CA2537271A1 - Process for preparation of rosuvastatin calcium - Google Patents
Process for preparation of rosuvastatin calcium Download PDFInfo
- Publication number
- CA2537271A1 CA2537271A1 CA002537271A CA2537271A CA2537271A1 CA 2537271 A1 CA2537271 A1 CA 2537271A1 CA 002537271 A CA002537271 A CA 002537271A CA 2537271 A CA2537271 A CA 2537271A CA 2537271 A1 CA2537271 A1 CA 2537271A1
- Authority
- CA
- Canada
- Prior art keywords
- rosuvastatin
- calcium
- water
- rosuvastatin calcium
- ester
- 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
- 238000000034 method Methods 0.000 title claims abstract 35
- 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 title claims abstract 25
- 229960004796 rosuvastatin calcium Drugs 0.000 title claims 15
- 239000012535 impurity Substances 0.000 claims abstract 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 16
- 239000000243 solution Substances 0.000 claims 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 9
- 238000004128 high performance liquid chromatography Methods 0.000 claims 9
- 150000002148 esters Chemical class 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 7
- 229960000672 rosuvastatin Drugs 0.000 claims 7
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound 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 claims 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 6
- 239000007864 aqueous solution Substances 0.000 claims 6
- 239000011575 calcium Substances 0.000 claims 6
- 229910052791 calcium Inorganic materials 0.000 claims 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 6
- 238000001704 evaporation Methods 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 6
- 238000003756 stirring Methods 0.000 claims 5
- 159000000007 calcium salts Chemical class 0.000 claims 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 4
- 230000008020 evaporation Effects 0.000 claims 4
- 239000012071 phase Substances 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical group [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 239000008346 aqueous phase Substances 0.000 claims 3
- 239000001110 calcium chloride Substances 0.000 claims 3
- 229910001628 calcium chloride Inorganic materials 0.000 claims 3
- 229940093499 ethyl acetate Drugs 0.000 claims 3
- 235000019439 ethyl acetate Nutrition 0.000 claims 3
- 238000001914 filtration Methods 0.000 claims 3
- 239000003444 phase transfer catalyst Substances 0.000 claims 3
- 238000005406 washing Methods 0.000 claims 3
- -1 C12 hydrocarbon Chemical class 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 2
- 239000008280 blood Substances 0.000 claims 2
- 210000004369 blood Anatomy 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000000725 suspension Substances 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims 1
- 229910001863 barium hydroxide Inorganic materials 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 125000004492 methyl ester group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- RGEBGDYYHAFODH-DHMAKVBVSA-M sodium;(e,3r,5s)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-propan-2-ylpyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate Chemical compound [Na+].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 RGEBGDYYHAFODH-DHMAKVBVSA-M 0.000 claims 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims 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
The present invention provides processes for preparing rosuvastatin calcium salt substantially free of impurities on an industrial scale (I).
Claims (39)
1. A process for producing rosuvastatin calcium comprising:
a) reacting a C1 to C4 alkyl ester of rosuvastatin with a base in presence of a C1 to C4 alcohol to obtain a solution;
b) concentrating the solution to obtain a residue;
c) combining the residue with water to obtain an aqueous solution;
d) washing the aqueous solution with a water immiscible organic solvent;
e) removing traces of the organic solvent;
f) adding a source of calcium to the solution to precipitate rosuvastatin calcium; and g) recovering the rosuvastatin calcium salt.
a) reacting a C1 to C4 alkyl ester of rosuvastatin with a base in presence of a C1 to C4 alcohol to obtain a solution;
b) concentrating the solution to obtain a residue;
c) combining the residue with water to obtain an aqueous solution;
d) washing the aqueous solution with a water immiscible organic solvent;
e) removing traces of the organic solvent;
f) adding a source of calcium to the solution to precipitate rosuvastatin calcium; and g) recovering the rosuvastatin calcium salt.
