WO2004103983A1 - Procede de preparation de derives d'acide benzoique s(+)-2-ethoxy-4-[n-{1-(2-piperidinophelyl)-3-methyl-1- butyl} aminocarbonylmethyl] - Google Patents

Procede de preparation de derives d'acide benzoique s(+)-2-ethoxy-4-[n-{1-(2-piperidinophelyl)-3-methyl-1- butyl} aminocarbonylmethyl] Download PDF

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Publication number
WO2004103983A1
WO2004103983A1 PCT/IN2003/000197 IN0300197W WO2004103983A1 WO 2004103983 A1 WO2004103983 A1 WO 2004103983A1 IN 0300197 W IN0300197 W IN 0300197W WO 2004103983 A1 WO2004103983 A1 WO 2004103983A1
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WO
WIPO (PCT)
Prior art keywords
formula
methyl
ethoxy
butyl
preparation
Prior art date
Application number
PCT/IN2003/000197
Other languages
English (en)
Inventor
Chandrashekar Aswathanarayanappa
Tom Thomas Puthiaparampil
Padudevastana Sathya Shanker
Madhavan Sridharan
Sambasivam Ganesh
Original Assignee
Biocon Limited
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 Biocon Limited filed Critical Biocon Limited
Priority to PCT/IN2003/000197 priority Critical patent/WO2004103983A1/fr
Priority to AU2003237595A priority patent/AU2003237595A1/en
Publication of WO2004103983A1 publication Critical patent/WO2004103983A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Definitions

  • the present invention relates to a novel process for the preparation of S(+) 2-ethoxy-4-[N- ⁇ l-(2-piperidinophelyl)-3- methyl-1- butyl aminocarbonylmethyl]-benzoic acid derivatives.
  • EP 0 207 331 claims two polymorphous forms B and C of 2- ethoxy-4-[N- ⁇ l-(2-piperidinophelyl)-3- methyl-1-butyl aminocarbonylmethyl]-benzoic acid having the Formula IV and process for preparation thereof.
  • EP 0 589 874 claims S(+) 2-ethoxy-4-[N- ⁇ l-(2-piperidinophelyl)- 3- methyl- 1-butyl aminocarbonylmethyl]-benzoic acid having the Formula IV and process for preparation thereof.
  • the compound of formula (IV) is from a new class of hypoglycemic benzoic acid derivatives for the treatment of non-insulin dependent diabetes mellitus (NIDDM).
  • NIDDM non-insulin dependent diabetes mellitus
  • reaction of the amine of Formula II with a carboxylic acid of Formula III is carried out in the presence of N,N'-carbonyldimidazole, N,N'dicyclohexylcarbodiimide or triphenylphosphine/carbon tetrachloride and triethylamine.
  • WO 2003/027072 claims process for preparation of compound of formula I by reacting an S(+) amine compound of formula II with a carboxylic acid of formula III in the presence of pivaloyl chloride and a base.
  • the reagents used here suffer from disadvantages like probable racemisation, expensiveness, additional reagents e.g. a base, low yields of the product, extra purification steps to obtain final product, repeated crystallization, hazardous and industrially impossible.
  • the present invention provides a process for the preparation of compound of formula I comprising, reacting the (S) amine of Formula II
  • the novel process employed in the instant invention has following definite advantages: a) Remarkably low risk of allergization compared to other reagents like DCC. b) Low toxicity of Propane phosphonic anhydride and its reaction products. c) Low racemization of products during reaction. d) By products are water soluble leading to simple work up and easy isolation of product. e) Reaction proceeds under ambient conditions. f) High yields.
  • the present invention provides a process for the preparation of compound of formula I comprising, reacting the (S) amine of Formula II
  • the protecting group P in the compound of Formula III is any carboxylic acid protecting group which can be easily removed, like ester groups.
  • the reaction may be carried out in any suitable solvent such as ethyl acetate, dichloromethane etc.
  • the reaction is carried out at temperatures of between -25°C and

