HRP20220201T1 - Postupak za pripremu pleuromutilina - Google Patents
Postupak za pripremu pleuromutilina Download PDFInfo
- Publication number
- HRP20220201T1 HRP20220201T1 HRP20220201TT HRP20220201T HRP20220201T1 HR P20220201 T1 HRP20220201 T1 HR P20220201T1 HR P20220201T T HRP20220201T T HR P20220201TT HR P20220201 T HRP20220201 T HR P20220201T HR P20220201 T1 HRP20220201 T1 HR P20220201T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- formula
- image
- mixture
- organic solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 7
- 238000002360 preparation method Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 32
- 239000000203 mixture Substances 0.000 claims 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000012296 anti-solvent Substances 0.000 claims 2
- 239000003495 polar organic solvent Substances 0.000 claims 2
- 238000001953 recrystallisation Methods 0.000 claims 2
- 229960002771 retapamulin Drugs 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000006242 amine protecting group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- -1 besyl Chemical group 0.000 claims 1
- 239000013058 crude material Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
Classifications
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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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/41—Y being a hydrogen or an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/08—Acetic acid
- C07C53/10—Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/145—Maleic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/08—Lactic acid
-
- 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
- C07B2200/07—Optical isomers
-
- 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
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/76—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members
- C07C2603/80—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members containing eight-membered rings
- C07C2603/82—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members containing eight-membered rings having three condensed rings with in total fourteen carbon atoms and having a having a [5.4.3.0(1,8)] ring structure, e.g. pleuromutiline
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- 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
Claims (5)
1. Postupak za pripravu spoja formule I
[image]
u obliku jednog stereoizomera u kristalnom obliku, naznačeno time, da postupak uključuje uklanjanje zaštite amino skupini bilo u spoju formule Ila
[image]
u smjesi spoja formule Ila sa spojem formule Ilb
[image]
gdje je R zaštitna skupina za amin, i
izoliranje spoja formule I dobivene u obliku jednog dijastereomera u kristalnom obliku ili izravno iz reakcijske smjese ili rekristalizacijom u organskom otapalu, pri čemu se spoj formule I izolira u oblik jednog dijastereomera u kristalnom obliku te se sastoji od jednog od sljedećih koraka:
a) tretiranja otopine spoja formule I u jednom stereoizomernom obliku dobivenom u polarnom organskom otapalu CH2Cl2, s protuotapalom odabranim između diizopropiletera (DIPE) ili terc-butil metil etera (MTBE), po mogućnosti DIPE
b) tretiranja otopine spoja formule I u jednom stereoizomernom obliku dobivenom u polarnom organskom otapalu CH2Cl2, nakon koncentriranja s alkoholom, kao što je n-butanol;
c) uzimanja izoliranog sirovog materijala spoja formule I u jednom stereoizomernom obliku, u eteru, npr. tetrahidrofuran (THF), i izborno tretiranje s protuotapalom odabranim između DIPE ili MTBE;
d) dobivanja spoja formule I u obliku jednog dijastereomera u kristalnom obliku putem (re-)kristalizacije u organskom otapalu, pri čemu je organsko otapalo alkohol, kao što je n-butanol.
2. Postupak u skladu s patentnim zahtjevom 1, naznačeno time, da se nadalje sastoji iz sljedećeg koraka
e) rekristalizacija kristalnog spoja dobivenog iz alkohola, kao što je n-butanol.
3. Postupak u skladu s patentnim zahtjevom 1 ili zahtjevom 2, naznačeno time, da se spoj formule IIa ili smjesa spoja formule IIa sa spojem formule IIb dobiva spajanjem bilo kojeg spoja formule IIIa
[image]
ili
smjesa spoja formule IIIa sa spojem formule IIIb
[image]
odnosno
pri čemu je R kao što je definirano u patentnom zahtjevu 1,
s aktiviranim 14-O-AKT-acetil-mutilinom, pri čemu je AKT aktivirajuća skupina, po izboru mesil, besil, tosil ili -OAKT je halogen, po izboru 14-O-AKT-acetil-mutilin je spoj formule
[image]
i izoliranje ili spoja formule IIa ili smjese spoja formule IIa sa spojem formule IIb, odnosno dobiven iz reakcijske smjese.
4. Postupak u skladu s patentnim zahtjevom 3, naznačeno time, što spoj formule IIa ili smjesa spoja formule IIIa sa spojem formule IIIb se dobiva uklanjanjem zaštite tiolne funkcije bilo u spoju formule Iva
[image]
ili u smjesi spoja IVa sa spojem formule IVb
[image]
odnosno
pri čemu je R kao što je definirano u patentnom zahtjevu 1, a R1 je tiol zaštitna skupina,
i izoliranje ili spoja formule IIIa, ili smjese spoja formule IIIa sa spojem od formule IIIb, odnosno dobivene iz reakcijske smjese.
5. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačeno time, što dalje uključuje korak pretvorbe spoja formule I u sol dodavanjem kiseline i izolacijom spoja u obliku soli, po izboru, kristalne soli.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20100450092 EP2399904A1 (en) | 2010-05-26 | 2010-05-26 | Process for the preparation of pleuromutilins |
| EP17197350.6A EP3299356B1 (en) | 2010-05-26 | 2011-05-23 | Process for the preparation of pleuromutilins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20220201T1 true HRP20220201T1 (hr) | 2022-04-29 |
Family
ID=42937801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20220201TT HRP20220201T1 (hr) | 2010-05-26 | 2011-05-23 | Postupak za pripremu pleuromutilina |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US9120727B2 (hr) |
| EP (3) | EP2399904A1 (hr) |
| JP (2) | JP6038021B2 (hr) |
| KR (1) | KR101935333B1 (hr) |
| CN (2) | CN105111117A (hr) |
| AU (1) | AU2011257938B2 (hr) |
| BR (1) | BR112012029982A2 (hr) |
| CA (1) | CA2799029C (hr) |
| DK (2) | DK3299356T3 (hr) |
| EA (1) | EA023273B1 (hr) |
| ES (2) | ES2659729T3 (hr) |
| HK (1) | HK1253006A1 (hr) |
| HR (1) | HRP20220201T1 (hr) |
| HU (2) | HUE035861T2 (hr) |
| IL (1) | IL222999A (hr) |
| MA (1) | MA34332B1 (hr) |
| MX (1) | MX347176B (hr) |
| MY (1) | MY164666A (hr) |
| NZ (1) | NZ603804A (hr) |
| PL (2) | PL3299356T3 (hr) |
| PT (2) | PT3299356T (hr) |
| SG (1) | SG185104A1 (hr) |
| SI (1) | SI3299356T1 (hr) |
| TN (1) | TN2012000506A1 (hr) |
| TR (1) | TR201802636T4 (hr) |
| TW (1) | TWI585073B (hr) |
| UA (1) | UA108378C2 (hr) |
| WO (1) | WO2011146954A1 (hr) |
| ZA (1) | ZA201208056B (hr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447294A (zh) * | 2014-11-24 | 2015-03-25 | 苏州乔纳森新材料科技有限公司 | 一种3-环己烯-1-甲酸的手性拆分方法 |
| JP6818019B2 (ja) * | 2015-06-17 | 2021-01-20 | ナブリヴァ セラピュティクス ゲーエムベーハー | レファムリンの注射可能医薬組成物 |
| WO2016203011A1 (en) | 2015-06-18 | 2016-12-22 | Mithra Pharmaceuticals S.A. | Orodispersible dosage unit containing an estetrol component |
| PL3701944T3 (pl) | 2015-06-18 | 2022-04-04 | Estetra Srl | Ulegająca rozpadowi w jamie ustnej jednostka dawkowana zawierająca składnik estetrolowy |
| TWI762573B (zh) | 2017-02-10 | 2022-05-01 | 奧地利商納畢瓦治療有限責任公司 | 截短側耳素之純化 |
| CN107417586A (zh) * | 2017-06-21 | 2017-12-01 | 华南农业大学 | 一种截短侧耳素类抗生素及其制备方法和应用 |
| JOP20200260A1 (ar) | 2018-04-19 | 2019-10-19 | Estetra Sprl | مركبات واستخداماتها للتخفيف من الأعراض المصاحبة لانقطاع الطمث |
| TWI801561B (zh) | 2018-04-19 | 2023-05-11 | 比利時商依思特拉私人有限責任公司 | 化合物及其用於緩解絕經相關症狀的用途 |
| TWI755055B (zh) | 2019-09-18 | 2022-02-11 | 台灣神隆股份有限公司 | 用於製備惡拉戈利鈉及其中間體的方法 |
| CN111170893B (zh) * | 2020-01-19 | 2022-04-26 | 郑州依米花手性药物研究有限公司 | Lefamulin的中间体化合物及其在Lefamulin制备中的应用 |
| EP4135682A1 (en) | 2020-04-17 | 2023-02-22 | Nabriva Therapeutics GMBH | Therapeutic use of pleuromutilins |
| WO2021209173A1 (en) | 2020-04-17 | 2021-10-21 | Nabriva Therapeutics GmbH | Novel therapeutic use of pleuromutilins |
| WO2023152115A1 (en) | 2022-02-09 | 2023-08-17 | Nabriva Therapeutics GmbH | Lefamulin and its derivatives for use in the treatment of a spiral shaped bacteria |
| EP4338732A1 (en) | 2022-09-16 | 2024-03-20 | Nabriva Therapeutics GMBH | Lefamulin and its derivatives for use in the treatment of tularemia |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61207370A (ja) * | 1985-03-11 | 1986-09-13 | Seitetsu Kagaku Co Ltd | ４−（メタンスルホニルオキシ）チオフエノ−ルの製法 |
| GB0017031D0 (en) * | 2000-07-11 | 2000-08-30 | Biochemie Gmbh | Antimicrobials |
| MXPA05000984A (es) * | 2002-07-24 | 2005-09-12 | Sandoz Ag | Derivados de pleuromutilina como antimicrobianos. |
| GB0308114D0 (en) * | 2003-04-08 | 2003-05-14 | Glaxo Group Ltd | Novel compounds |
| KR100745160B1 (ko) * | 2003-08-04 | 2007-08-01 | 조인트 스탁 컴퍼니 그린덱스 | 멜도늄 염, 그것의 제조방법 및 그것을 주성분으로 한약학적 조성물 |
