RU2005138370A - Улучшенный способ получения кальциевой солироузвастатина - Google Patents
Улучшенный способ получения кальциевой солироузвастатина Download PDFInfo
- Publication number
- RU2005138370A RU2005138370A RU2005138370/04A RU2005138370A RU2005138370A RU 2005138370 A RU2005138370 A RU 2005138370A RU 2005138370/04 A RU2005138370/04 A RU 2005138370/04A RU 2005138370 A RU2005138370 A RU 2005138370A RU 2005138370 A RU2005138370 A RU 2005138370A
- Authority
- RU
- Russia
- Prior art keywords
- aqueous
- methyl
- calcium salt
- solution
- methylsulfonyl
- Prior art date
Links
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title 1
- 229910052791 calcium Inorganic materials 0.000 title 1
- 239000011575 calcium Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 16
- 159000000007 calcium salts Chemical class 0.000 claims 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 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 3
- 159000000000 sodium salts Chemical class 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 2
- 150000005215 alkyl ethers Chemical class 0.000 claims 2
- 239000011260 aqueous acid Substances 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 2
- 239000012266 salt solution Substances 0.000 claims 2
- 238000005406 washing Methods 0.000 claims 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical group [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- -1 alkali metal salt Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000001110 calcium chloride Substances 0.000 claims 1
- 229910001628 calcium chloride Inorganic materials 0.000 claims 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical group CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 239000008096 xylene Substances 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (16)
1. Способ образования кальциевой соли (Е)-7-[4-(4-фторфенил)-6-изопропил-2-[метил(метилсульфонил)амино]пиримидин-5-ил](3R,5S)-3,5-дигидроксигепт-6-еновой кислоты, включающий стадии (а)-(ж):
а) взаимодействие (1-6С)алкилового эфира (Е)-(6-{2-[4-(4-фторфенил)-6-изопропил-2-[метил(метилсульфонил)амино]пиримидин-5-ил]винил}(4R,6S)-2,2-диметил[1,3]диоксан-4-ил)уксусной кислоты в смешиваемом с водой органическом растворителе с водной кислотой при повышенной температуре;
б) взаимодействие полученного раствора с водным гидроксидом щелочного метала и, возможно, промывание полученного водного раствора соли щелочного металла подходящим органическим растворителем;
в) доведение рН полученного раствора до значения в интервале от рН 6 до рН-11;
г) удаление смешиваемого с водой органического растворителя;
д) возможная фильтрация полученной смеси;
е) добавление водорастворимой кальциевой соли к фильтрату так, чтобы образовалась кальциевая соль (Е)-7-[4-(4-фторфенил)-6-изопропил-2-[метил(метилсульфонил)амино]пиримидин-5-ил](1R,5S)-3,5-дигидроксигепт-6-еновой кислоты; и
ж) выделение продукта стадии (е).
2. Способ по п.1, при котором смешиваемый с водной органический растворитель представляет собой ацетонитрил.
3. Способ по п.1, при котором водная кислота на стадии (а) представляет собой соляную кислоту.
4. Способ по п.1, при котором стадия (б) включает взаимодействие полученного раствора с водным гидроксидом натрия и промывание полученного водного раствора натриевой соли подходящим углеводородным, сложноэфирным или эфирным растворителем.
5. Способ по п.1, при котором водный раствор натриевой соли промывают толуолом, ксилолом, МТВЕ (метил-трет-бутиловым эфиром) или этилацетатом.
6. Способ по п.5, при котором водный раствор натриевой соли промывают толуолом.
7. Способ по п.1, при котором (1-6С)алкиловый эфир представляет собой трет-бутиловый эфир.
8. Способ по п.1, при котором стадию (а) осуществляют при 35-40°С.
9. Способ по п.1, при котором стадию (б) осуществляют при температуре окружающей среды.
10. Способ по п.1, при котором на стадии (б) водный гидроксид щелочного металла представляет собой гидроксид калия.
11. Способ по п.1, при котором стадия (в) включает доведение рН раствора до приблизительно рН 9-10,5 путем добавления водной соляной кислоты.
12. Способ по п.1, при котором стадию (г) выполняют при давлении меньшем или равном 55 мбар (5,5·103 Па) и температуре меньшей или равной 45°С.