2. The process of claim 1, wherein the ester is a methyl ester.
3. The process of claim 1 or 2, wherein the ester is a t-butyl ester.
4. The process of claim 1, 2, or 3, further comprising the step of stirring before step (b).
5. The process of any one of claim 1, 2, 3, or 4, wherein concentrating in step (b) is carried out by evaporation.
6. The process of claims 5, wherein evaporation is carried out under reduced pressure.
7. The process of claim 1, 2, 3, 4, 5, or 6, wherein reacting is carried out by adding the base to a suspension of the ester in the alcohol.
8. The process of claim 1, 2, 3, 4, 5, 6, or 7, wherein the alcohol is ethanol.
9. The process of claim 1, 2, 3, 4, 5, 6, 7, or 8 wherein the organic solvent is a C4 to C7 ester or ketone.
10. The process of claim 1, 2, 3, 4, 5, 6, 7, 8, or 9, wherein the ester is ethylacetate.
11. The process of claim 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, wherein removing in step (e) is carried out by evaporation.
12. The process of claim 11, wherein the evaporation is carried out under reduced pressure.
13. The process of claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, wherein the source of calcium is calcium chloride.
14. The process of claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, wherein the recovering step is carried out with filtration.
15. The process of claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14, wherein the base is selected from the group consisting of sodium, potassium and barium hydroxide.
16. A process for producing rosuvastatin calcium salt comprising:
a) combining a suspension of t-butyl ester of rosuvastatin in ethanol with sodium hydroxide to obtain a solution, and stirring during or after the combining;
b) evaporating the solution under reduced pressure to obtain a residue;
c) combining the residue with water to obtain an aqueous solution;
d) washing the aqueous solution with ethyl acetate;
e) evaporating traces of the ethyl acetate under reduced pressure;
f) adding calcium chloride to the solution to precipitate rosuvastatin calcium;
and g) filtering the rosuvastatin calcium salt.
a) combining a suspension of t-butyl ester of rosuvastatin in ethanol with sodium hydroxide to obtain a solution, and stirring during or after the combining;
b) evaporating the solution under reduced pressure to obtain a residue;
c) combining the residue with water to obtain an aqueous solution;
d) washing the aqueous solution with ethyl acetate;
e) evaporating traces of the ethyl acetate under reduced pressure;
f) adding calcium chloride to the solution to precipitate rosuvastatin calcium;
and g) filtering the rosuvastatin calcium salt.
17. A process for producing rosuvastatin calcium salt comprising:
a) reacting a C1 to C4 alkyl ester of rosuvastatin in a water immiscible phase, with a base in an aqueous phase, in presence of a phase transfer catalyst to obtain rosuvastatin in the aqueous phase;
b) adding a source of calcium to the aqueous phase to precipitate rosuvastatin calcium; and c) recovering the rosuvastatin calcium salt.
a) reacting a C1 to C4 alkyl ester of rosuvastatin in a water immiscible phase, with a base in an aqueous phase, in presence of a phase transfer catalyst to obtain rosuvastatin in the aqueous phase;
b) adding a source of calcium to the aqueous phase to precipitate rosuvastatin calcium; and c) recovering the rosuvastatin calcium salt.
18. The process of claim 17, further comprising a step of removing traces of the water immiscible solvent before adding a source of calcium.
19. The process of claim 17 or 18, wherein the ester is a t-butyl ester.
20. The process of claim 17, 18, or 19, further comprising stirring during the reaction.
21. The process of claim 17, 18, 19, or 20, wherein the water immiscible phase is a solvent selected from the group consisting of substituted and unsubstituted C5 to C12 hydrocarbon, C4 to C7 ester, C4 to C7 ketone and mixtures thereof.
22. The process of claim 20, wherein the hydrocarbon is toluene or chlorobenzene.
23. The process of claim 17, 18, 19, 20, 21, or 22, wherein the phase transfer catalyst is an alkyl, aryl, alkaryl or arylalkyl ammonium salt.
