WO2010022690A3 - Méthode de préparation de vildagliptine extrêmement pure - Google Patents

Méthode de préparation de vildagliptine extrêmement pure Download PDF

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Publication number
WO2010022690A3
WO2010022690A3 PCT/CZ2009/000105 CZ2009000105W WO2010022690A3 WO 2010022690 A3 WO2010022690 A3 WO 2010022690A3 CZ 2009000105 W CZ2009000105 W CZ 2009000105W WO 2010022690 A3 WO2010022690 A3 WO 2010022690A3
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WO
WIPO (PCT)
Prior art keywords
preparation
vildagliptin
highly pure
stands
chlorine
Prior art date
Application number
PCT/CZ2009/000105
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English (en)
Other versions
WO2010022690A2 (fr
Inventor
Ales Halama
Bozena Kafkova
Tomas Chvojka
Original Assignee
Zentiva, K.S.
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.)
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Publication date
Application filed by Zentiva, K.S. filed Critical Zentiva, K.S.
Publication of WO2010022690A2 publication Critical patent/WO2010022690A2/fr
Publication of WO2010022690A3 publication Critical patent/WO2010022690A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Diabetes (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Endocrinology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (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)
  • Pyrrole Compounds (AREA)

Abstract

Cette invention concerne une nouvelle méthode de préparation de vildagliptine extrêmement pure du point de vue chimique et utilisable du point de vue pharmaceutique (I), ladite méthode comprenant le contrôle analytique du processus de production et de la qualité de la substance cible. Le nouveau procédé repose sur la préparation et l’isolation d’un mélange constitué de l-haloacétyl-2-(S)-pyrrolidine carboxamide de formule chimique (VI), X étant un atome de chlore ou de brome, et d’hydrohalogénures de trialkylamine de formule chimique R1R2R3N*HX, R1, R2 et R3 étant indépendamment un alkyle linéaire ou ramifié ayant de 1 à 6 atomes de carbone, les substituants R1 et R2 pouvant être reliés par un pont et formant un cycle comportant 2 à 6 atomes de carbone, ou pouvant être liés avec une liaison éther, X étant un atome de chlore ou de brome. L’invention concerne également des normes analytiques et des méthodes analytiques utilisées pour contrôler le processus de production et la qualité finale de la vildagliptine.
PCT/CZ2009/000105 2008-08-26 2009-08-25 Méthode de préparation de vildagliptine extrêmement pure WO2010022690A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CZ20080512A CZ2008512A3 (cs) 2008-08-26 2008-08-26 Zpusob prípravy vysoce cistého vildagliptinu
CZPV2008-512 2008-08-26

Publications (2)

Publication Number Publication Date
WO2010022690A2 WO2010022690A2 (fr) 2010-03-04
WO2010022690A3 true WO2010022690A3 (fr) 2010-11-11

Family

ID=41721993

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CZ2009/000105 WO2010022690A2 (fr) 2008-08-26 2009-08-25 Méthode de préparation de vildagliptine extrêmement pure

Country Status (2)

