Compounds for separation of rare earth elements and s-, p-, d- metals, method of separation, and use thereof

A rare earth element, compound technology, applied in the field of p-block, separation of rare earth elements and/or s-block, d-block metal compounds

Active Publication Date: 2020-08-07
有机生物化学公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Often, no single technique can provide satisfactory results and a combination of techniques must be used, with ion-exchange chromatography or extraction chromatography as the last step (Medvedev D.G. et al., (2012), Appl. Radiat. Isot. )》70(3), 423-429)

Method used

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  • Compounds for separation of rare earth elements and s-, p-, d- metals, method of separation, and use thereof
  • Compounds for separation of rare earth elements and s-, p-, d- metals, method of separation, and use thereof
  • Compounds for separation of rare earth elements and s-, p-, d- metals, method of separation, and use thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0126] Example 1: 2,2',2"-(10-((6-fluoropyridin-2-yl)methyl)-1,4,7,10-tetraazacyclododecane-1,4,7 - Preparation of triyl) triacetic acid (1)

[0127] And the filtrate was concentrated on a rotary evaporator. The resulting oil was purified on preparative HPLC (C18 column, acetonitrile / water gradient with 0.1% trifluoroacetic acid in the mobile phase). Fractions containing pure product as tert-butyl ester were combined, evaporated and dried under high vacuum. The residue was dissolved in neat trifluoroacetic acid (3 mL) and stirred at room temperature for 24 hours. Trifluoroacetic acid was evaporated on a rotary evaporator. The residue was dissolved in distilled water (2 ml), loaded onto a solid phase extraction cartridge (C18 reverse phase, 500 mg) and eluted with distilled water (10 mL). The eluate was lyophilized, redissolved in distilled water (2 mL) and lyophilized again to yield 199 mg of product (0.283 mmol, 84% yield relative to B) as a white fluffy solid.

[0128...

example 2

[0131] Example 2: 2,2',2"-(10-((6-chloropyridin-2-yl)methyl)-1,4,7,10-tetraazacyclododecane-1,4,7 - Preparation of triyl) triacetic acid (2)

[0132] 69% yield relative to 2-(bromomethyl)-6-chloropyridine).

[0133] 1 H NMR (D with internal dioxane reference 2 O,95℃,500MHz):δ H 3.28-3.35 (ring, m, 4H); 3.35-3.42 (ring, m, 4H); 3.51-3.60 (ring, m, 8H); 3.73 (CH 2 –COOH,s,4H); 4.13(CH 2 –COOH,s,2H); 4.56(CH 2 – aromatic, s, 2H); 7.63 (aromatic, d, 1H, 3 J HH =8Hz); 7.64 (aromatic, d, 1H, 3 J HH =8Hz); 8.00(aromatic,t,1H, 3 J HH = 8Hz); 13 C{ 1 H} NMR (D with internal dioxane reference 2 O,95℃,125MHz):δ C 49.7 (ring, s); 49.9 (ring, s); 51.5 (ring, s); 51.9 (ring, s); 54.4 (CH 2 –COOH,s); 55.5(CH 2 –COOH,s); 58.6 (CH 2 – aromatic, s); 124.4 (aromatic, s); 126.1 (aromatic, s); 142.2 (aromatic, s); 151.7 (aromatic, s); 152.2 (aromatic, s); ,s); 172.9(CO,s). HRMS(ESI)m / z:[(M–H) – ](C 20 h 29 ClN 5 o 6 ) calculated value: 470.1812, measured value: 470.1811....

example 3

[0134] Example 3: 2,2',2"-(10-((6-bromopyridin-2-yl)methyl)-1,4,7,10-tetra

[0135] The reaction of produced approximately 179 mg of product (0.232 mmol, 69% yield relative to B) as a white fluffy solid.

[0136] 1 H NMR (D with internal dioxane reference 2 O,95℃,500MHz):δ H 3.31-3.38 (ring, m, 4H); 3.38-3.45 (ring, m, 4H); 3.52-3.62 (ring, m, 8H); 3.76 (CH 2 –COOH,s,4H); 4.14(CH 2 –COOH,s,2H); 4.57(CH 2 – aromatic, s, 2H); 7.71 (aromatic, d, 1H, 3 J HH =8Hz); 7.82 (aromatic, d, 1H, 3 J HH = 8Hz); 7.92 (aromatic, t, 1H, 3 J HH = 8Hz); 13 C{ 1 H} NMR (D with internal dioxane reference 2 O,95℃,125MHz):δ C 49.8 (ring, s); 50.0 (ring, s); 51.5 (ring, s); 51.9 (ring, s); 54.4 (CH 2 –COOH,s); 55.4(CH 2 –COOH,s); 58.6 (CH 2– aromatic, s); 125.0 (aromatic, s); 130.0 (aromatic, s); 141.8 (aromatic, s); 142.2 (aromatic, s); 152.8 (aromatic, s); 170.1 (CO ,s); 172.8(CO,s). HRMS(ESI)m / z:[(M–H) – ](C 20 h 29 BrN 5 o 6 ) Calculated: 514.1307, Measured: 514.1304. E...

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Abstract

The present invention relates to compounds of general formula (I) for chromatographic separation of rare earth elements and / or s-, p-, d- metals, as well as to the method of the separation of rare earth elements.

Description

technical field [0001] The present invention relates to: compounds suitable for separating rare earth elements and / or s-block, p-block, d-block metals; a method for chromatographically separating rare-earth elements and / or s-block, p-block, d-block metals from a mixture of metal ions , at least one metal ion in the metal ion is a rare earth metal selected from the following: Ce, Dy, Er, Eu, Gd, Ho, La, Lu, Nd, Pr, Pm, Sm, Sc, Tb, Tm, Yb and Y, alkaline earth metals, Al, Ga, In, Tl, Sn, Pb or transition metals; and use of said compounds for extracting and separating rare earth elements and / or s-block, p-block, d-block metals from mixtures . Background technique [0002] Radionuclides of metal elements are increasingly used in nuclear medicine, mainly for the diagnosis and therapy of neoplastic diseases. There is increasing interest in targeted radiotherapy using targeting carriers (peptides, antibodies, etc.) to specifically deliver radioactive payloads to cancer tissues. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/06C07D403/06C07D405/06C07D257/02B01D15/08
CPCB01D15/08C07D401/06C07D403/06C07D405/06C07D257/02C22B59/00
Inventor M·波拉赛克
Owner 有机生物化学公司
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