HRP20171981T1 - Derivati pirazolkarboksamida kao taar modulatora za uporabu u liječenju nekoliko poremećaja poput depresije, dijabetesa i parkinsonove bolesti - Google Patents
Derivati pirazolkarboksamida kao taar modulatora za uporabu u liječenju nekoliko poremećaja poput depresije, dijabetesa i parkinsonove bolesti Download PDFInfo
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- HRP20171981T1 HRP20171981T1 HRP20171981TT HRP20171981T HRP20171981T1 HR P20171981 T1 HRP20171981 T1 HR P20171981T1 HR P20171981T T HRP20171981T T HR P20171981TT HR P20171981 T HRP20171981 T HR P20171981T HR P20171981 T1 HRP20171981 T1 HR P20171981T1
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Claims (19)
1. Spoj, naznačen time, da ima sljedeću formulu:
[image]
u kojoj
R1 je fenil, po potrebi supstituiran halogenom, C1-7-alkil, C3-6-cikloalkil, C1-7-alkoksi, cijano, C1-7-alkil supstituiran halogenom, C1-7-alkil supstituiran hidroksi skupinom, C1-7-alkoksi supstituiran halogenom ili C1-7-alkoksi supstuiran hidroksi skupinom; ili je piridin-2, -3 ili -4-il-skupina, po potrebi supstituirana halogenom, C1-7-alkil, C3-6-cikloalkil, cijano, C1-7-alkil supstituiran halogenom, C1-7-alkil supstituiran hidroksilom, C1-7-alkoksi,
C1-7-alkoksi supstituiran halogenom ili C1-7-alkoksi supstituiran hidroksilnom skupinom; ili je pirimidin-2, -4 ili -5-il-skupina, po potrebi supstituirana halogenom, C1-7-alkil, C3-6-cikloalkil, C1-7-alkil supstituiran hidroksi skupinom ili C1-7-alkil supstituiran halogenom; ili je pirazin-2-il-skupina, po potrebi supstituirana halogenom, C1-7-alkil, C3-6-cikloalkil, C1-7-alkil supstituiran halogenom, C1-7-alkil supstituiran hidroksi ili cijano skupinom; ili je
2,2-difluorobenzo[d][l,3]dioksol-5-il ili tiazolil po potrebi supstituiran s
C1-7-alkilom koji je supstituiran halogenom;
R2 je vodik ili C1-7-alkil;
R3 je vodik, amino ili C1-7-alkil;
Z je veza, -CH2- ili -O-;
ili njegova farmaceutski prihvatljiva kiselinska adicijska sol.
2. Spoj formule IA prema patentnom zahtjevu 1, naznačen time, da je to:
[image]
gdje
R2 je vodik ili C1-7-alkil;
R3 je vodik, amino ili C1-7-alkil;
R4 je vodik, halogen, C1-7-alkil, C3-6-cikloalkil, C1-7-alkoksi, cijano,
C1-7-alkil supstituiran halogenom, C1-7-alkil supstituiran hidroksilom,
C1-7-alkoksi supstituiran halogenom ili C1-7-alkoksi supstituiran hidroksi skupinom;
n je 1 ili 2;
Z je veza, -CH2- ili -O-;
ili njegova farmaceutski prihvatljiva kiselinska adicijska sol.
3. Spoj prema bilo kojem od zahtjeva 1 ili 2, naznačen time, da su spojevi sljedeći:
(S)-5-metil-N-(4-(morfolin-2-il)fenil)-1-fenil-1H-pirazol-4-karboksamid;
(S)-5-amino-1-(4-fluorofenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(4-metoksifenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(4-fluorofenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(3-fluorofenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(4-cijanofenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(R)-1-(4-fluorofenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(3-cijanofenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(4-bromo-2-cijanofenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(4-(difluorometoksi)fenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(3-(difluorometoksi)fenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(4-cijano-2-fluorofenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(4-cijano-3-fluorofenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(2-cijano-4-fluorofenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-N-(4-(morfolin-2-il)fenil)-1-(4-(trifluorometoksi)fenil)-1H-pirazol-4-karboksamid;
(R)-1-(4-(difluorometoksi)fenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(4-(difluorometoksi)fenil)-5-metil-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(4-(difluorometoksi)fenil)-3-metil-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(4-cijanofenil)-5-metil-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(R)-1-(4-cijano-2-fluorofenil)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(RS)-1-(4-difluorometoksi-fenil)-1H-pirazol-4-karboksilna kiselina-
(4-pirolidin-3-il-fenil)-amid; ili
(RS)-1-(4-difluorometoksi-fenil)-1H-pirazol-4-karboksilna kiselina-
(4-piperidin-3-il-fenil)-amid.
