[go: up one dir, main page]

WO2006121035A1 - Procede de production d’un compose organique marque avec un halogene radioactif - Google Patents

Procede de production d’un compose organique marque avec un halogene radioactif Download PDF

Info

Publication number
WO2006121035A1
WO2006121035A1 PCT/JP2006/309303 JP2006309303W WO2006121035A1 WO 2006121035 A1 WO2006121035 A1 WO 2006121035A1 JP 2006309303 W JP2006309303 W JP 2006309303W WO 2006121035 A1 WO2006121035 A1 WO 2006121035A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
radioactive
acid
following formula
nitrogen
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2006/309303
Other languages
English (en)
Japanese (ja)
Inventor
Soichi Nakamura
Tetsuya Mochizuki
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nihon Medi Physics Co Ltd
Original Assignee
Nihon Medi Physics Co Ltd
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 Nihon Medi Physics Co Ltd filed Critical Nihon Medi Physics Co Ltd
Publication of WO2006121035A1 publication Critical patent/WO2006121035A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5456—Arylalkanephosphonium 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
    • 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
    • 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
    • C07C29/14—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 a —CHO group
    • 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

Definitions

  • the present invention relates to a method for producing a radioactive halogen-labeled organic compound. More specifically, positron emission tomography (hereinafter referred to as PET) or single photon emission tomography (hereinafter referred to as PET) of diseases associated with mitochondrial dysfunction
  • PET positron emission tomography
  • PET single photon emission tomography
  • the present invention relates to a method for producing a radioactive halogen-labeled organic compound that can be used for diagnosis using SPECT).
  • Nuclear medicine tests represented by PET and SPECT are effective in the diagnosis of various diseases including heart disease and cancer.
  • a drug labeled with a specific radioisotope hereinafter referred to as “radiopharmaceutical”
  • Radiopharmaceutical a drug labeled with a specific radioisotope
  • ⁇ -rays released directly or indirectly by the administration of the drug are detected. It is.
  • Nuclear medicine testing has excellent properties such as high specificity and sensitivity to diseases, and it can obtain information on the function of the lesion, as well as other testing methods. It has a characteristic.
  • [ 18 F] 2_Fluoro-2-doxy-D-glucose one of the radiopharmaceuticals used in PET examinations, has the property of accumulating in areas where glucose metabolism is active. It becomes possible to specifically detect active tumors.
  • nuclear medicine examination is a method performed by tracking the distribution of administered radiopharmaceuticals
  • the information obtained varies depending on the nature of the radiopharmaceutical.
  • radiopharmaceuticals for various diseases have been developed, and some have been clinically applied.
  • various tumor diagnostic agents, blood flow diagnostic agents, receptor mapping agents and the like have been developed.
  • 18 F-FBnTP 4-Fluorobenzyl Triphenyl Phosphate Salt
  • Patent Document 1 International Publication No. 03/065882 Pamphlet
  • Non-Patent Literature l Shoup, TM et al., Fluorine- 18 and Iodine- 125 Labeled Tetraphenyl phosphonium Ions as Potential PET and SPECT Imaging Agents for NCS Tumors., S upplement to The Journal of Nuclear Medicine, USA, The Official Publication of the Society of Nuclear Medicine, Inc., Volume 45, Abstract Book Supplement, May 200 4, p447, No. 1391
  • Patent Document 1 the production method disclosed in the above-mentioned pamphlet of International Publication No. 03/065882 (Patent Document 1) requires a three-step reaction such as reduction, bromination, and addition of phosphine after 18 F labeling. Since the production yield is a value obtained by multiplying the yield of each reaction step, the number of reaction steps is generally large, which is preferable for the production of pharmaceutical products.
  • radioisotopes used in radiopharmaceuticals have a short half-life, so they decay early and end their lives.
  • Patent Document 1 water is used in the purification process of the 18 F labeled product, and this water needs to be removed in the subsequent reaction. .
  • the water removal process requires a longer time compared to the removal of the organic solvent.
  • the decay of radioisotopes also occurs in the manufacturing process of radiopharmaceuticals, and this causes a decrease in the radioactivity of the manufactured radiopharmaceuticals, that is, the yield of the compound itself that exhibits its efficacy as a radiopharmaceutical.
  • Patent Document 1 discloses a value of about 15% as a production yield of 18 F-FBnTP.
  • Non-Patent Document 1 the number of reaction steps after 18 F labeling can be reduced.
  • this method is not practical because the labeling yield of 18 F itself is low and the yield of the final compound is as low as about 3%.
