ISBN 3-87193 -228-0): IOF
  • D is the tablet diameter
  • the orodispersible tablet it is preferable for the orodispersible tablet to have a compressive strength ⁇ of greater than or equal to 0.55 N / mm 2 , preferably a compressive strength ⁇ in a range of 0.55 ii A * - in a range of 0.60 N / mm 2 to 1.50 N / mm 2 and more preferably a compressive strength ⁇ in a range of 0.70 N / mm 2 to 1.30 N / mm 2 .
  • the orodispersible tablet is cylindrical.
  • the orodispersible tablet has a disintegration time of less than or equal to 60 s, preferably a disintegration time of 10 s to 30 s and more preferably a disintegration time of 10 s to 20 s.
  • the decay time is according to Ph.Eur. 2.9.1, preferably using water as the medium.
  • the orodispersible tablet has a friability of less than or equal to 1%. and most preferably a friability of 0.1% to 0.4%.
  • the friability is according to Ph.Eur. 2.9.7 to determine.
  • triptane is selected from the group consisting of
  • the triptane is selected from the group consisting of
  • the atypical neuroleptic is selected from the group
  • the atypical neuroleptic is selected from the group
  • the atypical antipsychotic drug is aripiprazole.
  • a tablet is prepared by mixing a granulate with pharmaceutical excipients and the resulting mixture is compressed into a tablet, so in this formulation type between an inner phase (granules) and multipli uuc cn rriicitn-; (nii L ü l L unc, _i_.ii nc ⁇ ucii
  • Granules embedded is differentiated. According to a further preferred embodiment of the invention
  • the orodispersible tablet comprises an inner phase and an outer phase, wherein the inner phase contains the active ingredient.
  • the inner phase comprises a water-soluble and a water-insoluble pharmaceutical filler.
  • Fillers serve the purpose of increasing the volume of tablets to a suitable size, especially for low-dose tablets.
  • the amount of filler depends on its nature, the size of the tablet and the amount of the active ingredient.
  • Water-soluble is understood as meaning a solubility in water at a temperature of 15 ° C. to 25 ° C. of more than 33 mg per ml, preferably one
  • the water-soluble filler is selected from the group consisting of a sugar and a sugar alcohol.
  • the sugar or the sugar alcohol is selected from the group consisting of dextrose, lactose, mannitol, sorbitol,
  • the water-soluble filler is mannitol. According to a further preferred embodiment of the
  • the water-insoluble filler is selected from the group consisting of aluminum hydroxide, barium sulfate,
  • the water-insoluble filler is microcrystalline cellulose.
  • the weight ratio of water-soluble to water-insoluble filler in the inner phase is in a range of 1 to 10, preferably in a range of 6 to 10 and more preferably in a range of 8 to 10.
  • the inner phase is a wet granules, ie a dried granules which has been produced by means of a wet granulation process.
  • the moist granules are a binder granules.
  • the binder granules contain a hydrophilic polymer as a binder.
  • the hydrophilic polymer is selected from the group consisting of hydroxypropylmethylcellulose (HPMC), carboxymethylcellulose and salts thereof, methylcellulose, hydroxyethylcellulose,
  • Polyvinyl alcohol polymers of acrylic acid and its salts, vinylpyrrolidone-vinyl acetate Copoly er, gelatin, guar gum, partially hydrolyzed starch, especially maltodextrin, alginates and xanthan gum.
  • the hydrophilic polymer is maltodextrin.
  • the proportion of the internal phase in the binder is from 1% by weight to 20% by weight, based on the total weight of the internal
  • Phase preferably 3 wt .-% to 10 wt .-%.
  • orodispersible tablet it is provided that the proportion of the ore tablet to internal phase 20 wt .-% to 80 Orodispersible tablet, preferably 30% to 70% by weight and
  • the remaining weight fraction is outer phase.
  • the outer phase comprises a water-soluble filler and binder suitable for direct tabletting, as well as a
  • the water-soluble filler and binder is selected from the group consisting of lactose and mannitol.
  • the mannitol is in the form of a mannitol granule.
  • the orodispersible tablet comprises one or more pharmaceutical excipients selected from the group consisting of a
  • Disintegrants lubricants, flow control agents and a taste masking agent. According to a further preferred embodiment of the
  • orodispersible tablet it is provided that the pharmaceutical excipient is contained in the outer phase.
  • the taste-masking agent comprises a sweetener and / or a flavoring agent.
  • the sweetener is selected from the group consisting of saccharin, saccharin sodium, saccharin calcium and saccharin potassium.
