CU24274B1 - Compuestos intermediarios para la síntesis de treprostinil - Google Patents
Compuestos intermediarios para la síntesis de treprostinilInfo
- Publication number
- CU24274B1 CU24274B1 CUP2014000135A CU20140135A CU24274B1 CU 24274 B1 CU24274 B1 CU 24274B1 CU P2014000135 A CUP2014000135 A CU P2014000135A CU 20140135 A CU20140135 A CU 20140135A CU 24274 B1 CU24274 B1 CU 24274B1
- Authority
- CU
- Cuba
- Prior art keywords
- formula
- dichlorobenzyl
- intermediates
- methyl
- space
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 229960005032 treprostinil Drugs 0.000 title abstract 2
- PAJMKGZZBBTTOY-ZFORQUDYSA-N treprostinil Chemical compound C1=CC=C(OCC(O)=O)C2=C1C[C@@H]1[C@@H](CC[C@@H](O)CCCCC)[C@H](O)C[C@@H]1C2 PAJMKGZZBBTTOY-ZFORQUDYSA-N 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- -1 benzyloxymethyl Chemical group 0.000 abstract 3
- 239000000543 intermediate Substances 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 abstract 2
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 229960001123 epoprostenol Drugs 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
- C07C47/565—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups all hydroxy groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- 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
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P31/00—Preparation of compounds containing a five-membered ring having two side-chains in ortho position to each other, and having at least one oxygen atom directly bound to the ring in ortho position to one of the side-chains, one side-chain containing, not directly bound to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having at least one oxygen atom bound in gamma-position to the ring, e.g. prostaglandins
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/002—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by oxidation/reduction reactions
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/14—Benz[f]indenes; Hydrogenated benz[f]indenes
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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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
Abstract
<p>La presente invención se refiere a compuestos intermediarios para producir treprostinil, es un análogo sintético de prostaciclina (PGI2). Dichos compuestos intermediarios tienen la fórmula I o la fórmula II,</p> <p>ESPACIO PARA FÓRMULAS I y II</p> <p>en donde X es Br</p> <p>Y es H</p> <p>PG1 se selecciona entre el grupo que consiste en metilo, metoximetilo, benciloximetilo, metoxietoximetilo, bencilo, 4-metoxibencilo, 2,6-diclorobencilo, 3,4-diclorobencilo; -CH2COOH, -CH2COORx, y –CH2CH2OROPG2;</p> <p>PG2 es THP, SiR1R2R3; O –CH2ORX;</p> <p>R1, R2 y R3 son independientemente uno del otro seleccionado de grupo que consiste de metilo, isopropilo, t-butilo y fenilo;</p> <p>Ra es hidrógeno, hidroxi –ORx, -OCOORx, OSO2Rx, Cl, Br, F, I, - SRx, o –SO2Rx;</p> <p>Rx es Cl-4 alquilo o arilo.</p> <p>También la invención se refiere al compuesto intermediario de la fórmula 17:</p> <p>ESPACIO PARA FÓMULA 17</p>
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261650836P | 2012-05-23 | 2012-05-23 | |
| EP12172191.4A EP2674413B1 (en) | 2012-06-15 | 2012-06-15 | Process for the preparation of treprostinil and derivatives thereof |
| PCT/EP2013/060472 WO2013174848A2 (en) | 2012-05-23 | 2013-05-22 | Improved process for the preparation of treprostinil and derivatives thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CU20140135A7 CU20140135A7 (es) | 2015-04-29 |
| CU24274B1 true CU24274B1 (es) | 2017-09-06 |
Family
ID=46262002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CUP2014000135A CU24274B1 (es) | 2012-05-23 | 2013-05-22 | Compuestos intermediarios para la síntesis de treprostinil |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US9346738B2 (es) |
| EP (2) | EP2674413B1 (es) |
| JP (1) | JP6219376B2 (es) |
| KR (1) | KR102080264B1 (es) |
| CN (2) | CN107963962A (es) |
