JP2008519035A5 - - Google Patents
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- Publication number
- JP2008519035A5 JP2008519035A5 JP2007540055A JP2007540055A JP2008519035A5 JP 2008519035 A5 JP2008519035 A5 JP 2008519035A5 JP 2007540055 A JP2007540055 A JP 2007540055A JP 2007540055 A JP2007540055 A JP 2007540055A JP 2008519035 A5 JP2008519035 A5 JP 2008519035A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydrogen atom
- hydroxy
- carbonyl
- lower alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 9
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 6
- 239000004215 Carbon black (E152) Substances 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 229930195733 hydrocarbon Natural products 0.000 claims 3
- 150000002430 hydrocarbons Chemical class 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
- 102000003840 Opioid Receptors Human genes 0.000 claims 2
- 108090000137 Opioid Receptors Proteins 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 1
- 206010011224 Cough Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000017228 Gastrointestinal motility disease Diseases 0.000 claims 1
- 208000004454 Hyperalgesia Diseases 0.000 claims 1
- 208000035154 Hyperesthesia Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- KIBALXBELNWKRK-UHFFFAOYSA-N CN(CC1)C(Cc2ccc3C(N)=O)C(CCC(C4)=O)C14c2c3O Chemical compound CN(CC1)C(Cc2ccc3C(N)=O)C(CCC(C4)=O)C14c2c3O KIBALXBELNWKRK-UHFFFAOYSA-N 0.000 description 1
- SIIKUSQIIPEOEA-UHFFFAOYSA-N NC(c1ccc(CC2N(CC3CCC3)CCC3(CC(CC4)=O)C24O)c3c1O)=O Chemical compound NC(c1ccc(CC2N(CC3CCC3)CCC3(CC(CC4)=O)C24O)c3c1O)=O SIIKUSQIIPEOEA-UHFFFAOYSA-N 0.000 description 1
- NWIALXFYKPFWTR-UHFFFAOYSA-N NC(c1ccc(CC2N(CC3CCC3)CCC3(CC(CC4)O)C24O)c3c1O)=O Chemical compound NC(c1ccc(CC2N(CC3CCC3)CCC3(CC(CC4)O)C24O)c3c1O)=O NWIALXFYKPFWTR-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62534804P | 2004-11-05 | 2004-11-05 | |
| US60/625,348 | 2004-11-05 | ||
| PCT/US2005/039911 WO2006052710A1 (en) | 2004-11-05 | 2005-11-03 | 4-hydroxybenzomorphans |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012256445A Division JP6058981B2 (ja) | 2004-11-05 | 2012-11-22 | ４−ヒドロキシベンゾモルファン |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008519035A JP2008519035A (ja) | 2008-06-05 |
| JP2008519035A5 true JP2008519035A5 (OSRAM) | 2008-11-13 |
| JP5198067B2 JP5198067B2 (ja) | 2013-05-15 |
Family
ID=36128632
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007540055A Expired - Lifetime JP5198067B2 (ja) | 2004-11-05 | 2005-11-03 | ４−ヒドロキシベンゾモルファン |
| JP2012256445A Expired - Lifetime JP6058981B2 (ja) | 2004-11-05 | 2012-11-22 | ４−ヒドロキシベンゾモルファン |
| JP2015159733A Pending JP2016020364A (ja) | 2004-11-05 | 2015-08-12 | ４−ヒドロキシベンゾモルファン |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012256445A Expired - Lifetime JP6058981B2 (ja) | 2004-11-05 | 2012-11-22 | ４−ヒドロキシベンゾモルファン |
| JP2015159733A Pending JP2016020364A (ja) | 2004-11-05 | 2015-08-12 | ４−ヒドロキシベンゾモルファン |
