CA2593816A1 - Synthesis of aryl pyrrolidones - Google Patents
Synthesis of aryl pyrrolidones Download PDFInfo
- Publication number
- CA2593816A1 CA2593816A1 CA002593816A CA2593816A CA2593816A1 CA 2593816 A1 CA2593816 A1 CA 2593816A1 CA 002593816 A CA002593816 A CA 002593816A CA 2593816 A CA2593816 A CA 2593816A CA 2593816 A1 CA2593816 A1 CA 2593816A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- unsubstituted
- aryl
- member selected
- 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.)
- Abandoned
Links
- -1 aryl pyrrolidones Chemical class 0.000 title claims abstract description 71
- 230000015572 biosynthetic process Effects 0.000 title description 13
- 238000003786 synthesis reaction Methods 0.000 title description 13
- 238000000034 method Methods 0.000 claims abstract description 67
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims description 104
- 125000000217 alkyl group Chemical group 0.000 claims description 98
- 125000001072 heteroaryl group Chemical group 0.000 claims description 81
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 58
- 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 48
- 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000003446 ligand Substances 0.000 claims description 13
- 125000004429 atom Chemical group 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
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000002524 organometallic group Chemical group 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 238000011084 recovery Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 5
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 4
- 238000001953 recrystallisation 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
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
- 239000000047 product Substances 0.000 description 31
- 125000001424 substituent group Chemical group 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000011914 asymmetric synthesis Methods 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000004474 heteroalkylene group Chemical group 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
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- 102100034343 Integrase Human genes 0.000 description 4
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 4
- 125000005647 linker 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
- 239000010948 rhodium Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 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
- 239000013522 chelant Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000000524 functional group Chemical group 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
- 229940037201 oris Drugs 0.000 description 3
- 150000004040 pyrrolidinones Chemical class 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 230000008685 targeting Effects 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001413 amino acids Chemical group 0.000 description 2
- HKVFISRIUUGTIB-UHFFFAOYSA-O azanium;cerium;nitrate Chemical compound [NH4+].[Ce].[O-][N+]([O-])=O HKVFISRIUUGTIB-UHFFFAOYSA-O 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 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
- 201000010099 disease Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
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- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
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- ZCYVEMRRCGMTRW-YPZZEJLDSA-N iodine-125 Chemical compound [125I] ZCYVEMRRCGMTRW-YPZZEJLDSA-N 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
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- GSJQKBJLCDSPCL-IBGZPJMESA-N (4r)-4-(4-chloro-3-phenylmethoxyphenyl)-1-(4-methoxyphenyl)pyrrolidin-2-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)C[C@H](C=2C=C(OCC=3C=CC=CC=3)C(Cl)=CC=2)C1 GSJQKBJLCDSPCL-IBGZPJMESA-N 0.000 description 1
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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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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| US60/648,039 | 2005-01-28 | ||
