CA2450820A1 - Procedes permettant de preparer des formes salines calciques de statines - Google Patents
Procedes permettant de preparer des formes salines calciques de statines Download PDFInfo
- Publication number
- CA2450820A1 CA2450820A1 CA002450820A CA2450820A CA2450820A1 CA 2450820 A1 CA2450820 A1 CA 2450820A1 CA 002450820 A CA002450820 A CA 002450820A CA 2450820 A CA2450820 A CA 2450820A CA 2450820 A1 CA2450820 A1 CA 2450820A1
- Authority
- CA
- Canada
- Prior art keywords
- statin
- protecting group
- pitavastatin
- rosuvastatin
- calcium salt
- 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
- 238000000034 method Methods 0.000 title claims abstract 40
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 title claims abstract 23
- 159000000007 calcium salts Chemical group 0.000 title claims abstract 8
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 claims abstract 15
- 125000006239 protecting group Chemical group 0.000 claims abstract 13
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims abstract 10
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims abstract 10
- 239000000920 calcium hydroxide Substances 0.000 claims abstract 10
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims abstract 9
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims abstract 9
- 229960005370 atorvastatin Drugs 0.000 claims abstract 9
- 229960002797 pitavastatin Drugs 0.000 claims abstract 8
- VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 claims abstract 8
- 229960000672 rosuvastatin Drugs 0.000 claims abstract 8
- 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 8
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims abstract 7
- 229960002855 simvastatin Drugs 0.000 claims abstract 7
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims abstract 7
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000003377 acid catalyst Substances 0.000 claims abstract 3
- 229960004844 lovastatin Drugs 0.000 claims abstract 3
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims abstract 3
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 4
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims 2
- 229960005110 cerivastatin Drugs 0.000 claims 2
- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 229960003765 fluvastatin Drugs 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 150000002596 lactones Chemical group 0.000 claims 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 239000003444 phase transfer catalyst Substances 0.000 claims 2
- RHGYHLPFVJEAOC-FFNUKLMVSA-L pitavastatin calcium Chemical compound [Ca+2].[O-]C(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1.[O-]C(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 RHGYHLPFVJEAOC-FFNUKLMVSA-L 0.000 claims 2
- 229960002965 pravastatin Drugs 0.000 claims 2
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 claims 2
- 230000001376 precipitating effect Effects 0.000 claims 2
- LALFOYNTGMUKGG-BGRFNVSISA-L rosuvastatin calcium Chemical class [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 2
- 238000001914 filtration Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- 230000015572 biosynthetic process Effects 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- 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
- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Quinoline Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Abstract
