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

Info

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
Authority
CN
China
Prior art keywords
compound
ethyl
octahydro
temperature
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.)
Pending
Application number
CN2010800413803A
Other languages
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
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.)
Abbott Laboratories
Original Assignee
Abbott Laboratories
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 Abbott Laboratories filed Critical Abbott Laboratories
Publication of CN102498098A publication Critical patent/CN102498098A/zh
Pending legal-status Critical Current

Links

Images

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (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

Family

ID=42585097

Family Applications (1)

Application Number Title Priority Date Filing Date
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)

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)

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

Family Cites Families (16)

* 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
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
ES2233913T3 (es) * 2003-04-15 2005-06-16 Les Laboratoires Servier Nuevo procedimiento de sintesis del acido (2s,3as,7as) perhidroindol-2-carboxilico y de sus esteres, y aplicacion as la sintesis de perindopril.
SI21507A (sl) 2003-05-16 2004-12-31 LEK farmacevtska dru�ba d.d. Postopek za pripravo spojin z ace inhibitornim delovanjem
EP1689711A1 (de) 2003-11-28 2006-08-16 Azad Pharmaceutical Ingredients AG Verfahren zur herstellung von n- 1-(s)-carbalkoxy-3-ph enylpropyl -s-alanyl-2s, 3ar, 7as-octahydroindol-2-carbonsäure;verbindungen
WO2006014916A2 (en) 2004-07-26 2006-02-09 Dr. Reddy's Laboratories Ltd. Preparation of trandolapril
AU2005327440A1 (en) 2005-02-14 2006-08-17 Lupin Limited Improved process for preparation of highly pure trandolapril
ATE386718T1 (de) 2005-05-06 2008-03-15 Sochinaz Sa Verfahren zur herstellung von (2s, 3ar, 7as)- octahydroindole-2-carbonsäure und umwandlung zum trandolapril
JP2008545006A (ja) * 2005-07-05 2008-12-11 シプラ・リミテッド Ａｃｅ阻害剤の合成方法
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

Also Published As

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

Similar Documents

Publication Publication Date Title
KR101064413B1 (ko) 이바브라딘 및 이의 약제학적으로 허용되는 산과의 부가염의 합성 방법
CN102834370B (zh) 1-氨基-1-烷氧基羰基-2-乙烯基环丙烷的制备方法
US9938239B2 (en) Method for preparing silodosin
CN103282350B (zh) 制备雷米普利的方法
CN103044418B (zh) (s,s)-2,8-二氮杂双环[4,3,0]壬烷的不对称合成方法、相关原料及制备方法
CN1094927C (zh) 2－氮杂二羟基二环[2.2.1]庚烷化合物的制备方法以及该化合物的l－酒石酸盐
CN102498098A (zh) 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
JP2010090031A (ja) 二環性プロリン化合物の製造方法
CN103619815A (zh) 脯氨酸化合物的制造方法
JP2009172474A (ja) ディールス・アルダー反応触媒及び不斉環化付加生成物の製造方法
CN117736104A (zh) 一种可见光催化合成丁二羧酸酯衍生物的方法
HK1172025A (en) Processes for the synthesis of (2s, 3ar, 7as)-octahydro-1h-indole carboxylic acid as an intermediate for trandolapril
WO2005113500A1 (en) Process for the preparation of perindopril and salts thereof
WO2007085933A2 (en) Process for the preparation of n-[1-(s)-ethoxycarbonyl-1-butyl]-(s)-alanine-dmt complex and its use in the preparation of perindopril
JP3204368B2 (ja) 光学活性アミド類の製法
CN103906739B (zh) 用于制备hcv的大环蛋白酶抑制剂的方法和中间体
CN1185782A (zh) 2－氮杂双环[2,2,1]庚烷的新衍生物,其制备和应用
US20080242861A1 (en) Synthesis of amino-protected cyclohexane-1,4-diyldimethanamine and its derivatives
WO2007062865A1 (en) Process for the preparation of perindopril and salts thereof
JP2004210660A (ja) （２Ｓ，３ａＲ，７ａＳ）−１−［（Ｓ）−Ｎ−［（Ｓ）−１−エトキシカルボニル−３−フェニルプロピル］アラニル］ヘキサヒドロ−２−インドリンカルボン酸ベンジルエステルの製造方法
HK1051189A (en) Process for preparing 2-azadihydroxybicyclo[2.2.1]heptane compounds and the l-tartaric acid salt of the compound
HK1022475B (en) Process for preparing 2-azadihydroxybicyclo (2.2.1)heptane compounds and the l-tartaric acid salt of the compound
HK1039131A1 (en) Derivatives of octahydro-6,10-dioxo-6h-pyridazino(1,2-a)(1,2)diazepine-1-carboxylic acid, the preparation process and the use thereof
HK1096408A1 (en) Novel method for the synthesis of perindopril and the pharmaceutically-acceptable salts thereof
HK1039131B (en) Derivatives of octahydro-6,10-dioxo-6h-pyridazino(1,2-a)(1,2)diazepine-1-carboxylic acid, the preparation process and the use thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
REG Reference to a national code

Ref country code: HK

Ref legal event code: DE

Ref document number: 1172025

Country of ref document: HK

AD01 Patent right deemed abandoned

Effective date of abandoning: 20120613

C20 Patent right or utility model deemed to be abandoned or is abandoned
REG Reference to a national code

Ref country code: HK

Ref legal event code: WD

Ref document number: 1172025

Country of ref document: HK