HRP20110575T1 - Postupak pročišćavanja montelukasta i njegovih soli amina - Google Patents
Postupak pročišćavanja montelukasta i njegovih soli amina Download PDFInfo
- Publication number
- HRP20110575T1 HRP20110575T1 HR20110575T HRP20110575T HRP20110575T1 HR P20110575 T1 HRP20110575 T1 HR P20110575T1 HR 20110575 T HR20110575 T HR 20110575T HR P20110575 T HRP20110575 T HR P20110575T HR P20110575 T1 HRP20110575 T1 HR P20110575T1
- Authority
- HR
- Croatia
- Prior art keywords
- montelukast
- salt
- purification process
- process according
- solvent
- Prior art date
Links
- 229960005127 montelukast Drugs 0.000 title claims abstract 19
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 title claims abstract 18
- 238000000746 purification Methods 0.000 title claims abstract 13
- -1 amine salts Chemical class 0.000 title claims abstract 6
- 239000000203 mixture Substances 0.000 claims abstract 12
- 150000003839 salts Chemical class 0.000 claims abstract 11
- 239000012453 solvate Substances 0.000 claims abstract 8
- 239000002904 solvent Substances 0.000 claims abstract 8
- 239000002253 acid Substances 0.000 claims abstract 6
- 238000000034 method Methods 0.000 claims abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 239000008346 aqueous phase Substances 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 4
- 238000009835 boiling Methods 0.000 claims 4
- 238000000605 extraction Methods 0.000 claims 4
- 238000005406 washing Methods 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- JUCGVCVPNPBJIG-IUCAKERBSA-N (1s,2s)-2-amino-1-phenylpropane-1,3-diol Chemical compound OC[C@H](N)[C@@H](O)C1=CC=CC=C1 JUCGVCVPNPBJIG-IUCAKERBSA-N 0.000 claims 2
- IJXJGQCXFSSHNL-MRVPVSSYSA-N (2s)-2-amino-2-phenylethanol Chemical class OC[C@@H](N)C1=CC=CC=C1 IJXJGQCXFSSHNL-MRVPVSSYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 150000002500 ions Chemical class 0.000 claims 2
- 239000012074 organic phase Substances 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 159000000000 sodium salts Chemical group 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 abstract 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/18—Halogen atoms or nitro radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4704—2-Quinolinones, e.g. carbostyril
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Postupak za pročišćavanje Montelukasta, ili njegove farmaceutski prihvatljive soli, ili njegovog solvata, uključujući bilo koji stereoizomer ili njegovu mješavinu naznačen time da se sastoji od pretvaranja kiseline Montelukasta ili njegovog solvata, uključujući bilo koji stereoizomer ili njegovu mješavinu, u sol amina koja je odabrana iz skupine koju čine L-(+)-treo-2-amino-1-fenil-1,3-propandiol i sol L-(+)-α-fenilglicinola, u prisutnosti odgovarajućeg otapala. Patent sadrži još 14 patentnih zahtjeva.
Claims (15)
1. Postupak za pročišćavanje Montelukasta, ili njegove farmaceutski prihvatljive soli, ili njegovog solvata, uključujući bilo koji stereoizomer ili njegovu mješavinu naznačen time da se sastoji od pretvaranja kiseline Montelukasta ili njegovog solvata, uključujući bilo koji stereoizomer ili njegovu mješavinu, u sol amina koja je odabrana iz skupine koju čine L-(+)-treo-2-amino-1-fenil-1,3-propandiol i sol L-(+)-α-fenilglicinola, u prisutnosti odgovarajućeg otapala.
2. Postupak pročišćavanja prema zahtjevu 1, naznačen time da sol L-(+)-α- fenilglicinola Montelukasta je solvat odabran iz skupine koju čine metanol, etanol i 2-propanol solvat.
3. Postupak pročišćavanja prema bilo kojem od zahtjeva 1-2, naznačen time da je otapalo odabrano iz skupine koju čine (C2-C8)- eter, (C4-C8)-alkil ester, (C6-C8)-aromatski ugljikovodik; (C6-C8)-ne aromatski ugljikovodik, (C2-C5)-alkohol, i njihove mješavine.
