DK2919780T3 - 1,3-Dihydroimidazol-2-thionderivater til anvendelse ved behandlingen af pulmonær arteriel hypertension og lungeskade - Google Patents
1,3-Dihydroimidazol-2-thionderivater til anvendelse ved behandlingen af pulmonær arteriel hypertension og lungeskade Download PDFInfo
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- DK2919780T3 DK2919780T3 DK13803292.5T DK13803292T DK2919780T3 DK 2919780 T3 DK2919780 T3 DK 2919780T3 DK 13803292 T DK13803292 T DK 13803292T DK 2919780 T3 DK2919780 T3 DK 2919780T3
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
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- 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
- A61K31/4164—1,3-Diazoles
- A61K31/417—Imidazole-alkylamines, e.g. histamine, phentolamine
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- 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
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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Claims (19)
1. Forbindelse med formlen I:
i til anvendelse ved behandlingen af pulmonær arteriel hypertension, hvor Ri, R2 og R3 er identisk eller forskellige og betegner hydrogener, halogener, alkyl, alkylaryl, alkyloxy, hydroxy, nitro, amino, alkylcarbonylamino, alkylamino eller dialkylamino-gruppe; R4 betegner hydrogen, alkyl, -alkylaryl eller -alkylheteroaryl; X betegner CH2, oxygenatom eller svovlatom; n er 1,2 eller 3, med den forudsætning, at når n er 1, er X ikke CH2; og de individuelle (R)- og (S)-enantiomerer eller blandinger af enantio-merer og farmaceutisk acceptable salte deraf, eventuelt i kombination med i det mindste én anden aktiv farmaceutisk ingrediens.
2. Forbindelse til anvendelse ifølge krav 1, hvor forbindelsen med formlen I har formlen IA
hvor Ri, R2 og R3 er identiske eller forskellige og betegner hydrogener, halogener, alkyl, alkylaryl, alkyloxy, hydroxy, nitro, amino, alkylcarbonylamino, alkylamino eller dialkylaminogruppe; R4 betegner hydrogen, alkyl eller -alkylarylgruppe; X betegner CH2, oxygenatom eller svovlatom; og n er 1,2 eller 3, med den forudsætning, at når n er 1, er X ikke CH2.
3. Forbindelse til anvendelse ifølge krav 1, hvor forbindelsen med formlen I har formlen IB
hvor Ri, R2 og R3 er identiske eller forskellige og betegner hydrogen, halogen, alkyl, nitro, amino, alkylcarbonylamino, alkylamino eller dialkylaminogruppe; R4 betegner -alkyl-aryl eller -alkyl-heteroaryl; X betegner CH2, oxygenatom eller svovlatom; og n er 2 eller 3.
4. Forbindelse til anvendelse ifølge krav 1,2 eller 3, hvor X er O.
5. Forbindelse til anvendelse ifølge ethvert af de foregående krav, hvor n er 2 eller 3.
6. Forbindelse til anvendelse ifølge ethvert af de foregående krav, hvor i det mindste én af Ri, R2 og R3 er fluor.
7. Forbindelse til anvendelse ifølge ethvert af de foregående krav, hvor forbindelsen med formlen I er tilvejebragt som (R)- eller (S)-enantiomeren.
