WO2003097614A3 - Process for the preparation of rosuvastatin - Google Patents

Process for the preparation of rosuvastatin Download PDF

Info

Publication number
WO2003097614A3
WO2003097614A3 PCT/IB2003/001946 IB0301946W WO03097614A3 WO 2003097614 A3 WO2003097614 A3 WO 2003097614A3 IB 0301946 W IB0301946 W IB 0301946W WO 03097614 A3 WO03097614 A3 WO 03097614A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
rosuvastatin
pyrimidinecarboxaldehyde
methylsulphonylamino
fluorophenyl
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
Application number
PCT/IB2003/001946
Other languages
French (fr)
Other versions
WO2003097614A2 (en
Inventor
Yatendra Kumar
Shantanu De
Mohammad Rafeeq
Hashim Nizar Poovanathi Meeran
Swargam Sathyanarayana
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ranbaxy Laboratories Ltd
Original Assignee
Ranbaxy Laboratories Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ranbaxy Laboratories Ltd filed Critical Ranbaxy Laboratories Ltd
Priority to AU2003228010A priority Critical patent/AU2003228010A1/en
Priority to BR0311195-4A priority patent/BR0311195A/en
Priority to US10/515,361 priority patent/US20050222415A1/en
Priority to EP03725478A priority patent/EP1585736A2/en
Priority to EA200401533A priority patent/EA200401533A1/en
Publication of WO2003097614A2 publication Critical patent/WO2003097614A2/en
Publication of WO2003097614A3 publication Critical patent/WO2003097614A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to a cost effective and industrially advantageous process for the preparation of 4-4(fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulphonylamino)-5-pyrimidinecarboxaldehyde, referred to here as pyrimidine aldehyde of structural Formula I and to the use of this compound as intermediate for the preparation of rosuvastatin.
PCT/IB2003/001946 2002-05-21 2003-05-21 Process for the preparation of rosuvastatin Ceased WO2003097614A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU2003228010A AU2003228010A1 (en) 2002-05-21 2003-05-21 Process for the preparation of rosuvastatin
BR0311195-4A BR0311195A (en) 2002-05-21 2003-05-21 Rosuvastatin Preparation Process
US10/515,361 US20050222415A1 (en) 2002-05-21 2003-05-21 Process for the preparation of rosuvastatin
EP03725478A EP1585736A2 (en) 2002-05-21 2003-05-21 Process for the preparation of rosuvastatin
EA200401533A EA200401533A1 (en) 2002-05-21 2003-05-21 METHOD OF OBTAINING ROSUVASTATIN

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN575/DEL/2002 2002-05-21
IN575DE2002 2002-05-21

Publications (2)

Publication Number Publication Date
WO2003097614A2 WO2003097614A2 (en) 2003-11-27
WO2003097614A3 true WO2003097614A3 (en) 2004-05-21

Family

ID=29434392

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2003/001946 Ceased WO2003097614A2 (en) 2002-05-21 2003-05-21 Process for the preparation of rosuvastatin

Country Status (7)

Country Link
US (1) US20050222415A1 (en)
EP (1) EP1585736A2 (en)
AR (1) AR039836A1 (en)
AU (1) AU2003228010A1 (en)
BR (1) BR0311195A (en)
EA (1) EA200401533A1 (en)
WO (1) WO2003097614A2 (en)

