JP2014503356A5 - - Google Patents
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- Publication number
- JP2014503356A5 JP2014503356A5 JP2013549616A JP2013549616A JP2014503356A5 JP 2014503356 A5 JP2014503356 A5 JP 2014503356A5 JP 2013549616 A JP2013549616 A JP 2013549616A JP 2013549616 A JP2013549616 A JP 2013549616A JP 2014503356 A5 JP2014503356 A5 JP 2014503356A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- heteroatom
- aryl
- hydrocarbyl
- ligand
- 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
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- 125000005842 heteroatom Chemical group 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 26
- 239000003446 ligand Substances 0.000 claims 23
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000000129 anionic group Chemical group 0.000 claims 13
- 125000000743 hydrocarbylene group Chemical group 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 239000003054 catalyst Substances 0.000 claims 8
- 238000005865 alkene metathesis reaction Methods 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- -1 heteroalkenyl Chemical group 0.000 claims 6
- 230000007935 neutral effect Effects 0.000 claims 6
- 125000003107 substituted aryl group Chemical group 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 229910002651 NO3 Inorganic materials 0.000 claims 5
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 5
- 239000013522 chelant Substances 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 229910052698 phosphorus Inorganic materials 0.000 claims 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims 4
- 125000000524 functional group Chemical group 0.000 claims 4
- 229910052723 transition metal Inorganic materials 0.000 claims 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 3
- 229910019142 PO4 Inorganic materials 0.000 claims 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 150000001450 anions Chemical class 0.000 claims 3
- 150000007942 carboxylates Chemical class 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 3
- 239000010452 phosphate Substances 0.000 claims 3
- 229910052709 silver Inorganic materials 0.000 claims 3
- 239000004332 silver Substances 0.000 claims 3
- 229910052708 sodium Inorganic materials 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- 150000003624 transition metals Chemical class 0.000 claims 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical group [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 229910052788 barium Inorganic materials 0.000 claims 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052792 caesium Inorganic materials 0.000 claims 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 2
- 229910052791 calcium Inorganic materials 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- BWOVZCWSJFYBRM-UHFFFAOYSA-N carbononitridic isocyanate Chemical compound O=C=NC#N BWOVZCWSJFYBRM-UHFFFAOYSA-N 0.000 claims 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 claims 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000002466 imines Chemical class 0.000 claims 2
- 229910052742 iron Inorganic materials 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 229910052744 lithium Inorganic materials 0.000 claims 2
- 229910052749 magnesium Inorganic materials 0.000 claims 2
- 239000011777 magnesium Substances 0.000 claims 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- 229910052701 rubidium Inorganic materials 0.000 claims 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims 2
- 229910000077 silane Inorganic materials 0.000 claims 2
- 229910052712 strontium Inorganic materials 0.000 claims 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 125000005717 substituted cycloalkylene group Chemical group 0.000 claims 2
