IP Library › Patent Application 14513486

Patent Application

App. No. 14/513,486

Imaging agents for detecting neurological dysfunction

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Patent No.: US None
App. No.: 14/513,486

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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.

Claims (92)

1 - 43 . (canceled)

44 . 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.

45 . The compound of claim 44 , wherein fluoro is 18 F.

46 . A compound selected from the group consisting of:

7-(6-nitro-3-pyridyl)-5H-pyrido[4,3-b]indole;

7-(2-nitroethyl)-5H-pyrido[4,3-b]indole;

3-methyl-7-(2-nitroethoxy)-5H-pyrido[3,2-b]indole;

7-(3-nitropropyl)-5H-pyrido[4,3-b]indole; and

6′-fluoro-5-nitro-6-phenyl-3,3′-bipyridine;

or pharmaceutically acceptable salts thereof.

47 . A method of diagnosing Alzheimer's disease or a predisposition in a mammal comprising: a) administering to the mammal a diagnostically effective amount of a radiolabeled compound of claim 45 ; b) allowing the compound to distribute to the brain tissue; and c) imaging the brain tissue.