EP2672959A1 - Composition de granulés comportant du tadalafil et un délitant - Google Patents
Composition de granulés comportant du tadalafil et un délitantInfo
- Publication number
- EP2672959A1 EP2672959A1 EP11703449.6A EP11703449A EP2672959A1 EP 2672959 A1 EP2672959 A1 EP 2672959A1 EP 11703449 A EP11703449 A EP 11703449A EP 2672959 A1 EP2672959 A1 EP 2672959A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- tadalafil
- granulate
- dosage form
- superdisintegrant
- croscarmellose sodium
- 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- Withdrawn
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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
Definitions
- the present invention relates to a co-granulate comprising tadalafil and a
- superdisintegrant advantageously croscarmellose sodium
- CIALIS® is a known pharmaceutically active compound, which is marketed, e.g., under brand name CIALIS®, for the treatment of erectile dysfunction and pulmonary arterial hypertension.
- the marketed product is a film-coated tablet for oral administration comprising 2.5, 5, 10 or 20 mg of the active substance.
- Inactive ingredients in CIALIS® are lactose monohydrate, croscarmellose sodium, hydroxypropylcellulose, microcrystalline cellulose, sodium laurylsulfate and magnesium stearate.
- Tadalafil and its pharmaceutical compositions have been disclosed, e.g., in WO 95/19978 and WO 00/66099.
- tadalafil is in a certain aspect a follow-up product to the well known compound sildenafil (Viagra). Its main advantage is longer duration of action and minimized potential for side effects such as vision abnormalities.
- tadalafil One possibility of improving the dissolution rate of tadalafil from solid pharmaceutical compositions is to use the active ingredient with low average particle size.
- the patent applications WO 01/08688 and WO 01/08686 disclose a population of tadalafil particles characterized by an average particle size (expressed as d(0.9)) less than 40 ⁇ . Such particulated form of tadalafil may exhibit better dissolution from pharmaceutical
- tadalafil is thereby finely dispersed in the carrier, which may result in improved dissolution due to enhanced surface area of the drug substance.
- solid dispersions comprising tadalafil have been disclosed, e.g., in WO 96/38131.
- Molecular dispersions of tadalafil in a polymeric carrier have been disclosed, e.g., in WO 2009/000493.
- a pharmaceutical composition comprising a combination of tadalafil and starch has been disclosed in WO 2008/134557.
- An adsorbate of tadalafil on the surface of silica has been disclosed in EP 2238979.
- compositions have been disclosed, e.g., in WO 00/20033, WO 01/41807, WO 2007/002125 or WO 2008/005039.
- the present invention relates to pharmaceutical compositions comprising a granulated product comprising tadalafil and a superdisintegrant, preferably croscarmellose sodium.
- the present invention provides a co-granulate, preferably a free-flowing co-granulate, comprising tadalafil, a superdisintegrant, and, preferably, at least one binder and/or filler.
- a preferred superdisintegrant is croscarmellose sodium.
- the weight ratio between croscarmellose sodium and tadalafil is equal to or higher than 5 : 1.
- the present invention provides a process comprising a step of aqueous granulation of tadalafil with a superdisintegrant, e.g. croscarmellose sodium, preferably in the presence of a binder, followed by drying the resulting granulate.
- a superdisintegrant e.g. croscarmellose sodium
- the tadalafil starting material for making the co-granulate comprises a population of tadalafil particles characterized by a particle size d(0.9) > 40 ⁇ .
- the present invention provides a pharmaceutical composition comprising the co-granulate as defined above and at least one pharmaceutically acceptable excipient.
- the present invention provides a process for making a tadalafil- comprising pharmaceutical composition, comprising a step of providing a co-granulate comprising tadalafil and a superdisintegrant, preferably croscarmellose sodium, followed by a step of dry mixing the above co-granulate with at least one pharmaceutically acceptable excipient.
- the present invention provides a pharmaceutical oral dosage form comprising tadalafil, preferably a compressed dosage form, comprising a dose of the pharmaceutical composition as defined above.
- the dosage form exhibits a dissolution rate of at least about 70 wt% within about 15 min when tested by the Ph. Eur. paddle method in 1000 ml of an aqueous medium containing 0.35% of SLS with the paddle rotating at a speed of 50 rpm.
- the present invention provides a process for making a pharmaceutical oral dosage form comprising tadalafil, comprising the steps of:
- composition and/or dosage form preferably comprises from 2 to 10% of tadalafil (w/w).
- the dosage form preferably comprises from 1 to 50 mg of tadalafil.
- the invention relates to the use of the co-granulate of tadalafil with croscarmellose sodium, preferably in free-flowing particulate form, in medicine, in particular in the treatment of erectile dysfunction and pulmonary arterial hypertension.
