WO2006065826A3 - Process to chiral beta amino acid derivatives by asymmetric hydrogenation - Google Patents

Process to chiral beta amino acid derivatives by asymmetric hydrogenation Download PDF

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Publication number
WO2006065826A3
WO2006065826A3 PCT/US2005/045096 US2005045096W WO2006065826A3 WO 2006065826 A3 WO2006065826 A3 WO 2006065826A3 US 2005045096 W US2005045096 W US 2005045096W WO 2006065826 A3 WO2006065826 A3 WO 2006065826A3
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WO
WIPO (PCT)
Prior art keywords
amino acid
useful
beta amino
acid derivatives
chiral
Prior art date
Application number
PCT/US2005/045096
Other languages
French (fr)
Other versions
WO2006065826A2 (en
Inventor
Tesfaye Biftu
Zhiguo J Song
Fei Zhang
Thorsten Rosner
Karl Hansen
Joseph D Armstrong Iii
Original Assignee
Merck & Co Inc
Tesfaye Biftu
Zhiguo J Song
Fei Zhang
Thorsten Rosner
Karl Hansen
Joseph D Armstrong Iii
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 Merck & Co Inc, Tesfaye Biftu, Zhiguo J Song, Fei Zhang, Thorsten Rosner, Karl Hansen, Joseph D Armstrong Iii filed Critical Merck & Co Inc
Publication of WO2006065826A2 publication Critical patent/WO2006065826A2/en
Publication of WO2006065826A3 publication Critical patent/WO2006065826A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The present invention relates to a process for the efficient preparation of enantiomerically enriched beta amino acid derivatives which are useful in the asymmetric synthesis of biologically active molecules. The process comprises an enantioselective hydrogenation of a prochiral beta amino acrylic acid derivative substrate in the presence of a transition metal precursor complexed with a chiral ferrocenyl diphosphine ligand with in situ protection of the primary amine product. The invention also relates to a novel process for the preparation of chiral beta-amino acid amides as inhibitors of the dipeptidyl peptidase-IV of structural formula III and the useful intermediates obtained therein. The products resulting from the instant process are inhibitors of dipeptidyl peptidase-IV and thereby useful for the treatment of Type 2 diabetes.
PCT/US2005/045096 2004-12-15 2005-12-12 Process to chiral beta amino acid derivatives by asymmetric hydrogenation WO2006065826A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US63622304P 2004-12-15 2004-12-15
US60/636,223 2004-12-15
US65916505P 2005-03-07 2005-03-07
US60/659,165 2005-03-07

Publications (2)

Publication Number Publication Date
WO2006065826A2 WO2006065826A2 (en) 2006-06-22
WO2006065826A3 true WO2006065826A3 (en) 2006-10-05

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/045096 WO2006065826A2 (en) 2004-12-15 2005-12-12 Process to chiral beta amino acid derivatives by asymmetric hydrogenation

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WO (1) WO2006065826A2 (en)