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

L'invention concerne un nouveau procédé de préparation de dérivés d'acide benzoïque S(+)-2-éthoxy-4-[N-{1-(2-pipéridinophenyl)-3-methyl-1-butyl} aminocarbonylméthyl].
PCT/IN2003/000197 2003-05-26 2003-05-26 Procede de preparation de derives d'acide benzoique s(+)-2-ethoxy-4-[n-{1-(2-piperidinophelyl)-3-methyl-1- butyl} aminocarbonylmethyl] WO2004103983A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/IN2003/000197 WO2004103983A1 (fr) 2003-05-26 2003-05-26 Procede de preparation de derives d'acide benzoique s(+)-2-ethoxy-4-[n-{1-(2-piperidinophelyl)-3-methyl-1- butyl} aminocarbonylmethyl]
AU2003237595A AU2003237595A1 (en) 2003-05-26 2003-05-26 Process for the preparation of s(+)-2-ethoxy-4-(n-{1-(2-piperidinophelyl)-3-methyl-1- butyl} aminocarbonylmethyl)benzoic acid derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2003/000197 WO2004103983A1 (fr) 2003-05-26 2003-05-26 Procede de preparation de derives d'acide benzoique s(+)-2-ethoxy-4-[n-{1-(2-piperidinophelyl)-3-methyl-1- butyl} aminocarbonylmethyl]

Publications (1)

Publication Number Publication Date
WO2004103983A1 true WO2004103983A1 (fr) 2004-12-02

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2003/000197 WO2004103983A1 (fr) 2003-05-26 2003-05-26 Procede de preparation de derives d'acide benzoique s(+)-2-ethoxy-4-[n-{1-(2-piperidinophelyl)-3-methyl-1- butyl} aminocarbonylmethyl]

Country Status (2)

Country Link
AU (1) AU2003237595A1 (fr)
WO (1) WO2004103983A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100445275C (zh) * 2006-06-21 2008-12-24 浙江大学 一种合成瑞格列奈的工艺
WO2009004485A2 (fr) * 2007-06-06 2009-01-08 Actavis Group Ptc Ehf Répaglinide sensiblement exempt d'impureté dimère
CN102002021A (zh) * 2010-12-07 2011-04-06 合肥华方医药科技有限公司 一种瑞格列奈的新合成方法
US8101769B2 (en) 2007-02-15 2012-01-24 Actavis Group Ptc Ehf Process for preparing ethyl (S)-2-ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonyl methyl]benzoate and use thereof for the preparation of Repaglinide
CN102633750A (zh) * 2012-03-26 2012-08-15 浙江昂利康制药有限公司 一锅法合成治疗糖尿病的药物瑞格列奈
CN102731436A (zh) * 2012-04-09 2012-10-17 海南中化联合制药工业股份有限公司 一种瑞格列奈的制备及精制方法
FR3016879A1 (fr) * 2014-01-29 2015-07-31 Guillaume Laconde Procede de preparation de benzotriazole n-acyles
CN105198838A (zh) * 2015-10-21 2015-12-30 河南普瑞制药有限公司 一种瑞格列奈的制备方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU3721084A (en) * 1983-12-30 1985-08-01 Dr. Karl Thomae Gmbh Phenyl acetic acid amides
AU8078191A (en) * 1991-06-21 1993-01-25 Novo Nordisk A/S (s)(+)-2-ethoxy-4-(n-(1-(2-piperidinophenyl)-3-methyl-1- butyl)aminocarbonylmethyl)benzoic acid
DE19503325A1 (de) * 1995-02-02 1996-08-08 Hoechst Ag Verfahren zur Herstellung von 3-Hydroxy-N-arylnaphthoesäure-2-amiden aus 3-Hydroxy-2-napthoesäure und aromatischen Aminen mit Alkanphosphonsäureanhydrid als Kondensationsmittel
US5945543A (en) * 1995-07-28 1999-08-31 Basf Aktiengesellschaft Process for producing α-(N,N dialkyl)-amino carboxlic acid amides
EP1031575A1 (fr) * 1999-02-26 2000-08-30 Pfizer Products Inc. Procédé de préparation de secretagogues d'hormone de croissance
WO2003027072A1 (fr) * 2001-09-25 2003-04-03 Ranbaxy Laboratories Limited Processus de preparation de repaglinide

