JP5491421B2 - ５−ｈｔ２ｃアゴニストである（ｒ）−８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンゾアゼピンに関連する中間体の調製のためのプロセス - Google Patents
５−ｈｔ２ｃアゴニストである（ｒ）−８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンゾアゼピンに関連する中間体の調製のためのプロセス Download PDFInfo
- Publication number
- JP5491421B2 JP5491421B2 JP2010549649A JP2010549649A JP5491421B2 JP 5491421 B2 JP5491421 B2 JP 5491421B2 JP 2010549649 A JP2010549649 A JP 2010549649A JP 2010549649 A JP2010549649 A JP 2010549649A JP 5491421 B2 JP5491421 B2 JP 5491421B2
- Authority
- JP
- Japan
- Prior art keywords
- chlorophenyl
- reacting
- ethanol
- propan
- bromide
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 94
- 230000008569 process Effects 0.000 title claims description 93
- 238000002360 preparation method Methods 0.000 title description 10
- XTTZERNUQAFMOF-QMMMGPOBSA-N lorcaserin Chemical compound C[C@H]1CNCCC2=CC=C(Cl)C=C12 XTTZERNUQAFMOF-QMMMGPOBSA-N 0.000 title description 8
- 239000000543 intermediate Substances 0.000 title description 6
- 239000002485 serotonin 2C agonist Substances 0.000 title 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 176
- HZFRKZWBVUJYDA-UHFFFAOYSA-N 2-(4-chlorophenyl)ethanol Chemical compound OCCC1=CC=C(Cl)C=C1 HZFRKZWBVUJYDA-UHFFFAOYSA-N 0.000 claims description 88
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 88
- YAFMYKFAUNCQPU-UHFFFAOYSA-N 1-(2-bromoethyl)-4-chlorobenzene Chemical compound ClC1=CC=C(CCBr)C=C1 YAFMYKFAUNCQPU-UHFFFAOYSA-N 0.000 claims description 73
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 45
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 42
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 26
- URWKQIHYBHDHPD-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethylamino]propan-2-ol Chemical compound CC(O)CNCCC1=CC=C(Cl)C=C1 URWKQIHYBHDHPD-UHFFFAOYSA-N 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 24
- ARSNVFGYXNWTPK-UHFFFAOYSA-N 2-chloro-n-[2-(4-chlorophenyl)ethyl]propan-1-amine;hydrochloride Chemical compound [Cl-].CC(Cl)C[NH2+]CCC1=CC=C(Cl)C=C1 ARSNVFGYXNWTPK-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 239000007789 gas Substances 0.000 claims description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 10
- -1 4-chloro-phenethyl-amino Chemical group 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- CLHHGPFQMDSVGA-UHFFFAOYSA-N propan-2-ol thionyl dichloride Chemical compound CC(C)O.S(=O)(Cl)Cl CLHHGPFQMDSVGA-UHFFFAOYSA-N 0.000 claims 1
- 239000012071 phase Substances 0.000 description 24
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 6
- BONQOKQKRRFITB-UHFFFAOYSA-N 1-[bis[2-(4-chlorophenyl)ethyl]amino]propan-2-ol Chemical compound C=1C=C(Cl)C=CC=1CCN(CC(O)C)CCC1=CC=C(Cl)C=C1 BONQOKQKRRFITB-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000003518 caustics Substances 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- 239000012455 biphasic mixture Substances 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 208000008589 Obesity Diseases 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004305 normal phase HPLC Methods 0.000 description 3
- 235000020824 obesity Nutrition 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- MVOSNPUNXINWAD-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanol Chemical compound CC(O)C1=CC=C(Cl)C=C1 MVOSNPUNXINWAD-UHFFFAOYSA-N 0.000 description 2
- IMMGGYIXPZKRMM-UHFFFAOYSA-N 2-chloro-n-[2-(4-chlorophenyl)ethyl]propan-1-amine Chemical compound CC(Cl)CNCCC1=CC=C(Cl)C=C1 IMMGGYIXPZKRMM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 230000004048 modification Effects 0.000 description 2
- KMCQIOFKQGIPTG-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]propan-1-amine Chemical compound CCCNCCC1=CC=C(Cl)C=C1 KMCQIOFKQGIPTG-UHFFFAOYSA-N 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 239000000018 receptor agonist Substances 0.000 description 2
