JP2013510883A5 - - Google Patents
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- Publication number
- JP2013510883A5 JP2013510883A5 JP2012539063A JP2012539063A JP2013510883A5 JP 2013510883 A5 JP2013510883 A5 JP 2013510883A5 JP 2012539063 A JP2012539063 A JP 2012539063A JP 2012539063 A JP2012539063 A JP 2012539063A JP 2013510883 A5 JP2013510883 A5 JP 2013510883A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- alkyl
- moiety
- formula
- membered saturated
- 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 35
- 229910052799 carbon Inorganic materials 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 15
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 15
- 238000000034 method Methods 0.000 claims 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- -1 NH 2 Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 4
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims 4
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 claims 4
- 230000004913 activation Effects 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 3
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 3
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 3
- 239000012069 chiral reagent Substances 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 2
- 239000007822 coupling agent Chemical class 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 230000002194 synthesizing effect Effects 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 150000005071 1,2,4-oxadiazoles Chemical class 0.000 claims 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims 1
- JRCCMJGRDJTQNS-UHFFFAOYSA-N 1-azido-1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC=C2C(N=[N+]=[N-])CCCC2=C1 JRCCMJGRDJTQNS-UHFFFAOYSA-N 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 206010022000 influenza Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000003223 protective agent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- YAYKSOJDDDOGPS-UHFFFAOYSA-O CC(C)Oc(c(C#N)c1)ccc1-c1nc(-c(c2c3CCCC2)ccc3[O]=S(CCO)([NH3+])=O)n[o]1 Chemical compound CC(C)Oc(c(C#N)c1)ccc1-c1nc(-c(c2c3CCCC2)ccc3[O]=S(CCO)([NH3+])=O)n[o]1 YAYKSOJDDDOGPS-UHFFFAOYSA-O 0.000 description 1
- CNZMZBQTAKCCQV-QFIPXVFZSA-N CC(C)Oc(c(C#N)c1)ccc1-c1nc(-c2c(CCC[C@@H]3NS(CCOC)(=O)=O)c3ccc2)n[o]1 Chemical compound CC(C)Oc(c(C#N)c1)ccc1-c1nc(-c2c(CCC[C@@H]3NS(CCOC)(=O)=O)c3ccc2)n[o]1 CNZMZBQTAKCCQV-QFIPXVFZSA-N 0.000 description 1
- HBNRRDKSYWXGOI-UHFFFAOYSA-N CC(C)Oc(c(C#N)c1)ccc1-c1nc(-c2cccc3c2CCCC3NS(C)(=O)=O)n[o]1 Chemical compound CC(C)Oc(c(C#N)c1)ccc1-c1nc(-c2cccc3c2CCCC3NS(C)(=O)=O)n[o]1 HBNRRDKSYWXGOI-UHFFFAOYSA-N 0.000 description 1
- OPLZCRMHHIAIII-QFIPXVFZSA-N CC(C)Oc(c(C#N)c1)ccc1-c1nc(-c2cccc3c2CCC[C@@H]3NC(N(C2)CC2O)=O)n[o]1 Chemical compound CC(C)Oc(c(C#N)c1)ccc1-c1nc(-c2cccc3c2CCC[C@@H]3NC(N(C2)CC2O)=O)n[o]1 OPLZCRMHHIAIII-QFIPXVFZSA-N 0.000 description 1
- ALWIXISWVWRUBC-WMZHIEFXSA-N CC(C)Oc(c(C#N)c1)ccc1-c1nc(-c2cccc3c2CCC[C@H]3NC(N(CC2)C[C@H]2O)=O)n[o]1 Chemical compound CC(C)Oc(c(C#N)c1)ccc1-c1nc(-c2cccc3c2CCC[C@H]3NC(N(CC2)C[C@H]2O)=O)n[o]1 ALWIXISWVWRUBC-WMZHIEFXSA-N 0.000 description 1
- QJMCZJVKZQJBLM-UHFFFAOYSA-N CC(C)Oc(ccc(-c1nc(-c2cccc3c2CCCC3NCCS(C)(=O)=O)n[o]1)c1)c1C#N Chemical compound CC(C)Oc(ccc(-c1nc(-c2cccc3c2CCCC3NCCS(C)(=O)=O)n[o]1)c1)c1C#N QJMCZJVKZQJBLM-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26128209P | 2009-11-13 | 2009-11-13 | |
