HRP20180530T1 - Polimorfi 3-(e)-2-(2-[6-(2-cijanofenoksi)pirimidin-4-iloksi]-fenil)-3-metoksiakrilata - Google Patents
Polimorfi 3-(e)-2-(2-[6-(2-cijanofenoksi)pirimidin-4-iloksi]-fenil)-3-metoksiakrilata Download PDFInfo
- Publication number
- HRP20180530T1 HRP20180530T1 HRP20180530TT HRP20180530T HRP20180530T1 HR P20180530 T1 HRP20180530 T1 HR P20180530T1 HR P20180530T T HRP20180530T T HR P20180530TT HR P20180530 T HRP20180530 T HR P20180530T HR P20180530 T1 HRP20180530 T1 HR P20180530T1
- Authority
- HR
- Croatia
- Prior art keywords
- methoxyacrylate
- cyanophenoxy
- yloxy
- phenyl
- polymorph
- Prior art date
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- 238000000034 method Methods 0.000 claims 12
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 7
- 239000013078 crystal Substances 0.000 claims 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 238000002955 isolation Methods 0.000 claims 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims 4
- 241000233866 Fungi Species 0.000 claims 3
- 238000001237 Raman spectrum Methods 0.000 claims 3
- 239000012296 anti-solvent Substances 0.000 claims 3
- 238000001228 spectrum Methods 0.000 claims 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000011877 solvent mixture Substances 0.000 claims 2
- 238000001757 thermogravimetry curve Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Claims (23)
1. Kristalni polimorfni oblik B metil (E)-2-{2-[6-(2-cijanofenoksi)pirimidin-4-iloksi]fenil}-3-metoksiakrilata, naznačen time da je karakteriziran sljedećim svojstvima:
a) polimorf pokazuje uzorak difrakcije rendgenskih zraka na prašku s karakterističnim vrhovima izraženima u stupnjevima 2θ (+/-0.20° θ) na oko 7,5, 11,75, 13,20 i 19,65; i po izboru
b) polimorf pokazuje infracrveni (IR) spektar s karakterističnim vrhovima na oko 1389, 1335 i 1245 cm-1.
2. Kristalni polimorf u skladu s patentnim zahtjevom 1, naznačen time, da polimorf pokazuje predominantnu endotermu u rasponu od oko 101 - 105° C izmjereno diferencijalnim skenirajućim kalorimetrom (DSC) pri brzini skeniranja od 10° C po minuti.
3. Kristalni polimorf u skladu s patentnim zahtjevom 1, naznačen time, da polimorf pokazuje Ramanov spektar s karakterističnim vrhovima na oko - 3098, 1335 i 2237 cm-1.
4. Kristalni polimorf u skladu s patentnim zahtjevom 1, naznačen time, da polimorf nadalje pokazuje karakteristične vrhove izraženima u stupnjevima 2 θ (+/-0.20° θ) na oko 14,15, 17,1 i 23,6.
5. Kristalni polimorf u skladu s patentnim zahtjevom 1, naznačen time, da polimorf pokazuje najmanje jednu od sljedećih karakteristika:
(a) uzorak difrakcije rendgenskih zraka na prašku, kao što je prikazano na slici 5;
(b) infracrveni (IR) spektar uglavnom kao što je prikazano na slici 6;
(c) termogram diferencijalnog skenirajućeg kalorimetra (DSC) uglavnom kao što je prikazano na slici 7;
(d) Raman spektar uglavnom kao što je prikazano na slici 8.
6. Smjesa polimorfnog oblika A i oblika B metil (E)-2-{2-[6-(2-cijanofenoksi)pirimidin -4-iloksi] fenil}- 3-metoksiakrilata, naznačena time, da je oblik A karakteriziran sljedećim svojstvima:
a) polimorf pokazuje uzorak difrakcije rendgenskih zraka na prahu s karakterističnim vrhovima izraženim u stupnjevima 2 θ (+/-0.20° θ) na oko 6,25, 13,8, 17,65, 19,05, 26,4 i 28,5; i po izboru
b) polimorf ima infracrveni (IR) spektar s karakterističnim vrhovima na oko 1378, 1328 i 1154 cm-1 i pri čemu je oblik B kako je definirano u bilo kojem od patentnih zahtjeva 1-5.
