AR071043A1 - Acido l -glutamico marcado con (f -18), l- glutamina marcada con (f-18), sus derivados y su uso, asi como procedimientos para su preparacion - Google Patents

Acido l -glutamico marcado con (f -18), l- glutamina marcada con (f-18), sus derivados y su uso, asi como procedimientos para su preparacion

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Publication number
AR071043A1
AR071043A1 ARP070104863A ARP070104863A AR071043A1 AR 071043 A1 AR071043 A1 AR 071043A1 AR P070104863 A ARP070104863 A AR P070104863A AR P070104863 A ARP070104863 A AR P070104863A AR 071043 A1 AR071043 A1 AR 071043A1
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Argentina
Prior art keywords
branched
unbranched
alkyl
compounds
ethoxycarbonyl
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ARP070104863A
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English (en)
Inventor
Raisa Nikolaevna Krasikowa
Ludger Dinkelborg
Keith Graham
Lutz Lehmann
Yuri Belokon
Olga Fedorovna Kuznetsova
Matthias Friebe
Mathias Berndt
Original Assignee
Inst Of Organoelement Compound
Inst Of Human Brain Ihb Ras Of
Bayer Schering Pharma Ag
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Filing date
Publication date
Priority claimed from RU2006138584/04A external-priority patent/RU2395489C2/ru
Priority claimed from EP06090211A external-priority patent/EP1923382A1/de
Application filed by Inst Of Organoelement Compound, Inst Of Human Brain Ihb Ras Of, Bayer Schering Pharma Ag filed Critical Inst Of Organoelement Compound
Publication of AR071043A1 publication Critical patent/AR071043A1/es

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    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations 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
    • A61K51/04—Organic compounds
    • A61K51/0402—Organic compounds carboxylic acid carriers, fatty acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
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    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/001—Acyclic or carbocyclic compounds
    • 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
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/16—Preparation 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 not involving the amino or carboxyl groups
    • 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
    • C07C229/04—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 being acyclic and saturated
    • C07C229/24—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 being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters 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
    • C07C271/22—Esters 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
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    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters 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
    • 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
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    • 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
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    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/04—Nickel compounds
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    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/04—Nickel compounds
    • C07F15/045—Nickel compounds without a metal-carbon linkage
    • 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
    • C07B2200/05—Isotopically 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)
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  • Pharmacology & Pharmacy (AREA)
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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

