AU2006261088B2 - Process for preparing pure amorphous rosuvastatin calcium - Google Patents
Process for preparing pure amorphous rosuvastatin calcium Download PDFInfo
- Publication number
- AU2006261088B2 AU2006261088B2 AU2006261088A AU2006261088A AU2006261088B2 AU 2006261088 B2 AU2006261088 B2 AU 2006261088B2 AU 2006261088 A AU2006261088 A AU 2006261088A AU 2006261088 A AU2006261088 A AU 2006261088A AU 2006261088 B2 AU2006261088 B2 AU 2006261088B2
- Authority
- AU
- Australia
- Prior art keywords
- rosuvastatin
- calcium
- process according
- sodium
- water
- 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.)
- Ceased
Links
- 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 description 105
- 229960004796 rosuvastatin calcium Drugs 0.000 title claims abstract description 91
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 84
- 238000000034 method Methods 0.000 claims abstract description 77
- 229960000672 rosuvastatin Drugs 0.000 claims abstract description 71
- 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 abstract description 65
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 60
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000002253 acid Substances 0.000 claims abstract description 34
- 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 abstract description 34
- 239000011575 calcium Substances 0.000 claims abstract description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 27
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 22
- -1 methyl rosuvastatin Chemical compound 0.000 claims abstract description 22
- IJHZGLLGELSZAF-OKLSWEBGSA-N tert-butyl (e,3r,5s)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-propan-2-ylpyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate 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)OC(C)(C)C IJHZGLLGELSZAF-OKLSWEBGSA-N 0.000 claims abstract description 15
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 11
- 238000011282 treatment Methods 0.000 claims abstract description 10
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 9
- 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 9
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 8
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 8
- 239000000920 calcium hydroxide Substances 0.000 claims abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 44
- 239000000243 solution Substances 0.000 claims description 40
- 239000002904 solvent Substances 0.000 claims description 30
- 239000007787 solid Substances 0.000 claims description 26
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 22
- 238000003756 stirring Methods 0.000 claims description 19
- 239000007864 aqueous solution Substances 0.000 claims description 16
- 159000000007 calcium salts Chemical class 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 15
- 239000006185 dispersion Substances 0.000 claims description 14
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 10
- 239000001110 calcium chloride Substances 0.000 claims description 10
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 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 description 8
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims description 7
- 229960005147 calcium acetate Drugs 0.000 claims description 7
- 239000001639 calcium acetate Substances 0.000 claims description 7
- 235000011092 calcium acetate Nutrition 0.000 claims description 7
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 6
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 6
- GFQBEGBGISQEDF-UHFFFAOYSA-L calcium;2,2-dimethylpropanoate Chemical compound [Ca+2].CC(C)(C)C([O-])=O.CC(C)(C)C([O-])=O GFQBEGBGISQEDF-UHFFFAOYSA-L 0.000 claims description 6
- HRBZRZSCMANEHQ-UHFFFAOYSA-L calcium;hexadecanoate Chemical compound [Ca+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O HRBZRZSCMANEHQ-UHFFFAOYSA-L 0.000 claims description 6
- 229960004132 diethyl ether Drugs 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- XQKKWWCELHKGKB-UHFFFAOYSA-L calcium acetate monohydrate Chemical compound O.[Ca+2].CC([O-])=O.CC([O-])=O XQKKWWCELHKGKB-UHFFFAOYSA-L 0.000 claims description 5
- 229940067460 calcium acetate monohydrate Drugs 0.000 claims description 5
- LTPCXXMGKDQPAO-UHFFFAOYSA-L calcium;2-ethylhexanoate Chemical compound [Ca+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O LTPCXXMGKDQPAO-UHFFFAOYSA-L 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 239000008280 blood Substances 0.000 claims description 4
- 210000004369 blood Anatomy 0.000 claims description 4
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 32
- 239000012535 impurity Substances 0.000 abstract description 13
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract description 10
- 239000000010 aprotic solvent Substances 0.000 abstract description 7
- 235000011116 calcium hydroxide Nutrition 0.000 abstract description 5
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001768 cations Chemical class 0.000 abstract description 2
