WO2011040717A3 - Method for preparing intermediate of sitagliptin using chiral oxirane - Google Patents

Method for preparing intermediate of sitagliptin using chiral oxirane Download PDF

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Publication number
WO2011040717A3
WO2011040717A3 PCT/KR2010/006346 KR2010006346W WO2011040717A3 WO 2011040717 A3 WO2011040717 A3 WO 2011040717A3 KR 2010006346 W KR2010006346 W KR 2010006346W WO 2011040717 A3 WO2011040717 A3 WO 2011040717A3
Authority
WO
WIPO (PCT)
Prior art keywords
sitagliptin
preparing intermediate
chiral oxirane
oxirane
chiral
Prior art date
Application number
PCT/KR2010/006346
Other languages
French (fr)
Other versions
WO2011040717A2 (en
Inventor
Nam Du Kim
Ji Yeon Chang
Jae Hyuk Jung
Hyun Seung Lee
Dong Jun Kim
Young Kil Chang
Gwan Sun Lee
Original Assignee
Hanmi Holdings Co., 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 Hanmi Holdings Co., Ltd. filed Critical Hanmi Holdings Co., Ltd.
Publication of WO2011040717A2 publication Critical patent/WO2011040717A2/en
Publication of WO2011040717A3 publication Critical patent/WO2011040717A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/36—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Disclosed is: a novel, simple and low-cost method for preparing 3-hydroxy-4-(2,4,5-trifluorophenyl)-butyric acid, particularly (3S)-3-hydroxy-4-(2,4,5-trifluorophenyl)-butyric acid, which is used as a key intermediate in the preparation of sitagliptin.
PCT/KR2010/006346 2009-10-01 2010-09-16 Method for preparing intermediate of sitagliptin using chiral oxirane WO2011040717A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020090093894A KR101253106B1 (en) 2009-10-01 2009-10-01 Method for preparing intermediate of sitagliptin using chiral oxirane
KR10-2009-0093894 2009-10-01

Publications (2)

Publication Number Publication Date
WO2011040717A2 WO2011040717A2 (en) 2011-04-07
WO2011040717A3 true WO2011040717A3 (en) 2011-10-13

Family

ID=43826758

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2010/006346 WO2011040717A2 (en) 2009-10-01 2010-09-16 Method for preparing intermediate of sitagliptin using chiral oxirane

Country Status (4)

Country Link
KR (1) KR101253106B1 (en)
AR (1) AR079102A1 (en)
TW (1) TW201118101A (en)
WO (1) WO2011040717A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102838511A (en) * 2011-06-24 2012-12-26 浙江海翔药业股份有限公司 Sitagliptin intermediates as well as preparation method and application of intermediate
CN113979853A (en) * 2021-11-24 2022-01-28 上海科利生物医药有限公司 Preparation method of (S) -3-hydroxy-4- (2,4, 5-trifluorophenyl) butyric acid

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2108767A2 (en) * 1970-10-02 1972-05-26 Synthelabo 2-carbamyloxy-3-phenylbutyronitriles - with hypnotic activity
WO2004087650A2 (en) * 2003-03-27 2004-10-14 Merck & Co. Inc. Process and intermediates for the preparation of beta-amino acid amide dipeptidyl peptidase-iv inhibitors
WO2009045507A2 (en) * 2007-10-03 2009-04-09 Teva Pharmaceutical Industries Ltd. Processes for preparing an intermediate of sitagliptin via enzymatic reduction

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090192326A1 (en) 2007-11-13 2009-07-30 Nurit Perlman Preparation of sitagliptin intermediate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2108767A2 (en) * 1970-10-02 1972-05-26 Synthelabo 2-carbamyloxy-3-phenylbutyronitriles - with hypnotic activity
WO2004087650A2 (en) * 2003-03-27 2004-10-14 Merck & Co. Inc. Process and intermediates for the preparation of beta-amino acid amide dipeptidyl peptidase-iv inhibitors
WO2009045507A2 (en) * 2007-10-03 2009-04-09 Teva Pharmaceutical Industries Ltd. Processes for preparing an intermediate of sitagliptin via enzymatic reduction

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JOHN W. KRAMER ET AL.: "Fluorinated beta-lactones and poly(beta-hydroxyalkanoate)s : synthesis via epoxide carbonylation and ring-opening polymerization", TETR AHEDRON., vol. 64, 2008, pages 6973 - 6978 *

Also Published As

Publication number Publication date
KR101253106B1 (en) 2013-04-10
KR20110036308A (en) 2011-04-07
AR079102A1 (en) 2011-12-28
TW201118101A (en) 2011-06-01
WO2011040717A2 (en) 2011-04-07

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