7. Smjesa u skladu s patentnim zahtjevom 6, naznačena time, da polimorfni oblik A pokazuje Raman spektar s karakterističnim vrhovima na oko 4398, 133029 i 22332 cm-1.
8. Smjesa u skladu s patentnim zahtjevom 6, naznačena time, da polimorfni oblik A pokazuje jedinu dominantnu endotermu u rasponu od oko 114 - 117° C izmjereno diferencijalnim skenirajućim kalorimetrom (DSC) pri brzini skeniranja od 10° C u minuti.
9. Smjesa u skladu s patentnim zahtjevom 6, naznačena time, da polimorfni oblik A nadalje pokazuje karakteristične vrhove rendgenske difrakcije na prahu izražene u stupnjevima 2θ (+/-0.20° θ) na oko 11 i 14,4.
10. Smjesa u skladu s patentnim zahtjevom 6, naznačena time, da je termogram diferencijalnog skenirajućeg kalorimetra (DSC) kao što je prikazano na slici 9.
11. Postupak za pripravu kristalnog polimorfnog oblika B metil (E)-2-{2-[6-(2-cijanofenoksi)pirimidin -4- iloksi] fenil}-3-metoksiakrilata u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačen time, da postupak obuhvaća korake kristalizacije spomenutog spoja iz smjese otapala koja sadržava vodu i organsko otapalo koje se bira iz skupine koju čine alkohol i amid.
12. Postupak u skladu s patentnim zahtjevom 11, naznačen time, da se organsko otapalo bira iz skupine koju čine 1-propanol i N,N-dimetilacetamid.
13. Postupak u skladu s patentnim zahtjevom 11, naznačen time, da obuhvaća korake:
a) pripremanje otopine metil (E)-2-{2-[6-(2-cijanofenoksi)pirimidin-4-iloksi]fenil}-3-metoksiakrilata u otapalu odabranom iz skupine koja sadržava alkohol i amid;
b) dodavanje vode navedenoj otopini tako da se dobiju kristali spomenutog spoja; i
c) izoliranje kristala.
14. Postupak za pripravu smjese kristalnog polimorfnog oblika A i oblika B metil (E)-2- {2- [6- (2- cijanofenoksi)pirimidin-4-iloksi]fenil}-3-metoksiakrilata u skladu s bilo kojim od patentnih zahtjeva 6 do 10, naznačen time, da postupak obuhvaća korake kristalizacije spomenutog spoja iz smjese otapala koja sadržava alkohol i anti-otapalo odabrano između alifatskog i aromatskog ugljikovodika; i izoliranje dobivenih kristala.
15. Postupak u skladu s patentnim zahtjevom 14, naznačen time, da je alkohol odabran iz skupine koju čine izopropil alkohol, 1-propanol i butanol.
16. Postupak u skladu s patentnim zahtjevom 14, naznačen time, da je anti-otapalo heptan.
17. Postupak u skladu s patentnim zahtjevom 14, naznačen time, da obuhvaća korake:
a) pripremanja otopine metil (E)-2-{2-[6-(2-cijanofenoksi)pirimidin-4-iloksi]fenil}-3-metoksiakrilata u alkoholu;
b) dodavanje anti-otapala odabranog između alifatskog i aromatskog ugljikovodika u navedenu otopinu tako da se dobiju kristali spomenutog spoja; i
c) izoliranje kristala.
18. Postupak za pripravu smjese kristalnog polimorfnog oblika A i oblika B metil (E)-2-{2- [6-(2-cijanofenoksi)pirimidin-4-iloksi]fenil}-3-metoksiakrilata u skladu s bilo kojim od patentnih zahtjeva 6 do 10, naznačen time, da postupak obuhvaća korake:
a) priređivanje otopine metil (E)-2-{2-[6-(2-cijanofenoksi)pirimidin-4-iloksi]fenil}3-metoksiakrilata u alkoholu;
b) brzo hlađenje otopine tako da se dobiju kristali spomenutog spoja; i
c) izoliranje kristala.