Country Link
CZ (1) CZ2008512A3 (fr)
WO (1) WO2010022690A2 (fr)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
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IT1400714B1 (it) 2010-07-06 2013-06-28 Chemelectiva S R L Processo ed intermedi per la preparazione di un principio attivo.
HU231050B1 (hu) 2010-08-19 2020-02-28 Egis Gyógyszergyár Nyrt. Eljárás gyógyszerhatóanyag előállítására
ITMI20112224A1 (it) 2011-12-06 2013-06-07 Chemelectiva S R L Nuovo processo ed intermedi per la sintesi di vildagliptin
CN102617434B (zh) * 2012-03-29 2014-07-23 中国科学院上海有机化学研究所 一锅法制备维达列汀
WO2013179300A2 (fr) 2012-05-04 2013-12-05 Megafine Pharma (P) Ltd. Procédé de préparation de vildagliptine et de son intermédiaire
CN103787944A (zh) * 2012-11-01 2014-05-14 天津药物研究院 1-(2-氯乙酰基)-2-(s)-腈基吡咯烷的制备方法
CN103351320A (zh) * 2013-06-17 2013-10-16 张家港威胜生物医药有限公司 一种制备(s)-1-(2-氯乙酰基)-吡咯烷-2-甲酰胺的方法
WO2015092806A1 (fr) * 2013-12-18 2015-06-25 Harman Finochem Limited Procédé économique et avancé pour la préparation de vildagliptine pure
CN103804267B (zh) * 2014-02-21 2016-06-08 张家港威胜生物医药有限公司 一种维达列汀的合成工艺
WO2015145467A1 (fr) * 2014-03-28 2015-10-01 Laurus Labs Private Limited Procédé amélioré de préparation de vildagliptine
CN105884669B (zh) * 2014-09-15 2020-05-15 深圳翰宇药业股份有限公司 制备取代的(s)-吡咯烷-2-甲腈及维格列汀的方法
CN104744334A (zh) * 2015-03-25 2015-07-01 合肥创新医药技术有限公司 维格列汀的制备方法
CN104945299B (zh) * 2015-05-28 2017-03-15 烟台万润药业有限公司 一种维格列汀的高效合成方法
CN105153165B (zh) * 2015-07-30 2017-08-29 上海医药集团青岛国风药业股份有限公司 一种维格列汀杂质的制备方法
CN105085360A (zh) * 2015-09-10 2015-11-25 南京理工大学 一种高纯度维格列汀的制备方法
CN107219307A (zh) * 2016-03-22 2017-09-29 中美华世通生物医药科技（武汉）有限公司 利用hplc测定曲格列汀原料药及其制剂中对映异构体杂质的方法
CN106338564B (zh) * 2016-09-27 2018-10-12 海口南陆医药科技股份有限公司 一种用于检测维格列汀中间体中对映异构体的方法
CN107311907A (zh) * 2017-07-29 2017-11-03 合肥创新医药技术有限公司 一种维格列汀异构体杂质的制备方法
CN109827984B (zh) * 2019-02-27 2022-05-17 南京江北新区生物医药公共服务平台有限公司 一种测定l-脯氨酰胺合成工艺杂质或其结构类似物对照品含量的方法
WO2021116897A1 (fr) * 2019-12-10 2021-06-17 Optimus Drugs (P) Ltd Procédé de préparation de vildagliptine
CN110940759B (zh) * 2019-12-23 2022-05-03 河北科技大学 一种维格列汀中间体-5的hplc检测方法
WO2022003405A1 (fr) 2020-07-03 2022-01-06 Savoi Guilherme Procédé monotope permettant d'obtenir un composé intermédiaire pyrrolidine-2-carbonitrile et procédé télescopique à l'échelle industrielle permettant de préparer du (2s)-1-[n-(3-hydroxyadamantan-1-yl)glycyl]-2-pyrrolidinecarbonitrile (vildagliptine) l'utilisant
CN112394127B (zh) * 2020-12-08 2022-05-10 海南通用三洋药业有限公司 一种测定维格列汀中3-氨基-1-金刚烷醇和l-脯氨酰胺含量的方法
CN112557582B (zh) * 2020-12-17 2022-11-01 南通恒华粘合材料科技有限公司 一种聚酯多元醇羟值测定的方法
CN112939837B (zh) * 2021-02-03 2022-07-19 海南通用三洋药业有限公司 一种多相复式连续生产制备维格列汀的方法
CN114814050A (zh) * 2022-03-29 2022-07-29 浙江美诺华药物化学有限公司 一种3-氨基-1-金刚烷醇的杂质检测方法

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KR20080031936A (ko) 2005-08-04 2008-04-11 노파르티스 아게 빌다글립틴의 염

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EP1137635B1 (fr) * 1998-12-10 2005-10-19 Novartis AG 2-cyanopyrrolidines n-substitues
WO2001096295A2 (fr) * 2000-06-13 2001-12-20 Novartis Ag Composes organiques
WO2003051848A2 (fr) * 2001-12-14 2003-06-26 Ferring Bv Derives d'acide imidazolidine acetique
EP1595866A1 (fr) * 2003-01-31 2005-11-16 Sanwa Kagaku Kenkyusho Co., Ltd. Compos inhibant la dipeptidyl peptidase iv
WO2004092127A1 (fr) * 2003-04-16 2004-10-28 Novartis Ag Procede de preparation de 2-cyanopyrrolidines n-substituees
WO2006100181A2 (fr) * 2005-03-22 2006-09-28 F. Hoffmann-La Roche Ag Nouveau sel et polymorphes de l'inhibiteur de dpp-iv
WO2008084383A2 (fr) * 2007-01-10 2008-07-17 Medichem, S.A. Procédé de préparation de la vildagliptine
WO2009058531A1 (fr) * 2007-10-31 2009-05-07 Exxonmobil Chemical Patents Inc. Oxydation d'hydrocarbures

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MCINTYRE J A ET AL: "Vildagliptin. Agent for type 2 diabetes, dipeptidyl-peptidase IV inhibitor", DRUGS OF THE FUTURE, PROUS SCIENCE, ES LNKD- DOI:10.1358/DOF.2004.029.09.841366, vol. 29, no. 9, 1 September 2004 (2004-09-01), pages 887 - 891, XP002483135, ISSN: 0377-8282 *
VILLHAUER E B ET AL: "1-Ä2-Ä(5-CYANOPYRIDIN-2-YL)AMINOÜ-ETHYLAMINOÜACETYL-2-(S)-PYRROLIDINE CARBONITRILE: A POTENT, SELECTIVE, AND ORALLY BIOAVAILABLE DIPEPTIDYL PEPTIDASE IV INHIBITOR WITH ANTIHYPERGLYCEMIC PROPERTIES", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US LNKD- DOI:10.1021/JM025522Z, vol. 45, no. 12, 6 June 2002 (2002-06-06), pages 2362 - 2365, XP001165748, ISSN: 0022-2623 *
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WO2010022690A2 (fr) 2010-03-04
CZ2008512A3 (cs) 2010-03-10

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