HRP20171397T4 - Postupak proizvodnje liganada amiloida beta obilježenih s f-18 - Google Patents
Postupak proizvodnje liganada amiloida beta obilježenih s f-18 Download PDFInfo
- Publication number
- HRP20171397T4 HRP20171397T4 HRP20171397T HRP20171397T4 HR P20171397 T4 HRP20171397 T4 HR P20171397T4 HR P20171397 T HRP20171397 T HR P20171397T HR P20171397 T4 HRP20171397 T4 HR P20171397T4
- Authority
- HR
- Croatia
- Prior art keywords
- group
- compound
- formula
- sulfonyloxy
- hplc
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 102000013455 Amyloid beta-Peptides Human genes 0.000 title 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 title 1
- 239000003446 ligand Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims 13
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 8
- -1 4-methoxytrityl Chemical group 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- 239000012062 aqueous buffer Substances 0.000 claims 4
- 235000010323 ascorbic acid Nutrition 0.000 claims 4
- 239000011668 ascorbic acid Substances 0.000 claims 4
- 238000004128 high performance liquid chromatography Methods 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 229940072107 ascorbate Drugs 0.000 claims 2
- 229960005070 ascorbic acid Drugs 0.000 claims 2
- 239000000872 buffer Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000006242 amine protecting group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 239000012025 fluorinating agent Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 239000007972 injectable composition Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000000163 radioactive labelling Methods 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000012064 sodium phosphate buffer Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0453—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0455—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/12—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by a special physical form, e.g. emulsion, microcapsules, liposomes, characterized by a special physical form, e.g. emulsions, dispersions, microcapsules
- A61K51/121—Solutions, i.e. homogeneous liquid formulation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Physics & Mathematics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (10)
1. Postupak proizvodnje spoja Formule I
,
naznačen time što se sastoji u koracima:
Korak 1: radioaktivnog obilježavanja spoja Formule II fluorirajućim sredstvom koje sadrži F-18, kako bi se dobilo spoj Formule I, ako R = H, ili kako bi se dobilo spoj Formule III, ako R = PG
Korak 2: ako R = PG, odcjepljivanja zaštitne skupine PG kako bi se dobilo spoj Formule I
Korak 3: pročišćavanja i formuliranja spoja Formule I
gdje:
n = 1-6,
X se bira iz skupine koju čine
a) CH,
b) N,
R se bira iz skupine koju čine
a) H,
b) PG,
PG je "zaštitna skupina za amin",
LG je izlazna skupina,
gdje se u koraku 3 upotrebljava postupak HPLC, gdje otapalo ili smjesa otapala za HPLC je dio injekcijske formulacije spoja I, pogodne za injiciranje kod ljudi, gdje se otapalo za HPLC bira iz skupine koju čine etanol, vodeni pufer ili smjesa etanol/vodeni pufer.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što se PG bira iz skupine koju čine:
a) Boc,
b) tritil i
c) 4-metoksitritil.
3. Postupak u skladu s patentnim zahtjevom 1 ili 2, naznačen time što se LG bira iz skupine koju čine:
a) halogen i
b) sulfoniloksi,
gdje je halogen klor, brom ili jod.
4. Postupak u skladu s patentnim zahtjevom 3, naznačen time što se sulfoniloksi bira iz skupine koju čine:
a) metansulfoniloksi,
b) p-toluensulfoniloksi,
c) (4-nitrofenil)sulfoniloksi,
d) (4-bromfenil)sulfoniloksi.
5. Postupak u skladu s patentnim zahtjevom 1, naznačen time što n = 3, a X = CH.
6. Postupak u skladu s patentnim zahtjevom 1, naznačen time što n = 3, X = CH, R = Boc, a LG = metansulfoniloksi.
7. Postupak u skladu s patentnim zahtjevima 1-6, naznačen time što se vodeni pufer bira iz skupine koju čine otopina natrijevog klorida, natrijev fosfatni pufer, askorbinska kiselina, askorbatni pufer, ili njihove smjese.
8. Postupak u skladu s patentnim zahtjevima 1-7, naznačen time što je otapalo za HPLC smjesa etanola s vodenim puferom koji sadrži askorbinsku kiselinu ili askorbatni pufer ili njihove smjese.