8. Forbindelse til anvendelse ifølge krav 7, hvor forbindelsen med formlen I er tilvejebragt som (R)-enantiomeren.
9. Forbindelse til anvendelse ifølge krav 1, hvor forbindelsen med formlen I er valgt blandt: (S)-5-(2-aminoethyl)-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazol-2-thion; (S)-5-(2-aminoethyl)-1-(5,7-difluor-1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydro-imidazol-2-thion; (R)-5-(2-aminoethyl)-1-chroman-3-yl-1,3-dihydroimidazol-2-thion; (R)-5-(2-aminoethyl)-1-(6-hydroxychroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-aminoethyl)-1-(8-hydroxychroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-aminoethyl)-1-(6-methoxychroman-3-yl)-1,3-dihydroimidazol-2-thion;
(R)-5-(2-aminoethyl)-1-(8-methoxychroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-aminoethyl)-1-(6-fluorchroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-aminoethyl)-1-(8-fluorchroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-aminoethyl)-1-(6,7-difluorchroman-3-yl)-1,3-dihydroimidazol-2-thion; (R) -5-(2-aminoethyl)-1-(6,8-difluorchroman-3-yl)-1,3-dihydroimidazol-2-thion; (S) -5-(2-aminoethyl)-1-(6,8-difluorchroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-aminoethyl)-1-(6,7,8-trifluorchroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-aminoethyl)-1-(6-chloro-8-methoxychroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-aminoethyl)-1-(6-methoxy-8-chlorochroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-aminoethyl)-1-(6-nitrochroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-aminoethyl)-1-(8-nitrochroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-aminoethyl)-1-[6-(acetylamino)chroman-3-yl]-1,3-dihydroimidazol-2-thion; (R)-5-aminomethyl-1 -chroman-3-yl-1,3-dihydroimidazol-2-thion; (R)-5-aminomethyl-1-(6-hydroxychroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-aminoethyl)-1-(6-hydroxy-7-benzylchroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-aminomethyl-1-(6,8-difluorchroman-3-yl)-1,3-dihydroimidazol-2-thion; (R) -5-(3-aminopropyl)-1-(6,8-difluorchroman-3-yl)-1,3-dihydroimidazol-2-thion; (S) -5-(3-aminopropyl)-1-(5,7-difluor-1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydro-imidazol-2-thion; (R,S)-5-(2-aminoethyl)-1-(6-hydroxythiochroman-3-yl)-1,3-dihydroimidazol-2-thion; (R,S)-5-(2-aminoethyl)-1-(6-methoxythiochroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-benzylaminoethyl)-1-(6-methoxychroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-benzylaminoethyl)-1-(6-hydroxychroman-3-yl)-1,3-dihydroimidazol-2-thion; (R)-1-(6-hydroxychroman-3-yl)-5-(2-methylaminoethyl)-1,3-dihydroimidazol-2-thion; (R)-1-(6,8-difluorchroman-3-yl)-5-(2-methylaminoethyl)-1,3-dihydroimidazol-2-thion; (R)-1-chroman-3-yl-5-(2-methylaminoethyl)-1,3-dihydroimidazol-2-thion; (R)-5-(2-(benzylamino)ethyl)-1 -(6,8-difluorchroman-3-yl)-1 H-imidazol-2(3H)-thion; eller et farmaceutisk acceptabelt salt deraf.
10. Forbindelse til anvendelse ifølge krav 8, hvor forbindelsen med formlen I er tilvejebragt i form af hydrochloridsaltet.
11. Forbindelse til anvendelse ifølge krav 1 eller 2, hvor forbindelsen med formlen I er (R)-5-(2-aminoethyl)-1 -(6,8-difluorchroman-3-yl)-1,3-dihydroimidazol-2-thion eller et farmaceutisk acceptabelt salt deraf.
12. Forbindelse til anvendelse ifølge krav 11, hvor forbindelsen med formlen I er hydrochloridsalt af (R)-5-(2-aminoethyl)-1 -(6,8-difluorchroman-3-yl)-1,3-dihydro-imidazol-2-thion.
13. Forbindelse til anvendelse ifølge krav 1 eller 3, hvor R4 betegner -CFF-aryl eller -CH2-heteroaryl.
14. Forbindelse til anvendelse ifølge krav 13, hvor R4 er benzyl.
15. Forbindelse til anvendelse ifølge krav 1, hvor forbindelsen med formlen I har formlen X:
16. Forbindelse til anvendelse ifølge krav 1 eller 3, hvor forbindelsen med formlen I er (R)-5-(2-(benzylamino)ethyl)-1 -(6,8-difluorchroman-3-yl)-1 H-imidazol-2(3H)-thion eller et farmaceutisk acceptabelt salt deraf.
17. Forbindelse til anvendelse ifølge krav 15, hvor forbindelsen med formlen I er (R)-5-(2-(benzylamino)ethyl)-1-(6,8-difluorchroman-3-yl)-1H-imidazol-2(3H)-thion.
