BR112013007280B1 - processo para produção de um composto aminoálcool terciário - Google Patents
processo para produção de um composto aminoálcool terciário Download PDFInfo
- Publication number
- BR112013007280B1 BR112013007280B1 BR112013007280-6A BR112013007280A BR112013007280B1 BR 112013007280 B1 BR112013007280 B1 BR 112013007280B1 BR 112013007280 A BR112013007280 A BR 112013007280A BR 112013007280 B1 BR112013007280 B1 BR 112013007280B1
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- BR
- Brazil
- Prior art keywords
- compound
- formula
- alkyl
- cycloalkyl
- alternatively
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 46
- 150000001875 compounds Chemical class 0.000 title claims abstract description 26
- 125000001302 tertiary amino group Chemical group 0.000 title claims abstract description 19
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 32
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 20
- -1 AMINO ALCOHOL COMPOUND Chemical group 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 16
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 14
- 239000013067 intermediate product Substances 0.000 claims description 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 13
- XRIBIDPMFSLGFS-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropan-1-ol Chemical compound CN(C)C(C)(C)CO XRIBIDPMFSLGFS-UHFFFAOYSA-N 0.000 claims description 9
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
- SYWNSKBWIROVPF-UHFFFAOYSA-N [1-(dimethylamino)cyclohexyl]methanol Chemical compound CN(C)C1(CO)CCCCC1 SYWNSKBWIROVPF-UHFFFAOYSA-N 0.000 claims description 4
- FGHOJUJBJHVRGT-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropane-1,3-diol Chemical compound CN(C)C(C)(CO)CO FGHOJUJBJHVRGT-UHFFFAOYSA-N 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 abstract description 11
- 125000004971 nitroalkyl group Chemical group 0.000 abstract description 10
- 230000029936 alkylation Effects 0.000 abstract description 8
- 150000001414 amino alcohols Chemical class 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- 239000000047 product Substances 0.000 description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- 238000007792 addition Methods 0.000 description 15
- 125000000753 cycloalkyl group Chemical group 0.000 description 15
- 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 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 238000006482 condensation reaction Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- MVGJRISPEUZYAQ-UHFFFAOYSA-N 2-methyl-2-nitropropan-1-ol Chemical compound OCC(C)(C)[N+]([O-])=O MVGJRISPEUZYAQ-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 5
- OLQJQHSAWMFDJE-UHFFFAOYSA-N 2-(hydroxymethyl)-2-nitropropane-1,3-diol Chemical compound OCC(CO)(CO)[N+]([O-])=O OLQJQHSAWMFDJE-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021189 garnishes Nutrition 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 230000011987 methylation Effects 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- USOLRVZGBJWYTO-UHFFFAOYSA-N (1-nitrocyclohexyl)methanol Chemical compound OCC1([N+]([O-])=O)CCCCC1 USOLRVZGBJWYTO-UHFFFAOYSA-N 0.000 description 2
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 2
- ARYCHBXRTBLOSY-UHFFFAOYSA-N 2-(dimethylamino)-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)N(C)C ARYCHBXRTBLOSY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001299 aldehydes Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000005555 metalworking Methods 0.000 description 2
- VMOWKUTXPNPTEN-UHFFFAOYSA-N n,n-dimethylpropan-2-amine Chemical compound CC(C)N(C)C VMOWKUTXPNPTEN-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- VDPLLINNMXFNQX-UHFFFAOYSA-N (1-aminocyclohexyl)methanol Chemical compound OCC1(N)CCCCC1 VDPLLINNMXFNQX-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- LOTYADDQWWVBDJ-UHFFFAOYSA-N 2-methyl-2-nitropropane-1,3-diol Chemical compound OCC(C)(CO)[N+]([O-])=O LOTYADDQWWVBDJ-UHFFFAOYSA-N 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 240000006413 Prunus persica var. persica Species 0.000 description 1
