DK2350046T3 - Fremgangsmåde til fremstilling af en krystalform, der ikke kan hydreres - Google Patents
Fremgangsmåde til fremstilling af en krystalform, der ikke kan hydreres Download PDFInfo
- Publication number
- DK2350046T3 DK2350046T3 DK09764118.7T DK09764118T DK2350046T3 DK 2350046 T3 DK2350046 T3 DK 2350046T3 DK 09764118 T DK09764118 T DK 09764118T DK 2350046 T3 DK2350046 T3 DK 2350046T3
- Authority
- DK
- Denmark
- Prior art keywords
- polymorph
- compound
- water
- mixture
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 48
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 23
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 22
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 14
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 8
- 238000002441 X-ray diffraction Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- -1 3-chloro-2-pyridinyl Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 229940125904 compound 1 Drugs 0.000 description 48
- 239000013078 crystal Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 14
- 239000002002 slurry Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000001035 drying Methods 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000007791 liquid phase Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 238000000634 powder X-ray diffraction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000013019 agitation Methods 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 2
- 101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Proteins 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000010268 HPLC based assay Methods 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000004497 NIR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 150000001924 cycloalkanes Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000013022 formulation composition Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (15)
- FREMGANGSMÅDE TIL FREMSTILLING AF EN KRYSTALFORM, DER IKKE KAN HYDRERES PATENTKRAV1. Fremgangsmåde til fremstilling af en polymorf A af 3-brom-l-(3-chlor-2-pyridinyl)-V-[4-cyan-2- methyl-6-[(methylamino)carbonyl]phenyl]-l//-pyrazol-5-carboxamid, kendetegnet ved et røntgendiffraktionsmønster, der har mindst de 2Θ reflektionspositioner,og som omfatter opvarmning til en temperatur på mellem 40 °C og opløsningsmidlets kogepunkt af en blanding, der omfatter et opløsningsmiddel, der er udvalgt fra gruppen bestående af vand, w-heptan, 1-chlorbutan, toluen, 1-butanol og 1-pentanol, og polymorf B af 3-brom-l-(3-chlor-2-pyridinyl)-IV-[4-cyan-2-methyl-6-[(methylamino)carbonyl]phenyl]-l//-pyrazol-5-carboxamid, kendetegnet ved et røntgendiffraktionsmønster, der har mindst de 2Θ reflektionspositioner
- 2. Fremgangsmåde ifølge krav 1, hvor opløsningsmidlet er n-heptan.
- 3. Fremgangsmåde ifølge krav 1, hvor opløsningsmidlet er toluen.
- 4. Fremgangsmåde ifølge krav 1, hvor opløsningsmidlet er 1-chlorbutan.
- 5. Fremgangsmåde ifølge krav 1, hvor opløsningsmidlet er 1-butanol eller 1-pentanol.
- 6. Fremgangsmåde ifølge krav 1, hvor opløsningsmidlet er vand.
- 7. Fremgangsmåde ifølge krav 6, hvor temperaturen er på mellem 60 og 100 °C.
- 8. Fremgangsmåde ifølge krav 7, hvor temperaturen er på mellem 70 og 100 °C.
- 9. Fremgangsmåde ifølge krav 8, hvor temperaturen er på mellem 70 og 90 °C.
- 10. Fremgangsmåde ifølge krav 6, hvor blandingen opvarmes i mindst 2 timer.
- 11. Fremgangsmåde ifølge krav 10, hvor blandingen opvarmes i ikke mere end 48 timer.
- 12. Fremgangsmåde ifølge krav 11, hvor blandingen opvarmes i ikke mere end 24 timer.
- 13. Fremgangsmåde ifølge krav 12, hvor blandingen opvarmes i ikke mere end 12 timer.
- 14. Fremgangsmåde ifølge krav 6, hvor 0,1 - 10 vægt-% af polymorf A i forhold til vægten af polymorf B tilføres blandingen forud for opvarmning.
