CN103086944A - N-羟基-3-[4-[[[2-(2-甲基-1h-吲哚-3-基)乙基]氨基]甲基]苯基]-2e-2-丙烯酰胺的制备方法及其原料 - Google Patents
N-羟基-3-[4-[[[2-(2-甲基-1h-吲哚-3-基)乙基]氨基]甲基]苯基]-2e-2-丙烯酰胺的制备方法及其原料 Download PDFInfo
- Publication number
- CN103086944A CN103086944A CN2012103501544A CN201210350154A CN103086944A CN 103086944 A CN103086944 A CN 103086944A CN 2012103501544 A CN2012103501544 A CN 2012103501544A CN 201210350154 A CN201210350154 A CN 201210350154A CN 103086944 A CN103086944 A CN 103086944A
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- China
- Prior art keywords
- methyl
- phenyl
- indole
- ethyl
- amino
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 49
- 230000008569 process Effects 0.000 title claims description 12
- FPOHNWQLNRZRFC-ZHACJKMWSA-N panobinostat Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(\C=C\C(=O)NO)C=C1 FPOHNWQLNRZRFC-ZHACJKMWSA-N 0.000 title abstract 3
- 239000007858 starting material Substances 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 57
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 60
- 239000000725 suspension Substances 0.000 claims description 47
- 239000011541 reaction mixture Substances 0.000 claims description 40
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
- CCRIVCWOXSIYEP-UHFFFAOYSA-N methyl prop-2-enoate;hydrochloride Chemical compound Cl.COC(=O)C=C CCRIVCWOXSIYEP-UHFFFAOYSA-N 0.000 claims description 31
- 238000003756 stirring Methods 0.000 claims description 27
- 238000002425 crystallisation Methods 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000000706 filtrate Substances 0.000 claims description 19
- 230000008025 crystallization Effects 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000001914 filtration Methods 0.000 claims description 15
- 238000000926 separation method Methods 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 9
- 239000012065 filter cake Substances 0.000 claims description 5
- -1 2-Methyl-1H-indole-3-yl Chemical group 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 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 abstract 1
- 239000000243 solution Substances 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- CPVSLHQIPGTMLH-UHFFFAOYSA-N 2-(2-methyl-1h-indol-3-yl)ethanamine Chemical compound C1=CC=C2C(CCN)=C(C)NC2=C1 CPVSLHQIPGTMLH-UHFFFAOYSA-N 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 150000003839 salts Chemical class 0.000 description 25
- 239000000047 product Substances 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000001816 cooling Methods 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- 150000002466 imines Chemical class 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- XVRIEWDDMODMGA-UHFFFAOYSA-N 5-chloropentan-2-one Chemical compound CC(=O)CCCCl XVRIEWDDMODMGA-UHFFFAOYSA-N 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 8
- 229940067157 phenylhydrazine Drugs 0.000 description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 description 8
- 239000012279 sodium borohydride Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 238000004896 high resolution mass spectrometry Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 102000003964 Histone deacetylase Human genes 0.000 description 1
- 108090000353 Histone deacetylase Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940121372 histone deacetylase inhibitor Drugs 0.000 description 1