4. Postupak pročišćavanja prema zahtjevu 3, naznačen time da je otapalo odabrano od toluena, etil acetata, etanola, 2-propanola, i njihovih mješavina.
5. Postupak pročišćavanja prema bilo kojem od zahtjeva 1-4, naznačen time da nadalje sadrži postupak prethodnog pročišćavanja koji sadrži provođenje specifičnog skupa selektivnih ekstrakcija Montelukasta u otapalu ili njegovih nečistoća, te navedeni skup ekstrakcija u otapalu sadrži barem jedno ispiranje vodene faze koja sadrži sirovi Montelukast u obliku soli sa organskim otapalom, uz pH koji je između 12.0 i 13.5 i pri temperaturi koja je između 10 °C i oko 5 °C ispod točke vrenja mješavine.
6. Postupak pročišćavanja prema zahtjevu 5, naznačen time da skup ekstrakcija u otapalu sadrži slijedeće korake:
a) provođenje barem jednog ispiranja vodene faze koja sadrži sirovi Montelukast u obliku soli sa organskim otapalom, uz pH koji je između 12.0 i 13.5 i pri temperaturi koja je između 10 °C i oko 5 °C ispod točke vrenja mješavine, te odvajanje vodene faze koja sadrži Montelukast u obliku soli;
b) proizvoljno, provođenje jednog ili više ispiranja vodene faze iz koraka (a) sa organskim otapalom uz pH koji je između 8.5 i 10.0 i pri temperaturi koja je između 10 °C i oko 5 °C ispod točke vrenja mješavine, te odvajanje vodene faze koja sadrži Montelukast u obliku soli;
c) provođenje ekstrakcije pročišćenog Montelukasta iz vodene faze iz koraka (a) ili (b) sa organskim otapalom uz pH koji je između 4.5 i 8.0 i pri temperaturi koja je između 10 °C i oko 5 °C ispod točke vrenja mješavine, te odvajanje organske faze kiselinu Montelukasta; te
d) proizvoljno, izdvajanje Montelukasta iz organske faze iz koraka (c) kao kiseline.
7. Postupak pročišćavanja prema bilo kojem od zahtjeva 5-6, naznačen time da je organsko otapalo odabrano iz skupine koju čine (C2-C8)-eter, (C6-C8)-aromatski ugljikovodik; otapala koja sadrže (C1-C3)-klor, i njihove mješavine.
8. Postupak pročišćavanja prema zahtjevu 7, naznačen time da je otapalo odabrano od toluena, terc-butil metil etera, tetrahidrofurana, i njihovih mješavina.
9. Postupak pročišćavanja prema bilo kojem od zahtjeva 5-8, naznačen time da su barem dva ispiranja provedena uz pH koji je između 12.0-13.5 i pri temperaturi koja je između 20 i 60°C.
10. Postupak pročišćavanja prema bilo kojem od zahtjeva 5-9 naznačen time da su ekstrakcije iz koraka (b) provedene uz pH jednak 9.0-9.5, te pri temperaturi koja je između 20 i 60°C.
11. Postupak pročišćavanja prema bilo kojem od prethodnih zahtjeva, naznačen time da sadrži:
a) obradu soli amina Montelukasta kako je definirano u zahtjevu 1 sa kiselinom, da se dobije Montelukast kiselina; i proizvoljno,
b) obradu tako dobivenog produkta sa izvorom iona i odvajanje odgovarajuće farmaceutski prihvatljive soli.
