WO2011003591A1 - Usage of low to medium-pressure liquid chromatography for the purification of radiotracers - Google Patents
Usage of low to medium-pressure liquid chromatography for the purification of radiotracers Download PDFInfo
- Publication number
- WO2011003591A1 WO2011003591A1 PCT/EP2010/004112 EP2010004112W WO2011003591A1 WO 2011003591 A1 WO2011003591 A1 WO 2011003591A1 EP 2010004112 W EP2010004112 W EP 2010004112W WO 2011003591 A1 WO2011003591 A1 WO 2011003591A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- container
- ethoxy
- vinyl
- methylaniline
- stationary phase
- Prior art date
Links
- 0 CC(CCO*c1ccc(C=Cc(cc2)ccc2N(C)C(OC(C)(C)C)=O)cc1)OS(c1ccc(C)cc1)(=O)=O Chemical compound CC(CCO*c1ccc(C=Cc(cc2)ccc2N(C)C(OC(C)(C)C)=O)cc1)OS(c1ccc(C)cc1)(=O)=O 0.000 description 1
- FHZFTHRHMJAIJN-ONEGZZNKSA-N CC(CCOc1ccc(/C=C/c(cc2)ccc2NC)cc1)F Chemical compound CC(CCOc1ccc(/C=C/c(cc2)ccc2NC)cc1)F FHZFTHRHMJAIJN-ONEGZZNKSA-N 0.000 description 1
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
Definitions
- the invention relates to a process for the production of radiotracers.
- this invention relates the isolation of radiotracers with containers filled with a stationary phase.
- the purification of the radiolabeled compound is normally achieved via a solid phase extraction (SPE) or a high-pressure liquid-chromatography (HPLC).
- SPE solid phase extraction
- HPLC high-pressure liquid-chromatography
- the SPE cartridges can also be part of a disposable synthesis kit for cassette-type modules. Nevertheless the cartridges used for purification of the radiolabeled compounds normally contain solid phase material in the range from 20 mg to 2 g. With this amount the complete removal of all by-products is often tedious and in many cases even not achievable.
- the current invention solves this technical problem by applying a disposable container for purification instead of using a multi-run HPLC purification step.
- the present invention generally relates the use of a normal or reversed-phase flash chromatography to purify radiolabeled compounds from any kind of byproducts.
- This flash chromatography is performed by any kind of disposable container filled with the solid phase material.
- These containers can be connected to any kind of flush system via tubings and can therefore be part of a disposable synthesis kit for radiopharmaceuticals on a cassette-type module or belong to a non-cassette-type module.
- the present invention relates to processes for the production of radiopharmaceuticals comprising the steps of: • radiolabeling of a precursor molecule and,
- the purification of the radiotracer comprises the step of liquid chromatography, wherein this liquid chromatography is a low- to medium-pressure liquid chromatography.
- this liquid chromatography is a low- to medium-pressure liquid chromatography.
- the pressure of the low to medium-pressure liquid chromatography is between 1 and 20 bar, more preferable between 1 and 10 bar, even more preferably between 1 and 5 bar.
- the radiolabeled compound contains at least one radioisotope that is selected in the group 99m Tc, 111 In, 18 F, 201 TI, 123 I, 124 I, 125 I, 131 I 1 34 CI, 11 C, 32 P, 72 As, 76 Br,
- the radiolabeled tracer is bearing a radioactive isotope for positron-emission-tomography.
- the radioisotope is selected from the group comprising 18 F, 68 Ga.
- the radiotracer can be used for imaging of CNS, cardiovascular or oncological diseases.
- the radiolabeld tracer is used for imaging of CNS disorders, preferable for detecting of A ⁇ plaques.
- Such tracers comprise aryl(or hetaryl)vinyl aniline derivatives such as, but not limited to 4-[(E)-2-(4- ⁇ 2-[2-(2-[F-
- the container is a cartridge, column or any kind of cylinder.
- the container is made from any kind of metal, alloy, plastic, glass, carbon or mixtures thereof.
- the material for the container is selected from the group of any kind of plastic, glass or mixture thereof, more preferably selected from USP class Vl plastics, and even more preferably from medical-grade polyethylene or polypropylene.
- the container is filled with a stationary phase.
- the container can contain additional parts such as but not limited to: porous frits, connectors and adaptors.
- the stationary phase is selected from the group comprising silica gel, modified silica gel, alumina, resins, polymers, copolymers or mixtures or layers thereof.