- STFXLPCFNRGVQH-UHFFFAOYSA-N [1-(methylamino)cyclohexyl]methanol Chemical compound CNC1(CO)CCCCC1 STFXLPCFNRGVQH-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- IZXGZAJMDLJLMF-UHFFFAOYSA-N methylaminomethanol Chemical compound CNCO IZXGZAJMDLJLMF-UHFFFAOYSA-N 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38666410P | 2010-09-27 | 2010-09-27 | |
| US61/386,664 | 2010-09-27 | ||
| PCT/US2011/052566 WO2012044508A1 (en) | 2010-09-27 | 2011-09-21 | Process for making tertiary aminoalcohol compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112013007280A2 BR112013007280A2 (pt) | 2020-10-06 |
| BR112013007280B1 true BR112013007280B1 (pt) | 2021-06-08 |
Family
ID=44721109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112013007280-6A BR112013007280B1 (pt) | 2010-09-27 | 2011-09-21 | processo para produção de um composto aminoálcool terciário |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8674139B2 (https=) |
| EP (1) | EP2606029B1 (https=) |
| JP (1) | JP5816692B2 (https=) |
| CN (1) | CN103153942B (https=) |
| BR (1) | BR112013007280B1 (https=) |
| WO (1) | WO2012044508A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013012777A2 (en) * | 2011-07-20 | 2013-01-24 | Angus Chemical Company | Process for making tertiary aminoalcohol compounds |
| US10159930B2 (en) * | 2014-10-10 | 2018-12-25 | Dow Global Technologies Llc | Aqueous solution of 2-dimethylamino-2-hydroxymethyl-1, 3-propanediol useful for acid gas removal from gaseous mixtures |
| US10286356B2 (en) * | 2014-10-10 | 2019-05-14 | Dow Global Technologies Llc | Process for the removal of acid gases from gaseous mixtures using an aqueous solution of 2-dimethylamino-2-hydroxymethyl-1, 3-propanediol |
| EP3635061B1 (en) | 2017-05-12 | 2022-02-16 | ANGUS Chemical Company | Ether amine compositions and coatings |
| CN107488118A (zh) * | 2017-08-22 | 2017-12-19 | 嘉兴润博化工科技有限公司 | 一种一锅法制备叔氨基醇化合物的方法 |
| CN109692548A (zh) * | 2018-12-06 | 2019-04-30 | 嘉兴润博化工科技有限公司 | 一种选择性脱硫化合物 |
| CN110172029B (zh) * | 2019-06-28 | 2022-09-23 | 南京红宝丽醇胺化学有限公司 | 一种连续合成2-氨基-2-甲基-1-丙醇的方法 |
| CN114105788A (zh) * | 2021-11-29 | 2022-03-01 | 河北旭阳能源有限公司 | 一种高选择性制备2-氨基-2-甲基-1-丙醇的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3564057A (en) * | 1968-10-07 | 1971-02-16 | Commercial Solvents Corp | Production of alkanolamines |
| US3651144A (en) * | 1969-06-06 | 1972-03-21 | John B Tindall | Production of alkanolamines |
| CH609674A5 (https=) * | 1975-02-04 | 1979-03-15 | Azote & Prod Chim | |
| JPH0967319A (ja) * | 1995-09-01 | 1997-03-11 | Konica Corp | アルキルアニリン類の製造方法 |
| EP2280925B1 (en) * | 2008-04-16 | 2013-08-14 | Angus Chemical Company | Process for the manufacture of nitropropanes |
| WO2009129097A1 (en) * | 2008-04-16 | 2009-10-22 | Angus Chemical Company | Nitrated hydrocarbons, derivatives, and processes for their manufacture |
-
2011
- 2011-09-21 CN CN201180047556.0A patent/CN103153942B/zh active Active
- 2011-09-21 WO PCT/US2011/052566 patent/WO2012044508A1/en not_active Ceased
- 2011-09-21 EP EP11764061.5A patent/EP2606029B1/en active Active
- 2011-09-21 US US13/819,098 patent/US8674139B2/en active Active
- 2011-09-21 BR BR112013007280-6A patent/BR112013007280B1/pt active IP Right Grant
- 2011-09-21 JP JP2013530281A patent/JP5816692B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013537911A (ja) | 2013-10-07 |
| EP2606029B1 (en) | 2016-06-08 |
| BR112013007280A2 (pt) | 2020-10-06 |
| JP5816692B2 (ja) | 2015-11-18 |
| CN103153942B (zh) | 2015-04-22 |
| US20130172622A1 (en) | 2013-07-04 |
| US8674139B2 (en) | 2014-03-18 |
| CN103153942A (zh) | 2013-06-12 |
| WO2012044508A1 (en) | 2012-04-05 |
| EP2606029A1 (en) | 2013-06-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B06F | Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette] | ||
| B06U | Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 21/09/2011, OBSERVADAS AS CONDICOES LEGAIS. |