HRP20180948T1 - Postupak za proizvodnju aminokiselinskih spojeva - Google Patents
Postupak za proizvodnju aminokiselinskih spojeva Download PDFInfo
- Publication number
- HRP20180948T1 HRP20180948T1 HRP20180948TT HRP20180948T HRP20180948T1 HR P20180948 T1 HRP20180948 T1 HR P20180948T1 HR P20180948T T HRP20180948T T HR P20180948TT HR P20180948 T HRP20180948 T HR P20180948T HR P20180948 T1 HRP20180948 T1 HR P20180948T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- salt
- formula
- hydrogen
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 17
- -1 amino acid compounds Chemical class 0.000 title claims 8
- 150000003839 salts Chemical class 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 230000015572 biosynthetic process Effects 0.000 claims 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 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 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/30—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Peptides Or Proteins (AREA)
Claims (21)
1. Postupak, naznačen time, da obuhvaća redukciju spoja formule II, ili njegove soli:
gdje:
R1 i R2 su neovisno vodik, C1-C12 alkil ili amino-zaštitna skupina,
za tvorbu spoja formule I:
ili njegove soli.
2. Postupak prema zahtjevu 1, naznačen time, da nadalje obuhvaća hidrolizaciju spoja formule III, ili njegove soli:
gdje:
R3 je prema potrebi supstituirani C1-C12 alkil,
za tvorbu spoja formule II, ili njegove soli.
3. Postupak prema zahtjevu 2, naznačen time, da nadalje obuhvaća reakciju spoja formule IV, ili njegove soli ili njegovog tautomera:
s NHR1R2, ili s njegovom soli,
za tvorbu spoja formule III, ili njegove soli.
4. Postupak prema zahtjevu 3, naznačen time, da navedeni spoj NHR1R2 je NH2(izopropil).
5. Postupak prema zahtjevu 3, naznačen time, da nadalje obuhvaća dovođenje u doticaj spoja formule V, ili njegove soli:
s HCO2R4, gdje R4 je prema potrebi supstituirani C1-C12 alkil, ili njegova sol,
pod bazičnim uvjetima, za tvorbu spoja formule IV, ili njegove soli.
6. Postupak prema zahtjevu 5, naznačen time, da navedeni bazični uvjeti obuhvaćaju lužinu odabranu od hidroksidne baze ili alkoksidne baze.
7. Postupak prema bilo kojem od zahtjeva 1 do 6, naznačen time, da R1 je amino-zaštitna skupina.
8. Postupak prema bilo kojem od zahtjeva 1 do 7, naznačen time, da je navedena amino-zaštitna skupina odabrana od sljedećih: acetil, trifluoroacetil, ftalimid, benzil, trifenilmetil, benzilidenil, p-toluensulfonil, p-metoksibenzil, tert-butiloksikarbonil, 9-fluorenilmetiloksikarbonil i karbobenziloksi.
9. Postupak prema bilo kojem od zahtjeva 1 do 8, naznačen time, da R1 je tert-butiloksikarbonil i R2 je izopropil.
10. Postupak prema bilo kojem od zahtjeva 1 do 9, naznačen time, da navedena redukcija obuhvaća dovođenje u doticaj spoja formule II, ili njegove soli, s metalnim katalizatorom i vodikovim plinom.
11. Postupak prema zahtjevu 10, naznačen time, da navedeni metalni katalizator je rutenijev, rodijev ili paladijev katalizator.
12. Postupak prema zahtjevu 10 ili zahtjevu 11, naznačen time, da navedeni metalni katalizator je [(S)-BINAPRuCl(benzen)]Cl.
13. Postupak prema bilo kojem od zahtjeva 1 do 12, naznačen time, da R2 je amino-zaštitna skupina.
14. Postupak prema bilo kojem od zahtjeva 1 do 13, naznačen time, da R2 je C1-C12 alkil.
15. Postupak prema bilo kojem od zahtjeva 1 do 14, naznačen time, da R2 je izopropil.
16. Postupak prema bilo kojem od zahtjeva 1 do 15, naznačen time, da navedena redukcija obuhvaća redukciju spoja formule IIb, ili njegove soli:
za tvorbu spoja formule I, ili njegove soli.
17. Spoj, naznačen time, da ima formulu VI:
ili njegova sol, pri čemu:
R1 je vodik ili t-butiloksikarbonil;
R2 je C1-C12 alkil; i
R5 je vodik ili C1-C12 alkil.
