US 2015/0030540 A1 · Imaging agents for detecting neurological dysfunction

Abstract

Disclosed here in are compounds and methods of diagnosing Alzheimer's Disease or a predisposition thereto in a mammal, the method comprising administering to the mammal a diagnostically effective amount of a radiolabeled compound, wherein the compound is selected from the group consisting of radiolabeled carbazoles and derivatives thereof and triazoles derivatives, allowing the compound to distribute into the brain tissue, and imaging the brain tissue, wherein an increase in binding of the compound to the brain tissue compared to a normal control level of binding indicates that the mammal is suffering from or is at risk of developing Alzheimer's Disease.

Claims5

Dependent claims

1-43. (canceled)

A compound selected from the group consisting of:

N-(3-fluoropropyl)-3-methyl-5H-pyrido[3,2-b]indol-7-amine;
7-(2-fluoroethoxy)-1-methyl-9H-pyrido[3,4-b]indole;
7-(2-fluoroethoxy)-9H-pyrido[3,4-b]indole;
N-(3-fluoropropyl)-9H-pyrido[3,4-b]indol-7-amine;
7-(2-fluoroethoxy)-5H-pyrido[3,2-b]indole;
7-(2-fluoroethoxy)-2-methoxy-5H-pyrido[3,2-b]indole;
7-(2-fluoroethoxy)-3-methyl-5H-pyrido[3,2-b]indole;
N-(2-fluoroethyl)-N-methyl-9H-pyrido[3,4-b]indol-7-amine;
N-(2-fluoroethyl)-N-methyl-5H-pyrido[3,2-b]indol-7-amine;
N-(2-fluoroethyl)-N,3-dimethyl-5H-pyrido[3,2-b]indol-7-amine;
N-(2-fluoroethyl)-2-methoxy-N-methyl-5H-pyrido[3,2-b]indol-7-amine;
N-(3-fluoropropyl)-5H-pyrido[3,2-b]indol-7-amine;
N-(3-fluoropropyl)-3-methyl-5H-pyrido[3,2-b]indol-7-amine;
N-(3-fluoropropyl)-2-methoxy-5H-pyrido[3,2-b]indol-7-amine;
7-(2-(2-fluoroethoxy)ethoxy)-3-methyl-5H-pyrido[3,2-b]indole;
7-(4-(2-fluoroethoxy)phenyl)-5H-pyrido[3,2-b]indole;
7-(6-fluoropyridin-3-yl)-5H-pyrido[3,2-b]indole;
N-(2-fluoroethyl)-N-methyl-4-(3-methyl-5H-pyrido[3,2-b]indol-7-yl)aniline;
7-(4-fluoropiperidin-1-yl)-3-methyl-5H-pyrido[3,2-b]indole;
7-(3-fluoropropoxy)-5H-pyrido[4,3-b]indole;
4-(7-(3-fluoropropoxy)-5H-pyrido[3,2-b]indol-3-yl)aniline;
(E)-7-(3-fluoropropoxy)-3-(prop-1-enyl)-5H-pyrido[3,2-b]indole;
3-cyclopropyl-7-(3-fluoropropoxy)-5H-pyrido[3,2-b]indole;
7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-5H-pyrido[4,3-b]indole;
7-(2-(2-fluoroethoxy)ethoxy)-5H-pyrido[4,3-b]indole;
7-((2-(2-fluoroethoxy)ethoxy)methyl)-5H-pyrido[4,3-b]indole;
7-(6-fluoropyridine-3-yl)-5-methyl-H-pyrido[4,3-b]indole;
8-fluoro-7-(2-fluoroethoxy)3-methyl-5H-pyrido[3,2-b]indole;
6-fluoro-7-(2fluoroethoxy)3-methyl-5H-pyrido[3,2-b]indole;
8-fluoro-7-methoxy-3-methyl-5H-pyrido[3,2-b]indole;
7-fluoro-3-methyl-5H-pyrrolo[2,3-b:4,5-b′]dipyridine;
2-fluoro-7-methoxy-5H-pyrido[3,2-b]indole;
7-(2-(2-(2-Fluoroethoxy)ethoxy)ethoxy)-3-methyl-5H-pyrrolo[2,3b:4,5-b′]dipyridine;
7-(3-fluoropropyl)-5H-pyrido[4,3-b]indole;
7-(3-fluoropropyl)-3-methyl-5H-pyrido[3,2-b]indole;
7-(2-fluoroethyl)-5H-pyrido[4,3-b]indole;
7-(2-(2-(2-fluoroethoxy)ethoxy)ethyl)-5H-pyrido[4,3-b]indole;
6-(2-fluoroethoxy)-5H-pyrido[3,2-b]indole;
8-(2-fluoroethoxy)-5H-pyrido[3,2-b]indole;
3-(6-fluoro-3-pyridyl)-5H-pyrido[3,2-b]indole;
3-[2-[2-(2-fluoroethoxy)ethoxy]ethoxy]-5H-pyrido[3,2-b]indole;
7-(3-fluoropropyl)-5H-pyrido[4,3-b]indole;
3-(6-fluoro-3-pyridyl)-5H-pyrido[3,2-b]indol-7-ol;
7-(3-fluoropropoxy)-3-methyl-5H-pyrido[3,2-b]indole;
2-(2-fluoroethoxy)-9H-carbazole;
2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-carbazole;
7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-N-methyl-9H-carbazol-2-amine;
tert-butyl 2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-carbazole-9-carboxylate;
2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9-methyl-9H-carbazole;
