Heteroaryloxy nitrogenous saturated heterocyclic derivative
AssigneeMsd K.K.
InventorsNorikazu Ohtake, Akira Naya, Yuji Haga, Makoto Jitsuoka, Takuya Suga, Ryo Yoshimoto, Shigeru Tokita, Akio Kanatani
Life of this patent
Estimating the term…
Abstract
Provided are compounds of a formula (I) and their pharmaceutically-acceptable salts: wherein X1, X2 and X3 each independently represent N or CH; W represents the following formula (II): or the following formula (III): Y represents a group of a formula (IV): The compounds have a histamine-H3 receptor antagonistic or inverse-agonistic activity and are useful for remedy and/or prevention of obesity, diabetes, hormone secretion disorders, sleep disorders, etc.
Claims8
A compound of the formula (I):
- wherein:
- R is selected from the group consisting of:
- a linear or branched C2-6 alkyl group, or a cycloalkyl group having from 3 to 9 carbon atoms, which is unsubstituted or substituted with a group selected from the group consisting of:
- a cyano group;
- a hydroxyl group;
- a lower alkyl group optionally substituted with a hydroxyl group, a halogen atom or an amino group;
- a lower alkoxy group optionally substituted with a halogen atom;
- a halogen atom;
- a mono-lower alkylaminocarbonyloxy group;
- a di-lower alkylaminocarbonyloxy group;
- a mono-lower alkylcarbamoyl group;
- a di-lower alkylcarbamoyl group;
- a carbamoyl group;
- a cycloalkyliminocarbonyl group;
- and a trifluoromethyl group,
- Y is selected from the group consisting of:
- (1) a phenyl group;
- which is unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of:
- a hydroxyl group;
- a lower alkyl group optionally substituted with a hydroxy group, a halogen atom or an amino group;
- a lower alkoxy group optionally substituted with a halogen atom;
- a lower alkylsulfonyl group;
- a cyclo-lower alkylsulfonyl group;
- a halogen atom;
- a mono-lower alkylaminocarbonyloxy group;
- a di-lower alkylaminocarbonyloxy group;
- a mono-lower alkylcarbamoyl group;
- a di-lower alkylcarbamoyl group;
- a cycloalkyliminocarbamoyl group;
- a lactam ring;
- a mono-lower alkylamino group;
- a di-lower alkylamino group;
- an alkanoyl group;
- an alkoxycarbonylamino group wherein the nitrogen atom optionally substituted with a lower alkyl group;
- an alkanoylamino group wherein the nitrogen atom is optionally substituted with a lower alkyl group;
- and an alkylsulfonylamino group wherein the nitrogen atom is optionally substituted with a lower alkyl group;
- or
- (2) a group of the formula (Q1-1):
- wherein R7 represents a hydrogen atom, a lower alkyl group, a cyclo-lower alkyl group, a halo-lower alkyl group, or an aralkyl group;
- or a pharmaceutically acceptable salt thereof.
A compound which is selected from the group consisting of:
- 2-(1-cyclopentylpiperidin-4-yloxy)-5-(4-cyanophenyl)pyridine,
- 2-(1-cyclopentylpiperidin-4-yloxy)-5-(1-methyl-1H-pyridin-2-on-5-yl)pyridine,
- 2-(1-cyclopentylpiperidin-4-yloxy)-5-(1-difluoromethyl-1H-pyridin-2-on-5-yl)pyridine,
- 2-(1-cyclobutylpiperidin-4-yloxy)-5-(1-methyl-1H-pyridin-2-on-5-yl)pyridine,
- 2-(1-isopropylpiperidin-4-yloxy)-5-(1-methyl-1H-pyridin-2-on-5-yl)pyridine,
- 2-(1-cyclobutylpiperidin-4-yloxy)-5-{1-(2-fluoroethyl)-1H-pyridin-2-on-5-yl}pyridine,
- 2-(1-cyclobutylpiperidin-4-yloxy)-5-{1-(2-fluoroethoxy-1H-pyridin-2-on-5-yl}pyridine,
- 2-(1-cyclobutylpiperidin-4-yloxy)-5-{1-(2-fluoroethyl)-1H-pyridin-2-on-4-yl}pyridine,
- 2-(1-cyclobutylpiperidin-4-yloxy)-5-(3-chloro-1-methyl-1H-pyridin-2-on-5-yl)pyridine,
- 2-(1-cyclobutylpiperidin-4-yloxy)-5-(1-ethyl-1H-pyridin-2-on-5-yl)pyridine, and
- 2-(1-isopropylpiperidin-4-yloxy)-5-(1-ethyl-1H-pyridin-2-on-5-yl)pyridine,
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.