CN102498098A - 作为群多普利中间体的(2S，3aR，7aS)-八氢-1H-吲哚羧酸的合成方法 - Google Patents

作为群多普利中间体的(2S，3aR，7aS)-八氢-1H-吲哚羧酸的合成方法 Download PDF

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Publication number
CN102498098A
CN102498098A CN2010800413803A CN201080041380A CN102498098A CN 102498098 A CN102498098 A CN 102498098A CN 2010800413803 A CN2010800413803 A CN 2010800413803A CN 201080041380 A CN201080041380 A CN 201080041380A CN 102498098 A CN102498098 A CN 102498098A
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China
Prior art keywords
compound
ethyl
octahydro
temperature
indole
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CN2010800413803A
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English (en)
Chinese (zh)
Inventor
桑贾伊·R·谢姆布鲁卡
拉贾拉托纳·E·雷迪
道格拉斯·M·雷梅尔
约翰·T·帕夫莉娜
斯蒂芬·S·乌拉雷伊
布莱恩·J·科特克
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Abbott Laboratories
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Abbott Laboratories
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Publication of CN102498098A publication Critical patent/CN102498098A/zh
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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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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Heart & Thoracic Surgery (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)
CN2010800413803A 2009-07-16 2010-07-16 作为群多普利中间体的(2S，3aR，7aS)-八氢-1H-吲哚羧酸的合成方法 Pending CN102498098A (zh)

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 (1)

Publication Number Publication Date
CN102498098A true CN102498098A (zh) 2012-06-13

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CN2010800413803A Pending CN102498098A (zh) 2009-07-16 2010-07-16 作为群多普利中间体的(2S，3aR，7aS)-八氢-1H-吲哚羧酸的合成方法

Country Status (10)

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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)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111620788A (zh) * 2020-04-20 2020-09-04 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 (2)

* 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
CN101423490A (zh) * 2008-06-16 2009-05-06 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

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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
IE55867B1 (en) * 1981-12-29 1991-02-14 Hoechst Ag New derivatives of bicyclic aminoacids,processes for their preparation,agents containing these compounds and their use,and new bicyclic aminoacids as intermediates and processes for their preparation
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
JPWO2004065368A1 (ja) 2003-01-21 2006-05-18 大原薬品工業株式会社 トランドラプリル合成中間体の製造方法
ATE283257T1 (de) * 2003-04-15 2004-12-15 Servier Lab Verfahren zur synthese von (2s,3as,7as)- perhydroindol-2-carbonsäure und seiner 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
JP2007512260A (ja) 2003-11-28 2007-05-17 アツァト・ファーマシューティカルズ・イングリーディエンツ・アーゲー ｛Ｎ−［１−（Ｓ）−カルボアルコキシ−３−フェニルプロピル］−Ｓ−アラニル−２Ｓ，３ａＲ，７ａＳ−オクタヒドロインドール−２−カルボン酸｝化合物類の製造方法
WO2006014916A2 (en) 2004-07-26 2006-02-09 Dr. Reddy's Laboratories Ltd. Preparation of trandolapril
WO2006085332A1 (en) 2005-02-14 2006-08-17 Lupin Limited Improved process for preparation of highly pure trandolapril
EP1724260B1 (en) 2005-05-06 2008-02-20 Sochinaz SA Process for the synthesis of (2S, 3aR, 7aS)octahydroindole-2-carboxylic acid and its conversion to trandolapril
CA2614099A1 (en) 2005-07-05 2007-01-11 Cipla Limited Process for the synthesis of the ace inhibitor
CN101808990B (zh) 2007-07-24 2012-09-05 百时美施贵宝公司 作为趋化因子受体活性调节剂的哌啶衍生物

Patent Citations (2)

* 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
CN101423490A (zh) * 2008-06-16 2009-05-06 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

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
F. BRION，等: "Stereoselective Synthesis of a trans-Octahydroindole Derivative，Precursor of Trandolapril (RU 44 570), an Inhibitor of Angiotensin Converting Enzyme", 《TETRAHEDRON LETTERS》, vol. 33, no. 34, 1 January 1992 (1992-01-01), XP002320609, DOI: doi:10.1016/S0040-4039(00)61225-X *
YUJIRO HAYASHI, 等: "A Novel Chiral Super-Lewis Acidic Catalyst for Enantioselective Synthesis", 《J.AM.CHEM.SOC.》, vol. 118, no. 23, 31 December 1996 (1996-12-31) *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111620788A (zh) * 2020-04-20 2020-09-04 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
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

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Publication number Publication date
IN2012DN00453A (enExample) 2015-05-15
CA2768239A1 (en) 2011-01-20
AU2010273259A1 (en) 2012-02-09
CO6491043A2 (es) 2012-07-31
JP2012533563A (ja) 2012-12-27
US20110065930A1 (en) 2011-03-17
AU2010273259B2 (en) 2013-03-07
US8288565B2 (en) 2012-10-16
EP2454235A1 (en) 2012-05-23
RU2012103753A (ru) 2013-08-27
WO2011009021A1 (en) 2011-01-20

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