| US61/261,282 | 2009-11-13 | ||
| US26247409P | 2009-11-18 | 2009-11-18 | |
| US61/262,474 | 2009-11-18 | ||
| PCT/US2010/056757 WO2011060389A1 (en) | 2009-11-13 | 2010-11-15 | Sphingosine 1 phosphate receptor modulators and methods of chiral synthesis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013510883A JP2013510883A (ja) | 2013-03-28 |
| JP2013510883A5 true JP2013510883A5 (https=) | 2014-01-09 |
| JP5988379B2 JP5988379B2 (ja) | 2016-09-07 |
Family
ID=43992104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012539063A Active JP5988379B2 (ja) | 2009-11-13 | 2010-11-15 | スフィンゴシン−１−リン酸受容体変調因子および不斉合成方法 |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US8357706B2 (https=) |
| EP (1) | EP2498611B1 (https=) |
| JP (1) | JP5988379B2 (https=) |
| KR (1) | KR101781233B1 (https=) |
| CN (1) | CN102724880B (https=) |
| AU (1) | AU2010320041B2 (https=) |
| BR (1) | BR112012011430A8 (https=) |
| CA (1) | CA2780433C (https=) |
| CY (1) | CY1120427T1 (https=) |
| DK (1) | DK2498611T3 (https=) |
| EA (1) | EA023183B1 (https=) |
| ES (1) | ES2665461T3 (https=) |
| HR (1) | HRP20180527T1 (https=) |
| HU (1) | HUE036391T2 (https=) |
| IL (1) | IL219690B (https=) |
| LT (1) | LT2498611T (https=) |
| MX (1) | MX2012005562A (https=) |
| MY (1) | MY160907A (https=) |
| NZ (1) | NZ599913A (https=) |
| PH (1) | PH12012500938A1 (https=) |
| PL (1) | PL2498611T3 (https=) |
| PT (1) | PT2498611T (https=) |
| RS (1) | RS57070B1 (https=) |
| SI (1) | SI2498611T1 (https=) |
| WO (1) | WO2011060389A1 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2665461T3 (es) | 2009-11-13 | 2018-04-25 | Celgene International Ii Sàrl | Moduladores del receptor esfingosina 1-fosfato y métodos de síntesis quiral |
| MX2012005560A (es) * | 2009-11-13 | 2012-10-05 | Receptos Inc | Moduladores selectivos del receptor de esfingosina 1 fosfato y metodos de sintesis quiral. |
| US9481659B2 (en) | 2011-05-13 | 2016-11-01 | Celgene International Ii Sàrl | Selective heterocyclic sphingosine 1 phosphate receptor modulators |
| CN103251950B (zh) * | 2012-02-16 | 2018-10-02 | 中国人民解放军军事科学院军事医学研究院辐射医学研究所 | S1p受体调节剂防治肠型放射病及放射性肠炎的用途 |
| US9481650B2 (en) * | 2012-11-16 | 2016-11-01 | Hoffmann La Roche Inc. | Process for the preparation of 2-trifluoromethyl isonicotinic acid and esters |
| PT2958913T (pt) | 2013-02-20 | 2018-12-03 | Lg Chemical Ltd | Agonistas de recetores de esfingosina-1-fosfato, métodos para a sua preparação e composições farmacêuticas que os contêm como agente ativo |
| WO2015066515A1 (en) * | 2013-11-01 | 2015-05-07 | Receptos, Inc. | Selective sphingosine 1 phosphate receptor modulators and combination therapy therewith |
| ES2932049T3 (es) | 2015-11-13 | 2023-01-09 | Oppilan Pharma Ltd | Compuestos heterocíclicos para el tratamiento de enfermedades |
| TW201730148A (zh) | 2015-12-22 | 2017-09-01 | 艾伯維德國有限兩合公司 | 作為s1p調節劑的稠合(雜)環化合物 |
| CA3022432A1 (en) * | 2016-04-29 | 2017-11-02 | Board Of Regents, The University Of Texas System | Sigma receptor binders |
| ES2877686T3 (es) * | 2016-07-22 | 2021-11-17 | Shijiazhuang Sagacity New Drug Dev Co Ltd | Agonista S1P1 y aplicación del mismo |
| CN106749213B (zh) * | 2016-11-25 | 2019-07-02 | 济南大学 | 一种具有1,2,4-恶二唑结构的吲哚衍生物及制备方法和在制备抗菌药物中的应用 |
| CN108727292A (zh) * | 2017-04-21 | 2018-11-02 | 宁波爱诺医药科技有限公司 | 一种奥扎莫德及其中间体的制备方法 |