- 239000003276 histone deacetylase inhibitor Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80452706P | 2006-06-12 | 2006-06-12 | |
| US60/804,527 | 2006-06-12 | ||
| US86787806P | 2006-11-30 | 2006-11-30 | |
| US60/867,878 | 2006-11-30 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007800217257A Division CN101466674A (zh) | 2006-06-12 | 2007-06-07 | N-羟基-3-[4-[[[2-(2-甲基-1h-吲哚-3-基)乙基]氨基]甲基]苯基]-2e-2-丙烯酰胺及其原料的制备方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103086944A true CN103086944A (zh) | 2013-05-08 |
Family
ID=38832681
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2012103501544A Pending CN103086944A (zh) | 2006-06-12 | 2007-06-07 | N-羟基-3-[4-[[[2-(2-甲基-1h-吲哚-3-基)乙基]氨基]甲基]苯基]-2e-2-丙烯酰胺的制备方法及其原料 |
| CNA2007800217257A Pending CN101466674A (zh) | 2006-06-12 | 2007-06-07 | N-羟基-3-[4-[[[2-(2-甲基-1h-吲哚-3-基)乙基]氨基]甲基]苯基]-2e-2-丙烯酰胺及其原料的制备方法 |
| CN2011100629486A Active CN102167678B (zh) | 2006-06-12 | 2007-06-07 | N-羟基-3-[4-[[[2-(2-甲基-1h-吲哚-3-基)乙基]氨基]甲基]苯基]-2e-2-丙烯酰胺及其原料的制备方法 |
| CN2011100630820A Pending CN102174008A (zh) | 2006-06-12 | 2007-06-07 | 一种制备2-甲基色胺的方法 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007800217257A Pending CN101466674A (zh) | 2006-06-12 | 2007-06-07 | N-羟基-3-[4-[[[2-(2-甲基-1h-吲哚-3-基)乙基]氨基]甲基]苯基]-2e-2-丙烯酰胺及其原料的制备方法 |
| CN2011100629486A Active CN102167678B (zh) | 2006-06-12 | 2007-06-07 | N-羟基-3-[4-[[[2-(2-甲基-1h-吲哚-3-基)乙基]氨基]甲基]苯基]-2e-2-丙烯酰胺及其原料的制备方法 |
| CN2011100630820A Pending CN102174008A (zh) | 2006-06-12 | 2007-06-07 | 一种制备2-甲基色胺的方法 |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US20090306405A1 (enExample) |
| EP (2) | EP2032533B8 (enExample) |
| JP (2) | JP5431926B2 (enExample) |
| KR (2) | KR101493530B1 (enExample) |
| CN (4) | CN103086944A (enExample) |
| AR (1) | AR061296A1 (enExample) |
| AU (1) | AU2007257883B2 (enExample) |
| BR (1) | BRPI0712847A2 (enExample) |
| CA (1) | CA2653657C (enExample) |
| CL (2) | CL2007001691A1 (enExample) |
| DK (1) | DK2032533T3 (enExample) |
| EC (1) | ECSP088978A (enExample) |
| ES (2) | ES2416286T3 (enExample) |
| GT (1) | GT200800282A (enExample) |
| HR (1) | HRP20130798T1 (enExample) |
| IL (2) | IL195211A (enExample) |
| IN (1) | IN2015DN00910A (enExample) |
| JO (1) | JO2900B1 (enExample) |
| MA (1) | MA30513B1 (enExample) |
| MX (2) | MX366213B (enExample) |
| MY (1) | MY147576A (enExample) |
| NO (1) | NO341870B1 (enExample) |
| NZ (1) | NZ572707A (enExample) |
| PE (2) | PE20080851A1 (enExample) |
| PL (1) | PL2032533T3 (enExample) |
| PT (1) | PT2032533E (enExample) |
| RU (1) | RU2448090C2 (enExample) |
| TN (1) | TNSN08507A1 (enExample) |
| TW (1) | TWI395734B (enExample) |
| WO (1) | WO2007146718A2 (enExample) |
| ZA (1) | ZA200809490B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT202000004075A1 (it) | 2020-02-27 | 2021-08-27 | Flamma Spa | Processo per la preparazione di panobinostat |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB146260A (en) | 1918-07-11 | 1921-08-11 | Elektro Osmose Ag | A process for preparing proteids charged with immune substances |
| GB8531612D0 (en) * | 1985-12-23 | 1986-02-05 | Beecham Wuelfing Gmbh & Co Kg | Compounds |
| PE20020354A1 (es) * | 2000-09-01 | 2002-06-12 | Novartis Ag | Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda) |
| AU2002237261A1 (en) | 2001-01-09 | 2002-07-24 | Novartis Pharma Gmbh | Rapid method for screening compounds for in vivo activity |
| KR100937064B1 (ko) | 2001-11-06 | 2010-01-15 | 노파르티스 아게 | 시클로옥시게나제-2 억제제/히스톤 데아세틸라제 억제제복합제제 |
