WO2007029267A1 - Procédé de préparation industriellement viable du chlorhydrate d'imidapril - Google Patents

Procédé de préparation industriellement viable du chlorhydrate d'imidapril Download PDF

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Publication number
WO2007029267A1
WO2007029267A1 PCT/IN2006/000183 IN2006000183W WO2007029267A1 WO 2007029267 A1 WO2007029267 A1 WO 2007029267A1 IN 2006000183 W IN2006000183 W IN 2006000183W WO 2007029267 A1 WO2007029267 A1 WO 2007029267A1
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WO
WIPO (PCT)
Prior art keywords
formula
product
acid
hydrochloride
methyl
Prior art date
Application number
PCT/IN2006/000183
Other languages
English (en)
Inventor
Ramesh Babu Potluri
Hariharakrishnan Venkata Subramanian
Hari Prasad Kodali
Original Assignee
Ramesh Babu Potluri
Venkata Subramanian Hariharakr
Hari Prasad Kodali
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 Ramesh Babu Potluri, Venkata Subramanian Hariharakr, Hari Prasad Kodali filed Critical Ramesh Babu Potluri
Publication of WO2007029267A1 publication Critical patent/WO2007029267A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, 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
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/32—One oxygen atom
    • C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms

Definitions

  • the invention relates to a novel method for the preparation of imidapril hydrochloride of formula I
  • the chemical entity (4S)-3-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3- phenylpropyl]amino]-1-oxopropyl]-1-methyl-2-oxo-4-imidazolidinecarboxylic acid hydrochloride of formula I belongs to a group of medicines called ACE inhibitors, which block the action of a chemical in the body called angiotensin converting enzyme (ACE). Normally ACE produces another chemical, angiotensin II. Thus imidapril reduces the amount of angiotensin Il in the blood. Angiotensin Il has two actions.
  • EP 95163/US4508727 discloses synthesis of imidapril hydrochloride of formula employing several stages. This is shown in the following schemes IA and IB
  • ECPP alanine of formula-Ilia is activated with N- hyroxysuccinicimide using dicyclohexylcarbodiimide and the activated ester is coupled with t-butyl imidaozlinone-4-carboxylate of formula-ll a in the presence of potassium tert. butoxide to give a dipeptide of formula-V, which is converted to the product of formula-l by treatment with dioxane-HCI
  • the scheme I B describes a methodology, which is similar to the one described in scheme IA, except the fact that benzyl imidazolidinone-4-carboxylate of formula-l I b is used instead of the t-butyl ester Ha.
  • the coupled product of formula-VI is debenzylated using Pd/C - H 2 and treated with dioxane-HCI to get the product of formula-l.
  • the present invention provides a novel process for the preparation of imidapril of formula I by reacting esters of 4(S)-1-methyl-2-oxoimidazolidine-4-carboxylate of formula-ll with (S)-ethyl-2-[(S)-4-methyl-2,5-dioxooxazolidin-3-yl]-4-phenylbutanoate of formula-Ill in presence of a base like sodium hydride/sodium methoxide, potassium tert. butoxide etc. After the coupling, the protecting group was removed by means of catalytic hydrogenation or hydrolysis to get the required compound
  • the reaction of the product of formula-Ill with imidazolidinone-4-carboxylicacid of formula-ll was tried using different bases viz., NaH, NaOBu', KOBu 1 , NaNH 2 etc. It was preferable to use NaH, Na/KOBu 1 . It was more preferable to use Na/KOBu 1 .
  • the reaction was studied in different solvents like dichloroethane, dichloromethane, acetonitrile, tetrahydrofuran, 2 or 3 methyl tetrahydrofuran, 1,4-dioxane, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane etc.
  • esters of 4(S)-1-methyl-2-oxoimidazolidine-4- carboxylate of formula-ll with (S)-ethyl-2-[(S)-4-methyl-2,5-dioxooxazolidin ⁇ 3-yl]-4- phenylbutanoate of formula-Ill can be prepared conventionally by well known methods.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un procédé innovant de préparation de chlorhydrate d'imidapril de formule (I). Selon ledit procédé, on fait réagir des esters de 4-carboxylate de 4(S)-1-méthyl-2-oxoimidazolidine de formule (II) avec du 4-phénylbutanoate de (S)-éthyl-2-[(S)-4-méthyl-2,5-dioxooxazolidin-3-yl] de formule (III) et on hydrolyse le produit couplé avec un chlorhydrate alcoolique.
PCT/IN2006/000183 2005-09-06 2006-05-29 Procédé de préparation industriellement viable du chlorhydrate d'imidapril WO2007029267A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1247CH2005 2005-09-06
IN1247/CHE/2005 2005-09-06

Publications (1)

Publication Number Publication Date
WO2007029267A1 true WO2007029267A1 (fr) 2007-03-15

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WO (1) WO2007029267A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104119424A (zh) * 2014-07-01 2014-10-29 上海天慈生物谷生物工程有限公司 (4s)-3-[(2s)-2[(1s)-1-乙氧羰基-3-苯丙基]氨基丙酰基]-1-甲基-2-氧代咪唑啉-4-羧酸的制备方法
CN111253315A (zh) * 2020-03-10 2020-06-09 北京阳光诺和药物研究有限公司 盐酸咪达普利有机杂质及其制备方法
CN113024632A (zh) * 2021-03-28 2021-06-25 山东中健康桥制药有限公司 一种盐酸咪达普利的制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6541635B1 (en) * 2002-03-29 2003-04-01 Everlight Usa, Inc. Method for producing angiotensin converting enzyme inhibitor

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6541635B1 (en) * 2002-03-29 2003-04-01 Everlight Usa, Inc. Method for producing angiotensin converting enzyme inhibitor

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104119424A (zh) * 2014-07-01 2014-10-29 上海天慈生物谷生物工程有限公司 (4s)-3-[(2s)-2[(1s)-1-乙氧羰基-3-苯丙基]氨基丙酰基]-1-甲基-2-氧代咪唑啉-4-羧酸的制备方法
CN104119424B (zh) * 2014-07-01 2018-12-18 上海天慈生物谷生物工程有限公司 (4s)-3-[(2s)-2[(1s)-1-乙氧羰基-3-苯丙基]氨基丙酰基]-1-甲基-2-氧代咪唑啉-4-羧酸的制备方法
CN111253315A (zh) * 2020-03-10 2020-06-09 北京阳光诺和药物研究有限公司 盐酸咪达普利有机杂质及其制备方法
CN113024632A (zh) * 2021-03-28 2021-06-25 山东中健康桥制药有限公司 一种盐酸咪达普利的制备方法

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