  • the sweeteners mentioned have no adverse effect on the stability of the active pharmaceutical ingredient.
  • the sweetener is free of aspartame. Aspartame may have an adverse effect on the stability of the active pharmaceutical ingredient.
  • a typical orodispersible tablet provided by the present invention is a typical orodispersible tablet provided by the present invention.
  • - includes zolmitriptan, rizatriptan or aripiprazole as a pharmaceutical active substance
  • the proportion of internal phase is 40% by weight to 60%
  • the outer phase comprises a water-soluble
  • Direct tableting suitable filling and binding agent as well as a water-insoluble filling and binding agent suitable for direct tabletting;
  • Binder in a range of 2 to 0.5;
  • the present invention further relates to a method for
  • Production of a tablet according to the invention comprising the steps: or an atypical neuroleptic as a pharmaceutical agent;
  • the breaking strength of the compact, i. the orodispersible tablet according to the invention can, for example, the nature and amount of the binder used and the size of the
  • applied pressing force can be adjusted in the tableting.
  • the granules provided are a binder granules, wherein the used for the preparation of the granules
  • Granulating liquid maltodextrin as a binder in a proportion of 35% (w / v) to 45% (w / v) comprises. It is further preferred that the granulating liquid is an aqueous granulating liquid.
  • Orodispersible tablets containing 7.26 mg of rizatriptan benzoate (equivalent to 5.0 mg of rizatriptan) were prepared.
  • a granulate fraction 2 mm was separated by means of a sieve of 2 mm mesh size.
  • the separated granule fraction was dried in a fluid bed dryer and the resulting dried granules further selected by means of a sieve of 1 mm mesh size to give a final
  • the final active ingredient granules were mixed with the outer phase substances, i. Mannitol (pre-granulated), microcrystalline cellulose, crospovidone, fumed silica,
  • Tablet press to round flat biplane tablets with a diameter of 8.0 mm and a ridge height ( thickness) of 2.3 mm (+ 0.2 mm) pressed.
  • the tablets thus obtained had the following properties:
  • Breaking strength F (Ph. Eur. 2.9.8): Mean: 36 N
  • Decay time (Ph.Eur 2.9.1): mean: 25 s
  • the breaking strength P of the tablets according to Ph.Eur. 2.9.8 was determined by means of a tablet hardness tester from ERWEKA
  • Embodiment 2 is a diagrammatic representation of Embodiment 1:
  • Crospovidone 16 0 disintegrant fumed 2.0 flow control silica medium
  • the tablets thus obtained had the following properties:
  • Orodispersible tablets containing 2.5 mg zolmitriptan were prepared.
  • the orodispersible tablets had the composition given in the table:
  • Binders of microcrystalline rUJLX-UHU Binders of microcrystalline rUJLX-UHU.
  • the tablets thus obtained had the following properties: ⁇ -. , ⁇ "" * - - ⁇ - ⁇ 4- mn ⁇ ,, - * ⁇ ⁇ ⁇ ⁇
  • the breaking strength F of the tablets according to Ph.Eur. 2.9.8 was determined by means of a tablet hardness tester from ERWE A
  • the tablets thus obtained had the following properties:
  • Decay time (Ph.Eur 2.9.1): mean: 15 s
  • the breaking strength F of the tablets according to Ph.Eur. 2.9.8 was determined by means of a tablet hardness tester from ER EKA
  • Orodispersible tablets containing 5.0 mg of aripiprazole were prepared.
  • the orodispersible tablets had the composition given in the table:
  • the breaking strength F of the tablets according to Ph.Eur. 2.9.8 was determined by means of a tablet hardness tester from ERWE A
  • Embodiment 6 Melt tablets containing 10.0 mg of aripiprazole were prepared.
  • the orodispersible tablets had the in Table 6
  • the tablets thus obtained had the following properties:
  • Breaking strength F (Ph. Eur. 2.9.8): mean: 30 N
  • Friability (Ph.Eur 2.9.7): 0, 14%
  • the breaking strength F of the tablets according to Ph.Eur. 2.9.8 was determined by means of a tablet hardness tester from ERWEKA
  • Orodispersible tablets containing 15.0 mg of aripiprazole were prepared.
  • the orodispersible tablets had the composition given in the table:
  • the tablets thus obtained had the following properties:
  • the breaking strength F of the tablets according to Ph.Eur. 2.9.8 was determined by means of a tablet hardness tester from ERWEKA
  • Embodiment 8 Melt tablets containing 30.0 mg of aripiprazole were prepared.
  • the orodispersible tablets had the composition given in Table 8: TABLE 8
  • the breaking strength F of the tablets according to Ph.Eur. 2.9.8 was determined using a Tabietten hardness tester from ER EKA