| AU (1) | AU2013265351B2 (es) |
| BR (1) | BR112014028969B1 (es) |
| CA (2) | CA3118552C (es) |
| CL (1) | CL2014003165A1 (es) |
| CO (1) | CO7240368A2 (es) |
| CR (1) | CR20140534A (es) |
| CU (1) | CU24274B1 (es) |
| DK (2) | DK2674413T3 (es) |
| DO (1) | DOP2014000266A (es) |
| EA (1) | EA027202B1 (es) |
| EC (1) | ECSP14028230A (es) |
| ES (2) | ES2639823T3 (es) |
| GE (1) | GEP201606548B (es) |
| GT (1) | GT201400262A (es) |
| HR (1) | HRP20171340T1 (es) |
| HU (2) | HUE034485T2 (es) |
| IL (1) | IL235734B (es) |
| LT (1) | LT2674413T (es) |
| MA (1) | MA37611B1 (es) |
| ME (1) | ME02861B (es) |
| MX (1) | MX358418B (es) |
| MY (1) | MY174852A (es) |
| NI (1) | NI201400135A (es) |
| NZ (1) | NZ701041A (es) |
| PE (1) | PE20150712A1 (es) |
| PH (1) | PH12014502604A1 (es) |
| PL (2) | PL2674413T3 (es) |
| PT (2) | PT2674413T (es) |
| RS (1) | RS56304B1 (es) |
| SG (1) | SG11201407662WA (es) |
| SI (1) | SI2674413T1 (es) |
| TN (1) | TN2014000486A1 (es) |
| UA (1) | UA118337C2 (es) |
| WO (1) | WO2013174848A2 (es) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2943479B1 (en) | 2013-01-11 | 2020-04-15 | Corsair Pharma, Inc. | Prodrugs of treprostinil |
| US9505737B2 (en) | 2013-01-11 | 2016-11-29 | Corsair Pharma, Inc. | Treprostinil derivative compounds and methods of using same |
| JP6491203B2 (ja) | 2013-10-25 | 2019-03-27 | インスメッド インコーポレイテッド | プロスタサイクリン化合物、組成物およびその使用方法 |
| CN104892555B (zh) * | 2014-03-04 | 2019-03-08 | 江苏豪森药业集团有限公司 | 曲前列尼尔中间体的制备方法 |
| HU231186B1 (hu) * | 2014-10-08 | 2021-06-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás treprostinil és sói előállítására |
| WO2016081658A1 (en) | 2014-11-18 | 2016-05-26 | Insmed Incorporated | Methods of manufacturing treprostinil and treprostinil derivative prodrugs |
| TWI540121B (zh) | 2014-12-01 | 2016-07-01 | 臺灣永光化學工業股份有限公司 | 曲前列環素二乙醇胺之合成方法及新穎中間體 |
| US9643911B2 (en) | 2015-06-17 | 2017-05-09 | Corsair Pharma, Inc. | Treprostinil derivatives and compositions and uses thereof |
| US9394227B1 (en) | 2015-06-17 | 2016-07-19 | Corsair Pharma, Inc. | Treprostinil derivatives and compositions and uses thereof |
| KR101830693B1 (ko) * | 2016-04-28 | 2018-02-21 | 연성정밀화학(주) | 트레프로스티닐의 제조방법 및 이를 위한 중간체 |
| EP3515430A1 (en) | 2016-09-26 | 2019-07-31 | United Therapeutics Corporation | Treprostinil prodrugs |
| EP3498283A1 (en) | 2017-12-14 | 2019-06-19 | Ipsol AG | Glycosidic derivatives of treprostinil |
| CN108875295A (zh) * | 2018-06-21 | 2018-11-23 | 华北电力科学研究院有限责任公司 | 一种利用析因实验设计指导有机物分子修饰改性的方法 |
| JP7455144B2 (ja) | 2019-04-29 | 2024-03-25 | インスメッド インコーポレイテッド | トレプロスチニルプロドラッグの乾燥粉末組成物およびその使用方法 |
| AU2020337342A1 (en) | 2019-08-23 | 2022-02-24 | United Therapeutics Corporation | Treprostinil prodrugs |
| CN115916212A (zh) | 2020-04-17 | 2023-04-04 | 联合治疗公司 | 曲前列尼尔用于治疗间质性肺病 |
| CN116113415A (zh) | 2020-06-09 | 2023-05-12 | 联合治疗公司 | 曲前列尼尔的富马酰基二酮哌啶前药 |
| WO2022132655A1 (en) | 2020-12-14 | 2022-06-23 | United Therapeutics Corporation | Methods of treating disease with treprostinil prodrugs |
| EP4301372A1 (en) | 2021-03-03 | 2024-01-10 | United Therapeutics Corporation | A dry powder composition of trestinil and its prodrug thereof and further comprising comprising (e)-3,6-bis[4-(n-carbonyl-2-propenyl)amidobutyl]-2,5-diketopiperazine (fdkp) |
| WO2023154705A1 (en) | 2022-02-08 | 2023-08-17 | United Therapeutics Corporation | Treprostinil iloprost combination therapy |
| US20240287105A1 (en) | 2023-01-19 | 2024-08-29 | United Therapeutics Corporation | Treprostinil analogs and related methods of making and using |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6242842B1 (en) | 1996-12-16 | 2001-06-05 | Siemens Matsushita Components Gmbh & Co. Kg | Electrical component, in particular saw component operating with surface acoustic waves, and a method for its production |
| US6441245B1 (en) * | 1997-10-24 | 2002-08-27 | United Therapeutics Corporation | Process for stereoselective synthesis of prostacyclin derivatives |