19. Postupak u skladu s patentnim zahtjevom 18, naznačen time, da je alkohol izopropil alkohol.
20. Pripravak, naznačen time, da sadržava kristalni polimorfni oblik B metil (E)-2-{2-[6-(2-cijanofenoksi) pirimidin-4-iloksi]fenil}-3-metoksiakrilata u skladu s bilo kojim od patentnih zahtjeva 1 do 5 i prihvatljivi adjuvans ili smjesu kristalnog polimorfnog oblika A i B metil (E)-2-{2-[6- (2-cijanofenoksi) pirimidin- 4-iloksi]fenil}-3-metoksiakrilata u skladu s bilo kojim od patentnih zahtjeva 6 do 10 i prihvatljivi adjuvans.
21. Pripravak u skladu s patentnim zahtjevom 20, naznačen time, da se koristi za suzbijanje gljivica.
22. Postupak za suzbijanje gljivica u biljci, naznačen time, da obuhvaća primjenu na biljku, sjeme biljke ili mjesto sjemena ili biljke fungicidno učinkovite količine pripravka iz zahtjeva 20.
23. Postupak za zaštitu usjeva od gljivica, naznačen time, da sadržava primjenu na usjeve učinkovite količine pripravka iz patentnog zahtjeva 20.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL181125A IL181125A0 (en) | 2007-02-01 | 2007-02-01 | Polymorphs of 3-(e)-2-{2-[6-(2- |
| PCT/IL2008/000063 WO2008093325A2 (en) | 2007-02-01 | 2008-01-16 | Polymorphs of 3-(e)-2-{2-[6-(2-cyanophenoxy) pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate |
| EP08702644.9A EP2129221B1 (en) | 2007-02-01 | 2008-01-16 | Polymorphs of 3-(e)-2-{2-[6-(2-cyanophenoxy) pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20180530T1 true HRP20180530T1 (hr) | 2018-05-04 |
Family
ID=39674584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20180530TT HRP20180530T1 (hr) | 2007-02-01 | 2018-03-29 | Polimorfi 3-(e)-2-(2-[6-(2-cijanofenoksi)pirimidin-4-iloksi]-fenil)-3-metoksiakrilata |
Country Status (25)
| Country | Link |
|---|---|
| US (4) | US8546411B2 (hr) |
| EP (1) | EP2129221B1 (hr) |
| JP (1) | JP2010517995A (hr) |
| KR (1) | KR20090106621A (hr) |
| CN (2) | CN103012285A (hr) |
| AU (1) | AU2008211532C1 (hr) |
| BR (1) | BRPI0806410A8 (hr) |
| CA (2) | CA3147003A1 (hr) |
| CO (1) | CO6220913A2 (hr) |
| CY (1) | CY1120106T1 (hr) |
| DK (1) | DK2129221T3 (hr) |
| EC (1) | ECSP099555A (hr) |
| ES (1) | ES2664416T3 (hr) |
| HR (1) | HRP20180530T1 (hr) |
| HU (1) | HUE036753T2 (hr) |
| IL (2) | IL181125A0 (hr) |
| LT (1) | LT2129221T (hr) |
| MX (2) | MX2020005034A (hr) |
| NO (1) | NO2129221T3 (hr) |
| NZ (3) | NZ604923A (hr) |
| PL (1) | PL2129221T3 (hr) |
| PT (1) | PT2129221T (hr) |
| SI (1) | SI2129221T1 (hr) |
| WO (1) | WO2008093325A2 (hr) |
| ZA (1) | ZA200905119B (hr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL180134A0 (en) | 2006-12-17 | 2007-07-04 | David Ovadia | Process for the preparation of substituted cyanophenoxy-pyrimidinyloxy -phenyl acrylate derivatives |
| IL181125A0 (en) * | 2007-02-01 | 2007-07-04 | Maktheshim Chemical Works Ltd | Polymorphs of 3-(e)-2-{2-[6-(2- |