18. Forbindelse til anvendelse ifølge ethvert af de foregående krav, hvor den i det mindste ene anden aktive farmaceutiske ingrediens er én eller flere valgt fra den følgende liste: epoprostenol, iloprost, bosentan, ambrisentan, sitaxentan, sildenafil, tadalafil, amlodipin, felodipin, diltiazem, nifedipin, nicardipin-isosorbid-dinitrat, isosorbid-5-mononitrat, warfarin, captopril, enalapril, lisinopril, benazepril, fosinopril, trandolapril, quinapril, ramipril, perindopril, zofenopril, cilazapril, imidapril, losartan, candersartan, olmesartan, irbesartan, eprosartan, telmisartan, valsartan, acetazolamid, dichlorphenamid, methazolamid, furosemid, ethacrynsyre, torasemid (torsemid), azosemid (axosemid), piretanid, tripamid, hydrochlorothiazid, chlorothiazid, bendroflumethiazid, methyclothiazid, polythiazid, trichlormethiazid, chlorthalidon, indapamid, metolazon, quinethazon, amilorid, triamteren, spironolacton, canrenon,
kaliumcanrenoat og eplerenon.
19. Forbindelse med formlen I eller et farmaceutisk acceptabelt salt deraf som angivet i ethvert af de foregående krav, til anvendelse ved behandlingen af lungeskade, omfattende én eller flere af følgende tilstande, åndedrætsbesvær, kortåndethed, træthed, svimmelhed, opsvulmning af ankler eller ben (ødem), blå læber og hud (cyanose), brystsmerte, hurtig puls og palpitationer, eventuelt i kombination med i det mindste én anden aktiv farmaceutisk ingrediens.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261726119P | 2012-11-14 | 2012-11-14 | |
| PCT/PT2013/000065 WO2014077715A1 (en) | 2012-11-14 | 2013-11-14 | 1,3-dihydroimidazole-2-thione derivatives for use in the treatment of pulmonary arterial hypertension and lung injury |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2919780T3 true DK2919780T3 (da) | 2018-11-26 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK13803292.5T DK2919780T3 (da) | 2012-11-14 | 2013-11-14 | 1,3-Dihydroimidazol-2-thionderivater til anvendelse ved behandlingen af pulmonær arteriel hypertension og lungeskade |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US9604970B2 (da) |
| EP (1) | EP2919780B1 (da) |
| JP (1) | JP6373275B2 (da) |
| KR (1) | KR102259938B1 (da) |
| CN (1) | CN105025895B (da) |
| AU (1) | AU2013345494B2 (da) |
| BR (1) | BR112015010969B1 (da) |
| CA (1) | CA2890920C (da) |
| CY (1) | CY1120953T1 (da) |
| DK (1) | DK2919780T3 (da) |
| ES (1) | ES2693025T3 (da) |
| HK (1) | HK1215393A1 (da) |
| HR (1) | HRP20181651T1 (da) |
| IN (1) | IN2015DN04089A (da) |
| LT (1) | LT2919780T (da) |
| MX (1) | MX355422B (da) |
| PL (1) | PL2919780T3 (da) |
| PT (1) | PT2919780T (da) |
| RS (1) | RS57874B1 (da) |
| RU (1) | RU2718055C2 (da) |
| SI (1) | SI2919780T1 (da) |
| TR (1) | TR201815850T4 (da) |
| WO (1) | WO2014077715A1 (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2693025T3 (es) | 2012-11-14 | 2018-12-07 | Bial - Portela & Ca., S.A. | Derivados de 1,3-dihidroimidazol-2-tiona para su uso en el tratamiento de hipertensión arterial pulmonar y lesión pulmonar |
| GB201810395D0 (en) * | 2018-06-25 | 2018-08-08 | Bial Portela & Ca Sa | Formulations comprising dopamine-beta-hydroxylase inhibitors and methods for their preparation |
| WO2021005623A1 (en) * | 2019-07-08 | 2021-01-14 | Msd Wellcome Trust Hilleman Laboratories Pvt. Ltd. | A vaccine formulation for protection against enterotoxigenic e. coli (etec) and cholera |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH0623107B2 (ja) * | 1990-11-16 | 1994-03-30 | 帝人株式会社 | プロスタサイクリン類を有効成分とする薬学的組成物 |
| ATE243199T1 (de) * | 1994-04-26 | 2003-07-15 | Syntex Llc | Benzocyclohexylimidazolthion-derivate |
