TWI499583B - 製備經取代１，３－二氫－２ｈ－吲哚－２－酮類的方法 - Google Patents
製備經取代１，３－二氫－２ｈ－吲哚－２－酮類的方法 Download PDFInfo
- Publication number
- TWI499583B TWI499583B TW100115968A TW100115968A TWI499583B TW I499583 B TWI499583 B TW I499583B TW 100115968 A TW100115968 A TW 100115968A TW 100115968 A TW100115968 A TW 100115968A TW I499583 B TWI499583 B TW I499583B
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- formula
- compound
- preparation
- alkyl
- group
- Prior art date
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- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 25
- 239000011541 reaction mixture Substances 0.000 claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 239000011593 sulfur Substances 0.000 claims description 16
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- -1 (C 1 -C) 6 )-Alkoxy Chemical compound 0.000 claims description 11
- 239000002798 polar solvent Substances 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 150000001340 alkali metals Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 6
- 239000002518 antifoaming agent Substances 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 229940079827 sodium hydrogen sulfite Drugs 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 235000010265 sodium sulphite Nutrition 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 2
- 230000002363 herbicidal effect Effects 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 235000015424 sodium Nutrition 0.000 claims description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000012847 fine chemical Substances 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- DDIIYGHHUMKDGI-UHFFFAOYSA-N 5-fluoro-1,3-dihydroindol-2-one Chemical compound FC1=CC=C2NC(=O)CC2=C1 DDIIYGHHUMKDGI-UHFFFAOYSA-N 0.000 description 2
- FPDLUAACCNVSQA-UHFFFAOYSA-N 7-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=CC2=C1NC(=O)C2 FPDLUAACCNVSQA-UHFFFAOYSA-N 0.000 description 2
- VMUIOEOYZHJLEZ-UHFFFAOYSA-N 7-fluoro-1,3-dihydroindol-2-one Chemical compound FC1=CC=CC2=C1NC(=O)C2 VMUIOEOYZHJLEZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- SHPZWXNWJLWGQK-UHFFFAOYSA-N 5,7-difluoro-1,3-dihydroindol-2-one Chemical compound FC1=CC(F)=CC2=C1NC(=O)C2 SHPZWXNWJLWGQK-UHFFFAOYSA-N 0.000 description 1
- BZSGXGOHHFXFBV-UHFFFAOYSA-N 5,7-difluoro-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound C1=C(F)C=C(F)C2=C1C(SC)C(=O)N2 BZSGXGOHHFXFBV-UHFFFAOYSA-N 0.000 description 1
- FAXDPCNVALCCBO-UHFFFAOYSA-N 5-fluoro-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound C1=C(F)C=C2C(SC)C(=O)NC2=C1 FAXDPCNVALCCBO-UHFFFAOYSA-N 0.000 description 1
- DBUUTXMZVKQLBJ-UHFFFAOYSA-N 7-chloro-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound C1=CC=C(Cl)C2=C1C(SC)C(=O)N2 DBUUTXMZVKQLBJ-UHFFFAOYSA-N 0.000 description 1
- LOKRAUWGFLVFID-UHFFFAOYSA-N 7-fluoro-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound C1=CC=C(F)C2=C1C(SC)C(=O)N2 LOKRAUWGFLVFID-UHFFFAOYSA-N 0.000 description 1
- APQCUXBFROFCOM-UHFFFAOYSA-N 7-methoxy-1,3-dihydroindol-2-one Chemical compound COC1=CC=CC2=C1NC(=O)C2 APQCUXBFROFCOM-UHFFFAOYSA-N 0.000 description 1
- QQWYCZKISHCCOW-UHFFFAOYSA-N 7-methoxy-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound COC1=CC=CC2=C1NC(=O)C2SC QQWYCZKISHCCOW-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 150000002923 oximes Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
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)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33294910P | 2010-05-10 | 2010-05-10 | |
| EP10162381 | 2010-05-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201206884A TW201206884A (en) | 2012-02-16 |
| TWI499583B true TWI499583B (zh) | 2015-09-11 |
Family
