ES2523226T3 - Procedimiento para la preparación de 1,3-dihidro-2H-indol-2-onas - Google Patents
Procedimiento para la preparación de 1,3-dihidro-2H-indol-2-onas Download PDFInfo
- Publication number
- ES2523226T3 ES2523226T3 ES11717663.6T ES11717663T ES2523226T3 ES 2523226 T3 ES2523226 T3 ES 2523226T3 ES 11717663 T ES11717663 T ES 11717663T ES 2523226 T3 ES2523226 T3 ES 2523226T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- alkyl
- preparation
- group
- substituted
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 20
- 239000011541 reaction mixture Substances 0.000 claims abstract description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 17
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
- 239000011593 sulfur Substances 0.000 claims abstract description 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 14
- 239000002798 polar solvent Substances 0.000 claims abstract description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 238000009835 boiling Methods 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 4
- 125000005366 cycloalkylthio group Chemical group 0.000 claims abstract description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 4
- 239000000725 suspension Substances 0.000 claims abstract description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 3
- 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 abstract description 3
- 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 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 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
- 239000003513 alkali Substances 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
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 235000010265 sodium sulphite Nutrition 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 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 3
- -1 alkaline earth metal bisulfite Chemical class 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000002518 antifoaming agent Substances 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
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 2
- 235000015424 sodium Nutrition 0.000 claims description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 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 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 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
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical class C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 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
- DDIIYGHHUMKDGI-UHFFFAOYSA-N 5-fluoro-1,3-dihydroindol-2-one Chemical compound FC1=CC=C2NC(=O)CC2=C1 DDIIYGHHUMKDGI-UHFFFAOYSA-N 0.000 description 1
- FPDLUAACCNVSQA-UHFFFAOYSA-N 7-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=CC2=C1NC(=O)C2 FPDLUAACCNVSQA-UHFFFAOYSA-N 0.000 description 1
- NVEHJKNCMNJVMU-UHFFFAOYSA-N 7-chloro-1,3-dihydroindol-2-one;7-chloro-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound ClC1=CC=CC2=C1NC(=O)C2.C1=CC=C(Cl)C2=C1C(SC)C(=O)N2 NVEHJKNCMNJVMU-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
- FXVPFWQVLGDQLT-UHFFFAOYSA-N FC=1C=C2C(C(NC2=CC1)=O)SC.FC=1C=C2CC(NC2=CC1)=O Chemical compound FC=1C=C2C(C(NC2=CC1)=O)SC.FC=1C=C2CC(NC2=CC1)=O FXVPFWQVLGDQLT-UHFFFAOYSA-N 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 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
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 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
- 239000013530 defoamer Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 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
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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33294910P | 2010-05-10 | 2010-05-10 | |
| EP10162381 | 2010-05-10 | ||
| US332949P | 2010-05-10 | ||
| EP10162381 | 2010-05-10 | ||
| PCT/EP2011/057276 WO2011141364A1 (de) | 2010-05-10 | 2011-05-06 | Verfahren zur herstellung von substituierten 1,3-dihydro-2h-indol-2-onen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2523226T3 true ES2523226T3 (es) | 2014-11-24 |
Family
ID=42537445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11717663.6T Active ES2523226T3 (es) | 2010-05-10 | 2011-05-06 | Procedimiento para la preparación de 1,3-dihidro-2H-indol-2-onas |
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 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160032A (en) | 1973-11-21 | 1979-07-03 | Sandoz, Inc. | Oxindoles as sleep-inducers |
| 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 |
| 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 |
| 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 KR KR1020127031887A patent/KR101783471B1/ko active Active
- 2011-05-06 JP JP2013509511A patent/JP5815679B2/ja active Active
- 2011-05-06 MX MX2012012959A patent/MX2012012959A/es active IP Right Grant
- 2011-05-06 EP EP11717663.6A patent/EP2569283B1/de active Active
- 2011-05-06 WO PCT/EP2011/057276 patent/WO2011141364A1/de not_active Ceased
- 2011-05-06 CN CN201180034200.3A patent/CN102985406B/zh active Active
- 2011-05-06 TW TW100115968A patent/TWI499583B/zh 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
- 2011-05-09 US US13/103,673 patent/US8563749B2/en active Active
-
2012
- 2012-11-08 IL IL222929A patent/IL222929A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| TWI499583B (zh) | 2015-09-11 |
| EP2569283B1 (de) | 2014-08-27 |
| IL222929A (en) | 2015-06-30 |
| MX2012012959A (es) | 2012-12-17 |
| DK2569283T3 (en) | 2014-12-01 |
| JP2013526498A (ja) | 2013-06-24 |
| WO2011141364A1 (de) | 2011-11-17 |
| KR101783471B1 (ko) | 2017-09-29 |
| TW201206884A (en) | 2012-02-16 |
| JP5815679B2 (ja) | 2015-11-17 |
| BR112012028767A2 (pt) | 2015-09-15 |
| US8563749B2 (en) | 2013-10-22 |
| BR112012028767B1 (pt) | 2021-04-27 |
| CN102985406A (zh) | 2013-03-20 |
| KR20130100913A (ko) | 2013-09-12 |
| CN102985406B (zh) | 2015-04-29 |
| IL222929A0 (en) | 2012-12-31 |
| EP2569283A1 (de) | 2013-03-20 |
| US20110275832A1 (en) | 2011-11-10 |
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