7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-N,N-dimethyl-9H-carbazol-2-amine;
7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-N-methyl-9H-carbazol-3-amine;
N-(7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-carbazol-2-yl)acetamide;
N-(7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-carbazol-2-yl)formamide;
6-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9-(methoxymethyl)-N,N-dimethyl-9H-carbazol-3-amine;
N-(7-(2-fluoroethoxy)-9H-carbazol-2-yl)formamide;
N-(2-fluoroethyl)-6-methoxy-9H-carbazol-3-amine;
7-((4-fluorobutyl)(methyl)amino)-9H-carbazol-2-ol;
7-((2-fluoroethyl)(methyl)amino)-9H-carbazol-2-ol;
7-(2-fluoroethylamino)-9H-carbazol-2-ol;
1-(2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-carbazol-9-yl)ethanone;
7-((2-(2-(2-fluoroethoxy)ethoxy)ethyl)(methyl)amino)-9H-carbazol-2-ol;
7-(2-fluoroethoxy)-N-methyl-9H-carbazol-2-amine;
(2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-carbazol-9-yl)(phenyl)methanone;
N-(7-(2-(2-fluoroethoxy)ethoxy)-9H-carbazol-2-yl)formamide;
7-(2-fluoroethoxy)-9H-carbazol-2-ol;
7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-carbazol-2-ol;
N-(4-(7-amino-9H-carbazol-2-yloxy)phenyl)-2-fluoropropanamide;
7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-pyrido[2,3-b]indole;
2-fluoro-N-(4-(7-(methylamino)-9H-carbazol-2-yloxy)phenyl)propanamide;
N-(7-(4-fluorobutoxy)-9H-carbazol-2-yl)formamide;
tert-butyl 2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-pyrido[2,3-b]indol-7-ylcarbamate;
2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-pyrido[2,3-b]indol-7-amine;
9-(2-fluoroethyl)-9H-carbazol-2-ol;
N-(2-fluoroethyl)-7-(2-(2-(2-methoxyethoxyl)ethoxy)ethoxy)-9H-carbazol-3-amine;
7-(2-fluoroethoxy)-N,N-dimethyl-9H-carbazol-2-amine;
1-(3,6-diamino-9H-carbazol-9-yl)-3-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)propan-1-one;
N-(2-fluoroethyl)-2-hydroxy-11H-benzo[a]carbazole-3-carboxamide;
2-(6-chloro-9H-carbazol-2-yl)-N-(2-fluoroethyl)propanamide;
and
2-(6-fluoro-9H-carbazol-2-yl)-N,N-dimethylpropanamide;
or pharmaceutically acceptable salts thereof,
wherein fluoro is optionally replaced with a radionuclide.

79 more elements

Dependencies are inferred from the claim text.

Facts

Application

14/513,486Filed 14 Oct 2014

Priority

14 Feb 2008

Published

29 Jan 2015

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

A61K 51/0455
Having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins: having six-membered rings with one nitrogen as the only ring hetero atom
A61K 51/0446
Having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins: having five-membered rings with one nitrogen as the only ring hetero atom,…
C07B 59/002
Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se: heterocyclic compounds
C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems

Family

Application61/066,101Us provisional application · filed 14 Feb 2008

Application12/372,717Continuation in part · filed 17 Feb 2009

Application61/489,284Us provisional application · filed 24 May 2011

Application13/477,095Continuation · filed 22 May 2012

Application14/513,486Continuation

Application13/477,095Continuation in part

US 2011/0091382 A1Published application

US 2012/0302755 A1Published application

US 8,318,132 B2Related patent

US 8,932,557 B2Related patent

US 2015/0030540 A1This patent

From the US filing history. Foreign family members aren’t listed.

Imaging agents for detecting neurological dysfunction

Life of this patent

Imaging agents for detecting neurological dysfunction

Life of this patent

Abstract

Claims5