PET Imaging agents

Patent metadata

Field	Value
Publication number	US-10450298-B2
Application number	US-201615544850-A
Country	US
Kind code	B2
Filing date	Jan 20, 2016
Priority date	Jan 20, 2015
Publication date	Oct 22, 2019
Grant date	Oct 22, 2019

Abstract

Preparation of novel 2-benzyl-5-methyl-2H-tetrazole derivatives of the formula (I) for use as PET imaging agents. The present invention relates to novel compounds of formula (I) their preparation and use as PET imaging agents for imaging techniques and diagnostics in the field of diseases and disorders mediated by or related to the enzyme autotaxin.

First claim

The invention claimed is:

1. A compound of the general Formula (I)

and/or a pharmaceutically acceptable salt thereof, wherein
R is halogen, —CF 3 , —OCF 3 , —OCH 3 , —CH 3 or CN; and
A is a pyridinyl or oxazolyl group substituted with at least one substituent selected from halo-(C 1-6 -alkyl), halo-(C 1-3 -alkyl)oxy(C 2-4 -alkyl), or halo-(C 1-3 -alkyl)oxy(C 2-4 -alkyl) oxy(C 2-4 -alkyl) wherein compound of formula (I) contains at least one atom chosen from 3 H, 18 F, 123 I, 124 I, 125 I, 127 I, 131 I, 11 C, or 14 C.

2. A compound according to claim 1 that contains 3 H.

3. A compound according to claim 1 wherein R is —CF 3 or —OCF 3 .

4. A compound according to claim 3 that contains at least one 18 F.

5. A compound according to claim 1 wherein R is halogen.

6. A compound according to claim 5 wherein R is chosen from 18 F, 19 F, 123 I 124 I, 125 I, 127 I or 131 I.

7. A compound according to claim 1 wherein A contains at least one of 18 F, 19 F, 123 I, 124 I, 125 I, 127 I or 131 I.

8. A compound according to claim 1 , wherein the carbon atom numbered “1” is chosen from 11 C, 12 C or 14 C.

9. A compound selected from the group consisting of

and/or a pharmaceutically acceptable salt thereof wherein compound contains at least one atom chosen from 3 H, 18 F, 123 I, 124 I, 131 I, 11 C, or 14 C.

10. A method for the detection of autotaxin in a subject in recognized need thereof, said method comprising: (i) administration of a radiolabelled compound of formula (I) according to claim 1 , or a pharmaceutically acceptable salt thereof to said subject; and (ii) detecting uptake of said compound by in vivo PET or SPECT imaging.

11. A composition comprising a compound according to claim 1 or a pharmaceutically acceptable salt thereof.

12. A composition according to claim 11 suitable for use in PET imaging.

Assignees

• Auberson Yves
• Briard Emmanuelle
• Le Grand Darren
• Oberhauser Berndt
• Novartis Ag

Inventors

• Auberson Yves
• Briard Emmanuelle
• Le Grand Darren
• Oberhauser Berndt

Classifications

• C07D401/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D413/12

  linked by a chain containing hetero atoms as chain links · CPC title

• A61K51/0474

  complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title

• C07B59/002

  Heterocyclic compounds · CPC title