| US6242482B1 (en) * | 2000-06-05 | 2001-06-05 | United Therapeutics Corporation | Prostaglandin compounds and derivatives thereof, compositions containing the same and method of using the same for the treatment of congestive heart failure |
| US6700025B2 (en) * | 2001-01-05 | 2004-03-02 | United Therapeutics Corporation | Process for stereoselective synthesis of prostacyclin derivatives |
| ES2622471T5 (es) * | 2003-05-22 | 2020-07-23 | United Therapeutics Corp | Compuestos y procedimientos para la administración de análogos de prostaciclina |
| JP6046034B2 (ja) * | 2010-06-03 | 2016-12-14 | ユナイテッド セラピューティクス コーポレイション | トレプロスチニルの製造 |
| CA2710726C (en) * | 2010-07-22 | 2016-02-23 | Alphora Research Inc. | Synthesis of treprostinil and intermediates useful therein |
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2012
- 2012-06-15 DK DK12172191.4T patent/DK2674413T3/en active
- 2012-06-15 SI SI201231051T patent/SI2674413T1/sl unknown
- 2012-06-15 PL PL12172191T patent/PL2674413T3/pl unknown
- 2012-06-15 RS RS20170871A patent/RS56304B1/sr unknown
- 2012-06-15 ME MEP-2017-203A patent/ME02861B/me unknown
- 2012-06-15 ES ES12172191.4T patent/ES2639823T3/es active Active
- 2012-06-15 LT LTEP12172191.4T patent/LT2674413T/lt unknown
- 2012-06-15 PT PT121721914T patent/PT2674413T/pt unknown
- 2012-06-15 HU HUE12172191A patent/HUE034485T2/en unknown
- 2012-06-15 EP EP12172191.4A patent/EP2674413B1/en active Active
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2013
- 2013-05-22 ES ES13724809T patent/ES2702347T3/es active Active
- 2013-05-22 BR BR112014028969-7A patent/BR112014028969B1/pt active IP Right Grant
- 2013-05-22 UA UAA201413808A patent/UA118337C2/uk unknown
- 2013-05-22 NZ NZ701041A patent/NZ701041A/en unknown
- 2013-05-22 MX MX2014014237A patent/MX358418B/es active IP Right Grant
- 2013-05-22 EP EP13724809.2A patent/EP2861554B1/en active Active
- 2013-05-22 CU CUP2014000135A patent/CU24274B1/es unknown
- 2013-05-22 MA MA37611A patent/MA37611B1/fr unknown
- 2013-05-22 CA CA3118552A patent/CA3118552C/en active Active
- 2013-05-22 CA CA2873280A patent/CA2873280C/en active Active
- 2013-05-22 PT PT13724809T patent/PT2861554T/pt unknown
- 2013-05-22 KR KR1020147031805A patent/KR102080264B1/ko active IP Right Grant
- 2013-05-22 CN CN201711097647.0A patent/CN107963962A/zh active Pending
- 2013-05-22 HU HUE13724809A patent/HUE042516T2/hu unknown
- 2013-05-22 EA EA201401293A patent/EA027202B1/ru not_active IP Right Cessation
- 2013-05-22 PL PL13724809T patent/PL2861554T3/pl unknown
- 2013-05-22 US US14/401,826 patent/US9346738B2/en active Active
- 2013-05-22 WO PCT/EP2013/060472 patent/WO2013174848A2/en active Application Filing
- 2013-05-22 SG SG11201407662WA patent/SG11201407662WA/en unknown
- 2013-05-22 DK DK13724809.2T patent/DK2861554T3/en active
- 2013-05-22 CN CN201380026921.9A patent/CN104350035B/zh active Active
- 2013-05-22 MY MYPI2014003255A patent/MY174852A/en unknown
- 2013-05-22 JP JP2015513152A patent/JP6219376B2/ja active Active
- 2013-05-22 AU AU2013265351A patent/AU2013265351B2/en active Active
- 2013-05-22 PE PE2014002058A patent/PE20150712A1/es active IP Right Grant
- 2013-05-22 GE GEAP201313668A patent/GEP201606548B/en unknown
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2014
- 2014-11-17 IL IL235734A patent/IL235734B/en active IP Right Grant
- 2014-11-21 GT GT201400262A patent/GT201400262A/es unknown
- 2014-11-21 EC ECIEPI201428230A patent/ECSP14028230A/es unknown
- 2014-11-21 CR CR20140534A patent/CR20140534A/es unknown
- 2014-11-21 CL CL2014003165A patent/CL2014003165A1/es unknown
- 2014-11-21 TN TN2014000486A patent/TN2014000486A1/fr unknown
- 2014-11-21 CO CO14256345A patent/CO7240368A2/es unknown
- 2014-11-21 NI NI201400135A patent/NI201400135A/es unknown
- 2014-11-21 DO DO2014000266A patent/DOP2014000266A/es unknown
- 2014-11-21 PH PH12014502604A patent/PH12014502604A1/en unknown
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2017
- 2017-09-06 HR HRP20171340TT patent/HRP20171340T1/hr unknown
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