CA2546701A1 - Crystalline ammonium salts of rosuvastatin - Google Patents
Crystalline ammonium salts of rosuvastatin Download PDFInfo
- Publication number
- CA2546701A1 CA2546701A1 CA002546701A CA2546701A CA2546701A1 CA 2546701 A1 CA2546701 A1 CA 2546701A1 CA 002546701 A CA002546701 A CA 002546701A CA 2546701 A CA2546701 A CA 2546701A CA 2546701 A1 CA2546701 A1 CA 2546701A1
- Authority
- CA
- Canada
- Prior art keywords
- rosuvastatin
- salt
- calcium
- combining
- crystalline form
- 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.)
- Granted
Links
- 229960000672 rosuvastatin Drugs 0.000 title claims abstract 19
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical class CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 title claims abstract 14
- 150000003863 ammonium salts Chemical class 0.000 title claims 4
- 238000000034 method Methods 0.000 claims 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 23
- LALFOYNTGMUKGG-BGRFNVSISA-L rosuvastatin calcium Chemical compound [Ca+2].CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O.CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O LALFOYNTGMUKGG-BGRFNVSISA-L 0.000 claims 18
- 239000002253 acid Substances 0.000 claims 17
- 229960004796 rosuvastatin calcium Drugs 0.000 claims 16
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 14
- 239000002904 solvent Substances 0.000 claims 13
- 159000000007 calcium salts Chemical class 0.000 claims 10
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims 10
- 239000003960 organic solvent Substances 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 9
- 229940093499 ethyl acetate Drugs 0.000 claims 8
- 235000019439 ethyl acetate Nutrition 0.000 claims 8
- 238000001704 evaporation Methods 0.000 claims 8
- 238000001816 cooling Methods 0.000 claims 7
- 239000012074 organic phase Substances 0.000 claims 6
- -1 rosuvastatin isopropylammonium salt Chemical class 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims 5
- 230000008020 evaporation Effects 0.000 claims 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 229910052791 calcium Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 150000003946 cyclohexylamines Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000005210 alkyl ammonium group Chemical group 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Abstract
Provided are alkyl ammonium crystalline salts of rosuvastatin that provide for purification of rosuvastatin and its pharmaceutically acceptable salts.
Claims (56)
1. Crystalline rosuvastatin isopropylammonium salt.
2. A crystalline form of rosuvastatin isopropylammonium salt having an X-ray powder diffraction pattern with peaks at 6.2, 18.8, 19.3, 20.6 and 22.3 ~0.2 deg. 2-theta.
3. The crystalline form of claim 2, further having peaks at 6.0, 10.2, 10.6, 13.4, 15.6, 16.6, 18.2, 27.3 and 28.8 ~0.2 deg. 2-theta.
4. The crystalline form of claim 3, wherein the crystalline form has an X-ray powder diffraction pattern substantially as depicted in Figure 1.
5. A process for preparing a crystalline form of claim 2 comprising combining a solution of rosuvastatin acid in an organic solvent with isopropylamine to precipitate the crystalline form and recovering the crystalline form.
6. The process of claim 5, wherein precipitation is induced by cooling the solution to a temperature of less than about 10°C.
7. The process of claim 5, wherein the combining is at a temperature of about 20°C to about 40°C.
8. The process of claim ?, wherein the temperature is about 30°C.
9. The process of claim 5, wherein the solvent is acetonitrile or ethyl acetate.
10. A process for preparing a crystalline form of claim 2 comprising combining a solution of rosuvastatin acid in acetonitrile or ethyl acetate with isopropylamine followed by stirring at a temperature of about 30°C, followed by cooling to a temperature of less than about 10°C to precipitate the crystalline form and recovering the crystalline form.
11. A process for purifying rosuvastatin calcium comprising a) converting rosuvastatin calcium salt to rosuvastatin acid;
b) converting rosuvastatin acid to the isopropylammonium salt of claim 2;
c) converting the isopropylammonium salt to rosuvastatin calcium.
b) converting rosuvastatin acid to the isopropylammonium salt of claim 2;
c) converting the isopropylammonium salt to rosuvastatin calcium.