12. Postupak prema zahtjevu 11, naznačen time da ion je natrij i farmaceutski prihvatljiva sol je natrijeva sol.
13. Spoj naznačen time da je sol L-(+)-treo-2-amino-1-fenil-1,3-propandiola Montelukasta.
14. Spoj naznačen time da je sol L-(+)-α-fenilglicinola Montelukasta.
15. Solvat soli L-(+)-α- fenilglicinola Montelukasta naznačen time da je odabran iz skupine koju čine metanol, etanol i 2-propanol solvat.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83685606P | 2006-08-09 | 2006-08-09 | |
| EP06118690A EP1886998A1 (en) | 2006-08-09 | 2006-08-09 | Purification process of montelukast and its amine salts |
| PCT/EP2007/058180 WO2008017669A1 (en) | 2006-08-09 | 2007-08-07 | Purification process of montelukast and its amine salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110575T1 true HRP20110575T1 (hr) | 2011-09-30 |
Family
ID=37625598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110575T HRP20110575T1 (hr) | 2006-08-09 | 2011-08-02 | Postupak pročišćavanja montelukasta i njegovih soli amina |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8188285B2 (hr) |
| EP (2) | EP1886998A1 (hr) |
| JP (1) | JP5188501B2 (hr) |
| KR (1) | KR20090035696A (hr) |
| CN (1) | CN101501000B (hr) |
| AT (1) | ATE515498T1 (hr) |
| AU (1) | AU2007283615A1 (hr) |
| CA (1) | CA2657775A1 (hr) |
| ES (1) | ES2372414T3 (hr) |
| HR (1) | HRP20110575T1 (hr) |
| IL (1) | IL196303A (hr) |
| MX (1) | MX2009000524A (hr) |
| NO (1) | NO20091051L (hr) |
| PL (1) | PL2077996T3 (hr) |
| PT (1) | PT2077996E (hr) |
| RU (1) | RU2009108272A (hr) |
| SI (1) | SI2077996T1 (hr) |
| WO (1) | WO2008017669A1 (hr) |
| ZA (1) | ZA200900890B (hr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7812168B2 (en) | 2005-07-05 | 2010-10-12 | Teva Pharmaceutical Industries Ltd. | Purification of montelukast |
| KR101469015B1 (ko) * | 2008-02-25 | 2014-12-05 | 주식회사 종근당 | 몬테루카스트의 제조방법 및 이에 사용되는 중간체 |
| EP2265586A4 (en) * | 2008-03-17 | 2012-10-03 | Reddys Lab Ltd Dr | PREPARATION OF MONTELUKAST AND ITS SALTS |
| KR101123292B1 (ko) * | 2008-09-26 | 2012-03-19 | 주식회사 엘지생명과학 | 몬테루카스트 나트륨염의 제조방법 |
| WO2011121091A1 (en) | 2010-03-31 | 2011-10-06 | Krka, D.D., Novo Mesto | Efficient synthesis for the preparation of montelukast and novel crystalline form of intermediates therein |
| KR100990046B1 (ko) * | 2010-07-30 | 2010-10-26 | 동국제약 주식회사 | 신규한 몬테루카스트 4-할로 벤질아민염 및 이를 이용한 몬테루카스트 나트륨염의 제조방법 |
| HUP1000425A2 (en) | 2010-08-11 | 2012-03-28 | Richter Gedeon Nyrt | Process for the production of montelukast sodium |
| WO2012077133A1 (en) * | 2010-12-07 | 2012-06-14 | Ind-Swift Laboratories Limited | Processes for preparation of montelukast sodium and purification of diol intermediate |
| CN102060762B (zh) * | 2011-01-28 | 2013-05-29 | 海南美大制药有限公司 | 孟鲁司特化合物及其新制法 |
| CN103570618A (zh) * | 2013-09-30 | 2014-02-12 | 浙江车头制药股份有限公司 | 一种孟鲁司特钠盐的制备方法 |
| CN105646344B (zh) * | 2016-02-29 | 2018-08-14 | 山东新时代药业有限公司 | 一种孟鲁司特的纯化方法 |
| CN105585524B (zh) * | 2016-02-29 | 2018-03-02 | 山东新时代药业有限公司 | 一种由孟鲁司特酸制备孟鲁司特钠的方法 |
| CN105924392B (zh) * | 2016-02-29 | 2018-03-02 | 山东新时代药业有限公司 | 一种孟鲁司特钠制备方法 |