| PCT/US2006/003240 WO2006081562A2 (en) | 2005-01-28 | 2006-01-30 | Synthesis of aryl pyrrolidones |
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| CA2593816A1 true CA2593816A1 (en) | 2006-08-03 |
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| CA002593816A Abandoned CA2593816A1 (en) | 2005-01-28 | 2006-01-30 | Synthesis of aryl pyrrolidones |
Country Status (10)
| Country | Link |
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| 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=) |
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| MX2012013197A (es) | 2010-05-12 | 2013-04-03 | Abbvie Inc | Inhibidores de indazol de cinasa. |
| 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 |
| MX2016007259A (es) | 2013-12-03 | 2016-08-04 | Du Pont | Pirrolidinonas como herbicidas. |
| US9944602B2 (en) | 2014-07-02 | 2018-04-17 | E. I. Du Pont De Nemours And Company | Piperidinone herbicides |
| EP3230264B1 (en) | 2014-12-08 | 2019-09-11 | FMC Corporation | 3-oxo-3-(arylamino)propanoates, a process for their preparation, and their use in preparing pyrrolidinones |
| EP3280709B1 (en) | 2015-04-10 | 2021-05-26 | FMC Corporation | Substituted cyclic amides as herbicides |
| CN107531658B (zh) | 2015-04-27 | 2021-07-27 | Fmc公司 | 作为除草剂的丁内酯 |
| PL3294743T3 (pl) | 2015-05-12 | 2020-03-31 | Fmc Corporation | Podstawione arylem związki bicykliczne jako środki chwastobójcze |
| WO2016196019A1 (en) | 2015-05-29 | 2016-12-08 | E I Du Pont De Nemours And Company | Substituted cyclic amides as herbicides |
| 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 |
| CN108137512B (zh) | 2015-07-31 | 2022-05-31 | Fmc公司 | 用作除草剂的环状n-酰胺化合物 |
| CA3047724A1 (en) | 2016-12-21 | 2018-06-28 | Fmc Corporation | Nitrone herbicides |
| WO2018175231A1 (en) | 2017-03-21 | 2018-09-27 | Fmc Corporation | Herbicidal mixture, composition and method |
| CA3057297A1 (en) | 2017-03-21 | 2018-09-27 | Fmc Corporation | Pyrrolidinones and a process to prepare them |
| 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 |
| MX2023003841A (es) * | 2020-10-06 | 2023-06-23 | De Shaw Res Llc | Compuestos lactámicos como bloqueadores del canal agitador de potasio kv1.3. |
Family Cites Families (7)
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|---|---|---|---|---|
| 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 |
| 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 |
| AU2003285952A1 (en) * | 2002-10-21 | 2004-05-13 | Irm Llc | Pyrrolidones with anti-hiv activity |
| JP4351859B2 (ja) * | 2003-04-14 | 2009-10-28 | 三菱レイヨン株式会社 | 光学活性β−アリ−ル化合物の製造法 |
| KR20090028846A (ko) * | 2005-01-28 | 2009-03-19 | 아이알엠 엘엘씨 | 페닐-치환 피롤리돈 |
-
2006
- 2006-01-30 JP JP2007553329A patent/JP2008528625A/ja active Pending
- 2006-01-30 CA CA002593816A patent/CA2593816A1/en not_active Abandoned
- 2006-01-30 KR KR1020077017460A patent/KR100890696B1/ko not_active Expired - Fee Related
- 2006-01-30 AU AU2006209241A patent/AU2006209241B2/en not_active Expired - Fee Related
- 2006-01-30 CN CNA2006800035536A patent/CN101111246A/zh active Pending
- 2006-01-30 WO PCT/US2006/003240 patent/WO2006081562A2/en not_active Ceased
- 2006-01-30 RU RU2007132260/04A patent/RU2007132260A/ru not_active Application Discontinuation
- 2006-01-30 BR BRPI0607294-1A patent/BRPI0607294A2/pt not_active IP Right Cessation
- 2006-01-30 EP EP06719887A patent/EP1841424A4/en not_active Withdrawn
- 2006-01-30 MX MX2007008974A patent/MX2007008974A/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006081562A3 (en) | 2006-10-19 |
| KR20070097555A (ko) | 2007-10-04 |
| CN101111246A (zh) | 2008-01-23 |
| JP2008528625A (ja) | 2008-07-31 |
| WO2006081562A2 (en) | 2006-08-03 |
| AU2006209241A1 (en) | 2006-08-03 |
| AU2006209241B2 (en) | 2009-10-22 |
| EP1841424A2 (en) | 2007-10-10 |
| MX2007008974A (es) | 2007-09-18 |
| RU2007132260A (ru) | 2009-03-10 |
| BRPI0607294A2 (pt) | 2009-08-25 |
| EP1841424A4 (en) | 2010-01-27 |
| KR100890696B1 (ko) | 2009-03-26 |
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