CS257193B1 - Process for the preparation of iodine-labeled 1- (4-iodophenyl) -2-isopropylaminopropane - Google Patents
Process for the preparation of iodine-labeled 1- (4-iodophenyl) -2-isopropylaminopropane Download PDFInfo
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- CS257193B1 CS257193B1 CS869284A CS928486A CS257193B1 CS 257193 B1 CS257193 B1 CS 257193B1 CS 869284 A CS869284 A CS 869284A CS 928486 A CS928486 A CS 928486A CS 257193 B1 CS257193 B1 CS 257193B1
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Abstract
Způsob přípravy 1-/4-jodfenyl/- -2-izopropylaminopropanu značeného radioaktivními izotopy jodu vzorce II spočívá v tom,»že se na 1-Í4-/2-(2-propylamino)- propyl/benzenazojpiperidin vzorce I působí ve směsi acetonu s trifluoroctovou kyselinou radioaktivně značeným jodidem alkalického kovu. Látka II se používá k scintigrafickému zobrazování mozku a diagnostice mozkových onemocnění.The method for preparing 1-(4-iodophenyl)-2-isopropylaminopropane labeled with radioactive iodine isotopes of formula II consists in treating 1-(4-[2-(2-propylamino)propyl]benzenezoylpiperidine of formula I in a mixture of acetone with trifluoroacetic acid and radioactively labeled alkali metal iodide. Substance II is used for scintigraphic imaging of the brain and diagnosis of brain diseases.
Description
Vynález se týká způsobu regiospecifické přípravy 1-/4-jodfenyl/-2-isopropylaminopropanu 123 125 131 vzorce II značeného radioaktivními izotopy jodu / I, I a 1/. Tyto amfetaminové deriváty se používají k scintigrafickému zobrazování mozku a tudíž v diagnostice mozkových chorob.The invention relates to a process for the region-specific preparation of 1- (4-iodophenyl) -2-isopropylaminopropane 123 125 131 of formula II labeled with radioactive isotopes of iodine (I, I and 1). These amphetamine derivatives are used for scintigraphic imaging of the brain and thus in the diagnosis of brain diseases.
Látka vzorce II byla zatím připravena různými vícestupňovými pochody a radioaktivní izotop jodu byl do molekuly zaváděn různými způsoby izotopové výměny /Knust E. J. et al.i Nuklearmedizin 23, 31 /1984/; Baldwin R. M. et al.: Eur. Pat. Appl. 11 858, 32 pp /1980/; Carlsen L. et al.: Eur. J. Nucl. Med. 7 280 /1982/; Mertens J. J. R. et al.: J. Labelled. Compd. Radiopharm. 22, 89 /1985/; Duterte D. et al.: J, Labelled. Compd. Radiopharm. 20,The compound of formula II has so far been prepared by various multistep processes and the radioactive isotope of iodine has been introduced into the molecule by various isotopic exchange methods (Knust E.J. et al. Nuclearmedizine 23, 31 (1984)); Baldwin R. M. et al., Eur. Pat. Appl. 11,858,32 pp (1980); Carlsen L. et al., Eur. J. Nucl. Copper. 7,280 (1982); Mertens, J. J. R. et al., J. Labeled. Compd. Radiopharm. 22, 89 (1985); Duterte D. et al .: J, Labeled. Compd. Radiopharm. 20,
149 /1983/ a Mangner T. J. et al.: j. Org. Chem. 47, 1 484 /1982//. Vesměs se jedná o zdlou123 havé a technicky náročné procesy s omezeným použitím krátkodobých izotopů /zejména 1/.149 (1983) and Mangner T. J. et al .: J. Org. Chem. 47, 1484 (1982). All of these are lengthy123 technically demanding processes with limited use of short-lived isotopes (especially 1).
Jako výchozí látky jsou v nich použity 4-jodfenyloctové kyseliny, benzylmethylketon, případně 4-jodamfetamin.The starting materials used are 4-iodophenylacetic acids, benzylmethyl ketone or 4-iodamphetamine.
Uvedené nevýhody řeší způsob přípravy 1-/4-jodfenyl/-2-isopropylaminopropanu vzorce II podle tohoto vynálezu, jehož podstata spočívá v dvacetiminutovém míchání roztoku l-{4-/2-(2-propylamino)propyl(-benzenazojpiperidinu vzorce I ve směsi acetonu a trifluoroctové kyseliny s radioaktivně značeným jodidem alkalického kovu při teplotě místnosti. Látka vzorce II se isoluje z reakční směsi chromatograficky.These disadvantages are solved by a process for the preparation of 1- (4-iodophenyl) -2-isopropylaminopropane of the formula II according to the invention, which consists in stirring for 20 minutes a solution of 1- {4- / 2- (2-propylamino) propyl (-benzenazo-piperidine) of acetone and trifluoroacetic acid with radiolabeled alkali metal iodide at room temperature The compound of formula II is isolated from the reaction mixture by chromatography.
