ZA200701997B - A process for the preparation of [1,4,5]-oxadiazepine derivatives - Google Patents
A process for the preparation of [1,4,5]-oxadiazepine derivatives Download PDFInfo
- Publication number
- ZA200701997B ZA200701997B ZA200701997A ZA200701997A ZA200701997B ZA 200701997 B ZA200701997 B ZA 200701997B ZA 200701997 A ZA200701997 A ZA 200701997A ZA 200701997 A ZA200701997 A ZA 200701997A ZA 200701997 B ZA200701997 B ZA 200701997B
- Authority
- ZA
- South Africa
- Prior art keywords
- oxadiazepine
- preparation
- reaction
- water
- reaction mixture
- Prior art date
Links
- NNHCFSLBNPIGQO-UHFFFAOYSA-N 1,4,5-oxadiazepine Chemical class O1C=CN=NC=C1 NNHCFSLBNPIGQO-UHFFFAOYSA-N 0.000 title claims description 35
- 238000002360 preparation method Methods 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000002585 base Substances 0.000 claims description 12
- 239000002798 polar solvent Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 230000002363 herbicidal effect Effects 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 35
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000000203 mixture Substances 0.000 description 12
- 238000000605 extraction Methods 0.000 description 11
- -1 alkyiphenyl Chemical group 0.000 description 10
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 10
- SOFONLLYTIGLKK-UHFFFAOYSA-N 1-(5-acetyl-1,4,5-oxadiazepin-4-yl)ethanone Chemical compound CC(=O)N1C=COC=CN1C(C)=O SOFONLLYTIGLKK-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 7
- ZLHNYIHIHQEHJQ-UHFFFAOYSA-N N,N'-Diacetylhydrazine Chemical compound CC(=O)NNC(C)=O ZLHNYIHIHQEHJQ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 150000002429 hydrazines Chemical class 0.000 description 5
- 235000011056 potassium acetate Nutrition 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 3
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- PYBGPZHUDRSYHA-UHFFFAOYSA-N 1,3,5-oxadiazepine Chemical compound O1C=CN=CN=C1 PYBGPZHUDRSYHA-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000006307 alkoxy benzyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000006177 alkyl benzyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000006277 halobenzyl group Chemical group 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/06—Seven-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH17762004 | 2004-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200701997B true ZA200701997B (en) | 2008-07-30 |
Family
ID=35708855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200701997A ZA200701997B (en) | 2004-10-27 | 2007-03-07 | A process for the preparation of [1,4,5]-oxadiazepine derivatives |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US20090124800A1 (enExample) |
| EP (1) | EP1838683B1 (enExample) |
| JP (1) | JP5117858B2 (enExample) |
| KR (1) | KR101317353B1 (enExample) |
| CN (2) | CN101039926B (enExample) |
| AR (1) | AR051341A1 (enExample) |
| AT (1) | ATE430140T1 (enExample) |
| BR (1) | BRPI0517390B8 (enExample) |
| CA (1) | CA2579742C (enExample) |
| DE (1) | DE602005014280D1 (enExample) |
| DK (1) | DK1838683T3 (enExample) |
| EA (1) | EA011555B1 (enExample) |
| ES (1) | ES2325382T3 (enExample) |
| IL (1) | IL181766A (enExample) |
| MX (1) | MX2007004591A (enExample) |
| PT (1) | PT1838683E (enExample) |
| TW (1) | TWI382021B (enExample) |
| UA (1) | UA87710C2 (enExample) |
| WO (1) | WO2006045587A1 (enExample) |
| ZA (1) | ZA200701997B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI316939B (en) * | 2001-12-18 | 2009-11-11 | Syngenta Participations Ag | Process for the preparation of organic compounds |
