CA2472776C - Process for the manufacture of hmg-coa reductase inhibitors - Google Patents

Process for the manufacture of hmg-coa reductase inhibitors Download PDF

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Publication number
CA2472776C
CA2472776C CA2472776A CA2472776A CA2472776C CA 2472776 C CA2472776 C CA 2472776C CA 2472776 A CA2472776 A CA 2472776A CA 2472776 A CA2472776 A CA 2472776A CA 2472776 C CA2472776 C CA 2472776C
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CA
Canada
Prior art keywords
formula
iii
compound
hydroxy
degree
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.)
Expired - Fee Related
Application number
CA2472776A
Other languages
English (en)
French (fr)
Other versions
CA2472776A1 (en
Inventor
Murat Acemoglu
Bernhard Riss
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.)
Individual
Original Assignee
Novartis AG
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 Novartis AG filed Critical Novartis AG
Publication of CA2472776A1 publication Critical patent/CA2472776A1/en
Application granted granted Critical
Publication of CA2472776C publication Critical patent/CA2472776C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • 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
    • 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
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (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)
  • Vascular Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (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)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Quinoline Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2472776A 2002-01-31 2003-01-30 Process for the manufacture of hmg-coa reductase inhibitors Expired - Fee Related CA2472776C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US35378702P 2002-01-31 2002-01-31
US60/353,787 2002-01-31
PCT/EP2003/000954 WO2003064392A1 (en) 2002-01-31 2003-01-30 Process for the manufacture of hmg-coa reductase inhibitors

Publications (2)

Publication Number Publication Date
CA2472776A1 CA2472776A1 (en) 2003-08-07
CA2472776C true CA2472776C (en) 2011-01-25

Family

ID=27663254

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2472776A Expired - Fee Related CA2472776C (en) 2002-01-31 2003-01-30 Process for the manufacture of hmg-coa reductase inhibitors

Country Status (22)

Country Link
US (2) US7371865B2 (https=)
EP (1) EP1472228B1 (https=)
JP (1) JP4524111B2 (https=)
KR (1) KR20040081161A (https=)
CN (1) CN1305853C (https=)
AT (1) ATE426594T1 (https=)
AU (1) AU2003226971B2 (https=)
BR (1) BR0307303A (https=)
CA (1) CA2472776C (https=)
CO (1) CO5601005A2 (https=)
DE (1) DE60326819D1 (https=)
EC (1) ECSP045214A (https=)
ES (1) ES2323267T3 (https=)
IL (1) IL162980A (https=)
MX (1) MXPA04007396A (https=)
NO (1) NO327091B1 (https=)
NZ (1) NZ534232A (https=)
PL (1) PL370658A1 (https=)
PT (1) PT1472228E (https=)
RU (1) RU2299196C2 (https=)
WO (1) WO2003064392A1 (https=)
ZA (1) ZA200405322B (https=)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101219992B (zh) * 2003-02-12 2011-08-31 日产化学工业株式会社 匹伐他汀钙的晶形
JPWO2004094385A1 (ja) * 2003-04-24 2006-07-13 ダイセル化学工業株式会社 （３ｒ，５ｓ，６ｅ）−７−［２−シクロプロピル−４−（４−フルオロフェニル）キノリン−３−イル］−３，５−ジヒドロキシ−６−ヘプテン酸エチルの製造方法
TWI328006B (en) * 2003-12-26 2010-08-01 Nissan Chemical Ind Ltd Crystal form of quinoline compound and process for its production
EP1817027A2 (en) * 2004-09-27 2007-08-15 Ranbaxy Laboratories Limited Process for preparating enantiomerically pure fluvastatin sodium and a novel polymorphic form thereof
EP2024341B1 (en) * 2006-05-03 2015-12-02 MSN Laboratories Private Limited Novel 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
EP2062903A1 (en) 2007-04-18 2009-05-27 Teva Pharmaceutical Industries Ltd. Statin intermediates and process for the preparation of statins
JP2010501643A (ja) * 2007-07-12 2010-01-21 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 薄膜蒸発及び化学的手法によるロスバスタチン中間体の精製
WO2010089770A2 (en) * 2009-01-19 2010-08-12 Msn Laboratories Limited Improved process for the preparation of highly pure (3r,5s)-7-[2-cyclopropyl-4-(4-fluorophenyl) quinolin-3-yl]-3,5-dihydroxy-6(e)-heptenoic acid and pharmaceutically acceptable salts thereof
KR101160152B1 (ko) * 2009-02-24 2012-06-27 한미사이언스 주식회사 스타틴 화합물 또는 그 염의 신규 제조방법, 및 이에 사용되는 중간체 화합물
US8987444B2 (en) 2010-01-18 2015-03-24 Msn Laboratories Private Limited Process for the preparation of amide intermediates and their use thereof
WO2011104725A2 (en) * 2010-02-23 2011-09-01 Cadila Healthcare Limited Hmg-coa reductase inhibitors and process for the preparation thereof
EP2383260A3 (en) 2010-04-30 2011-12-28 Dipharma Francis S.r.l. Process for the preparation of statins
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
JP5822169B2 (ja) * 2010-07-01 2015-11-24 ユーハン・コーポレイションＹＵＨＡＮ Ｃｏｒｐｏｒａｔｉｏｎ ＨＭＧ−ＣｏＡ還元酵素阻害剤及びその中間体の製造方法
EP3178812A1 (en) * 2010-11-12 2017-06-14 Hetero Research Foundation Novel polymorphs of pitavastatin calcium
AU2012345473B2 (en) 2011-11-28 2017-05-25 Mylan Laboratories Ltd Process for producing chiral statin side chain intermediates employing candida|antarctica lipase B
CN103288871A (zh) * 2012-02-28 2013-09-11 浙江京新药业股份有限公司 一种制备二羟基酸HMG-CoA还原酶抑制剂用的中间体及其制备方法和应用
ITVI20130039A1 (it) * 2013-02-20 2014-08-21 F I S Fabbrica Italiana Sint I S P A Processo per la preparazione di intermedi chiave per la sintesi di statine
CN103172656B (zh) * 2013-04-02 2015-07-08 浙江科技学院 3-二甲基叔丁基硅氧基戊二酸酐的合成工艺
CN111518035A (zh) * 2020-06-18 2020-08-11 安徽鼎旺医药有限公司 一种瑞舒伐他汀叔丁胺盐及其制备方法
CN113683539B (zh) * 2021-09-23 2023-05-16 上海裕兰生物科技有限公司 一种聚酮中间体的合成方法