- the present invention relates to the enhancement of the inherently poor dissolution of tadalafil from solid pharmaceutical compositions by formulating tadalafil into a co-granulate with a superdisintegrant, preferably with croscarmellose sodium, and, optionally, a binder.
- the "superdisintegrant" in our application is a conventionally used term in the pharmaceutical industry and refers to a compound, which exhibits a rapid and a high degree of swelling when in contact with saliva or intestinal fluid.
- Typical examples which are also subject of our invention, are modified celluloses, e.g. croscarmellose sodium or low substituted hydroxypropyl cellulose, cross-linked polymers, e.g. crospovidone, or modified starches, e.g. sodium starch glycolate.
- Croscarmellose sodium is the sodium salt of a cross-linked, partly O- (carboxymethylated) cellulose. It is a well known and well defined excipient in the pharmaceutical industry, typically useful as a disintegrant. It is commercially available under various brand names. For more details about this excipient, see ,e.g., Arthur H. Kibbe (Ed.), Handbook of Pharmaceutical Excipients, Third Edition 2000, p. 160-162).
- the present invention typically provides a co-granulate of tadalafil with croscarmellose sodium.
- the weight ratio between croscarmellose sodium and tadalafil in the co- granulate is equal to or higher than 5 : 1.
- This co-granulate preferably in amounts, which assure the final concentration of tadalafil therein of between 2 to 10% (w/w), may be formulated in solid pharmaceutical compositions, e.g. by a dry mixing with extragranular excipients.
- This inventive solution is based on the finding that dissolution of the inherently poorly soluble tadalafil may be sufficiently increased by this co-granulation, when comparing it with a composition, wherein croscarmellose sodium has been formulated into a tadalafil- comprising solid pharmaceutical composition in conventional concentrations (0.5-5%) and without pre-granulation with tadalafil. Furthermore, it was found that it is not necessary to provide a population of tadalafil particles of an average particles size (when expressed by the d(0.9) value) of less than 40 ⁇ .
- the dissolution rate can be, in general, enhanced by increasing the surface area of the drug by micronization
- the micronized particles have a tendency to agglomerate and this effect can result in a decreased effective surface for dissolution.
- the inventor speculates that the granulation causes deposition of the drug upon the surface of the hydrophilic and strongly swelling superdisintegrant. Once digested, the superdisintegrant discomposes the medicament delivering a fine suspension of drug particles, which prevents agglomeration and improves the dissolution.
- tadalafil substance having an average particle size d(0.9) higher than 40 ⁇ , e.g. tadalafil directly produced by a chemical synthesis.
- d(0.9)value in association with a number means that the size of 90% of the particles of the population are less than or equal to the size expressed by that number when measured by a light scattering method.
- the co-granulate of the invention may also comprise at least one binder, for instance microcrystalline cellulose, methyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, polyvinylpyrrolidone, copovidone, sodium alginate etc.
- the binder may improve physical properties of the co-granulate, particularly it may assure that the co-granulate is obtained as a free-flowing particulate material with good handling properties.
- the co-granulate may optionally comprise one or more inert fillers/diluents, e.g., lactose, lactose monohydrate, mannitol, sorbitol, microcrystalline cellulose, dextrates, dextrins, dextrose, fructose, lactitol, maltitol, maltodextrins, maltose, calcium phosphates, xylitol, which assure a proper final concentration of tadalafil in the final composition.
- inert fillers/diluents e.g., lactose, lactose monohydrate, mannitol, sorbitol, microcrystalline cellulose, dextrates, dextrins, dextrose, fructose, lactitol, maltitol, maltodextrins, maltose, calcium phosphates, xylitol, which assure a proper final concentration of
- the co-granulate of the invention does not comprise starch.
- the co-granulate of the present invention is advantageously prepared by a wet granulation process.
- water may be advantageously used as the granulation liquid in the process of the invention despite the prejudice that superdisintegrants are sensitive to water.
- water does not substantially affect the disintegration ability, rather it aids in assuring a uniform content of tadalafil within the granulate.
- organic solvents e.g. ethanol
- granulation liquids e.g.
- a useful process of making the co-granulate comprises the following steps:
- the mixing and granulating is typically performed with the same equipment, at a speed of about 100 to 200 rpm.
- Croscarmellose sodium and tadalafil are preferably mixed in the weight ratio equal to or higher than 5 : 1.
- the relative weight amount of the binder is typically between 1/5 to 1/10 of the weight of tadalafil.
- the relative weight amount of water is typically 10 to 50 weight % in respect to the solid material.
- the drying step is performed in fluid bed equipment, at a temperature of about 40°C to about 60°C, typically at about 50°C.