- the stationary phase is selected from the group comprising silica, alumina A, alumina B, alumina N, magnesium silicate, magnesium oxide, zirconium oxide, C30, C18, tC18, C8, C4, C2, tC2, amino propyl (NH2), cyano propyl (CN), diol, hydroxyapatite, cellulose, graphitized carbon and polystyrene/divinylbenzene polymers or copolymers thereof.
- 10 ⁇ g to 100 g of the stationary phase are filled into the container.
- 100 mg to 50 g of the stationary phase are filled into the container.
- 2 g to 20 g of the stationary phase are filled into the container.
- Even more preferably, 3.5 g to 10 g of the stationary phase are filled into the container.
- One or more of the containers of same or different dimension filled with the same or different stationary phases can be used for the process.
- the container filled with the stationary phase can be connected to tubings, syringes, needles, valves or further containers.
- the liquid phase for the purification process is selected from the group of organic solvents, water, aqueous solutions of salts, acids, bases or additives and mixtures thereof.
- the liquid phase is selected from the group comprising: pentane, hexane, heptane, octane, cyclopentane, cyclohexane, isooctane, toluene, p-xylole, chlorobenzene, benzene, diethylether, diisopropylether, tert-butyl methyl ether, nitromethane, chloroform, dichloromethane, 1 ,2-dichloroethane, triethylamine, pyridine, ammonia, acetone, tetrahydrofuran, ethyl acetate, methyl acetate, acetonitrile, isopropanol, ethanol, methanol, acetic acid, trifluoroacetic acid, water, saline solutions, buffers and mixtures thereof.
- the liquid phase is passed through the container by means known to the persons skilled in the art.
- the liquid phase is passed through the container via a pump, a syringe, a syringe pump, a gas stream, vacuum or by combinations thereof.
- detectors are: UV-detector, radioactivity detector, light scattering detector, conductometric detector, refractory index detector.
- the present invention relates to processes for the automated production of radiopharmaceuticals comprising the steps of:
- the purification of the radiotracer comprises the step of liquid chromatography, wherein this liquid chromatography is a low- to medium-pressure liquid chromatography.
- the pressure of the liquid chromatography is between 1 and 20 bar, more preferable between 1 and 10 bar.
- the radiolabeled compound contains at least one radioisotope that is selected in the group 99m Tc, 111 In, 18 F, 201 TI, 123 I, 124 I, 125 I, 131 I 1 34 CI, 11 C, 32 P, 72 As, 76 Br, 89 Sr, 153 Sm, 186 Re, 188 Re, 212 Bi, 213 Bi, 89 Zr, 86 Y, 90 Y, 67 Cu, 64 Cu, 192 Ir, 165 Dy, 177 Lu, 117m Sn, 213 Bi, 212 Bi, 211 At, 225 Ac, 223 Ra, 169 Yb, 68 Ga and 67 Ga.
- the radiolabeled tracer is bearing a radioactive isotope for positron-emission-tomography.
- the radioisotope is selected from the group compr ⁇ is • ing 18r F-, 68 ⁇ G>a.
- the container is a cartridge, column or any kind of cylinder.
- the container is made from any kind of metal, alloy, plastic, glass, carbon or mixtures thereof.
- the material for the container is selected from the group of any kind of plastic, glass or mixture thereof, more preferably selected from USP class Vl plastics, and even more preferably from medical-grade polyethylene or polypropylene.
- the container is filled with a stationary phase.
- the container can contain additional parts such as but not limited to: porous frits, connectors and adaptors.
- the stationary phase is selected from the group comprising silica gel, modified silica gel, alumina, resins, polymers, copolymers or mixtures or layers thereof.
- the stationary phase is selected from the group comprising silica, alumina A, alumina B, alumina N, magnesium silicate, magnesium oxide, zirconium oxide, C30, C18, tC18, C8, C4, C2, tC2, amino propyl (NH2), cyano propyl (CN), diol, hydroxyapatite, cellulose, graphitized carbon and polystyrene/divinylbenzene polymers or copolymers thereof.
- 10 ⁇ g to 100 g of the stationary phase are filled into the container.
- 100 mg to 50 g of the stationary phase are filled into the container.
- 2 g to 20 g of the stationary phase are filled into the container.
- One or more of the containers of same or different dimension filled with the same or different stationary phases can be used for the process.
- the container filled with the stationary phase can be connected to tubings, syringes, needles, valves or further containers.
- the liquid phase for the purification process is selected from the group of organic solvents, water, aqueous solutions of salts, acids, bases or additives and mixtures thereof.