| CA2536144C (en) * | 2003-08-18 | 2010-09-14 | H. Lundbeck A/S | Succinate and malonate salt of trans-4-(ir,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine and the use as a medicament |
| ES2335284T3 (es) * | 2003-09-03 | 2010-03-24 | Glaxo Group Limited | Nuevo procedimiento para preparar derivados de pleuromutilina. |
| CA2659987A1 (en) | 2006-07-20 | 2008-01-24 | Wms Gaming Inc. | Wagering game with special-event eligibility feature based on passive game play |
| EP1908750A1 (en) * | 2006-10-05 | 2008-04-09 | Nabriva Therapeutics Forschungs GmbH | Process for the preparation of pleuromutilins |
| SI1961735T1 (sl) * | 2007-02-22 | 2010-01-29 | Indena Spa | Postopek za pripravo acetatne soli (2r,3s)-3-fenilizoserin-metilestra |
| EP1972618A1 (en) * | 2007-03-20 | 2008-09-24 | Nabriva Therapeutics AG | Pleuromutilin derivatives for the treatment of diseases mediated by microbes |
| EP2014645A1 (en) * | 2007-07-13 | 2009-01-14 | Nabriva Therapeutics AG | Pleuromutilin derivatives and their use as antimicrobials |
| EP2159220A1 (en) * | 2008-09-02 | 2010-03-03 | Nabriva Therapeutics AG | Organic compounds |
-
2010
- 2010-05-26 EP EP20100450092 patent/EP2399904A1/en not_active Withdrawn
-
2011
- 2011-05-23 CN CN201510488095.0A patent/CN105111117A/zh active Pending
- 2011-05-23 WO PCT/AT2011/000237 patent/WO2011146954A1/en active Application Filing
- 2011-05-23 ES ES11724938.3T patent/ES2659729T3/es active Active
- 2011-05-23 TW TW100117950A patent/TWI585073B/zh active
- 2011-05-23 KR KR1020127030731A patent/KR101935333B1/ko active IP Right Grant
- 2011-05-23 PL PL17197350T patent/PL3299356T3/pl unknown
- 2011-05-23 DK DK17197350.6T patent/DK3299356T3/da active
- 2011-05-23 JP JP2013511476A patent/JP6038021B2/ja active Active
- 2011-05-23 EP EP17197350.6A patent/EP3299356B1/en active Active
- 2011-05-23 DK DK11724938.3T patent/DK2576505T3/en active
- 2011-05-23 TR TR2018/02636T patent/TR201802636T4/tr unknown
- 2011-05-23 CA CA2799029A patent/CA2799029C/en active Active
- 2011-05-23 PT PT171973506T patent/PT3299356T/pt unknown
- 2011-05-23 EA EA201291370A patent/EA023273B1/ru unknown
- 2011-05-23 AU AU2011257938A patent/AU2011257938B2/en active Active
- 2011-05-23 NZ NZ603804A patent/NZ603804A/en unknown
- 2011-05-23 SG SG2012080339A patent/SG185104A1/en unknown
- 2011-05-23 CN CN201180036554.1A patent/CN103080083B/zh active Active
- 2011-05-23 US US13/699,589 patent/US9120727B2/en active Active
- 2011-05-23 PL PL11724938T patent/PL2576505T3/pl unknown
- 2011-05-23 SI SI201132039T patent/SI3299356T1/sl unknown
- 2011-05-23 MX MX2012013645A patent/MX347176B/es active IP Right Grant
- 2011-05-23 EP EP11724938.3A patent/EP2576505B1/en active Active
- 2011-05-23 BR BR112012029982-4A patent/BR112012029982A2/pt not_active Application Discontinuation
- 2011-05-23 HU HUE11724938A patent/HUE035861T2/hu unknown
- 2011-05-23 UA UAA201214910A patent/UA108378C2/ru unknown
- 2011-05-23 ES ES17197350T patent/ES2909198T3/es active Active
- 2011-05-23 HU HUE17197350A patent/HUE057587T2/hu unknown
- 2011-05-23 HR HRP20220201TT patent/HRP20220201T1/hr unknown
- 2011-05-23 PT PT117249383T patent/PT2576505T/pt unknown
- 2011-05-23 MA MA35484A patent/MA34332B1/fr unknown
- 2011-05-23 MY MYPI2012700960A patent/MY164666A/en unknown
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2012
- 2012-10-23 TN TNP2012000506A patent/TN2012000506A1/en unknown
- 2012-10-25 ZA ZA2012/08056A patent/ZA201208056B/en unknown
- 2012-11-12 IL IL222999A patent/IL222999A/en active IP Right Grant
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2016
- 2016-09-08 JP JP2016175859A patent/JP6501742B2/ja active Active
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2018
- 2018-09-27 HK HK18112372.3A patent/HK1253006A1/zh unknown
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