CA2653657C - Process for making n-hydroxy-3-[4-[[[2-(2-methyl-1h-indol-3-yl)ethyl]amino]methyl]phenyl]-2e-2-propenamide and starting materials therefor - Google Patents
Process for making n-hydroxy-3-[4-[[[2-(2-methyl-1h-indol-3-yl)ethyl]amino]methyl]phenyl]-2e-2-propenamide and starting materials therefor Download PDFInfo
- Publication number
- CA2653657C CA2653657C CA2653657A CA2653657A CA2653657C CA 2653657 C CA2653657 C CA 2653657C CA 2653657 A CA2653657 A CA 2653657A CA 2653657 A CA2653657 A CA 2653657A CA 2653657 C CA2653657 C CA 2653657C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- phenyl
- propenamide
- hydroxy
- 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.)
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Links
- 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 claims abstract 9
- 238000000034 method Methods 0.000 title claims description 48
- 239000007858 starting material Substances 0.000 title abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 69
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 54
- 239000000725 suspension Substances 0.000 claims description 46
- 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 claims description 42
- 239000011541 reaction mixture Substances 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- 238000003756 stirring Methods 0.000 claims description 25
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 22
- 239000000706 filtrate Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000001914 filtration Methods 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 16
- 238000001035 drying Methods 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000013078 crystal Substances 0.000 claims description 7
- 239000012065 filter cake Substances 0.000 claims description 7
- XVXVAVCOKYEXMZ-ZHACJKMWSA-N (e)-3-[4-[[2-(2-methyl-1h-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enoic acid Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(\C=C\C(O)=O)C=C1 XVXVAVCOKYEXMZ-ZHACJKMWSA-N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 1
- 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 abstract description 29
- SLJZCNYOFBVRSA-CALJPSDSSA-N methyl (e)-3-[4-[[2-(2-methyl-1h-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enoate;hydrochloride Chemical compound Cl.C1=CC(/C=C/C(=O)OC)=CC=C1CNCCC1=C(C)NC2=CC=CC=C12 SLJZCNYOFBVRSA-CALJPSDSSA-N 0.000 abstract 1
- 238000010189 synthetic method Methods 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
- 239000000243 solution Substances 0.000 description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
- 239000000047 product Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 10
- XVRIEWDDMODMGA-UHFFFAOYSA-N 5-chloropentan-2-one Chemical compound CC(=O)CCCCl XVRIEWDDMODMGA-UHFFFAOYSA-N 0.000 description 9
- 150000002466 imines Chemical class 0.000 description 9
- 230000015572 biosynthetic process Effects 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- -1 e.g. Substances 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
- 229910052742 iron Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- KVXMLLMZXPRPNG-VOTSOKGWSA-N methyl (e)-3-(4-formylphenyl)prop-2-enoate Chemical compound COC(=O)\C=C\C1=CC=C(C=O)C=C1 KVXMLLMZXPRPNG-VOTSOKGWSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- QGPZUMRNTJFXOL-UHFFFAOYSA-N 2-(2-methyl-1h-indol-3-yl)ethanamine;hydrochloride Chemical compound Cl.C1=CC=C2C(CCN)=C(C)NC2=C1 QGPZUMRNTJFXOL-UHFFFAOYSA-N 0.000 description 1
- 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
- NCIKQJBVUNUXLW-UHFFFAOYSA-N N-methyltryptamine Chemical compound C1=CC=C2C(CCNC)=CNC2=C1 NCIKQJBVUNUXLW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229940121372 histone deacetylase inhibitor Drugs 0.000 description 1
- 239000003276 histone deacetylase inhibitor Substances 0.000 description 1
- 125000000879 imine group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000010792 warming Methods 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
Landscapes
- 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 (5)
| 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 | ||
| PCT/US2007/070564 WO2007146718A2 (en) | 2006-06-12 | 2007-06-07 | Process for making n-hydroxy-3-[4-[[[2-(2-methyl-1h-indol-3-yl)ethyl]amino] methyl]phenyl]-2e-2-propenamide and starting materials therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2653657A1 CA2653657A1 (en) | 2007-12-21 |