13. Способ по п.1, при котором на стадии (е) водорастворимая кальциевая соль представляет собой хлорид кальция.
14. Способ по любому из пп.1-13, при котором на стадии (е) кальциевую соль добавляют при 32-43°С.
15. Соединение - кальциевая соль (Е)-7-[4-(4-фторфенил)-6-изопропил-2-[метил(метилсульфонил)амино]пиримидин-5-ил](3R,5S)-3,5-дигидроксигепт-6-еновой кислоты, получаемое посредством стадий (а)-(ж) способа по п.1.
16. Соединение - кальциевая соль (Е)-7-[4-(4-фторфенил)-6-изопропил-2-[метил(метилсульфонил)амино]пиримидин-5-ил](3R,5S)-3,5-дигидроксигепт-6-еновой кислоты, получаемое посредством стадий (а)-(ж) способа по п.7.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0312896.4A GB0312896D0 (en) | 2003-06-05 | 2003-06-05 | Chemical process |
GB0312896.4 | 2003-06-05 | ||
GBGB0324793.9A GB0324793D0 (en) | 2003-06-05 | 2003-10-24 | Chemical process |
GB0324793.9 | 2003-10-24 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU2005138370A true RU2005138370A (ru) | 2006-07-10 |
RU2361864C2 RU2361864C2 (ru) | 2009-07-20 |
Family
ID=33512687
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2005138370/04A RU2361864C2 (ru) | 2003-06-05 | 2004-06-03 | Способ образования кальциевой соли (е)-7-[4-(4-фторфенил)-6-изопропил-2-[метил(метилсульфонил)амино]пиримидин-5-ил](3r,5s)-3,5-дигидроксигепт-6-еновой кислоты (кальциевой соли розувастатина) |
Country Status (26)
Country | Link |
---|---|
US (1) | US8063213B2 (ru) |
EP (1) | EP1633727B1 (ru) |
JP (1) | JP4651615B2 (ru) |
KR (1) | KR101099934B1 (ru) |
CN (1) | CN100422157C (ru) |
AR (1) | AR044773A1 (ru) |
AT (1) | ATE464297T1 (ru) |
AU (1) | AU2004245291B2 (ru) |
BR (1) | BRPI0410922B8 (ru) |
CA (1) | CA2527314C (ru) |
CO (1) | CO5640116A2 (ru) |
DE (1) | DE602004026576D1 (ru) |
ES (1) | ES2341858T3 (ru) |
GB (2) | GB0312896D0 (ru) |
HK (1) | HK1087405A1 (ru) |
IL (1) | IL172075A (ru) |
IS (1) | IS2751B (ru) |
MX (1) | MXPA05013128A (ru) |
MY (1) | MY140820A (ru) |
NO (1) | NO332971B1 (ru) |
NZ (1) | NZ543962A (ru) |
RU (1) | RU2361864C2 (ru) |
SA (1) | SA04250223B1 (ru) |
TW (1) | TWI341310B (ru) |
UY (1) | UY28341A1 (ru) |
WO (1) | WO2004108691A1 (ru) |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0003305D0 (en) | 2000-02-15 | 2000-04-05 | Zeneca Ltd | Pyrimidine derivatives |
GB0011120D0 (en) | 2000-05-09 | 2000-06-28 | Avecia Ltd | Process |
NL1015744C2 (nl) * | 2000-07-19 | 2002-01-22 | Dsm Nv | Werkwijze voor de bereiding van 2-(6-gesubstitueerde-1,3-dioxan-4-yl) azijnzuurderivaten. |
HUP0401248A3 (en) | 2001-07-13 | 2004-11-29 | Astrazeneca Uk Ltd | Preparation of aminopyrimidine compounds and new intermediates |
EP1323717A1 (en) | 2001-12-27 | 2003-07-02 | Dsm N.V. | Process for the preparation of 2-(6-Substituted-1,3-Dioxane-4-yL) acetic acid derivatives |
EP1375493A1 (en) | 2002-06-17 | 2004-01-02 | Dsm N.V. | Process for the preparation of an dioxane acetic acid ester |
GB0218781D0 (en) | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
JP4579821B2 (ja) | 2002-12-16 | 2010-11-10 | アストラゼネカ・ユーケイ・リミテッド | ピリミジン化合物を製造するための方法 |
GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