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5354772A (en) * 1982-11-22 1994-10-11 Sandoz Pharm. Corp. Indole analogs of mevalonolactone and derivatives thereof
US4650890A (en) * 1984-04-03 1987-03-17 Sandoz Corp. Preparation of olefinic compounds and intermediates thereof
CA1336714C (en) 1987-08-20 1995-08-15 Yoshihiro Fujikawa Quinoline type mevalonolactone inhibitors of cholesterol biosynthesis
JP2569746B2 (ja) * 1987-08-20 1997-01-08 日産化学工業株式会社 キノリン系メバロノラクトン類
US4804770A (en) * 1988-04-29 1989-02-14 E. R. Squibb & Sons, Inc. Process for preparing a keto-phosphonate intermediate useful in preparing HMG-CoA reductase inhibitors
DE3911064A1 (de) * 1989-04-06 1990-10-11 Bayer Ag Substituierte 1,8-naphthyridine
US5049577A (en) * 1990-01-29 1991-09-17 E. R. Squibb & Sons, Inc. 2-pyrrolidone substituted dihydroxy alkanoic, alkenoic and alkynoic acids, compositions and HMG-CoA reductase inhibition therewith
ATE123020T1 (de) * 1990-05-11 1995-06-15 American Cyanamid Co N-acylierte arylpyrrole als insektizide, akarizide, nematizide und molluskizide wirkstoffe.
JP3528186B2 (ja) 1991-06-24 2004-05-17 日産化学工業株式会社 光学活性キノリンメバロン酸のジアステレオマー塩
PL362981A1 (en) * 2000-11-16 2004-11-02 Teva Pharmaceutical Industries Ltd. 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
EP1365029A4 (en) * 2001-02-02 2009-07-29 Mitsubishi Chem Corp "PROCESS FOR PREPARING (3R, 5S) - (E) -7-2-CYCLOPROPYL-4- (4-FLUORPHENYL) CHINOLINE-3-YL-3,5-DIHYDROXY-HEPT-6-ACID ESTERS"
KR100919941B1 (ko) * 2001-11-14 2009-10-05 닛산 가가쿠 고교 가부시키 가이샤 광학활성 옥소헵텐산 에스테르의 제조방법
US6835838B2 (en) * 2002-01-28 2004-12-28 Novartis Ag Process for the manufacture of organic compounds
GB0210234D0 (en) * 2002-05-03 2002-06-12 Novartis Ag Process for the manufacture of organic compounds

Also Published As

Publication number Publication date
ECSP045214A (es) 2004-09-28
HK1070651A1 (en) 2005-06-24
WO2003064392A1 (en) 2003-08-07
JP2005520814A (ja) 2005-07-14
NO20043611L (no) 2004-08-30
AU2003226971B2 (en) 2006-11-30
ES2323267T3 (es) 2009-07-10
EP1472228A1 (en) 2004-11-03
US7371865B2 (en) 2008-05-13
EP1472228B1 (en) 2009-03-25
KR20040081161A (ko) 2004-09-20
CN1305853C (zh) 2007-03-21
ATE426594T1 (de) 2009-04-15
NO327091B1 (no) 2009-04-20
DE60326819D1 (de) 2009-05-07
BR0307303A (pt) 2005-01-11
IL162980A (en) 2010-02-17
RU2299196C2 (ru) 2007-05-20
NZ534232A (en) 2006-03-31
CN1622937A (zh) 2005-06-01
MXPA04007396A (es) 2004-10-11
ZA200405322B (en) 2005-07-27
RU2004126442A (ru) 2005-06-10
CA2472776A1 (en) 2003-08-07
US20050070605A1 (en) 2005-03-31
JP4524111B2 (ja) 2010-08-11
PL370658A1 (en) 2005-05-30
PT1472228E (pt) 2009-06-24
US20080182873A1 (en) 2008-07-31
CO5601005A2 (es) 2006-01-31

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Effective date: 20200130