| CA2653657C true CA2653657C (en) | 2015-10-27 |
Family
ID=38832681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2653657A Active CA2653657C (en) | 2006-06-12 | 2007-06-07 | Process for making n-hydroxy-3-[4-[[[2-(2-methyl-1h-indol-3-yl)ethyl]amino]methyl]phenyl]-2e-2-propenamide and starting materials therefor |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US20090306405A1 (OSRAM) |
| EP (2) | EP2394991B1 (OSRAM) |
| JP (2) | JP5431926B2 (OSRAM) |
| KR (2) | KR101493530B1 (OSRAM) |
| CN (4) | CN101466674A (OSRAM) |
| AR (1) | AR061296A1 (OSRAM) |
| AU (1) | AU2007257883B2 (OSRAM) |
| BR (1) | BRPI0712847A2 (OSRAM) |
| CA (1) | CA2653657C (OSRAM) |
| CL (2) | CL2007001691A1 (OSRAM) |
| DK (1) | DK2032533T3 (OSRAM) |
| EC (1) | ECSP088978A (OSRAM) |
| ES (2) | ES2553255T3 (OSRAM) |
| GT (1) | GT200800282A (OSRAM) |
| HR (1) | HRP20130798T1 (OSRAM) |
| IL (2) | IL195211A (OSRAM) |
| IN (1) | IN2015DN00910A (OSRAM) |
| JO (1) | JO2900B1 (OSRAM) |
| MA (1) | MA30513B1 (OSRAM) |
| MX (2) | MX2008015898A (OSRAM) |
| MY (1) | MY147576A (OSRAM) |
| NO (1) | NO341870B1 (OSRAM) |
| NZ (1) | NZ572707A (OSRAM) |
| PE (2) | PE20120221A1 (OSRAM) |
| PL (1) | PL2032533T3 (OSRAM) |
| PT (1) | PT2032533E (OSRAM) |
| RU (1) | RU2448090C2 (OSRAM) |
| TN (1) | TNSN08507A1 (OSRAM) |
| TW (1) | TWI395734B (OSRAM) |
| WO (1) | WO2007146718A2 (OSRAM) |
| ZA (1) | ZA200809490B (OSRAM) |
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) |
| JP2004517334A (ja) | 2001-01-09 | 2004-06-10 | ノバルティス アクチエンゲゼルシャフト | 化合物のインビボ活性をスクリーニングする迅速な方法 |
| AU2002351844B2 (en) | 2001-11-06 | 2006-12-21 | Novartis Ag | Cyclooxygenase-2 inhibitor/histone deacetylase inhibitor combination |
| 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 CA CA2653657A patent/CA2653657C/en active Active
- 2007-06-07 EP EP11179043.2A patent/EP2394991B1/en active Active
- 2007-06-07 ES ES11179043.2T patent/ES2553255T3/es active Active
- 2007-06-07 KR KR20087030232A patent/KR101493530B1/ko not_active Expired - Fee Related
- 2007-06-07 PL PL07784350T patent/PL2032533T3/pl unknown
- 2007-06-07 NZ NZ572707A patent/NZ572707A/en not_active IP Right Cessation
- 2007-06-07 BR BRPI0712847-9A patent/BRPI0712847A2/pt not_active IP Right Cessation
- 2007-06-07 WO PCT/US2007/070564 patent/WO2007146718A2/en not_active Ceased
- 2007-06-07 ES ES07784350T patent/ES2416286T3/es active Active
- 2007-06-07 MX MX2008015898A patent/MX2008015898A/es active IP Right Grant
- 2007-06-07 CN CNA2007800217257A patent/CN101466674A/zh active Pending
- 2007-06-07 EP EP07784350.6A patent/EP2032533B8/en active Active
- 2007-06-07 CN CN2012103501544A patent/CN103086944A/zh active Pending
- 2007-06-07 AU AU2007257883A patent/AU2007257883B2/en not_active Ceased
- 2007-06-07 KR KR1020147026120A patent/KR101540194B1/ko not_active Expired - Fee Related
- 2007-06-07 CN CN2011100630820A patent/CN102174008A/zh active Pending
- 2007-06-07 DK DK07784350.6T patent/DK2032533T3/da active
- 2007-06-07 CN CN2011100629486A patent/CN102167678B/zh active Active
- 2007-06-07 MX MX2012002221A patent/MX366213B/es unknown
- 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 PT PT77843506T patent/PT2032533E/pt unknown
- 2007-06-07 HR HRP20130798TT patent/HRP20130798T1/hr unknown
- 2007-06-07 JP JP2009515575A patent/JP5431926B2/ja active Active
- 2007-06-08 PE PE2011002097A patent/PE20120221A1/es active IP Right Grant
- 2007-06-08 AR ARP070102498A patent/AR061296A1/es unknown
- 2007-06-08 PE PE2007000720A patent/PE20080851A1/es active IP Right Grant
- 2007-06-11 CL CL200701691A patent/CL2007001691A1/es unknown
- 2007-06-11 TW TW096120985A patent/TWI395734B/zh not_active IP Right Cessation
- 2007-06-12 JO JO2007219A patent/JO2900B1/en active
-
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
-
2009
- 2009-01-09 NO NO20090137A patent/NO341870B1/no not_active IP Right Cessation
-
2010
- 2010-09-13 CL CL2010000973A patent/CL2010000973A1/es unknown
-
2011
- 2011-09-23 US US13/243,001 patent/US8536346B2/en active Active
-
2013
- 2013-10-25 JP JP2013222442A patent/JP5809223B2/ja active Active
-
2014
- 2014-07-28 IL IL233836A patent/IL233836A/en active IP Right Grant
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