UY28501A1 (es) | 2003-09-10 | 2005-04-29 | Astrazeneca Uk Ltd | Compuestos químicos |
GB0322552D0 (en) | 2003-09-26 | 2003-10-29 | Astrazeneca Uk Ltd | Therapeutic treatment |
GB0324791D0 (en) * | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
US7851624B2 (en) | 2003-12-24 | 2010-12-14 | Teva Pharamaceutical Industries Ltd. | Triol form of rosuvastatin and synthesis of rosuvastatin |
EP1737828A1 (en) * | 2004-01-19 | 2007-01-03 | Ranbaxy Laboratories Limited | Amorphous magnesium salts of rosuvastatin |
GB0428328D0 (en) | 2004-12-24 | 2005-02-02 | Astrazeneca Uk Ltd | Chemical process |
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 |
SI1915349T1 (sl) | 2005-06-24 | 2016-05-31 | Lek Pharmaceuticals D.D. | Postopek za pripravo čistega amorfnega rosuvastatin kalcija |
CZ299215B6 (cs) * | 2005-06-29 | 2008-05-21 | Zentiva, A. S. | Zpusob výroby hemivápenaté soli (E)-7-[4-(4-fluorofenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl] (3R,5S)-3,5-dihydroxy-6-heptenovékyseliny |
GB0514078D0 (en) * | 2005-07-08 | 2005-08-17 | Astrazeneca Uk Ltd | Chemical process |
WO2007022488A2 (en) | 2005-08-16 | 2007-02-22 | Teva Pharmaceutical Industries Ltd. | Crystalline rosuvastatin intermediate |
MX2007004423A (es) * | 2005-08-16 | 2007-06-14 | Teva Pharma | Calcio de rosuvastatina con bajo contenido de sal. |
HU227696B1 (en) * | 2006-04-13 | 2011-12-28 | Egyt Gyogyszervegyeszeti Gyar | Zinc salt of rosuvastatin, process for its preparation and pharmaceutical compositions containing it |
US8455640B2 (en) | 2006-05-03 | 2013-06-04 | Msn Laboratories Limited | Process for statins and its pharmaceutically acceptable salts thereof |
US8404841B2 (en) | 2006-10-09 | 2013-03-26 | Msn Laboratories Limited | Process for the preparation of statins and their pharmaceutically acceptable salts thereof |
TW200831469A (en) * | 2006-12-01 | 2008-08-01 | Astrazeneca Uk Ltd | Chemical process |
HU230981B1 (hu) * | 2007-10-12 | 2019-08-28 | Egis Gyógyszergyár Nyilvánosan Működő Részvénytársaság | Eljárás rosuvastatin só előállítására |
WO2009143776A1 (zh) | 2008-05-27 | 2009-12-03 | 常州制药厂有限公司 | 瑞舒伐他汀钙盐的制备方法及其中间体 |
EP2138165A1 (en) | 2008-06-27 | 2009-12-30 | KRKA, tovarna zdravil, d.d., Novo mesto | Pharmaceutical composition comprising a statin |
WO2009156173A1 (en) | 2008-06-27 | 2009-12-30 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Pharmaceutical composition comprising a statin |
US20110245285A1 (en) * | 2008-09-09 | 2011-10-06 | Biocon Limited | Process for preparation of rosuvastatin acetonide calcium |
EP2373609B1 (en) | 2008-12-19 | 2013-10-16 | KRKA, D.D., Novo Mesto | Use of amphiphilic compounds for controlled crystallization of statins and statin intermediates |
EP2327682A1 (en) | 2009-10-29 | 2011-06-01 | KRKA, D.D., Novo Mesto | Use of amphiphilic compounds for controlled crystallization of statins and statin intermediates |
EP2387561A4 (en) | 2009-01-19 | 2012-07-25 | Msn Lab Ltd | IMPROVED PROCESS FOR THE PREPARATION OF HIGH-PURITY (3R, 5S) -7-β-CYCLOPROPYL-4- (4-FLUOROPHENYL) QUINOLIN-3-YL-3,5-DIHYDROXY-6 (E) -HEPTENOIC ACID, INCLUDING ITS PHARMACEUTICALLY ACCEPTABLE SALTS |
