WO2013111158A3 - Procédé de préparation d'inhibiteur dpp-iv - Google Patents

Procédé de préparation d'inhibiteur dpp-iv Download PDF

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Publication number
WO2013111158A3
WO2013111158A3 PCT/IN2013/000003 IN2013000003W WO2013111158A3 WO 2013111158 A3 WO2013111158 A3 WO 2013111158A3 IN 2013000003 W IN2013000003 W IN 2013000003W WO 2013111158 A3 WO2013111158 A3 WO 2013111158A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
dpp
inhibitor
hydroxyadamantan
azabicyclo
Prior art date
Application number
PCT/IN2013/000003
Other languages
English (en)
Other versions
WO2013111158A2 (fr
Inventor
Srinivasan Thirumalai Rajan
Sajja Eswaraiah
Ghojala Venkat Reddy
Original Assignee
Msn Laboratories Limited
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 Msn Laboratories Limited filed Critical Msn Laboratories Limited
Publication of WO2013111158A2 publication Critical patent/WO2013111158A2/fr
Publication of WO2013111158A3 publication Critical patent/WO2013111158A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/26—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing carboxyl groups by reaction with HCN, or a salt thereof, and amines, or from aminonitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
    • 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
    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
    • 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
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

La présente invention concerne un procédé de préparation de (l S, 3S, 5S)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-l-yl)acétyl]-2-azabicyclo [3.1.0] hexane-3-carbonitrile représenté par le composé de formule 1, et ses sels pharmaceutiquement acceptables.
PCT/IN2013/000003 2012-01-03 2013-01-02 Procédé de préparation d'inhibiteur dpp-iv WO2013111158A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN32CH2012 2012-01-03
IN32/CHE/2012 2012-01-03
IN1259/CHE/2012 2012-03-30
IN1259CH2012 2012-03-30

Publications (2)

Publication Number Publication Date
WO2013111158A2 WO2013111158A2 (fr) 2013-08-01
WO2013111158A3 true WO2013111158A3 (fr) 2013-11-28

Family

ID=48874029

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2013/000003 WO2013111158A2 (fr) 2012-01-03 2013-01-02 Procédé de préparation d'inhibiteur dpp-iv

Country Status (1)

Country Link
WO (1) WO2013111158A2 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104341320A (zh) * 2013-08-09 2015-02-11 苏州景泓生物技术有限公司 沙格列汀关键中间体ⅷ的制备方法
WO2015087262A1 (fr) 2013-12-11 2015-06-18 Ranbaxy Laboratories Limited Procédé pour la préparation de saxagliptine et de ses intermédiaires
CN105315189A (zh) * 2014-05-29 2016-02-10 上海医药工业研究院 一种制备（5s）-5-氨基羰基-4,5-二氢-1h-吡咯-1-羧酸-1（1,1-二甲基乙基）酯的方法
CN104557582A (zh) * 2015-01-04 2015-04-29 浙江工业大学 一种沙格列汀中间体的制备方法
CN105037245B (zh) * 2015-08-03 2017-04-12 沧州那瑞化学科技有限公司 一种沙格列汀中间体的制备方法
BR112023006761A2 (pt) * 2021-04-16 2024-02-06 Fujian Akeylink Biotechnology Co Ltd Compostos de peptídeo curto de prolina modificado no anel, composição farmacêutica e uso dos mesmos
CN113666846B (zh) * 2021-08-31 2023-06-27 济南立德医药技术有限公司 沙格列汀中间体的合成方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5464796A (en) * 1991-06-22 1995-11-07 Bayer Aktiengesellschaft 7-isoindolinyl-quinolone-carboxylic acid derivatives
WO2002102784A2 (fr) * 2001-06-15 2002-12-27 Ekaterini Antoniadou-Vyza Series de 4,6-diamino-1,2-dihydro-1-aryl-1,3,5-triazines, substituees par un fragment adamantyle en position 2 de la triazine, leurs sels, isomeres, stereoisomeres, enantioneres, bases libres correspondants, et complexes de tous les composes precites avec des macromolecules naturelles et leurs derives synthetiques
WO2004037181A2 (fr) * 2002-10-23 2004-05-06 Bristol-Myers Squibb Company Inhibiteurs de dipeptidyl peptidase iv a base de glycinenitrile et procedes correspondants
WO2005012249A2 (fr) * 2003-08-01 2005-02-10 Bristol-Myers Squibb Company Inhibiteurs a base d'adamantyglycine de la dipeptidyl peptidase iv et procedes associes
CN1958545A (zh) * 2006-07-20 2007-05-09 浙江师范大学 用金刚烷甲类酸制备金刚烷甲醇的方法
WO2010113042A1 (fr) * 2009-04-03 2010-10-07 Universiteit Leiden Peptides cycliques antimicrobiens

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5464796A (en) * 1991-06-22 1995-11-07 Bayer Aktiengesellschaft 7-isoindolinyl-quinolone-carboxylic acid derivatives
WO2002102784A2 (fr) * 2001-06-15 2002-12-27 Ekaterini Antoniadou-Vyza Series de 4,6-diamino-1,2-dihydro-1-aryl-1,3,5-triazines, substituees par un fragment adamantyle en position 2 de la triazine, leurs sels, isomeres, stereoisomeres, enantioneres, bases libres correspondants, et complexes de tous les composes precites avec des macromolecules naturelles et leurs derives synthetiques
WO2004037181A2 (fr) * 2002-10-23 2004-05-06 Bristol-Myers Squibb Company Inhibiteurs de dipeptidyl peptidase iv a base de glycinenitrile et procedes correspondants
WO2005012249A2 (fr) * 2003-08-01 2005-02-10 Bristol-Myers Squibb Company Inhibiteurs a base d'adamantyglycine de la dipeptidyl peptidase iv et procedes associes
CN1958545A (zh) * 2006-07-20 2007-05-09 浙江师范大学 用金刚烷甲类酸制备金刚烷甲醇的方法
WO2010113042A1 (fr) * 2009-04-03 2010-10-07 Universiteit Leiden Peptides cycliques antimicrobiens

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BOOTH, RAYMOND G ET AL.: "Quantitative Structure-Activity Relationship of Triazine-Antifolate Inhibition of Leishmania Dihydrofolate Reductase and Cell Growth", J. MED. CHEM., vol. 30, no. 7, 1987, pages 1218 - 1224 *
MCGEARY, ROSS P.: "Facile and Chemoselective Reduction of Carboxylic Acids to Alcohols Using BOP Reagent and Sodium Borohydride", TETRAHEDRON LETTERS, vol. 39, no. 20, 1998, pages 3319 - 3322 *

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WO2013111158A2 (fr) 2013-08-01

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