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU3721084A (en) * 1983-12-30 1985-08-01 Dr. Karl Thomae Gmbh Phenyl acetic acid amides
AU5913986A (en) * 1983-12-30 1987-01-08 Dr. Karl Thomae Gmbh Solid forms of 2-ethoxy-4-``N-(1-(2-piperidino-phenyl)-3- methyl-1-butyl)-aminocarbonylmethyl``-benzoic acid
AU8078191A (en) * 1991-06-21 1993-01-25 Novo Nordisk A/S (s)(+)-2-ethoxy-4-(n-(1-(2-piperidinophenyl)-3-methyl-1- butyl)aminocarbonylmethyl)benzoic acid
DE19503325A1 (de) * 1995-02-02 1996-08-08 Hoechst Ag Verfahren zur Herstellung von 3-Hydroxy-N-arylnaphthoesäure-2-amiden aus 3-Hydroxy-2-napthoesäure und aromatischen Aminen mit Alkanphosphonsäureanhydrid als Kondensationsmittel
US5945543A (en) * 1995-07-28 1999-08-31 Basf Aktiengesellschaft Process for producing α-(N,N dialkyl)-amino carboxlic acid amides
EP1031575A1 (fr) * 1999-02-26 2000-08-30 Pfizer Products Inc. Procédé de préparation de secretagogues d'hormone de croissance
WO2003027072A1 (fr) * 2001-09-25 2003-04-03 Ranbaxy Laboratories Limited Processus de preparation de repaglinide

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BERNHAGEN W.: "PPA: a new reagent for peptide synthesis", PHARMACEUTICAL BIOTECHNOLOGY INTERNATIONAL, 1996, pages 31 - 34 *
CRICHFIELD K.S. ET AL.: "Propane phosphonic acid anhydride: a mild reagent for beta-lactam synthesis", SYNTHETIC COMMUNICATIONS, vol. 30, no. 20, 2000, pages 3737 - 3744 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100445275C (zh) * 2006-06-21 2008-12-24 浙江大学 一种合成瑞格列奈的工艺
US8101769B2 (en) 2007-02-15 2012-01-24 Actavis Group Ptc Ehf Process for preparing ethyl (S)-2-ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonyl methyl]benzoate and use thereof for the preparation of Repaglinide
WO2009004485A2 (fr) * 2007-06-06 2009-01-08 Actavis Group Ptc Ehf Répaglinide sensiblement exempt d'impureté dimère
WO2009004485A3 (fr) * 2007-06-06 2009-03-19 Actavis Group Ptc Ehf Répaglinide sensiblement exempt d'impureté dimère
CN102002021A (zh) * 2010-12-07 2011-04-06 合肥华方医药科技有限公司 一种瑞格列奈的新合成方法
CN102633750A (zh) * 2012-03-26 2012-08-15 浙江昂利康制药有限公司 一锅法合成治疗糖尿病的药物瑞格列奈
CN102731436A (zh) * 2012-04-09 2012-10-17 海南中化联合制药工业股份有限公司 一种瑞格列奈的制备及精制方法
FR3016879A1 (fr) * 2014-01-29 2015-07-31 Guillaume Laconde Procede de preparation de benzotriazole n-acyles
FR3016880A1 (fr) * 2014-01-29 2015-07-31 Guillaume Laconde Procede de preparation de benzotriazole n-acyles
CN105198838A (zh) * 2015-10-21 2015-12-30 河南普瑞制药有限公司 一种瑞格列奈的制备方法

Also Published As

Publication number Publication date
AU2003237595A1 (en) 2004-12-13

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