Látka vzorce II byla již v literatuře popsána /například Carlsen L. et al.: Eur. J. Nucl. Med. 7, 280 /1982//. Identita připravené látky II byla zajištěna obvyklými analytickými a spektrálními metodami. Obj. t.v. 0,05 90 až 91 °C; hydroohlorid t.t. 155 až 157,5 °C (ethanol - voda); 1H NMR (C2 HCip: 1,0 d (6 H, 2 CH3>; 1,055 (3 H, CH3) ; 2,2 až 3,2 m (4 H, 2 CH, CH2); 7,12 a 7,38 (AÁBÉ, 4 H, JAB + JAg = 8,6 Hz). Hmotnostní spektrum, m/z (%): 303 <M+, 5), 288 (11), 245 (19), 217 (82), 128 (35) u7 (30), 91 (37), 90 (51), 86 (100)., (55).The compound of formula II has already been described in the literature (for example, by Carlsen L. et al., Eur.). J. Nucl. Copper. 7, 280 (1982) //. The identity of the prepared substance II was ensured by usual analytical and spectral methods. Order no. t 0.05 90-91 ° C; Hydrochloride mp 155-157.5 ° C (ethanol-water); 1 H NMR (C 2 H 2 O 2 : 1.0 d (6 H, 2 CH 3 ); 1.055 (3 H, CH 3 ); 2.2 to 3.2 m (4 H, 2 CH, CH 2 ); , 12 and 7.38 (AABE, 4 H, J AB + J A = 8.6 Hz) Mass spectrum, m / z (%): 303 (M + , 5), 288 (11), 245 ( 19), 217 (82), 128 (35) and 7 (30), 91 (37), 90 (51), 86 (100)., (55).
Způsob podle vynálezu umožňuje přípravu v jednoduchém vybavení klinických a biologických laboratoří a přípravu těsně před vlastní aplikací.The method according to the invention allows preparation in simple equipment of clinical and biological laboratories and preparation just before the actual application.
Dále je uveden příklad přípravy látky II z látky I v neaktivní a aktivní formě. Tyto příklady jsou pouhou ilustrací možnosti vynálezu, avšak není jejich účelem popisovat všechny možnosti vynálezu vyčerpávajícím způsobem.The following is an example of the preparation of compound II from compound I in inactive and active form. These examples are merely illustrative of the possibility of the invention, but are not intended to describe all the possibilities of the invention in a comprehensive manner.
PřikladlHe did
125125
K ochlazené směsi jodidu sodného /1,83 mg, 12,1 jimol/ a Na I /0,57 MBq, bez nosiče, Amersham/ v 60 jíl vody byla přidána kyselina trifluoroctová /5 jíl/ a triazen I /5 mg, 11,6 ,nmol·/ v acetonu /100 pl/ za míchání. Po 20min míchání za teploty místnosti byl přidán roztok thiosíranu sodného /1 M, 10 jal/ a směs byla odpařena do sucha. Odparek byl extrahován acetonem /200 jal/, extrakt chromatografován na tenké vrstvě /Silufol/.v soustavě ethýlacetáť.methanol: :konc. hydroxid amonný - 17:2:1. Jodderivát II byl z chromatogramu eluován meth.anolem, získáno 0,37 MBq /66 % radiochemického výtěžku/.To the cooled mixture of sodium iodide (1.83 mg, 12.1 µmol) and Na I (0.57 MBq, unsupported, Amersham) in 60 µl of water was added trifluoroacetic acid (5 µl) and triazene I (5 mg, 11 µl). 1.6 nmol · in acetone (100 µl) with stirring. After stirring at room temperature for 20 min, sodium thiosulfate solution (1 M, 10 µL) was added and the mixture was evaporated to dryness. The residue was extracted with acetone (200 µl), the extract was thin layer chromatographed (Silufol) in ethyl acetate: methanol: conc. ammonium hydroxide - 17: 2: 1. The iodo derivative II was eluted from the chromatogram with methanol, yielding 0.37 MBq (66% radiochemical yield).
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS869284A CS257193B1 (en) | 1986-12-15 | 1986-12-15 | Process for the preparation of iodine-labeled 1- (4-iodophenyl) -2-isopropylaminopropane |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS869284A CS257193B1 (en) | 1986-12-15 | 1986-12-15 | Process for the preparation of iodine-labeled 1- (4-iodophenyl) -2-isopropylaminopropane |
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| Publication Number | Publication Date |
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| CS928486A1 CS928486A1 (en) | 1987-09-17 |
| CS257193B1 true CS257193B1 (en) | 1988-04-15 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS869284A CS257193B1 (en) | 1986-12-15 | 1986-12-15 | Process for the preparation of iodine-labeled 1- (4-iodophenyl) -2-isopropylaminopropane |
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1986
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| CS928486A1 (en) | 1987-09-17 |
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