(Ethylene)-(propylene) - triaminepentaacetic acid derivatives, process for their production, and their use for the production of pharmaceutical agents
AssigneeSchering Corporation
InventorsLutz Lehmann, Matthias Friebe, Christoph-Stephan Hilger, Ulrich Niedballa, Johannes Platzek, Bernd Raduchel
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Abstract
The invention relates to (ethylene)-(propylene)-triaminepentaacetic acid derivatives that are substituted on both the ethylene bridge and the propylene bridge, as well as conjugates of these compounds with biomolecules. The compounds and conjugates are suitable as agents for NMR diagnosis and radiodiagnosis as well as for radiotherapy.
Claims19
Compounds of formula I
- 24
- in which
- Z stands for a hydrogen atom or a metal ion equivalent,
- A stands for a radical of formula
- 25
- in which positions α and β that are characterized by are bonded to any of the adjacent nitrogen atoms, R1 is a nitro group or a group that can enter into a reaction with a biomolecule, and
- B stands for a radical of formula
- 26
- in which n is 0 or 1, and R2, R3, R4, R51 R61 R71 R8 and R9, independently of one another, are selected from a hydrogen atom, a straight-chain or branched, saturated or unsaturated C1-6 alkyl group, which optionally can be substituted with 1 or 2 hydroxy groups and/or can contain 1 or 2 oxygen atoms, and an aralkyl group, whose aryl radical optionally can be substituted with an alkyl or alkoxy group, whereby two of radicals R2, R3, R4, R5, R6, R7, R8 and R9 can be part of a 5- or 6-membered ring, provided that at least one and at most four of radicals R2, R3, R4, R5, R6, R7, R8, and R9 are not hydrogen atoms, as well as salts thereof.
Compounds according to one of the preceding claims, in which R1 is selected from the group that consists of nitro, amino, isocyanate, isothiocyanate, hydrazine, semicarbazide, thiosemicarbazide, chloroacetamide, bromoacetamide, iodoacetamide, acylamino, maleimide, maleimidacylamino, activated esters, mixed anhydrides, azide, hydroxide, sulfonyl chloride and carbodiimide.
Compounds according to one of the preceding claims, in which 1 or 2 of the radicals R2, R3, R4, R5, R6, R7, R8 and R9 are selected from the group that consists of methyl, ethyl and benzyl, and the others of these radicals are hydrogen atoms.
Compounds according to one of the preceding claims, in which radicals R2, R3, R4, R5, R6, R7, R8 and R9 are selected such that B is symmetrical.
Compounds according to one of the preceding claims, in which n=0.
Compounds according to one of the preceding claims, in which at least two of radicals Z stand for a metal ion equivalent of a paramagnetic element of atomic numbers 21-29, 42, 44 and 58-70.
Dependencies are inferred from the claim text.