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- 229940076279 serotonin Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 2
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- DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
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- 230000003579 anti-obesity Effects 0.000 description 1
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- 229940125710 antiobesity agent Drugs 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
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- 125000000068 chlorophenyl group Chemical group 0.000 description 1
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- 229960004597 dexfenfluramine Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- 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
- C07C213/08—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 not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6810208P | 2008-03-04 | 2008-03-04 | |
| US61/068,102 | 2008-03-04 | ||
| PCT/US2009/001340 WO2009111004A1 (en) | 2008-03-04 | 2009-03-03 | Processes for the preparation of intermediates related to the 5-ht2c agonist (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011513402A JP2011513402A (ja) | 2011-04-28 |
| JP2011513402A5 JP2011513402A5 (enExample) | 2013-03-21 |
| JP5491421B2 true JP5491421B2 (ja) | 2014-05-14 |
Family
ID=40589739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010549649A Expired - Fee Related JP5491421B2 (ja) | 2008-03-04 | 2009-03-03 | ５−ｈｔ２ｃアゴニストである（ｒ）−８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンゾアゼピンに関連する中間体の調製のためのプロセス |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8822727B2 (enExample) |
| EP (1) | EP2288585A1 (enExample) |
| JP (1) | JP5491421B2 (enExample) |
| CN (1) | CN102015591B (enExample) |
| WO (1) | WO2009111004A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA05013364A (es) | 2003-06-17 | 2006-03-17 | Arena Pharm Inc | Procedimiento para preparar 3-benzazepinas. |
| BRPI0515862A2 (pt) | 2004-12-23 | 2011-10-11 | Arena Pharm Inc | uso de fentermina e agonista seletivo do receptor de 5ht-2c na preparação de composições, composições moduladoras do receptor de 5ht-2c e forma de dosagem unitária compreendendo as mesmas |
| JP5199997B2 (ja) | 2006-04-03 | 2013-05-15 | アリーナ ファーマシューティカルズ， インコーポレイテッド | ８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンズアゼピンおよびこれに関連する中間体を調製するためのプロセス |
| US8822727B2 (en) | 2008-03-04 | 2014-09-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of intermediates related to the 5-HT2C agonist (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine |
| WO2010148207A2 (en) | 2009-06-18 | 2010-12-23 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-ht2c receptor agonists |
| KR20130112848A (ko) | 2010-06-02 | 2013-10-14 | 아레나 파마슈티칼스, 인크. | 5-ｈｔ2ｃ 수용체 아고니스트의 제조 방법 |
| KR20130138770A (ko) | 2010-09-01 | 2013-12-19 | 아레나 파마슈티칼스, 인크. | 광학적으로 활성 산을 갖는 로르카세린의 염 |
| EP2611781A1 (en) | 2010-09-01 | 2013-07-10 | Arena Pharmaceuticals, Inc. | Fast-dissolve dosage forms of 5-ht2c agonists |
| EP3485878A1 (en) | 2010-09-01 | 2019-05-22 | Arena Pharmaceuticals, Inc. | Modified-release dosage forms of 5-ht2c agonists useful for weight management |
| SG188361A1 (en) | 2010-09-01 | 2013-04-30 | Arena Pharm Inc | Non-hygroscopic salts of 5-ht2c agonists |
| US20130267500A1 (en) | 2010-09-01 | 2013-10-10 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level |
| US8999970B2 (en) | 2010-09-01 | 2015-04-07 | Arena Pharmaceuticals, Inc. | Administration of an anti-obesity compound to individuals with renal impairment |
| CA2886875A1 (en) | 2012-10-09 | 2014-04-17 | Arena Pharmaceuticals, Inc. | Method of weight management |
| WO2014187768A1 (en) | 2013-05-20 | 2014-11-27 | Lek Pharmaceuticals D.D. | Novel synthetic processes to 8-chloro-3-benzo[d]azepine via friedel-crafts alkylation of olefin |