9. Postupak u skladu s patentnim zahtjevima 1-8, naznačen time što se upotrebljava 10-50 µmol spoja Formule II.
10. Postupak u skladu s patentnim zahtjevima 1-9, naznačen time što se postupak provodi kao posve automatizirani postupak.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10164949 | 2010-06-04 | ||
| PCT/EP2011/058820 WO2011151283A1 (en) | 2010-06-04 | 2011-05-30 | Method for production of f-18 labeled amyloid beta ligands |
| EP11723431.0A EP2579902B2 (en) | 2010-06-04 | 2011-05-30 | Method for production of f-18 labeled amyloid beta ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20171397T1 HRP20171397T1 (hr) | 2017-11-03 |
| HRP20171397T4 true HRP20171397T4 (hr) | 2019-11-15 |
Family
ID=44584930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20171397T HRP20171397T4 (hr) | 2010-06-04 | 2017-09-15 | Postupak proizvodnje liganada amiloida beta obilježenih s f-18 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US20130209363A1 (hr) |
| EP (1) | EP2579902B2 (hr) |
| JP (2) | JP5869562B2 (hr) |
| KR (1) | KR101761451B1 (hr) |
| CN (1) | CN103269724B (hr) |
| AU (1) | AU2011260421B2 (hr) |
| BR (1) | BR112012030935B1 (hr) |
| CA (1) | CA2801530C (hr) |
| DK (1) | DK2579902T4 (hr) |
| EA (1) | EA022897B1 (hr) |
| ES (1) | ES2642086T5 (hr) |
| HR (1) | HRP20171397T4 (hr) |
| HU (1) | HUE033237T2 (hr) |
| IL (1) | IL223358A (hr) |
| LT (1) | LT2579902T (hr) |
| MX (1) | MX345069B (hr) |
| PL (1) | PL2579902T5 (hr) |
| PT (1) | PT2579902T (hr) |
| SG (1) | SG185782A1 (hr) |
| SI (1) | SI2579902T2 (hr) |
| TW (1) | TWI583397B (hr) |
| WO (1) | WO2011151283A1 (hr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103328011A (zh) * | 2010-06-04 | 2013-09-25 | 皮拉马影像股份公司 | 生产F-18标记的β-淀粉样蛋白配体的方法 |
| SG185782A1 (en) | 2010-06-04 | 2013-01-30 | Piramal Imaging Sa | Method for production of f-18 labeled amyloid beta ligands |
| US11504430B2 (en) * | 2010-12-29 | 2022-11-22 | Ge Healthcare Limited | Eluent solution |
| PL2723394T3 (pl) | 2011-06-21 | 2018-11-30 | Piramal Imaging Sa | Preparaty fluorowanego stylbenu odpowiednie do zastosowań w obrazowaniu PET |
| BR112014009013A2 (pt) * | 2011-10-19 | 2017-05-02 | Piramal Imaging Sa | método melhorado para a produção de ligandos aß rotulados por f-18 |
| KR101326000B1 (ko) * | 2012-01-30 | 2013-11-07 | 재단법인 아산사회복지재단 | 수소이온 농도가 조절된 플루오린-18의 용리액 제조 및 이를 이용한 플루오린-18의 표지방법 |
| GB201318450D0 (en) * | 2013-10-18 | 2013-12-04 | Ge Healthcare Ltd | Closed evaporation system |
| DK3538161T3 (da) * | 2016-11-08 | 2022-09-05 | Univ California | Fremgangsmåder til flerdosissyntese af [F-18]FDDNP til kliniske indstillinger |
| JP7241013B2 (ja) * | 2017-03-17 | 2023-03-16 | 日本メジフィジックス株式会社 | イオフルパンの製造方法 |
| EA202091767A1 (ru) * | 2018-01-24 | 2021-02-16 | Ац Иммуне Са | Новый способ получения визуализирующего соединения |
| CN109867591B (zh) * | 2019-03-12 | 2020-11-06 | 浙江大学 | 18f标记的aie荧光/pet双模态探针及其制备方法和应用 |
| WO2024107620A1 (en) * | 2022-11-14 | 2024-05-23 | Eli Lilly And Company | Polymorphic forms of florbetapir precursor av-105 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5723103A (en) * | 1994-12-09 | 1998-03-03 | Vanderbilt University | Substituted benzamides and radioligand analogs and methods of use |
