WO2002024625A3 - Process for the preparation of 3-aryl-2-hydroxy propanoic acid derivatives - Google Patents

Process for the preparation of 3-aryl-2-hydroxy propanoic acid derivatives Download PDF

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Publication number
WO2002024625A3
WO2002024625A3 PCT/IB2001/001699 IB0101699W WO0224625A3 WO 2002024625 A3 WO2002024625 A3 WO 2002024625A3 IB 0101699 W IB0101699 W IB 0101699W WO 0224625 A3 WO0224625 A3 WO 0224625A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
pure
produce
aryl
Prior art date
Application number
PCT/IB2001/001699
Other languages
French (fr)
Other versions
WO2002024625A2 (en
Inventor
Rajender Kumar Potlapally
Mahender Rao Siripragada
Narasimha Murthy Kotra
Raju Sirisilla
Ramabhadra Sarma Mamillapalli
Om Reddy Gaddam
Original Assignee
Reddy Research Foundation
Rajender Kumar Potlapally
Mahender Rao Siripragada
Narasimha Murthy Kotra
Raju Sirisilla
Ramabhadra Sarma Mamillapalli
Om Reddy Gaddam
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
Priority claimed from US09/836,559 external-priority patent/US6559335B2/en
Application filed by Reddy Research Foundation, Rajender Kumar Potlapally, Mahender Rao Siripragada, Narasimha Murthy Kotra, Raju Sirisilla, Ramabhadra Sarma Mamillapalli, Om Reddy Gaddam filed Critical Reddy Research Foundation
Priority to AU2001286163A priority Critical patent/AU2001286163A1/en
Publication of WO2002024625A2 publication Critical patent/WO2002024625A2/en
Publication of WO2002024625A3 publication Critical patent/WO2002024625A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups

Abstract

The present invention relates to an improved process for the preparation of 3-aryl-2-hydroxy propanoic acid derivatives of formula (1) where R1 represents hydrogen atom or (C¿1?-C6)alkyl group and R?2¿ represents (C¿1?-C6)alkyl group which comprises: (i) selectively benzylating L-tyrosine to yield compound of formula (15); (ii). diazotising the compound of formula (15) to produce compound of formula (8); (iii) simultaneous etherification and esterification of compound of formula (8) to obtain crude compound of formula (9) with ee>90 %; (iv) hydrolysing the crude compound of formula (9) to produce compound of formula (9a) acid; (v) treating the compound of formula (9a) with chiral base to produce pure salt of formula (16); (vi) converting the compound of formula (16) to pure compound of formula (9a); (vii) esterifying pure compound of formula (9a) to produce pure compound of formula (9); (viii) debenzylating the compound of formula (9) to yield pure compound of formula (1).
PCT/IB2001/001699 2000-09-22 2001-09-17 Process for the preparation of 3-aryl-2-hydroxy propanoic acid derivatives WO2002024625A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001286163A AU2001286163A1 (en) 2000-09-22 2001-09-17 An improved process for the preparation of 3-aryl-2-hydroxy propanoic acid derivatives

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN795MA2000 2000-09-22
IN795/MAS/2000 2000-09-22
US09/836,559 2001-04-17
US09/836,559 US6559335B2 (en) 2000-09-22 2001-04-17 Process for the preparation of 3-aryl-2-hydroxy propanoic acid

Publications (2)

Publication Number Publication Date
WO2002024625A2 WO2002024625A2 (en) 2002-03-28
WO2002024625A3 true WO2002024625A3 (en) 2002-06-27

Family

ID=26324896

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2001/001699 WO2002024625A2 (en) 2000-09-22 2001-09-17 Process for the preparation of 3-aryl-2-hydroxy propanoic acid derivatives

Country Status (2)

Country Link
AU (1) AU2001286163A1 (en)
WO (1) WO2002024625A2 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2527953A1 (en) * 2003-06-06 2005-03-03 Cadila Healthcare Limited Process for preparing 3-aryl-2-hydroxy propanoic acid derivatives without resolution
JP2006001882A (en) * 2004-06-17 2006-01-05 Ajinomoto Co Inc Method for producing o-substituted tyrosine compound
RS54735B1 (en) 2011-01-31 2016-10-31 Cadila Healthcare Ltd Treatment for lipodystrophy
EA201592020A1 (en) 2013-04-22 2016-05-31 Кадила Хелзкэр Лимитед NEW COMPOSITION FOR NONALCOHOLIC FATIAL LIVER DISEASE (NAFLD)
WO2014181362A1 (en) 2013-05-09 2014-11-13 Council Of Scientific & Industrial Research A process for the preparation of 3-aryl-2-hydroxy propanoic acid compounds
US20160107989A1 (en) 2013-05-30 2016-04-21 Cadila Healthcare Limited A process for preparation of pyrroles having hypolipidemic hypocholesteremic activities
TW201636015A (en) 2013-07-05 2016-10-16 卡地拉保健有限公司 Synergistic compositions
IN2013MU02470A (en) 2013-07-25 2015-06-26 Cadila Healthcare Ltd
IN2013MU02905A (en) 2013-09-06 2015-07-03 Cadila Healthcare Ltd
US10385017B2 (en) 2015-10-14 2019-08-20 Cadila Healthcare Limited Pyrrole compound, compositions and process for preparation thereof
ES2894261T3 (en) 2016-12-09 2022-02-14 Cadila Healthcare Ltd Treatment of primary biliary cholangitis

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000026200A1 (en) * 1998-10-29 2000-05-11 Dr. Reddy's Research Foundation An improved process for the preparation of new antidiabetic agents

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000026200A1 (en) * 1998-10-29 2000-05-11 Dr. Reddy's Research Foundation An improved process for the preparation of new antidiabetic agents

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HAIGH D ET AL: "NON-THIAZOLIDINEDIONE ANTIHYPERGLYCAEMIC AGENTS. PART 3: THE EFFECTS OF STEREOCHEMISTRY ON THE POTENCY OF ALPHA-METHOXY-BETA-PHENYLPROPAN OIC ACIDS", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER SCIENCE LTD, GB, vol. 7, 1999, pages 821 - 830, XP000995637, ISSN: 0968-0896 *

Also Published As

Publication number Publication date
WO2002024625A2 (en) 2002-03-28
AU2001286163A1 (en) 2002-04-02

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