WO2011086584A2 (en) | 2010-01-18 | 2011-07-21 | Msn Laboratories Limited | Improved process for the preparation of amide intermediates and their use thereof |
WO2011132172A1 (en) | 2010-04-23 | 2011-10-27 | Ranbaxy Laboratories Limited | NOVEL INTERMEDIATES FOR THE PREPARATION OF HMG-CoA REDUCTASE INHIBITORS |
WO2012011129A2 (en) * | 2010-07-22 | 2012-01-26 | Msn Laboratories Limited | Novel polymorph of bis[(e)-7-[4-(4-fluorophenyl)-6-iso-propyl-2-[methyl (methylsulfonyl)amino]pyrimidin-5-yl](3r,5s)-3,5-dihydroxyhept-6-enoic acid] calcium salt |
CN105753834B (zh) * | 2016-03-25 | 2018-08-21 | 河南师范大学 | 一种瑞舒伐他汀钙关键手性中间体的合成方法 |
Family Cites Families (69)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4645858A (en) | 1982-03-22 | 1987-02-24 | G. D. Searle & Co. | Pentanedioic acid derivatives |
DE3741509A1 (de) | 1987-12-08 | 1989-06-22 | Hoechst Ag | Verfahren zur herstellung optisch aktiver 3-desmethylmevalonsaeurederivate sowie zwischenprodukte |
EP0367895A1 (en) | 1988-10-06 | 1990-05-16 | Sandoz Ag | Pyrimidinyl-substituted hydroxyacids, lactones and esters and pharmaceutical compositions containing them |
US5026698A (en) | 1988-11-02 | 1991-06-25 | Nissan Chemical Industries, Ltd. | Thienopyridine type mevalonolactones |
JP2648897B2 (ja) * | 1991-07-01 | 1997-09-03 | 塩野義製薬株式会社 | ピリミジン誘導体 |
WO1993008823A1 (en) | 1991-11-06 | 1993-05-13 | Tanabe Seiyaku Co., Ltd. | Guanidinyl and related cell adhesion modulation compounds |
US5278313A (en) | 1992-03-27 | 1994-01-11 | E. R. Squibb & Sons, Inc. | Process for the preparation of 1,3-dioxane derivatives useful in the preparation of HMG-COA reductase inhibitors |
SG44830A1 (en) | 1992-07-02 | 1997-12-19 | Hoechst Ag | Process for preparing tert-butyl 93R,5S) -6 Hydroxy-3,5-O-Isopropylidene-3, 5-Dihydroxyhexanoate |
CZ294108B6 (cs) | 1995-07-17 | 2004-10-13 | Warner@Lambertácompany | Krystalická forma I hydrátu atorvastatinuŹ tj@ semivápenaté soli kyseliny [R@}RgŹRgB]@}@fluorfenylB@betaŹdelta@dihydroxy@Q@}�@methylethylB@fenyl[}fenylaminoBkarbonyl]@�H@pyrrol@�@heptanové |
US6278001B1 (en) | 1995-11-28 | 2001-08-21 | L'oréal | Method for preparing (+) compactin and (+) mevinolin analog compounds having a β-hydroxy-δ-lactone grouping |
FR2741620B1 (fr) | 1995-11-28 | 1997-12-26 | Oreal | Procede de preparation de composes a groupement beta-hydroxy -delta-lactone analogues de la (+) compactine et de la (+) mevinoline |
AU3366297A (en) | 1996-06-24 | 1998-01-14 | Astra Aktiebolag | Polymorphic compounds |
EP1533308B1 (en) | 1998-12-10 | 2014-01-15 | Kaneka Corporation | A process for producing a simvastatin precursor |
GB9900339D0 (en) * | 1999-01-09 | 1999-02-24 | Zeneca Ltd | Chemical compounds |
GB9903472D0 (en) * | 1999-02-17 | 1999-04-07 | Zeneca Ltd | Chemical process |
AU7717500A (en) | 1999-09-30 | 2001-04-30 | Merck & Co., Inc. | Anti-hypercholesterolemic drug combination |
JP2003514798A (ja) | 1999-11-17 | 2003-04-22 | テバ ファーマシューティカル インダストリーズ リミティド | アトルバスタチンカルシウムの多形 |
GB0001621D0 (en) | 2000-01-26 | 2000-03-15 | Astrazeneca Ab | Pharmaceutical compositions |
GB0003305D0 (en) | 2000-02-15 | 2000-04-05 | Zeneca Ltd | Pyrimidine derivatives |
