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Conjugates of macrocyclic metal complexes with biomolucules and utilization thereof for producing agents for use in NMR diagnosis and radiodiagnosis and radiotherapy

A technology of biomolecules and conjugates, which is used in in vivo radioactive preparations, preparations for in vivo experiments, and medical preparations with inactive ingredients, etc.

Inactive Publication Date: 2007-02-28
SCHERING AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, the possibility remains that the contrast agent can be configured to accumulate selectively in the desired target structure

Method used

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  • Conjugates of macrocyclic metal complexes with biomolucules and utilization thereof for producing agents for use in NMR diagnosis and radiodiagnosis and radiotherapy
  • Conjugates of macrocyclic metal complexes with biomolucules and utilization thereof for producing agents for use in NMR diagnosis and radiodiagnosis and radiotherapy
  • Conjugates of macrocyclic metal complexes with biomolucules and utilization thereof for producing agents for use in NMR diagnosis and radiodiagnosis and radiotherapy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0141] a) 10-[4-(benzyloxycarbonyl)-1-methyl-2-oxo-3-azetidine]-1,4,7-α, α′, α″-trimethyl- 1,4,7-tris-(benzyloxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane

[0142] 25 g (81.1 mmol) of 2-bromopropionylglycine-benzyl ester (Example 1e of WO 98 / 24774) were added to 27.9 g (162.2 mol) of 1,4,7,10-tetraazacyclododeca The latter had been dissolved in 300 ml of chloroform and then stirred overnight at room temperature. 250 ml of water were added, the organic phase was separated and then washed twice with 200 ml of water each. The organic phase was dried over magnesium sulfate and evaporated to dryness in vacuo. The residue was chromatographed on silica gel (solvent: chloroform / methanol / 25% ammonia=10 / 5 / 1). The thus obtained 1-[4-(benzyloxycarbonyl)-1-methyl-2-oxo-3-azetibutyl]-1,4,7,10-tetraazacyclododecane ( 19.6 g; 50 mmol; 62% of theory) and a solution of 60 ml (0.35 mol) of N-ethyldiisopropylamine in 200 ml of dichloromethane were added to 62.45 g (0.2 mol) of 2-(trifluor...

Embodiment 2

[0161]a) 10-[4-(Benzyloxycarbonyl)-1-methyl-2-oxo-3-azetidine]-1,4,7-α,α′,α″-tri(isopropyl base)-1,4,7-tris(benzyloxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane

[0162] 19.6 g (50 mmol) of 1-[4-(benzyloxycarbonyl)-1-methyl-2-oxo-3-azetibutyl]-1,4,7, which was used as an intermediate in Example 1a , a solution of 10-tetraazacyclododecane and 60ml (0.35mol) of N-ethyldiisopropylamine in 200ml of dichloromethane was added to 68.1g (0.2mol) of 2-(trifluoromethanesulfonyloxy A solution of benzyl isovalerate (Walker et al., Tetrahedron (1997), 53(43), 14591) in 400 ml of dichloromethane was stirred at reflux for 6 hours and then at room temperature overnight. Each was extracted 3 times with 500 ml of water, the organic phase was dried over magnesium sulphate and evaporated to dryness. The residue is chromatographed on silica gel (solvent: dichloromethane / methanol: 20 / 1). Fractions containing product were combined and concentrated by evaporation.

[0163] Yield: 33.7 g (70% o...

Embodiment 3

[0181] a) 10-[4-(benzyloxycarbonyl)-1-methyl-2-oxo-3-azetidine]-1,4,7-α,α′,α″-tri(cyclohexyl )-1,4,7-tris(benzyloxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane

[0182] 19.6 g (50 mmol) of 1-[4-(benzyloxycarbonyl)-1-methyl-2-oxo-3-azetibutyl]-1,4,7, which was used as an intermediate in Example 1a , a solution of 10-tetraazacyclododecane and 60ml (0.35mol) of N-ethyldiisopropylamine in 200ml of dichloromethane was added to 76.1g (0.2mol) of 2-(trifluoromethanesulfonyl Oxy)-benzyl 2-cyclohexyl acetate (Qabar et al., Tetrahedron Letters (1998), 39(33), 5895) in a solution in 400 ml of dichloromethane was stirred at reflux for 6 hours and then at room temperature overnight. Each was extracted 3 times with 500 ml of water, the organic phase was dried over magnesium sulfate and evaporated to dryness. The residue is chromatographed on silica gel (solvent: dichloromethane / methanol: 20 / 1). Fractions containing product were combined and concentrated by evaporation.

[0183] Yield...

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Abstract

The invention relates to conjugates that consist of macrocyclic metal complexes with biomolecules and their production. The conjugates are suitable as contrast media in NMR diagnosis and radiodiagnosis as well as as agents for radiotherapy. High relaxivity is achieved by a special liganding of macrocyclic compounds, and a fine-tuning of the relaxivity is made possible.

Description

technical field [0001] The present invention relates to the subject matter characterized in the claims, namely, combinations of macrocyclic metal complexes. The conjugates are suitable for the preparation of agents for NMR diagnosis and radiodiagnosis, in particular contrast agents, and agents for radiotherapy. Background technique [0002] A prerequisite for specific and successful therapy is an accurate diagnosis. Specifically, in the field of diagnostics, the possibility of accurate diagnosis has increased very dramatically in recent years, such as NMR diagnostics and radiological diagnostics, whereby the anatomy can be physically seen with the naked eye selectively and with a high degree of accuracy details. In many cases, however, the corresponding structures can be visualized only by using contrast agents. In addition, there remains the possibility of configuring the contrast agent to accumulate selectively in the desired target structure. In this case, the accurac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K49/08A61K49/00A61K47/48A61K51/00C07D301/00
CPCA61K49/143A61K49/085A61K49/0002A61K49/14C07D257/02
Inventor 约翰内斯·普拉策克黑里贝特·施米特-维利希京特·米希尔托马斯·弗伦策尔德特勒夫·聚尔策汉斯·鲍尔贝恩德·拉杜切拉汉斯-约阿希姆·魏因曼海科·席尔默
Owner SCHERING AG
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