L'invention concerne des procédés permettant de préparer un sel calcique d'une statine à partir d'un dérivé d'ester ou d'un dérivé d'ester protégé de la statine au moyen d'hydroxyde de calcium. Le dérivé d'ester ou le dérivé d'ester protégé est mis en contact avec l'hydroxyde de calcium pour obtenir le sel calcique. Les statines préférées sont la rosuvastatine, la pitavastatine et l'atorvastatine, la simvastatine et la lovastatine. Dans les procédés qui commencent avec un dérivé d'ester de statine protégé, le groupe protecteur est soit hydrolysé pendant la formation du sel par contact avec l'hydroxyde de calcium, soit mis en contact avec un catalyseur acide, puis avec l'hydroxyde de calcium.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31281201P | 2001-08-16 | 2001-08-16 | |
| US60/312,812 | 2001-08-16 | ||
| US10/037,412 US6528661B2 (en) | 2000-11-16 | 2001-10-24 | Hydrolysis of [R(R*,R*)]-2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino) carbonyl]-1H-pyrrole-1-heptanoic acid esters with calcium hydroxide |
| US10/037,412 | 2001-10-24 | ||
| PCT/US2002/026012 WO2003016317A1 (fr) | 2001-08-16 | 2002-08-16 | Procedes permettant de preparer des formes salines calciques de statines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2450820A1 true CA2450820A1 (fr) | 2003-02-27 |
| CA2450820C CA2450820C (fr) | 2011-03-15 |
Family
ID=26714105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2450820A Expired - Fee Related CA2450820C (fr) | 2001-08-16 | 2002-08-16 | Procedes permettant de preparer des formes salines calciques de statines |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1425287A4 (fr) |
| JP (2) | JP4188826B2 (fr) |
| CN (1) | CN100430405C (fr) |
| AU (1) | AU2002324715B2 (fr) |
| CA (1) | CA2450820C (fr) |
| CZ (1) | CZ2004337A3 (fr) |
| HR (1) | HRPK20040255B3 (fr) |
| HU (1) | HUP0500616A3 (fr) |
| IL (2) | IL160077A0 (fr) |
| IS (1) | IS7148A (fr) |
| MX (1) | MXPA04001451A (fr) |
| NO (1) | NO20041082L (fr) |
| NZ (1) | NZ529913A (fr) |
| PL (1) | PL370407A1 (fr) |
| SK (1) | SK1402004A3 (fr) |
| TR (1) | TR200302281T2 (fr) |
| WO (1) | WO2003016317A1 (fr) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7411075B1 (en) | 2000-11-16 | 2008-08-12 | Teva Pharmaceutical Industries Ltd. | Polymorphic form of atorvastatin calcium |
| NZ526022A (en) * | 2000-11-16 | 2005-04-29 | Teva Pharma | Hydrolysis of [R(R*,R )]-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid esters with calcium hydroxide |
| US7501450B2 (en) | 2000-11-30 | 2009-03-10 | Teva Pharaceutical Industries Ltd. | Crystal forms of atorvastatin hemi-calcium and processes for their preparation as well as novel processes for preparing other forms |
| IL156055A0 (en) | 2000-11-30 | 2003-12-23 | Teva Pharma | Novel crystal forms of atorvastatin hemi calcium and processes for their preparation as well as novel processes for preparing other forms |
| WO2002057229A1 (fr) | 2001-01-19 | 2002-07-25 | Biocon India Limited | FORME V CRISTALLINE DE SEL HEMICALCIQUE D'ACIDE [R-(R*,R*)]-2-(4-FLUOROPHENYL)-ß,$G(D)-DIHYDROXY-5-(1-METHYLETHYL)-3-PHENYL-4-[(PHENYLAMINO)CARBONYL]-1H-PYRROLE-1-HEPTANOIQUE (ATORVASTATINE) |
| US7361772B2 (en) | 2001-08-16 | 2008-04-22 | Biocon Limited | Process for the production of atorvastatin calcium |
| CA2412012C (fr) | 2001-11-20 | 2011-08-02 | Ed. Geistlich Soehne Ag Fuer Chemische Industrie | Matrice extracellulaire resorbable contenant du collagene i et du collagene ii pour la reconstruction de cartilage |
| BR0215644A (pt) | 2002-03-18 | 2004-12-21 | Biocon Ltd | Inibidores de redutase de hmg-coa amorfos do tamanho de partìcula desejado |
| EP1585736A2 (fr) * | 2002-05-21 | 2005-10-19 | Ranbaxy Laboratories, Ltd. | Procede de preparation de rosuvastatine |
