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-18Info
- 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
Links
- 238000000034 method Methods 0.000 title abstract 3
- 150000002306 glutamic acid derivatives Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 7
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 5
- -1 isoindol-2-yl (phthalimido) Chemical class 0.000 abstract 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 3
- 125000006239 protecting group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000006242 amine protecting group Chemical group 0.000 abstract 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 238000003682 fluorination reaction Methods 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000005905 mesyloxy group Chemical group 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- 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
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
-
- 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
- C07C227/18—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 involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
- C07C227/20—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 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
-
- 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
-
- 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
- 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
- A61K51/0404—Lipids, e.g. triglycerides; Polycationic carriers
- A61K51/0406—Amines, polyamines, e.g. spermine, spermidine, amino acids, (bis)guanidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C227/30—Preparation of optical isomers
-
- 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
- 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
-
- 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
- C07C309/72—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
- 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
Landscapes
- 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).
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)
| 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)
| 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 |
-
2010
- 2010-11-06 CA CA2780930A patent/CA2780930A1/en not_active Abandoned
- 2010-11-06 AU AU2010321278A patent/AU2010321278B2/en not_active Ceased
- 2010-11-06 WO PCT/EP2010/006766 patent/WO2011060887A2/en not_active Ceased
- 2010-11-06 RU RU2012124810/04A patent/RU2012124810A/ru not_active Application Discontinuation
- 2010-11-06 JP JP2012539215A patent/JP2013510891A/ja active Pending
- 2010-11-06 CN CN201080061643.7A patent/CN102712552B/zh not_active Expired - Fee Related
- 2010-11-06 KR KR1020127015547A patent/KR20120101452A/ko not_active Withdrawn
- 2010-11-06 MX MX2012005733A patent/MX2012005733A/es not_active Application Discontinuation
- 2010-11-06 US US13/510,365 patent/US20130149243A1/en not_active Abandoned
- 2010-11-06 BR BR112012011786A patent/BR112012011786A2/pt not_active IP Right Cessation
- 2010-11-06 EP EP10773865A patent/EP2501663A2/en not_active Withdrawn
- 2010-11-17 AR ARP100104235A patent/AR080670A1/es unknown
- 2010-11-17 TW TW099139604A patent/TW201121572A/zh unknown
-
2012
- 2012-05-09 IL IL219698A patent/IL219698A0/en unknown
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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