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WO2012035549A3 - An improved process for the synthesis of beta amino acid derivatives - Google Patents

An improved process for the synthesis of beta amino acid derivatives Download PDF

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Publication number
WO2012035549A3
WO2012035549A3 PCT/IN2011/000621 IN2011000621W WO2012035549A3 WO 2012035549 A3 WO2012035549 A3 WO 2012035549A3 IN 2011000621 W IN2011000621 W IN 2011000621W WO 2012035549 A3 WO2012035549 A3 WO 2012035549A3
Authority
WO
WIPO (PCT)
Prior art keywords
synthesis
amino acid
acid derivatives
improved process
beta amino
Prior art date
Application number
PCT/IN2011/000621
Other languages
French (fr)
Other versions
WO2012035549A2 (en
Inventor
Rajesh Jain
Jagadeeshwar R Rao
Siripragada Mahender Rao
Original Assignee
Panacea Biotec 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 Panacea Biotec Ltd filed Critical Panacea Biotec Ltd
Publication of WO2012035549A2 publication Critical patent/WO2012035549A2/en
Publication of WO2012035549A3 publication Critical patent/WO2012035549A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • 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
    • C07D243/10—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 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • 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

Landscapes

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

Abstract

The present invention is related to an improved process and intermediate(s) for the synthesis of beta amino acid derivatives of formula (I). The compounds of formula I act as DPP-IV inhibitors and are useful in the treatment of Type 2 diabetes.
PCT/IN2011/000621 2010-09-13 2011-09-12 An improved process for the synthesis of beta amino acid derivatives WO2012035549A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2164/DEL/2010 2010-09-13
IN2164DE2010 IN2010DE02164A (en) 2010-09-13 2011-09-12

Publications (2)

Publication Number Publication Date
WO2012035549A2 WO2012035549A2 (en) 2012-03-22
WO2012035549A3 true WO2012035549A3 (en) 2012-10-11

Family

ID=44898127

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2011/000621 WO2012035549A2 (en) 2010-09-13 2011-09-12 An improved process for the synthesis of beta amino acid derivatives

Country Status (3)

Country Link
AR (1) AR082971A1 (en)
IN (1) IN2010DE02164A (en)
WO (1) WO2012035549A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015145333A1 (en) 2014-03-26 2015-10-01 Sun Pharmaceutical Industries Limited Process for the preparation of sitagliptin and its intermediate

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004058266A1 (en) * 2002-12-20 2004-07-15 Merck & Co., Inc. 3-amino-4-phenylbutanoic acid derivatives as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes
WO2006104997A2 (en) * 2005-03-29 2006-10-05 Merck & Co., Inc. Tartaric acid salts of a dipeptidyl peptidase-iv inhibitor
WO2009093269A1 (en) * 2008-01-24 2009-07-30 Panacea Biotec Limited Novel heterocyclic compounds
WO2010097420A1 (en) * 2009-02-25 2010-09-02 Esteve Química, S.A. Process for the preparation of a chiral beta aminoacid derivative and intermediates thereof