4. Spoj formule IB prema patentnom zahtjevu 1, naznačen time, da je to:
[image]
gdje
[image]
je piridin-2, -3 ili -4-il-skupina;
R2 je vodik ili C1-7-alkil;
R3 je vodik, amino ili C1-7-alkil;
R5 je vodik, halogen, C1-7-alkil, C3-6-cikloalkil, cijano, C1-7-alkil supstituiran halogenom, C1-7-alkil supstituiran hidroksi skupinom,
C1-7-alkoksi, C1-7-alkoksi supstituiran halogenom ili C1-7-alkoksi supstituiran hidroksi skupinom;
n je 1 ili 2;
Z je veza, -CH2- ili -O-;
ili njegova farmaceutski prihvatljiva kiselinska adicijska sol.
5. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time, da su spojevi sljedeći:
(S)-1-(5-kloropiridin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(5-cijanopiridin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(5-bromopiridin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(5-jodopiridin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-N-(4-morfolin-2-il)fenil)-1-(5-(trifluorometil)-piridin-2-Il)-1H-pirazol-4-karboksamid;
(S)-N-(4-morfolin-2-il)fenil)-1-(4-(trifluorometil)-piridin-2-Il)-1H-pirazol-4-karboksamid;
(S)-1-(4-kloropiridin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(2-bromopiridin-4-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(6-metoksipiridin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(3-fluoro-5-(trifluorometil)piridin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(2-kloropiridin-4-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(6-etoksipiridin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-N-(4-(morfolin-2-il)fenil)-1-(2-(trifluorometil)piridin-4-il)-1H-pirazol-4-karboksamid; ili
(S)-N-(4-(morfolin-2-il)fenil)-1-(6-(trifluorometil)piridin-3-il)-1H-pirazol-4-karboksamid.
6. Spoj s formulama IC1, IC2 i IC3 u skladu s patentnim zahtjevom 1,
naznačen time, da su to:
[image]
gdje
R2 je vodik ili C1-7-alkil;
R3 je vodik, amino ili C1-7-alkil;
R6 je vodik, halogen, C1-7-alkil, C3-6-cikloalkil, C1-7-alkil supstituiran halogenom ili C1-7- alkil supstituiran hidroksi skupinom;
Z je veza, -CH2- ili -O-;
ili njegova farmaceutski prihvatljiva kiselinska adicijska sol.
7. Spoj prema bilo kojem od zahtjeva 1 do 6, naznačen time, da su spojevi sljedeći:
(S)-1-(5-kloropirimidin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-N-(4-(morfolin-2-il)fenil)-1-(2-(trifluorometil)pirimidin-4-il)-1H-pirazol-4-karboksamid;
(S)-1-(2-kloropirimidin-4-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-N-(4-(morfon-2-il)fenil)-1-(5-(trifluorometil)pirimidin-2-il)-1H-pirazol-4-karboksamid;
(S)-1-(4-metilpirimidin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-N-(4-(morfolin-2-il)fenil)-1-(6-(trifluorometil)pirimidin-4-il)-1H-pirazol-4-karboksamid;
(S)-N-(4-(morfon-2-il)fenil)-1-(2-(trifluorometil)pirimidin-5-il)-1H-pirazol-4-karboksamid;
(S)-N-(4-(morfolin-2-il)fenil)-1-(4-(trifluorometil)pirimidin-2-il)-1H-pirazol-4-karboksamid; ili
(S)-1-(6-ciklopropilpirimidin-4-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid.
8. Spoj formule ID prema patentnom zahtjevu 1, naznačen time, da je to:
[image]
gdje
R2 je vodik ili C1-7-alkil;
R3 je vodik, amino ili C1-7-alkil;
R7 je vodik, halogen, C1-7-alkil, C3-6-cikloalkil, C1-7-alkil supstituiran halogenom, C1-7-alkil supstituiran hidroksilnom ili cijano skupinom;
Z je veza, -CH2- ili -O-;
ili njegova farmaceutski prihvatljiva kiselinska adicijska sol.
