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AR043443A1 - PROCEDURE FOR THE PREPARATION OF TETRAHYDROTRIAZOLOPIRAZINS AND INTERMEDIATE PRODUCTS - Google Patents

PROCEDURE FOR THE PREPARATION OF TETRAHYDROTRIAZOLOPIRAZINS AND INTERMEDIATE PRODUCTS

Info

Publication number
AR043443A1
AR043443A1 ARP040100646A AR043443A1 AR 043443 A1 AR043443 A1 AR 043443A1 AR P040100646 A ARP040100646 A AR P040100646A AR 043443 A1 AR043443 A1 AR 043443A1
Authority
AR
Argentina
Prior art keywords
procedure
preparation
atoms
alkyl
compound
Prior art date
Application number
Other languages
Spanish (es)
Original Assignee
Merck & Co Inc
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 filed Critical Merck & Co Inc
Publication of AR043443A1 publication Critical patent/AR043443A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Se proporciona un procedimiento para la preparación de 5,6,7,8-tetrahidro[1,2,4]-triazolo[4,3-a]pirazinas sustituidas que son útiles en la síntesis de inhibidores de la dipeptidil peptidasa-IV para el tratamiento de la diabetes tipo 2. También se proporcionan productos intermedios útiles obtenidos en el procedimiento. Reivindicación 1: Un procedimiento para preparar un compuesto de fórmula estructural (1) o una sal ácida del mismo, en la que R1 es fenilo opcionalmente sustituido o alquilo C1-4 insustituido o sustituido con uno a cinco átomos de F; y R2, R3, R4, y R5 son cada uno de forma independiente H, alquilo C1-4 o bencilo opcionalmente sustituido; o R2 y R3 tomados juntos con los átomos de C a los que están unidos forman un anillo alifático cíclico de 5 a 7 miembros, que comprende la etapa de ciclar un compuesto de fórmula estructural IV en un disolvente orgánico adecuado.A process is provided for the preparation of 5,6,7,8-tetrahydro [1,2,4] -triazolo [4,3-a] substituted pyrazines that are useful in the synthesis of dipeptidyl peptidase-IV inhibitors for the treatment of type 2 diabetes. Useful intermediates obtained in the procedure are also provided. Claim 1: A process for preparing a compound of structural formula (1) or an acid salt thereof, wherein R1 is optionally substituted phenyl or unsubstituted C1-4 alkyl or substituted with one to five F atoms; and R2, R3, R4, and R5 are each independently H, C1-4 alkyl or optionally substituted benzyl; or R2 and R3 taken together with the C atoms to which they are attached form a 5- to 7-membered cyclic aliphatic ring, which comprises the step of cycling a compound of structural formula IV into a suitable organic solvent.

ARP040100646 2003-03-07 2004-03-01 PROCEDURE FOR THE PREPARATION OF TETRAHYDROTRIAZOLOPIRAZINS AND INTERMEDIATE PRODUCTS AR043443A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US45274803P 2003-03-07 2003-03-07

Publications (1)

Publication Number Publication Date
AR043443A1 true AR043443A1 (en) 2005-07-27

Family

ID=32990678

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP040100646 AR043443A1 (en) 2003-03-07 2004-03-01 PROCEDURE FOR THE PREPARATION OF TETRAHYDROTRIAZOLOPIRAZINS AND INTERMEDIATE PRODUCTS

Country Status (3)