- 239000012453 solvate Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 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 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 229940052303 ethers for general anesthesia Drugs 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001242 acetic acid derivatives Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 4
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 4
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 102100029077 3-hydroxy-3-methylglutaryl-coenzyme A reductase Human genes 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910001424 calcium ion Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- MTPOIJDLKCVHGS-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N.CC(C)(C)CC(C)(C)N MTPOIJDLKCVHGS-UHFFFAOYSA-N 0.000 description 1
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
- 101710158485 3-hydroxy-3-methylglutaryl-coenzyme A reductase Proteins 0.000 description 1
- 229910016523 CuKa Inorganic materials 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SIP200500187 | 2005-06-24 | ||
| SI200500187 | 2005-06-24 | ||
| PCT/EP2006/006008 WO2006136408A2 (en) | 2005-06-24 | 2006-06-22 | Process for preparing pure amorphous rosuvastatin calcium |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2006261088A1 AU2006261088A1 (en) | 2006-12-28 |
| AU2006261088B2 true AU2006261088B2 (en) | 2012-11-08 |
Family
ID=37440674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006261088A Ceased AU2006261088B2 (en) | 2005-06-24 | 2006-06-22 | Process for preparing pure amorphous rosuvastatin calcium |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8207333B2 (enExample) |
| EP (1) | EP1915349B2 (enExample) |
| JP (1) | JP5416403B2 (enExample) |
| CN (1) | CN101203496B (enExample) |
| AU (1) | AU2006261088B2 (enExample) |
| CA (1) | CA2611920C (enExample) |
| ES (1) | ES2564807T5 (enExample) |
| HU (1) | HUE027012T2 (enExample) |
| IL (1) | IL187578A0 (enExample) |
| PL (1) | PL1915349T5 (enExample) |
| SI (1) | SI1915349T1 (enExample) |
| WO (1) | WO2006136408A2 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2870593B2 (ja) | 1997-02-03 | 1999-03-17 | 日本電気株式会社 | 焦点誤差検出器 |
| WO2005023778A2 (en) | 2003-08-28 | 2005-03-17 | Teva Pharmaceutical Industries Ltd. | Process for preparation of rosuvastatin calcium |
| US7777034B2 (en) | 2003-11-24 | 2010-08-17 | Teva Pharmaceutical Industries Ltd. | Crystalline ammonium salts of rosuvastatin |
| EP1689723B1 (en) | 2003-12-02 | 2011-04-27 | Teva Pharmaceutical Industries, Ltd. | Reference standard for characterization of rosuvastatin |
| CA2591439C (en) | 2005-02-22 | 2013-03-26 | Teva Pharmaceutical Industries Ltd. | Rosuvastatin and salts thereof free of rosuvastatin alkylether and a process for the preparation thereof |
| CN102807530B (zh) * | 2005-06-24 | 2015-08-05 | 力奇制药公司 | 制备不含杂质的无定型罗苏伐他汀钙的方法 |
| MX2007004427A (es) | 2005-08-16 | 2007-06-14 | Teva Pharma | Intermedio de rosuvastatina cristalina. |
| US7994178B2 (en) | 2006-09-18 | 2011-08-09 | Teva Pharmaceutical Industries, Ltd. | Crystalline rosuvastatin calcium and compositions thereof for treatment of hyperlipidaemia |
| WO2008053334A2 (en) * | 2006-10-31 | 2008-05-08 | Aurobindo Pharma Limited | An improved process for preparing rosuvastatin calcium |
| EP2125754B1 (en) * | 2007-02-08 | 2012-04-11 | Aurobindo Pharma Limited | Process for preparation of rosuvastatin calcium |
| US20090069563A1 (en) | 2007-07-12 | 2009-03-12 | Valerie Niddam-Hildesheim | Rosuvastatin intermediates and their preparation |
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- 2006-06-22 JP JP2008517414A patent/JP5416403B2/ja not_active Expired - Fee Related
- 2006-06-22 CN CN2006800226730A patent/CN101203496B/zh not_active Expired - Fee Related
- 2006-06-22 ES ES06754502T patent/ES2564807T5/es active Active
- 2006-06-22 US US11/916,599 patent/US8207333B2/en not_active Expired - Fee Related
- 2006-06-22 PL PL06754502T patent/PL1915349T5/pl unknown
- 2006-06-22 EP EP06754502.0A patent/EP1915349B2/en not_active Not-in-force
- 2006-06-22 AU AU2006261088A patent/AU2006261088B2/en not_active Ceased
- 2006-06-22 SI SI200632034A patent/SI1915349T1/sl unknown
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2007
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1915349A2 (en) | 2008-04-30 |
| ES2564807T3 (es) | 2016-03-29 |
| WO2006136408A3 (en) | 2007-04-19 |
| PL1915349T5 (pl) | 2019-02-28 |
| CN101203496A (zh) | 2008-06-18 |
| ES2564807T5 (es) | 2019-02-26 |
| US8207333B2 (en) | 2012-06-26 |
| CA2611920A1 (en) | 2006-12-28 |
| EP1915349B1 (en) | 2015-12-09 |
| CN101203496B (zh) | 2011-04-20 |
| SI1915349T1 (sl) | 2016-05-31 |
| JP2008543899A (ja) | 2008-12-04 |
| PL1915349T3 (pl) | 2016-05-31 |
| WO2006136408A2 (en) | 2006-12-28 |
| US20080188504A1 (en) | 2008-08-07 |
| CA2611920C (en) | 2015-05-05 |
| JP5416403B2 (ja) | 2014-02-12 |
| AU2006261088A1 (en) | 2006-12-28 |
| IL187578A0 (en) | 2008-03-20 |
| EP1915349B2 (en) | 2018-09-12 |
| HUE027012T2 (en) | 2016-10-28 |
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