| EP2540709B1 (en) * | 2010-02-23 | 2014-08-20 | Nippon Kayaku Co., Ltd. | Stable crystal form of 2-ethyl-3, 7-dimethyl-6-(4-(trifluoromethoxy) phenoxy)quinoline-4-ylmethyl carbonate, method of manufacturing same and agricultural chemical composition containing crystals of same |
| CN111094252B (zh) | 2017-07-17 | 2024-05-24 | 阿达玛克西姆股份有限公司 | 5-氟-4-亚氨基-3-甲基-1-甲苯磺酰基-3,4-二氢嘧啶-2-酮的多晶型物 |
| CN109384728A (zh) * | 2017-08-07 | 2019-02-26 | 华东理工大学 | 嘧菌酯通道型溶剂化物及其制备方法 |
| CN108675963B (zh) * | 2018-06-06 | 2021-07-13 | 天津大学 | 嘧菌酯1，4二氧六环溶剂化物及制备方法 |
| CN108947915B (zh) * | 2018-06-06 | 2021-07-06 | 天津大学 | 嘧菌酯丙酮溶剂化物及制备方法 |
| CN108947914B (zh) * | 2018-06-06 | 2021-07-23 | 天津大学 | 嘧菌酯乙酸溶剂化物及制备方法 |
| CN114660045A (zh) * | 2022-04-25 | 2022-06-24 | 贵阳市花溪区农业农村局 | 一种利用表面增强拉曼光谱快速检测草莓中嘧菌酯的方法及应用 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0391451A1 (en) | 1986-04-17 | 1990-10-10 | Imperial Chemical Industries Plc | Fungicides |
| US5160530A (en) * | 1989-01-24 | 1992-11-03 | Griffin Corporation | Microencapsulated polymorphic agriculturally active material |
| US5145856A (en) * | 1989-02-10 | 1992-09-08 | Imperial Chemical Industries Plc | Fungicides |
| US5264440A (en) * | 1989-02-10 | 1993-11-23 | Imperial Chemical Industries Plc | Fungicides |
| GB8903019D0 (en) * | 1989-02-10 | 1989-03-30 | Ici Plc | Fungicides |
| IE74711B1 (en) * | 1990-07-27 | 1997-07-30 | Ici Plc | Fungicides |
| GB9122430D0 (en) * | 1990-11-16 | 1991-12-04 | Ici Plc | Chemical process |
| US5760250A (en) * | 1991-11-05 | 1998-06-02 | Zeneca Limited | Process for the preparation of 3-(α-methoxy)methylenebenzofuranones and intermediates therefor |
| IN179039B (hr) | 1994-02-08 | 1997-08-09 | Rallis India Ltd | |
| IL122715A (en) | 1995-06-28 | 2000-11-21 | Zeneca Ltd | Process for the preparation of 2-(6-substituted-pyrid-2-yloxymethyl)phenylacetates useful as intermediates for producing fungicides |
| DE19605901A1 (de) * | 1996-02-17 | 1997-08-21 | Basf Ag | Verfahren zur Herstellung von 2-(2-Methylphenyl)-3-methoxyacrylsäure -methylester |
| GB9617351D0 (en) * | 1996-08-19 | 1996-10-02 | Zeneca Ltd | Chemical process |
| GB9622345D0 (en) * | 1996-10-28 | 1997-01-08 | Zeneca Ltd | Chemical process |
| JP2000263183A (ja) * | 1999-03-17 | 2000-09-26 | Pop Rivet Fastener Kk | 締結工具の破断片回収装置 |
| US20020042514A1 (en) * | 2000-06-26 | 2002-04-11 | Doyle Timothy John | Synthesis of chlorinated pyrimidines |
| GB0114408D0 (en) * | 2001-06-13 | 2001-08-08 | Syngenta Ltd | Chemical process |
| DE10351087A1 (de) * | 2003-10-31 | 2005-05-25 | Bayer Technology Services Gmbh | Feste Wirkstoff-Formulierung |
| GB0508422D0 (en) | 2005-04-26 | 2005-06-01 | Syngenta Ltd | Chemical process |
| GB0619941D0 (en) * | 2006-10-09 | 2006-11-15 | Syngenta Ltd | Chemical process |
| GB0619942D0 (en) | 2006-10-09 | 2006-11-15 | Syngenta Ltd | Chemical process |
| IL180134A0 (en) | 2006-12-17 | 2007-07-04 | David Ovadia | Process for the preparation of substituted cyanophenoxy-pyrimidinyloxy -phenyl acrylate derivatives |
| IL181125A0 (en) * | 2007-02-01 | 2007-07-04 | Maktheshim Chemical Works Ltd | Polymorphs of 3-(e)-2-{2-[6-(2- |
