HRP20160518T1 - Postupci za proizvodnju farmaceutske djelatne tvari - Google Patents
Postupci za proizvodnju farmaceutske djelatne tvari Download PDFInfo
- Publication number
- HRP20160518T1 HRP20160518T1 HRP20160518TT HRP20160518T HRP20160518T1 HR P20160518 T1 HRP20160518 T1 HR P20160518T1 HR P20160518T T HRP20160518T T HR P20160518TT HR P20160518 T HRP20160518 T HR P20160518T HR P20160518 T1 HRP20160518 T1 HR P20160518T1
- Authority
- HR
- Croatia
- Prior art keywords
- process according
- compound
- formula
- alcoholic solvent
- rani
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 15
- 239000013543 active substance Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 230000001476 alcoholic effect Effects 0.000 claims 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 238000005984 hydrogenation reaction Methods 0.000 claims 3
- 238000000746 purification Methods 0.000 claims 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229910052723 transition metal Inorganic materials 0.000 claims 2
- 150000003624 transition metals Chemical class 0.000 claims 2
- PLNHDPOPGAMJAW-UHFFFAOYSA-N 2-(6-fluoro-1h-indol-3-yl)acetonitrile Chemical compound FC1=CC=C2C(CC#N)=CNC2=C1 PLNHDPOPGAMJAW-UHFFFAOYSA-N 0.000 claims 1
- NXXGZNXPUZNCGV-UHFFFAOYSA-N 3-(2,2,3,3-tetrafluoropropoxy)benzaldehyde Chemical compound FC(F)C(F)(F)COC1=CC=CC(C=O)=C1 NXXGZNXPUZNCGV-UHFFFAOYSA-N 0.000 claims 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 claims 1
- 239000001358 L(+)-tartaric acid Substances 0.000 claims 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
Claims (14)
1. Postupak pripreme spoja formule IV,
[image]
koji obuhvaća korake:
(a) miješanje (6-fluoro-1H-indol-3-il)acetonitrila, NH3 u vodi i prijelaznog metalnog katalizatora u alkoholnom otapalu; i
(b) hidrogeniranje smjese s H2.
2. Postupak prema zahtjevu 1, gdje je prijelazni metalni katalizator RaNi.
3. Postupak prema zahtjevu 1, gdje je alkoholno otapalo metanol.
4. Postupak prema bilo kojem od zahtjeva 1-3, gdje se hidrogeniranje provodi pri tlaku od 250000 paskala (2.5 bara) kroz 16 sati.
5. Postupak prema bilo kojem od zahtjeva 1-4, gdje se hidrogeniranje provodi na temperaturi od 55°C do 65°C.
6. Postupak prema zahtjevu 2, gdje se RaNi koristi kao katalizator u obliku metalne spužve.
7. Postupak prema zahtjevu 2 ili 6, gdje je nominalni sastav aluminija u RaNi 5% i medijan veličine čestica RaNi je 33 mikrona.
8. Postupak prema bilo kojem od zahtjeva 1-7, gdje je NH3 prisutan u vodenoj otopini u koncentraciji od 25%.
9. Postupak prema bilo kojem od prethodnih zahtjeva, dalje obuhvaća pročišćavanje spoja formule IV, pročišćavanje obuhvaća:
(a) otapanje spoja formule IV u alkoholnom otapalu;
(b) dodavanje otopine L(+)-vinske kiseline; i
(c) hvatanje vinske kiseline u obliku taloga.
10. Postupak prema zahtjevu 9, gdje je alkoholno otapalo metanol.
11. Postupak prema zahtjevu 9 ili 10, gdje se etil acetat koristi s alkoholnim otapalom.
12. Postupak prema bilo kojem od prethodnih zahtjeva, dalje obuhvaća reakciju spoja Formule IV da se formira spoj formule I, spajanjem amina s 3-(2,2,3,3-tetrafluoropropoksi)benzaldehidom u prisutnosti otapala, nakon čega slijedi redukcija iminske veze pomoću reducensa
[image]
