IP Library Granted Patent US 7,423,147
Granted Patent B2
US 7,423,147 · App. 11/095,398 · Granted Sep 9, 2008

Pyridine compounds as histamine H3 modulators

Assignee: Janssen Pharmaceutical, N.V.
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Quick Facts
Patent No.
US 7,423,147
App. No.
11/095,398
Granted
Sep 9, 2008
Kind
B2
Abstract

Certain non-imidazole heterocyclic compounds are Histamine H 3 modulators in the treatment of Histamine H 3 receptor mediated diseases.

Claims (59)

1. A compound selected from the group consisting of:

(4-Isopropyl-piperazin-1-yl)-(6-piperidin-1-ylmethyl-pyridin-3-yl)-methanone;

(4-Isopropyl-piperazin-1-yl)-(6-morpholin-4-ylmethyl-pyridin-3-yl)-methanone;

(4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethyl-pyridin-2-yl)-methanone;

2-Piperdin-1-ylmethyl-5-(3-piperdin-1-yl-propoxy)-pyridine;

4-[5-(3-Piperidin-1-yl-propoxy)-pyridin-2-ylmethyl]-morpholine;

5-Piperidin-1-ylmethyl-2-(3-piperidin-1-yl-propoxy)-pyridine;

4-[6-(3-Piperidin-1-yl-propoxy)-pyridin-3-ylmethyl]-morpholine;

2-(4-Piperidin-1-yl-but-1-ynyl)-5-piperidin-1-ylmethyl-pyridine;

(4-Isopropyl-piperazin-1-yl)-[6-(2-piperidin-1-yl-ethylamino)-pyridin-3-yl]-methanone;

(4-Isopropyl-piperazin-1-yl)-[6-(2-morpholin-4-yl-ethylamino)-pyridin-3-yl]-methanone;

(4-Isopropyl-piperazin-1-yl)-[6-(2-pyridin-2-yl-ethylamino)-pyridin-3-yl]-methanone;

{6-[(2-Diethylamino-ethyl)-methyl-amino]-pyridin-3-yl}-(4-isopropyl-piperazin-1-yl)-methanone;

(4-Isopropyl-piperazin-1-yl)-[6-(4-isopropyl-piperazin-1-yl)-pyridin-3-yl]-methanone;

4-[5-(4-Isopropyl-piperazine-1-carbonyl)-pyridin-2-yl]-piperazine-1-carboxylic acid ethyl ester;

(4-Isopropyl-piperazin-1-yl)-[6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-methanone;

(4-Isopropyl-piperazin-1-yl)-[2-(2-piperidin-1-yl-ethylamino)-pyridin-4-yl]-methanone;

(4-Isopropyl-piperazin-1-yl)-[2-(2-piperidin-1-yl-ethylamino)-pyridin-3-yl]-methanone;

3-(4-Piperidin-1-yl-but-1-ynyl)-5-piperidin-1-ylmethyl-pyridine;

4-[5-(4-Piperidin-1-yl-but-1-ynyl)-pyridin-3-ylmethyl]-morpholine;

2-(4-Piperidin-1-yl-but-1-ynyl)-6-piperidin-1-ylmethyl-pyridine;

4-[6-(4-Piperidin-1-yl-but-1-ynyl)-pyridin-2-ylmethyl]-morpholine;

(2-Methoxy-ethyl)-[6-(4-piperidin-1-yl-but-1-ynyl)-pyridin-2-ylmethyl]-amine;

(4-Isopropyl-piperazin-1-yl)-(6-piperidin-1-ylmethyl-pyridin-3-yl)-methanethione, and enantiomers, diasteriomers and pharmaceutically acceptable salts and amides thereof.