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
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Abstract

La présente invention concerne un comprimé soluble comprenant un triptane ou un neuroleptique atypique en tant que principe actif pharmaceutique. Pour obtenir un comprimé qui peut être employé aussi bien comme comprimé soluble que comme comprimé à avaler, l'invention a pour objet un comprimé soluble comprenant un triptane ou un neuroleptique atypique comme principe actif pharmaceutique, le comprimé soluble ayant une résistance à la rupture supérieure ou égale à 25 N.
PCT/DE2011/001022 2010-05-04 2011-05-03 Comprimé soluble comprenant un triptane ou un neuroleptique atypique WO2011137894A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP11738393A EP2566452A1 (fr) 2010-05-04 2011-05-03 Comprimé soluble comprenant un triptane ou un neuroleptique atypique

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102010019416.6 2010-05-04
DE102010019416A DE102010019416A1 (de) 2010-05-04 2010-05-04 Schmelztablette, umfassend ein Triptan oder ein atypisches Neuroleptikum

Publications (1)

Publication Number Publication Date
WO2011137894A1 true WO2011137894A1 (fr) 2011-11-10

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EP (1) EP2566452A1 (fr)
DE (1) DE102010019416A1 (fr)
WO (1) WO2011137894A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013100878A1 (fr) * 2011-12-27 2013-07-04 Mahmut Bilgic Formulations pharmaceutiques comprenant de l'aripiprazole
WO2014104989A1 (fr) * 2011-12-27 2014-07-03 Mahmut Bilgic Compositions pharmaceutiques comprenant de l'aripiprazole

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1145711A1 (fr) * 2000-04-12 2001-10-17 Bristol-Myers Squibb Company Forme de dosage orale très fondante
WO2004100857A2 (fr) * 2003-05-07 2004-11-25 Akina, Inc. Granules a teneur elevee en plastique, destines a la fabrication de comprimes a dissolution rapide
US20060078614A1 (en) * 2004-10-12 2006-04-13 Venkatesh Gopi M Taste-masked pharmaceutical compositions
US20060105038A1 (en) * 2004-11-12 2006-05-18 Eurand Pharmaceuticals Limited Taste-masked pharmaceutical compositions prepared by coacervation
EP2082735A1 (fr) * 2008-01-23 2009-07-29 Helm AG Aripiprazole amorphe et son procédé de préparation

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1145711A1 (fr) * 2000-04-12 2001-10-17 Bristol-Myers Squibb Company Forme de dosage orale très fondante
WO2004100857A2 (fr) * 2003-05-07 2004-11-25 Akina, Inc. Granules a teneur elevee en plastique, destines a la fabrication de comprimes a dissolution rapide
US20060078614A1 (en) * 2004-10-12 2006-04-13 Venkatesh Gopi M Taste-masked pharmaceutical compositions
US20060105038A1 (en) * 2004-11-12 2006-05-18 Eurand Pharmaceuticals Limited Taste-masked pharmaceutical compositions prepared by coacervation
EP2082735A1 (fr) * 2008-01-23 2009-07-29 Helm AG Aripiprazole amorphe et son procédé de préparation

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
A. RITSCHEL ET AL.: "Die Tablette", 2002, EDITIO-CANTOR-VERLAG
BURSTEIN R ET AL: "Anti-migraine action of triptans is preceded by transient aggravation of headache caused by activation of meningeal nociceptors", PAIN, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 115, no. 1-2, 1 May 2005 (2005-05-01), pages 21 - 28, XP004844680, ISSN: 0304-3959, DOI: 10.1016/J.PAIN.2005.01.027 *
MUTSCHLER ET AL.: "Arzneimittelwirkungen, Lehrbuch der Pharmakologie und Toxikologie", 2008
POTHMANN R: "Migräne bei Jugendlichen (Migraine in adolescents)", PAEDIATRISCHE PRAXIS: ZEITSCHRIFT FUER KINDER- UND JUGENDMEDIZIN, HANS MARSEILLE VERTRIEB MEDIZINISCHER ZEITSCHRIFTEN, MUNICH, DE, vol. 74, no. 2, 1 December 2009 (2009-12-01), pages 221 - 236, XP008142706, ISSN: 0030-9346 *

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EP2566452A1 (fr) 2013-03-13

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