| CN100564362C (zh) * | 2007-10-24 | 2009-12-02 | 北京颖泰嘉和科技股份有限公司 | 嘧菌酯及其类似物的制备方法 |
| US8777767B2 (en) * | 2012-01-05 | 2014-07-15 | Suncast Technologies, Llc | Hybrid play set |
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2007
- 2007-02-01 IL IL181125A patent/IL181125A0/en unknown
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2008
- 2008-01-16 HU HUE08702644A patent/HUE036753T2/hu unknown
- 2008-01-16 PT PT87026449T patent/PT2129221T/pt unknown
- 2008-01-16 MX MX2020005034A patent/MX2020005034A/es unknown
- 2008-01-16 AU AU2008211532A patent/AU2008211532C1/en active Active
- 2008-01-16 CN CN2012103833361A patent/CN103012285A/zh active Pending
- 2008-01-16 LT LTEP08702644.9T patent/LT2129221T/lt unknown
- 2008-01-16 DK DK08702644.9T patent/DK2129221T3/en active
- 2008-01-16 BR BRPI0806410A patent/BRPI0806410A8/pt not_active Application Discontinuation
- 2008-01-16 CN CN200880003663A patent/CN101621926A/zh active Pending
- 2008-01-16 CA CA3147003A patent/CA3147003A1/en active Pending
- 2008-01-16 NZ NZ604923A patent/NZ604923A/en not_active IP Right Cessation
- 2008-01-16 NZ NZ578632A patent/NZ578632A/en not_active IP Right Cessation
- 2008-01-16 NZ NZ596178A patent/NZ596178A/xx not_active IP Right Cessation
- 2008-01-16 CA CA002677058A patent/CA2677058A1/en not_active Abandoned
- 2008-01-16 WO PCT/IL2008/000063 patent/WO2008093325A2/en active Application Filing
- 2008-01-16 KR KR1020097017457A patent/KR20090106621A/ko not_active Application Discontinuation
- 2008-01-16 NO NO08702644A patent/NO2129221T3/no unknown
- 2008-01-16 MX MX2009008138A patent/MX2009008138A/es not_active Application Discontinuation
- 2008-01-16 ES ES08702644.9T patent/ES2664416T3/es active Active
- 2008-01-16 EP EP08702644.9A patent/EP2129221B1/en active Active
- 2008-01-16 SI SI200831941T patent/SI2129221T1/en unknown
- 2008-01-16 JP JP2009547809A patent/JP2010517995A/ja active Pending
- 2008-01-16 PL PL08702644T patent/PL2129221T3/pl unknown
- 2008-08-07 US US12/525,362 patent/US8546411B2/en active Active
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2009
- 2009-07-22 ZA ZA200905119A patent/ZA200905119B/xx unknown
- 2009-07-26 IL IL200062A patent/IL200062A0/en unknown
- 2009-08-03 EC EC2009009555A patent/ECSP099555A/es unknown
- 2009-08-11 CO CO09083638A patent/CO6220913A2/es not_active Application Discontinuation
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2012
- 2012-12-06 US US13/706,438 patent/US8524723B2/en active Active
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2013
- 2013-07-31 US US13/955,459 patent/US8877767B2/en active Active
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2014
- 2014-10-30 US US14/527,881 patent/US20150057152A1/en not_active Abandoned
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2018
- 2018-03-27 CY CY20181100351T patent/CY1120106T1/el unknown
- 2018-03-29 HR HRP20180530TT patent/HRP20180530T1/hr unknown
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