Pyridine compounds as histamine H3 modulators
Certain non-imidazole heterocyclic compounds are Histamine H 3 modulators in the treatment of Histamine H 3 receptor mediated diseases.
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.