| US7179942B2 (en) | 2002-07-05 | 2007-02-20 | Bicon Limited | Halo-substituted active methylene compounds |
| GB0218781D0 (en) * | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| CA2513837A1 (fr) * | 2003-02-12 | 2004-08-26 | Paul Adriaan Van Der Schaaf | Formes cristallines de calcium de pitavastatine |
| SI1631533T1 (sl) | 2003-04-22 | 2009-08-31 | Bicon Ltd | Nov postopek za stereoselektivno redukcijo beta - ketoestrov |
| GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
| BRPI0412786A (pt) * | 2003-07-25 | 2006-09-26 | Avecia Pharmaceuticals Ltd | processo para a preparação de um composto, e, composto |
| AU2003269477A1 (en) * | 2003-08-26 | 2005-03-10 | Biocon Limited | Novel process for preparation of 7-(3-(4-fluorophenyl)-1-(1-methylethyl)-1h-indol-2-yl)-3, 5-dihydroxy-6-heptenoic acid sodium salt |
| EP1816126A1 (fr) * | 2003-08-28 | 2007-08-08 | Teva Pharmaceutical Industries Limited | Procédé pour la préparation de rosuvastatine calcique |
| WO2005023778A2 (fr) * | 2003-08-28 | 2005-03-17 | Teva Pharmaceutical Industries Ltd. | Procede de preparation de sels calciques de rosuvastatine |
| UY28501A1 (es) | 2003-09-10 | 2005-04-29 | Astrazeneca Uk Ltd | Compuestos químicos |
| WO2005026107A1 (fr) | 2003-09-18 | 2005-03-24 | Biocon Limited | Nouveau processus de preparation de tert-butyl 6-cyano-5-hydroxy-3-oxohexanoate |
| EP1678148A1 (fr) * | 2003-10-22 | 2006-07-12 | Ranbaxy Laboratories Limited | Procede de preparation de rosuvastatine calcique amorphe |
| GB0324791D0 (en) * | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
| TW200526596A (en) | 2003-11-24 | 2005-08-16 | Teva Pharma | Crystalline ammonium salts of rosuvastatin |
| MY147202A (en) * | 2003-11-26 | 2012-11-14 | Novartis Ag | Compositions comprising organic compounds |
| CA2546894C (fr) | 2003-12-02 | 2009-09-08 | Teva Pharmaceutical Industries Ltd. | Norme de reference pour la caracterisation de la rosuvastatine |
| TWI328006B (en) * | 2003-12-26 | 2010-08-01 | Nissan Chemical Ind Ltd | Crystal form of quinoline compound and process for its production |
| EP1711489B1 (fr) * | 2003-12-29 | 2012-12-26 | LEK Pharmaceuticals d.d. | Procede pour preparer un compose amorphe d'acide (4r-cis)-6-[2-[3-phenyl-4-(phenylcarbamoyl)-2-(4-fluorophenyl)-5-(1-methyl)-pyrrol-1-yl]-ethyl]-2,2-dimethyl-[1,3]-dioxane-4-yl-acetique |
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| WO2007125547A2 (fr) * | 2006-05-03 | 2007-11-08 | Manne Satyanarayana Reddy | Nouveau procédé faisant intervenir des statines et leurs sels acceptables sur le plan pharmaceutique |
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| EP2022784A1 (fr) | 2007-08-08 | 2009-02-11 | LEK Pharmaceuticals D.D. | Procédé pour la préparation d'ester méthylique de rosuvastatine |
| WO2010089770A2 (fr) | 2009-01-19 | 2010-08-12 | Msn Laboratories Limited | Procédé amélioré d'élaboration d'acide (3r,5s)-7-[2-cyclopropyl-4-(4-fluorophényl)quinolin-3-yl]-3,5-dihydroxy-6(e)-heptènoïque de haute pureté, y compris ses sels pharmaceutiquement acceptables |
| EP2526099B1 (fr) | 2010-01-18 | 2016-03-30 | MSN Laboratories Limited | Procédé amélioré pour la préparation d'intermédiaires amides et leur utilisation |
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| CN102875504A (zh) * | 2011-07-13 | 2013-01-16 | 华南理工大学 | 4,5,6,7-四氢普伐他汀及其盐在心血管上的用途 |
| CN102302452B (zh) * | 2011-09-14 | 2012-11-21 | 海南美大制药有限公司 | 匹伐他汀钙脂质体固体制剂 |
| CN102796036B (zh) * | 2012-09-12 | 2014-06-04 | 江苏阿尔法药业有限公司 | 一种阿托伐他汀钙的制备方法 |
| CN103724278B (zh) * | 2013-12-12 | 2019-03-29 | 江苏阿尔法药业有限公司 | 他汀类中间体及其衍生物的制备方法 |