Country Link
AR (1) AR043443A1 (en)
TW (1) TW200500368A (en)
WO (1) WO2004080958A2 (en)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE374181T1 (en) 2001-06-27 2007-10-15 Smithkline Beecham Corp FLUORPYRROLIDINES AS DIPEPTIDYLPEPTIDASE INHIBITORS
US20040242566A1 (en) 2003-03-25 2004-12-02 Syrrx, Inc. Dipeptidyl peptidase inhibitors
EP1625122A1 (en) 2003-05-14 2006-02-15 Takeda San Diego, Inc. Dipeptidyl peptidase inhibitors
CA2535619A1 (en) 2003-08-13 2005-02-24 Takeda Pharmaceutical Company Limited 4-pyrimidone derivatives and their use as peptidyl peptidase inhibitors
CN101087756B (en) 2004-07-23 2011-04-06 纽阿达有限责任公司 Peptidase inhibitors
ME02005B (en) 2005-09-14 2012-08-31 Takeda Pharmaceuticals Co Dipeptidyl peptidase inhibitors for treating diabetes
CN101360723A (en) 2005-09-16 2009-02-04 武田药品工业株式会社 Process for preparing pyrimidinedione derivatives
WO2007112347A1 (en) 2006-03-28 2007-10-04 Takeda Pharmaceutical Company Limited Dipeptidyl peptidase inhibitors
US8324383B2 (en) 2006-09-13 2012-12-04 Takeda Pharmaceutical Company Limited Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile
TW200838536A (en) 2006-11-29 2008-10-01 Takeda Pharmaceutical Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor
US8093236B2 (en) 2007-03-13 2012-01-10 Takeda Pharmaceuticals Company Limited Weekly administration of dipeptidyl peptidase inhibitors
US10065960B2 (en) 2010-04-02 2018-09-04 Ogeda Sa NK-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in NK-3 receptors mediated disorders
MX342161B (en) 2010-04-02 2016-09-19 Euroscreen Sa Novel nk-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in nk-3 receptors mediated disorders.
CN102372716A (en) 2010-08-09 2012-03-14 江苏恒瑞医药股份有限公司 Phthalazone derivative, its preparation method and application in medicine thereof
CN101973997B (en) * 2010-09-30 2012-06-06 浙江大学 Method for preparing sitagliptin phosphate side chain
US20150025080A1 (en) 2011-06-29 2015-01-22 Ranbaxy Laboratories Limited Solid dispersions of sitagliptin and processes for their preparation
AU2012277403A1 (en) 2011-06-30 2014-01-30 Ranbaxy Laboratories Limited Novel salts of sitagliptin
US9475814B2 (en) 2011-10-03 2016-10-25 Euroscreen S.A. Chiral N-acyl-5,6,7(8-substituted)-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazines as selective NK-3 receptor antagonists, pharmaceutical composition, methods for use in NK-3 receptor mediated disorders and chiral synthesis thereof
EP2788352A1 (en) 2011-12-08 2014-10-15 Ranbaxy Laboratories Limited Amorphous form of sitagliptin salts
EP3197876B1 (en) 2014-09-25 2018-11-28 Ogeda Sa Novel chiral synthesis of n-acyl-(3-substituted)-(8-substituted)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazines
EP3159343B1 (en) 2015-10-22 2017-07-19 F.I.S.- Fabbrica Italiana Sintetici S.p.A. Improved process for the preparation of triazole and salt thereof
US10047094B1 (en) 2017-02-10 2018-08-14 F.I.S.—Fabbrica Italiana Sintetici S.p.A. Process for the preparation of triazole and salt thereof
ES2733477T3 (en) 2017-07-04 2019-11-29 Fis Fabbrica Italiana Sintetici Spa Effective procedure for the preparation of sitagliptin through a very effective preparation of the intermediate 2,4,5-trifluorophenylacetic acid
BR112020013449A2 (en) * 2018-01-09 2020-12-01 Jiangsu Hengrui Medicine Co., Ltd. methods of preparing a parp inhibitor and an intermediate thereof and method of purifying an intermediate
ES2770143T3 (en) 2018-02-13 2020-06-30 Fis Fabbrica Italiana Sintetici Spa New efficient procedure for the preparation of sitagliptin

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3252483B2 (en) * 1992-10-20 2002-02-04 東レ株式会社 Method for producing tricyclic triazolo derivative
UA74912C2 (en) * 2001-07-06 2006-02-15 Merck & Co Inc Beta-aminotetrahydroimidazo-(1,2-a)-pyrazines and tetratriazolo-(4,3-a)-pyrazines as inhibitors of dipeptylpeptidase for the treatment or prevention of diabetes
MY139563A (en) * 2002-09-04 2009-10-30 Bristol Myers Squibb Co Heterocyclic aromatic compounds useful as growth hormone secretagogues

Also Published As

Publication number Publication date
WO2004080958A2 (en) 2004-09-23
WO2004080958A3 (en) 2004-12-23
TW200500368A (en) 2005-01-01

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