13. Postupak prema zahtjevu 12, gdje je reducens natrijev borohidrid.
14. Postupak prema zahtjevu 12 ili 13, dalje obuhvaća pretvorbu spoja formule I u njegovu HCl sol salt putem dodavanja HCl, nakon čega po izboru slijedi pročišćavanje dobivene soli.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28953009P | 2009-12-23 | 2009-12-23 | |
| PCT/DK2010/050348 WO2011076212A2 (en) | 2009-12-23 | 2010-12-20 | Processes for the manufacture of a pharmaceutically active agent |
| EP10803222.8A EP2516394B1 (en) | 2009-12-23 | 2010-12-20 | Processes for the manufacture of a pharmaceutically active agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20160518T1 true HRP20160518T1 (hr) | 2016-06-03 |
Family
ID=43567689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20160518TT HRP20160518T1 (hr) | 2009-12-23 | 2016-05-16 | Postupci za proizvodnju farmaceutske djelatne tvari |
Country Status (37)
| Country | Link |
|---|---|
| US (3) | US8461353B2 (hr) |
| EP (1) | EP2516394B1 (hr) |
| JP (2) | JP5864435B2 (hr) |
| KR (2) | KR101873182B1 (hr) |
| CN (2) | CN102656146B (hr) |
| AR (1) | AR079580A1 (hr) |
| AU (1) | AU2010335659B2 (hr) |
| BR (1) | BR112012015749A2 (hr) |
| CA (1) | CA2785440C (hr) |
| CL (1) | CL2012001725A1 (hr) |
| CR (1) | CR20120316A (hr) |
| CY (1) | CY1118032T1 (hr) |
| DK (1) | DK2516394T3 (hr) |
| DO (1) | DOP2012000170A (hr) |
| EA (1) | EA021440B1 (hr) |
| ES (1) | ES2575666T3 (hr) |
| GE (1) | GEP20146078B (hr) |
| HK (2) | HK1174921A1 (hr) |
| HR (1) | HRP20160518T1 (hr) |
| HU (1) | HUE028806T2 (hr) |
| IL (2) | IL220329A (hr) |
| MA (1) | MA33945B1 (hr) |
| ME (1) | ME02401B (hr) |
| MX (1) | MX2012007078A (hr) |
| MY (1) | MY159251A (hr) |
| NZ (2) | NZ600639A (hr) |
| PL (1) | PL2516394T3 (hr) |
| PT (1) | PT2516394E (hr) |
| RS (1) | RS54820B1 (hr) |
| SG (1) | SG181910A1 (hr) |
| SI (1) | SI2516394T1 (hr) |
| SM (1) | SMT201600166B (hr) |
| TN (1) | TN2012000279A1 (hr) |
| TW (1) | TW201139370A (hr) |
| UA (1) | UA111584C2 (hr) |
| WO (1) | WO2011076212A2 (hr) |
| ZA (1) | ZA201305936B (hr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201139370A (en) | 2009-12-23 | 2011-11-16 | Lundbeck & Co As H | Processes for the manufacture of a pharmaceutically active agent |
| JO3459B1 (ar) | 2012-09-09 | 2020-07-05 | H Lundbeck As | تركيبات صيدلانية لعلاج مرض الزهايمر |
| JO3639B1 (ar) * | 2014-07-04 | 2020-08-27 | H Lundbeck As | صورة متعددة الشكل جديدة لـ n-[2-(6-فلورو-1h-إندول-3-يل)إيثيل]-3-(2،2،3،3-تترا فلورو بروبوكسي)بنزيل أمين هيدروكلوريد |
| CN104130174A (zh) * | 2014-07-30 | 2014-11-05 | 天津市斯芬克司药物研发有限公司 | 一种吲唑衍生物及其制备方法 |
| CN105175307A (zh) * | 2014-11-18 | 2015-12-23 | 苏州晶云药物科技有限公司 | Lu AE58054的盐酸盐晶型A及其制备方法和用途 |
| TW201630881A (zh) | 2014-12-12 | 2016-09-01 | Ｈ 朗德貝克公司 | 用於生產艾達魯吡啶之方法 |
| CN104529865B (zh) * | 2014-12-12 | 2017-02-01 | 广东东阳光药业有限公司 | 苄胺类衍生物及其在药物上的应用 |
| MA41148A (fr) * | 2014-12-12 | 2017-10-17 | H Lundbeck As | Procédé de fabrication d'idalopirdine |
| CN108271369A (zh) * | 2015-10-23 | 2018-07-10 | 法尔玛赞公司 | 用于制备色胺及其衍生物的新工艺 |
| JP2019513742A (ja) | 2016-04-08 | 2019-05-30 | ハー・ルンドベック・アクチエゼルスカベット | イミンの水素化によるイダロピルジンの製造方法 |