WO2001072706A1 (en) | 2000-03-28 | 2001-10-04 | Biocon India Limited | Synthesis of [r-(r*,r*)]-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrole-1-heptanoic acid hemi calcium salt (atorvastatin) |
GB0011120D0 (en) * | 2000-05-09 | 2000-06-28 | Avecia Ltd | Process |
GB0011163D0 (en) | 2000-05-10 | 2000-06-28 | Astrazeneca Ab | Chemical compound |
NL1015744C2 (nl) * | 2000-07-19 | 2002-01-22 | Dsm Nv | Werkwijze voor de bereiding van 2-(6-gesubstitueerde-1,3-dioxan-4-yl) azijnzuurderivaten. |
EP1330245A4 (en) | 2000-10-05 | 2004-10-20 | Biogal Gyogyszergyar | PRAVASTATIN SODIUM, ESSENTIALLY FREE OF PRAVASTATIN LACTONE AND EPIPRAVASTATIN, AND COMPOSITIONS CONTAINING THIS |
US6528661B2 (en) | 2000-11-16 | 2003-03-04 | Teva Pharmaceutical Industries Ltd. | 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 |
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 |
NL1017548C2 (nl) | 2001-03-09 | 2002-09-10 | Synthon Bv | Een lactonisatie proces. |
IN190564B (ru) | 2001-04-11 | 2003-08-09 | Cadila Heathcare Ltd | |
IL158525A0 (en) | 2001-06-06 | 2004-05-12 | Bristol Myers Squibb Co | A process for preparing chiral diol sulfone derivatives |
HUP0401248A3 (en) * | 2001-07-13 | 2004-11-29 | Astrazeneca Uk Ltd | Preparation of aminopyrimidine compounds and new intermediates |
KR20040026705A (ko) | 2001-08-16 | 2004-03-31 | 테바 파마슈티컬 인더스트리즈 리미티드 | 스타틴의 칼슘 염 형태의 제조 방법 |
JP4188826B2 (ja) | 2001-08-16 | 2008-12-03 | テバ ファーマシューティカル インダストリーズ リミティド | カルシウム塩型スタチンの製造方法 |
CN1545502A (zh) | 2001-08-22 | 2004-11-10 | �������⻯ѧƷ�ع�����˾ | 吲哚衍生物的制备方法 |
WO2003026573A2 (en) | 2001-09-24 | 2003-04-03 | Merck & Co., Inc. | Screening and selection methods for statin drug combinations |
EP1323717A1 (en) * | 2001-12-27 | 2003-07-02 | Dsm N.V. | Process for the preparation of 2-(6-Substituted-1,3-Dioxane-4-yL) acetic acid derivatives |
KR100511533B1 (ko) | 2002-04-09 | 2005-08-31 | 임광민 | 키랄 중간체, 그의 제조방법 및 그를 이용한 HMG-CoA환원저해제의 제조방법 |
BR0311195A (pt) | 2002-05-21 | 2005-02-22 | Ranbaxy Lab Ltd | Processo de preparação de rosuvastatina |
EP1375493A1 (en) * | 2002-06-17 | 2004-01-02 | Dsm N.V. | Process for the preparation of an dioxane acetic acid ester |
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 |
JP4579821B2 (ja) | 2002-12-16 | 2010-11-10 | アストラゼネカ・ユーケイ・リミテッド | ピリミジン化合物を製造するための方法 |
AU2004228607B2 (en) | 2003-04-11 | 2011-01-27 | Lek Pharmaceuticals D.D. | Process for the preparation of amorphous calcium salt of atorvastatin |
WO2004103977A2 (en) | 2003-05-21 | 2004-12-02 | Ciba Specialty Chemicals Holding Inc. | Process for the preparation of pyrimidine derivatives |
GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
AU2003247327A1 (en) | 2003-07-15 | 2005-01-28 | Eos Eczacibasi Ozgun Kimyasal Urunler Sanyi Ve Ticaret A.S. | Process for the preparation of amortphous atorvastatin calcium without interconversion of any crystalline form |
EP1562912A2 (en) | 2003-08-28 | 2005-08-17 | Teva Pharmaceutical Industries Limited | Process for preparation of rosuvastatin calcium |
UY28501A1 (es) | 2003-09-10 | 2005-04-29 | Astrazeneca Uk Ltd | Compuestos químicos |