- the liquid phase is selected from the group comprising: pentane, hexane, heptane, octane, cyclopentane, cyclohexane, isooctane, toluene, p-xylole, chlorobenzene, benzene, diethylether, diisopropylether, tert-butyl methyl ether, nitromethane, chloroform, dichloromethane, 1 ,2-dichloroethane, triethylamine, pyridine, ammonia, acetone, tetrahydrofuran, ethyl acetate, methyl acetate, acetonitrile, isopropanol, ethanol, methanol, acetic acid, trifluor fluor
- the liquid phase is passed through the container by means known to the persons skilled in the art.
- the liquid phase is passed through the container via a pump, a syringe, a syringe pump, a gas stream, vacuum or by combinations thereof.
- detectors are: UV-detector, radioactivity detector, light scattering detector, conductometric detector, refractory index detector.
- the process is an automated procedure for manufacturing of the radiolabeled tracer.
- the purification process is a standalone automated procedure combined with an automated synthesis of the radiotracer. In an other embodiment, the purification process is integrated into an automated synthesis of the radiotracer. In a preferred embodiment, a synthesizer is used for the production of the radiotracer and the purification process is established on the synthesizer. More preferably, the process of production and purification is performed without any manual operation.
- synthesis and purification of the radiotracer by "Medium pressure chromatography” are performed on a "Cassette type module" for the production of radiotracers know to the person skilled in the art, such as but not limited to: GE tracerlab MX (Coincidence FDG), GE Fastlab, IBA Synthera.
- the container for "Medium pressure chromatography” is part of the disposable cassette (or kit).
- the present invention relates to disposable kits for processes for the production of radiopharmaceuticals comprising the steps of:
- the kit comprises materials for the synthesis of the radiotracer and the container for purification, wherein the container is defined as described above.
- the invention further relates to the following counts:
- a method for production of radiotracers comprising a purification step using
- a process according to counts 1-2, wherein the stationary phase is selected from the group consisting of silica gel, modified silica gel, alumina, resins, polymers, gels or mixtures or layers thereof are used. 4. A process according to counts 1-3, wherein a container filled with a stationary phase selected from the group comprising silica, alumina A, alumina B, alumina N, magnesium silicate, magnesium oxide, zirconium oxide, C30, C18, tC18, C8, C4, C2, tC2, amino propyl (NH2), cyano propyl (CN), diol, hydroxyapatite, cellulose, graphitized carbon,
- polystyrene/divinylbenzene polymers polystyrene/divinylbenzene copolymers or mixtures thereof is used.
- chromatography is selected from the group consisting of organic solvents, water aqueous solutions of salts, acids or bases or additives and mixtures thereof.
- Figure 1 Chromatogram of medium pressure chromatography of crude 4-[(E)-2- (4- ⁇ 2-[2-(2-[F-18]fluoroethoxy)ethoxy]ethoxy ⁇ -phenyl)vinyl]-N-methylaniline.
- FIG. 2 Analytical HPLC chromatograms " (Atlantis T3; 150 * 4,6 mm ; 3 ⁇ m; Merck Waters; 40-90 % MeCN in 5mM KH 2 PO 4 pH 2.2) of crude product mixture (a, b) and purified product (c, d) after "Medium pressure
- Figure 3 Setup of tracerlab MX synthesis (picture was copied from Coincidence software and modified).
- Figure 4 Chromatogram of medium pressure chromatography of crude 4-[(E)-2- (6- ⁇ 2-[2-(2-[F-18]fluoroethoxy)ethoxy]ethoxy ⁇ pyhdin-3-yl)vinyl]-N-methylaniline.
- Figure 5 Analytical HPLC chromatograms (Chromolith SpeedRod; Merck; 0-95 % MeCN in 1OmM Na 2 HPO 4 pH 7.4) of crude product mixture (a, b) and purified product (c, d) after "Medium pressure chromatography”.
- Figure 9 Analytical HPLC of rude product of MX synthesis prior passing through "Purification cartridge” (sample was taken from reactor); top radioactivity;
- FIG. 10 Analytical HPLC of 4-[(E)-2-(4- ⁇ 2-[2-(2-[F-18]fluoroethoxy)ethoxy]- ethoxy ⁇ phenyl)vinyl]-N-methylaniline after MX synthesis and cartridge based purification; top radioactivity; bottom: UV signal 320 nm
- [F-18]Fluoride (1.0 GBq) was trapped on a QMA cartridge (SepPak light, Waters). After elution with tetrabutylammonium hydroxide solution (300 ⁇ L 4% tetrabutylammonium hydroxide in water and 700 ⁇ L acetonitrile), the mixture was dried under gentle nitrogen stream at 120 0 C. Drying was repeated after addition of acetonitrile. 3.5 mg mesylate precursor were dissolved in 1.8 mL acetonitrile and added to the dried residue. The resulting mixture was heated at 110 0 C for 10 min. 2 mL 1.5M HCI were added and the solution was heated at 110 0 C for 5 min.