| EP3333154A1 (en) * | 2016-12-07 | 2018-06-13 | Sandoz Ag | Crystalline form of a selective 5-ht6 receptor antagonist |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3042685A (en) | 1962-07-03 | Process of making g-fluoro tryptamine | ||
| GB846675A (en) | 1958-04-18 | 1960-08-31 | Lab Francais Chimiotherapie | Process for the production of a tryptamine derivative |
| US4803218A (en) * | 1982-09-29 | 1989-02-07 | Mcneilab, Inc. | 3-aminoalkyl-1H-indole-5-urea and amide derivatives |
| DE69416697T2 (de) | 1993-12-28 | 1999-09-09 | Rhone Poulenc Fibres | Verfahren zur katalytischer hydrogenierung von nitrilen zu aminen in anwesenheit eines dosierten raney nickel katalysators |
| EP0737101B1 (fr) | 1993-12-28 | 1998-09-23 | RHODIA FIBER & RESIN INTERMEDIATES | Procede de preparation d'un catalyseur d'hydrogenation de nitriles en amines et application de ce catalyseur en hydrogenation |
| US5869653A (en) | 1997-10-30 | 1999-02-09 | Air Products And Chemicals, Inc. | Hydrogenation of nitriles to produce amines |
| KR20000069831A (ko) | 1997-10-31 | 2000-11-25 | 요트.게.아. 롤페즈 | 구성 신호에 대한 잡음 추가를 통한 엘피씨 원칙에 따라 인코딩된 음성의 오디오 표현을 위한 방법 및 장치 |
| US6156694A (en) | 1998-11-05 | 2000-12-05 | E. I. Dupont De Nemours & Company | Raney cobalt catalyst and a process for hydrogenating organic compounds using said catalyst |
| AU2002303094B2 (en) | 2001-03-29 | 2006-11-23 | Eli Lilly And Company | N-(2-arylethyl)benzylamines as antagonists of the 5-HT6 receptor |
| US7084154B2 (en) * | 2003-02-11 | 2006-08-01 | Pharmacopeia Drug Disclovery, Inc. | 2-(aminomethyl) arylamide analgesics |
| FR2866335B1 (fr) | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
| JP2006169113A (ja) * | 2004-12-10 | 2006-06-29 | Dainippon Sumitomo Pharma Co Ltd | インドール類の合成方法および合成中間体 |
| WO2007070796A1 (en) * | 2005-12-15 | 2007-06-21 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
| EP2002834A1 (de) * | 2007-06-13 | 2008-12-17 | Bayer Schering Pharma Aktiengesellschaft | Aryl/Hetarylamide als Modulatoren des EP2-Rezeptors |
| JO2704B1 (en) * | 2007-09-21 | 2013-03-03 | جانسين فارماسوتيكا ان في | Interference inhibition factors between MD2 and B53 |
| EP2219646A4 (en) | 2007-12-21 | 2010-12-22 | Univ Rochester | METHOD FOR MODIFYING THE LIFETIME OF EUKARYOTIC ORGANISMS |
| WO2010036362A1 (en) * | 2008-09-26 | 2010-04-01 | Wyeth | 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate nuclear receptor inhibitors |
| CN101531624A (zh) | 2009-04-08 | 2009-09-16 | 大连凯飞精细化工有限公司 | 6-氟吲哚-3-乙腈的合成方法 |
| TW201139370A (en) | 2009-12-23 | 2011-11-16 | Lundbeck & Co As H | Processes for the manufacture of a pharmaceutically active agent |
-
2010
- 2010-12-16 TW TW099144129A patent/TW201139370A/zh unknown
- 2010-12-20 NZ NZ600639A patent/NZ600639A/en not_active IP Right Cessation
- 2010-12-20 EA EA201290552A patent/EA021440B1/ru not_active IP Right Cessation
- 2010-12-20 SG SG2012046793A patent/SG181910A1/en unknown
- 2010-12-20 CA CA2785440A patent/CA2785440C/en not_active Expired - Fee Related
- 2010-12-20 JP JP2012545093A patent/JP5864435B2/ja not_active Expired - Fee Related
