CA2450820C - Processes for preparing calcium salt forms of statins - Google Patents

Processes for preparing calcium salt forms of statins Download PDF

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Publication number
CA2450820C
CA2450820C CA2450820A CA2450820A CA2450820C CA 2450820 C CA2450820 C CA 2450820C CA 2450820 A CA2450820 A CA 2450820A CA 2450820 A CA2450820 A CA 2450820A CA 2450820 C CA2450820 C CA 2450820C
Authority
CA
Canada
Prior art keywords
statin
calcium
atorvastatin
mixture
ester derivative
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
CA2450820A
Other languages
English (en)
French (fr)
Other versions
CA2450820A1 (en
Inventor
Valerie Niddam-Hildesheim
Revital Lifshitz-Liron
Rami Lidor-Hadas
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.)
Teva Pharmaceutical Industries Ltd
Original Assignee
Teva Pharmaceutical Industries 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
Priority claimed from US10/037,412 external-priority patent/US6528661B2/en
Application filed by Teva Pharmaceutical Industries Ltd filed Critical Teva Pharmaceutical Industries Ltd
Publication of CA2450820A1 publication Critical patent/CA2450820A1/en
Application granted granted Critical
Publication of CA2450820C publication Critical patent/CA2450820C/en
Anticipated expiration legal-status Critical
Expired - Fee Related 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
    • 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)
  • Urology & Nephrology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyrane Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyridine Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Indole Compounds (AREA)
  • Quinoline Compounds (AREA)
CA2450820A 2001-08-16 2002-08-16 Processes for preparing calcium salt forms of statins Expired - Fee Related CA2450820C (en)

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 (en) 2001-08-16 2002-08-16 Processes for preparing calcium salt forms of statins

Publications (2)

Publication Number Publication Date
CA2450820A1 CA2450820A1 (en) 2003-02-27
CA2450820C true CA2450820C (en) 2011-03-15

Family

ID=26714105

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2450820A Expired - Fee Related CA2450820C (en) 2001-08-16 2002-08-16 Processes for preparing calcium salt forms of statins

Country Status (17)

Country Link
EP (1) EP1425287A4 (ja)
JP (2) JP4188826B2 (ja)
CN (1) CN100430405C (ja)
AU (1) AU2002324715B2 (ja)
CA (1) CA2450820C (ja)
CZ (1) CZ2004337A3 (ja)
HR (1) HRPK20040255B3 (ja)
HU (1) HUP0500616A3 (ja)
IL (2) IL160077A0 (ja)
IS (1) IS7148A (ja)
MX (1) MXPA04001451A (ja)
NO (1) NO20041082L (ja)
NZ (1) NZ529913A (ja)
PL (1) PL370407A1 (ja)
SK (1) SK1402004A3 (ja)
TR (1) TR200302281T2 (ja)
WO (1) WO2003016317A1 (ja)

Families Citing this family (55)