  • R is an aryl group in which one or more hydrogens are replaced with a radioactive neurogen.
  • R, R and R are each independently hydrogen, alkyl group
  • a compound represented by the following formula (1) characterized in that it comprises a step of reacting with a compound represented by a kill group, an aryl group and a heteroaryl group optionally containing nitrogen, oxygen or sulfur.
  • R is an aryl group in which one or more hydrogens are replaced with a radioactive neurogen.
  • heteroaryl group in which one or more hydrogens are substituted with radioactive halogen, E is phosphorus or nitrogen, R, R and R are each independently hydrogen, alkyl group, aralkyl group, aryl group, and
  • halogen-containing organic compound selected from the group consisting of heteroaryl groups optionally containing nitrogen, oxygen or sulfur.
  • the present invention provides the following formula (5):
  • a compound represented by the following formula (4) characterized by comprising a step of reacting with a compound represented by the formula (4) selected from the group consisting of a kill group, an aryl group and a heteroaryl group optionally containing nitrogen, oxygen or sulfur:
  • n is an integer of 1 to 6
  • X is a radioactive halogen
  • Ar is an arylene group or a heteroarylene group
  • E is phosphorus or nitrogen
  • R, R and R are independently hydrogen, alkyl group, aralkyl
  • radiohalogen-containing organic compound represented by a group selected from the group consisting of heteroaryl groups optionally containing nitrogen, oxygen or sulfur.
  • Ar is not particularly limited as long as it is an arylene group or a heteroarylene group, but an arylene group having 6 to 18 carbon atoms, or a carbon number of 3 optionally containing nitrogen, oxygen, or sulfur. It is preferred to use from 1 to 18 heteroarylene groups selected from the group consisting of phenylene, naphthalene, anthracenylene, phenanthrenelene, naphthacenylene, pyridinylene, quinolinylene, freeylene and thiophenylene. It is more preferable.
  • X is not particularly limited as long as it is a radiohalogen.
  • X selected from the group consisting of radiofluorine, radiobromine, radioiodine, and radioastatin can be preferably used, and more preferably.
  • 18 F, 7 3 ⁇ 4r ⁇ 7 3 ⁇ 4r ⁇ 77 Br ⁇ 8 r ⁇ 8 3 ⁇ 4r ⁇ m I, I, 125 I, m I, 13 2 I, and 211 At force can also be used.
  • positron emitting nuclides such as 18 F, 7 3 ⁇ 4r, and 131 1 can be preferably used when used as a medicine for PET examination.
  • R, R and R may be the same or different and each independently represents a hydrogen atom or an alkyl group.
  • An aralkyl group, an aryl group, and a heteroallyl group Preferably, independently of each other, hydrogen, an alkyl group having 1 to 6 carbon atoms, and an alkyl group having 7 to 12 carbon atoms.
  • a group selected from the group consisting of an alkyl group having 6 to 18 carbon atoms and a heteroaryl group having 3 to 18 carbon atoms optionally containing nitrogen, oxygen or sulfur can be used.
  • the acidic condition which is a synthetic reaction condition can be given by various methods.
  • the acid condition is given by adding an acid to the reaction solution containing the radioactive halogen-containing alcohol. It is done.
  • hydrochloric acid odorous acid, sulfuric acid, formic acid, acetic acid, hydrobromic acid, propionic acid, trifluoromethanesulfonic acid, paratoluenesulfonic acid
  • aluminum chloride aluminum bromide
  • Zinc chloride, zinc bromide, calcium chloride salt, calcium bromide, boron trifluoride, boron trichloride, boron tribromide are exemplified, but preferably odorous acid, acetic acid, hydrobromic acid and Those selected from the group consisting of para-toluenesulfonic acid can also be used.
  • acidic conditions can be given by adding an amine or phosphine to be reacted with a radioactive neuron-containing alcohol as an acid salt thereof.
  • Various acidic salts can be used, and examples thereof include triphenylphosphine 'hydrochloride, trimethylamine' hydrochloride, triethylamine 'hydrochloride.
  • the amount of acid to be added is not particularly limited as long as sufficient acidic conditions can be given. For example, it is sufficient to add about 1 ⁇ 10 9 as a molar ratio with respect to the alcohol.
  • the alcohol form labeled with radioactive halogen can be obtained by various methods. For example, the following formula (7)
  • Ar represents an arylene group or heteroarylene group
  • R represents a -tro group, a trialkylammonium group.
  • X is a radioactive halogen
  • Ar is an arylene group or a heteroarylene group
  • an alcohol form is obtained by synthesizing a radionogen-containing aldehyde form represented by the following formula and reducing the aldehyde form by various methods. Can do.
  • a method of reducing the radioactive aldehyde- and rogen-containing aldehyde form to an alcohol form for example, a method of contacting a reaction solution containing the aldehyde form with a reducing agent can be used.
  • a reducing agent known ones can be used.
  • various boron compounds and various aluminum compounds can be preferably used.
