AU2010273259B2 - Processes for the synthesis of (2S, 3aR, 7aS)-octahydro-1H-indole carboxylic acid as an intermediate for trandolapril - Google Patents

Processes for the synthesis of (2S, 3aR, 7aS)-octahydro-1H-indole carboxylic acid as an intermediate for trandolapril Download PDF

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Publication number
AU2010273259B2
AU2010273259B2 AU2010273259A AU2010273259A AU2010273259B2 AU 2010273259 B2 AU2010273259 B2 AU 2010273259B2 AU 2010273259 A AU2010273259 A AU 2010273259A AU 2010273259 A AU2010273259 A AU 2010273259A AU 2010273259 B2 AU2010273259 B2 AU 2010273259B2
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AU
Australia
Prior art keywords
ethyl
compound
octahydro
acid
indole
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
AU2010273259A
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English (en)
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AU2010273259A1 (en
Inventor
Sanjay R. Chemburkar
Brian J. Kotecki
John T. Pavlina
Douglas M. Reamer
Rajarathman E. Reddy
Stephen S. Ulrey
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Abbott Laboratories
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Abbott Laboratories
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Publication of AU2010273259A1 publication Critical patent/AU2010273259A1/en
Application granted granted Critical
Publication of AU2010273259B2 publication Critical patent/AU2010273259B2/en
Ceased legal-status Critical Current
Anticipated expiration legal-status Critical

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    • 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
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
AU2010273259A 2009-07-16 2010-07-16 Processes for the synthesis of (2S, 3aR, 7aS)-octahydro-1H-indole carboxylic acid as an intermediate for trandolapril Ceased AU2010273259B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US22603009P 2009-07-16 2009-07-16
US61/226,030 2009-07-16
PCT/US2010/042219 WO2011009021A1 (en) 2009-07-16 2010-07-16 Processes for the synthesis of (2s, 3ar, 7as)-octahydro-1h-indole carboxylic acid as an intermediate for trandolapril

Publications (2)

Publication Number Publication Date
AU2010273259A1 AU2010273259A1 (en) 2012-02-09
AU2010273259B2 true AU2010273259B2 (en) 2013-03-07

Family

ID=42585097

Family Applications (1)

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AU2010273259A Ceased AU2010273259B2 (en) 2009-07-16 2010-07-16 Processes for the synthesis of (2S, 3aR, 7aS)-octahydro-1H-indole carboxylic acid as an intermediate for trandolapril

Country Status (10)

Country Link
US (1) US8288565B2 (enExample)
EP (1) EP2454235A1 (enExample)
JP (1) JP2012533563A (enExample)
CN (1) CN102498098A (enExample)
AU (1) AU2010273259B2 (enExample)
CA (1) CA2768239A1 (enExample)
CO (1) CO6491043A2 (enExample)
IN (1) IN2012DN00453A (enExample)
RU (1) RU2012103753A (enExample)
WO (1) WO2011009021A1 (enExample)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111620788B (zh) * 2020-04-20 2022-09-30 广东莱佛士制药技术有限公司 一种制备(2s,3s)-3-氨基-二环[2.2.2]辛烷-2-甲酸酯的方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005054194A1 (en) * 2003-11-25 2005-06-16 Texcontor Etablissement A method for the preparation of (2s, 3ar, 7as)-octahydro-1h-indole-2-carboxylic acid as key intermediate in the preparation of trandolapril by reacting a cyclohexyl aziridine with a dialkyl malonate

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US487932A (en) 1892-12-13 George b
US4350704A (en) 1980-10-06 1982-09-21 Warner-Lambert Company Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids
NZ202903A (en) * 1981-12-29 1988-01-08 Hoechst Ag 1-- pe pyrrol-2-yl-carboxylic acid derivatives and pharmaceutical compositions
US4490386A (en) 1982-09-23 1984-12-25 Warner-Lambert Company Phosphate salts of 1-[2-[(1-alkoxycarbonyl-3-aralkyl)-amino]-1-oxoalkyl]octahydro-1H-indole-2-carboxylic acids, preparation of, and medical compositions thereof
US4556655A (en) 1984-09-24 1985-12-03 Schering Corporation Antihypertensive compounds having both diuretic and angiotensin converting enzyme inhibitory activity
FR2605630B1 (fr) 1986-10-22 1989-06-30 Roussel Uclaf Procede de preparation de derives de l'octahydroindole et intermediaires de preparation
DE19900205A1 (de) 1999-01-07 2000-07-13 Basf Ag Verfahren zur Herstellung von (2S,4R,9S)-Octahydro-1H-indol-2-carbonsäure und Zwischenprodukte dafür
WO2004065368A1 (ja) 2003-01-21 2004-08-05 Ohara Chemical Industries, Ltd. トランドラプリル合成中間体の製造方法
DE60300166T2 (de) * 2003-04-15 2005-12-01 Les Laboratoires Servier Verfahren zur Synthese von (2S, 3aS, 7aS)-Perhydroindol-2-carbonsäure und seinen Estern, und Verwendung in der Synthese von Perindopril
SI21507A (sl) 2003-05-16 2004-12-31 LEK farmacevtska dru�ba d.d. Postopek za pripravo spojin z ace inhibitornim delovanjem
US20070135513A1 (en) 2003-11-28 2007-06-14 Mirko Pogutter Method for producing {n-[1-(s)-carbalkoxy-3-phenylpropyl]-s-alanyl-2s, 3ar, 7as-octahydroindole-2-carboxylic acid} compounds
WO2006014916A2 (en) 2004-07-26 2006-02-09 Dr. Reddy's Laboratories Ltd. Preparation of trandolapril
US20080171885A1 (en) 2005-02-14 2008-07-17 Lupin Limited Process for Preparation of Highly Pure Trandolapril
DE602005004897D1 (de) 2005-05-06 2008-04-03 Sochinaz Sa Verfahren zur Herstellung von i(2S, 3aR, 7aS)-octahydroindole-2-Carbonsäure und Umwandlung zum Trandolapril
WO2007003947A2 (en) 2005-07-05 2007-01-11 Cipla Limited Process for the synthesis of the ace inhibitor trandolapril
JP5292400B2 (ja) 2007-07-24 2013-09-18 ブリストル−マイヤーズ スクイブ カンパニー ケモカイン受容体活性のモジュレーターとしてのピペリジン誘導体
CN101423490B (zh) * 2008-06-16 2012-07-18 重庆南松医药科技股份有限公司 群多普利关键中间体（2S,3aR,7as）-八氢－1H－吲哚－2－羧酸的合成方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005054194A1 (en) * 2003-11-25 2005-06-16 Texcontor Etablissement A method for the preparation of (2s, 3ar, 7as)-octahydro-1h-indole-2-carboxylic acid as key intermediate in the preparation of trandolapril by reacting a cyclohexyl aziridine with a dialkyl malonate

Also Published As

Publication number Publication date
WO2011009021A1 (en) 2011-01-20
AU2010273259A1 (en) 2012-02-09
CN102498098A (zh) 2012-06-13
RU2012103753A (ru) 2013-08-27
CA2768239A1 (en) 2011-01-20
US8288565B2 (en) 2012-10-16
EP2454235A1 (en) 2012-05-23
CO6491043A2 (es) 2012-07-31
IN2012DN00453A (enExample) 2015-05-15
US20110065930A1 (en) 2011-03-17
JP2012533563A (ja) 2012-12-27

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