Benzothiazoles having histamine H3 receptor activity
AssigneeHigh Point Pharmaceuticals, LLC
InventorsFlorencio Zaragoza Dorwald, Rolf Hohlweg, Inge Thoger Christensen, Jane Marie Lundbeck, Knud Erik Andersen
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Abstract
Certain novel benzothiazoles and benzoxazoles, e.g., 2-(piperazin-1-yl)benzothiazoles and 2-(piperazin-1-yl)benzoxazoles, optionally substituted in the 3 and/or 4 positions of the piperazine rings, having histamine H3 antagonistic activity can be used in pharmaceutical compositions.
Claims12
A method of treating obesity comprising administering to a human subject a compound selected from the group consisting of:
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-6-yl]piperidin-1-ylmethanone,
- 2-(4-isopropylpiperazin-1-yl)benzothiazole-6-carboxylic acid dimethylamide,
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-6-yl]morpholin-4-ylmethanone,
- 2-(4-isopropylpiperazin-1-yl)-6-piperidin-1-ylmethylbenzothiazole,
- 2-(4-isopropylpiperazin-1-yl)-6-(morpholin-4-ylmethyl)benzothiazole,
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]dimethylamine,
- [2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]dimethylamine,
- 2-(4-cyclopropylpiperazin-1-yl)-6-(pyrrolidin-1-ylmethyl)benzothiazole,
- 2-(4-cyclopropylpiperazin-1-yl)-6-(morpholin-4-ylmethyl)benzothiazole,
- 2-(4-cyclopropylpiperazin-1-yl)-6-(piperidin-1-ylmethyl)benzothiazole,
- cyclopropyl-[2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]amine,
- 2-(4-isopropylpiperazin-1-yl)-5-(pyrrolidin-1-ylmethyl)benzothiazole,
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-5-ylmethyl]dimethylamine, and
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-5-yl]pyrrolidin-1-ylmethanone;
- or a pharmaceutically acceptable salt thereof.
A method of reducing weight comprising administering to a human subject a compound selected from the group consisting of
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-6-yl]piperidin-1-ylmethanone,
- 2-(4-isopropylpiperazin-1-yl)benzothiazole-6-carboxylic acid dimethylamide,
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-6-yl]morpholin-4-ylmethanone,
- 2-(4-isopropylpiperazin-1-yl)-6-piperidin-1-ylmethylbenzothiazole,
- 2-(4-isopropylpiperazin-1-yl)-6-(morpholin-4-ylmethyl)benzothiazole,
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]dimethylamine,
- [2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]dimethylamine,
- 2-(4-cyclopropylpiperazin-1-yl)-6-(pyrrolidin-1-ylmethyl)benzothiazole,
- 2-(4-cyclopropylpiperazin-1-yl)-6-(morpholin-4-ylmethyl)benzothiazole,
- 2-(4-cyclopropylpiperazin-1-yl)-6-(piperidin-1-ylmethyl)benzothiazole,
- cyclopropyl-[2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]amine,
- 2-(4-isopropylpiperazin-1-yl)-5-(pyrrolidin-1-ylmethyl)benzothiazole,
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-5-ylmethyl]dimethylamine, and
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-5-yl]pyrrolidin-1-ylmethanone;
- or a pharmaceutically acceptable salt thereof.
A method of suppressing appetite or inducing satiety comprising administering to a human subject a compound selected from the group consisting of:
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-6-yl]piperidin-1-ylmethanone,
- 2-(4-isopropylpiperazin-1-yl)benzothiazole-6-carboxylic acid dimethylamide,
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-6-yl]morpholin-4-ylmethanone,
- 2-(4-isopropylpiperazin-1-yl)-6-piperidin-1-ylmethylbenzothiazole,
- 2-(4-isopropylpiperazin-1-yl)-6-(morpholin-4-ylmethyl)benzothiazole,
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]dimethylamine,
- [2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]dimethylamine,
- 2-(4-cyclopropylpiperazin-1-yl)-6-(pyrrolidin-1-ylmethyl)benzothiazole,
- 2-(4-cyclopropylpiperazin-1-yl)-6-(morpholin-4-ylmethyl)benzothiazole,
- 2-(4-cyclopropylpiperazin-1-yl)-6-(piperidin-1-ylmethyl)benzothiazole,
- cyclopropyl-[2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]amine,
- 2-(4-isopropylpiperazin-1-yl)-5-(pyrrolidin-1-ylmethyl)benzothiazole,
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-5-ylmethyl]dimethylamine, and
- [2-(4-isopropylpiperazin-1-yl)benzothiazol-5-yl]pyrrolidin-1-ylmethanone;
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.