  • the boron compounds include sodium borohydride, lithium borohydride, hydrogenated tree sec-butylboron lithium, hydrogenated tree sec-potassium borohydride potassium, zinc borohydride, and lithium triethylborohydride.
  • the selected one can be preferably used, and more preferably sodium borohydride can be used.
  • aluminum compound those selected from the group consisting of aluminum lithium hydride, triisopropoxy aluminum, tri-t-butoxy aluminum lithium hydride, and sodium di (2-methoxyethoxy) aluminum hydride are preferably used. be able to.
  • n is an integer from 0 to 5
  • X is a radiohalogen
  • Ar is an arylene group or a heteroarylene group
  • a reaction solution containing a radiohalogen-containing aldehyde is represented by the following formula: (Five)
  • n is an integer of 1 to 6
  • X is a radiohalogen
  • Ar is an arylene group or a heteroarylene group.
  • the radiohalogen-containing alcohol obtained by this process can be used as a raw material for the method for producing the radiohalogen-labeled organic compound of the present invention.
  • specific examples of Ar and X are the same as those described above with respect to formulas (4) and (5).
  • the production method of the radioactive halogen used in the production method of the present invention is carried out by a production method known per se.
  • a production method known per se for example, in the case of radioactive 18-fluorine ( 18 F), it is obtained by generating 18 F from a 18 0-concentrated water (H 18 0) by a nuclear reaction [ 18 0 (p, n) ⁇ 18 F] in a cyclotron.
  • radioactive halogen-containing alcohol can be directly reacted with an amine or phosphine
  • an aromatic compound having a radioactive halogen substituent, in particular 1 A phosphor salt or an ammonium salt compound having an aromatic compound in which the above hydrogen is substituted with a radioactive halogen can be produced with high yield.
  • the method for synthesizing 18 F-FB nTP according to the present invention is a method carried out by reacting [ 18 F] 4-fluorinated benzyl alcohol with triphenylphosphine under acidic conditions.
  • [ 18 F] 4_Fluorobenzyl alcohol is a radioactive halogen-containing alcohol to be used in a known method, for example, a method described in a document (Patent Document 1: International Publication No. 03/065882 pamphlet). Can be synthesized based on. Specifically, the following formulas (9) and (10
  • a potassium carbonate solution and an acetonitrile solution of a phase transfer catalyst (for example, Talibufix 222, product name, manufactured by Merck & Co., Inc.) are added to a reaction vessel, and 18 F-containing 18 0— Add condensed water. Thereafter, the liquid in the reaction vessel is evaporated to dryness to activate 18 F.
  • the amount of potassium carbonate is 0.50 to 1.0, preferably 0.55 to 0.80 in terms of a molar ratio with respect to the intended amount of 4-trimethylammo-benzaldehyde salt as the labeling precursor, and the amount of the phase transfer catalyst is The molar ratio of potassium carbonate is between 2.0 and 4.0.
  • a ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ , ⁇ -dimethylformaldehyde (DMF) solution of 4-trimethylammonium benzaldehyde salt is placed in the above reaction vessel at 80 to 160 ° C, preferably 110 to 130 ° C.
  • DMF dimethylformaldehyde
  • 4-Fluorobenzaldehyde is obtained by heating for 3 to 20 minutes, preferably 5 to 10 minutes.
  • the reaction solution of [ 18 F] 4-fluorobenzaldehyde is purified to remove unreacted labeling precursor, 18 F, potassium carbonate, and phase transfer catalyst.
  • diethyl ether is added to the above reaction solution, and this solution is passed through a normal phase column (for example, Sep-Pak Plus, Silica Cartridges, product name, manufactured by Nippon Waters Co., Ltd.).
  • a method of obtaining a [ 18 F] 4-fluorobenzaldehyde as a jetyl ether solution by holding a labeling precursor, 18 F, potassium carbonate, and a phase transfer catalyst in a column can be used.
  • the amount of the jetyl ether added to the reaction solution may be an amount sufficient to elute the target [ 18 F] 4-fluorobensaldehyde from the normal phase column used.
  • the amount of the jetyl ether added to the reaction solution may be an amount sufficient to elute the target [ 18 F] 4-fluorobensaldehyde from the normal phase column used.
  • the reaction solution may be purified using 0.4 mL of the reaction solution using a normal phase column with a volume of 1 mL, it is sufficient to add 2 mL of jetyl ether.
  • a solution obtained by adding water to the reaction solution of [ 18 F] 4-fluorene benzaldehyde is used as a reverse phase column (for example, Sep-Pak Plus C18 Cartridges, product name, Nippon
  • the column precursor is passed through to remove the unreacted labeling precursor and 18 F, potassium carbonate, and the phase transfer catalyst, and then the column is dried and then passed through the jetyl ether solution and held in the column.
  • a method to elute [ 18 F] 4-fluo-benzoaldehyde be able to.
  • 4-trimethylammo-benzbenzaldehyde salt used in the above synthesis can be obtained by a known method, for example, literature (for example, Alan A. et al., Reductive Amination of [18F] Fluoroben zaldehydes: Radiosyntheses of [2-18F]-and [4-18F] Fluorodexetimides, Journal of Labelled Compounds and Radiopharmaceuticals, vol.XXVIII, No.10, 1990, p.1189), specifically, The method can be used.
