Radiolabeled cannabinoid receptor 2 ligand

Patent metadata

Field	Value
Publication number	US-10227308-B2
Application number	US-201715443894-A
Country	US
Kind code	B2
Filing date	Feb 27, 2017
Priority date	Oct 27, 2014
Publication date	Mar 12, 2019
Grant date	Mar 12, 2019

Abstract

The present invention relates to a compound of formula (I)

wherein R 1 is defined as in the description and in the claims. The compound of formula (I) can be used as radiolabeled ligand.

First claim

We claim:

1. A compound of formula (I)

wherein R 1 is a methyl group and wherein at least one of the atoms of the methyl group of R 1 is replaced with a radionuclide independently selected from the group consisting of [ 3 H], [ 11 C] and [ 14 C].

2. The compound according to claim 1 , wherein R 1 is C[ 3 H] 3 , [ 11 C]H 3 or [ 14 C]H 3 .

3. A pharmaceutical composition comprising a compound according to claim 1 .

4. A process for the manufacture of a compound according to claim 1 comprising reacting a compound of formula (A)

in the presence of [ 3 H]-methyl 4-nitrobenzenesulfonate, [ 3 H]-methyl iodide, [ 11 C]-methyl triflate, [ 11 C]-methyl iodide, [ 11 C]-methyl 4-nitrobenzenesulfonate, [ 14 C]-methyl triflate, [ 14 C]-methyl iodide or [ 14 C]-methyl 4-nitrobenzenesulfonate.

5. The compound according to claim 1 , wherein at least one of the hydrogen atoms of the methyl group of R 1 is replaced with [ 3 H].

6. The compound according to claim 1 , wherein the compound is (NE)-N-[5-tert-butyl-2-(cyclobutylmethyl)-1-(tritritiomethyl)pyrazol-3-ylidene]-2-(2-hydroxy-2-methyl-propoxy)-5-(trifluoromethyl)benzamide, having the formula:

7. The compound according to claim 1 , wherein the compound is (NE)-N-[5-tert-butyl-2-(cyclobutylmethyl)-1-([ 14 C]methyl)pyrazol-3-ylidene]-2-(2-hydroxy-2-methyl-propoxy)-5-(trifluoromethyl)benzamide, having the formula:

8. The compound according to claim 1 , wherein the compound is (NE)-N-[5-tert-butyl-2-(cyclobutylmethyl)-1-([ 11 C]methyl)pyrazol-3-ylidene]-2-(2-hydroxy-2-methyl-propoxy)-5-(trifluoromethyl)benzamide, having the formula:

Assignees

• Hoffmann La Roche
• Eidgenoessische Technische Hochschule Zuerich
• Univ Zuerich
• Eidgenoessische Technische Hochschule Zuercih

Inventors

• Ametamey Simon M
• Fingerle Juergen
• Gobbi Luca
• Grether Uwe
• Haider Ahmed
• Hartung Thomas
• Mu Linjing
• Nicholls Leo
• Rogers-Evans Mark
• Ullmer Christoph

Classifications

• A61P37/06

  Immunosuppressants, e.g. drugs for graft rejection · CPC title

• A61P9/10

  for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis · CPC title

• A61P9/04

  Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure · CPC title

• A61P9/00

  Drugs for disorders of the cardiovascular system · CPC title

• A61P3/10

  for hyperglycaemia, e.g. antidiabetics · CPC title