| CN105517994A (zh) | 2013-06-21 | 2016-04-20 | 斯洛文尼亚莱柯制药股份有限公司 | 通过α-取代的苯乙烯类的不对称还原制备手性1-甲基-2，3，4，5-1H-苯并二氮杂*类 |
| CN103901151A (zh) * | 2014-04-23 | 2014-07-02 | 湖北朗昕生化药业有限公司 | 一种hplc法检测氯卡色林盐酸盐含量的方法 |
| WO2015170346A1 (en) | 2014-05-09 | 2015-11-12 | Council Of Scientific & Industrial Research | A process for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-benzo[d]azepine its enantiomers |
| WO2016069875A1 (en) | 2014-10-30 | 2016-05-06 | Arena Pharmaceuticals, Inc. | Compositions and methods for ceasing tobacco smoking |
| CN107673949B (zh) * | 2017-10-25 | 2021-02-23 | 南京恒旺生物医药有限公司 | 一种1-氯-3-甲基-2-丁烯的制备方法 |
| CN112358406A (zh) * | 2020-10-28 | 2021-02-12 | 山东省药学科学院 | 一种氯卡色林中间体的制备方法 |
| CN115784911A (zh) * | 2022-10-19 | 2023-03-14 | 山东省药学科学院 | 一种1-[2-(4-氯苯基)-乙基氨基]-2-丙醇的合成方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2900415A (en) | 1954-12-14 | 1959-08-18 | Lakeside Lab Inc | Synthesized antispasmodic compounds |
| CH481110A (de) | 1967-02-17 | 1969-11-15 | Geigy Ag J R | Verfahren zur Herstellung von 1,2,4,5-Tetrahydro-3-azepinen |
| CH498122A (de) | 1968-02-09 | 1970-10-31 | Geigy Ag J R | Verfahren zur Herstellung eines neuen Tetrahydroazepinderivates |
| CH500194A (de) | 1968-02-15 | 1970-12-15 | Ciba Geigy Ag | Verfahren zur Herstellung von Tetrahydroazepinderivaten |
| US4233217A (en) | 1968-03-11 | 1980-11-11 | Pennwalt Corporation | Substituted 1,2,4,5-tetrahydro-3H, 3 benzazepines |
| GB1268243A (en) | 1968-03-11 | 1972-03-22 | Wallace & Tiernan Inc | 0,2,4,5,-tetrahydro-3h,3-benzazepines |
| FR314F (enExample) | 1968-03-22 | 1970-05-25 | ||
| FR7736M (enExample) | 1968-09-02 | 1970-03-09 | ||
| US3716639A (en) | 1970-03-11 | 1973-02-13 | Ciba Geigy Corp | Anorexigenic tetrahydrobenzazepines |
| US3795683A (en) | 1970-08-19 | 1974-03-05 | Hoffmann La Roche | 2,3,4,5-tetrahydro-1h-3-benzazepines |
| LU65954A1 (enExample) | 1972-08-25 | 1974-03-07 | ||
| US4210749A (en) | 1974-11-12 | 1980-07-01 | Pennwalt Corporation | Substituted 1,2,4,5-tetrahydro-3H,3 benzazepines |
| SE7510988L (sv) | 1975-10-01 | 1977-04-02 | Draco Ab | Nya farmaceutiskt aktiva foreningar |
| US4111957A (en) | 1977-02-02 | 1978-09-05 | Smithkline Corporation | Substituted 1-thienyl and furyl-2,3,4,5-tetrahydro-1H-3-benzazepine compounds |
| US4108989A (en) | 1977-04-01 | 1978-08-22 | Smithkline Corporation | 2,3,4,5-tetrahydro-1h-3-benzazepine-7,8-diones |
| DE2758001A1 (de) | 1977-12-24 | 1979-07-12 | Hoechst Ag | Cephalosporinderivate und verfahren zu ihrer herstellung |
| CA1090797A (en) | 1978-06-20 | 1980-12-02 | Kenneth G. Holden | Substituted 1-thienyl and furyl-2,3,4,5-tetrahydro-1h- 3-benzazepine compounds |
| AU515236B2 (en) | 1978-06-26 | 1981-03-26 | Smithkline Corporation | Substituted-1-thienyl and furyl-2,3,4,5-tetrahydro-14-3 benzazepine derivatives |
| ZA792785B (en) | 1978-07-07 | 1980-08-27 | Smithkline Corp | Mercapto substituted-2,3,4,5-tetrahydro-1h-3-benzazepines |
| IE50355B1 (en) | 1979-10-20 | 1986-04-02 | Wyeth John & Brother Ltd | Morpholine derivatives |
| US4477378A (en) | 1980-02-05 | 1984-10-16 | Schering Corp. | Esters of substituted 8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines |
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2009
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- 2009-03-03 WO PCT/US2009/001340 patent/WO2009111004A1/en not_active Ceased
- 2009-03-03 CN CN200980116092.7A patent/CN102015591B/zh not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2011513402A (ja) | 2011-04-28 |
| WO2009111004A1 (en) | 2009-09-11 |
| CN102015591A (zh) | 2011-04-13 |
| CN102015591B (zh) | 2014-01-29 |
| US20110015438A1 (en) | 2011-01-20 |
| US8822727B2 (en) | 2014-09-02 |
| EP2288585A1 (en) | 2011-03-02 |
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