9. Spoj prema bilo kojem od zahtjeva 1 do 8, naznačen time, da su spojevi sljedeći:
(S)-N-(4-(morfolin-2-il)fenil)-1-(6-(trifluorometil)pirazin-2-il)-1H-pirazol-4-karboksamid;
(S)-1-(6-metilpirazin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(5-metilpirazin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(3-kloropirazin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(5-cijanopirazin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(5-kloropirazin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(6-cijanopirazin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid;
(S)-1-(3-cijanopirazin-2-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid; ili
(S)-N-(4-(morfolin-2-il)fenil)-1-(5-(trifluorometil)pirimidin-2-il)-1H-pirazol-4-karboksamid.
10. Spoj formule IE prema patentnom zahtjevu 1, naznačen time, da je to:
[image]
gdje
R2 je vodik ili C1-7-alkil;
R3 je vodik, amino ili C1-7-alkil;
Z je veza, -CH2- ili -O-;
ili njegova farmaceutski prihvatljiva kiselinska adicijska sol.
11. Spoj prema bilo kojem od zahtjeva 1 ili 10, naznačen time, da spoj je (S)-1-(2,2-dihiorobenzo[d][1,3]dioksol-5-il)-N-(4-(morfolin-2-il)fenil)-1H-pirazol-4-karboksamid.
12. Spoj formule IF prema patentnom zahtjevu 1, naznačen time, da je to:
[image]
gdje
R2 je vodik ili C1-7-alkil;
R3 je vodik, amino ili C1-7-alkil;
Z je veza, -CH2- ili -O-;
ili njegova farmaceutski prihvatljiva kiselinska adicijska sol.
13. Spoj prema bilo kojem od zahtjeva 1 ili 12, naznačen time, da spoj je (S)-N-(4-(morfolin-2-il)fenil)-1-(4-(trifluorometil)tiazol-2-il)-1H-pirazol-4-karboksamid.
14. Postupak proizvodnje spoja formule I u skladu s bilo kojim od zahtjeva 1 do 13, naznačen time, da postupak obuhvaća
cijepanje zaštitne skupine spojeva formule:
[image]
da bi se stvorio spoj formule I:
[image]
i ako je potrebno,
pretvaranje dobivenih spojeva u farmaceutski prihvatljive kiselinske adicijske soli, pri čemu su supstituenti takvi kao što su opisani u zahtjevu 1.
15. Farmaceutski sastav, naznačen time, da obuhvaća spoj prema bilo kojem od patentnih zahtjeva 1 do 13, zajedno s farmaceutski prihvatljivim nosačem i/ili pomoćnom tvari.
16. Farmaceutski sastav u skladu s patentnim zahtjevom 15, naznačen time, da obuhvaća spoj prema bilo kojem od patentnih zahtjeva 1 do 13, zajedno s farmaceutski prihvatljivim nosačem i/ili pomoćnom tvari, za uporabu u liječenju depresije, poremećaja anksioznosti, bipolarnog poremećaja, hiperaktivnog poremećaja s manjkom pozornosti (ADHD), poremećaja uzrokovanih stresom, psihotičnih poremećaja, shizofrenije, neuroloških bolesti, Parkinsonove bolesti, neurodegenerativnih poremećaja, Alzheimerove bolesti, epilepsije, migrene, hipertenzije, zlouporabe droga, metaboličkih poremećaja, poremećaja hranjenja, dijabetesa, dijabetičkih komplikacija, pretilosti, dislipidemije, poremećaja potrošnje energije i asimilacije, poremećaja i nepravilnosti kod homeostaze tjelesne temperature, poremećaja spavanja i cirkadijalnog ritma, te kardiovaskularnih poremećaja.
17. Spojevi prema bilo kojem od patentnih zahtjeva 1 do 13, naznačeni time, da se upotrebljavaju kao terapeutski djelotvorne tvari.