18. Spoj prema zahtjevu 17, naznačen time, da R1 je vodik; R2 je izopropil; i R5 je vodik ili etil.
19. Spoj prema zahtjevu 17, naznačen time, da ima formulu VIb:
ili njegova sol, gdje R1 je vodik ili t-butiloksikarbonil.
20. Spoj prema zahtjevu 17 ili zahtjevu 19, naznačen time, da R1 je
t-butiloksikarbonil.
21. Spoj, naznačen time, da ima formulu VIb:
ili njegova sol, gdje R1 je vodik ili jedna amino-zaštitna skupina.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261648534P | 2012-05-17 | 2012-05-17 | |
| EP13724711.0A EP2850054B1 (en) | 2012-05-17 | 2013-05-17 | Process for making amino acid compounds |
| PCT/US2013/041687 WO2013173779A1 (en) | 2012-05-17 | 2013-05-17 | Process for making amino acid compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20180948T1 true HRP20180948T1 (hr) | 2018-08-10 |
Family
ID=48483247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20180948TT HRP20180948T1 (hr) | 2012-05-17 | 2018-06-19 | Postupak za proizvodnju aminokiselinskih spojeva |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US9278917B2 (hr) |
| EP (1) | EP2850054B1 (hr) |
| JP (1) | JP6196294B2 (hr) |
| KR (1) | KR102074535B1 (hr) |
| CN (1) | CN104520263B (hr) |
| AU (1) | AU2013262516B2 (hr) |
| BR (1) | BR112014028585B1 (hr) |
| CA (1) | CA2873658C (hr) |
| ES (1) | ES2668477T3 (hr) |
| HK (1) | HK1208857A1 (hr) |
| HR (1) | HRP20180948T1 (hr) |
| IL (1) | IL235630A (hr) |
| MA (1) | MA37751B1 (hr) |
| MX (1) | MX350443B (hr) |
| MY (1) | MY171538A (hr) |
| NZ (1) | NZ702939A (hr) |
| PL (1) | PL2850054T3 (hr) |
| RU (1) | RU2643146C2 (hr) |
| SG (1) | SG11201407625WA (hr) |
| SI (1) | SI2850054T1 (hr) |
| TR (1) | TR201807444T4 (hr) |
| WO (1) | WO2013173779A1 (hr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LT2858989T (lt) | 2012-05-17 | 2020-08-10 | Genentech, Inc. | Akt inhibuojančio pirimidinil-ciklopentano junginio amorfinė forma, jo kompozicijos ir būdai |
| DK2861582T3 (en) | 2012-05-17 | 2016-08-22 | Array Biopharma Inc | A process for preparing hydroxylated compounds cyclopentylpyrimidin |
| ES2588878T3 (es) | 2012-05-17 | 2016-11-07 | Array Biopharma, Inc. | Proceso para preparar compuestos de ciclopentilpirimidina hidroxilada |
| KR102123131B1 (ko) | 2012-05-17 | 2020-06-15 | 제넨테크, 인크. | 하이드록실화 사이클로펜타피리미딘 화합물 및 이의 염의 제조 방법 |
| EP4282973A3 (en) | 2013-11-15 | 2024-03-27 | F. Hoffmann-La Roche AG | Processes for the preparation of pyrimidinylcyclopentane compounds |
| BR112017005931B1 (pt) * | 2014-09-26 | 2024-04-30 | F. Hoffmann-La Roche Ag | Processos para preparar um composto de ciclopentil[d]pirimidin-4-il) piperazina e composto de ciclopentil[d]pirimidin-4-il)piperazina |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4663327A (en) * | 1984-05-23 | 1987-05-05 | Bayer Aktiengesellschaft | 1-heteroaryl-4-aryl-pyrazolin-5-ones |
| WO1995015684A1 (en) | 1993-12-12 | 1995-06-15 | Agrogene, Ltd. | A novel method to protect plants from fungal infection |
| AU724216B2 (en) | 1997-04-07 | 2000-09-14 | Merck & Co., Inc. | A method of treating cancer |
| US6201023B1 (en) | 1997-06-10 | 2001-03-13 | Agrogene Ltd. | Methods and compositions to protect crops against plant parasitic nematodes |
| EP0982300A3 (en) | 1998-07-29 | 2000-03-08 | Societe Civile Bioprojet | Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications |
| EP1158982A4 (en) | 1999-03-03 | 2002-06-12 | Merck & Co Inc | Prenyl protein transferase inhibitors |