12. A process for purifying rosuvastatin calcium comprising converting the isopropylammonium salt of claim 2 to rosuvastatin calcium.
13. The process of either of claims 11 or 12, wherein the calcium salt is purified by combining the isopropylammonium salt with an aqueous base to obtain a solution of a sodium or potassium salt, evaporating the solution to obtain a residue, combining the residue with water and a source of calcium to precipitate the calcium salt.
14. A process for purifying rosuvastatin calcium comprising a) combining rosuvastatin calcium with water to obtain a mixture;
b) combining the mixture with an acid to obtain a solution of rosuvastatin acid;
c) extracting the solution with a water immiscible solvent to obtain an organic phase;
d) evaporating the organic phase to obtain a residue;
e) combining the residue with an organic solvent and isopropylamine to obtain a crystalline form of rosuvastatin isopropylammonium salt having an X-ray powder diffraction pattern with peaks at 6.2, 18.8, 19.3, 20.6 and 22.3 ~0.2 deg. 2-theta.
f) cooling the organic solvent to precipitate the isopropyl ammonium salt;
and g) converting the isopropyl ammonium salt to the calcium salt.
b) combining the mixture with an acid to obtain a solution of rosuvastatin acid;
c) extracting the solution with a water immiscible solvent to obtain an organic phase;
d) evaporating the organic phase to obtain a residue;
e) combining the residue with an organic solvent and isopropylamine to obtain a crystalline form of rosuvastatin isopropylammonium salt having an X-ray powder diffraction pattern with peaks at 6.2, 18.8, 19.3, 20.6 and 22.3 ~0.2 deg. 2-theta.
f) cooling the organic solvent to precipitate the isopropyl ammonium salt;
and g) converting the isopropyl ammonium salt to the calcium salt.
15. The process of claim 14, wherein the mixture obtained in step a) further includes a water miscible solvent.
16. The process of claim 15, wherein the water miscible solvent is acetonitrile.
17. The process of claim 16, wherein the ratio between the water and acetonitrile is about 1:2 to about 2:1 by volume.
18. The process of claim 17, wherein the ratio between the water and acetonitrile is about 1:1.
19. The process of claim 14, wherein the weight to volume ratio of the calcium salt is about 1:10 to about 1:40 Kg/L.
20. The process of claim 14, wherein the acid is selected from the group consisting of hydrochlorice, hydrosulforic, and hydrobromie.
21. The process of claim 14, wherein the water immiscible solvent in step c) is ethyl acetate.
22. The process of claim 14, wherein the evaporation is at a pressure below about 760mmHg.
23. Crystalline rosuvastatin cyclohexylammonium salt.
24. A crystalline form of rosuvastatin cyclohexylammonium salt having an X-ray powder diffraction pattern characterized by peaks at 8.7, 9.5, 15.3, 19.6 and 20.8 ~0.2 deg. 2-theta.
25. The crystalline form of claim 24 further having peaks at 10.7, 14.3, 14.7, 17.4, 18.0, 22.1 and 28.1 ~0.2 deg. 2-theta.
26. The crystalline form of claim 25 having an X-ray powder diffraction pattern substantially as depicted in Figure 2.
27. A process for preparing a crystalline form of claim 24 comprising combining a solution of rosuvastatin acid in an organic solvent with cyclohexylamine to precipitate the crystalline form and recovering the crystalline form.
28. The process of claim 27, wherein precipitation is induced by cooling the solution to a temperature of less than about 10°C.
29. The process of claim 27, wherein the combining is carried out at a temperature of about 20°C to about 40°C.
30. The process of claim 28, wherein the temperature is about 30°C.
31. The process of claim 27, wherein the organic solvent is ethyl acetate.
32. A process for preparing a crystalline form of claim 24 comprising combining a solution of rosuvastatin acid in ethyl acetate with cyclohexylamine followed by stirring at a temperature of about 30°C, followed by cooling to a temperature of less than about 10°C to precipitate the crystalline form and recovering the crystalline form.