  • methyl trifluoromethanesulfonate is added to a methylene chloride solution of 4- ⁇ , ⁇ -dimethylaminobenzaldehyde in an argon stream and heated to reflux for 6 hours. After heating, the solvent is concentrated to dryness, water is added to the resulting residue, washed with ethyl acetate and chloroform, and the water after washing is concentrated to dryness. It is obtained by adding jetyl ether to the residue and filtering the precipitated crystals.
  • the reaction solution containing 18 F-FBnTP is obtained by heating and reacting under acidic conditions.
  • a solution obtained by adding jetyl ether to the reaction solution containing 18 F-FBnTP was passed through a normal phase column (for example, Sep-Pak Plus, Silica Cartridges, product name, manufactured by Nippon Waters Co., Ltd.), 18 F-FBnTP is obtained by passing a mixed solution of chloroform / formaldehyde (8/1) through the column, concentrating and drying the collected solution.
  • the acidic condition can be provided by including an acid in the reaction solution.
  • the method of adding an acid need not be particularly limited. A method of adding an acid to a solution containing the above-mentioned radioactive halogen-containing alcohol is added, or a solution containing a radioactive halogen-containing alcohol is added to a reaction vessel previously containing an acid. Can be used.
  • acidic conditions can be obtained by using an acid-containing compound added to the radioactive halogen-containing alcohol. For example, when triphenylphosphine is used as an adduct, and the acid to be contained in the reaction solution is hydrogen bromide, it is introduced into the reaction vessel as a triphenylphosphine benzoate, which contains radioactive halogen.
  • the amount of acid to be contained in the reaction solution is determined by the amount of the radiohalogen-containing alcohol used, but is not particularly limited as long as sufficient acidic conditions can be given.
  • 40 ⁇ mol of the labeling precursor 4-trimethylammonium benzaldehyde salt was used for 18 F labeling, followed by a reduction reaction [ 18 F] 4-fluoro oral benzyl alcohol, 400 ⁇ mol
  • the reaction is carried out using trifluorophosphine, 0.5 mL of 25% hydrobromic acid is added (formula (11)).
  • the heating condition is usually a temperature between 80 and 200 ° C., preferably 120 to 180 ° C., and the heating time is preferably 1 to 30 minutes.
  • the amount of radioactivity was measured with a radioisotope “dose” calibrator (model: CRC-15R) manufactured by CAPINTEC.
  • 4-trimethylammonium benzaldehyde salt (12 • 5 mg, 40 ⁇ mol) synthesized in the above process is dissolved in ⁇ , ⁇ -dimethylformaldehyde (0.4 mL), added to the glass container, and further 120 Heated at ° C for 10 minutes. Allow the glass container to cool, then add jetyl ether (2 mL) and pass through the normal phase column (Sep-Pak (registered trademark) Plus, Silica Cartridges, product name, manufactured by Nihon Waters Co., Ltd.) twice. The eluted liquid was collected repeatedly.
  • the ram force eluting solution is passed through a column packed with 10% sodium borohydride-containing alumina (400 mg) and collected in a glass container containing triphenylphosphine (104.9 mg, 400 mol). Gathered. The glass container was heated and concentrated, and after distilling off the jetyl ether, 25% hydrobromic acetic acid (0.5 mL) was added and heated at 160 ° C. for 5 minutes. Then, the reaction solution is allowed to cool, and is injected with a normal phase column (Sep-Pak (registered trademark) Plus, Silica Cartridges, product name, manufactured by Nippon Waters Co., Ltd.) with the addition of jetyl ether (2 mL).
  • a normal phase column Sep-Pak (registered trademark) Plus, Silica Cartridges, product name, manufactured by Nippon Waters Co., Ltd.
  • Jetyl ether (4 mL) was added to the column to remove impurities, and the target product was adsorbed and collected on the column.
  • the collected solution was evaporated by heating at 130 ° C to obtain 18 F-FBnTP. (38.3MBq, 90.8MBq converted to F time).
  • the obtained 18 F-FBnTP was subjected to TLC analysis under the following conditions, and the radiochemical purity was determined as the area% of the 18 F-FBnTP peak (R 0.2). The radiochemical purity obtained was 99%. Thus, it was confirmed that 18 F-FBnTP can be synthesized according to the present invention.
  • TLC plate kieselgel 60 F Art. 5715 (product name, Merck).
  • Detector Rita Star (product name, manufactured by raytesy).
  • the radiochemical yield of the obtained 18 F-FBnTP was determined by the following formula (I). As a result, the radiochemical yield was 67%.
  • the radiochemical yield of 18 F-FBnTP has been reported to be about 15% (WO 03/065882). It was improved to 67% from pamphlet).
  • the radiohalogen-labeled organic compound obtained by the method of the present invention is useful as a radiopharmaceutical used in the diagnosis by PET or SPECT of diseases associated with mitochondrial dysfunction and used in the field of nuclear medicine. it can.