Country Status (20)
| Country | Link |
|---|---|
| US (7) | US7262298B2 (OSRAM) |
| EP (2) | EP1817291A1 (OSRAM) |
| JP (3) | JP5198067B2 (OSRAM) |
| KR (1) | KR101115841B1 (OSRAM) |
| CN (1) | CN101090891B (OSRAM) |
| AT (1) | ATE557006T1 (OSRAM) |
| AU (1) | AU2005304950B2 (OSRAM) |
| BR (1) | BRPI0517091B8 (OSRAM) |
| CA (1) | CA2587074C (OSRAM) |
| CY (1) | CY1112946T1 (OSRAM) |
| DK (1) | DK2251330T3 (OSRAM) |
| ES (1) | ES2387737T3 (OSRAM) |
| IL (1) | IL182983A (OSRAM) |
| MX (1) | MX2007005389A (OSRAM) |
| NO (1) | NO340204B1 (OSRAM) |
| PL (1) | PL2251330T3 (OSRAM) |
| PT (1) | PT2251330E (OSRAM) |
| RU (2) | RU2480455C2 (OSRAM) |
| SI (1) | SI2251330T1 (OSRAM) |
| WO (1) | WO2006052710A1 (OSRAM) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60109960T2 (de) * | 2000-10-31 | 2006-02-16 | Rensselaer Polytechnic Institute | 8-substituierte 2,6-methano-3-benzazocine und 3-substituierte morphinane als opioidrezeptorbindende agenzien |
| MX2007005389A (es) * | 2004-11-05 | 2007-12-07 | Rensselaer Polytech Inst | 4-hidroxibenzomorfanos. |
| ES2480390T3 (es) | 2005-07-21 | 2014-07-28 | Rensselaer Polytechnic Institute | 2,6-metano-3-benzazocinas 8-carboxamido sustituidas y morfanos 3-carboxamido sustituidos como ligandos de los receptores opioides |
| ATE493416T1 (de) | 2007-05-04 | 2011-01-15 | Mallinckrodt Inc | Verbessertes verfahren zur herstellung von 6- alpha-hydroxy-n-alkylierten opiaten |
| AU2008276385B2 (en) | 2007-07-17 | 2013-07-18 | SpecGx LLC | Preparation of N-alkylated opiates by reductive amination |
| JP5581211B2 (ja) | 2007-08-09 | 2014-08-27 | レンセラール ポリテクニック インスティチュート | 第四級オピオイドカルボキサミド |
| CN102227434B (zh) | 2008-09-30 | 2015-02-18 | 马林克罗特有限公司 | 选择性胺化酮吗啡喃的方法 |
| US8946419B2 (en) | 2009-02-23 | 2015-02-03 | Mallinckrodt Llc | (+)-6-hydroxy-morphinan or (+)-6-amino-morphinan derivatives |
| AU2009342654B2 (en) * | 2009-03-19 | 2013-09-05 | Alkermes Pharma Ireland Limited | Morphinan derivatives with high oral bioavailability |
| WO2010118274A1 (en) * | 2009-04-09 | 2010-10-14 | Mallinckrodt Inc. | Preparation of 6-keto, 3-alkoxy morphinans |
| EP2440561B1 (en) | 2009-06-11 | 2014-04-30 | Mallinckrodt LLC | Reductive amination of 6-keto normorphinans by catalytic hydrogen transfer |
| EP2440562B1 (en) | 2009-06-11 | 2016-08-10 | Mallinckrodt LLC | Preparation of 6-alpha-amino n-substituted morphinans by catalytic hydrogen transfer |
| HRP20191029T1 (hr) * | 2009-12-04 | 2019-09-20 | Alkermes Pharma Ireland Limited | Derivati morfinana radi liječenja predoziranja lijekom |
| ES2582306T3 (es) | 2010-03-22 | 2016-09-12 | Rensselaer Polytechnic Institute | Derivados de morfinano que contienen un grupo carboxamida como ligandos de receptores opioides |
| US8563725B2 (en) | 2010-04-29 | 2013-10-22 | Mallinckrodt Llc | Preparation of saturated ketone morphinan compounds having low metal content |