24. A process for producing rosuvastatin calcium salt comprising:
a) reacting, t-butyl ester of rosuvastatin with sodium hydroxide in presence of water, a tetrabutylammonium phase transfer catalyst and an organic solvent selected from the group consisting of toluene and chlorobenzene to obtain rosuvastatin in the water;
b) removing traces of the toluene or chlorobenzene from the water;
c) adding calcium chloride to the water to precipitate rosuvastatin calcium;
and d) filtering the rosuvastatin calcium salt.
a) reacting, t-butyl ester of rosuvastatin with sodium hydroxide in presence of water, a tetrabutylammonium phase transfer catalyst and an organic solvent selected from the group consisting of toluene and chlorobenzene to obtain rosuvastatin in the water;
b) removing traces of the toluene or chlorobenzene from the water;
c) adding calcium chloride to the water to precipitate rosuvastatin calcium;
and d) filtering the rosuvastatin calcium salt.
25. The process of claim 24, further comprising stirring during the reaction.
26. A process for producing rosuvastatin calcium salt substantially free of impurities comprising the steps of:
a) reacting a C1 to C4 ester of rosuvastatin with a base in a two phase system of water and acetonitrile;
b) concentrating the water phase to obtain a residue;
c) adding a source of calcium and water to the residue to form a solution in water; and d) recovering rosuvastatin calcium as a precipitate.
a) reacting a C1 to C4 ester of rosuvastatin with a base in a two phase system of water and acetonitrile;
b) concentrating the water phase to obtain a residue;
c) adding a source of calcium and water to the residue to form a solution in water; and d) recovering rosuvastatin calcium as a precipitate.
27. The process of claim 26, further comprising stirring during the reaction.
28. The process of claim 1, 16, 17, 24, or 26, wherein the calcium salt contains less than or of about 0.4% total impurities as measured by area percentage HPLC.
29. The process of claim 28, wherein the impurities is of or less than about 0.3% as measured by area percentage HPLC.
30. The process of claim 1, 16, 17, 24, or 26, wherein the calcium salt does not have detectable level of impurities when measured by HPLC at RRT 0.62, 1.18, 1.26, 1.60, 2.68, 3.66, 3.89, 3.93 and 4.10.
31. The process of claim 30, wherein the impurities are less than about 0.01%
as measured by HPLC area percentage.
as measured by HPLC area percentage.
32. A process for producing rosuvastatin calcium comprising:
a) preparing a solution of rosuvastatin sodium;
b) concentrating the solution to obtain a residue;
c) combining the residue with water to obtain an aqueous solution;
d) washing the aqueous solution with a water immiscible organic solvent;
e) removing traces of the organic solvent;
f) adding a source of calcium to the solution to precipitate rosuvastatin calcium;
and g) recovering the rosuvastatin calcium salt.
a) preparing a solution of rosuvastatin sodium;
b) concentrating the solution to obtain a residue;
c) combining the residue with water to obtain an aqueous solution;
d) washing the aqueous solution with a water immiscible organic solvent;
e) removing traces of the organic solvent;
f) adding a source of calcium to the solution to precipitate rosuvastatin calcium;
and g) recovering the rosuvastatin calcium salt.
33. Rosuvastatin calcium in solid state having less than or of about 0.4%
total impurities as measured by area percentage HPLC.
total impurities as measured by area percentage HPLC.
34. The rosuvastatin calcium of claim 33, wherein the impurities is of or less than about 0.3% as measured by area percentage HPLC.
35. Rosuvastatin calcium in solid state, wherein the calcium salt does not have detectable level of impurities when measured by HPLC at RRT 1.26.
36. The rosuvastatin calcium of claim 35, wherein the calcium salt does not have further detectable level of impurities when measured by HPLC at RRT 0.62, 1.18, 1.60, 2.68, 3.66, 3.89, 3.93 and 4.10.
37. The rosuvastatin calcium of claim 36, wherein the impurities are less than about 0.01% as measured by HPLC area percentage.