- 229910052716 thallium Inorganic materials 0.000 claims 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 239000005973 Carvone Substances 0.000 claims 1
- 238000010499 C–H functionalization reaction Methods 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims 1
- 125000005135 aryl sulfinyl group Chemical group 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052762 osmium Inorganic materials 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004385 trihaloalkyl group Chemical group 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161432849P | 2011-01-14 | 2011-01-14 | |
| US61/432,849 | 2011-01-14 | ||
| US201161433949P | 2011-01-18 | 2011-01-18 | |
| US61/433,949 | 2011-01-18 | ||
| US201161515262P | 2011-08-04 | 2011-08-04 | |
| US61/515,262 | 2011-08-04 | ||
| PCT/US2012/021609 WO2012097379A2 (en) | 2011-01-14 | 2012-01-17 | Z-selective olefin metathesis catalysts and their synthetic procedure |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014503356A JP2014503356A (ja) | 2014-02-13 |
| JP2014503356A5 true JP2014503356A5 (https=) | 2015-02-26 |
| JP5893646B2 JP5893646B2 (ja) | 2016-03-23 |
Family
ID=46507707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013549616A Expired - Fee Related JP5893646B2 (ja) | 2011-01-14 | 2012-01-17 | Ｚ選択的オレフィンメタセシス触媒及びその合成手順 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9597674B2 (https=) |
| EP (1) | EP2663398B1 (https=) |
| JP (1) | JP5893646B2 (https=) |
| KR (1) | KR101835170B1 (https=) |
| CN (1) | CN103402628B (https=) |
| AU (1) | AU2012206966B2 (https=) |
| BR (1) | BR112013017938B1 (https=) |
| CA (1) | CA2824518C (https=) |
| IL (1) | IL227432A (https=) |
| PL (1) | PL2663398T3 (https=) |
| SG (1) | SG191980A1 (https=) |
| WO (1) | WO2012097379A2 (https=) |
| ZA (2) | ZA201305726B (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2838359A4 (en) | 2012-03-05 | 2015-12-09 | California Inst Of Techn | SYNTHESIS OF Z-OLEFIN-CONTAINING PHEROMONES OF LEPIDOPTERA INSECTS |
| JP6092379B2 (ja) | 2012-06-29 | 2017-03-08 | アペイロン シンセシス エス アー | 金属錯体、その適用、及びメタセシス反応の実施方法 |
| US9147844B2 (en) | 2012-08-01 | 2015-09-29 | California Institute Of Technology | Solvent-free enyne metathesis polymerization |
| US9234985B2 (en) | 2012-08-01 | 2016-01-12 | California Institute Of Technology | Birefringent polymer brush structures formed by surface initiated ring-opening metathesis polymerization |
| BR112015013580A2 (pt) | 2012-12-12 | 2017-07-11 | California Inst Of Techn | catalisador de metátese z-seletiva |
| US9758445B2 (en) | 2013-04-09 | 2017-09-12 | Materia, Inc. | Preparation of surfactants via cross-metathesis |
| US9663440B2 (en) | 2013-04-09 | 2017-05-30 | Materia, Inc. | Cross metathesis of poly-branched poly-olefins |
| ES2699416T3 (es) | 2013-04-09 | 2019-02-11 | Materia Inc | Preparación de tensioactivos mediante metátesis cruzada |
| US20160101414A1 (en) * | 2013-05-15 | 2016-04-14 | California Institute Of Technology | Highly z-selective and enantioselective ring opening/cross metathesis catalyzed by a resolved stereogenic-at-ru complex |
| EP3008078B1 (en) | 2013-06-12 | 2018-12-19 | Trustees of Boston College | Catalysts for efficient z-selective metathesis |
| WO2016014954A1 (en) * | 2014-07-25 | 2016-01-28 | California Institute Of Technology | Tandem z-selective metathesis / dihydroxylation |
| PL3353187T3 (pl) * | 2015-09-24 | 2021-11-22 | Umicore Ag & Co. Kg | Katalizatory metatezy olefin na bazie karbenu metalu |
| KR20180116238A (ko) | 2015-12-10 | 2018-10-24 | 우미코레 아게 운트 코 카게 | 올레핀 복분해 촉매 |
| CN114106057B (zh) * | 2016-10-19 | 2023-06-23 | 优美科股份公司及两合公司 | Ru亚烷基络合物的合成与表征 |
| US10320390B1 (en) | 2016-11-17 | 2019-06-11 | X Development Llc | Field programmable gate array including coupled lookup tables |