| CN106029895B (zh) * | 2014-02-06 | 2021-07-16 | 株式会社Api | 瑞舒伐他汀钙及其中间体的生产方法 |
| KR20160126700A (ko) | 2015-04-24 | 2016-11-02 | 미래파인켐 주식회사 | 스타틴의 중간체, 이의 제조방법 및 이를 이용한 로수바스타틴의 제조방법 |
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| CN105017231B (zh) * | 2015-06-26 | 2018-01-26 | 上海应用技术学院 | 多取代吲哚类他汀含氟修饰物及其用途 |
| CN113620871A (zh) | 2015-08-05 | 2021-11-09 | 株式会社Api | 生产匹伐他汀钙的方法 |
| CN111362856B (zh) * | 2020-04-29 | 2023-08-18 | 福建海西新药创制股份有限公司 | 一种利用微反应装置生产阿托伐他汀钙的方法 |
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| IL156055A0 (en) * | 2000-11-30 | 2003-12-23 | Teva Pharma | Novel crystal forms of atorvastatin hemi calcium and processes for their preparation as well as novel processes for preparing other forms |
| AU2007205725A1 (en) * | 2000-11-30 | 2007-08-30 | Teva Pharmaceutical Industries Ltd. | Novel cyrstal forms of atorvastatin hemi-calcium and processes for their preparation as well as novel processes for preparing other forms |
| PL365312A1 (en) * | 2000-12-27 | 2004-12-27 | Teva Pharmaceutical Industries Ltd | Crystalline forms of atorvastatin |
| CA2456095C (fr) * | 2001-08-31 | 2010-05-11 | Morepen Laboratories Ltd. | Procede ameliore de preparation d'un sel d'atorvastatine calcique amorphe (2:1) |
-
2002
- 2002-08-16 SK SK140-2004A patent/SK1402004A3/sk not_active Application Discontinuation
- 2002-08-16 WO PCT/US2002/026012 patent/WO2003016317A1/fr active IP Right Grant
- 2002-08-16 HU HU0500616A patent/HUP0500616A3/hu unknown
- 2002-08-16 NZ NZ529913A patent/NZ529913A/en unknown
- 2002-08-16 EP EP02759374A patent/EP1425287A4/fr not_active Withdrawn
- 2002-08-16 PL PL02370407A patent/PL370407A1/xx unknown
- 2002-08-16 IL IL16007702A patent/IL160077A0/xx active IP Right Grant
- 2002-08-16 CZ CZ2004337A patent/CZ2004337A3/cs unknown
- 2002-08-16 AU AU2002324715A patent/AU2002324715B2/en not_active Expired - Fee Related
- 2002-08-16 JP JP2003521239A patent/JP4188826B2/ja not_active Expired - Lifetime
- 2002-08-16 TR TR2003/02281T patent/TR200302281T2/xx unknown
- 2002-08-16 CA CA2450820A patent/CA2450820C/fr not_active Expired - Fee Related
- 2002-08-16 MX MXPA04001451A patent/MXPA04001451A/es not_active Application Discontinuation
- 2002-08-16 CN CNB028159993A patent/CN100430405C/zh not_active Expired - Fee Related
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2004
- 2004-01-27 IL IL160077A patent/IL160077A/en not_active IP Right Cessation
- 2004-02-11 IS IS7148A patent/IS7148A/is unknown
- 2004-03-15 NO NO20041082A patent/NO20041082L/no not_active Application Discontinuation
- 2004-03-15 HR HR20040255A patent/HRPK20040255B3/xx not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| HRP20040255A2 (en) | 2004-08-31 |
| SK1402004A3 (sk) | 2005-01-03 |
| JP4188826B2 (ja) | 2008-12-03 |
| IL160077A (en) | 2007-10-31 |
| PL370407A1 (en) | 2005-05-30 |
| IS7148A (is) | 2004-02-11 |
| TR200302281T2 (tr) | 2004-09-21 |
| WO2003016317A1 (fr) | 2003-02-27 |
| IL160077A0 (en) | 2004-06-20 |
| CN1543468A (zh) | 2004-11-03 |
| EP1425287A1 (fr) | 2004-06-09 |
| CN100430405C (zh) | 2008-11-05 |
| AU2002324715B2 (en) | 2009-03-12 |
| HRPK20040255B3 (en) | 2006-02-28 |
| HUP0500616A2 (hu) | 2005-11-28 |
| MXPA04001451A (es) | 2005-02-17 |
| NZ529913A (en) | 2005-03-24 |
| JP2009024008A (ja) | 2009-02-05 |
| HUP0500616A3 (en) | 2011-07-28 |
| NO20041082L (no) | 2004-03-15 |
| JP2005500382A (ja) | 2005-01-06 |
| CZ2004337A3 (cs) | 2005-01-12 |
| CA2450820C (fr) | 2011-03-15 |
| EP1425287A4 (fr) | 2005-09-07 |
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