MD4150C1 - Procedeu de obţinere a compuşilor coordinativi ai Co(II), Ni(II) şi Zn(II) cu 2-nitro-4,5-difenilimidazol pornind de la 4,5-difenilimidazol şi nitraţii metalelor respective - Google Patents
Procedeu de obţinere a compuşilor coordinativi ai Co(II), Ni(II) şi Zn(II) cu 2-nitro-4,5-difenilimidazol pornind de la 4,5-difenilimidazol şi nitraţii metalelor respective Download PDFInfo
- Publication number
- MD4150C1 MD4150C1 MDA20110087A MD20110087A MD4150C1 MD 4150 C1 MD4150 C1 MD 4150C1 MD A20110087 A MDA20110087 A MD A20110087A MD 20110087 A MD20110087 A MD 20110087A MD 4150 C1 MD4150 C1 MD 4150C1
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- MD
- Moldova
- Prior art keywords
- diphenylimidazole
- nitro
- compounds
- nitration
- nitrates
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 28
- CPHGOBGXZQKCKI-UHFFFAOYSA-N 4,5-diphenyl-1h-imidazole Chemical compound N1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CPHGOBGXZQKCKI-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 18
- 230000008569 process Effects 0.000 title claims abstract description 10
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 title claims abstract description 9
- STGHAEAHYGLKLG-UHFFFAOYSA-N 2-nitro-4,5-diphenyl-1h-imidazole Chemical compound N1C([N+](=O)[O-])=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 STGHAEAHYGLKLG-UHFFFAOYSA-N 0.000 title claims abstract description 8
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 229910052751 metal Inorganic materials 0.000 title abstract description 9
- 239000002184 metal Substances 0.000 title abstract description 9
- 150000002823 nitrates Chemical class 0.000 title abstract description 5
- 150000002739 metals Chemical class 0.000 title abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 48
- 150000002500 ions Chemical class 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 230000003993 interaction Effects 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 229910021645 metal ion Inorganic materials 0.000 claims description 6
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000013049 sediment Substances 0.000 claims 1
- 238000006396 nitration reaction Methods 0.000 abstract description 21
- 239000003795 chemical substances by application Substances 0.000 abstract description 14
- 230000000802 nitrating effect Effects 0.000 abstract description 13
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 11
- 239000000047 product Substances 0.000 abstract description 7
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 abstract description 5
- 150000004957 nitroimidazoles Chemical class 0.000 abstract description 5
- 230000009920 chelation Effects 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 229910001960 metal nitrate Inorganic materials 0.000 abstract description 3
- 239000013110 organic ligand Substances 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 206010021143 Hypoxia Diseases 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000001146 hypoxic effect Effects 0.000 description 5
- 150000002460 imidazoles Chemical class 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- GNWBLLYJQXKPIP-ZOGIJGBBSA-N (1s,3as,3bs,5ar,9ar,9bs,11as)-n,n-diethyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1h-indeno[5,4-f]quinoline-1-carboxamide Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(CC)CC)[C@@]2(C)CC1 GNWBLLYJQXKPIP-ZOGIJGBBSA-N 0.000 description 3
- 150000004959 2-nitroimidazoles Chemical class 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- -1 imidazole nitrocompounds Chemical class 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003904 antiprotozoal agent Substances 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
- 230000004071 biological effect Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- ODKHOKLXMBWVOQ-UHFFFAOYSA-N 4,5-diphenyl-1,3-oxazole Chemical class O1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ODKHOKLXMBWVOQ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 229910001579 aluminosilicate mineral Inorganic materials 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000842 anti-protozoal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(II) nitrate Inorganic materials [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000004729 solvothermal method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910002001 transition metal nitrate Inorganic materials 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Inorganic materials [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 1