- 2010-12-20 SI SI201031191A patent/SI2516394T1/sl unknown
- 2010-12-20 CN CN201080058864.9A patent/CN102656146B/zh not_active Expired - Fee Related
- 2010-12-20 ME MEP-2016-105A patent/ME02401B/me unknown
- 2010-12-20 NZ NZ625798A patent/NZ625798A/en not_active IP Right Cessation
- 2010-12-20 PT PT108032228T patent/PT2516394E/pt unknown
- 2010-12-20 GE GEAP201012807A patent/GEP20146078B/en unknown
- 2010-12-20 KR KR1020177031907A patent/KR101873182B1/ko active IP Right Grant
- 2010-12-20 BR BR112012015749A patent/BR112012015749A2/pt active Search and Examination
- 2010-12-20 EP EP10803222.8A patent/EP2516394B1/en active Active
- 2010-12-20 US US12/972,559 patent/US8461353B2/en not_active Expired - Fee Related
- 2010-12-20 MY MYPI2012002675A patent/MY159251A/en unknown
- 2010-12-20 RS RS20160382A patent/RS54820B1/sr unknown
- 2010-12-20 AU AU2010335659A patent/AU2010335659B2/en not_active Ceased
- 2010-12-20 HU HUE10803222A patent/HUE028806T2/en unknown
- 2010-12-20 MX MX2012007078A patent/MX2012007078A/es active IP Right Grant
- 2010-12-20 WO PCT/DK2010/050348 patent/WO2011076212A2/en active Application Filing
- 2010-12-20 MA MA35092A patent/MA33945B1/fr unknown
- 2010-12-20 ES ES10803222.8T patent/ES2575666T3/es active Active
- 2010-12-20 PL PL10803222.8T patent/PL2516394T3/pl unknown
- 2010-12-20 UA UAA201207977A patent/UA111584C2/uk unknown
- 2010-12-20 DK DK10803222.8T patent/DK2516394T3/en active
- 2010-12-20 KR KR1020127016217A patent/KR101796330B1/ko active IP Right Grant
- 2010-12-20 CN CN201410004542.6A patent/CN103694161B/zh not_active Expired - Fee Related
- 2010-12-21 AR ARP100104826A patent/AR079580A1/es active IP Right Grant
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2012
- 2012-05-31 TN TNP2012000279A patent/TN2012000279A1/en unknown
- 2012-06-12 IL IL220329A patent/IL220329A/en not_active IP Right Cessation
- 2012-06-12 CR CR20120316A patent/CR20120316A/es unknown
- 2012-06-18 DO DO2012000170A patent/DOP2012000170A/es unknown
- 2012-06-22 CL CL2012001725A patent/CL2012001725A1/es unknown
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2013
- 2013-02-25 HK HK13102334.6A patent/HK1174921A1/xx not_active IP Right Cessation
- 2013-05-02 US US13/875,623 patent/US8901318B2/en not_active Expired - Fee Related
- 2013-08-07 ZA ZA2013/05936A patent/ZA201305936B/en unknown
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2014
- 2014-02-25 IL IL231141A patent/IL231141A/en not_active IP Right Cessation
- 2014-09-26 HK HK14109681.9A patent/HK1196352A1/xx not_active IP Right Cessation
- 2014-11-25 US US14/553,029 patent/US9382205B2/en active Active
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2015
- 2015-12-24 JP JP2015251874A patent/JP6195605B2/ja not_active Expired - Fee Related
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2016
- 2016-05-16 HR HRP20160518TT patent/HRP20160518T1/hr unknown
- 2016-06-02 CY CY20161100488T patent/CY1118032T1/el unknown
- 2016-06-10 SM SM201600166T patent/SMT201600166B/it unknown
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