US 7,411,091 B2 · N-acyl-N′-benzyl-alkylendiamino derivatives

Abstract

This invention is related to compounds and use of N-Acyl-N′-benzyl-alkylendiamino derivatives of the following general formula (I), wherein A is a straight or branched C2-C8 alkyl chain; X is a methylene, oxygen, sulphur or a NR7 group; R1 is a straight or branched C1-C8 alkyl or C3-C8 alkenylene or C3-C8 alkynylene chain, optionally substituted with CF3, phenyl, phenoxy or naphthyl, the aromatic rings optionally substituted by one or more C1-C4 alkyl, halogens, trifluoromethyl, hydroxy or C1-C4 alkoxy groups; R2, R3 are independently hydrogen, a C1-C3 alkyl chain, halogen, trifluoromethyl, hydroxy or C1-C4 alkoxy groups; R4, R5 are independently hydrogen or C1-C6 alkyl; R6 is a hydrogen or a straight or branched C1-C8 alkyl or linked to R5 can form a five to seven membered lactam; R7 is hydrogen or C1-C6 alkyl; and the pharmaceutically acceptable salts thereof that are active as sodium and/or calcium channel modulators and therefore useful in preventing, alleviating and curing a wide range of pathologies, including, but not limited to, neurological, psychiatric, cardiovascular, inflammatory, ophthalmic, urologic, metabolic and gastrointestinal diseases, where the above mechanisms have been described as playing a pathological role

Claims7

Dependent claims

A compound of general formula I

wherein
A is a straight or branched C2-C8 alkyl chain;
X is a methylene, oxygen, sulphur or a NR7 group;
R1 is a straight or branched C1-C8 alkyl or C3-C8 alkenylene or C3-C8 alkynylene chain, optionally substituted with CF3, phenyl, phenoxy or naphthyl, the aromatic rings optionally substituted by one or more C1-C4 alkyl, halogens, trifluoromethyl, hydroxy or C1-C4 alkoxy groups;
R2, R3 are independently hydrogen, a C1-C3 alkyl chain, halogen, trifluoromethyl, hydroxy or C1-C4 alkoxy groups;
R4, R5 are independently hydrogen or C1-C6 alkyl;
R6 is a hydrogen or a straight or branched C1-C8 alkyl or linked to R5 can form a five to seven membered lactam;
R7 is hydrogen or C1-C6 alkyl;
and the pharmaceutically acceptable salts thereof, with the proviso that when A is —CH2CH2—, R1-X is ortho-benzylthio, R2, R3 and R5 are hydrogen and R6 methyl, R4 is other than hydrogen or methyl;
when A is —CH2CH2—, R1—X 4-methoxy, R2 2-methoxy, R3 and R5 hydrogen and R6 methyl, R4 is other than hydrogen, and
when A is —CH2CH2—, R1—X 3-methoxy, R2 5-methoxy, R3 and R5 hydrogen and R6 methyl, R4 is other than hydrogen.

8 more elements

A compound selected from the group consisting of:

N-2- (4-Butyloxy-benzylamino)-ethyl-acetamide;
N-2-[4-(4-triFluorobutyloxy)-benzylamino]-ethyl-acetamide;
N-2-(4-Pentyloxy-benzylamino)-ethyl-acetamide;
N-2-[4-(5-triFluoropentyloxy)-benzylamino]-ethyl-acetamide;
N-2-(2-Benzyloxy-benzylamino)-ethyl-acetamide;
N-2-(3-Benzyloxy-benzylamino)-ethyl-acetamide;
N-2-(4-Benzyloxy-benzylamino)-ethyl-acetamide;
N-2-[4-(5-Phenyl-pentyloxy)-benzylamino]-ethyl-acetamide;
N-2-[4-(2-Phenethyl)-benzylamino]-ethyl-acetamide;
N-{2-[2-(2-Fluoro-benzyloxy)-benzylamino]-ethyl}-acetamide;
N-{2-[3-(2-Fluoro-benzyloxy)-benzylamino]-ethyl}-acetamide;
N-{2-[4-(2-Fluoro-benzyloxy)-benzylamino]-ethyl}-acetamide;
N-{2-[4-(2-Fluoro-benzyloxy)-2-methoxy-benzylamino]-ethyl }-acetamide;
N-{2-[4-(2-Fluaro-benzyloxy)-2-methyl-benzylamino]-ethyl }-acetamide;
N-{2-[4-(2-Fluoro-benzyloxy)-3-fluoro-benzylamino]-ethyl }-acetamide;
N-{2-[4-(2-Fluoro-benzyloxy)-3-chloro-benzylamino]-ethyl }-acetamide;
N-{2-[4-(2-Fluoro-benzyloxy)-3-methoxy-benzylamino]-ethyl }-acetamide;
N-{2-[4-(2-Fluoro-benzyloxy)-3-methyl-benzylamino]-ethyl }-acetamide;
N-{2-[4-(2-Fluoro-benzyloxy)-3,5-dimethoxy-benzylamino]-ethyl }-acetamide;
N-{2-[4-(2-Fluoro-benzyloxy)-3, 5-dimethyl-benzylamino]-ethyl }-acetamide;
N-{2-[4-(2-Fluoro-benzyloxy)-3-bromo-5-methoxy-benzylamino]-ethyl }-acetamide;
N-3-(4-Pentyloxy-benzylamino)-propyl-acetamide;
N-2-[4-(5-trifluoropentyloxy)-benzylamino]-propyl acetamide;
N-3-(4-Benzyloxy-benzylamino)-propyl-acetamide;
N-3-[4-(2-Phenethyl)-benzylamino]-propyl-acetamide;
N-3-[4-(5-Phenyl-pentyloxy)-benzylamino]-propyl-acetamide;
N-{3-[4-(2-Fluoro-benzyloxy)-2-methoxy-benzylamino]-propyl }-acetamide;
N-{3-[4-(2-Fluoro-benzyloxy)-2-methyl-benzylamino]-propyl}-acetamide;
N-{3-[4-(2-Fluoro-benzyloxy)-3-fluoro-benzylamino]-propyl }-acetamide;
N-{3-[4-(2-Fluoro-benzyloxy)-3-chloro-benzylamino]-propyl }-acetamide;
N-{3-[4-(2-Fluoro-benzyloxy)-3-methoxy-benzylamino]-propyl}-acetamide;
N-{3-[4-(2-Fluoro-benzyloxy)-3-methyl-benzylamino]-propyl }-acetamide;
N-{3-[4-(2-Fluoro-benzyloxy)-3,5-dimethoxy-benzylamino]-propyl}-acetamide;
N-{3-[4-(2-Fluoro-benzyloxy)-3,5-dimethyl-benzylamino]-propyl}-acetamide;
N-{3-[4-(2-Fluoro-benzyloxy)-3-bromo-5-methoxy-benzylamino]-propyl}-acetamide;
1-[2-(4-Butyloxy-benzylamino)-ethyl]-pyrrolidin-2-one;
l-{2-[4-(4-triFluorobutyloxy-benzylamino]-ethyl}-pyrrolidin-2-one;
1-[2-(4-Pentyloxy-benzylamino)-ethyl]-pyrrolidin-2-one;
l-{2-[4-(5-triFluoropentyloxy-benzylamino]-ethyl}-pyrrolidin-2-one;
1-[2-(2-Benzyloxy-benzylamino)-ethyl]-pyrrolidin-2-one;
1-[2-(3-Benzyloxy-benzylamino)-ethyl]-pyrrolidin-2-one;
1-[2-(4-Benzyloxy-benzylamino)-ethyl]-pyrrolidin-2-one;
1-[2-(4-Benzylthio-benzylamino)-ethyl]-pyrrolidin-2-one;
1-[2-(4-Benzylamino-benzylamino)-ethyl]-pyrrolidin-2-one;
l-{2-[4-(5-Phenyl-pentyloxy)-benzylamino]-ethyl}-pyrrolidin-2-one;
1- {2-[4-(2-Phenoxy-ethoxy)-benzylamino]-ethyl}-pyrrolidin-2-one;
1- {2-[4-(Naphthalen-1-ylmethoxy)-benzylamino]-ethyl}-pyrrolidin-2-one;