| BR0215913A (pt) | 2002-11-05 | 2005-08-09 | Ion Beam Applic Sa | Composição de radiofármacos rotulados com 18-f e processo para obtê-los |
| KR100789847B1 (ko) * | 2004-12-15 | 2007-12-28 | (주)퓨쳐켐 | 알코올 용매하에서 유기플루오로 화합물의 제조방법 |
| SI2213652T1 (sl) | 2004-12-17 | 2015-03-31 | The Trustees Of The University Of Pennsylvania | Derivati stilbena in njihova uporaba za vezavo in prikaz amiloidnih plakov |
| JP4738419B2 (ja) * | 2005-11-30 | 2011-08-03 | 富士フイルムＲｉファーマ株式会社 | アミロイドの凝集及び／又は沈着に起因する疾患の診断薬及び治療薬 |
| PT1999109E (pt) | 2006-03-30 | 2012-03-16 | Univ Pennsylvania | Derivados de estirilpiridina e sua utilização para ligação e obtenção de imagens de placas amilóides |
| WO2008009444A1 (en) | 2006-07-19 | 2008-01-24 | Van Dulmen, Adrianus, A. | Use of ethanol for stabilizing a single-vial liquid formulation of a radiolabeled peptide |
| EP2214722A1 (en) | 2007-11-07 | 2010-08-11 | GE Healthcare BV | Stabilization of radiopharmaceuticals |
| HUE033649T2 (en) | 2008-12-31 | 2017-12-28 | Avid Radiopharmaceuticals Inc | Synthesis of 18F-labeled styryl pyridines from tosylate precursors and their stable pharmaceutical preparations |
| US8968701B2 (en) * | 2009-07-10 | 2015-03-03 | Piramal Imaging Sa | Usage of low to medium-pressure liquid chromatography for the purification of radiotracers |
| SG185782A1 (en) | 2010-06-04 | 2013-01-30 | Piramal Imaging Sa | Method for production of f-18 labeled amyloid beta ligands |
-
2011
- 2011-05-30 SG SG2012087367A patent/SG185782A1/en unknown
- 2011-05-30 PL PL11723431T patent/PL2579902T5/pl unknown
- 2011-05-30 JP JP2013512858A patent/JP5869562B2/ja active Active
- 2011-05-30 PT PT117234310T patent/PT2579902T/pt unknown
- 2011-05-30 WO PCT/EP2011/058820 patent/WO2011151283A1/en active Application Filing
- 2011-05-30 AU AU2011260421A patent/AU2011260421B2/en active Active
- 2011-05-30 SI SI201131295T patent/SI2579902T2/sl unknown
- 2011-05-30 ES ES11723431T patent/ES2642086T5/es active Active
- 2011-05-30 MX MX2012014117A patent/MX345069B/es active IP Right Grant
- 2011-05-30 KR KR1020137000136A patent/KR101761451B1/ko active IP Right Grant
- 2011-05-30 LT LTEP11723431.0T patent/LT2579902T/lt unknown
- 2011-05-30 US US13/702,007 patent/US20130209363A1/en not_active Abandoned
- 2011-05-30 DK DK11723431.0T patent/DK2579902T4/da active
- 2011-05-30 EP EP11723431.0A patent/EP2579902B2/en active Active
- 2011-05-30 CA CA2801530A patent/CA2801530C/en active Active
- 2011-05-30 BR BR112012030935-8A patent/BR112012030935B1/pt active IP Right Grant
- 2011-05-30 CN CN201180027675.XA patent/CN103269724B/zh active Active
- 2011-05-30 EA EA201201645A patent/EA022897B1/ru not_active IP Right Cessation
- 2011-05-30 HU HUE11723431A patent/HUE033237T2/hu unknown
- 2011-05-31 TW TW100119101A patent/TWI583397B/zh active
-
2012
- 2012-11-29 IL IL223358A patent/IL223358A/en active IP Right Grant
-
2015
- 2015-10-23 JP JP2015208782A patent/JP2016047831A/ja active Pending
-
2016
- 2016-03-07 US US15/062,604 patent/US9592308B2/en active Active
-
2017
- 2017-09-15 HR HRP20171397T patent/HRP20171397T4/hr unknown
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