AR080670A1 - Metodo de produccion de derivados de acido glutamico marcados con f-18 - Google Patents

Metodo de produccion de derivados de acido glutamico marcados con f-18

Info

Publication number
AR080670A1
AR080670A1 ARP100104235A ARP100104235A AR080670A1 AR 080670 A1 AR080670 A1 AR 080670A1 AR P100104235 A ARP100104235 A AR P100104235A AR P100104235 A ARP100104235 A AR P100104235A AR 080670 A1 AR080670 A1 AR 080670A1
Authority
AR
Argentina
Prior art keywords
formula
tert
compound
group
butoxycarbonyl
Prior art date
Application number
ARP100104235A
Other languages
English (en)
Inventor
Matthias Friebe
Keith Graham
Thomas Brumby
Christina Hultsch
Hans-Jurgen Wester
Franziska Wagner
Mathias Berndt
Heribert Schmitt-Willich
Original Assignee
Bayer Schering Pharma Ag
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 Bayer Schering Pharma Ag filed Critical Bayer Schering Pharma Ag
Publication of AR080670A1 publication Critical patent/AR080670A1/es

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/38Separation; Purification; Stabilisation; Use of additives
    • C07C227/40Separation; Purification
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • C07C227/20Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters by hydrolysis of N-acylated amino-acids or derivatives thereof, e.g. hydrolysis of carbamates
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04Organic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04Organic compounds
    • A61K51/0402Organic compounds carboxylic acid carriers, fatty acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04Organic compounds
    • A61K51/0404Lipids, e.g. triglycerides; Polycationic carriers
    • A61K51/0406Amines, polyamines, e.g. spermine, spermidine, amino acids, (bis)guanidines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/001Acyclic or carbocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/30Preparation of optical isomers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02Compounds 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
    • C07C229/04Compounds 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 being acyclic and saturated
    • C07C229/24Compounds 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 being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06Esters of carbamic acids
    • C07C271/08Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63Esters of sulfonic acids
    • C07C309/64Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66Methanesulfonates
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63Esters of sulfonic acids
    • C07C309/72Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05Isotopically modified compounds, e.g. labelled

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Indole Compounds (AREA)

Abstract

Métodos que permiten obtener derivados de ácido glutámico marcados con F-18. Reivindicacion 1: Un método para producir un compuesto de la formula (1), caracterizado porque comprende los pasos de: Paso 1: Síntesis de un compuesto de la formula (3) radiomarcado por reaccion de un compuesto de la formula (2) con un agente de fluoracion con F-18; Paso 2: Clivaje de los grupos protectores del compuesto de la formula (3) para obtener un compuesto de la formula (1); Paso 3: Purificacion y formulacion de un compuesto de la formula (1), en donde: X se selecciona del grupo que comprende: a) un enlace, b) alquilo C2-10 ramificado o no ramificado, c) alcoxi C2-10 ramificado o no ramificado, d) alquenilo C3-10 ramificado o no ramificado, e) alquinilo C3-10 ramificado o no ramificado, f) [(CH2)n-O]m-(CH2)o y g) O-[(CH2)n-O]m-(CH2)o; n = 2 - 6, preferentemente n = 2 o 3; m = 1 - 3, preferentemente m = 1 o 2; o = 2 - 6, preferentemente o = 2 o 3; R1 y R2 son grupos protectores de carboxilo y en donde el grupo protector de carboxilo se selecciona, de manera independiente entre sí, entre a) alquilo C1-6 ramificado o no ramificado, b) bencilo y c) alquilo; R3 y R4 se seleccionan, de manera independiente entre sí, del grupo que comprende: a) hidrogeno, b) un grupo protector de amina o c) el grupo NR3R4 es un grupo 1,3-dioxo-1,3-dihidro-2H-isoindol-2-ilo (ftalimido) o un grupo azida; y que abarca isomeros individuales, tautomeros, diastereomeros, enantiomeros, mezclas del mismo y sales adecuadas del mismo. Reivindicacion 9: El método de acuerdo con las reivindicaciones 1 a 6 caracterizado porque el compuesto de formula (2) se selecciona entre el grupo que comprende: (2S,4S)-N-(tert-butoxicarbonil)-4-[3-(mesiloxi)propil]-glutamato de di-tert-butilo de formula (4), (2S,4S)-N-(tert-butoxicarbonil)-4-[3-(tosiloxi)propil]-glutamato de di-tert-butilo de formula (5), (2S,4S)-N-(tert-butoxicarbonil)-4-(3-{[(4-nitrofenil)-sulfonil]oxi}propil)-glutamato de di-tert-butilo de formula (6), (2S,4R)-N-(tert-butoxicarbonil)-4-[3-(mesiloxil)propil]-glutamato de di-tert-butilo de formula (7), (2S,4R)-N-(tert-butoxicarbonil)-4-[3-(tosiloxi)propil]-glutamato de di-tert-butilo de formula (8), o (2S,4R)-N-(tert-butoxicarbonil)-4-(3-{[(4-nitrofenil)-sulfonil]oxi}propil)-glutamato de di-tert-butilo de formula (9).
ARP100104235A 2009-11-17 2010-11-17 Metodo de produccion de derivados de acido glutamico marcados con f-18 AR080670A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP09075508 2009-11-17