Landscapes

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

Abstract

Le problème à résoudre dans le cadre de cette invention concerne un procédé par lequel un composé comprenant un composé aromatique présentant un substituant d’halogène radioactif et l’amine ou la phosphine qui y sont liées peut être produit à un rendement réalisable. La solution proposée consiste en un alcool contenant un halogène radioactif et présentant une structure comprenant un composé aromatique dans lequel un ou plusieurs atomes d’hydrogène ont été remplacés par un halogène radioactif et un groupe hydroxy lié au composé par un groupe alkylène, on le fait directement réagir avec différentes amines et phosphines dans des conditions acides. L’utilisation de ce procédé permet de réduire le nombre d’étapes à effectuer après le marquage avec un halogène radioactif et peut élever le rendement du composé cible.
PCT/JP2006/309303 2005-05-10 2006-05-09 Procede de production d’un compose organique marque avec un halogene radioactif Ceased WO2006121035A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2005-136976 2005-05-10
JP2005136976A JP2006315958A (ja) 2005-05-10 2005-05-10 放射性ハロゲン標識有機化合物の製造方法

Publications (1)

Publication Number Publication Date
WO2006121035A1 true WO2006121035A1 (fr) 2006-11-16

Family

ID=37396543

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2006/309303 Ceased WO2006121035A1 (fr) 2005-05-10 2006-05-09 Procede de production d’un compose organique marque avec un halogene radioactif

Country Status (3)

Country Link
JP (1) JP2006315958A (fr)
TW (1) TW200720284A (fr)
WO (1) WO2006121035A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011003591A1 (fr) 2009-07-10 2011-01-13 Bayer Schering Pharma Aktiengesellschaft Utilisation d’une chromatographie liquide de faible à moyenne pression pour la purification de traceurs radioactifs
CN102898470A (zh) * 2012-11-02 2013-01-30 北京师范大学 一类新型有机膦化合物及其制备方法和应用
WO2016072104A1 (fr) * 2014-11-05 2016-05-12 国立大学法人東北大学 Composé de phosphonium et son procédé de production