- the dry co-granulate may be milled and/or sieved on a suitable
- the co-granulate of the present invention and/or the co-granulate made by the above process may be formulated into solid pharmaceutical compositions, preferably into tablet compositions, by combining it with at least one extragranular pharmaceutically acceptable excipient.
- a typical process of such formulation comprises a step of providing the above co- granulate followed by a step of dry mixing it with at least one pharmaceutically acceptable excipient. As rapid dissolution of tadalafil from the composition is therapeutically
- composition typically does not comprise any excipient serving as a release- controlling agent.
- excipients typically comprise:
- a] at least one water soluble or water insoluble filler/binder are, without any limitation, lactose, lactose monohydrate, mannitol, sorbitol, microcrystalline cellulose, methyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, dextrates, dextrins, dextrose, fructose, lactitol, maltitol, maltodextrins, maltose, calcium phosphates, xylitol, starch, modified starch, polyvinylpyrrolidone, copovidone, sodium alginate, etc.
- the examples are, without any limitation, starches, cross-linked celluloses, or cross-linked polymers such as starch, modified starch,
- croscarmellose sodium crospovidone
- sodium starch glycolate carboxymethylcellulose calcium, carboxymethylcellulose sodium, colloidal silicon dioxide, guar gum, magnesium aluminium silicate, methylcellulose, polacrilin potassium, sodium alginate, etc.
- c at least one lubricant.
- the examples are, without any limitation, talc, magnesium stearate, calcium stearate, stearic acid, hydrogenated vegetable oils, palmitic acid, carnauba wax, mineral oil, sodium stearyl fumarate, polyethylene glycol, etc.
- the relative amount of tadalafil in the solid pharmaceutical composition is typically from about 2 to about 10 weight %. Accordingly, the relative amount of croscarmellose sodium in the composition is typically from about 10 to 50%, based on the total weight of the composition.
- composition of the present invention is advantageously formulated into a dosage form; such dosage form comprises a desired dose of the
- the dosage form is a compressed dosage form, which is typically a tablet.
- the compressed dosage form is formulated by a process of direct compression. This process comprises adjusting the composition to portions - dose units - comprising a therapeutic amount of the active substance and compressing the doses of the composition to tablets on a suitable tablet press.
- the tablets should have a suitable hardness in order to obtain tablets with a friability below 0.5% preferably below 0.1%.
- the typical hardness of the tablets is 75N.
- the dosage form typically comprises from 1 to 50 mg of tadalafil, preferably 2.5, 5, 10 or 20 mg of tadalafil.
- the compressed dosage form preferably exhibits a dissolution rate which is characterized by a dissolution of more than 70 wt% of tadalafil in 15 min when a sample of the composition is tested by a Ph. Eur. paddle method in 1000 ml of an aqueous medium containing 0.35% of sodium laurylsulfate with the paddle rotating at a speed of 50 rpm.
- the tablets may be optionally further coated by a film-coat.
- the coating serves generally for cosmetic purposes.
- the coating material typically has no influence on the release rate, except of an inherent short initial delay in dissolution due to the time necessary to dissolve the coat.
- the coating may be selected from amongst one or more of those suitable coating materials known in the art. Coating may be performed by applying one or more film forming polymers, with or without other pharmaceutically inert excipients, as a solution/suspension. Coating is done using any conventional coating technique known in the art, such as spray coating in a conventional coating pan or fluidized bed processor; or dip coating.
- the co-granulate of tadalafil with a superdisintegrant which advantageously is croscarmellose sodium, typically in a weight ratio of croscarmellose sodium and tadalafil equal to or higher than 5 : 1, as well as pharmaceutical compositions and dosage forms comprising it are useful in medicine, specifically for the treatment of diseases and conditions known to be treated with tadalafil.
- these conditions include erectile dysfunction and pulmonary arterial hypertension, but are not limited thereto.
- the present invention provides a method of treatment, particularly that of erectile dysfunction or pulmonary arterial hypertension, comprising orally administering to a patient in need thereof a solid pharmaceutical composition comprising a therapeutical amount of tadalafil within a co-granulate with a superdisintegrant, advantageously croscarmellose sodium, typically in a weight ratio of croscarmellose sodium and tadalafil equal to or higher than 5 : 1.
- Example 1 Pharmaceutical tablet comprising tadalafil and croscarmellose sodium granulate
- hydroxypropylcellulose and aerosil was made in a high shear mixer for 5 min. After that, a 20% of water w/w of powder was poured onto the powder and mixed at 150 rpm to obtain a granulate. The granulate was dried in a fluid bed equipment until a loss on drying below 2% was obtained.
- the resulting granulate was sieved manually through a 1 mm sieve and mixed with microcrystalline cellulose and crospovidone for 15 min. Finally, Mg stearate was added to the blend and mixed for 5 min.
- the lubricated blend was compressed in an excentric press machine at a compression force of approx. 13 kN.
