CA2698808A1 - Synthesis of deuterated catechols and benzo[d][1,3] dioxoles and derivatives thereof - Google Patents
Synthesis of deuterated catechols and benzo[d][1,3] dioxoles and derivatives thereof Download PDFInfo
- Publication number
- CA2698808A1 CA2698808A1 CA2698808A CA2698808A CA2698808A1 CA 2698808 A1 CA2698808 A1 CA 2698808A1 CA 2698808 A CA2698808 A CA 2698808A CA 2698808 A CA2698808 A CA 2698808A CA 2698808 A1 CA2698808 A1 CA 2698808A1
- Authority
- CA
- Canada
- Prior art keywords
- deuterated
- coor
- represented
- nhc
- structural formula
- 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.)
- Abandoned
Links
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical class C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 title claims description 49
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 title claims description 43
- 230000015572 biosynthetic process Effects 0.000 title abstract description 61
- 238000003786 synthesis reaction Methods 0.000 title abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 70
- 230000008569 process Effects 0.000 claims abstract description 23
- -1 chloro, iodo Chemical group 0.000 claims description 187
- 239000000203 mixture Substances 0.000 claims description 135
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical class C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims description 127
- 150000001875 compounds Chemical class 0.000 claims description 65
- 229910052805 deuterium Inorganic materials 0.000 claims description 59
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 230000000155 isotopic effect Effects 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 39
- 239000008194 pharmaceutical composition Substances 0.000 claims description 34
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 32
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- IEHKWSGCTWLXFU-IIBYNOLFSA-N tadalafil Chemical class C1=C2OCOC2=CC([C@@H]2C3=C([C]4C=CC=CC4=N3)C[C@H]3N2C(=O)CN(C3=O)C)=C1 IEHKWSGCTWLXFU-IIBYNOLFSA-N 0.000 claims description 21
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 208000033830 Hot Flashes Diseases 0.000 claims description 14
- 206010060800 Hot flush Diseases 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 239000003937 drug carrier Substances 0.000 claims description 11
- 150000003836 berberines Chemical class 0.000 claims description 10
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical group [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 claims description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 9
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 7
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 6
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 5
- 125000006242 amine protecting group Chemical group 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
- VGGNVBNNVSIGKG-UHFFFAOYSA-N n,n,2-trimethylaziridine-1-carboxamide Chemical compound CC1CN1C(=O)N(C)C VGGNVBNNVSIGKG-UHFFFAOYSA-N 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000006184 cosolvent Substances 0.000 claims 2
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 claims 1
- WBDLSXCAFVEULB-UHFFFAOYSA-N acetonitrile;methylsulfinylmethane Chemical compound CC#N.CS(C)=O WBDLSXCAFVEULB-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 102
- 239000003814 drug Substances 0.000 description 70
- 229960002296 paroxetine Drugs 0.000 description 61
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
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- 239000000243 solution Substances 0.000 description 44
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- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 42
- 229910001868 water Inorganic materials 0.000 description 40
- 229940124597 therapeutic agent Drugs 0.000 description 39
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
- 235000002639 sodium chloride Nutrition 0.000 description 37
- 108010001237 Cytochrome P-450 CYP2D6 Proteins 0.000 description 33
- 102100021704 Cytochrome P450 2D6 Human genes 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
- 238000012360 testing method Methods 0.000 description 31
- 239000007787 solid Substances 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 229940126062 Compound A Drugs 0.000 description 26
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 26
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 23
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 9
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99356507P | 2007-09-13 | 2007-09-13 | |