ID=42537445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW100115968A TWI499583B (zh) | 2010-05-10 | 2011-05-06 | 製備經取代１，３－二氫－２ｈ－吲哚－２－酮類的方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8563749B2 (enExample) |
| EP (1) | EP2569283B1 (enExample) |
| JP (1) | JP5815679B2 (enExample) |
| KR (1) | KR101783471B1 (enExample) |
| CN (1) | CN102985406B (enExample) |
| BR (1) | BR112012028767B1 (enExample) |
| DK (1) | DK2569283T3 (enExample) |
| ES (1) | ES2523226T3 (enExample) |
| IL (1) | IL222929A (enExample) |
| MX (1) | MX2012012959A (enExample) |
| TW (1) | TWI499583B (enExample) |
| WO (1) | WO2011141364A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3643210A1 (de) | 2018-10-25 | 2020-04-29 | Jura Elektroapparate AG | Verfahren zum erzeugen eines kaffeegetränks in einem kaffeeautomaten |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160032A (en) * | 1973-11-21 | 1979-07-03 | Sandoz, Inc. | Oxindoles as sleep-inducers |
| US5124347A (en) * | 1991-07-31 | 1992-06-23 | Warner-Lambert Co. | 3-5-ditertiarybutylphenyl-4-hydroxymethylidene derivatives of 1,3-dihydro-2H-indole-2-ones as antiinflammatory agents |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4503073A (en) * | 1981-01-07 | 1985-03-05 | A. H. Robins Company, Incorporated | 2-Amino-3-(alkylthiobenzoyl)-phenylacetic acids |
| FI80270C (fi) * | 1984-09-19 | 1990-05-10 | Pfizer | Foerfarande foer framstaellning av analgetiska och anti-inflammatoriska 1,3-diacyl-2-oxoindol-foereningar och mellanprodukter. |
| US5076835A (en) * | 1990-05-31 | 1991-12-31 | America Cyanamid Company | Aryloxyspiroalkylindolinone herbicides |
| FR2708605A1 (fr) * | 1993-07-30 | 1995-02-10 | Sanofi Sa | Dérivés du N-sulfonylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
-
2011
- 2011-05-06 MX MX2012012959A patent/MX2012012959A/es active IP Right Grant
- 2011-05-06 KR KR1020127031887A patent/KR101783471B1/ko active Active
- 2011-05-06 BR BR112012028767-2A patent/BR112012028767B1/pt active IP Right Grant
- 2011-05-06 ES ES11717663.6T patent/ES2523226T3/es active Active
- 2011-05-06 DK DK11717663.6T patent/DK2569283T3/en active
- 2011-05-06 TW TW100115968A patent/TWI499583B/zh active
- 2011-05-06 CN CN201180034200.3A patent/CN102985406B/zh active Active
- 2011-05-06 JP JP2013509511A patent/JP5815679B2/ja active Active
- 2011-05-06 EP EP11717663.6A patent/EP2569283B1/de active Active
- 2011-05-06 WO PCT/EP2011/057276 patent/WO2011141364A1/de not_active Ceased
- 2011-05-09 US US13/103,673 patent/US8563749B2/en active Active
-
2012
- 2012-11-08 IL IL222929A patent/IL222929A/en active IP Right Grant
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160032A (en) * | 1973-11-21 | 1979-07-03 | Sandoz, Inc. | Oxindoles as sleep-inducers |
| US5124347A (en) * | 1991-07-31 | 1992-06-23 | Warner-Lambert Co. | 3-5-ditertiarybutylphenyl-4-hydroxymethylidene derivatives of 1,3-dihydro-2H-indole-2-ones as antiinflammatory agents |
Non-Patent Citations (1)
| Title |
|---|
| Terrence J. Connolly, Tony Durst,"Non-reductive Desulfenylation of 3-Thioalkyl-2-oxindoles",Synlett 1996; 1996(7): 663-664. * |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2523226T3 (es) | 2014-11-24 |
| DK2569283T3 (en) | 2014-12-01 |
| JP2013526498A (ja) | 2013-06-24 |
| BR112012028767A2 (pt) | 2015-09-15 |
| TW201206884A (en) | 2012-02-16 |
| BR112012028767B1 (pt) | 2021-04-27 |
| CN102985406B (zh) | 2015-04-29 |
| WO2011141364A1 (de) | 2011-11-17 |
| US20110275832A1 (en) | 2011-11-10 |
| CN102985406A (zh) | 2013-03-20 |
| IL222929A (en) | 2015-06-30 |
| EP2569283B1 (de) | 2014-08-27 |
| US8563749B2 (en) | 2013-10-22 |
| IL222929A0 (en) | 2012-12-31 |
| JP5815679B2 (ja) | 2015-11-17 |
| MX2012012959A (es) | 2012-12-17 |
| KR101783471B1 (ko) | 2017-09-29 |
| EP2569283A1 (de) | 2013-03-20 |
| KR20130100913A (ko) | 2013-09-12 |
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