33. A process for purifying rosuvastatin calcium comprising a) converting rosuvastatin calcium salt to rosuvastatin acid;
b) converting rosuvastatin acid to the cyclohexylammonium salt of claim 24;
c) converting the cyclohexylammonium salt to rosuvastatin calcium.
b) converting rosuvastatin acid to the cyclohexylammonium salt of claim 24;
c) converting the cyclohexylammonium salt to rosuvastatin calcium.
34. A process for purifying rosuvastatin calcium comprising converting the cyclohexylammonium salt of claim 24 to rosuvastatin calcium.
35. The process of either of claims 33 or 34, wherein the calcium salt is prepared by combining the cyclohexylammonium salt with an aqueous base to obtain a solution of a sodium or potassium salt, evaporating the solution to obtain a residue, combining the residue with water and a source of calcium to precipitate the calcium salt.
36. A process for purifying rosuvastatin calcium comprising a) combining rosuvastatin calcium with water to obtain a mixture;
b) combining the mixture with an acid to obtain a solution of rosuvastatin acid;
c) extracting the solution with a water immiscible solvent to obtain an organic phase;
d) evaporating the organic phase to obtain a residue;
e) combining the residue with an organic solvent and the cyclohexylamine to obtain the cyclohexylamine salt of claim 24;
f) cooling the organic solvent to precipitate the cyclohexylammonium salt;
and g) converting the cyclohexylammonium salt to the calcium salt.
b) combining the mixture with an acid to obtain a solution of rosuvastatin acid;
c) extracting the solution with a water immiscible solvent to obtain an organic phase;
d) evaporating the organic phase to obtain a residue;
e) combining the residue with an organic solvent and the cyclohexylamine to obtain the cyclohexylamine salt of claim 24;
f) cooling the organic solvent to precipitate the cyclohexylammonium salt;
and g) converting the cyclohexylammonium salt to the calcium salt.
37. The process of claim 36, wherein the mixture obtained in step a) further includes a water miscible solvent.
38. The process of claim 37, wherein the water miscible solvent is acetonitrile.
39. The process of claim 38, wherein the ratio of water to acetonitrile is about 1:2 to about 2:1 by volume.
40. The process of claim 39, wherein the ratio between the water and acetonitrile is about 1:1.
41. The process of claim 36, wherein the weight to volume ratio of the calcium salt is about 1:10 to about 1:40 Kg/L.
42. The process of claim 36, wherein the acid is selected from the group consisting of hydrochloride, hydrosulforic, and hydrobromide.
43. The process of claim 36, wherein the water miscible solvent in step c) is ethyl acetate.
44. The process of claim 36, wherein the evaporation is at a pressure below about 760mmHg.
45. A process for purifying rosuvastatin calcium comprising a) combining rosuvastatin calcium with water to obtain a mixture;
b) combining the mixture with an acid to obtain a solution of rosuvastatin acid;
c) extracting the solution with a water immiscible solvent to obtain an organic phase;
d) evaporating the organic phase to obtain a residue;
e) combining the residue with an organic solvent and an amine to obtain the ammonium salt;
f) cooling the organic solvent to precipitate the ammonium salt; and g) converting the ammonium salt to the calcium salt.
b) combining the mixture with an acid to obtain a solution of rosuvastatin acid;
c) extracting the solution with a water immiscible solvent to obtain an organic phase;
d) evaporating the organic phase to obtain a residue;
e) combining the residue with an organic solvent and an amine to obtain the ammonium salt;
f) cooling the organic solvent to precipitate the ammonium salt; and g) converting the ammonium salt to the calcium salt.
