HRP20170167T1 - Sinteza spojeva triazolopirimidina - Google Patents
Sinteza spojeva triazolopirimidina Download PDFInfo
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- HRP20170167T1 HRP20170167T1 HRP20170167TT HRP20170167T HRP20170167T1 HR P20170167 T1 HRP20170167 T1 HR P20170167T1 HR P20170167T T HRP20170167T T HR P20170167TT HR P20170167 T HRP20170167 T HR P20170167T HR P20170167 T1 HRP20170167 T1 HR P20170167T1
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Links
- 230000015572 biosynthetic process Effects 0.000 title claims 2
- 238000003786 synthesis reaction Methods 0.000 title 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 32
- -1 hydroxyethyl group Chemical group 0.000 claims 10
- 238000000034 method Methods 0.000 claims 10
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 9
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- 238000010511 deprotection reaction Methods 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 4
- 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 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000009935 nitrosation Effects 0.000 claims 1
- 238000007034 nitrosation reaction Methods 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- OEKWJQXRCDYSHL-FNOIDJSQSA-N ticagrelor Chemical compound C1([C@@H]2C[C@H]2NC=2N=C(N=C3N([C@H]4[C@@H]([C@H](O)[C@@H](OCCO)C4)O)N=NC3=2)SCCC)=CC=C(F)C(F)=C1 OEKWJQXRCDYSHL-FNOIDJSQSA-N 0.000 claims 1
- 229960002528 ticagrelor Drugs 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C07C217/52—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—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
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
-
- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (14)
1. Postupak za proizvodnju spoja sljedeće formule Va ili Vb:
[image]
naznačen time, da Pg je amino-zaštitna skupina, a Z je vodik, hidroksietil ili skupina koja se može pretvarati u hidroksietil, pri čemu postupak obuhvaća sljedeće korake:
(i) reakcija spoja sljedeće formule II':
[image]
gdje je Pg prethodno definiran,
sa spojem sljedeće formule VI odnosno VII:
[image]
gdje je Z prethodno definiran,
kako bi se dobio spoj sljedeće formule IIIa' odnosno IIIb':
[image]
dok su Pg i Z prethodno definirani,
(ii) redukcija nitro-skupine iz spoja formule IIIa' odnosno IIIb' u amino-skupinu,
kako bi se dobio spoj sljedeće formule IVa' odnosno IVb':
[image]
i
(iii) nitrozacija spoja formule IVa' odnosno IVb',
kako bi se dobio spoj formule Va odnosno Vb.
2. Postupak prema zahtjevu 1, naznačen time, da se spoj formule II' proizvodi tako, da postupak obuhvaća jedan ili drugi od sljedećih koraka:
(1-1) pripremanje spoja sljedeće formule I:
[image]
gdje Pg je amino-zaštitna skupina, i
(1-2) reakcija spoja formule I sa spojem sljedeće formule:
[image]
kako bi se dobio spoj formule II';
ili
(0-1') pripremanje spoja sljedeće formule Ia:
[image]
(0-2') reakcija spoja formule Ia sa spojem sljedeće formule:
[image]
kako bi se dobio spoj sljedeće formule IIa:
[image]
i
(0-3') uvođenje amino-zaštitne skupine Pg, kako bi se dobio spoj formule II'.
3. Postupak prema zahtjevu 1 ili 2, naznačen time, da se koraci od (i) do (iii), prema potrebi također i proizvodnja spoja formule II', provode u jednolončanom postupku.
4. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time, da se koraci (i) i (ii), prema potrebi također i koraci od (0-1) do (0-2) ili od (0-1') do (0-3'), provode pod bazičnim uvjetima u prisutnosti lužina, i/ili se korak (iii) provodi u kiselinskim uvjetima.
5. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time, da Z je vodik ili skupina koja se može pretvarati u hidroksietil, a nakon proizvodnje spoja formule Va, uvodi se hidroksietil-skupina, kako bi se dobio spoj sljedeće
formule Va':
[image]
6. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time, da se Pg odabire iz skupine koju čine amino-zaštitne skupine tipa oksikarbonila, amino-zaštitne skupine tipa karbamata i amino-zaštitne skupine tipa sulfonila, a poželjno je Pg odabran iz skupine koju čine: tert-butiloksikarbonil (Boc), karbobenziloksi (Cbz), metansulfonil (Ms), benzensulfonil (Bs), p-toluensulfonil (Ts) i 2-naftalensulfonil.
7. Postupak za proizvodnju spoja sljedeće formule VIII ili njegove soli:
[image]
naznačen time, da obuhvaća sljedeće korake:
(i) proizvodnja spoja sljedeće formule Va, Va' ili Vb, prema bilo kojem od zahtjeva
1 do 6:
[image]
[image]
pri čemu su Pg i Z prethodno definirani, no ako je Z vodik u spoju formule Va, ili je skupina koja se može pretvarati u hidroksietil, tada se uvodi hidroksietil-skupina, kako bi se dobio spoj formule Va',
(ii) izvođenje reakcije ili reakcija deprotekcije za odstranjivanje Pg, odnosno
izvođenje reakcije ili reakcija deprotekcije od vicinalne hidroksil-zaštitne skupine na pentan-prstenu u spoju formule Va odnosno Va',
(iii) prema potrebi tvorba soli od spoja formule VIII.