l-{2-[2-(3-Fluorobenzyloxy)-benzylamino]-ethyl}-pyrrolidin-2-one;
l-{2-[3-(3-Fluorobenzyloxy)-benzylamino]-ethyl}-pyrrolidin-2-one;
l-{2-[4-(3-Fluorobenzyloxy)-benzylamino]-ethyl}-pyrrolidin-2-one;
1-{2-[4-(4-tert-Butyl-benzyloxy)-benzylamino]-ethyl}-pyrrolidin-2-one;
1-{2-[4-(4-triFluoromethyl-benzyloxy)-benzylamino]-ethyl}-pyrrolidin-2-one;
1-{2-[4-(2,6-Dichloro-benzyloxy)-benzylamino]-ethyl}-pyrrolidin-2-one;
1-{2-[4-(3,5-Dimethoxy-benzyloxy)-benzylamino]-ethyl}-pyrrolidin-2-one;
1-{2-[4-(2-Fluoro-benzyloxy)-2-methoxy-benzylamino]-ethyl}-pyrrolidin-2-one;
1-{2-[4-(2-Fluoro-benzyloxy)-2-methyl -benzylamino]-ethyl}-pyrrolidin-2-one;
1-{2-[4- C2-Fluoro-benzyloxy)-3-fluoro-benzylamino]-ethyl}-pyrrolidin-2-one;
1-{2-[4-(2-Fluoro-benzyloxy)-3-methoxy-benzylamino]-ethyl}-pyrrolidin-2-one;
1-{2-[4-(2-Fluoro-benzyloxy)-3-methyl-benzylamino]-ethyl}-pyrrolidin-2-one;
1-{2-[4-(2-Fluoro-benzyloxy)-3-chloro-benzylamino]-ethyl}-pyrrolidin-2-one;
1-{2-[4-(2-Fluoro-benzyloxy)-3,5-dimethoxy-benzylamino]-ethyl}-pyrrolidin-2-one;
1-{2-[4-(2-Fluoro-benzyloxy)-3,5-dimethyl-benzylamino]-ethyl}-pyrrolidin-2-one;
1-{2-[4-(2-fluoro-benzyloxy)-3-bromo-5-methoxy-benzylamino]-ethyl}-pyrrolidin-2-one;
1-[3-(4-Pentyloxy-benzylamino)-propyl]-pyrrolidin-2-one;
1-[3-(2-Benzyloxy-benzylamino)-propyl]-pyrrolidin-2-one;
1-[3-(3-Benzyloxy-benzylamino)-propyl]-pyrrolidin-2-one;
1-[3-(4-Benzyloxy-benzylamino)-propyl]-pyrrolidin-2-one;
1-{3-[4-(5-Phenyl-pentyloxy)-benzylamino]-propyl}-pyrrolidin-2-one;
1- {3-[4-(2-Phenoxy-ethoxy)-benzylamino]-propyl}-pyrrolidin-2-one;
1-{3-[4-(Naphthalen-1-ylmethoxy)-benzylamino]-propyl)-pyrrolidin-2-one;
1-{3-[4-(4-tert-Butyl-benzyloxy)-benzylamino]-propyl)-pyrrolidin-2-one;
1- {3-[4-(4-triFluoromethyl-benzyloxy)-benzylamino]-propyl }-pyrrolidin-2-one;
1-(3-[4-(2,6-Dichloro-benzyloxy)-benzylamino]-propyl}-pyrrolidin-2-one;
1-{3-[4-(3, 5-Dimethoxy-benzyloxy)-benzylamino}-propyl}-pyrrolidin-2-one;
1-{3-[4-(2-Fluoro-benzyloxy)-2-methoxy-benzylamino]-propyl}-pyrrolidin-2-one;
1-{3-[4-(2-Fluoro-benzyloxy)-2-methyl-benzylamino]-propyl}-pyrrolidin-2-one;
1-{3-[4-(2-Fluoro-benzyloxy)-3-fluoro-benzylamino]-propyl}-pyrrolidin-2-one;
1-{3-[4-(2-Fluoro-benzyloxy)-3-methoxy-benzylamino]-propyl }-pyrrolidin-2-one;
1-{3-[4-(2-Fluoro-benzyloxy)-3-methyl-benzylamino]-propyl }-pyrrolidin-2-one;
1-{3-[4-(2-Fluoro-benzyloxy)-3-chloro-benzylamino]-propyl }-pyrrolidin-2-one;
1-{3-[4-(2-Fluoro-benzyloxy)-3,5-dimethoxy-benzylamino]-propyl}-pyrrolidin-2-one;
1-{3-[4-(2-Fluoro-benzyloxy)-3,5-dimethyl-benzylamino]-propyl}-pyrrolidin-2-one;
1-{3-[4-(2-f Fluoro-benzyloxy)-3-bromo-5-methoxy-benzylamino]-propyl}-pyrrolidin-2-one;
or pharmaceutically acceptable salts thereof.

81 more elements

Dependencies are inferred from the claim text.

N-acyl-N′-benzyl-alkylendiamino derivatives

Life of this patent

N-acyl-N′-benzyl-alkylendiamino derivatives

Life of this patent

Abstract

Claims7