Abstract

Se describen los compuestos y la síntesis de ácido L-glutámico marcado con [F-18], L-glutamato marcado con [F-18], sus derivados de acuerdo con la formula (1) y sus usos. Reivindicacion 1: Compuestos de la formula general (1) en donde A es a) hidroxilo, b) alcoxi C1-5 ramificado o no ramificado, c) hidroxialcoxi C1-5 ramificado o no ramificado, d) O-alquil C1-5-(O-alquil C1-4)n-O-alquilo C1-4 ramificado o no ramificado, e) N(alquilo C1-5)2, f) NH2, g) N(H)-L, h) O-L o i) O-Z; G es a) hidroxilo, b) O-Z, b) O-alquilo C1-5 ramificado o no ramificado, c) O-alquenilo C2-5 ramificado o no ramificado, d) O-alquil C1-5-(O-alquil C1-4)n-O-alquilo C1-4 ramificado o no ramificado o e) O-alquinilo C2-5 ramificado o no ramificado; R1 y R2 es a) hidrogeno, b) 18F, c) 18F-alcoxi C1-5 ramificado o no ramificado, d) 18F-alquilo C1-5 ramificado o no ramificado, e) 18F-hidroxialquilo C1-5 ramificado o no ramificado, f) 18F-alquenilo C2-5 ramificado o no ramificado, o g) 18F-alquinilo C2-5 ramificado o no ramificado, h) hidroxilo, i) alquilo C1-5 ramificado o no ramificado o j) alcoxi C1-5 ramificado o no ramificado, con la condicion de que uno de los sustituyentes R1 o R2 contenga precisamente un isotopo 18F y el otro sustituyente no contenga un isotopo 18F; L es a) alquilo C1-5 ramificado o no ramificado, b) alquenilo C2-5 ramificado o no ramificado, c) alquil C1-5-(O-alquil C1-4)n-O-alquilo C1-4 ramificado o no ramificado o d) alquinilo C2-5 ramificado o no ramificado; y Z es un equivalente de cation metálico, en donde n = 0, 1, 2 o 3; y diastereomeros y enantiomeros. Reivindicacion 35: Uso de compuestos de acuerdo con las reivindicaciones 1 a 30 para preparar un medicamento para el diagnostico de enfermedades tumorales. Reivindicacion 37: Uso de compuestos de la formula (4) para preparar los compuestos de la formula (1) o (2) en donde A''' es a) hidroxilo, b) alcoxi C1-5 ramificado o no ramificado, c) hidroxialcoxi C1-5 ramificado o no ramificado, d) O-alquil C1-5-(O-alquil C1-4)n-O-alquilo C1-4 ramificado o no ramificado, e) N(alquilo C1-5)2, f) NH2, g) N(H)-U'', h) N(H)-L''' o i) O-L'''; G''' es a) hidroxilo, b) O-alquilo C1-5 ramificado o no ramificado, c) O-alquenilo C2-5 ramificado o no ramificado, d) O-alquil C1-5-(O-alquil C1-4)n-O-alquilo C1-4 ramificado o no ramificado, e) O-alquinilo C2-5 ramificado o no ramificado o f) trifenilmetoxi; R5 y R6 es e) H o f) E', con la condicion de que justamente uno de los sustituyentes R5 o R6 contenga E' y el otro sustituyente contenga H; E' es a) Cl, b) Br, c) mesiloxi, d) trifluoromesiloxi, e) nonafluorobutiloxi o f) tosiloxi; Q'' es a) N(H)-ter-butoxicarbonilo, b) N(H)-aliloxicarbonilo, c) N(H)-benciloxicarbonilo, d) N(H)-etoxicarbonilo, e) N(H)-metoxicarbonilo, f) N(H)-propoxicarbonilo, g) N(H)-2,2,2-tricloroetoxicarbonilo, h) N(H)-1,1-dimetilpropinilo, i) N(H)-1-metil-1-fenil-etoxicarbonilo, j) N(H)-1-metil-1-(4-bifenilil)-etoxicarbonilo, k) N(H)-ciclobutilcarbonilo, l) N(H)-1-metilciclobutilcarbonilo, m) N(H)-vinilcarbonilo, n) N(H)-alilcarbonilo, o) N(H)-adamantilcarbonilo, p) N(H)-difenilmetilcarbonjlo, q) N(H)-cinamilcarbonilo, r) N(H)-formilo, s) N(H)-benzoílo, t) N(H)-tritilo, u) N(H)-p-metoxifenil-difenilmetilo, v) N(H)-di-(p-metoxifenil)-fenilmetilo, w) el resto de formula (3) o x) N-(ter-butoxicarbonilo)2; L''' es a) alquilo C1-5 ramificado o no ramificado, b) alquenilo C2-5 ramificado o no ramificado, c) alquil C1-5-(O-alquil C1-4)n-O-alquilo C1-4 ramificado o no ramificado o d) alquinilo C2-5 ramificado o no ramificado; U'' es a) ter-butoxicarbonilo, b) aliloxicarbonilo, c) benciloxicarbonilo, o d) etoxicarbonilo; X'' y X''' son, de modo independiente entre si, a) alquilo C1-5 ramificado o no ramificado, b) arilo sustituido o no sustituido c) alquilarilo o d) heteroarilo, en donde n = 0, 1 o 2 y diastereomeros y enantiomeros. Reivindicacion 38: Uso de compuestos de la formula (5) para preparar los compuestos de la formula (1) o (2) en donde G''' es a) hidroxilo, b) O-alquilo C1-5 ramificado o no ramificado, c) O-alquenilo C2-5 ramificado o no ramificado, d) O-alquil C1-5-(O-alquil C1-4)n-O-alquilo C1-4 ramificado o no ramificado, e) O-alquinilo C2-5 ramificado o no ramificado o f) trifenilmetoxi; R5 y R6 es g) H o f) E', con la condicion de que justamente uno de los sustituyentes R5 o R6 contenga E' y el otro sustituyente no contenga un E'; E' es a) Cl, b) Br, c) mesiloxi, d) trifluoromesiloxi, e) nonafluorobutiloxi o f) tosiloxi; Q''' es a) N-ter-butoxicarbonilo, b) N-aliloxicarbonilo, c) N-benciloxicarbonilo, d) N-etoxicarbonilo, e) N-metoxicarbonilo, f) N-propoxicarbonilo, g) N-2,2,2-tricloroetoxicarbonilo, h) H, i) N-1-metil-1-fenil-etoxicarbonilo, j) N-1-metil-1-(4-bifenilil)-etoxicarbonilo, k) N-ciclobutilcarbonilo, l) N-1-metilciclobutilcarbonilo, m) N-vinilcarbonilo, n) N-alilcarbonilo, o) N-adamantilcarbonilo, p) N-difenilmetilcarbonilo, q) N-cinamilcarbonilo, r) N-formilo, s) N-benzoílo, en donde n = 0, 1, 2 o 3; y todos los posibles diastereomeros y enantiomeros. Reivindicacion 39: Compuestos de acuerdo con las reivindicaciones 1 a 30, caracterizados porque los compuestos para el diagnostico PET son apropiados en un rango de dosis de 37-600 MBq.
ARP070104863A 2006-11-01 2007-11-01 Acido l -glutamico marcado con (f -18), l- glutamina marcada con (f-18), sus derivados y su uso, asi como procedimientos para su preparacion AR071043A1 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2006138584/04A RU2395489C2 (ru) 2006-11-01 2006-11-01 [f-18] меченная l-глютаминовая кислота, [f-18] меченный l-глютамин, их производные и их применение, а также способ их получения
EP06090211A EP1923382A1 (de) 2006-11-18 2006-11-18 [F-18] markierte L-Glutaminsäure, [F-18] markiertes Glutamin, ihre Derivate und ihre Verwendung sowie Verfahren zu ihrer Herstellung