| MY147013A (en) * | 2006-06-12 | 2012-10-15 | Novartis Ag | Process for making salts of n-hydroxy-3-[4-[[[2-(2-methyl-1h-indol-3-yl)ethyl]amino]methyl]phenyl]-2e-2-propenamide |
-
2007
- 2007-06-07 IN IN910DEN2015 patent/IN2015DN00910A/en unknown
- 2007-06-07 CN CN2012103501544A patent/CN103086944A/zh active Pending
- 2007-06-07 US US12/302,572 patent/US20090306405A1/en not_active Abandoned
- 2007-06-07 RU RU2008151726/04A patent/RU2448090C2/ru active
- 2007-06-07 PL PL07784350T patent/PL2032533T3/pl unknown
- 2007-06-07 CA CA2653657A patent/CA2653657C/en active Active
- 2007-06-07 KR KR20087030232A patent/KR101493530B1/ko not_active Expired - Fee Related
- 2007-06-07 KR KR1020147026120A patent/KR101540194B1/ko not_active Expired - Fee Related
- 2007-06-07 NZ NZ572707A patent/NZ572707A/en not_active IP Right Cessation
- 2007-06-07 MX MX2012002221A patent/MX366213B/es unknown
- 2007-06-07 HR HRP20130798TT patent/HRP20130798T1/hr unknown
- 2007-06-07 WO PCT/US2007/070564 patent/WO2007146718A2/en not_active Ceased
- 2007-06-07 JP JP2009515575A patent/JP5431926B2/ja active Active
- 2007-06-07 DK DK07784350.6T patent/DK2032533T3/da active
- 2007-06-07 EP EP07784350.6A patent/EP2032533B8/en active Active
- 2007-06-07 CN CNA2007800217257A patent/CN101466674A/zh active Pending
- 2007-06-07 CN CN2011100629486A patent/CN102167678B/zh active Active
- 2007-06-07 EP EP11179043.2A patent/EP2394991B1/en active Active
- 2007-06-07 PT PT77843506T patent/PT2032533E/pt unknown
- 2007-06-07 ES ES07784350T patent/ES2416286T3/es active Active
- 2007-06-07 BR BRPI0712847-9A patent/BRPI0712847A2/pt not_active IP Right Cessation
- 2007-06-07 CN CN2011100630820A patent/CN102174008A/zh active Pending
- 2007-06-07 ES ES11179043.2T patent/ES2553255T3/es active Active
- 2007-06-07 AU AU2007257883A patent/AU2007257883B2/en not_active Ceased
- 2007-06-07 MX MX2008015898A patent/MX2008015898A/es active IP Right Grant
- 2007-06-08 PE PE2007000720A patent/PE20080851A1/es active IP Right Grant
- 2007-06-08 AR ARP070102498A patent/AR061296A1/es unknown
- 2007-06-08 PE PE2011002097A patent/PE20120221A1/es active IP Right Grant
- 2007-06-11 TW TW096120985A patent/TWI395734B/zh not_active IP Right Cessation
- 2007-06-11 CL CL200701691A patent/CL2007001691A1/es unknown
- 2007-06-12 JO JO2007219A patent/JO2900B1/en active
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2008
- 2008-11-06 ZA ZA200809490A patent/ZA200809490B/xx unknown
- 2008-11-10 IL IL195211A patent/IL195211A/en active IP Right Grant
- 2008-11-28 MY MYPI20084865A patent/MY147576A/en unknown
- 2008-12-05 TN TNP2008000507A patent/TNSN08507A1/en unknown
- 2008-12-10 GT GT200800282A patent/GT200800282A/es unknown
- 2008-12-12 EC EC2008008978A patent/ECSP088978A/es unknown
- 2008-12-12 MA MA31472A patent/MA30513B1/fr unknown
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2009
- 2009-01-09 NO NO20090137A patent/NO341870B1/no not_active IP Right Cessation
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2010
- 2010-09-13 CL CL2010000973A patent/CL2010000973A1/es unknown
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2011
- 2011-09-23 US US13/243,001 patent/US8536346B2/en active Active
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2013
- 2013-10-25 JP JP2013222442A patent/JP5809223B2/ja active Active
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2014
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