| JP7236433B2 (ja) * | 2017-07-24 | 2023-03-09 | インテルキム、ソシエダッド アノニマ | Ｌｆａ－１拮抗薬リフィテグラストを調製および精製するためのプロセス |
| CN112789037A (zh) | 2018-09-06 | 2021-05-11 | 创新药物筛选有限公司 | 用于治疗哮喘或帕金森病的方法和药物组合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8403224A (nl) * | 1984-10-24 | 1986-05-16 | Oce Andeno Bv | Dioxafosforinanen, de bereiding ervan en de toepassing voor het splitsen van optisch actieve verbindingen. |
| EP0480717B1 (en) * | 1990-10-12 | 1998-04-15 | Merck Frosst Canada Inc. | Unsaturated hydroxyalkylquinoline acids as leukotriene antagonists |
| TW448160B (en) * | 1993-12-28 | 2001-08-01 | Merck & Co Inc | Novel dicyclohexylamine salt and process for the preparation of leukotriene antagonists |
| CN1420113A (zh) | 2001-11-16 | 2003-05-28 | 北京上地新世纪生物医药研究所 | 孟鲁司特钠的制备方法及其制备中间体 |
| CN1171873C (zh) | 2001-12-26 | 2004-10-20 | 北京上地新世纪生物医药研究所 | 一种孟鲁司特钠的制备方法及其制备中间体 |
| US20050107612A1 (en) * | 2002-12-30 | 2005-05-19 | Dr. Reddy's Laboratories Limited | Process for preparation of montelukast and its salts |
| US8450491B2 (en) * | 2003-06-06 | 2013-05-28 | Morepen Laboratories Limited | Method for the preparation of montelukast acid and sodium salt thereof in amorphous form |
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| US7189853B2 (en) * | 2004-04-15 | 2007-03-13 | Dr. Reddy's Laboratories Limited | Process for the preparation of [R-(E)-1-[[[1-[3-[2-[7-chloro-2-quinolinyl]ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid (Montelukast) and its pharmaceutically acceptable salts |
| MXPA06012220A (es) | 2004-04-21 | 2007-07-18 | Teva Pharma | Procesos para preparar sodio de montelukast. |
| US7501517B2 (en) | 2004-04-30 | 2009-03-10 | Synthon Ip, Inc. | Process for making montelukast and intermediates therefor |
| US7829716B2 (en) | 2004-04-30 | 2010-11-09 | Synthon Pharmaceuticals, Inc. | Process for making montelukast and intermediates therefor |
| US20090143590A1 (en) * | 2004-07-19 | 2009-06-04 | Matrix Laboratories Ltd. | Process for the Preparation of Montelukast and its Salts |
| PL205637B1 (pl) * | 2004-10-22 | 2010-05-31 | Inst Farmaceutyczny | Sposób wytwarzania kwasu (R,E)-(1-{1-{3-[2-(7-chlorochinolin-2-ylo)etenylo]fenylo}-3-[2-(1-hydroksy-1-metyloetylo)fenylo] propylosulfanylometylo}cyklopropylo)octowego i/lub jego farmaceutycznie dopuszczalnych soli |
| WO2007004237A2 (en) | 2005-07-05 | 2007-01-11 | Matrix Laboratories Ltd | A process for the preparation of montelukast |
| US7812168B2 (en) | 2005-07-05 | 2010-10-12 | Teva Pharmaceutical Industries Ltd. | Purification of montelukast |
| EP1912499A4 (en) | 2005-07-20 | 2010-03-31 | Reddys Lab Ltd Dr | PREPARATION OF MONTELUKAST |
| EP1968943B1 (en) | 2005-12-13 | 2013-01-23 | MSN Laboratories Limited | An improved process for the preparation of montelukast and its pharmaceutically acceptable salts |
| CA2632954A1 (en) | 2005-12-23 | 2007-06-28 | Glade Organics Private Limited | An improved process for the manufacture of montelukast sodium |
| CA2643228A1 (en) | 2006-02-21 | 2007-08-30 | Chemagis Ltd. | Novel polymorphs of montelukast ammonium salts and processes for preparation therefor |
| WO2007096889A2 (en) | 2006-02-27 | 2007-08-30 | Chemagis Ltd. | Process for preparing montelukast and salts thereof |