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP1554256B1 (en) 2002-07-15 2009-12-09 Merck & Co., Inc. Piperidino pyrimidine dipeptidyl peptidase inhibitors for the treatment of diabetes
AU2003298596B2 (en) 2002-10-18 2008-12-18 Merck Sharp & Dohme Corp. Beta-amino heterocyclic dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes
AU2003290577B2 (en) 2002-11-07 2008-12-11 Merck Sharp & Dohme Corp. Phenylalanine derivatives as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes
AR043515A1 (en) 2003-03-19 2005-08-03 Merck & Co Inc PROCEDURE TO PREPARE CHIRAL DERIVATIVES BETA AMINO ACIDS BY ASYMMETRIC HYDROGENATION
EP1651623B1 (en) 2003-07-31 2008-12-17 Merck & Co., Inc. Hexahydrodiazepinones as dipeptidyl peptidase-iv inhibitors for the treatment or prevention of diabetes
GB0324236D0 (en) 2003-10-16 2003-11-19 Astrazeneca Ab Chemical compounds
US7238683B2 (en) 2003-11-04 2007-07-03 Merck & Co., Inc. Fused phenylalanine derivatives as dipeptidyl peptidase-iv inhibitors for the treatment or prevention of diabetes
US7671073B2 (en) 2004-05-18 2010-03-02 Merck Sharp & Dohme Corp. Cyclohexylalanine derivatives as dipeptidyl peptidase-IV inhibitors for the treatment or prevention of diabetes
EP1598341A1 (en) 2004-05-21 2005-11-23 Santhera Pharmaceuticals (Deutschland) Aktiengesellschaft DPP-IV inhibitors
EP1604662A1 (en) 2004-06-08 2005-12-14 Santhera Pharmaceuticals (Deutschland) Aktiengesellschaft 1-[(3R)-Amino-4-(2-fluoro-phenyl)-butyl]-pyrrolidine-(2R)-carboxylic acid benzyl amine derivatives and related compounds as dipeptidyl peptidase IV (DPP-IV) inhibitors for the treatment of type 2 diabetes mellitus
EP1604989A1 (en) 2004-06-08 2005-12-14 Santhera Pharmaceuticals (Deutschland) Aktiengesellschaft DPP-IV inhibitors
GB0413389D0 (en) 2004-06-16 2004-07-21 Astrazeneca Ab Chemical compounds
CA2570807C (en) 2004-06-21 2011-12-06 Merck & Co., Inc. Aminocyclohexanes as dipeptidyl peptidase-iv inhibitors for the treatment or prevention of diabetes
DE602005022320D1 (en) 2004-08-23 2010-08-26 Merck Sharp & Dohme CONDENSED TRIAZOLE DERIVATIVES AS DIPEPTIDYLPEPTIDASE IV HEMMER FOR TREATMENT OR PREVENTION OF DIABETES
US7884104B2 (en) 2004-10-01 2011-02-08 Merck Sharp & Dohme Corp. Aminopiperidines as dipeptidyl peptidase-IV inhibitors for the treatment or prevention of diabetes
AR052879A1 (en) 2005-01-24 2007-04-11 Merck & Co Inc PROCEDURE TO PREPARE BETA DERIVATIVES CHIRAL AMINO ACIDS BY ASYMMETRIC HYDROGENATION
EP1702916A1 (en) 2005-03-18 2006-09-20 Santhera Pharmaceuticals (Schweiz) GmbH DPP-IV inhibitors
EP2487154B1 (en) 2005-10-31 2013-10-16 Bristol-Myers Squibb Company Pyrrolidinyl beta-amino amide-based inhibitors of dipeptidyl peptidase IV and methods
WO2007054577A1 (en) 2005-11-14 2007-05-18 Probiodrug Ag Cyclopropyl-fused pyrrolidine derivatives as dipeptidyl peptidase iv inhibitors
WO2007063928A1 (en) 2005-11-30 2007-06-07 Toray Industries, Inc. Novel noncyclic amine carboxamide derivative and salt thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004058266A1 (en) * 2002-12-20 2004-07-15 Merck & Co., Inc. 3-amino-4-phenylbutanoic acid derivatives as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes
WO2006104997A2 (en) * 2005-03-29 2006-10-05 Merck & Co., Inc. Tartaric acid salts of a dipeptidyl peptidase-iv inhibitor
WO2009093269A1 (en) * 2008-01-24 2009-07-30 Panacea Biotec Limited Novel heterocyclic compounds
WO2010097420A1 (en) * 2009-02-25 2010-09-02 Esteve Química, S.A. Process for the preparation of a chiral beta aminoacid derivative and intermediates thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
KIM DOOSEOP ET AL: "(2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]py razin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine: a potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 48, no. 1, 13 January 2005 (2005-01-13), pages 141 - 151, XP002557878, ISSN: 0022-2623, [retrieved on 20041213], DOI: 10.1021/JM0493156 *
KIM ET AL: "Triazolopiperazine-amides as dipeptidyl peptidase IV inhibitors: Close analogs of JANUVIA(TM) (sitagliptin phosphate)", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB, vol. 17, no. 12, 15 June 2007 (2007-06-15), pages 3373 - 3377, XP022097786, ISSN: 0960-894X, DOI: 10.1016/J.BMCL.2007.03.098 *
ROLF PAUL ET AL: "N,N'-Carbonyldiimidazole, a new peptide forming reagent", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC; US, vol. 82, no. 5, 1 January 1960 (1960-01-01), pages 4596 - 4600, XP002202500, ISSN: 0002-7863, DOI: 10.1021/JA01502A038 *

Also Published As

Publication number Publication date
IN2010DE02164A (en) 2015-07-24
AR082971A1 (en) 2013-01-23
WO2012035549A2 (en) 2012-03-22

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