| CN108727291A (zh) * | 2017-04-21 | 2018-11-02 | 宁波爱诺医药科技有限公司 | 奥扎莫德及其中间体的制备方法 |
| AR116479A1 (es) | 2018-09-25 | 2021-05-12 | Quim Sintetica S A | Intermediarios para la síntesis de ozanimod y procedimiento para la preparación del mencionado agonista del receptor de esfingosina-1-fosfato y de dichos intermediarios |
| CN110256288A (zh) * | 2019-05-13 | 2019-09-20 | 苏州山青竹生物医药有限公司 | 一种制备(s)-1-氨基-2,3-二氢-1h-茚-4-甲腈的方法 |
| CN112062785B (zh) * | 2019-06-11 | 2023-06-27 | 广东东阳光药业有限公司 | 奥扎莫德及其中间体的制备方法 |
| AU2021205465A1 (en) * | 2020-01-06 | 2022-07-14 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| EP4101445B1 (en) | 2020-02-06 | 2025-04-30 | Mitsubishi Tanabe Pharma Corporation | Amiselimod for use in the treatment of myalgic encephalomyelitis/chronic fatigue syndrome |
| WO2021175225A1 (zh) * | 2020-03-04 | 2021-09-10 | 南京明德新药研发有限公司 | 三环类化合物及其应用 |
| US12612401B2 (en) | 2022-07-06 | 2026-04-28 | Oppilan Pharma Limited | Crystalline forms of an S1P receptor modulator |
| EP4720047A1 (en) | 2023-05-31 | 2026-04-08 | Química Sintética, S.A. | Amorphous and crystalline form of ozanimod hydrochloride |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1479544A (en) * | 1974-02-07 | 1977-07-13 | American Cyanamid Co | 1,2,3,4-tetrahydro-1-naphthylurea derivatives their preparation and their use |
| FR2628103B1 (fr) | 1988-03-03 | 1991-06-14 | Roussel Uclaf | Nouveaux esters pyrethrinoides portant un noyau indanyle, leur procede de preparation et leur application comme pesticides |
| US5039802A (en) | 1990-04-18 | 1991-08-13 | Merck & Co., Inc. | Arylation process for preparation of chiral catalysts for ketone reduction |
| EP0583346A1 (en) | 1991-04-12 | 1994-02-23 | Schering Corporation | Bicyclic amides as inhibitors of acyl-coenzyme a: cholesterol acyl transferase |
| GB2290790A (en) * | 1994-06-30 | 1996-01-10 | Merck & Co Inc | Asymmetric synthesis of 6-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes |
| PT1057827E (pt) * | 1998-01-23 | 2003-11-28 | Sankyo Co | Derivados da espiropiperidina |
| US20040058894A1 (en) | 2002-01-18 | 2004-03-25 | Doherty George A. | Selective S1P1/Edg1 receptor agonists |
| DE60335827D1 (de) * | 2002-12-20 | 2011-03-03 | Merck Sharp & Dohme | 1-(amino)indane als edg-rezeptoragonisten |
| HUE047569T2 (hu) | 2003-04-11 | 2020-04-28 | Ptc Therapeutics Inc | 1,2,4-oxadiazol-benzoesav vegyület és nonszensz szupresszióra történõ alkalmazása |
| US20070043014A1 (en) * | 2003-10-01 | 2007-02-22 | Merck & Co., Inc. | 3,5-Aryl, heteroaryl or cycloalkyl substituted-1,2,4-oxadiazoles as s1p receptor agonists |
| EP1697333A4 (en) * | 2003-12-17 | 2009-07-08 | Merck & Co Inc | (3,4-DISUBSTITUTED) PROPANE ACID BOXYLATES AS AGONISTS OF THE S1P (EDG) RECEPTOR |
| US7585881B2 (en) * | 2004-02-18 | 2009-09-08 | Astrazeneca Ab | Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| US20060173183A1 (en) | 2004-12-31 | 2006-08-03 | Alantos Pharmaceuticals, Inc., | Multicyclic bis-amide MMP inhibitors |
| EP1851188A1 (en) | 2005-02-22 | 2007-11-07 | Teva Pharmaceutical Industries Limited | Improved process for the synthesis of enantiomeric indanylamine derivatives |
| KR100667075B1 (ko) | 2005-07-22 | 2007-01-10 | 삼성에스디아이 주식회사 | 주사 구동부 및 이를 포함하는 유기 전계발광 표시장치 |
| CA2634488C (en) | 2005-12-21 | 2016-10-04 | Joseph Gabriele | Catecholamine regulated protein |