GB0321827D0 (en) | 2003-09-18 | 2003-10-15 | Astrazeneca Uk Ltd | Chemical compounds |
GB0322552D0 (en) | 2003-09-26 | 2003-10-29 | Astrazeneca Uk Ltd | Therapeutic treatment |
WO2005040134A1 (en) | 2003-10-22 | 2005-05-06 | Ranbaxy Laboratories Limited | Process for the preparation of amorphous rosuvastatin calcium |
GB0324791D0 (en) * | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
DE10352659B4 (de) | 2003-11-11 | 2007-09-13 | Ratiopharm Gmbh | Verfahren zur Herstellung von Statinen und Tetrahydropyranonderivate zur Verwendung in dem Verfahren |
EP1601658A1 (en) | 2003-11-24 | 2005-12-07 | Teva Pharmaceutical Industries Limited | Crystalline ammonium salts of rosuvastatin |
ATE507209T1 (de) | 2003-12-02 | 2011-05-15 | Teva Pharma | Referenzstandard zur charakterisierung von rosuvastatin |
WO2005054207A1 (en) | 2003-12-04 | 2005-06-16 | Glenmark Pharmaceuticals Limited | Process for the preparation of pyrimidine derivatives |
CA2645396A1 (en) | 2003-12-24 | 2005-07-14 | Teva Pharmaceutical Industries, Ltd | Process for preparation of statins with high syn to anti ratio |
CZ200486A3 (cs) | 2004-01-16 | 2005-08-17 | Zentiva, A.S. | Způsob výroby hemivápenaté soli (E)-7-[4-(4-fluorfenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxy-6-heptenové kyseliny |
EP1709008A1 (en) | 2004-01-19 | 2006-10-11 | Ranbaxy Laboratories Limited | Salts of hmg-coa reductase inhibitors and use thereof |
EP1737828A1 (en) | 2004-01-19 | 2007-01-03 | Ranbaxy Laboratories Limited | Amorphous magnesium salts of rosuvastatin |
US7241800B2 (en) | 2004-03-17 | 2007-07-10 | Mai De Ltd. | Anhydrous amorphous form of fluvastatin sodium |
GB0406757D0 (en) | 2004-03-26 | 2004-04-28 | Avecia Ltd | Process and compounds |
US7161004B2 (en) | 2004-06-21 | 2007-01-09 | Dr. Reddy's Laboratories Limited | Processes to produce intermediates for rosuvastatin |
EP1673351A1 (en) | 2004-07-13 | 2006-06-28 | Teva Pharmaceutical Industries Ltd. | A process for the preparation of rosuvastatin involving a tempo-mediated oxidation step |
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 |
CA2498978A1 (en) | 2005-02-28 | 2006-08-28 | Apotex Pharmachem Inc. | An improved process for the preparation of atorvastatin and intermediates |
GB0514078D0 (en) | 2005-07-08 | 2005-08-17 | Astrazeneca Uk Ltd | Chemical process |
TW200831469A (en) * | 2006-12-01 | 2008-08-01 | Astrazeneca Uk Ltd | Chemical process |
-
2003
- 2003-06-05 GB GBGB0312896.4A patent/GB0312896D0/en not_active Ceased
- 2003-10-24 GB GBGB0324793.9A patent/GB0324793D0/en not_active Ceased
-
2004
- 2004-05-24 TW TW093114667A patent/TWI341310B/zh active
- 2004-06-02 UY UY28341A patent/UY28341A1/es not_active Application Discontinuation
- 2004-06-03 RU RU2005138370/04A patent/RU2361864C2/ru active
- 2004-06-03 US US10/558,390 patent/US8063213B2/en active Active
- 2004-06-03 CN CNB2004800154822A patent/CN100422157C/zh not_active Expired - Lifetime
- 2004-06-03 JP JP2006508394A patent/JP4651615B2/ja not_active Expired - Lifetime
- 2004-06-03 BR BRPI0410922A patent/BRPI0410922B8/pt active IP Right Grant
- 2004-06-03 AT AT04735910T patent/ATE464297T1/de not_active IP Right Cessation