18. Spojevi prema bilo kojem od patentnih zahtjeva 1 do 13, naznačeni time, da se upotrebljavaju u liječenju depresije, poremećaja anksioznosti, bipolarnog poremećaja, hiperaktivnog poremećaja s manjkom pozornosti (ADHD), poremećaja uzrokovanih stresom, psihotičnih poremećaja, shizofrenije, neuroloških bolesti, Parkinsonove bolesti, neurodegenerativnih poremećaja, Alzheimerove bolesti, epilepsije, migrene, hipertenzije, zlouporabe droga, metaboličkih poremećaja, poremećaja hranjenja, dijabetesa, dijabetičkih komplikacija, pretilosti, dislipidemije, poremećaja potrošnje energije i asimilacije, poremećaja i nepravilnosti kod homeostaze tjelesne temperature, poremećaja spavanja i cirkadijalnog ritma, te kardiovaskularnih poremećaja.
19. Uporaba spoja prema bilo kojem od patentnih zahtjeva 1 do 13, naznačena time, da je za proizvodnju lijekova za terapeutsko i/ili profilaktičko liječenje depresije, poremećaja anksioznosti, bipolarnog poremećaja, hiperaktivnog poremećaja s manjkom pozornosti (ADHD), poremećaja uzrokovanih stresom, psihotičnih poremećaja, shizofrenije, neuroloških bolesti, Parkinsonove bolesti, neurodegenerativnih poremećaja, Alzheimerove bolesti, epilepsije, migrene, hipertenzije, zlouporabe droga, metaboličkih poremećaja, poremećaja hranjenja, dijabetesa, dijabetičkih komplikacija, pretilosti, dislipidemije, poremećaja potrošnje energije i asimilacije, poremećaja i nepravilnosti kod homeostaze tjelesne temperature, poremećaja spavanja i cirkadijalnog ritma, te kardiovaskularnih poremećaja.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12184360 | 2012-09-14 | ||
| PCT/EP2013/068769 WO2014041007A1 (en) | 2012-09-14 | 2013-09-11 | Pyrazole carboxamide derivatives as taar modulators for use in the treatment of several disorders, such as depression, diabetes and parkinson's disease |
| EP13759754.8A EP2895477B1 (en) | 2012-09-14 | 2013-09-11 | Pyrazole carboxamide derivatives as taar modulators for use in the treatment of several disorders, such as depression, diabetes and parkinson's disease. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20171981T1 true HRP20171981T1 (hr) | 2018-02-09 |
Family
ID=47044779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20171981TT HRP20171981T1 (hr) | 2012-09-14 | 2013-09-11 | Derivati pirazolkarboksamida kao taar modulatora za uporabu u liječenju nekoliko poremećaja poput depresije, dijabetesa i parkinsonove bolesti |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US9487501B2 (hr) |
| EP (1) | EP2895477B1 (hr) |
| JP (2) | JP2015531782A (hr) |
| KR (1) | KR101706486B1 (hr) |
| CN (2) | CN107903251A (hr) |
| AR (1) | AR092537A1 (hr) |
| AU (1) | AU2013314388B2 (hr) |
| BR (1) | BR112015004511B1 (hr) |
| CA (1) | CA2882821C (hr) |
| CL (1) | CL2015000580A1 (hr) |
| CR (1) | CR20150087A (hr) |
| DK (1) | DK2895477T3 (hr) |
| EA (1) | EA026062B1 (hr) |
| ES (1) | ES2654653T3 (hr) |
| HK (2) | HK1206720A1 (hr) |
| HR (1) | HRP20171981T1 (hr) |
| HU (1) | HUE037689T2 (hr) |
| IL (1) | IL237332B (hr) |
| LT (1) | LT2895477T (hr) |
| MA (1) | MA37944B2 (hr) |
| MX (1) | MX363362B (hr) |
| MY (1) | MY178667A (hr) |
| NO (1) | NO2895477T3 (hr) |
| NZ (1) | NZ705154A (hr) |
| PE (1) | PE20150735A1 (hr) |
| PH (1) | PH12015500489A1 (hr) |
| PL (1) | PL2895477T3 (hr) |
| PT (1) | PT2895477T (hr) |
| RS (1) | RS56747B1 (hr) |
| SG (1) | SG11201501958QA (hr) |
| SI (1) | SI2895477T1 (hr) |
| TW (1) | TWI610926B (hr) |
| UA (1) | UA113776C2 (hr) |
| WO (1) | WO2014041007A1 (hr) |