| EP1996552A1 (en) | 2006-03-17 | 2008-12-03 | Synthon B.V. | Montelukast amantadine salt |
| CA2649189A1 (en) | 2006-04-12 | 2007-10-18 | Glade Organics Private Limited | An improved process for the manufacture of montelukast sodium |
| WO2008001213A1 (en) | 2006-06-26 | 2008-01-03 | Aurobindo Pharma Limited | An improved process for the preparation of leukotriene receptor antagonist (montelukast sodium) |
| GB0614485D0 (en) | 2006-07-21 | 2006-09-27 | Pliva Istrazivanje I Razvoj D | Process |
| EP2069307A4 (en) | 2006-08-04 | 2010-03-03 | Matrix Lab Ltd | PROCESS FOR THE PREPARATION OF MONTELUKAST AND ITS SALTS |
-
2006
- 2006-08-09 EP EP06118690A patent/EP1886998A1/en not_active Withdrawn
-
2007
- 2007-08-07 RU RU2009108272/04A patent/RU2009108272A/ru not_active Application Discontinuation
- 2007-08-07 ZA ZA200900890A patent/ZA200900890B/xx unknown
- 2007-08-07 SI SI200730709T patent/SI2077996T1/sl unknown
- 2007-08-07 PT PT07788281T patent/PT2077996E/pt unknown
- 2007-08-07 MX MX2009000524A patent/MX2009000524A/es active IP Right Grant
- 2007-08-07 ES ES07788281T patent/ES2372414T3/es active Active
- 2007-08-07 US US12/376,779 patent/US8188285B2/en not_active Expired - Fee Related
- 2007-08-07 AT AT07788281T patent/ATE515498T1/de not_active IP Right Cessation
- 2007-08-07 KR KR1020097002477A patent/KR20090035696A/ko not_active Application Discontinuation
- 2007-08-07 EP EP07788281A patent/EP2077996B1/en active Active
- 2007-08-07 WO PCT/EP2007/058180 patent/WO2008017669A1/en active Application Filing
- 2007-08-07 CN CN2007800295684A patent/CN101501000B/zh not_active Expired - Fee Related
- 2007-08-07 PL PL07788281T patent/PL2077996T3/pl unknown
- 2007-08-07 CA CA002657775A patent/CA2657775A1/en not_active Abandoned
- 2007-08-07 JP JP2009523276A patent/JP5188501B2/ja not_active Expired - Fee Related
- 2007-08-07 AU AU2007283615A patent/AU2007283615A1/en not_active Abandoned
-
2008
- 2008-12-31 IL IL196303A patent/IL196303A/en not_active IP Right Cessation
-
2009
- 2009-03-09 NO NO20091051A patent/NO20091051L/no not_active Application Discontinuation
-
2011
- 2011-08-02 HR HR20110575T patent/HRP20110575T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2657775A1 (en) | 2008-02-14 |
| JP2010500325A (ja) | 2010-01-07 |
| CN101501000A (zh) | 2009-08-05 |
| SI2077996T1 (sl) | 2011-10-28 |
| US8188285B2 (en) | 2012-05-29 |
| US20090247759A1 (en) | 2009-10-01 |
| RU2009108272A (ru) | 2010-09-20 |
| ZA200900890B (en) | 2010-04-28 |
| CN101501000B (zh) | 2012-04-04 |
| IL196303A (en) | 2014-03-31 |
| MX2009000524A (es) | 2009-01-27 |
| JP5188501B2 (ja) | 2013-04-24 |
| EP2077996A1 (en) | 2009-07-15 |
| EP1886998A1 (en) | 2008-02-13 |
| NO20091051L (no) | 2009-05-05 |
| ES2372414T3 (es) | 2012-01-19 |
| WO2008017669A1 (en) | 2008-02-14 |
| EP2077996B1 (en) | 2011-07-06 |
| KR20090035696A (ko) | 2009-04-10 |
| AU2007283615A1 (en) | 2008-02-14 |
| ATE515498T1 (de) | 2011-07-15 |
| PT2077996E (pt) | 2011-09-13 |
| PL2077996T3 (pl) | 2011-11-30 |
| IL196303A0 (en) | 2009-09-22 |
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