- 2004-06-03 CA CA2527314A patent/CA2527314C/en not_active Expired - Fee Related
- 2004-06-03 MY MYPI20042138A patent/MY140820A/en unknown
- 2004-06-03 ES ES04735910T patent/ES2341858T3/es not_active Expired - Lifetime
- 2004-06-03 MX MXPA05013128A patent/MXPA05013128A/es active IP Right Grant
- 2004-06-03 WO PCT/GB2004/002373 patent/WO2004108691A1/en active Application Filing
- 2004-06-03 EP EP04735910A patent/EP1633727B1/en not_active Expired - Lifetime
- 2004-06-03 AU AU2004245291A patent/AU2004245291B2/en not_active Expired
- 2004-06-03 KR KR1020057023329A patent/KR101099934B1/ko active IP Right Grant
- 2004-06-03 DE DE602004026576T patent/DE602004026576D1/de not_active Expired - Lifetime
- 2004-06-03 NZ NZ543962A patent/NZ543962A/en unknown
- 2004-06-04 AR ARP040101944A patent/AR044773A1/es unknown
- 2004-07-14 SA SA04250223A patent/SA04250223B1/ar unknown
-
2005
- 2005-11-21 IL IL172075A patent/IL172075A/en active IP Right Grant
- 2005-12-02 CO CO05122683A patent/CO5640116A2/es unknown
- 2005-12-05 NO NO20055730A patent/NO332971B1/no not_active IP Right Cessation
-
2006
- 2006-01-02 IS IS8217A patent/IS2751B/is unknown
- 2006-07-05 HK HK06107580.5A patent/HK1087405A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
RU2005138370A (ru) | Улучшенный способ получения кальциевой солироузвастатина | |
RU2006117337A (ru) | Способ получения кальциевой соли розувастатина(е)-7-[4-(4-фторфенил)-6-изопропил-2-[метил(метилсульфонил)амино]пиримидин-5-ил](3r, 5s)-3, 5-дигидроксигепт-6-еновой кислоты и его кристаллических промежуточных соединений | |
JP5127460B2 (ja) | 化学的方法 | |
JP2003518474A5 (ru) | ||
NO329439B1 (no) | Fremgangsmate for fremstilling av kalsiumsaltet fra rosuvastatin | |
WO2007000121A1 (en) | A method for the production of the hemi-calcium salt of (e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3r,5s)-3,5-dihydroxyhept-6-enoic acid | |
NO320739B1 (no) | Forbindelser og fremgangsmate for fremstilling av tert-butyl (E)-(6{2-[4-(4-fluorfenyl)-6-isopropyl-2-[metyl(metylsulfonyl)amino]pyrimidin-5-yl]vinyl}(4R,6S)-2,2-dimetyl[1,3]dioksan-4-yl)acetat | |
JP2006500347A5 (ru) | ||
DK1144389T3 (da) | Krystallinsk bis(E)-7-[4-(4-fluorphenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-ensyre]calciumsalt | |
BRPI0612851A2 (pt) | processos para a fabricação de um composto, e para formar um composto ou um sal farmaceuticamente aceitável do mesmo, e, composto | |
EP2526099A2 (en) | Improved process for the preparation of amide intermediates and their use thereof | |
WO2007099561A1 (en) | Process for preparing rosuvastatin calcium | |
EP1902036B1 (en) | Process for the preparation of rosuvastatin and intermediates | |
EP1704144B1 (en) | A method of preparation of the hemi-calcium salt of (e)-7- [4-(4-fluorophenyl)-6-isopropyl-2- [me thyl(methylsulfonyl)amino]pyrimidin-5-yl](3r,5s)-3,5-dihydroxy-6-heptenoic acid | |
AU2008212622B2 (en) | An improved process for preparation of rosuvastatin calcium | |
WO2005021511A1 (en) | A novel process for amorphous rosuvastatin calcium | |
ZA200509539B (en) | Improved production of rosuvastatin calcium salt |