| AU7715300A (en) | 1999-09-27 | 2001-04-30 | Merck & Co., Inc. | Method of preventing osteoporosis |
| PE20050630A1 (es) | 2003-06-09 | 2005-09-22 | Boehringer Ingelheim Int | Compuestos heterociclicos como inhibidores del papiloma virus |
| FR2892416B1 (fr) * | 2005-10-20 | 2008-06-27 | Sanofi Aventis Sa | Derives de 6-heteroarylpyridoindolone, leur preparation et leur application en therapeutique |
| US8927546B2 (en) | 2006-02-28 | 2015-01-06 | Dart Neuroscience (Cayman) Ltd. | Therapeutic piperazines |
| UA95641C2 (en) * | 2006-07-06 | 2011-08-25 | Эррей Биофарма Инк. | Hydroxylated cyclopenta [d] pyrimidines as akt protein kinase inhibitors |
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| EP2209775A1 (en) | 2007-10-09 | 2010-07-28 | UCB Pharma, S.A. | Heterobicyclic compounds as histamine h4-receptor antagonists |
| CN102459165B (zh) | 2009-04-15 | 2015-09-02 | Abbvie公司 | 抗病毒化合物 |
| EP2491032B1 (en) | 2009-10-23 | 2014-04-16 | Eli Lilly and Company | Akt inhibitors |
| EP2592933B1 (en) | 2010-07-16 | 2017-04-05 | Anderson Gaweco | Mif inhibitors and their uses |
| WO2012177925A1 (en) | 2011-06-21 | 2012-12-27 | The Board Institute, Inc. | Akt inhibitors for treating cancer expressing a magi3 - akt3 fusion gene |
| KR102123131B1 (ko) | 2012-05-17 | 2020-06-15 | 제넨테크, 인크. | 하이드록실화 사이클로펜타피리미딘 화합물 및 이의 염의 제조 방법 |
| ES2588878T3 (es) | 2012-05-17 | 2016-11-07 | Array Biopharma, Inc. | Proceso para preparar compuestos de ciclopentilpirimidina hidroxilada |
| CA2889855A1 (en) | 2012-11-01 | 2014-05-08 | Robert S. Katz | Methods for treating fibromyalgia |
| JP2016513112A (ja) | 2013-02-18 | 2016-05-12 | ザ スクリプス リサーチ インスティテュート | 治療的潜在能力を有するバソプレッシン受容体のモジュレーター |
| CA2904662A1 (en) | 2013-03-15 | 2014-09-25 | Shifa Biomedical Corporation | Anti-pcsk9 compounds and methods for the treatment and/or prevention of cardiovascular diseases |
-
2013
- 2013-05-17 ES ES13724711.0T patent/ES2668477T3/es active Active
- 2013-05-17 MA MA37751A patent/MA37751B1/fr unknown
- 2013-05-17 EP EP13724711.0A patent/EP2850054B1/en active Active
- 2013-05-17 TR TR2018/07444T patent/TR201807444T4/tr unknown
- 2013-05-17 KR KR1020147035263A patent/KR102074535B1/ko active IP Right Grant
- 2013-05-17 WO PCT/US2013/041687 patent/WO2013173779A1/en active Application Filing
- 2013-05-17 MX MX2014013863A patent/MX350443B/es active IP Right Grant
- 2013-05-17 CA CA2873658A patent/CA2873658C/en active Active
- 2013-05-17 US US14/401,095 patent/US9278917B2/en active Active
- 2013-05-17 SG SG11201407625WA patent/SG11201407625WA/en unknown
- 2013-05-17 NZ NZ702939A patent/NZ702939A/en unknown
- 2013-05-17 RU RU2014150991A patent/RU2643146C2/ru active
- 2013-05-17 BR BR112014028585-3A patent/BR112014028585B1/pt active IP Right Grant
- 2013-05-17 MY MYPI2014703417A patent/MY171538A/en unknown
- 2013-05-17 AU AU2013262516A patent/AU2013262516B2/en active Active
- 2013-05-17 PL PL13724711T patent/PL2850054T3/pl unknown
- 2013-05-17 JP JP2015512903A patent/JP6196294B2/ja active Active
- 2013-05-17 CN CN201380037572.0A patent/CN104520263B/zh active Active
- 2013-05-17 SI SI201331043T patent/SI2850054T1/en unknown
-
2014
- 2014-11-11 IL IL235630A patent/IL235630A/en active IP Right Grant
-
2015
- 2015-09-29 HK HK15109539.2A patent/HK1208857A1/xx unknown
-
2018
- 2018-06-19 HR HRP20180948TT patent/HRP20180948T1/hr unknown
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