| US60/993,565 | 2007-09-13 | ||
| PCT/US2008/010643 WO2009035652A1 (en) | 2007-09-13 | 2008-09-12 | Synthesis of deuterated catechols and benzo[d][1,3] dioxoles and derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2698808A1 true CA2698808A1 (en) | 2009-03-19 |
Family
ID=40116877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2698808A Abandoned CA2698808A1 (en) | 2007-09-13 | 2008-09-12 | Synthesis of deuterated catechols and benzo[d][1,3] dioxoles and derivatives thereof |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US8822498B2 (enExample) |
| EP (2) | EP2727915B1 (enExample) |
| JP (1) | JP5647519B2 (enExample) |
| CN (1) | CN101855218A (enExample) |
| AU (1) | AU2008299921B2 (enExample) |
| CA (1) | CA2698808A1 (enExample) |
| MX (1) | MX2010002692A (enExample) |
| WO (1) | WO2009035652A1 (enExample) |
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| CN101273024A (zh) * | 2005-07-29 | 2008-09-24 | 康瑟特制药公司 | 新颖苯并[d][1,3]-二氧杂环戊烯衍生物 |
| US20070112031A1 (en) * | 2005-11-14 | 2007-05-17 | Gant Thomas G | Substituted phenylpiperidines with serotoninergic activity and enhanced therapeutic properties |
| JP5647519B2 (ja) | 2007-09-13 | 2014-12-24 | コンサート ファーマシューティカルズ インコーポレイテッド | 重水素化カテコールおよびベンゾ［ｄ］［１，３］ジオキソールおよびその誘導体の合成 |
| HUE047354T2 (hu) | 2011-05-18 | 2020-04-28 | Vertex Pharmaceuticals Europe Ltd | Ivacaftor deuterizált származékai |
| ME03652B (me) * | 2011-05-18 | 2020-07-20 | Vertex Pharmaceuticals Europe Ltd | Deuterisani derivati ivakaftora |
| US20120302526A1 (en) * | 2011-05-27 | 2012-11-29 | Regents Of The University Of Colorado, A Body Corporate | Methods for treating post-traumatic stress disorder |
| CN102942554B (zh) * | 2012-11-14 | 2014-05-28 | 广西师范大学 | 胡椒乙胺缩水杨醛及其合成方法和应用 |
| CN102924426B (zh) * | 2012-11-14 | 2014-07-02 | 广西师范大学 | 胡椒乙胺缩5-氯水杨醛及其合成方法和应用 |
| MX376163B (es) * | 2014-05-13 | 2025-03-07 | Hoffmann La Roche | Compuestos heterocíclicos deuterados y su uso como agentes formadores de imágenes. |
| CN103980271B (zh) * | 2014-05-30 | 2015-12-02 | 天津长森药业有限公司 | 黄藤素及其类似物的制备方法 |
| CN104059030B (zh) * | 2014-05-30 | 2016-05-04 | 镇江圣安医药有限公司 | [(苯硫烷基)-苯基]哌嗪的衍生物及其药物组合物和用途 |
| KR20250008786A (ko) * | 2014-07-29 | 2025-01-15 | 센젠 하이타이드 바이오파마슈티컬 리미티드 | 베르베린 염, 우르소데옥시콜산 염 및 병용물, 이들의 제조 및 응용 방법 |
| WO2016109795A1 (en) | 2014-12-31 | 2016-07-07 | Concert Pharmaceuticals, Inc. | Deuterated funapide and difluorofunapide |
| US10196384B2 (en) | 2015-03-31 | 2019-02-05 | Vertex Pharmaceuticals (Europe) Limited | Deuterated CFTR modulators |
| HK1258473A1 (zh) | 2015-09-25 | 2019-11-15 | Vertex Pharmaceuticals (Europe) Limited | 氘代cftr增效剂 |
| CN108602786B (zh) | 2016-02-25 | 2019-04-23 | 深圳市塔吉瑞生物医药有限公司 | 一种取代的噁二唑类化合物及包含该化合物的组合物及其用途 |
| KR101970326B1 (ko) * | 2016-08-05 | 2019-04-18 | 고려대학교 산학협력단 | 당 부가된 엔클로미펜, 이의 제조방법 및 이를 포함하는 약학적 조성물 |
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| CN113735847B (zh) * | 2021-09-10 | 2022-06-07 | 四川大学 | 一种盐酸小檗碱的合成制备方法 |
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-
2008
- 2008-09-12 JP JP2010524866A patent/JP5647519B2/ja not_active Expired - Fee Related
- 2008-09-12 EP EP13185607.2A patent/EP2727915B1/en not_active Not-in-force
- 2008-09-12 EP EP08830527.1A patent/EP2200997B9/en not_active Not-in-force
- 2008-09-12 CA CA2698808A patent/CA2698808A1/en not_active Abandoned
- 2008-09-12 WO PCT/US2008/010643 patent/WO2009035652A1/en not_active Ceased
- 2008-09-12 MX MX2010002692A patent/MX2010002692A/es not_active Application Discontinuation
- 2008-09-12 US US12/283,621 patent/US8822498B2/en not_active Expired - Fee Related
- 2008-09-12 AU AU2008299921A patent/AU2008299921B2/en not_active Ceased
- 2008-09-12 CN CN200880110558A patent/CN101855218A/zh active Pending
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2014
- 2014-07-24 US US14/340,143 patent/US9315483B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010539166A (ja) | 2010-12-16 |
| EP2727915A1 (en) | 2014-05-07 |
| WO2009035652A1 (en) | 2009-03-19 |
| EP2727915B1 (en) | 2016-04-13 |
| AU2008299921A1 (en) | 2009-03-19 |
| MX2010002692A (es) | 2010-06-01 |
| EP2200997B9 (en) | 2016-01-13 |
| EP2200997B1 (en) | 2013-11-06 |
| US20140336387A1 (en) | 2014-11-13 |
| AU2008299921B2 (en) | 2012-03-01 |
| JP5647519B2 (ja) | 2014-12-24 |
| US9315483B2 (en) | 2016-04-19 |
| AU2008299921A8 (en) | 2010-04-08 |
| US8822498B2 (en) | 2014-09-02 |
| US20090143432A1 (en) | 2009-06-04 |
| CN101855218A (zh) | 2010-10-06 |
| EP2200997A1 (en) | 2010-06-30 |
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