Triarylmethyl radicals

Patent metadata

Field	Value
Publication number	US-9381257-B2
Application number	US-201314414224-A
Country	US
Kind code	B2
Filing date	Jul 4, 2013
Priority date	Jul 13, 2012
Publication date	Jul 5, 2016
Grant date	Jul 5, 2016

Abstract

New radical compounds, useful in the field of MRI imaging of formula (I). The radical compounds are in particular new triarylmethyl (“trityl”) radicals which can be used as polarizing agents for polarizing a molecule in the DNP process.

First claim

The invention claimed is:

1. A radical of formula (I)

wherein
each R′ 1 -R′ 9 independently represents:
a straight or branched C 1 -C 6 alkyl group, optionally substituted with an aromatic group; or
a group of formula —(CH 2 ) n -A-R′″, wherein:
n is 1, 2 or 3;
A is —S—, —O—, —CO—, —CO—O—, —CO—NH—, —SO—, —SO 2 — or —SO 2 —NH—; and
R′″ is hydrogen or a straight or branched C 1 -C 4 alkyl group;

each R″ 1 -R″ 12 independently represents:
a straight or branched C 1 -C 6 alkyl group; or
a group of formula —(CH 2 ) n —B—R′″, wherein:
n is 1, 2 or 3;
B is —S—, —O—, —CO—, —CO—O— or —CO—NH—; and

R′″ is hydrogen or a straight or branched C 1 -C 4 alkyl group.

2. The radical of claim 1 wherein when A and/or B in the above formula represent a group —CO—O—, then R′″ is not hydrogen.

3. The radical according to claim 1 wherein one or more of the hydrogen atoms of the groups R′ and/or R″ are deuterium.

4. The radical according to claim 1 wherein each R′ 1 -R′ 9 independently represents a straight or branched C 1 -C 6 alkyl group, optionally substituted with an aromatic group or a group —(CH 2 ) n -A-R′″, where n and A are as defined in claim 1 and R′″ is a straight or branched C 1 -C 4 alkyl.

5. The radical according to claim 1 wherein each R″ 1 -R″ 12 independently represents a straight or branched C 1 -C 6 alkyl group or a group —(CH 2 ) n —B—R′″, where n and B are as defined in claim 1 and R′″ is a straight or branched C 1 -C 4 alkyl.

6. The radical according to claim 1 which has a formula selected from the group consisting of:

7. A dynamic nuclear polarization (DNP) preparation which comprises a 13 C-labelled compound in admixture with a radical of claim 1 .

8. The DNP preparation of claim 7 wherein said 13 C-labelled compound is an ester precursor of an magnetic resonance (MR) agent.

9. A DNP preparation which comprises a 13 C-labelled compound in admixture with a radical of claim 3 .

10. A DNP preparation which comprises a 13 C-labelled compound in admixture with a radical of claim 6 .

11. A method for preparing a polarized sample for MR imaging which comprises:
submitting a mixture comprising a 13 C-labelled compound and a radical according to claim 1 to DNP, to obtain a polarized sample;
dissolving said mixture in an aqueous carrier; and
removing the radical from the polarized sample.

12. A method for preparing a polarized sample for MR imaging which comprises:
submitting a mixture comprising a 13 C-labelled compound and a radical according to claim 6 to DNP, to obtain a polarized sample;
dissolving said mixture in an aqueous carrier; and
removing the radical from the polarized sample.

Assignees

• Bracco Imaging Spa

Inventors

• Jensen Pernille Rose
• Karlsson Magnus
• Lerche Mathilde H
• Napolitano Roberta
• Tedoldi Fabio
• Visigalli Massimo

Classifications

• G01R33/282

  Means specially adapted for hyperpolarisation or for hyperpolarised contrast agents, e.g. for the generation of hyperpolarised gases using optical pumping cells, for storing hyperpolarised contrast agents or for the determination of the polarisation of a hyperpolarised contrast agent · CPC title

• A61K49/10 Primary

  Organic compounds · CPC title

• C07F7/0814 Primary

  said ring is substituted at a C ring atom by Si · CPC title

• C07F7/0812

  comprising a heterocyclic ring · CPC title

• A61K49/20

  containing free radicals {, e.g. trityl radical for overhauser} · CPC title