| ES2708726T3 (es) | 2010-07-08 | 2019-04-10 | Alkermes Pharma Ireland Ltd | Proceso para la síntesis de morfinanos sustituidos |
| HRP20240109T1 (hr) | 2010-08-23 | 2024-03-29 | Alkermes Pharma Ireland Limited | Postupci za liječenje povećanja tjelesne težine induciranog antipsihoticima |
| US9029543B2 (en) | 2011-04-05 | 2015-05-12 | Alkermes, Inc. | Process for the synthesis of quaternary amine compounds |
| ES2698408T3 (es) | 2011-06-09 | 2019-02-04 | SpecGx LLC | Aminación reductora de 6-ceto morfinanos por transferencia de hidrógeno catalítico |
| AU2012275181B2 (en) | 2011-06-29 | 2016-04-07 | Alkermes, Inc. | Peripherally acting opioid compounds |
| MX2014002630A (es) | 2011-09-08 | 2014-04-14 | Mallinckrodt Llc | Produccion de alcaloides sin el aislamiento de compuestos intermediarios. |
| RS58322B1 (sr) | 2011-12-15 | 2019-03-29 | Alkermes Pharma Ireland Ltd | Samidorfan (alks 33) u kombinaciji sa buprenorfinom za lečenje depresivnih poremećaja |
| US9211293B2 (en) | 2011-12-15 | 2015-12-15 | Alkermes Pharma Ireland Limited | Opioid agonist antagonist combinations |
| EP3003311A2 (en) | 2013-05-24 | 2016-04-13 | Alkermes Pharma Ireland Limited | Methods for treating depressive symptoms |
| JP2016519161A (ja) | 2013-05-24 | 2016-06-30 | アルカームス ファーマ アイルランド リミテッド | モルファン及びモルフィナン類似物及び使用の方法 |
| CN110352055A (zh) * | 2017-03-02 | 2019-10-18 | 株式会社三和化学研究所 | 酒精使用障碍的治疗药物 |
| CN107089948B (zh) * | 2017-04-28 | 2020-07-17 | 云南大学 | 吗吩衍生物及其制备方法和应用 |
| CN111978252A (zh) * | 2019-05-21 | 2020-11-24 | 复旦大学 | 手性苯并吗吩烷类衍生物及其制备方法和在药学上的应用 |
| TW202140009A (zh) * | 2020-02-13 | 2021-11-01 | 大陸商上海翰森生物醫藥科技有限公司 | ３－甲醯胺基－４－羥基納曲酮氘代衍生物、其製備方法及其在醫藥上的應用 |
| CN111205151B (zh) * | 2020-02-29 | 2021-03-05 | 深圳市祥根生物科技有限公司 | 一种布洛芬杂质i的环保制备方法 |
| EP4243768A1 (en) | 2020-11-12 | 2023-09-20 | Alkermes Pharma Ireland Limited | Immediate release multilayer tablet |
| CN114621238A (zh) * | 2020-12-10 | 2022-06-14 | 鲁南制药集团股份有限公司 | 一种制备纳呋拉啡的方法 |
| KR102663533B1 (ko) * | 2021-11-09 | 2024-05-08 | 백미선 | 레이저 치료기기용 온냉각장치 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4032529A (en) | 1974-09-20 | 1977-06-28 | Sterling Drug Inc. | Aminomethanobenzazocine intermediates |
| US3957793A (en) | 1974-09-20 | 1976-05-18 | Sterling Drug Inc. | Hydroxyiminobenzazocines |
| SU635868A3 (ru) * | 1974-11-12 | 1978-11-30 | Бристол Мейерз Компани (Фирма) | Способ получени морфиновых производных или их солей |
| US4205171A (en) | 1976-01-12 | 1980-05-27 | Sterling Drug Inc. | Aminomethanobenzazocines and nitromethanobenzazocines |
| US4373139A (en) | 1979-04-30 | 1983-02-08 | Motorola, Inc. | Detectors |
| US4649200A (en) | 1986-05-08 | 1987-03-10 | Regents Of The University Of Minnesota | Substituted pyrroles with opioid receptor activity |
| EP0632041A1 (en) | 1993-07-01 | 1995-01-04 | Katholieke Universiteit Nijmegen | New morphine derivatives having improved analgesic and narcotic properties |
