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TW200514556A - Synthesis and purification of nateglinide - Google Patents

Synthesis and purification of nateglinide

Info

Publication number
TW200514556A
TW200514556A TW092129454A TW92129454A TW200514556A TW 200514556 A TW200514556 A TW 200514556A TW 092129454 A TW092129454 A TW 092129454A TW 92129454 A TW92129454 A TW 92129454A TW 200514556 A TW200514556 A TW 200514556A
Authority
TW
Taiwan
Prior art keywords
formula
phenylalanine
trans
nateglinide
synthesis
Prior art date
Application number
TW092129454A
Other languages
Chinese (zh)
Inventor
Samir Jaivant Naik
Pramila Vijay Kulkarni
Nandkumar Baburao Gaikwad
Mangesh Shivram Sawant
Shekhar Bhaskar Bhirud
Chandrasekhar Batchu
Original Assignee
Glenmark Pharmaceuticals Ltd
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 Glenmark Pharmaceuticals Ltd filed Critical Glenmark Pharmaceuticals Ltd
Publication of TW200514556A publication Critical patent/TW200514556A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
    • A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Endocrinology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Disclosed is a method for the synthesis of [(trans-4-isopropyl cyclohexyl)-carbonyl]-D-phenylalanine (nateglinide) (formula I), including the steps of: (i) reacting trans-4-isopropyl cyclohexyl carboxylic acid (formula (5)), with an alkyl chloroformate (formula (13)), where R represents an alkyl group, in a ketonic solvent in the presence of a base at a temperature in the range of -20 DEG to 30 DEG C to form the mixed anhydride of formula (14); and, (ii) reacting said mixed anhydride with an aqueous alkali salt solution of D-phenylalanine to yield a reaction mixture including [(trans-4-isopropyl cyclohexyl)-carbonyl]-D-phenylalanine.
TW092129454A 2002-08-26 2003-10-23 Synthesis and purification of nateglinide TW200514556A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IN773MU2002 2002-08-26

Publications (1)

Publication Number Publication Date
TW200514556A true TW200514556A (en) 2005-05-01

Family

ID=34259967

Family Applications (1)

Application Number Title Priority Date Filing Date
TW092129454A TW200514556A (en) 2002-08-26 2003-10-23 Synthesis and purification of nateglinide

Country Status (3)

Country Link
AR (1) AR041057A1 (en)
TW (1) TW200514556A (en)
WO (1) WO2004018408A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU227073B1 (en) 2003-07-10 2010-06-28 Richter Gedeon Nyrt Process for the preparation of chirally pure n-(trans-4-isopropyl-cyclohexylcarbonyl)-d-phenyl-alanine (nateglinide) and it's crystalline forms and the cristalline form g
GB0413084D0 (en) 2004-06-11 2004-07-14 Cipla Ltd Process
WO2007135533A1 (en) * 2006-05-23 2007-11-29 Aurobindo Pharma Limited Process for preparing nateglinide b-type crystals
KR20150146007A (en) 2014-06-20 2015-12-31 주식회사 씨트리 A new method for producing nateglinide

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0717899A (en) * 1993-07-01 1995-01-20 Ajinomoto Co Inc Production of carboxylic acid chloride

Also Published As

Publication number Publication date
WO2004018408A8 (en) 2005-03-10
WO2004018408A1 (en) 2004-03-04
AR041057A1 (en) 2005-04-27

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