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AR071043A1 true AR071043A1 (es) 2010-05-26

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US (2) US20100217011A1 (es)
EP (1) EP2086924B1 (es)
JP (4) JP5529540B2 (es)
KR (1) KR101495924B1 (es)
CN (1) CN101595083B (es)
AR (1) AR071043A1 (es)
AU (1) AU2007315203B2 (es)
BR (1) BRPI0718055A2 (es)
CA (1) CA2667395C (es)
CL (2) CL2007003169A1 (es)
CO (1) CO6180453A2 (es)
CU (1) CU23825B1 (es)
EA (1) EA017713B1 (es)
EC (1) ECSP099304A (es)
ES (1) ES2701423T3 (es)
HK (1) HK1138568A1 (es)
IL (1) IL198022A0 (es)
MX (1) MX2009004686A (es)
NO (1) NO20092123L (es)
NZ (1) NZ576582A (es)
PE (1) PE20091723A1 (es)
SV (1) SV2009003251A (es)
TW (1) TWI415626B (es)
WO (1) WO2008052788A1 (es)

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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
MX2009004686A (es) 2006-11-01 2009-09-28 Bayer Schering Pharma Ag Acido l-glutamico marcado con [f-18], l-glutamina marcada con [f-18], sus derivados y su uso, asi como procedimientos para su preparacion.
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
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
KR101756793B1 (ko) * 2008-10-10 2017-07-11 메르크 앤드 씨에 Ｐｅｔ 방사성트레이서로서의 18ｆ-표지화된 엽산
US8722014B2 (en) * 2009-05-01 2014-05-13 Washington University 1 H-[1, 2, 3] triazole substituted amino acids and uses thereof
US8747809B2 (en) 2009-08-14 2014-06-10 The Trustees Of The University Of Pennsylvania Single diastereomers of 4-fluoroglutamine and methods of their preparation and use
EP2322171A3 (en) * 2009-11-17 2011-06-01 Bayer Schering Pharma Aktiengesellschaft Fluorine labeled L-glutamic acid derivatives
RU2012124810A (ru) * 2009-11-17 2013-12-27 Байер Фарма Акциенгезельшафт Способ получения f-18 меченных производных глутаминовой кислоты
CA2780840A1 (en) * 2009-11-17 2011-05-26 Bayer Pharma Aktiengesellschaft Iodine-labeled homoglutamic acid and glutamic acid derivatives
EP2338892A1 (en) * 2009-12-18 2011-06-29 Bayer Schering Pharma Aktiengesellschaft Prostate specific membrane antigen inhibitors
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EP2086924A1 (de) 2009-08-12
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US9375497B2 (en) 2016-06-28
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