46. The process of claim 45, wherein the mixture obtained in step a) further includes a water miscible solvent.
47. The process of claim 45, wherein the water miscible solvent in step a) is acetonitrile.
48. The process of claim 47, wherein the ratio of water to acetonitrile is about 1:2 to about 2:1
49. The process of claim 48, wherein the ratio of water to acetonitrile is about 1:1.
50. The process of claim 45, wherein the weight to volume ratio of the calcium salt is about 1:10 to about 1:40 Kg/L.
51. The process of claim 45, wherein the acid is selected from the group consisting of hydrochloric hydrosulforic and hydrobromic
52. The process of claim 45, wherein the water immiscible solvent in step c) is ethyl acetate.
53. The process of claim 45, wherein the evaporation is at a pressure below about 760mmHg.
54. The process of claim 45, wherein the organic solvent in step e) is ethylacetate.
55. The process of claim 45, wherein the amine is isopropyl amine or cyclohexylamine.
56. A process for preparing a pharmaceutical formulation of rosuvastatin calcium comprising converting the rosuvastatin calcium of claim 11, 12, 14, 33, 34, 36 or 45 to a pharmaceutical formulation.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52512803P | 2003-11-24 | 2003-11-24 | |
| US60/525,128 | 2003-11-24 | ||
| US53447904P | 2004-01-05 | 2004-01-05 | |
| US60/534,479 | 2004-01-05 | ||
| PCT/US2004/039469 WO2005051921A1 (en) | 2003-11-24 | 2004-11-24 | Crystalline ammonium salts of rosuvastatin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2546701A1 true CA2546701A1 (en) | 2005-06-09 |
| CA2546701C CA2546701C (en) | 2010-07-27 |
Family
ID=34636534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2546701A Expired - Fee Related CA2546701C (en) | 2003-11-24 | 2004-11-24 | Crystalline ammonium salts of rosuvastatin |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7777034B2 (en) |
| EP (1) | EP1601658A1 (en) |
| CA (1) | CA2546701C (en) |
| IL (1) | IL175123A0 (en) |
| TW (1) | TW200526596A (en) |
| WO (1) | WO2005051921A1 (en) |
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| GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
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| GB0324791D0 (en) | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
| WO2005051921A1 (en) | 2003-11-24 | 2005-06-09 | Teva Pharmaceutical Industries Ltd. | Crystalline ammonium salts of rosuvastatin |
| KR100887264B1 (en) * | 2003-12-02 | 2009-03-06 | 테바 파마슈티컬 인더스트리즈 리미티드 | Reference standard for characterization of rosuvastatin |
| EP1709008A1 (en) * | 2004-01-19 | 2006-10-11 | Ranbaxy Laboratories Limited | Salts of hmg-coa reductase inhibitors and use thereof |
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| US20070167625A1 (en) * | 2005-02-22 | 2007-07-19 | Anna Balanov | Preparation of rosuvastatin |
| PL1851206T3 (en) | 2005-02-22 | 2013-01-31 | Teva Pharma | Rosuvastatin and salts thereof free of rosuvastatin alkylether and a process for the preparation thereof |
| US20070037979A1 (en) * | 2005-02-22 | 2007-02-15 | Valerie Niddam-Hildesheim | Preparation of rosuvastatin |
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| GB0218781D0 (en) | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| CN1742000A (en) | 2002-12-10 | 2006-03-01 | 兰贝克赛实验室有限公司 | Process for the preparation of rosuvastatin |
| WO2005021511A1 (en) | 2003-08-27 | 2005-03-10 | Hetero Drugs Limited | A novel process for amorphous rosuvastatin calcium |
