JP2008528625A - アリールピロリドン類の合成 - Google Patents
アリールピロリドン類の合成 Download PDFInfo
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- JP2008528625A JP2008528625A JP2007553329A JP2007553329A JP2008528625A JP 2008528625 A JP2008528625 A JP 2008528625A JP 2007553329 A JP2007553329 A JP 2007553329A JP 2007553329 A JP2007553329 A JP 2007553329A JP 2008528625 A JP2008528625 A JP 2008528625A
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- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- aryl
- heteroaryl
- alkyl
- 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.)
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- 238000003786 synthesis reaction Methods 0.000 title description 12
- 230000015572 biosynthetic process Effects 0.000 title description 11
- 238000000034 method Methods 0.000 claims abstract description 67
- 125000003118 aryl group Chemical group 0.000 claims description 106
- 125000000217 alkyl group Chemical group 0.000 claims description 98
- 125000001072 heteroaryl group Chemical group 0.000 claims description 81
- -1 R 42 Chemical compound 0.000 claims description 60
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 59
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 57
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 30
- 150000001408 amides Chemical class 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000003446 ligand Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 150000003951 lactams Chemical class 0.000 claims description 10
- 125000002524 organometallic group Chemical group 0.000 claims description 9
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 238000004440 column chromatography Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 4
- 238000006254 arylation reaction Methods 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 150000003003 phosphines Chemical class 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 31
- 125000001424 substituent group Chemical group 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 19
- 229910052739 hydrogen Inorganic materials 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000011914 asymmetric synthesis Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 7
- 0 *C(C(*)=C1*)N(*)C1=O Chemical compound *C(C(*)=C1*)N(*)C1=O 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
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- 229910052760 oxygen Inorganic materials 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
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- 102100034343 Integrase Human genes 0.000 description 4
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- 239000012267 brine Substances 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 125000004474 heteroalkylene group Chemical group 0.000 description 4
- 239000002777 nucleoside Substances 0.000 description 4
- 150000003833 nucleoside derivatives Chemical class 0.000 description 4
- 102000004196 processed proteins & peptides Human genes 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000037357 HIV infectious disease Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
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- 230000000694 effects Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
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- JRPUSZCLMSDXAG-AWEZNQCLSA-N (4r)-4-(4-chloro-3-phenylmethoxyphenyl)pyrrolidin-2-one Chemical compound ClC1=CC=C([C@H]2CC(=O)NC2)C=C1OCC1=CC=CC=C1 JRPUSZCLMSDXAG-AWEZNQCLSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OOVXGFXJCWSMOY-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2h-pyrrol-5-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)C=CC1 OOVXGFXJCWSMOY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
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- 150000001413 amino acids Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
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- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64803905P | 2005-01-28 | 2005-01-28 | |
| PCT/US2006/003240 WO2006081562A2 (en) | 2005-01-28 | 2006-01-30 | Synthesis of aryl pyrrolidones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008528625A true JP2008528625A (ja) | 2008-07-31 |
| JP2008528625A5 JP2008528625A5 (https=) | 2009-03-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007553329A Pending JP2008528625A (ja) | 2005-01-28 | 2006-01-30 | アリールピロリドン類の合成 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1841424A4 (https=) |
| JP (1) | JP2008528625A (https=) |
| KR (1) | KR100890696B1 (https=) |
| CN (1) | CN101111246A (https=) |
| AU (1) | AU2006209241B2 (https=) |
| BR (1) | BRPI0607294A2 (https=) |
| CA (1) | CA2593816A1 (https=) |
| MX (1) | MX2007008974A (https=) |
| RU (1) | RU2007132260A (https=) |