| WO2018220088A1 (en) | 2017-05-30 | 2018-12-06 | Ximo Ag | Methods of making olefinic e- and z-isomers |
| EP3762143A1 (en) * | 2018-03-09 | 2021-01-13 | PPG Industries Ohio Inc. | Compounds for coordinating with a metal, compositions containing such compounds, and methods of catalyzing reactions |
| CN112119055A (zh) * | 2018-05-15 | 2020-12-22 | 加利福尼亚技术学院 | 通过立体保留性复分解全合成前列腺素j天然产物 |
| US11939410B2 (en) * | 2018-06-29 | 2024-03-26 | Apeiron Synthesis S.A. | Organoruthenium complexes as precatalysts for olefin metathesis |
| CN114206889A (zh) * | 2019-07-17 | 2022-03-18 | 加利福尼亚技术学院 | Z选择性烯烃复分解催化剂的新合成 |
| EP4069667A1 (en) * | 2020-03-05 | 2022-10-12 | Firmenich SA | Process for preparing perfuming intermediate |
| CN115298191A (zh) * | 2020-03-13 | 2022-11-04 | 伊利诺伊大学评议会 | 催化氢化硅烷化的方法 |
| CN114478166B (zh) * | 2020-10-26 | 2024-09-27 | 中国石油天然气股份有限公司 | 一种制备端烯烃的方法 |
| CN118056617A (zh) * | 2022-11-15 | 2024-05-21 | 中国石油天然气股份有限公司 | 一种用于1-己烯自歧化的负载型催化剂及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5312940A (en) | 1992-04-03 | 1994-05-17 | California Institute Of Technology | Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization |
| US6284852B1 (en) | 1997-10-30 | 2001-09-04 | California Institute Of Technology | Acid activation of ruthenium metathesis catalysts and living ROMP metathesis polymerization in water |
| JP3943015B2 (ja) | 2000-08-10 | 2007-07-11 | トラスティーズ オブ ボストン カレッジ | リサイクル可能メタセシス触媒 |
| US6620955B1 (en) | 2001-11-15 | 2003-09-16 | Richard L. Pederson | Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts |
| CN1659172B (zh) * | 2002-04-05 | 2012-08-01 | 加州理工学院 | 直接被吸电子基团取代的烯烃使用过渡金属卡宾催化剂的交叉-易位 |
| AU2005252276B2 (en) * | 2004-06-09 | 2010-10-14 | Uti Limited Partnership | Transition metal carbene complexes containing a cationic substituent as catalysts of olefin metathesis reactions |
| FR2878246B1 (fr) | 2004-11-23 | 2007-03-30 | Inst Francais Du Petrole | Procede de co-production d'olefines et d'esters par ethenolyse de corps gras insatures dans des liquides ioniques non-aqueux |
| WO2007003135A1 (en) * | 2005-07-04 | 2007-01-11 | Zheng-Yun Zhan | Ruthenium complex ligand, ruthenium complex, carried ruthenium complex catalyst and the preparing methods and the use thereof |
| US8877936B2 (en) * | 2008-04-09 | 2014-11-04 | California Institute Of Technology | Ruthenium olefin metathesis catalysts bearing N-heterocyclic carbene ligands with substituted backbone |
| EP2255877B1 (en) * | 2009-05-07 | 2014-09-24 | Umicore AG & Co. KG | Method for preparation of ruthenium-based metathesis catalysts with chelating alkylidene ligands |
-
2012
- 2012-01-17 WO PCT/US2012/021609 patent/WO2012097379A2/en not_active Ceased
- 2012-01-17 AU AU2012206966A patent/AU2012206966B2/en not_active Ceased
- 2012-01-17 BR BR112013017938-4A patent/BR112013017938B1/pt active IP Right Grant
- 2012-01-17 PL PL12734668T patent/PL2663398T3/pl unknown
- 2012-01-17 SG SG2013054085A patent/SG191980A1/en unknown
- 2012-01-17 KR KR1020137021063A patent/KR101835170B1/ko not_active Expired - Fee Related
- 2012-01-17 JP JP2013549616A patent/JP5893646B2/ja not_active Expired - Fee Related
- 2012-01-17 CN CN201280010878.2A patent/CN103402628B/zh active Active
- 2012-01-17 CA CA2824518A patent/CA2824518C/en not_active Expired - Fee Related
- 2012-01-17 EP EP12734668.2A patent/EP2663398B1/en active Active
- 2012-01-17 US US13/978,940 patent/US9597674B2/en active Active
-
2013
- 2013-07-11 IL IL227432A patent/IL227432A/en active IP Right Grant
- 2013-07-29 ZA ZA2013/05726A patent/ZA201305726B/en unknown
-
2014
- 2014-11-04 ZA ZA2014/08071A patent/ZA201408071B/en unknown
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