38. A pharmaceutical formulation for administration to a mammal in need of a reduction in blood cholesterol level comprising rosuvastatin calcium of claim 33, 34, 35, 36 or 37 as active ingredient, and at least a pharmaceutically acceptable excipient.
39. A method of treating a mammal in need of a reduction in blood cholesterol level comprising the step of administering the pharmaceutical formulation of claim to the mammal in need thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002657076A CA2657076A1 (en) | 2003-08-28 | 2004-08-24 | Process for the preparation of rosuvastatin calcium |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49876403P | 2003-08-28 | 2003-08-28 | |
| US60/498,764 | 2003-08-28 | ||
| US53467804P | 2004-01-06 | 2004-01-06 | |
| US60/534,678 | 2004-01-06 | ||
| PCT/US2004/027530 WO2005023778A2 (en) | 2003-08-28 | 2004-08-24 | Process for preparation of rosuvastatin calcium |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002657076A Division CA2657076A1 (en) | 2003-08-28 | 2004-08-24 | Process for the preparation of rosuvastatin calcium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2537271A1 true CA2537271A1 (en) | 2005-03-17 |
Family
ID=34278611
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002657076A Abandoned CA2657076A1 (en) | 2003-08-28 | 2004-08-24 | Process for the preparation of rosuvastatin calcium |
| CA002537271A Abandoned CA2537271A1 (en) | 2003-08-28 | 2004-08-24 | Process for preparation of rosuvastatin calcium |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002657076A Abandoned CA2657076A1 (en) | 2003-08-28 | 2004-08-24 | Process for the preparation of rosuvastatin calcium |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7396927B2 (en) |
| EP (1) | EP1562912A2 (en) |
| CA (2) | CA2657076A1 (en) |
| IL (1) | IL173858A0 (en) |
| TW (2) | TW200920374A (en) |
| WO (1) | WO2005023778A2 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0218781D0 (en) | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
| US7396927B2 (en) | 2003-08-28 | 2008-07-08 | Teva Pharmaceutical Industries Ltd. | Process for preparation of rosuvastatin calcium |
| GB0324791D0 (en) | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
| CA2546701C (en) * | 2003-11-24 | 2010-07-27 | Teva Pharmaceutical Industries Ltd. | Crystalline ammonium salts of rosuvastatin |
| US20070179166A1 (en) * | 2003-12-24 | 2007-08-02 | Valerie Niddam-Hildesheim | Process for preparation of statins with high syn to anti ratio |
| US7851624B2 (en) * | 2003-12-24 | 2010-12-14 | Teva Pharamaceutical Industries Ltd. | Triol form of rosuvastatin and synthesis of rosuvastatin |
| WO2006017698A2 (en) | 2004-08-06 | 2006-02-16 | Transform Pharmaceuticals, Inc. | Novel statin pharmaceutical compositions and related methods of treatment |
| 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 |
| WO2006136408A2 (en) * | 2005-06-24 | 2006-12-28 | Lek Pharmaceuticals D.D. | Process for preparing pure amorphous rosuvastatin calcium |
| EP2508514B1 (en) | 2005-06-24 | 2017-10-18 | LEK Pharmaceuticals d.d. | Process for preparing amorphous rosuvastatin calcium free of impurities |
| CZ299215B6 (en) * | 2005-06-29 | 2008-05-21 | Zentiva, A. S. | Process for preparing hemi-calcium salt of rosuvastatin, i.e. (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxy-6-heptenoic acid |