8. Postupak za proizvodnju farmaceutskog sastava koji sadrži spoj sljedeće formule VIII ili njegovu sol:
[image]
naznačen time, da obuhvaća sljedeće korake:
(i) proizvodnja spoja formule VIII ili njegove soli prema zahtjevu 7, i
(ii) miješanje spoja formule VIII ili njegove soli, s farmaceutski prihvatljivim nosačem i/ili s pomoćnim sredstvom.
9. Spoj, naznačen time, da ima sljedeću formulu VII:
[image]
10. Spoj, naznačen time, da ima sljedeću formulu II:
[image]
gdje Pg je amino-zaštitna skupina odabrana iz skupine koju čine amino-zaštitne skupine tipa oksikarbonila i amino-zaštitne skupine tipa sulfonila, a poželjno je Pg odabran iz skupine koju čine: tert-butiloksikarbonil (Boc), karbobenziloksi (Cbz), metansulfonil (Ms), benzensulfonil (Bs), p-toluensulfonil (Ts) i
2-naftalensulfonil, te Y je NO2 ili NH2.
11. Spoj, naznačen time, da ima sljedeću formulu IVa ili IVb:
[image]
gdje Pg je amino-zaštitna skupina odabrana iz skupine koju čine amino-zaštitne skupine tipa oksikarbonila i amino-zaštitne skupine tipa sulfonila, a poželjno je Pg odabran iz skupine koju čine: tert-butiloksikarbonil (Boc), karbobenziloksi
(Cbz), metansulfonil (Ms), benzensulfonil (Bs), p-toluensulfonil (Ts) i
2-naftalensulfonil, dok Y je NO2 ili NH2, a Z je vodik, hidroksietil ili skupina koja se može pretvarati u hidrioksietil.
12. Spoj, naznačen time, da ima sljedeću formulu Va ili Vb:
[image]
gdje Pg je amino-zaštitna skupina odabrana iz skupine koju čine amino-zaštitne skupine tipa oksikarbonila i amino-zaštitne skupine tipa sulfonila, a poželjno je Pg odabran iz skupine koju čine: tert-butiloksikarbonil (Boc), karbobenziloksi (Cbz), metansulfonil (Ms), benzensulfonil (Bs), p-toluensulfonil (Ts) i 2-naftalensulfonil, a Z je vodik, hidroksietil ili skupina koja se može pretvarati u hidrioksietil.
13. Spoj prema bilo kojem od zahtjeva 11 do 12, naznačen time, da Z je odabran od vodika, hidroksietila i -CH2-CO-OCH3.
14. Uporaba spoja prema bilo kojem od zahtjeva 9 do 13, naznačena time, da je za proizvodnju ticagrelora.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11181280A EP2570405A1 (en) | 2011-09-14 | 2011-09-14 | Synthesis of Triazolopyrimidine Compounds |
| EP11188602 | 2011-11-10 | ||
| EP11195581 | 2011-12-23 | ||
| PCT/EP2012/068068 WO2013037942A1 (en) | 2011-09-14 | 2012-09-14 | Synthesis of triazolopyrimidine compounds |
| EP12759136.0A EP2755957B2 (en) | 2011-09-14 | 2012-09-14 | Synthesis of triazolopyrimidine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20170167T1 true HRP20170167T1 (hr) | 2017-08-25 |
Family
ID=46851502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20170167TT HRP20170167T1 (hr) | 2011-09-14 | 2017-02-01 | Sinteza spojeva triazolopirimidina |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9221829B2 (hr) |
| EP (1) | EP2755957B2 (hr) |
| CN (1) | CN104024229B (hr) |
| CA (1) | CA2848621C (hr) |
| ES (1) | ES2620970T3 (hr) |
| HR (1) | HRP20170167T1 (hr) |
| HU (1) | HUE031673T2 (hr) |
| PL (1) | PL2755957T4 (hr) |
| WO (1) | WO2013037942A1 (hr) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN2014KN01491A (hr) * | 2011-12-23 | 2015-10-23 | Lek Pharmaceuticals | |
| US9233966B2 (en) | 2012-04-05 | 2016-01-12 | Dr. Reddy's Laboratories Limited | Preparation of ticagrelor |
| ITMI20130487A1 (it) * | 2013-03-29 | 2014-09-30 | Chemo Res S L | Alchilazione selettiva di ciclopentilalcoli |
| CN103304545B (zh) * | 2013-06-26 | 2015-05-20 | 苏州明锐医药科技有限公司 | 5-氨基-1,4-二取代基-1,2,3-三氮唑及其制备方法 |