2. A compound of claim 1 selected from the group consisting of:

(4-Isopropyl-piperazin-1-yl)-(6-piperidin-1-ylmethyl-pyridin-3-yl)-methanone;

(4-Isopropyl-piperazin-1-yl)-(6-morpholin-4-ylmethyl-pyridin-3-yl)-methanone;

(4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethyl-pyridin-2-yl)-methanone;

2-Piperdin-1-ylmethyl-5-(3-piperdin-1-yl-propoxy)-pyridine;

4-[5-(3-Piperidin-1-yl-propoxy)-pyridin-2-ylmethyl]-morpholine;

2-(4-Piperidin-1-yl-but-1-ynyl)-5-piperidin-1-ylmethyl-pyridine;

(4-Isopropyl-piperazin-1-yl)-[6-(2-piperidin-1-yl-ethylamino)-pyridin-3-yl]-methanone;

(4-Isopropyl-piperazin-1-yl)-[6-(2-morpholin-4-yl-ethylamino)-pyridin-3-yl1-methanone;

{6-[(2-Diethylamino-ethyl)-methyl-amino]-pyridin-3-yl}-(4-isopropyl-piperazin-]-yl)-methanone;

(4-Isopropyl-piperazin-1-yl)-[6-(4-isopropyl-piperazin-1-yl)-pyridin-3-yl]-methanone;

(4-Isopropyl-piperazin-1-yl)-[6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-methanone;

(4-Isopropyl-piperazin-1-yl)-[2-(2-piperidin-1-yl-ethylamino)-pyridin-4-yl]-methanone;

3-(4-Piperidin-1-yl-but-1-ynyl)-5-piperidin-1-ylmethyl-pyridine;

4-[5-(4-Piperidin-1-yl-but-1-ynyl)-pyridin-3-ylmethyl]-morpholine;

2-(4-Piperidin-1-yl-but-1-ynyl)-6-piperidin-1-ylmethyl-pyridine;

4-[6-(4-Piperidin-1-yl-but-1-ynyl)-pyridin-2-ylmethyl]-morpholine;

(2-Methoxy-ethyl)-[6-(4-piperidin-1-yl-but-1-ynyl)-pyridin-2-ylmethyl]-amine;

(4-Isopropyl-piperazin-1-yl)-(6-piperidin-1-ylmethyl-pyridin-3-yl)-methanethione.

3. A compound of claim 2 selected from the group consisting of:

(4-Isopropyl-piperazin-1-yl)-(6-piperidin-1-ylmethyl-pyridin-3-yl)-methanone;

(4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethyl-pyridin-2-yl)-methanone;

2-Piperdin-1-ylmethyl-5-(3-piperdin-1-yl-propoxy)-pyridine;

2-(4-Piperidin-1-yl-but-1-ynyl)-5-piperidin-1-ylmethyl-pyridine;

(4-Isopropyl-piperazin-1-yl)-[6-(2-piperidin-1-yl-ethylamino)-pyridin-3-yl]-methanone;

{6-[(2-Diethylamino-ethyl)-methyl-amino]-pyridin-3-yl}-(4-isopropyl-piperazin-1-yl)-methanone;

(4-Isopropyl-piperazin-1-yl)-[6-(4-isopropyl-piperazin-1-yl)-pyridin-3-yl]-methanone;

(4-Isopropyl-piperazin-1-yl)-[6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-methanone;

(4-Isopropyl-piperazin-1-yl)-[2-(2-piperidin-1-yl-ethylamino)-pyridin-4-yl]-methanone;

3-(4-Piperidin-1-yl-but-1-ynyl)-5-piperidin-1-ylmethyl-pyridine;

2-(4-Piperidin-1-yl-but-1-ynyl)-6-piperidin-1-ylmethyl-pyridine;

(4-Isopropyl-piperazin-1-yl)-(6-piperidin-1-ylmethyl-pyridin-3-yl)-methanethione.

4. A compound of claim 1 wherein said pharmaceutically acceptable salt is an effective amino addition salt.

5. A compound of claim 1 wherein said pharmaceutically acceptable salt is selected from the group consisting of hydrobromide, hydrochloride, sulfate, bisulfate, nitrate, acetate, oxalate, valerate, oleate, palmitate, stearate, laurate, borate, benzoate, lactate, phosphate, tosylate, citrate, maleate, fumarate, succinate, tartrate, naphthylate, mesylate, glucoheptonate, lactiobionate, and laurylsulfonate.

6. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of compound of claim 1 and enantiomers, diastereomers and pharmaceutically acceptable salts and amides thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2005
From: CARRUTHERS, NICHOLAS I.; SHAH, CHANDRAVADAN R.; SWANSON, DEVIN M.
To: JANSSEN PHARMACEUTICAL, N.V.
Reel/Frame 016186/0078 →
Continuity (2)
Provisional Application 6055795900 · Mar 31, 2004
Related Publication 20050222151A1 · Oct 6, 2005