18f fluoro-benzoyl labelled biological active coumpounds as diagnositic imaging agents as well as benzotriazol-1-yloxy-benzoyl, 2,5-dioxo-pyrrolidin-1-yloxy) benzoyl and trimethylammonio-benzoyl precu

A compound and chemical technology, which can be used in the introduction of heterocyclic compound isotopes, NMR/MRI contrast agents, radioactive carriers, etc., and can solve problems such as time-consuming

Inactive Publication Date: 2009-12-30
BAYER SCHERING PHARMA OY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This two-step method is time-consuming and requires multiple purification steps

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  • 18f fluoro-benzoyl labelled biological active coumpounds as diagnositic imaging agents as well as benzotriazol-1-yloxy-benzoyl, 2,5-dioxo-pyrrolidin-1-yloxy) benzoyl and trimethylammonio-benzoyl precu
  • 18f fluoro-benzoyl labelled biological active coumpounds as diagnositic imaging agents as well as benzotriazol-1-yloxy-benzoyl, 2,5-dioxo-pyrrolidin-1-yloxy) benzoyl and trimethylammonio-benzoyl precu
  • 18f fluoro-benzoyl labelled biological active coumpounds as diagnositic imaging agents as well as benzotriazol-1-yloxy-benzoyl, 2,5-dioxo-pyrrolidin-1-yloxy) benzoyl and trimethylammonio-benzoyl precu

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[0574] Azeotropically dry by heating at 110-120°C for 20-30 minutes under nitrogen flow in the presence of Kryptofix 222 (5 mg in 1.5 ml MeCN) and cesium carbonate (2.3 mg in 0.5 ml water) 18 F-fluoride (up to 40GBq). During this time, 3 x 1 ml MeCN was added and evaporated. After drying, a solution of the precursor (2 mg) in 150 μl DMSO was added. Seal the reaction vessel and heat at 50-70 °C for 5-15 minutes to achieve labeling. The reaction was cooled to room temperature and diluted with water (2.7ml). The crude reaction mixture was analyzed using analytical HPLC. The product was obtained by preparative radiation HPLC to obtain the desired 18 F labeled peptide.

[0575] In a fourth aspect, the present invention relates to a composition comprising a compound of general chemical formula I or II, more specifically formula IIA or IIB, or a pharmaceutically acceptable salt, hydrate, ester, amide, solvate thereof Or prodrug and further comprising a pharmaceutically acceptab...

Embodiment

[0605] Depends on part LG-O-(C 6 Y 1 Y 2 Y 3 Y 4 )-(??) The properties of the compound of general chemical formula I of the present invention can be synthesized. The peptide moieties of -A-B-D-P are conveniently prepared according to generally established techniques known in the art of peptide synthesis, such as solid phase peptide synthesis. They are a proven Fmoc-solid-phase peptide synthesis with alternating protection and deprotection. These methods are thoroughly discussed in the peptide literature. (Reference: "Fmoc Solid Phase Peptide Synthesis A practical approach", by W.C. Chan and P.D. White, Oxford University Press 2000) (For abbreviations, see Descriptions).

[0606] summary

[0607] Rink amide resin (0,68 mmol / g), carrying out peptide synthesis. If not indicated otherwise, all amino acid residues are L-amino acid residues.

[0608] Fmoc-deprotection (general approach)

[0609]The resin-bound Fmoc peptide was treated with 20% piperidine (v / v) in DMF for...

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Abstract

The present invention relates to radiolabelled substitute benzene compounds for diagnostic imaging. The present invention provides methods for preparation of such compounds, in particular, preparation of novel compounds which serve as precursors for <18>F-labeling, and the use of thus <18>F-labeled compounds for diagnostic imaging. Formula (A), wherein one of -Y1, -Y2, -Y3 Y4 and -Y5 is -A-B-D-P, wherein -A-B-D- is a bond or spacer, P is peptide, peptidomimetic, oligonucleotide or small molecule. K is LG-O or W, wherein: LG- is selected from the group comprising Formula (B), wherein T is H or Cl, Q is CH or N, K is absent or is C=O. W is radioactive or non-radioactive isotope of fluorine, more preferably <18>F.

Description

technical field [0001] The present invention relates to novel substituted benzene compounds which are obtainable as halogen-labelled, more particularly 18 F-labeled biologically active compounds, and each halogen-labeled, more specifically 18 F-labeled compounds, the preparation of said halogen-labeled, more specifically 18 F Labeled compounds, compositions comprising such compounds and their diagnostic imaging applications, kits comprising sealed vials containing a predetermined amount of such novel substituted benzene compounds, and for use as medicaments, Such compounds are useful as diagnostic imaging agents and most particularly as imaging agents for positron emission tomography (PET). Background technique [0002] In vivo scans using positron emission tomography (PET) have increased in recent years. PET is both a medical tool and a research tool. It is widely used in medical imaging of tumors and in finding metastasis in clinical oncology, as well as in the clinica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K49/04A61K49/08A61K31/7072A61K49/10A61K38/08A61K51/04C07D409/04C07D249/18C07D405/14C07D405/04C07K7/06C07K1/13C07K5/023C07K5/02
CPCC07K5/0202A61K51/08C07B59/002C07D249/18C07K1/13C07K5/0207
Inventor A·斯里尼瓦桑T·施特菲尔德
Owner BAYER SCHERING PHARMA OY
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