* Cited by examiner, † Cited by third party
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US7411075B1 (en) 2000-11-16 2008-08-12 Teva Pharmaceutical Industries Ltd. Polymorphic form of atorvastatin calcium
DE60136095D1 (de) * 2000-11-16 2008-11-20 Teva Pharma Hydrolyse von är(r*,r*)ü-2-(4-fluorphenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-ä(phenylamino)carbonylü-1h-pyrrol-heptansäureestern mit calciumhydroxid
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
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
WO2002057229A1 (en) 2001-01-19 2002-07-25 Biocon India Limited FORM V CRYSTALLINE [R-(R*,R*)]-2-(4-FLUOROPHENYL)-ß,$G(D)-DIHYDROXY-5-(1-METHYLETHYL)-3-PHENYL-4-[(PHENYLAMINO)CARBONYL]-1H-PYRROLE-1- HEPTANOIC ACID HEMI CALCIUM SALT. (ATORVASTATIN)
US7361772B2 (en) 2001-08-16 2008-04-22 Biocon Limited Process for the production of atorvastatin calcium
CA2412012C (en) 2001-11-20 2011-08-02 Ed. Geistlich Soehne Ag Fuer Chemische Industrie Resorbable extracellular matrix containing collagen i and collagen ii for reconstruction of cartilage
HUP0500074A3 (en) 2002-03-18 2005-07-28 Biocon Ltd Bangalore Amorphous hmg-coa reductase inhibitors of desired particle size and process for producing them
AU2003228010A1 (en) * 2002-05-21 2003-12-02 Ranbaxy Laboratories Limited Process for the preparation of rosuvastatin
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
DE202004021379U1 (de) * 2003-02-12 2008-02-21 Ciba Specialty Chemicals Holding Inc. Kristalline Formen von Pitivastatin Calcium
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
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EP1816126A1 (en) * 2003-08-28 2007-08-08 Teva Pharmaceutical Industries Limited Process for preparation of rosuvastatin calcium
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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
EP1737828A1 (en) * 2004-01-19 2007-01-03 Ranbaxy Laboratories Limited Amorphous magnesium salts of rosuvastatin
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JP4713574B2 (ja) 2005-02-22 2011-06-29 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 ロスバスタチンアルキルエーテルを含まないロスバスタチンおよびその塩およびそれらを製造する方法
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
MX2008001597A (es) * 2005-08-04 2008-04-04 Transform Pharmaceuticals Inc Formulaciones novedosas que comprenden fenofibrato y una estatina y metodos relacionados de tratamiento.
EP1805148A2 (en) 2005-08-16 2007-07-11 Teva Pharmaceutical Industries Ltd. Crystalline rosuvastatin intermediate
CN100371709C (zh) * 2005-12-12 2008-02-27 重庆医药工业研究院有限责任公司 一种用液相色谱法分离测定匹伐他汀及其光学异构体的方法
WO2007125547A2 (en) * 2006-05-03 2007-11-08 Manne Satyanarayana Reddy 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
EP2022784A1 (en) 2007-08-08 2009-02-11 LEK Pharmaceuticals D.D. Process for the preparation of methyl ester of rosuvastatin
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
WO2011086584A2 (en) 2010-01-18 2011-07-21 Msn Laboratories Limited Improved process for the preparation of amide intermediates and their use thereof
HUP1000299A2 (hu) 2010-06-08 2012-02-28 Nanoform Cardiovascular Therapeutics Ltd Nanostrukturált Atorvastatint, gyógyszerészetileg elfogadott sóit és kokristályait tartalmazó készítmény és eljárás elõállításukra
EP3178812A1 (en) * 2010-11-12 2017-06-14 Hetero Research Foundation Novel polymorphs of pitavastatin calcium
HU229260B1 (en) * 2010-11-29 2013-10-28 Egis Gyogyszergyar Nyrt Process for preparation of rosuvastatin salts
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
WO2015119261A1 (ja) 2014-02-06 2015-08-13 株式会社エーピーアイ コーポレーション ロスバスタチンカルシウム及びその中間体の製造方法
KR20160126700A (ko) 2015-04-24 2016-11-02 미래파인켐 주식회사 스타틴의 중간체, 이의 제조방법 및 이를 이용한 로수바스타틴의 제조방법
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
CN105111173B (zh) * 2015-06-26 2017-06-23 上海应用技术学院 他汀含氟衍生物及其用途
CN107949556B (zh) 2015-08-05 2021-12-07 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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Also Published As

Publication number Publication date
IS7148A (is) 2004-02-11
NO20041082L (no) 2004-03-15
JP4188826B2 (ja) 2008-12-03
HUP0500616A3 (en) 2011-07-28
IL160077A0 (en) 2004-06-20
JP2005500382A (ja) 2005-01-06
TR200302281T2 (tr) 2004-09-21
CN1543468A (zh) 2004-11-03
IL160077A (en) 2007-10-31
PL370407A1 (en) 2005-05-30
HRP20040255A2 (en) 2004-08-31
WO2003016317A1 (en) 2003-02-27
EP1425287A1 (en) 2004-06-09
CZ2004337A3 (cs) 2005-01-12
EP1425287A4 (en) 2005-09-07
NZ529913A (en) 2005-03-24
CN100430405C (zh) 2008-11-05
HRPK20040255B3 (en) 2006-02-28
HUP0500616A2 (hu) 2005-11-28
JP2009024008A (ja) 2009-02-05
MXPA04001451A (es) 2005-02-17
CA2450820A1 (en) 2003-02-27
SK1402004A3 (sk) 2005-01-03
AU2002324715B2 (en) 2009-03-12

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