| US20070099994A1 (en) * | 2005-08-16 | 2007-05-03 | Valerie Niddam-Hildesheim | Rosuvastatin calcium with a low salt content |
| EP1805148A2 (en) | 2005-08-16 | 2007-07-11 | Teva Pharmaceutical Industries Ltd. | Crystalline rosuvastatin intermediate |
| KR101019450B1 (en) | 2005-10-03 | 2011-03-07 | 테바 파마슈티컬 인더스트리즈 리미티드 | Diastereomeric purification of rosuvastatin |
| US7351853B2 (en) * | 2006-01-23 | 2008-04-01 | Albion Advanced Nutrition | Method of manufacturing a granular mineral composition |
| WO2007099561A1 (en) * | 2006-02-27 | 2007-09-07 | Cadila Healthcare Limited | Process for preparing rosuvastatin calcium |
| EP2024341B1 (en) * | 2006-05-03 | 2015-12-02 | MSN Laboratories Private Limited | Novel process for statins and its pharmaceutically acceptable salts thereof |
| KR20080060284A (en) * | 2006-09-18 | 2008-07-01 | 테바 파마슈티컬 인더스트리즈 리미티드 | Crystalline rosuvastatin calcium |
| HUE028475T2 (en) * | 2006-10-09 | 2016-12-28 | Msn Laboratories Private Ltd | Novel process for the preparation of statins and their pharmaceutically acceptable salts thereof |
| WO2008053334A2 (en) * | 2006-10-31 | 2008-05-08 | Aurobindo Pharma Limited | An improved process for preparing rosuvastatin calcium |
| US8212035B2 (en) * | 2007-02-08 | 2012-07-03 | Aurobindo Pharma Ltd. | Process for preparation of rosuvastatin calcium field of the invention |
| US7884226B2 (en) * | 2007-07-12 | 2011-02-08 | Teva Pharmaceutical Industries, Ltd. | Purification of rosuvatatin intermediate by thin film evaporation and chemical method |
| CA2725052C (en) | 2008-05-27 | 2014-09-16 | Changzhou Pharmaceutical Factory Co., Ltd. | Preparation method of rosuvastatin calcium and its intermediates |
| US8507513B2 (en) * | 2009-01-15 | 2013-08-13 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | Process for the preparation of rosuvastatin salts |
| WO2010089770A2 (en) | 2009-01-19 | 2010-08-12 | Msn Laboratories Limited | Improved process for the preparation of highly pure (3r,5s)-7-[2-cyclopropyl-4-(4-fluorophenyl) quinolin-3-yl]-3,5-dihydroxy-6(e)-heptenoic acid and pharmaceutically acceptable salts thereof |
| WO2011086584A2 (en) | 2010-01-18 | 2011-07-21 | Msn Laboratories Limited | Improved process for the preparation of amide intermediates and their use thereof |
| HU230987B1 (en) | 2010-11-29 | 2019-08-28 | Egis Gyógyszergyár Nyrt. | Process for the preparation of pharmaceutical intermediates with high purity |
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| US5354879A (en) | 1991-06-19 | 1994-10-11 | Shionogi Seiyaku Kabushiki Kaisha | Optically active intermediate and method for production thereof |
| JP2648897B2 (en) | 1991-07-01 | 1997-09-03 | 塩野義製薬株式会社 | Pyrimidine derivatives |
| US6063633A (en) * | 1996-02-28 | 2000-05-16 | The University Of Houston | Catalyst testing process and apparatus |
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| GB9812413D0 (en) | 1998-06-10 | 1998-08-05 | Glaxo Group Ltd | Compound and its use |
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| GB9903472D0 (en) | 1999-02-17 | 1999-04-07 | Zeneca Ltd | Chemical process |
| GB0001621D0 (en) | 2000-01-26 | 2000-03-15 | Astrazeneca Ab | Pharmaceutical compositions |
| GB0003305D0 (en) | 2000-02-15 | 2000-04-05 | Zeneca Ltd | Pyrimidine derivatives |