- 15. Fremgangsmåde ifølge krav 14, hvor 0,2 - 5 vægt-% af polymorf A i forhold til vægten af polymorf B tilføres blandingen forud for opvarmning.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11462908P | 2008-11-14 | 2008-11-14 | |
| PCT/US2009/063991 WO2010056720A1 (en) | 2008-11-14 | 2009-11-11 | Method for preparing a non-hydratable crystal form |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2350046T3 true DK2350046T3 (da) | 2014-03-24 |
Family
ID=42044745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK09764118.7T DK2350046T3 (da) | 2008-11-14 | 2009-11-11 | Fremgangsmåde til fremstilling af en krystalform, der ikke kan hydreres |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8410278B2 (da) |
| EP (1) | EP2350046B8 (da) |
| JP (1) | JP5570520B2 (da) |
| KR (1) | KR101693901B1 (da) |
| CN (1) | CN102216284B (da) |
| AU (1) | AU2009314203B2 (da) |
| BR (1) | BRPI0914531B1 (da) |
| CA (1) | CA2737932C (da) |
| DK (1) | DK2350046T3 (da) |
| ES (1) | ES2445699T3 (da) |
| IL (1) | IL211727A (da) |
| MX (1) | MX2011004950A (da) |
| MY (1) | MY150568A (da) |
| PL (1) | PL2350046T3 (da) |
| RS (1) | RS53150B (da) |
| RU (1) | RU2500676C2 (da) |
| UA (1) | UA101395C2 (da) |
| WO (1) | WO2010056720A1 (da) |
| ZA (1) | ZA201101855B (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY142967A (en) | 2001-08-13 | 2011-01-31 | Du Pont | Method for controlling particular insect pests by applying anthranilamide compounds |
| TWI283164B (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| PE20231381A1 (es) * | 2020-06-08 | 2023-09-07 | Adama Makhteshim Ltd | Proceso para la preparacion de antranilamidas |
| US20250026732A1 (en) * | 2021-11-24 | 2025-01-23 | Natco Pharma Limited | An improved process for the preparation of crystalline form-a of cyantraniliprole |
| AR131889A1 (es) * | 2023-02-21 | 2025-05-14 | Upl Ltd | Un proceso para la preparación de un compuesto de antranilamida e intermedios del mismo |
| PY2419787A (es) | 2023-03-15 | 2024-11-28 | Adama Makhteshim Ltd | Composición en suspensión acuosa de cianraniliprol y acetamiprid |
| WO2025104727A1 (en) | 2023-11-16 | 2025-05-22 | Adama Makhteshim Ltd. | Solid state forms of cyantraniliprole and uses thereof |
| CN118146190A (zh) * | 2024-02-01 | 2024-06-07 | 南开大学 | 溴氰虫酰胺的新晶型及其制备方法和应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0003154D0 (en) | 2000-02-12 | 2000-04-05 | Astrazeneca Uk Ltd | Novel compounds |
| EP1429772A1 (en) | 2001-09-25 | 2004-06-23 | Pharmacia Corporation | N-(2-hydroxyacetyl)-5-(4-piperidyl)-4-(4-pyrimidinyl)-3-(4-chlorophenyl)pyrazole |
| SI1599463T1 (sl) * | 2003-01-28 | 2013-10-30 | E.I. Du Pont De Nemours And Company | Ciano antranilamidni insekticidi |
| TWI363756B (en) * | 2004-12-07 | 2012-05-11 | Du Pont | Method for preparing n-phenylpyrazole-1-carboxamides |
| JP5449669B2 (ja) | 2006-12-14 | 2014-03-19 | 石原産業株式会社 | 有害生物防除組成物 |
| JP5551371B2 (ja) * | 2008-03-24 | 2014-07-16 | 石原産業株式会社 | 有害生物防除用固形組成物 |
-
2009
- 2009-11-11 RS RS20140043A patent/RS53150B/sr unknown
- 2009-11-11 JP JP2011536436A patent/JP5570520B2/ja active Active
- 2009-11-11 PL PL09764118T patent/PL2350046T3/pl unknown
- 2009-11-11 DK DK09764118.7T patent/DK2350046T3/da active
- 2009-11-11 CA CA2737932A patent/CA2737932C/en active Active
- 2009-11-11 MX MX2011004950A patent/MX2011004950A/es active IP Right Grant
- 2009-11-11 WO PCT/US2009/063991 patent/WO2010056720A1/en not_active Ceased
- 2009-11-11 CN CN200980145282.1A patent/CN102216284B/zh active Active
- 2009-11-11 RU RU2011123800/04A patent/RU2500676C2/ru active
- 2009-11-11 MY MYPI20111233 patent/MY150568A/en unknown
- 2009-11-11 UA UAA201103962A patent/UA101395C2/ru unknown
- 2009-11-11 BR BRPI0914531-1A patent/BRPI0914531B1/pt active IP Right Grant
- 2009-11-11 AU AU2009314203A patent/AU2009314203B2/en active Active
- 2009-11-11 US US13/121,218 patent/US8410278B2/en active Active
- 2009-11-11 EP EP09764118.7A patent/EP2350046B8/en active Active
- 2009-11-11 KR KR1020117013504A patent/KR101693901B1/ko active Active
- 2009-11-11 ES ES09764118.7T patent/ES2445699T3/es active Active
-
2011
- 2011-03-10 ZA ZA2011/01855A patent/ZA201101855B/en unknown
- 2011-03-14 IL IL211727A patent/IL211727A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| EP2350046A1 (en) | 2011-08-03 |
| BRPI0914531A2 (pt) | 2015-08-04 |
| BRPI0914531B1 (pt) | 2021-01-05 |
| IL211727A0 (en) | 2011-06-30 |
| PL2350046T3 (pl) | 2014-05-30 |
| EP2350046B1 (en) | 2014-01-01 |
| EP2350046B8 (en) | 2014-04-02 |
| JP2012508747A (ja) | 2012-04-12 |
| KR20110082632A (ko) | 2011-07-19 |
| MY150568A (en) | 2014-01-30 |
| UA101395C2 (ru) | 2013-03-25 |
| ES2445699T3 (es) | 2014-03-04 |
| CN102216284B (zh) | 2014-02-19 |
| CA2737932A1 (en) | 2010-05-20 |
| WO2010056720A1 (en) | 2010-05-20 |
| KR101693901B1 (ko) | 2017-01-06 |
| JP5570520B2 (ja) | 2014-08-13 |
| AU2009314203B2 (en) | 2015-01-22 |
| US8410278B2 (en) | 2013-04-02 |
| IL211727A (en) | 2014-02-27 |
| AU2009314203A1 (en) | 2010-05-20 |
| RU2011123800A (ru) | 2012-12-20 |
| CN102216284A (zh) | 2011-10-12 |
| CA2737932C (en) | 2016-05-17 |
| US20110184183A1 (en) | 2011-07-28 |
| ZA201101855B (en) | 2012-05-30 |
| RS53150B (sr) | 2014-06-30 |
| MX2011004950A (es) | 2011-05-30 |
| RU2500676C2 (ru) | 2013-12-10 |
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