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003065882A2 (fr) * 2002-02-06 2003-08-14 The Johns Hopkins University Technologie d'imagerie de diagnostique non invasif pour les dysfonctionnements de mitochondries a l'aide de sels lipophiles radiomarques

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003065882A2 (fr) * 2002-02-06 2003-08-14 The Johns Hopkins University Technologie d'imagerie de diagnostique non invasif pour les dysfonctionnements de mitochondries a l'aide de sels lipophiles radiomarques

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
GUILLAUMEL J. ET AL.: "Recherches sur les derives nitres d'interet biologique", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 18, no. 5, 1983, pages 431 - 436, XP003002665 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011003591A1 (fr) 2009-07-10 2011-01-13 Bayer Schering Pharma Aktiengesellschaft Utilisation d’une chromatographie liquide de faible à moyenne pression pour la purification de traceurs radioactifs
CN102898470A (zh) * 2012-11-02 2013-01-30 北京师范大学 一类新型有机膦化合物及其制备方法和应用
CN102898470B (zh) * 2012-11-02 2014-12-10 北京师范大学 一类新型有机膦化合物及其制备方法和应用
WO2016072104A1 (fr) * 2014-11-05 2016-05-12 国立大学法人東北大学 Composé de phosphonium et son procédé de production
JPWO2016072104A1 (ja) * 2014-11-05 2017-08-10 国立大学法人東北大学 ホスホニウム化合物およびその製造方法

Also Published As

Publication number Publication date
JP2006315958A (ja) 2006-11-24
TW200720284A (en) 2007-06-01

Similar Documents

Publication Publication Date Title
JP5695540B2 (ja) 触媒性放射性フッ素化
JP5732198B2 (ja) 放射性フッ素標識有機化合物の製造方法
US10098974B2 (en) Catalytic radiofluorination
CN112175025B (zh) 一种含苯环的葡萄糖衍生物及其应用
CN111138504A (zh) 一种99mTc-CNPEDG配合物及其制备方法和应用
CN108299482B (zh) F-bpa及其中间体合成方法、中间体及其应用
CN113583066A (zh) 一种甘露糖衍生物及其应用
CN110183493B (zh) 一种99m锝标记配合物及其在诊断非小细胞肺癌中的应用
US9017724B2 (en) Catalytic radiofluorination
WO2006121035A1 (fr) Procede de production d’un compose organique marque avec un halogene radioactif
PL239934B1 (pl) Pochodne inhibitorów PSMA do znakowania ⁹⁹ᵐTc poprzez HYNIC, zestaw radiofarmaceutyczny, preparat radiofarmaceutyczny oraz ich zastosowanie w diagnostyce raka prostaty
KR102084472B1 (ko) 다양한 압타머에 적용 가능한 방사성동위원소 표지된 핵산 구조체 개발 및 표지방법
WO1999020316A1 (fr) Radiotraceurs d'emission monophotonique et leurs methodes d'utilisation
CN108358958B (zh) 中间体、中间体合成方法及应用
KR20110023707A (ko) 이작용기성 테트라아자 거대고리 화합물의 제조방법 및 용도
CN116987128B (zh) 一种含(D)-α-亚氨基酸修饰的甘露糖衍生物及其应用
WO2011160216A2 (fr) Composés utiles en imagerie et en thérapie
CN109438265B (zh) 一种与棕色脂肪组织具有亲和力的化合物及其制备方法和应用
CN108409759B (zh) 中间体、中间体合成方法及应用
WO2008106442A1 (fr) Synthèse de [18f] fluorométhyle benzène en utilisant du pentafluorobenzènesulfonate de benzyle
CN108409760A (zh) 中间体、中间体合成方法及应用
CN119118880A (zh) 一种f-18标记的psma抑制剂及其制备方法与应用
CN120230160A (zh) 一种含l-脯氨酸修饰的葡萄糖衍生物及其应用
AU2012205161B2 (en) Catalytic radiofluorination
JP2014122177A (ja) 放射性ヨード標識前駆体の製造方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

NENP Non-entry into the national phase

Ref country code: RU

122 Ep: pct application non-entry in european phase

Ref document number: 06746134

Country of ref document: EP

Kind code of ref document: A1