| CA2643055A1 (en) | 2006-03-13 | 2007-09-20 | Pfizer Products Inc. | Tetralines antagonists of the h-3 receptor |
| US20080009534A1 (en) * | 2006-07-07 | 2008-01-10 | Bristol-Myers Squibb Company | Substituted acid derivatives useful as antidiabetic and antiobesity agents and method |
| EP2109364A4 (en) * | 2006-12-15 | 2010-04-14 | Abbott Lab | NOVEL OXADIAZONE COMPOUNDS |
| WO2008106204A1 (en) | 2007-02-28 | 2008-09-04 | Rib-X-Pharmaceuticals, Inc. | Macrolide compounds and methods of making and using the same |
| WO2009131090A1 (ja) | 2008-04-21 | 2009-10-29 | 旭化成ファーマ株式会社 | アミノ酸化合物 |
| EP3782991A1 (en) * | 2008-05-14 | 2021-02-24 | The Scripps Research Institute | Novel modulators of sphingosine phosphate receptors |
| WO2011005290A1 (en) | 2009-06-23 | 2011-01-13 | Arena Pharmaceuticals, Inc. | Disubstituted oxadiazole derivatives useful in the treatment of autoimmune and inflammatory disorders |
| ES2665461T3 (es) | 2009-11-13 | 2018-04-25 | Celgene International Ii Sàrl | Moduladores del receptor esfingosina 1-fosfato y métodos de síntesis quiral |
| MX2012005560A (es) * | 2009-11-13 | 2012-10-05 | Receptos Inc | Moduladores selectivos del receptor de esfingosina 1 fosfato y metodos de sintesis quiral. |
| PH12012500940B1 (en) | 2009-11-13 | 2018-09-26 | Receptos Llc | Selective heterocyclic sphingosine 1 phosphate receptor modulators |
| CA2851525A1 (en) | 2011-10-12 | 2013-04-18 | Teva Pharmaceutical Industries Ltd. | Treatment of multiple sclerosis with combination of laquinimod and fingolimod |
-
2010
- 2010-11-15 ES ES10830877.6T patent/ES2665461T3/es active Active
- 2010-11-15 JP JP2012539063A patent/JP5988379B2/ja active Active
- 2010-11-15 BR BR112012011430A patent/BR112012011430A8/pt not_active Application Discontinuation
- 2010-11-15 KR KR1020127015219A patent/KR101781233B1/ko active Active
- 2010-11-15 AU AU2010320041A patent/AU2010320041B2/en active Active
- 2010-11-15 NZ NZ599913A patent/NZ599913A/en unknown
- 2010-11-15 PT PT108308776T patent/PT2498611T/pt unknown
- 2010-11-15 EA EA201290331A patent/EA023183B1/ru not_active IP Right Cessation
- 2010-11-15 DK DK10830877.6T patent/DK2498611T3/en active
- 2010-11-15 WO PCT/US2010/056757 patent/WO2011060389A1/en not_active Ceased
- 2010-11-15 LT LTEP10830877.6T patent/LT2498611T/lt unknown
- 2010-11-15 HU HUE10830877A patent/HUE036391T2/hu unknown
- 2010-11-15 US US12/946,800 patent/US8357706B2/en active Active
- 2010-11-15 RS RS20180389A patent/RS57070B1/sr unknown
- 2010-11-15 CA CA2780433A patent/CA2780433C/en active Active
- 2010-11-15 MY MYPI2012002085A patent/MY160907A/en unknown
- 2010-11-15 EP EP10830877.6A patent/EP2498611B1/en active Active
- 2010-11-15 PH PH1/2012/500938A patent/PH12012500938A1/en unknown
- 2010-11-15 SI SI201031665T patent/SI2498611T1/en unknown
- 2010-11-15 MX MX2012005562A patent/MX2012005562A/es active IP Right Grant
- 2010-11-15 PL PL10830877T patent/PL2498611T3/pl unknown
- 2010-11-15 HR HRP20180527TT patent/HRP20180527T1/hr unknown
- 2010-11-15 CN CN201080061143.3A patent/CN102724880B/zh active Active
-
2012
- 2012-05-09 IL IL219690A patent/IL219690B/en active IP Right Grant
-
2013
- 2013-01-14 US US13/740,669 patent/US20130196966A1/en not_active Abandoned
-
2015
- 2015-02-27 US US14/634,439 patent/US9394264B2/en active Active
-
2018
- 2018-04-04 CY CY20181100376T patent/CY1120427T1/el unknown
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