| US6777552B2 (en) * | 2001-08-16 | 2004-08-17 | Teva Pharmaceutical Industries, Ltd. | Processes for preparing calcium salt forms of statins |
| GB0028429D0 (en) | 2000-11-22 | 2001-01-10 | Astrazeneca Ab | Therapy |
| HUP0500616A3 (en) * | 2001-08-16 | 2011-07-28 | Teva Pharma | Processes for preparing calcium salt forms of statins |
| SE0103509D0 (en) | 2001-10-19 | 2001-10-19 | Astrazeneca Ab | Rosuvastatin in pre-demented states |
| KR100511533B1 (en) | 2002-04-09 | 2005-08-31 | 임광민 | CHIRAL INTERMEDIATE, PROCESS FOR THE PRODUCTION THEREOF, AND PROCESS FOR THE PRODUCTION OF HMG-CoA REDUCTASE INHIBITOR |
| AR039836A1 (en) | 2002-05-21 | 2005-03-02 | Ranbaxy Lab Ltd | PROCESS FOR THE PREPARATION OF A PIRIMIDINE ALDEHIDO USEFUL FOR THE PREPARATION OF ROSUVASTATIN |
| GB0218781D0 (en) * | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| HUP0500851A3 (en) | 2002-12-10 | 2008-02-28 | Ranbaxy Lab Ltd | Process for the preparation of rosuvastatin |
| WO2005021511A1 (en) | 2003-08-27 | 2005-03-10 | Hetero Drugs Limited | A novel process for amorphous rosuvastatin calcium |
| US7396927B2 (en) | 2003-08-28 | 2008-07-08 | Teva Pharmaceutical Industries Ltd. | Process for preparation of rosuvastatin calcium |
| CA2546701C (en) | 2003-11-24 | 2010-07-27 | Teva Pharmaceutical Industries Ltd. | Crystalline ammonium salts of rosuvastatin |
| US20080234302A1 (en) | 2004-09-27 | 2008-09-25 | Mohammad Rafeeq | Novel Processes for Preparing Amorphous Rosuvastatin Calcium and a Novel Polymorphic Form of Rosuvastatin Sodium |
| WO2006079611A1 (en) | 2005-01-31 | 2006-08-03 | Ciba Specialty Chemicals Holding Inc. | Crystalline forms of rosuvastatin calcium salt |
| EP1863773A1 (en) | 2005-03-22 | 2007-12-12 | Unichem Laboratories Limited | Process for preparation of rosuvastatin |
| EP1869005A1 (en) | 2005-04-04 | 2007-12-26 | Unichem Laboratories Limited | Process for preparation of calcium salt of rosuvastatin |
| EP2508514B1 (en) | 2005-06-24 | 2017-10-18 | LEK Pharmaceuticals d.d. | Process for preparing amorphous rosuvastatin calcium free of impurities |
| WO2006136408A2 (en) | 2005-06-24 | 2006-12-28 | Lek Pharmaceuticals D.D. | Process for preparing pure amorphous rosuvastatin calcium |
| GB0514078D0 (en) | 2005-07-08 | 2005-08-17 | Astrazeneca Uk Ltd | Chemical process |
-
2004
- 2004-08-24 US US10/925,430 patent/US7396927B2/en not_active Expired - Fee Related
- 2004-08-24 CA CA002657076A patent/CA2657076A1/en not_active Abandoned
- 2004-08-24 WO PCT/US2004/027530 patent/WO2005023778A2/en active Application Filing
- 2004-08-24 CA CA002537271A patent/CA2537271A1/en not_active Abandoned
- 2004-08-24 EP EP04782093A patent/EP1562912A2/en not_active Withdrawn
- 2004-08-27 TW TW097151496A patent/TW200920374A/en unknown
- 2004-08-27 TW TW093125904A patent/TW200518756A/en unknown
-
2006
- 2006-02-21 IL IL173858A patent/IL173858A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20050080134A1 (en) | 2005-04-14 |
| TW200920374A (en) | 2009-05-16 |
| IL173858A0 (en) | 2006-07-05 |
| TW200518756A (en) | 2005-06-16 |
| WO2005023778A3 (en) | 2005-06-16 |
| EP1562912A2 (en) | 2005-08-17 |
| US7396927B2 (en) | 2008-07-08 |
| WO2005023778A2 (en) | 2005-03-17 |
| CA2657076A1 (en) | 2005-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20130318 |