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RU2009108280A (en) 2006-08-08 2010-09-20 Санофи-Авентис (Fr) Arylamino-arylalkyl-substituted imidazolidine-2,4-dione, methods for their preparation containing these compounds and their use
CN101511830B (en) * 2006-09-15 2013-07-24 霍夫曼-拉罗奇有限公司 Process for the preparation of pyrido[2,1-a]isoquinoline derivatives by catalytic asymmetric hydrogenation of an enamine
EP2025674A1 (en) 2007-08-15 2009-02-18 sanofi-aventis Substituted tetra hydro naphthalines, method for their manufacture and their use as drugs
WO2010003624A2 (en) 2008-07-09 2010-01-14 Sanofi-Aventis Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof
WO2010068601A1 (en) 2008-12-08 2010-06-17 Sanofi-Aventis A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof
NZ596713A (en) 2009-05-11 2014-10-31 Generics Uk Ltd Sitagliptin synthesis
WO2011023754A1 (en) 2009-08-26 2011-03-03 Sanofi-Aventis Novel crystalline heteroaromatic fluoroglycoside hydrates, pharmaceuticals comprising these compounds and their use
WO2011103256A1 (en) 2010-02-22 2011-08-25 Merck Sharp & Dohme Corp. Substituted aminotetrahydrothiopyrans and derivatives thereof as dipeptidyl peptidase-iv inhibitors for the treatment of diabetes
WO2011107494A1 (en) 2010-03-03 2011-09-09 Sanofi Novel aromatic glycoside derivatives, medicaments containing said compounds, and the use thereof
EP2571876B1 (en) 2010-05-21 2016-09-07 Merck Sharp & Dohme Corp. Substituted seven-membered heterocyclic compounds as dipeptidyl peptidase-iv inhibitors for the treatment of diabetes
EP2582709B1 (en) 2010-06-18 2018-01-24 Sanofi Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases
US8530413B2 (en) 2010-06-21 2013-09-10 Sanofi Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments
TW201221505A (en) 2010-07-05 2012-06-01 Sanofi Sa Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament
TW201215388A (en) 2010-07-05 2012-04-16 Sanofi Sa (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments
TW201215387A (en) 2010-07-05 2012-04-16 Sanofi Aventis Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament
WO2012078448A1 (en) 2010-12-06 2012-06-14 Schering Corporation Tricyclic heterocycles useful as dipeptidyl peptidase-iv inhibitors
US8901114B2 (en) 2011-03-08 2014-12-02 Sanofi Oxathiazine derivatives substituted with carbocycles or heterocycles, method for producing same, drugs containing said compounds, and use thereof
WO2012120054A1 (en) 2011-03-08 2012-09-13 Sanofi Di- and tri-substituted oxathiazine derivates, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof
EP2683704B1 (en) 2011-03-08 2014-12-17 Sanofi Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof
US8871758B2 (en) 2011-03-08 2014-10-28 Sanofi Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof
EP2683699B1 (en) 2011-03-08 2015-06-24 Sanofi Di- and tri-substituted oxathiazine derivates, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof
CA2840814A1 (en) 2011-06-29 2013-01-03 Ranbaxy Laboratories Limited Solid dispersions of sitagliptin and processes for their preparation
CN103987388A (en) 2011-06-29 2014-08-13 默沙东公司 Novel crystalline forms of a dipeptidyl peptidase-iv inhibitor
AU2012277403A1 (en) 2011-06-30 2014-01-30 Ranbaxy Laboratories Limited Novel salts of sitagliptin
WO2013006526A2 (en) 2011-07-05 2013-01-10 Merck Sharp & Dohme Corp. Tricyclic heterocycles useful as dipeptidyl peptidase-iv inhibitors
WO2013037390A1 (en) 2011-09-12 2013-03-21 Sanofi 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
WO2013045413A1 (en) 2011-09-27 2013-04-04 Sanofi 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
EP2788352A1 (en) 2011-12-08 2014-10-15 Ranbaxy Laboratories Limited Amorphous form of sitagliptin salts
WO2013122920A1 (en) 2012-02-17 2013-08-22 Merck Sharp & Dohme Corp. Dipeptidyl peptidase-iv inhibitors for the treatment or prevention of diabetes
WO2014018350A1 (en) 2012-07-23 2014-01-30 Merck Sharp & Dohme Corp. Treating diabetes with dipeptidyl peptidase-iv inhibitors
EP2874626A4 (en) 2012-07-23 2016-03-23 Merck Sharp & Dohme Treating diabetes with dipeptidyl peptidase-iv inhibitors
EP2911655A1 (en) 2012-10-24 2015-09-02 INSERM (Institut National de la Santé et de la Recherche Médicale) Tpl2 kinase inhibitors for preventing or treating diabetes and for promoting -cell survival
CN103121976A (en) * 2012-12-07 2013-05-29 苏州百灵威超精细材料有限公司 Preparation method of N-monosubstituted homopiperazines
US9988421B2 (en) 2014-01-10 2018-06-05 Cornell University Dipeptides as inhibitors of human immunoproteasomes
JP6574474B2 (en) 2014-07-21 2019-09-11 メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． Process for producing chiral dipeptidyl peptidase-IV inhibitor
US11202817B2 (en) 2014-08-18 2021-12-21 Cornell University Dipeptidomimetics as inhibitors of human immunoproteasomes
ES2805743T3 (en) 2015-03-24 2021-02-15 Inst Nat Sante Rech Med Method and pharmaceutical composition for use in the treatment of diabetes
EP3362754B1 (en) 2015-10-15 2021-12-22 Cornell University Proteasome inhibitors and uses thereof
US11203613B2 (en) 2017-10-11 2021-12-21 Cornell University Peptidomimetic proteasome inhibitors
CN113636950B (en) 2020-05-11 2023-01-17 浙江医药股份有限公司新昌制药厂 Preparation method of chiral 4-aryl-beta-amino acid derivative

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004037169A2 (en) * 2002-10-18 2004-05-06 Merck & Co., Inc. Beta-amino heterocyclic dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes
WO2004085378A1 (en) * 2003-03-19 2004-10-07 Merck & Co. Inc. Process for the preparation of chiral beta amino acid derivatives by asymmetric hydrogenation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004037169A2 (en) * 2002-10-18 2004-05-06 Merck & Co., Inc. Beta-amino heterocyclic dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes
WO2004085378A1 (en) * 2003-03-19 2004-10-07 Merck & Co. Inc. Process for the preparation of chiral beta amino acid derivatives by asymmetric hydrogenation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
YI HSIAO ET AL: "Highly Efficient Synthesis of beta-Amino Acid Derivatives via Asymmetric Hydrogenation of Unprotected Enamines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 126, no. 32, 21 July 2004 (2004-07-21), pages 9918 - 9919, XP002339712, ISSN: 0002-7863 *

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