| TW536540B (en) | 1997-01-30 | 2003-06-11 | Bristol Myers Squibb Co | Endothelin antagonists: N-[[2'-[[(4,5-dimethyl-3-isoxazolyl)amino]sulfonyl]-4-(2-oxazolyl)[1,1'-biphenyl]-2-yl]methyl]-N,3,3-trimethylbutanamide and N-(4,5-dimethyl-3-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-oxazolyl)[1,1'-biphe |
| US7125904B2 (en) * | 2002-10-11 | 2006-10-24 | Portela & C.A., S.A. | Peripherally-selective inhibitors of dopamine-β-hydroxylase and method of their preparation |
| US20040102361A1 (en) * | 2002-11-27 | 2004-05-27 | Frederic Bodin | Pharmaceutical composition for the treatment of pulmonary arterial hypertension |
| GB0600709D0 (en) | 2006-01-13 | 2006-02-22 | Portela & Ca Sa | Drug combinations |
| GB0610804D0 (en) * | 2006-05-31 | 2006-07-12 | Portela & Ca Sa | New crystal forms |
| GB0700635D0 (en) | 2007-01-12 | 2007-02-21 | Portela & Ca Sa | Therapy |
| EP2146707A2 (en) * | 2007-05-03 | 2010-01-27 | Abraxis BioScience, LLC | Methods and compositions for treating pulmonary hypertension |
| GB0708818D0 (en) * | 2007-05-08 | 2007-06-13 | Portela & Ca Sa | Compounds |
| WO2009072915A1 (en) * | 2007-12-05 | 2009-06-11 | Bial - Portela & Ca., S.A. | New salts and crystal forms |
| BRPI0821970A2 (pt) | 2008-01-03 | 2015-06-23 | Biomarin Pharm Inc | Análogos de pterina para tratamento de condição responsiva a bh4 |
| AR070841A1 (es) * | 2008-03-13 | 2010-05-05 | Bial Portela & Ca Sa | Proceso de hidrogenacion catalitica asimetrica |
| AR071632A1 (es) * | 2008-05-06 | 2010-06-30 | Bial Portela & Ca Sa | Proceso catalitico para hidrogenacion asimetrica en la sintesis de inhibidores de la dopamina-beta-hidroxilasa" |
| DE102008054205A1 (de) * | 2008-10-31 | 2010-05-06 | Bayer Schering Pharma Aktiengesellschaft | Verwendung von Helium-Sauerstoff-Gasgemischen zur Behandlung der pulmonalen arteriellen Hypertonie |
| JP6161538B2 (ja) * | 2010-12-22 | 2017-07-12 | バイアル−ポルテラ アンド シーエー，エス．エー． | 結晶形及びその製造方法 |
| ES2693025T3 (es) | 2012-11-14 | 2018-12-07 | Bial - Portela & Ca., S.A. | Derivados de 1,3-dihidroimidazol-2-tiona para su uso en el tratamiento de hipertensión arterial pulmonar y lesión pulmonar |
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- 2013-11-14 ES ES13803292.5T patent/ES2693025T3/es active Active
- 2013-11-14 RS RS20181204A patent/RS57874B1/sr unknown
- 2013-11-14 DK DK13803292.5T patent/DK2919780T3/da active
- 2013-11-14 PT PT13803292T patent/PT2919780T/pt unknown
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- 2013-11-14 CA CA2890920A patent/CA2890920C/en not_active Expired - Fee Related
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- 2013-11-14 RU RU2015120164A patent/RU2718055C2/ru not_active Application Discontinuation
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- 2013-11-14 MX MX2015005910A patent/MX355422B/es active IP Right Grant
- 2013-11-14 BR BR112015010969-1A patent/BR112015010969B1/pt not_active IP Right Cessation
- 2013-11-14 PL PL13803292T patent/PL2919780T3/pl unknown
- 2013-11-14 LT LTEP13803292.5T patent/LT2919780T/lt unknown
-
2016
- 2016-03-23 HK HK16103398.4A patent/HK1215393A1/zh not_active IP Right Cessation
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2017
- 2017-02-14 US US15/432,616 patent/US10308640B2/en not_active Expired - Fee Related
-
2018
- 2018-10-11 HR HRP20181651TT patent/HRP20181651T1/hr unknown
- 2018-10-30 CY CY20181101117T patent/CY1120953T1/el unknown
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2019
- 2019-04-16 US US16/385,350 patent/US20190241545A1/en not_active Abandoned
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