WO2005121084A1 - A method of preparation of ramipril - Google Patents

A method of preparation of ramipril Download PDF

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Publication number
WO2005121084A1
WO2005121084A1 PCT/CZ2005/000048 CZ2005000048W WO2005121084A1 WO 2005121084 A1 WO2005121084 A1 WO 2005121084A1 CZ 2005000048 W CZ2005000048 W CZ 2005000048W WO 2005121084 A1 WO2005121084 A1 WO 2005121084A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
ramipril
benzyl ester
solution
toluene
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
PCT/CZ2005/000048
Other languages
English (en)
French (fr)
Inventor
Hana Stepankova
Pavel Pihera
Josef Hajicek
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.)
Zentiva KS
Original Assignee
Zentiva KS
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 Zentiva KS filed Critical Zentiva KS
Publication of WO2005121084A1 publication Critical patent/WO2005121084A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C07D209/52—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 condensed with a ring other than six-membered

Definitions

  • Ramipril (I) is a known active substance used in treatment of hypertension, chronic heart failure and in prevention of various cardiovascular events. The substance and a method of its preparation was described in patent US 5 061 722.
  • step 4 cis,endo-2-azabicyclo[3.3.0]octane-3-carboxylic acid benzyl ester hydrochloride reacts with N-[l-(S)-(ethoxycarbonyl)-3-phenylpropyl]-alanine. The reaction takes place in dimethylformamide in the presence of dicyclohexylcarbodiimide and 1- hydroxybenzotriazole. After filtering off dicyclohexylurea and extraction the resulting reaction mixture is separated using chromatography and affords 38.6% of the compound of formula IV
  • the total yield of the synthesis ranges from 61.7 % to 74.4 %.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/CZ2005/000048 2004-06-08 2005-06-08 A method of preparation of ramipril Ceased WO2005121084A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CZ20040699A CZ296860B6 (cs) 2004-06-08 2004-06-08 Zpusob výroby ramiprilu
CZPV2004-699 2004-06-08

Publications (1)

Publication Number Publication Date
WO2005121084A1 true WO2005121084A1 (en) 2005-12-22

Family

ID=34970577

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CZ2005/000048 Ceased WO2005121084A1 (en) 2004-06-08 2005-06-08 A method of preparation of ramipril

Country Status (2)

Country Link
CZ (1) CZ296860B6 (cs)
WO (1) WO2005121084A1 (cs)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5061722A (en) * 1981-11-05 1991-10-29 Hoechst Ag Cis, endo-2-azabicyclo-[3.3.0]-octane-3-carboxylic acids, a process for their preparation, agents containing these compounds and their use
WO2003045916A1 (en) * 2001-11-21 2003-06-05 Brantford Chemicals Inc. Process for the preparation of ramipril

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5061722A (en) * 1981-11-05 1991-10-29 Hoechst Ag Cis, endo-2-azabicyclo-[3.3.0]-octane-3-carboxylic acids, a process for their preparation, agents containing these compounds and their use
WO2003045916A1 (en) * 2001-11-21 2003-06-05 Brantford Chemicals Inc. Process for the preparation of ramipril

Also Published As

Publication number Publication date
CZ296860B6 (cs) 2006-07-12
CZ2004699A3 (cs) 2006-01-11

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