| EP1816126A1 (en) | 2003-08-28 | 2007-08-08 | Teva Pharmaceutical Industries Limited | Process for preparation of rosuvastatin calcium |
| CA2657076A1 (en) | 2003-08-28 | 2005-03-17 | Teva Pharmaceutical Industries Ltd. | Process for the preparation of rosuvastatin calcium |
| EP1678148A1 (en) | 2003-10-22 | 2006-07-12 | Ranbaxy Laboratories Limited | Process for the preparation of amorphous rosuvastatin calcium |
| WO2005051921A1 (en) | 2003-11-24 | 2005-06-09 | Teva Pharmaceutical Industries Ltd. | Crystalline ammonium salts of rosuvastatin |
| KR20060135712A (en) * | 2003-12-24 | 2006-12-29 | 테바 파마슈티컬 인더스트리즈 리미티드 | Process for preparation of statins with high syn to anti ratio |
| US20070179166A1 (en) * | 2003-12-24 | 2007-08-02 | Valerie Niddam-Hildesheim | Process for preparation of statins with high syn to anti ratio |
| EP1709008A1 (en) | 2004-01-19 | 2006-10-11 | Ranbaxy Laboratories Limited | Salts of hmg-coa reductase inhibitors and use thereof |
| WO2006035277A2 (en) | 2004-09-27 | 2006-04-06 | Ranbaxy Laboratories Limited | Novel processes for preparing amorphous rosuvastatin calcium and a novel polymorphic form of rosuvastatin sodium |
| GB0428328D0 (en) | 2004-12-24 | 2005-02-02 | Astrazeneca Uk Ltd | Chemical process |
| EP1844021A1 (en) | 2005-01-31 | 2007-10-17 | Ciba Specialty Chemicals Holding Inc. | Crystalline forms of rosuvastatin calcium salt |
| PL1851206T3 (en) * | 2005-02-22 | 2013-01-31 | Teva Pharma | Rosuvastatin and salts thereof free of rosuvastatin alkylether and a process for the preparation thereof |
| US20070037979A1 (en) * | 2005-02-22 | 2007-02-15 | Valerie Niddam-Hildesheim | Preparation of rosuvastatin |
| EP1863773A1 (en) | 2005-03-22 | 2007-12-12 | Unichem Laboratories Limited | Process for preparation of rosuvastatin |
| WO2006106526A1 (en) | 2005-04-04 | 2006-10-12 | Unichem Laboratories Limited | Process for preparation of calcium salt of rosuvastatin |
| CN1872841A (en) | 2005-06-01 | 2006-12-06 | 信谊药厂 | Method for preparing Rosuvastatin Calcium and key intermediate |
| CN102807530B (en) | 2005-06-24 | 2015-08-05 | 力奇制药公司 | Prepare the method for unformed ZD-4522 free from foreign meter |
| AU2006261088B2 (en) | 2005-06-24 | 2012-11-08 | Lek Pharmaceuticals D.D. | Process for preparing pure amorphous rosuvastatin calcium |
| GB0514078D0 (en) | 2005-07-08 | 2005-08-17 | Astrazeneca Uk Ltd | Chemical process |
| WO2007099561A1 (en) | 2006-02-27 | 2007-09-07 | Cadila Healthcare Limited | Process for preparing rosuvastatin calcium |
-
2004
- 2004-11-24 WO PCT/US2004/039469 patent/WO2005051921A1/en active Application Filing
- 2004-11-24 US US10/996,483 patent/US7777034B2/en not_active Expired - Fee Related
- 2004-11-24 EP EP04812066A patent/EP1601658A1/en not_active Withdrawn
- 2004-11-24 TW TW093136170A patent/TW200526596A/en unknown
- 2004-11-24 CA CA2546701A patent/CA2546701C/en not_active Expired - Fee Related
-
2005
- 2005-01-19 US US10/586,555 patent/US20090036680A1/en not_active Abandoned
-
2006
- 2006-04-24 IL IL175123A patent/IL175123A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1601658A1 (en) | 2005-12-07 |
| US7777034B2 (en) | 2010-08-17 |
| IL175123A0 (en) | 2006-09-05 |
| US20090036680A1 (en) | 2009-02-05 |
| WO2005051921A1 (en) | 2005-06-09 |
| TW200526596A (en) | 2005-08-16 |
| CA2546701C (en) | 2010-07-27 |
| US20050131066A1 (en) | 2005-06-16 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20151124 |