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IL159741A0 (en) 2001-07-13 2004-06-20 Astrazeneca Uk Ltd Preparation of aminopyrimidine compounds
GB0218781D0 (en) 2002-08-13 2002-09-18 Astrazeneca Ab Chemical process
GB0312896D0 (en) 2003-06-05 2003-07-09 Astrazeneca Ab Chemical process
WO2005021511A1 (en) * 2003-08-27 2005-03-10 Hetero Drugs Limited A novel process for amorphous rosuvastatin calcium
WO2005023778A2 (en) * 2003-08-28 2005-03-17 Teva Pharmaceutical Industries Ltd. Process for preparation of rosuvastatin calcium
EP1816126A1 (en) * 2003-08-28 2007-08-08 Teva Pharmaceutical Industries Limited Process for preparation of rosuvastatin calcium
UY28501A1 (en) 2003-09-10 2005-04-29 Astrazeneca Uk Ltd CHEMICAL COMPOUNDS
GB0324791D0 (en) 2003-10-24 2003-11-26 Astrazeneca Ab Chemical process
EP1601658A1 (en) 2003-11-24 2005-12-07 Teva Pharmaceutical Industries Limited Crystalline ammonium salts of rosuvastatin
US7244844B2 (en) * 2003-12-02 2007-07-17 Teva Pharmaceutical Industries Ltd. Reference standard for characterization of rosuvastatin
US7851624B2 (en) 2003-12-24 2010-12-14 Teva Pharamaceutical Industries Ltd. Triol form of rosuvastatin and synthesis of rosuvastatin
WO2006017357A1 (en) * 2004-07-13 2006-02-16 Teva Pharmaceutical Industries Ltd. A process for the preparation of rosuvastatin involving a tempo-mediated oxidation step
CZ298330B6 (en) * 2004-07-19 2007-08-29 Zentiva, A. S. Process for preparing 4-(4--fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonyl-amino)-5-pyrimidinecarbaldehyde and use thereof
KR100622494B1 (en) * 2004-09-06 2006-09-19 현대자동차주식회사 Assembly structure of steering wheel
CN1763015B (en) * 2004-10-22 2011-06-22 四川抗菌素工业研究所有限公司 Preparation method and intermediate of rosuvastatin and its pharmaceutical salts
CN100351240C (en) * 2005-01-19 2007-11-28 安徽省庆云医药化工有限公司 Rosuvastatin calcium synthesis method
US20070167625A1 (en) * 2005-02-22 2007-07-19 Anna Balanov Preparation of rosuvastatin
KR101020024B1 (en) 2005-02-22 2011-03-09 테바 파마슈티컬 인더스트리즈 리미티드 Rosuvastatin and salts thereof containing no rosuvastatin alkyl ether and preparation method thereof
CN101128437A (en) * 2005-02-22 2008-02-20 特瓦制药工业有限公司 Rosuvastatin and salts thereof free of rosuvastatin alkyl ether and processes for their preparation
US20070037979A1 (en) * 2005-02-22 2007-02-15 Valerie Niddam-Hildesheim Preparation of rosuvastatin
WO2006100689A1 (en) * 2005-03-22 2006-09-28 Unichem Laboratories Limited Process for preparation of rosuvastatin
WO2006106526A1 (en) * 2005-04-04 2006-10-12 Unichem Laboratories Limited Process for preparation of calcium salt of rosuvastatin
EP1893585A1 (en) * 2005-06-01 2008-03-05 Fermion Oy Process for the preparation of n-[4-(4-fluorophenyl)-5-formyl-6-isopropyl-pyrimidin-2-yl]-n-methylmethanesulfonamide
US9150518B2 (en) 2005-06-24 2015-10-06 Lek Pharmaceuticals, D.D. Process for preparing amorphous rosuvastatin calcium of impurities
TW200800918A (en) * 2005-08-16 2008-01-01 Teva Pharma Rosuvastatin calcium with a low salt content
WO2007022488A2 (en) * 2005-08-16 2007-02-22 Teva Pharmaceutical Industries Ltd. Crystalline rosuvastatin intermediate
CN100436428C (en) * 2005-08-22 2008-11-26 鲁南制药集团股份有限公司 Preparation method of rosuvastain and its salt
CA2624801A1 (en) * 2005-10-03 2007-04-12 Teva Pharmaceutical Industries Ltd. Diastereomeric purification of rosuvastatin
WO2007074391A2 (en) * 2005-12-28 2007-07-05 Bakulesh Mafatlal Khamar Preparation of a key intermediate in the synthesis of rosuvastatin
US8455640B2 (en) 2006-05-03 2013-06-04 Msn Laboratories Limited Process for statins and its pharmaceutically acceptable salts thereof
EP1948618A1 (en) * 2006-09-18 2008-07-30 Teva Pharmaceutical Industries Ltd. Crystalline rosuvastatin calcium
US8404841B2 (en) 2006-10-09 2013-03-26 Msn Laboratories Limited Process for the preparation of statins and their pharmaceutically acceptable salts thereof
US8318933B2 (en) 2006-10-31 2012-11-27 Aurobindo Pharma Ltd Process for preparing rosuvastatin calcium
WO2008072078A1 (en) * 2006-12-13 2008-06-19 Aurobindo Pharma Limited An improved process for preparing rosuvastatin caclium
WO2008093205A2 (en) * 2007-01-31 2008-08-07 Orchid Chemicals & Pharmaceuticals Limited A method for the purification of rosuvastatin intermediate
ES2385623T3 (en) 2007-02-08 2012-07-27 Aurobindo Pharma Limited An improved procedure for the preparation of calcium rosuvastatin
US7687660B2 (en) 2007-04-18 2010-03-30 Teva Pharmaceutical Industries Ltd. Process for preparing intermediates of HMG-CoA reductase inhibitors
CN101323597B (en) * 2007-06-11 2012-09-05 安徽省庆云医药化工有限公司 Preparation of 4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonyl amido) pyrimidine-5-formaldehyde
US20090069563A1 (en) 2007-07-12 2009-03-12 Valerie Niddam-Hildesheim Rosuvastatin intermediates and their preparation
EP2022784A1 (en) 2007-08-08 2009-02-11 LEK Pharmaceuticals D.D. Process for the preparation of methyl ester of rosuvastatin
EP2181089A2 (en) 2007-08-28 2010-05-05 Ratiopharm GmbH Process for preparing pentanoic diacid derivatives
WO2009143776A1 (en) 2008-05-27 2009-12-03 常州制药厂有限公司 Preparation method of rosuvastatin calcium and its intermediates
EP2350025A1 (en) * 2008-09-30 2011-08-03 Aurobindo Pharma Limited An improved process for preparing pyrimidine propenaldehyde
EP2752407B1 (en) 2009-01-14 2015-09-23 Krka Tovarna Zdravil, D.D., Novo Mesto Crystalline rosuvastatin calcium trihydrate
EA021942B1 (en) 2009-01-15 2015-10-30 Эгиш Дьёдьсердьяр Зрт. Process for the preparation of rosuvastatin salts
US8487105B2 (en) 2009-01-19 2013-07-16 Msn Laboratories Limited Process for preparing pitavastatin, intermediates and pharmaceuctically acceptable salts thereof
KR101160152B1 (en) * 2009-02-24 2012-06-27 한미사이언스 주식회사 Novel process for preparing statin compound or its salt and intermediate used therein
WO2011086584A2 (en) 2010-01-18 2011-07-21 Msn Laboratories Limited Improved process for the preparation of amide intermediates and their use thereof
WO2011141934A1 (en) 2010-05-13 2011-11-17 Matrix Laboratories Ltd. An improved process for the preparation of an intermediate 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
CN101955463B (en) * 2010-08-04 2012-01-04 重庆博腾制药科技股份有限公司 Method for preparing rosuvastatin calcium intermediate
HU230987B1 (en) 2010-11-29 2019-08-28 Egis Gyógyszergyár Nyrt. Process for the preparation of pharmaceutical intermediates with high purity
EP2785851A2 (en) 2011-11-28 2014-10-08 Mylan Laboratories, Limited Process for producing chiral statin side chain intermediates employing candida antarctica lipase b
CN103134893B (en) * 2013-01-25 2014-12-03 峨眉山天梁星制药有限公司 High performance liquid chromatography of 3-tert-butyl dimethyl silica glutaric anhydride
CN111548312A (en) * 2020-06-01 2020-08-18 雅本化学股份有限公司 Rosuvastatin calcium tablet and preparation process thereof
CN113754590B (en) * 2021-09-06 2023-06-13 浙江乐普药业股份有限公司 Preparation method of rosuvastatin calcium intermediate