- tetrabutylammonium hydroxide solution 300 ⁇ L 4% tetrabutylammonium hydroxide in water and 700 ⁇ L acetonitrile
- Radioactive and non-radioactive impurities were successfully removed to provide the same quality of the tracer as after purification with semipreparative HPLC (e.g. Zorbax Bonus RP, Agilent; 55 % MeCN in 0.1 M ammonium formiate).
- semipreparative HPLC e.g. Zorbax Bonus RP, Agilent; 55 % MeCN in 0.1 M ammonium formiate.
- Vial E potassium carbonat/kryptofix (in acetonitrile/water)
- [F-18]Fluoride (1.24 GBq) was trapped on a QMA cartridge (SepPak light, Waters). After elution with potassium carbonate/kryptofix mixture (5 mg kryptofix, 1 mg potassium carbonate in acetonitrile/water), the mixture was dried under gentle nitrogen stream at 120 0 C. Drying was repeated after addition of acetonitrile (2 x 1 mL). 4 mg tosylate precursor were dissolved in 1 ml_ acetonitrile and added to the dried residue. The resulting mixture was heated at 110 °C for 10 min. After cooling to approximately 60 0 C, 500 ⁇ L 2M HCI were added and the solution was heated at 110 0 C for 5 min.
- Precursor 2c was dissolved in the "red capped vial" during the synthesis sequence using approximately 1.8 mL acetonitrile from the "blue capped vial”. Fluoride (2.4 GBq) was transferred to the MX module and trapped on the QMA cartridge. The activity was eluted into the reactor with potassium carbonate/kryptofix mixture from the "eluent vial”. After azeotropic drying (heating, vacuum, nitrogen stream and addition of acetonitrile from the "blue capped vial"), the solution of 2c in acetonitrile was transferred from the "red capped vial" into the reactor. The resulting mixture was heated for 10 min at 120 0 C.
- HCI was transferred via the syringes from the "green capped vial” into the reactor.
- the mixture was heated for 5 min at 110 0 C.
- solvent mixture 1 from “Solvent bag 1” was flushed through the "Purification cartridge” by the left syringe.
- the crude product mixture was mixed with sodium hydroxid/buffer mixture from the "2 ml_ syringe” and diluted with the solvent 1 from "Solvent bag 1".
- the diluted crude product mixture was passed through "Purification cartridge”.
- the remove non-radioactive by-products, solvent 1 from "Solvent bag 1" was filled into the left syringe and flushed through the "Purification cartridge” into the waste bottle. This procedure was repeated six times.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/383,224 US8968701B2 (en) | 2009-07-10 | 2010-07-06 | Usage of low to medium-pressure liquid chromatography for the purification of radiotracers |
CA2767475A CA2767475A1 (en) | 2009-07-10 | 2010-07-06 | Usage of low to medium-pressure liquid chromatography for the purification of radiotracers |
CN2010800312484A CN102471177A (en) | 2009-07-10 | 2010-07-06 | Usage of low to medium-pressure liquid chromatography for the purification of radiotracers |
EP10734910A EP2451760A1 (en) | 2009-07-10 | 2010-07-06 | Usage of low to medium-pressure liquid chromatography for the purification of radiotracers |
JP2012518815A JP2012532164A (en) | 2009-07-10 | 2010-07-06 | Use of low-medium pressure liquid chromatography for the purification of radioactive tracers. |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09009009 | 2009-07-10 | ||
EP09009009.3 | 2009-07-10 | ||
EP10075022 | 2010-01-14 | ||
EP10075022.3 | 2010-01-14 |
Publications (1)
Publication Number | Publication Date |
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WO2011003591A1 true WO2011003591A1 (en) | 2011-01-13 |
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ID=42752296
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PCT/EP2010/004112 WO2011003591A1 (en) | 2009-07-10 | 2010-07-06 | Usage of low to medium-pressure liquid chromatography for the purification of radiotracers |
Country Status (7)
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US (1) | US8968701B2 (en) |
EP (1) | EP2451760A1 (en) |
JP (1) | JP2012532164A (en) |
KR (1) | KR20120034724A (en) |
