Catechol derivatives or salt thereof, processes for preparing the same, and pharmaceutical compositions comprising the same
AssigneeHexapharmatec Co., Ltd.
InventorsShin Han, Jae-Hyoung Lee
Life of this patent
Estimating the term…
Abstract
Provided is a novel catechol derivative or pharmaceutically acceptable salt thereof having an alkyl moiety substituted with alkylamino and/or a N-alkyl-substituted thiophene-(thio)carboxamide moiety, a process for the preparation thereof, and a pharmaceutical composition including the same.
Claims11
A compound of Formula 1 or pharmaceutically acceptable salt thereof:
- wherein,
- Y is O or S,
- (1) when Y is O,
- R1 is hydrogen;
- or a C1˜C4 alkyl group substituted with a mono- or di-C1˜C5 alkylamino,
- R2 is a C1˜C6 alkyl group,
- R3 is hydrogen, and
- R4 is a (4-(dimethylamino)tetrahydro-2H-pyran-4-yl)methyl group;
- a C1˜C4 alkyl group substituted with a mono- or di-C1˜C5 alkylamino;
- a C1˜C4 alkyl group substituted with a nitrogen-containing cyclic ring (wherein the nitrogen-containing cyclic ring is morpholine, piperidine, or pyrrolidine which is optionally substituted with C1˜C4 alkyl);
- or a piperidinyl group optionally substituted with C1˜C4 alkyl,
- (2) when Y is S,
- R1 and R2 are, independently of each other, hydrogen;
- a C1˜C6 alkyl group;
- or a C1˜C4 alkyl group substituted with a mono- or di-C1˜C5 alkylamino,
- R3 is hydrogen, and
- R4 is a C1˜C4 alkyl group substituted with a mono- or di-C1˜C5 alkylamino.
A The compound or pharmaceutically acceptable salt thereof, which is one or more selected from the group consisting of:
- N-(2-(diisopropylamino)ethyl)-5-(4-hydroxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-(2-(diisopropylamino)ethyl)-5-(4-(2-diethylamino)ethoxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-(2-(diisopropylamino)ethyl)-5-(4-hydroxy-3-methoxyphenyl)thiophene-2-thiocarboxamide hydrochloride;
- N-(2-(diisopropylamino)ethyl)-5-(4-(2-diethylamino)ethoxy-3-methoxyphenyl)thiophene-2-thiocarboxamide hydrochloride;
- N-isopropyl-5-(4-(2-diethylamino)ethoxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-isopropyl-5-(4-(2-diethylamino)ethoxy-3-methoxyphenyl)thiophene-2-thiocarboxamide hydrochloride;
- N-(2-(diethylamino)ethyl)-5-(4-hydroxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-(2-(diethylamino)ethyl)-5-(4-(2-diethylamino)ethoxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-(2-(dimethylamino)ethyl)-5-(4-hydroxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-(2-(dimethylamino)ethyl)-5-(4-(2-diethylamino)ethoxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-(2-(4-morpholino)ethyl)-5-(4-hydroxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-(2-(1-piperidino)ethyl)-5-(4-hydroxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-(2-(1-piperidino)ethyl)-5-(4-(2-diethylamino)ethoxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-(2-(1-pyrrolidino)ethyl)-5-(4-hydroxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-((4-(dimethylamino)tetrahydro-2H-pyran-4-yl)methyl)-5-(4-hydroxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-((4-(dimethylamino)tetrahydro-2H-pyran-4-yl)methyl)-5-(4-(2-diethylamino)ethoxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-(4-(1-methyl)piperidinyl)-5-(4-hydroxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-(2-(2-(1-methyl)pyrrolidino)ethyl)-5-(4-hydroxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N-(2-(2-(1-methyl)pyrrolidino)ethyl)-5-(4-(2-diethylamino)ethoxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- N—((S)-2-(1-ethyl)pyrrolidinomethyl)-5-(4-hydroxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride;
- and
- N—((S)-2-(1-ethyl)pyrrolidinomethyl)-5-(4-(2-diethylamino)ethoxy-3-methoxyphenyl)thiophene-2-carboxamide hydrochloride.
N-((4-(dimethylamino)tetrahydro-2H-pyran-4-yl)methyl)-5-(4-hydroxy-3-methoxyphenyl)thiophene-2-carboxamide or pharmaceutically acceptable salt thereof.
N-((4-(dimethylamino)tetrahydro-2H-pyran-4-yl)methyl)-5-(4-(2-diethylamino)ethoxy-3-methoxyphenyl)thiophene-2-carboxamide or pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.