Patent CA-2359454-C (CA)
Title: ((aminoiminomethyl) amino) alkanecarboxamides and their applications in therapy
Inventor: MOINET GERARD
IPC: A61P3/10
Filed: 1999-12-30
Granted: 2009-10-27
Abstract: The invention relates to pharmaceutical composition comprising as active principle a compound of general formula (I) (see formula I) in which:     R1 is selected from one of the following groups:  - H; and -(C1-C20)alkyl substituted or unsubstituted by one or more of the following groups:   amino, hydroxyl, (C1-C5)alkyl, (C1-C5)alkoxy, (C1-C5)alkylthio, (C1-C5)alkylamino, trifluoromethyl;  R2 is selected from -(C3-C8)cycloalkyl substituted or unsubstituted by one or more of the following groups:   amino, hydroxyl, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5)alkylthio, (C1-C5)alkylamino, trifluoromethyl;  -(C6-C14)aryl substituted or unsubstituted by one or more of the following groups:   amino, hydroxyl, halogen, (C1-C5)alkyl, (C1-C5)alkoxy, (C1-C5)alkylthio, (C1-C5)alkylamino, trifluoromethyl, cyano; and heteroaryl selected from pyridyl, pyrimidinyl, furyl, pyrrolyl, thienyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, indolyl, benzofuryl and imidazolyl, optionally substituted by one or more of the following groups:   amino, hydroxyl, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, trifluoromethyl, cyano;   a nitrogen atom can additionally be substituted by a(C6-C14) aryl, (C6-C14) acyl or (C1-C5) alkyl group;     R3 is selected from - H;   - (C3-C8)cycloalkyl substituted or unsubstituted by one or more of the following groups:   amino, hydroxyl, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, trifluoromethyl;   - (C3-C8)heterocycloalkyl containing one or more heteroatoms selected from N, O and S and substituted or unsubstituted by one or more of the following groups:   amino, hydroxyl, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, trifluoromethyl;   a nitrogen atom can additionally be substituted by a (C6-C14)aryl, (C6-C14) acyl or (C1-C5) alkyl group;   -(C6-C14) aryl substituted or unsubstituted by one or more of the following groups:   amino, hydroxyl, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, trifluoromethyl, cyano;     -(C1-C13) heteroaryl containing one or more heteroatoms selected from N, O and S and substituted or unsubstituted by one or more of the following groups:   amino, hydroxyl, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, trifluoromethyl, cyano;   a nitrogen atom can additionally be substituted by a(C6-C14) aryl, (C6-C14) acyl or (C1-C5) alkyl group; and - (C6-C14) aryl- (C1-C5) alkyl substituted or unsubstituted by one or more of the following groups:  amino, hydroxyl, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, trifluoromethyl, cyano;   and A is selected from the groups:  -CH2-, -CH2-CH2-, and -CHR4-, R4 being selected from:   -(C1-C20)alkyl substituted or unsubstituted by one or more of the following groups:   amino, hydroxyl, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, trifluoromethyl;   - (C3-C8)cycloalkyl substituted or unsubstituted by one or more of the following groups:   amino, hydroxyl, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, trifluoromethyl; and -(C3-C8)heterocycloalkyl containing one or more heteroatoms selected from N, O and S and substituted or unsubstituted by one or more of the following groups:   amino, hydroxyl, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, trifluoromethyl;   a nitrogen atom can additionally be substituted by a(C6-C14) aryl, (C6-C14) acyl or (C1-C5) alkyl group;   or a pharmaceutically acceptable salt or solvate thereof, and a pharmaceutically acceptable excipient or vehicle.     These compositions can be used in the treatment of pathologies associated with insulin resistance.