CN (1) | CN102471177A (en) |
CA (1) | CA2767475A1 (en) |
WO (1) | WO2011003591A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011151281A1 (en) * | 2010-06-04 | 2011-12-08 | Bayer Pharma Aktiengesellschaft | Method for production of f-18 labeled amyloid beta ligands |
WO2011151273A1 (en) * | 2010-06-04 | 2011-12-08 | Bayer Pharma Aktiengesellschaft | Method for production of f-18 labeled amyloid beta ligands |
WO2011151282A1 (en) * | 2010-06-04 | 2011-12-08 | Bayer Pharma Aktiengesellschaft | Method for production of f-18 labeled amyloid beta ligand |
EP2579902A1 (en) * | 2010-06-04 | 2013-04-17 | Piramal Imaging SA | Method for production of f-18 labeled amyloid beta ligands |
Families Citing this family (4)
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CN113564722A (en) * | 2013-11-13 | 2021-10-29 | 通用电气健康护理有限公司 | Dual operation box |
CN103645254B (en) * | 2013-11-28 | 2015-01-07 | 江苏省原子医学研究所 | Method for analyzing content of A beta plaque developer precursor AV45 |
CN108854926A (en) * | 2018-05-30 | 2018-11-23 | 杭州启创生物技术有限公司 | One-time reaction device and a kind of tracer synthesizer and its production tracer method |
CN113019279A (en) * | 2021-03-11 | 2021-06-25 | 山西医科大学第一医院 | Automatic synthesis device for preparing radiopharmaceuticals and using method thereof |
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KR100789847B1 (en) | 2004-12-15 | 2007-12-28 | (주)퓨쳐켐 | A Preparation Method of Organo Fluoro Compounds in Alcohol Solvents |
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2010
- 2010-07-06 WO PCT/EP2010/004112 patent/WO2011003591A1/en active Application Filing
- 2010-07-06 JP JP2012518815A patent/JP2012532164A/en active Pending
- 2010-07-06 CN CN2010800312484A patent/CN102471177A/en active Pending
- 2010-07-06 US US13/383,224 patent/US8968701B2/en active Active
- 2010-07-06 CA CA2767475A patent/CA2767475A1/en not_active Abandoned
- 2010-07-06 EP EP10734910A patent/EP2451760A1/en not_active Withdrawn
- 2010-07-06 KR KR1020127000598A patent/KR20120034724A/en not_active Application Discontinuation
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DE19809960A1 (en) * | 1998-03-07 | 1999-09-09 | Forschungszentrum Juelich Gmbh | Process for the preparation of [· 1 ·· 5 · O] butanol and device for carrying out the process |
WO2003065882A2 (en) | 2002-02-06 | 2003-08-14 | The Johns Hopkins University | Non-invasive diagnostic imaging technology for mitochondria using radiolabeled lipophilic salts |
WO2004035744A2 (en) * | 2002-10-18 | 2004-04-29 | Biostream, Inc. | Methods for purifying radiolabelled compounds |
WO2006071470A2 (en) * | 2004-12-03 | 2006-07-06 | California Institute Of Technology | Microfluidic devices with chemical reaction circuits |
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WO2011151281A1 (en) * | 2010-06-04 | 2011-12-08 | Bayer Pharma Aktiengesellschaft | Method for production of f-18 labeled amyloid beta ligands |
WO2011151273A1 (en) * | 2010-06-04 | 2011-12-08 | Bayer Pharma Aktiengesellschaft | Method for production of f-18 labeled amyloid beta ligands |
WO2011151282A1 (en) * | 2010-06-04 | 2011-12-08 | Bayer Pharma Aktiengesellschaft | Method for production of f-18 labeled amyloid beta ligand |
EP2579902A1 (en) * | 2010-06-04 | 2013-04-17 | Piramal Imaging SA | Method for production of f-18 labeled amyloid beta ligands |
AU2011260411B2 (en) * | 2010-06-04 | 2014-05-08 | Life Molecular Imaging Limited | Method for production of F-18 labeled amyloid beta ligands |
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EP2579902B1 (en) * | 2010-06-04 | 2017-07-12 | Piramal Imaging SA | Method for production of f-18 labeled amyloid beta ligands |
Also Published As
Publication number | Publication date |
---|---|
EP2451760A1 (en) | 2012-05-16 |
US8968701B2 (en) | 2015-03-03 |
CA2767475A1 (en) | 2011-01-13 |
CN102471177A (en) | 2012-05-23 |
JP2012532164A (en) | 2012-12-13 |
US20120184749A1 (en) | 2012-07-19 |
KR20120034724A (en) | 2012-04-12 |
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