- the resulting tablets showed a hardness of 74 N, a disintegration time ⁇ 2 min and a friability of 0.2%.
Landscapes
- Health & Medical Sciences (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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/EP2011/051963 WO2012107090A1 (fr) | 2011-02-10 | 2011-02-10 | Composition de granulés comportant du tadalafil et un délitant |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2672959A1 true EP2672959A1 (fr) | 2013-12-18 |
Family
ID=44474983
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP11703449.6A Withdrawn EP2672959A1 (fr) | 2011-02-10 | 2011-02-10 | Composition de granulés comportant du tadalafil et un délitant |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP2672959A1 (fr) |
WO (1) | WO2012107090A1 (fr) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015000853A1 (fr) * | 2013-07-05 | 2015-01-08 | Synthon B.V. | Composition pharmaceutique comprenant une dispersion solide de tadalafil |
KR101663238B1 (ko) * | 2013-11-15 | 2016-10-14 | 한미약품 주식회사 | 타다라필 및 암로디핀을 포함하는 복합 고형 제제 |
CN109157520B (zh) * | 2018-09-07 | 2021-04-02 | 苏州科技城医院 | 他达拉非片剂及其制备方法 |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9401090D0 (en) | 1994-01-21 | 1994-03-16 | Glaxo Lab Sa | Chemical compounds |
GB9511220D0 (en) | 1995-06-02 | 1995-07-26 | Glaxo Group Ltd | Solid dispersions |
US6548490B1 (en) | 1997-10-28 | 2003-04-15 | Vivus, Inc. | Transmucosal administration of phosphodiesterase inhibitors for the treatment of erectile dysfunction |
WO2000020033A1 (fr) | 1998-10-05 | 2000-04-13 | Eisai Co., Ltd. | Comprimes se delitant immediatement dans la cavite buccale |
NO20002097L (no) | 1999-04-30 | 2001-10-26 | Lilly Icos Llc | Fremstillingsgjenstander |
UA71629C2 (en) | 1999-08-03 | 2004-12-15 | Lilli Icos Llc | Composition containing free drug particulate form of ?-carboline (variants), method for its manufacture (variants), and method for treating sexual dysfunction |
US7182958B1 (en) | 1999-08-03 | 2007-02-27 | Lilly Icos Llc. | β-carboline pharmaceutical compositions |
PL1750766T3 (pl) * | 2004-05-11 | 2013-12-31 | Eb Ip Lybrido B V | Preparaty farmaceutyczne i ich zastosowania do leczenia zaburzeń seksualnych u kobiet |
WO2005115345A1 (fr) * | 2004-05-28 | 2005-12-08 | Imaginot Pty Ltd | Systeme d'administration orale de compose therapeutique |
US20090028948A1 (en) | 2004-12-31 | 2009-01-29 | Iceutica Pty Ltd | Nanoparticle composition and methods of synthesis thereof |
EP1898879A1 (fr) | 2005-06-23 | 2008-03-19 | Schering Corporation | Formulations orales à absorption rapide d'inhibiteurs de la pde5 |
CA2622200A1 (fr) | 2005-09-13 | 2007-03-22 | Elan Pharma International, Limited | Formulations nanoparticulaires de tadalafil |
CA2653384C (fr) | 2006-06-30 | 2017-03-14 | Iceutica Pty Ltd | Procedes de preparation de composes biologiquement actifs sous forme de nanoparticules |
KR101140110B1 (ko) | 2006-07-07 | 2012-06-04 | 테바 파마슈티컬 인더스트리즈 리미티드 | 타달라필 및 하나 이상의 담체를 포함하는 고체 조성물 |
ES2405787T3 (es) | 2007-04-25 | 2013-06-03 | Teva Pharmaceutical Industries Ltd. | Formas de dosificación solidas |
DE102007028869A1 (de) | 2007-06-22 | 2008-12-24 | Ratiopharm Gmbh | Verfahren zur Herstellung eines Arzneimittels enthaltend Tadalafil |
US20110028480A1 (en) * | 2008-04-01 | 2011-02-03 | Ocean 1 806, Llc | Orodispersable formulations of phosphodiesterase-5 (pde-5) inhibitors |
EP2238979A1 (fr) | 2009-04-06 | 2010-10-13 | LEK Pharmaceuticals d.d. | Ingrédient pharmaceutique actif absorbé sur un support solide |
-
2011
- 2011-02-10 WO PCT/EP2011/051963 patent/WO2012107090A1/fr active Application Filing
- 2011-02-10 EP EP11703449.6A patent/EP2672959A1/fr not_active Withdrawn
Non-Patent Citations (1)
Title |
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See references of WO2012107090A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO2012107090A1 (fr) | 2012-08-16 |
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