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20110087A MD4150C1 (ro) | 2011-10-11 | 2011-10-11 | Procedeu de obţinere a compuşilor coordinativi ai Co(II), Ni(II) şi Zn(II) cu 2-nitro-4,5-difenilimidazol pornind de la 4,5-difenilimidazol şi nitraţii metalelor respective |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20110087A MD4150C1 (ro) | 2011-10-11 | 2011-10-11 | Procedeu de obţinere a compuşilor coordinativi ai Co(II), Ni(II) şi Zn(II) cu 2-nitro-4,5-difenilimidazol pornind de la 4,5-difenilimidazol şi nitraţii metalelor respective |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4150B1 MD4150B1 (en) | 2012-02-29 |
| MD4150C1 true MD4150C1 (ro) | 2012-09-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20110087A MD4150C1 (ro) | 2011-10-11 | 2011-10-11 | Procedeu de obţinere a compuşilor coordinativi ai Co(II), Ni(II) şi Zn(II) cu 2-nitro-4,5-difenilimidazol pornind de la 4,5-difenilimidazol şi nitraţii metalelor respective |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4150C1 (mo) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD4178C1 (ro) * | 2012-02-27 | 2013-02-28 | Институт Химии Академии Наук Молдовы | Procedeu de obţinere a 2-nitro-4,5-difenilimidazolului |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199592A (en) * | 1978-08-29 | 1980-04-22 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-2-nitroimidazoles |
| US4241060A (en) * | 1977-08-19 | 1980-12-23 | Hoffmann-La Roche Inc. | Nitroimidazoles and compositions thereof |
| US5008398A (en) * | 1988-10-15 | 1991-04-16 | Basf Aktiengesellschaft | Preparation of p-nitrophenyl-imidazoles |
| EP0510036A1 (en) * | 1990-01-12 | 1992-10-28 | Rhone Poulenc Rorer Sa | 2-SUBSTITUTED 4,5-DIPHENYLIMIDAZOLES. |
| WO1994019310A1 (en) * | 1993-02-26 | 1994-09-01 | Instituto Nacional De Engenharia E Tecnologia Industrial | New process for the nitration of aromatic compounds in mild, non-corrosive conditions |
| RU2021249C1 (ru) * | 1990-10-16 | 1994-10-15 | Индивидуально-частное предприятие "Ост-Вест" | Способ получения ароматических 1,2-дикетонов |
| CN1736976A (zh) * | 2005-08-30 | 2006-02-22 | 南京大学 | 硝酸铝在芳环硝化中的应用 |
| WO2008070336A2 (en) * | 2006-10-27 | 2008-06-12 | Natural Pharmacia International, Inc. | Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof |
| US20100004460A1 (en) * | 2007-01-23 | 2010-01-07 | Pola Pharma Inc | Method for producing 2-nitroimidazole derivative |
-
2011
- 2011-10-11 MD MDA20110087A patent/MD4150C1/ro not_active IP Right Cessation
Patent Citations (10)
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| US4241060A (en) * | 1977-08-19 | 1980-12-23 | Hoffmann-La Roche Inc. | Nitroimidazoles and compositions thereof |
| US4199592A (en) * | 1978-08-29 | 1980-04-22 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-2-nitroimidazoles |
| US5008398A (en) * | 1988-10-15 | 1991-04-16 | Basf Aktiengesellschaft | Preparation of p-nitrophenyl-imidazoles |
| EP0510036A1 (en) * | 1990-01-12 | 1992-10-28 | Rhone Poulenc Rorer Sa | 2-SUBSTITUTED 4,5-DIPHENYLIMIDAZOLES. |
| RU2021249C1 (ru) * | 1990-10-16 | 1994-10-15 | Индивидуально-частное предприятие "Ост-Вест" | Способ получения ароматических 1,2-дикетонов |
| WO1994019310A1 (en) * | 1993-02-26 | 1994-09-01 | Instituto Nacional De Engenharia E Tecnologia Industrial | New process for the nitration of aromatic compounds in mild, non-corrosive conditions |
| CN1736976A (zh) * | 2005-08-30 | 2006-02-22 | 南京大学 | 硝酸铝在芳环硝化中的应用 |
| WO2008070336A2 (en) * | 2006-10-27 | 2008-06-12 | Natural Pharmacia International, Inc. | Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof |
| US7842278B2 (en) * | 2006-10-27 | 2010-11-30 | Natural Pharmacia International, Inc. | Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof |
| US20100004460A1 (en) * | 2007-01-23 | 2010-01-07 | Pola Pharma Inc | Method for producing 2-nitroimidazole derivative |
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| Publication number | Publication date |
|---|---|
| MD4150B1 (en) | 2012-02-29 |
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