CA2759077C - Sitagliptin synthesis - Google Patents

Sitagliptin synthesis Download PDF

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Publication number
CA2759077C
CA2759077C CA2759077A CA2759077A CA2759077C CA 2759077 C CA2759077 C CA 2759077C CA 2759077 A CA2759077 A CA 2759077A CA 2759077 A CA2759077 A CA 2759077A CA 2759077 C CA2759077 C CA 2759077C
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CA
Canada
Prior art keywords
acid
process according
amino
derivative
enantiomerically enriched
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
CA2759077A
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English (en)
French (fr)
Other versions
CA2759077A1 (en
Inventor
Vinayak Govind Gore
Maheshkumar Gadakar
Priyanka Bhosle
Suresh Shinde
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Generics UK Ltd
Original Assignee
Generics UK 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 Generics UK Ltd filed Critical Generics UK Ltd
Publication of CA2759077A1 publication Critical patent/CA2759077A1/en
Application granted granted Critical
Publication of CA2759077C publication Critical patent/CA2759077C/en
Active legal-status Critical Current
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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
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • A61P3/06—Antihyperlipidemics
    • 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
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • 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

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Diabetes (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2759077A 2009-05-11 2010-05-10 Sitagliptin synthesis Active CA2759077C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN722/KOL/2009 2009-05-11
IN722KO2009 2009-05-11
PCT/GB2010/050760 WO2010131025A1 (en) 2009-05-11 2010-05-10 Sitagliptin synthesis

Publications (2)

Publication Number Publication Date
CA2759077A1 CA2759077A1 (en) 2010-11-18
CA2759077C true CA2759077C (en) 2016-02-16

Family

ID=42312921

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2759077A Active CA2759077C (en) 2009-05-11 2010-05-10 Sitagliptin synthesis

Country Status (8)

Country Link
US (1) US8846916B2 (enExample)
EP (1) EP2430025A1 (enExample)
JP (2) JP6199556B2 (enExample)
CN (1) CN102574856B (enExample)
AU (1) AU2010247193B2 (enExample)
CA (1) CA2759077C (enExample)
NZ (1) NZ596713A (enExample)
WO (1) WO2010131025A1 (enExample)

Families Citing this family (32)

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EP2508506A1 (en) 2011-04-08 2012-10-10 LEK Pharmaceuticals d.d. Preparation of sitagliptin intermediates
CN102757431B (zh) * 2011-04-24 2016-03-30 浙江华海药业股份有限公司 一种合成西他列汀的新方法
CA2840814A1 (en) 2011-06-29 2013-01-03 Ranbaxy Laboratories Limited Solid dispersions of sitagliptin and processes for their preparation
US20150051213A1 (en) 2011-06-30 2015-02-19 Suresh Babu Jayachandra Novel salts of sitagliptin
WO2013013833A1 (en) 2011-07-27 2013-01-31 Farma Grs, D.O.O. Process for the preparation of sitagliptin and its pharmaceutically acceptable salts
CN102603749B (zh) * 2011-10-27 2017-02-08 浙江华海药业股份有限公司 一种西他列汀中间体的合成方法
EP2788352A1 (en) 2011-12-08 2014-10-15 Ranbaxy Laboratories Limited Amorphous form of sitagliptin salts
CN102531937A (zh) * 2011-12-31 2012-07-04 浙江工业大学 一种化学拆分法制备(r)-3-氨基-4-(2,4,5-三氟苯基)丁酸甲酯的方法
WO2013114173A1 (en) * 2012-01-30 2013-08-08 Smilax Laboratories Limited A novel process for the preparation of sitagliptin
CN102702205B (zh) * 2012-05-16 2014-01-15 苏州新凯生物医药技术有限公司 西他列汀的制备方法
EP2674432A1 (en) 2012-06-14 2013-12-18 LEK Pharmaceuticals d.d. New synthetic route for the preparation of ß aminobutyryl substituted 5,6,7,8-tetrahydro[1,4]diazolo[4,3-alpha]pyrazin-7-yl compounds
KR102157917B1 (ko) * 2012-12-21 2020-09-21 레크 파마슈티칼스 디.디. 키랄 γ-아릴-β-아미노부티르산 유도체의 제조를 위한 효소 경로
IN2013MU00916A (enExample) * 2013-03-20 2015-06-26 Cadila Healthcare Ltd
CN103497145B (zh) * 2013-10-10 2016-01-27 南昌大学 一种光学纯多奈哌齐的制备工艺
IN2014MU00212A (enExample) * 2014-01-21 2015-08-28 Cadila Healthcare Ltd
CN104557944B (zh) * 2014-12-31 2017-05-31 北京瑞都医药科技有限公司 一种降糖药物及其制备方法
CN105331651B (zh) * 2015-11-25 2018-11-13 尚科生物医药（上海）有限公司 西他列汀及其中间体的酶-化学制备方法
CN105294479B (zh) * 2015-12-05 2017-09-22 新发药业有限公司 一种3r‑氨基取代丁酰胺衍生物的制备方法
JP6049923B1 (ja) 2016-02-18 2016-12-21 三菱日立パワーシステムズ株式会社 部品情報検索装置、部品情報検索方法、およびプログラム
CN107129501B (zh) * 2017-05-19 2019-05-21 贵州大学 2型糖尿病药物西他列汀制备新方法
CN107669683B (zh) * 2017-09-30 2020-07-03 杭州华东医药集团新药研究院有限公司 含有西格列汀与二甲双胍的药物组合物
CN108586346B (zh) 2018-05-10 2019-10-01 北京富盛嘉华医药科技有限公司 一种生物催化合成西他列汀及其中间体的方法
CN110759914A (zh) * 2019-02-03 2020-02-07 美华东进国际生物医药研究院有限公司 一种治疗糖尿病的药物的制备方法
CN112300017B (zh) * 2019-08-01 2023-06-09 浙江九洲药业股份有限公司 一种手性β-氨基酸及其衍生物的消旋制备方法
CN112341332B (zh) * 2020-11-11 2023-04-28 浙江昌明药业有限公司 一种西他列汀关键中间体降解废弃物的回收利用方法
CN114644568B (zh) * 2020-12-21 2024-07-19 浙江医药股份有限公司新昌制药厂 西格列汀中间体的纯化方法
CN113045448A (zh) * 2021-03-09 2021-06-29 台州市生物医化产业研究院有限公司 一种乙酰麦氏酸衍生物降解废弃物的回收利用方法
CN115583935A (zh) * 2022-11-03 2023-01-10 浙江工业大学 一种4-(2,4,5-三氟苯基)-3-氧丁酸酯的制备方法
EP4630568A1 (en) 2022-12-09 2025-10-15 KRKA, D.D., Novo Mesto Process for the preparation of sitagliptin
CN115819258B (zh) * 2022-12-13 2024-10-18 浙江大学 一种利用含膦氧双键催化剂的西格列汀中间体的制备方法
CN115960007B (zh) * 2022-12-13 2025-02-07 浙江大学 一种利用含氮甲酰基催化剂的西格列汀中间体的制备方法
CN117069604A (zh) * 2023-08-22 2023-11-17 河北龙海药业有限公司 一种磷酸西格列汀杂质fp-e的制备方法及其检测方法