| WO2014206187A1 (zh) | 2013-06-24 | 2014-12-31 | 苏州明锐医药科技有限公司 | 替卡格雷及其中间体的制备方法 |
| CN103539773B (zh) * | 2013-09-25 | 2015-04-08 | 开原亨泰制药股份有限公司 | 一种制备替格瑞洛关键中间体的方法 |
| CN103524429B (zh) * | 2013-09-28 | 2015-08-19 | 银杏树药业(苏州)有限公司 | 一种替格瑞洛及其新的中间体的制备方法 |
| CN104710425B (zh) * | 2013-12-16 | 2019-06-14 | 石药集团中奇制药技术（石家庄）有限公司 | 一种替格瑞洛新结晶及其制备方法 |
| CN103787987B (zh) * | 2014-02-17 | 2015-04-08 | 苏州明锐医药科技有限公司 | 替格瑞洛中间体的制备方法 |
| US10011605B2 (en) | 2014-06-18 | 2018-07-03 | Flamma Spa | Process for the preparation of triazolo[4,5-D] pyrimidine cyclopentane compounds |
| CN105503876B (zh) * | 2014-09-24 | 2017-09-05 | 海门慧聚药业有限公司 | 替卡格雷的制备方法 |
| CN107382953A (zh) * | 2017-07-25 | 2017-11-24 | 安徽诺全药业有限公司 | 一种制备多取代环戊烷衍生物的方法 |
| WO2019169111A1 (en) | 2018-03-02 | 2019-09-06 | The Trustees Of The University Of Pennsylvania | [1,2,4]triazolo[1,5-a]pyrimidine compounds and use in stabilizing microtubules |
| CN113214210B (zh) * | 2021-05-10 | 2022-03-04 | 合肥立方制药股份有限公司 | 一种二氢槲皮素的制备方法 |
| CN113185485B (zh) | 2021-05-10 | 2022-03-04 | 合肥立方制药股份有限公司 | 一种二氢槲皮素的半合成方法 |
| CN113582947B (zh) * | 2021-09-07 | 2023-06-20 | 南开大学 | 一种脱除胺的磺酰基保护的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI229674B (en) | 1998-12-04 | 2005-03-21 | Astra Pharma Prod | Novel triazolo[4,5-d]pyrimidine compounds, pharmaceutical composition containing the same, their process for preparation and uses |
| SE9903290D0 (sv) | 1999-09-15 | 1999-09-15 | Astra Pharma Prod | Novel compounds |
| SE9904129D0 (sv) | 1999-11-15 | 1999-11-15 | Astra Pharma Prod | Novel compounds |
| GB0013488D0 (en) | 2000-06-02 | 2000-07-26 | Astrazeneca Ab | Chemical compound |
| SI2340252T1 (sl) | 2008-09-09 | 2016-02-29 | Astrazeneca Ab | Postopek priprave (1S-)1-alfa, 2-alfa, 3-beta(1S*,2R*)5-beta))-3-(7-(2-(3,4-difluorofenil)-ciklopropilamino)-5- (propiltio)-3H-1,2,3-triazolo(4,5-D)pirimidin-3-il)-5-(2-hidroksietoksi) ciklopentan-1,2-diola in njegovih vmesnih spojin |
| WO2011017108A2 (en) | 2009-07-27 | 2011-02-10 | Auspex Pharmaceuticals, Inc. | Cyclopropyl modulators of p2y12 receptor |
| CA2859743A1 (en) * | 2010-12-20 | 2012-06-28 | Actavis Group Ptc Ehf | Novel processes for preparing triazolo[4,5-d]pyrimidine derivatives and intermediates thereof |
-
2012
- 2012-09-14 PL PL12759136T patent/PL2755957T4/pl unknown
- 2012-09-14 WO PCT/EP2012/068068 patent/WO2013037942A1/en active Application Filing
- 2012-09-14 CA CA2848621A patent/CA2848621C/en not_active Expired - Fee Related
- 2012-09-14 HU HUE12759136A patent/HUE031673T2/en unknown
- 2012-09-14 US US14/344,960 patent/US9221829B2/en not_active Expired - Fee Related
- 2012-09-14 ES ES12759136.0T patent/ES2620970T3/es active Active
- 2012-09-14 EP EP12759136.0A patent/EP2755957B2/en active Active
- 2012-09-14 CN CN201280052377.0A patent/CN104024229B/zh active Active
-
2017
- 2017-02-01 HR HRP20170167TT patent/HRP20170167T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL2755957T4 (pl) | 2017-05-31 |
| PL2755957T3 (pl) | 2017-04-28 |
| ES2620970T3 (es) | 2017-06-30 |
| EP2755957B2 (en) | 2019-05-15 |
| CA2848621C (en) | 2019-10-01 |
| US20150005498A1 (en) | 2015-01-01 |
| WO2013037942A1 (en) | 2013-03-21 |
| EP2755957B1 (en) | 2016-11-02 |
| HUE031673T2 (en) | 2017-07-28 |
| CN104024229B (zh) | 2016-08-31 |
| US9221829B2 (en) | 2015-12-29 |
| CN104024229A (zh) | 2014-09-03 |
| CA2848621A1 (en) | 2013-03-21 |
| EP2755957A1 (en) | 2014-07-23 |
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