| WO (1) | WO2006081562A2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2023544404A (ja) * | 2020-10-06 | 2023-10-23 | ディー．イー．ショウ リサーチ，エルエルシー | Ｋｖ１．３カリウムＳＨＡＫＥＲチャネル遮断剤としてのラクタム化合物 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2799154A1 (en) | 2010-05-12 | 2011-11-17 | Abbvie Inc. | Indazole inhibitors of kinase |
| CN101979378B (zh) * | 2010-10-13 | 2012-06-27 | 中国科学院上海有机化学研究所 | 一种手性γ-内酰胺化合物的合成方法 |
| RU2485100C1 (ru) * | 2012-02-07 | 2013-06-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Пермский государственный национальный исследовательский университет" | 1-арил-4-бензоил-3-гидрокси-5-метоксикарбонил-2,5-дигидро-1н-пиррол-2-оны, проявляющие анальгетическую активность, и способ их получения |
| US11589583B2 (en) | 2013-12-03 | 2023-02-28 | Fmc Corporation | Pyrrolidinones herbicides |
| CA2931961C (en) | 2013-12-03 | 2023-10-31 | Andrew Duncan Satterfield | Pyrrolidinones as herbicides |
| SG11201610720VA (en) | 2014-07-02 | 2017-01-27 | Du Pont | Piperidinone herbicides |
| CN107001260B (zh) | 2014-12-08 | 2020-11-10 | Fmc公司 | 3-氧基-3-(芳氨基)丙酸酯、其制备方法、以及其在制备吡咯烷酮中的用途 |
| EP3280709B1 (en) | 2015-04-10 | 2021-05-26 | FMC Corporation | Substituted cyclic amides as herbicides |
| BR112017020094B1 (pt) | 2015-04-27 | 2022-01-11 | Fmc Corporation | Composto, composições herbicidas, mistura de herbicida e método para controlar o crescimento de vegetação indesejada |
| JP7000160B2 (ja) | 2015-05-12 | 2022-01-19 | エフ エム シー コーポレーション | 除草剤としてのアリール置換二環式化合物 |
| JP6869192B2 (ja) | 2015-05-29 | 2021-05-12 | エフ エム シー コーポレーションＦｍｃ Ｃｏｒｐｏｒａｔｉｏｎ | 除草剤としての置換環状アミド |
| CN107709310B (zh) | 2015-06-02 | 2021-09-24 | Fmc公司 | 取代的环酰胺及其作为除草剂的用途 |
| JP6937290B2 (ja) | 2015-07-31 | 2021-09-22 | エフ エム シー コーポレーションＦｍｃ Ｃｏｒｐｏｒａｔｉｏｎ | 除草剤として有用な環状ｎ−カルボキサミド化合物 |
| RU2019122791A (ru) | 2016-12-21 | 2021-01-25 | Фмк Корпорейшн | Гербициды на основе нитрона |
| CN110740646B (zh) | 2017-03-21 | 2022-05-10 | Fmc公司 | 除草剂混合物、组合物和方法 |
| MX2019010969A (es) | 2017-03-21 | 2019-12-02 | Fmc Corp | Pirrolidinonas y proceso para prepararlas. |
| AR111839A1 (es) | 2017-05-30 | 2019-08-21 | Fmc Corp | Lactamas 3-sustituidas herbicidas |
| AR111967A1 (es) | 2017-05-30 | 2019-09-04 | Fmc Corp | Amidas herbicidas |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2002363160A (ja) * | 2001-06-05 | 2002-12-18 | Sumitomo Chem Co Ltd | 光学活性４−アリール−２−ピペリジノン類の製造方法 |
| WO2004037784A2 (en) * | 2002-10-21 | 2004-05-06 | Irm Llc | Pyrrolidones with anti-hiv activity |
| JP2004315396A (ja) * | 2003-04-14 | 2004-11-11 | Mitsubishi Rayon Co Ltd | 光学活性β−アリ−ル化合物の製造法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3058986A (en) * | 1962-10-16 | N-ammoalkyl-x-phenyl-x-lower alkyl-z- | ||
| US3956314A (en) * | 1970-07-24 | 1976-05-11 | U.C.B., Societe Anonyme | Derivatives of 2-pyrrolidinone |
| US3956914A (en) * | 1974-11-14 | 1976-05-18 | The Marison Company | Spin lathe |
| WO2006081554A2 (en) * | 2005-01-28 | 2006-08-03 | Irm Llc | Phenyl-substituted pyrrolidones |
-
2006
- 2006-01-30 MX MX2007008974A patent/MX2007008974A/es not_active Application Discontinuation
- 2006-01-30 CA CA002593816A patent/CA2593816A1/en not_active Abandoned
- 2006-01-30 WO PCT/US2006/003240 patent/WO2006081562A2/en not_active Ceased
- 2006-01-30 BR BRPI0607294-1A patent/BRPI0607294A2/pt not_active IP Right Cessation
- 2006-01-30 KR KR1020077017460A patent/KR100890696B1/ko not_active Expired - Fee Related
- 2006-01-30 EP EP06719887A patent/EP1841424A4/en not_active Withdrawn
- 2006-01-30 RU RU2007132260/04A patent/RU2007132260A/ru not_active Application Discontinuation
- 2006-01-30 AU AU2006209241A patent/AU2006209241B2/en not_active Expired - Fee Related
- 2006-01-30 JP JP2007553329A patent/JP2008528625A/ja active Pending
- 2006-01-30 CN CNA2006800035536A patent/CN101111246A/zh active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002363160A (ja) * | 2001-06-05 | 2002-12-18 | Sumitomo Chem Co Ltd | 光学活性４−アリール−２−ピペリジノン類の製造方法 |
| WO2004037784A2 (en) * | 2002-10-21 | 2004-05-06 | Irm Llc | Pyrrolidones with anti-hiv activity |
| JP2004315396A (ja) * | 2003-04-14 | 2004-11-11 | Mitsubishi Rayon Co Ltd | 光学活性β−アリ−ル化合物の製造法 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2023544404A (ja) * | 2020-10-06 | 2023-10-23 | ディー．イー．ショウ リサーチ，エルエルシー | Ｋｖ１．３カリウムＳＨＡＫＥＲチャネル遮断剤としてのラクタム化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006081562A3 (en) | 2006-10-19 |
| EP1841424A2 (en) | 2007-10-10 |
| KR20070097555A (ko) | 2007-10-04 |
| CA2593816A1 (en) | 2006-08-03 |
| BRPI0607294A2 (pt) | 2009-08-25 |
| AU2006209241A1 (en) | 2006-08-03 |
| EP1841424A4 (en) | 2010-01-27 |
| WO2006081562A2 (en) | 2006-08-03 |
| AU2006209241B2 (en) | 2009-10-22 |
| RU2007132260A (ru) | 2009-03-10 |
| KR100890696B1 (ko) | 2009-03-26 |
| MX2007008974A (es) | 2007-09-18 |
| CN101111246A (zh) | 2008-01-23 |
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