Family Cites Families (18)

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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
AR043515A1 (es) 2003-03-19 2005-08-03 Merck & Co Inc Procedimiento para preparar derivados quirales beta aminoacidos mediante hidrogenacion asimetrica
WO2004085661A2 (en) 2003-03-24 2004-10-07 Merck & Co., Inc Process to chiral beta-amino acid derivatives
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
JO2625B1 (en) 2003-06-24 2011-11-01 ميرك شارب اند دوم كوربوريشن Phosphoric acid salts of dipeptidyl betidase inhibitor 4
US20060287528A1 (en) 2003-09-02 2006-12-21 Wenslow Robert M Novel crystalline forms of a phosphoric acid salt of a dipeptidyl peptidase-iv inhibitor
WO2005030127A2 (en) 2003-09-23 2005-04-07 Merck & Co., Inc. Novel crystalline form of a phosphoric acid salt of a dipeptidyl peptidase-iv inhibitor
EP1796671A4 (en) 2004-09-15 2009-01-21 Merck & Co Inc AMORPHIC FORM OF A PHOSPHORIC ACID SALT OF A DIPEPTIDYL-PEPTIDASE IV HEMMER
WO2006065826A2 (en) * 2004-12-15 2006-06-22 Merck & Co., Inc. Process to chiral beta amino acid derivatives by asymmetric hydrogenation
US8334385B2 (en) * 2007-11-02 2012-12-18 Glenmark Generics Limited Process for the preparation of R-sitagliptin and its pharmaceutically acceptable salts thereof
WO2009064476A1 (en) 2007-11-13 2009-05-22 Teva Pharmaceutical Industries Ltd. Preparation of sitagliptin intermediate
KR20100101073A (ko) 2007-12-20 2010-09-16 닥터 레디스 레보러터리즈 리미티드 시타글립틴 및 약제학적으로 허용되는 그의 염의 제조 방법
US20090247532A1 (en) 2008-03-28 2009-10-01 Mae De Ltd. Crystalline polymorph of sitagliptin phosphate and its preparation
CN101633625B (zh) 2008-07-23 2013-02-13 江苏恒瑞医药股份有限公司 R-β-氨基苯丁酸衍生物的制备方法
WO2010032264A2 (en) 2008-08-27 2010-03-25 Cadila Healthcare Limited Improved process for preparation of (2r)-4-oxo-4-[3- (trifluoromethyl)-5,6-dihydro [1,2,4]-triazolo[4,3-a]pyrazin- 7(8h)-yl]-l-(2,4,5-trifluorophenyl)butan-2-amine & new impurities in preparation thereof
WO2010078440A1 (en) * 2008-12-31 2010-07-08 Chiral Quest, Inc. Process and intermediates for the preparation of n-acylated-4-aryl beta-amino acid derivatives
WO2010131035A1 (en) 2009-05-11 2010-11-18 Generics [Uk] Limited Novel crystalline polymorph of sitagliptin dihydrogen phosphate
CN101928289A (zh) * 2009-06-19 2010-12-29 北京海步国际医药科技发展有限公司 制备二肽基肽酶-iv抑制剂的方法

Also Published As

Publication number Publication date
JP2016029051A (ja) 2016-03-03
JP6199556B2 (ja) 2017-09-20
AU2010247193A1 (en) 2011-12-08
US8846916B2 (en) 2014-09-30
CN102574856A (zh) 2012-07-11
EP2430025A1 (en) 2012-03-21
US20120108598A1 (en) 2012-05-03
NZ596713A (en) 2014-10-31
AU2010247193B2 (en) 2016-05-19
JP2012526791A (ja) 2012-11-01
CA2759077A1 (en) 2010-11-18
WO2010131025A1 (en) 2010-11-18
CN102574856B (zh) 2016-09-21

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