Publications (1)

Publication Number Publication Date
AR080670A1 true AR080670A1 (es) 2012-05-02

Family

ID=43933363

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP100104235A AR080670A1 (es) 2009-11-17 2010-11-17 Metodo de produccion de derivados de acido glutamico marcados con f-18

Country Status (14)

Country Link
US (1) US20130149243A1 (es)
EP (1) EP2501663A2 (es)
JP (1) JP2013510891A (es)
KR (1) KR20120101452A (es)
CN (1) CN102712552B (es)
AR (1) AR080670A1 (es)
AU (1) AU2010321278B2 (es)
BR (1) BR112012011786A2 (es)
CA (1) CA2780930A1 (es)
IL (1) IL219698A0 (es)
MX (1) MX2012005733A (es)
RU (1) RU2012124810A (es)
TW (1) TW201121572A (es)
WO (1) WO2011060887A2 (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130124522A (ko) 2010-12-09 2013-11-14 지이 헬쓰케어 리미티드 방사성 추적자 조성물
EP2520557A1 (en) * 2011-05-03 2012-11-07 Bayer Pharma Aktiengesellschaft Novel precursors of glutamate derivatives
US9546193B2 (en) 2013-10-24 2017-01-17 The Regents Of The University Of California Compositions and methods for 18F-fluorodeoxyglycosylamines
CN113019279A (zh) * 2021-03-11 2021-06-25 山西医科大学第一医院 一种放射性药物制备的自动合成装置及其使用方法
WO2023229997A1 (en) * 2022-05-23 2023-11-30 Board Of Regents, The University Of Texas System Cgmp-compliant automated [18f]fspg production for clinical examination

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6774243B2 (en) * 1999-08-24 2004-08-10 Agouron Pharmaceuticals, Inc. Efficient synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates
WO2002018941A2 (en) * 2000-09-01 2002-03-07 Annovis, Inc. Screen for glutamate reuptake inhibitors, stimulators, and modulators
US7189383B2 (en) * 2002-08-02 2007-03-13 Mallinckrodt Inc. Radioactively labelled amino acid analogues, their preparation and use
GB0422004D0 (en) * 2004-10-05 2004-11-03 Amersham Plc Method of deprotection
BRPI0718055A2 (pt) * 2006-11-01 2013-11-05 Bayer Schering Pharma Ag Ácido l-glutâmico marcado com (f-18), l-glutamina maracada com (f-18), seus derivados e seu uso, bem como processos para sua preparação
EP2123621A1 (de) * 2008-05-20 2009-11-25 Bayer Schering Pharma Aktiengesellschaft Neue {F-18}-markierte L-Glutaminsäure- und L-Glutaminderivate (I), ihre Verwendung sowie Verfahren zu ihrer Herstellung
EP1923382A1 (de) * 2006-11-18 2008-05-21 Bayer Schering Pharma Aktiengesellschaft [F-18] markierte L-Glutaminsäure, [F-18] markiertes Glutamin, ihre Derivate und ihre Verwendung sowie Verfahren zu ihrer Herstellung
EP2123619A1 (de) * 2008-05-20 2009-11-25 Bayer Schering Pharma AG Neue [F-18]-Markierte L-Glutaminsäure-und L-Glutaminderivate (II), ihre Verwendung sowie Verfahren zu ihrer Herstellung
EP2123620A1 (en) * 2008-05-20 2009-11-25 Bayer Schering Pharma Aktiengesellschaft {F-19}-labeled L-Glutamic acid and L-Glutamine derivative (III), use thereof and method for obtaining them
CA2729635A1 (en) * 2008-07-03 2010-01-07 Ananth Srinivasan Compounds and processes for production of radiopharmaceuticals

Also Published As

Publication number Publication date
BR112012011786A2 (pt) 2019-09-24
HK1177928A1 (en) 2013-08-30
EP2501663A2 (en) 2012-09-26
MX2012005733A (es) 2013-01-22
WO2011060887A2 (en) 2011-05-26
WO2011060887A8 (en) 2011-10-20
TW201121572A (en) 2011-07-01
AU2010321278A1 (en) 2012-05-31
CN102712552A (zh) 2012-10-03
JP2013510891A (ja) 2013-03-28
CN102712552B (zh) 2015-07-22
US20130149243A1 (en) 2013-06-13
RU2012124810A (ru) 2013-12-27
IL219698A0 (en) 2012-07-31
CA2780930A1 (en) 2011-05-26
WO2011060887A3 (en) 2012-04-12
KR20120101452A (ko) 2012-09-13
AU2010321278B2 (en) 2014-08-14

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