Citations (6)

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Publication number Priority date Publication date Assignee Title
US2698326A (en) * 1954-12-28 S-aminomethylpyrimtoines
EP0521471A1 (en) * 1991-07-01 1993-01-07 Shionogi Seiyaku Kabushiki Kaisha Pyrimidine derivatives as HMG-CoA reductase inhibitors
JPH07118233A (en) * 1993-10-19 1995-05-09 Shionogi & Co Ltd Process for producing pyrimidine derivative
EP1035127A1 (en) * 1999-03-10 2000-09-13 Lonza AG Process for the preparation of N-[5-(Diphenylphosphinoylmethyl)-4-(4-fluorphenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethansulfonamide
WO2001060804A1 (en) * 2000-02-15 2001-08-23 Astrazeneca Ab Crystalline salts of 7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3r,5s)-3,5-dihydroxyhept-6-enoic acid
WO2003016317A1 (en) * 2001-08-16 2003-02-27 Teva Pharmaceutical Industries Ltd. Processes for preparing calcium salt forms of statins

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Patent Citations (6)

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Publication number Priority date Publication date Assignee Title
US2698326A (en) * 1954-12-28 S-aminomethylpyrimtoines
EP0521471A1 (en) * 1991-07-01 1993-01-07 Shionogi Seiyaku Kabushiki Kaisha Pyrimidine derivatives as HMG-CoA reductase inhibitors
JPH07118233A (en) * 1993-10-19 1995-05-09 Shionogi & Co Ltd Process for producing pyrimidine derivative
EP1035127A1 (en) * 1999-03-10 2000-09-13 Lonza AG Process for the preparation of N-[5-(Diphenylphosphinoylmethyl)-4-(4-fluorphenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethansulfonamide
WO2001060804A1 (en) * 2000-02-15 2001-08-23 Astrazeneca Ab Crystalline salts of 7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3r,5s)-3,5-dihydroxyhept-6-enoic acid
WO2003016317A1 (en) * 2001-08-16 2003-02-27 Teva Pharmaceutical Industries Ltd. Processes for preparing calcium salt forms of statins

Non-Patent Citations (2)

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Title
GRAUL, A. ET AL: "ZD-4522. Hypolipidemic HMG-CoA reductase inhibitor", DRUGS OF THE FUTURE (1999), 24(5), 511-513, XP000882032 *
WATANABE, MASAMICHI ET AL: "Synthesis and biological activity of methanesulfonamide pyrimidine- and N-methanesulfonyl pyrrole-substituted 3,5-dihydroxy-6-heptenoates, a nove series of HMG-CoA reductase inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY (1997), 5(2), 437-444, XP000911018 *

Also Published As

Publication number Publication date
AR039836A1 (en) 2005-03-02
WO2003097614A2 (en) 2003-11-27
EA200401533A1 (en) 2005-06-30
BR0311195A (en) 2005-02-22
AU2003228010A1 (en) 2003-12-02
EP1585736A2 (en) 2005-10-19
US20050222415A1 (en) 2005-10-06

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