Back to results
US 6,723,742 B2Granted
Substituted 3,5-diphenyl-1,2,4-triazoles and their use as pharmaceutical metal chelators
AssigneeNovartis AG
InventorsRené Lattmann, Pierre Acklin
Life of this patent
Estimating the term…
Abstract
The use is described of 3,5-diphenyl-1,2,4-triazoles of the formula I in which R1-R5 are as defined in the description. The compounds have useful pharmaceutical properties and are particularly active as iron chelators. They can be used for the treatment of iron overload in warm-blooded animals.
Claims6
A compound of formula (II)
- wherein each of R1 and R5, independently, is hydrogen;
- halogen;
- lower alkyl;
- halo-lower alkyl;
- lower alkoxy;
- halo-lower alkoxy;
- carboxyl;
- carbamoyl;
- N-lower alkylcarbamoyl;
- N,N-di- lower alkylcarbamoyl;
- or nitrile;
- each of R2 and R4, independently, is hydrogen;
- unsubstituted lower alkanoyl;
- lower alkanoyl substituted by halogen, hydroxyl, lower alkoxy, trifluoromethyl, cyclo-lower alkyl or phenyl;
- unsubstituted aroyl;
- or aroyl substituted by one or two substituents selected from lower alkyl, lower alkoxy, hydroxyl, nitro, halogen, trifluoromethyl, carboxyl, lower alkoxycarbonyl, amino, N-lower alkylamino, N,N-di-lower alkylamino, aminocarbonyl, lower alkylaminocarbonyl, di-lower alkylaminocarbonyl and nitrile;
- R3 is R6R7N—C(O)-lower alkyl;
- aryl substituted by heterocycloalkyl, heteroaryl or heterocycloalkylcarbonyl:
- aryl-lower alkyl substituted by pyrrolidino;
- unsubstituted heteroaryl;
- heteroaryl substituted by one or two substituents selected from lower alkyl, halogen, trifluoromethyl, carboxyl and lower alkoxycarbonyl;
- unsubstituted heteroaralkyl;
- or heteroaralkyl substituted by one or two substituents selected from lower alkyl, halogen, trifluoromethyl, carboxyl and lower alkoxycarbonyl;
- and
- R6 and R7, together with the nitrogen atom to which they are bonded, form an unsubstituted azaalicyclic ring;
- or an azaalicyclic ring substituted by halogen or lower alkyl;
- or a salt thereof.
24 more elements
A compound selected from the group consisting of:
- {4-[3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-ly]phenyl}-(4-methylpiperazin-1-yl)methanone;
- {4-[3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-ly]phenyl}-morpholin-4-yl)methanone;
- 2-[3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]-1-(4-methylpiperazin-1-yl)ethanone;
- 2-[3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]-1-morpholin-4-yl-ethanone;
- 2-[3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]-N-(2-morpholin-4-yl-ethyl)acetamide;
- 2-(3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]-N-[2-(4-methylpiperazin- 1-yl)ethyl]acetamide;
- 2-[3,5-bis(5-chloro-2-hydroxyphenyl )-[1,2,4]triazol-1-yl]-N-(2-morpholin-4-yl-ethyl)acetamide;
- 3,5-bis(2-hydroxyphenyl)-1-(4-pyrrolidin-1-ylbenzyl)-1H-[1,2,4]triazole;
- 3,5-bis(2-hydroxyphenyl)-1-(pyridin-3-ylmethyl)-1H-[1,2,4]triazole;
- 3,5-bis(2-hydroxyphenyl)-1-(pyridin-4-ylmethyl)-1H-[1,2,4]triazole;
- and
- 3,5-bis(5-chloro-2-hydroxyphenyl)-1-(pyridin-2-ylmethyl)-1H-[1,2,4]triazole;
- or a pharmaceutically acceptable salt thereof.
10 more elements
Dependencies are inferred from the claim text.