| ZA (1) | ZA201501126B (hr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2016016162A1 (en) * | 2014-07-30 | 2016-02-04 | F. Hoffmann-La Roche Ag | 6-amino-5,6,7,8-tetrahydronaphthalen-2-yl or 3-aminochroman-7-yl derivatives as taar modulators |
| MY195528A (en) * | 2016-03-17 | 2023-01-30 | Hoffmann La Roche | 5-Ethyl-4-Methyl-Pyrazole-3-Carboxamide Derivative Having Activity as Agonist of Taar |
| EP3555077B1 (en) | 2016-12-15 | 2023-04-19 | The Regents of The University of California | Compositions and methods for treating cancer |
| US20220340597A1 (en) | 2019-04-09 | 2022-10-27 | Hoffmann-La Roche Inc. | Hexahydro-1h-pyrazino[1,2-a]pyrazine compounds for the treatment of autoimmune disease |
| CN117120427A (zh) * | 2021-06-18 | 2023-11-24 | 上海拓界生物医药科技有限公司 | 一种malt1抑制剂及其制备方法和用途 |
| CN116236478A (zh) * | 2022-12-27 | 2023-06-09 | 浙江大学 | 芳香杂环甲酰胺类化合物的应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9425211D0 (en) | 1994-12-14 | 1995-02-15 | Ucb Sa | Substituted 1H-imidazoles |
| GB9520150D0 (en) | 1995-10-03 | 1995-12-06 | Orion Yhtymae Oy | New imidazole derivatives |
| US6841684B2 (en) | 1997-12-04 | 2005-01-11 | Allergan, Inc. | Imidiazoles having reduced side effects |
| MX2009008465A (es) | 2007-02-15 | 2009-08-20 | Hoffmann La Roche | Nuevas 2-aminooxazolinas como ligandos de taar1. |
| US9452980B2 (en) * | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
| TW201236685A (en) * | 2010-11-11 | 2012-09-16 | Daiichi Sankyo Co Ltd | New pyrazole amide derivatives |
| US9073911B2 (en) * | 2011-06-09 | 2015-07-07 | Hoffmann-La Roche Inc. | Pyrazole derivatives |
| US9029370B2 (en) * | 2011-06-10 | 2015-05-12 | Hoffmann-La Roche Inc. | Substituted benzamide derivatives |
-
2013
- 2013-09-11 EA EA201590454A patent/EA026062B1/ru not_active IP Right Cessation
- 2013-09-11 AU AU2013314388A patent/AU2013314388B2/en not_active Ceased
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- 2013-09-11 PT PT137597548T patent/PT2895477T/pt unknown
- 2013-09-11 CN CN201711272710.XA patent/CN107903251A/zh active Pending
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- 2013-09-11 PE PE2015000364A patent/PE20150735A1/es active IP Right Grant
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- 2013-09-11 CN CN201380047584.1A patent/CN104619700A/zh active Pending
- 2013-09-11 MX MX2015002900A patent/MX363362B/es unknown
- 2013-09-11 SI SI201330900T patent/SI2895477T1/en unknown
- 2013-09-11 NO NO13759754A patent/NO2895477T3/no unknown
- 2013-09-11 HK HK15107153.1A patent/HK1206720A1/xx unknown
- 2013-09-11 PL PL13759754T patent/PL2895477T3/pl unknown
- 2013-09-11 MA MA37944A patent/MA37944B2/fr unknown
- 2013-09-11 LT LTEP13759754.8T patent/LT2895477T/lt unknown
- 2013-09-11 WO PCT/EP2013/068769 patent/WO2014041007A1/en not_active Ceased
- 2013-09-11 DK DK13759754.8T patent/DK2895477T3/en active
- 2013-09-11 BR BR112015004511-1A patent/BR112015004511B1/pt not_active IP Right Cessation
- 2013-09-11 SG SG11201501958QA patent/SG11201501958QA/en unknown
- 2013-09-11 EP EP13759754.8A patent/EP2895477B1/en active Active
- 2013-09-11 ES ES13759754.8T patent/ES2654653T3/es active Active
- 2013-09-11 JP JP2015531543A patent/JP2015531782A/ja active Pending
- 2013-09-11 KR KR1020157009118A patent/KR101706486B1/ko not_active Expired - Fee Related
- 2013-09-11 NZ NZ705154A patent/NZ705154A/en not_active IP Right Cessation
- 2013-09-12 AR ARP130103258A patent/AR092537A1/es not_active Application Discontinuation
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2015
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