| AR005423A1 (es) | 1996-01-10 | 1999-06-23 | Smithkline Beecham Spa | Derivados morfinoides condensados con heterociclos (ii), su uso como sustancia terapeutica y para preparar medicamentos, composiciones farmaceuticasque los contienen y procedimiento para preparar dichos derivados. |
| DE60109960T2 (de) | 2000-10-31 | 2006-02-16 | Rensselaer Polytechnic Institute | 8-substituierte 2,6-methano-3-benzazocine und 3-substituierte morphinane als opioidrezeptorbindende agenzien |
| WO2004007449A1 (en) | 2002-07-16 | 2004-01-22 | Rensselaer Polytechnic Institute | Process for conversion of phenols to carboxamides via the succinimide esters |
| MX2007005389A (es) * | 2004-11-05 | 2007-12-07 | Rensselaer Polytech Inst | 4-hidroxibenzomorfanos. |
-
2005
- 2005-11-03 MX MX2007005389A patent/MX2007005389A/es active IP Right Grant
- 2005-11-03 CA CA2587074A patent/CA2587074C/en not_active Expired - Lifetime
- 2005-11-03 BR BRPI0517091A patent/BRPI0517091B8/pt active IP Right Grant
- 2005-11-03 SI SI200531549T patent/SI2251330T1/sl unknown
- 2005-11-03 KR KR1020077012582A patent/KR101115841B1/ko not_active Expired - Lifetime
- 2005-11-03 EP EP05851351A patent/EP1817291A1/en not_active Withdrawn
- 2005-11-03 DK DK10008474.8T patent/DK2251330T3/da active
- 2005-11-03 ES ES10008474T patent/ES2387737T3/es not_active Expired - Lifetime
- 2005-11-03 JP JP2007540055A patent/JP5198067B2/ja not_active Expired - Lifetime
- 2005-11-03 RU RU2010147915/04A patent/RU2480455C2/ru active
- 2005-11-03 EP EP10008474A patent/EP2251330B1/en not_active Expired - Lifetime
- 2005-11-03 CN CN2005800451698A patent/CN101090891B/zh not_active Expired - Lifetime
- 2005-11-03 US US11/266,651 patent/US7262298B2/en not_active Expired - Lifetime
- 2005-11-03 WO PCT/US2005/039911 patent/WO2006052710A1/en not_active Ceased
- 2005-11-03 AT AT10008474T patent/ATE557006T1/de active
- 2005-11-03 RU RU2007120759/04A patent/RU2415131C2/ru active
- 2005-11-03 PT PT10008474T patent/PT2251330E/pt unknown
- 2005-11-03 AU AU2005304950A patent/AU2005304950B2/en not_active Expired
- 2005-11-03 PL PL10008474T patent/PL2251330T3/pl unknown
-
2007
- 2007-05-03 IL IL182983A patent/IL182983A/en active IP Right Grant
- 2007-06-04 NO NO20072839A patent/NO340204B1/no unknown
- 2007-06-08 US US11/760,039 patent/US8680112B2/en active Active
-
2012
- 2012-07-31 CY CY20121100677T patent/CY1112946T1/el unknown
- 2012-11-22 JP JP2012256445A patent/JP6058981B2/ja not_active Expired - Lifetime
-
2013
- 2013-04-15 US US13/862,975 patent/US20130231361A1/en not_active Abandoned
-
2014
- 2014-01-31 US US14/169,305 patent/US8802655B2/en not_active Expired - Lifetime
- 2014-07-02 US US14/321,885 patent/US20150011768A1/en not_active Abandoned
-
2015
- 2015-04-27 US US14/697,013 patent/US20160075658A1/en not_active Abandoned
- 2015-08-12 JP JP2015159733A patent/JP2016020364A/ja active Pending
-
2023
- 2023-04-17 US US18/301,336 patent/US20240092740A1/en not_active Abandoned
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