| AR087008A1 (es) | 2011-06-22 | 2014-02-05 | Syngenta Participations Ag | Derivados de n-oxi-pirazolo-triazepina-diona |
| CN104974106B (zh) * | 2014-04-04 | 2019-02-22 | 浙江普洛康裕制药有限公司 | 5-烷基-[1,3,4]-噁二唑-2-甲酸烷基酯的合成方法 |
| CN108264493B (zh) * | 2016-12-30 | 2022-09-30 | 泸州东方农化有限公司 | 一种制备氧二氮杂环化合物的工艺及其应用 |
| WO2018120093A1 (zh) * | 2016-12-30 | 2018-07-05 | 泸州东方农化有限公司 | 一种制备氧二氮杂环化合物的工艺及其应用 |
| CN108264492B (zh) * | 2016-12-30 | 2020-04-14 | 浙江省诸暨合力化学对外贸易有限公司 | 一种氧二氮杂环化合物的制备工艺及应用 |
| CN111386274B (zh) | 2017-12-05 | 2023-07-21 | 先正达参股股份有限公司 | 用于合成除草剂吡唑烷二酮化合物的化学方法 |
| CN112522340B (zh) * | 2019-09-19 | 2023-05-09 | 四川利尔生物科技有限公司 | 酶催化水解制备1-氧-4,5-二氮杂环庚烷的方法 |
| GB202206290D0 (en) * | 2022-04-29 | 2022-06-15 | Syngenta Crop Protection Ag | Process |
| CN119118946A (zh) * | 2023-06-13 | 2024-12-13 | 南京理工大学 | 一种安全高效制备[1,4,5]氧二氮杂庚烷的方法 |
| WO2025131957A1 (en) | 2023-12-22 | 2025-06-26 | Basf Se | Diazinone compounds for the control of invertebrate pests |
| EP4574819A1 (en) | 2023-12-22 | 2025-06-25 | Basf Se | Diazinone compounds for the control of invertebrate pests |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2921068A (en) * | 1957-11-19 | 1960-01-12 | Sterling Drug Inc | Mercurated 1, 6-diazabicyclo[4, 4, o] decane-7, 10-diones |
| JPH1029981A (ja) * | 1996-07-15 | 1998-02-03 | Nippon Hidorajin Kogyo Kk | ヘキサヒドロピリダジン類の製造方法 |
| AU741365B2 (en) * | 1998-03-13 | 2001-11-29 | Syngenta Participations Ag | Herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline derivatives |
| PT1209972E (pt) * | 1999-09-07 | 2003-10-31 | Syngenta Participations Ag | Composicao herbicida |
| CA2382432A1 (en) * | 1999-09-07 | 2001-03-15 | Thomas Maetzke | Novel herbicides |
| TWI316939B (en) * | 2001-12-18 | 2009-11-11 | Syngenta Participations Ag | Process for the preparation of organic compounds |
-
2005
- 2005-10-25 BR BRPI0517390A patent/BRPI0517390B8/pt active IP Right Grant
- 2005-10-25 UA UAA200705420A patent/UA87710C2/ru unknown
- 2005-10-25 TW TW094137257A patent/TWI382021B/zh active
- 2005-10-25 DK DK05795620T patent/DK1838683T3/da active
- 2005-10-25 MX MX2007004591A patent/MX2007004591A/es active IP Right Grant
- 2005-10-25 EP EP05795620A patent/EP1838683B1/en not_active Expired - Lifetime
- 2005-10-25 CN CN2005800347444A patent/CN101039926B/zh not_active Expired - Lifetime
- 2005-10-25 EA EA200700766A patent/EA011555B1/ru not_active IP Right Cessation
- 2005-10-25 ES ES05795620T patent/ES2325382T3/es not_active Expired - Lifetime
- 2005-10-25 PT PT05795620T patent/PT1838683E/pt unknown
- 2005-10-25 DE DE602005014280T patent/DE602005014280D1/de not_active Expired - Lifetime
- 2005-10-25 WO PCT/EP2005/011432 patent/WO2006045587A1/en not_active Ceased
- 2005-10-25 US US11/577,805 patent/US20090124800A1/en not_active Abandoned
- 2005-10-25 AR ARP050104463A patent/AR051341A1/es active IP Right Grant
- 2005-10-25 CN CN2010102611497A patent/CN101914072A/zh active Pending
- 2005-10-25 KR KR1020077009539A patent/KR101317353B1/ko not_active Expired - Lifetime
- 2005-10-25 AT AT05795620T patent/ATE430140T1/de active
- 2005-10-25 CA CA2579742A patent/CA2579742C/en not_active Expired - Lifetime
- 2005-10-25 JP JP2007538323A patent/JP5117858B2/ja not_active Expired - Lifetime
-
2007
- 2007-03-07 IL IL181766A patent/IL181766A/en active IP Right Grant
- 2007-03-07 ZA ZA200701997A patent/ZA200701997B/en unknown
-
2011
- 2011-05-04 US US13/100,601 patent/US20110207925A1/en not_active Abandoned
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