Aminoquinoxaline derivatives for treatment of neurodegenerative diseases
View Patent ↗The present invention relates to compounds of formula (I) below: for which: —X represents a hydrogen atom, a halogen atom, a group NO 2 or NH 2 , —R 0 represents H or —CH 2 —C≡CH, and —R 1 and R 2 each represent, independently of one another, a hydrogen atom; a saturated or unsaturated, linear or branched hydrocarbon-based chain comprising from 1 to 10 carbon atoms; or an optionally substituted aryl group, and also the pharmaceutically acceptable salts thereof, the stereoisomers thereof or mixtures of stereoisomers thereof in any proportion, in particular for use thereof as a medicament, in particular in the treatment or prevention of neurodegenerative diseases, and also the processes for the preparation thereof and the pharmaceutical compositions comprising same.
1. A method for the treatment of Parkinson's disease comprising the administration to a patient in need thereof of an effective quantity of a compound of formula (I) below:
or a pharmaceutically acceptable salt thereof, a stereoisomer thereof or a mixture of stereoisomers thereof in any proportions,
wherein:
X represents a hydrogen atom, a halogen atom, an NO 2 group or an NH 2 group,
R 0 represents H or —CH 2 —C≡H, and
R 1 and R 2 each represent, independently of one another, a hydrogen atom; a saturated or unsaturated, linear or branched hydrocarbon chain comprising 1 to 10 carbon atoms; or an optionally substituted aryl group.
2. The method according to claim 1 , wherein the mixture of stereoisomers is a mixture of enantiomers.
3. The method according to claim 2 , wherein the mixture of enantiomers is a racemic mixture.
4. The method according to claim 1 , wherein X represents a hydrogen atom, a bromine atom, an NH 2 group or an NO 2 group.
5. The method according to claim 1 , wherein X represents a hydrogen atom.
6. The method according to claim 1 , wherein R 0 represents H.
7. The method according to claim 1 , wherein R 1 and R 2 each represent, independently of one another, a hydrogen atom; a saturated or unsaturated, linear or branched hydrocarbon chain comprising 1 to 10 carbon atoms; or an aryl group optionally substituted by one or more groups selected from the group consisting of a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, aryl, N 3 , NO 2 , NH 2 and —NH—((C 1 -C 6 )alkyl).
8. The method according to claim 1 , wherein R 1 and R 2 each represent, independently of one another, a hydrogen atom; a saturated or unsaturated, linear or branched hydrocarbon chain comprising 1 to 10 carbon atoms; or an aryl group optionally substituted by one or more groups selected from the group consisting of a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, aryl, NH 2 and —NH—((C 1 -C 6 )alkyl).
9. The method according to claim 1 , wherein R 1 and R 2 each represent, independently of one another, a hydrogen atom; a saturated or unsaturated, linear or branched hydrocarbon chain comprising 1 to 10 carbon atoms; or an aryl group optionally substituted by one or more groups selected from the group consisting of a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy and aryl.
10. The method according to claim 1 , wherein R 1 and R 2 each represent, independently of one another, a hydrogen atom, a (C 1 -C 6 )alkyl group, or an optionally substituted aryl group.
11. The method according to claim 1 , wherein R 1 and R 2 each represent, independently of one another, a hydrogen atom, a (C 1 -C 6 )alkyl group, or an optionally substituted phenyl group.
12. The method according to claim 1 , wherein R 1 represents an aryl group optionally substituted by one or more groups selected from the group consisting of a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, aryl, N 3 , NO 2 , NH 2 and —NH—((C 1 -C 6 )alkyl).
13. The method according to claim 1 , wherein R 1 represents a phenyl group optionally substituted by one or more groups selected from the group consisting of a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, aryl, N 3 , NO 2 , NH 2 and —NH—((C 1 -C 6 )alkyl).
14. The method according to claim 1 , wherein R 1 represents a phenyl group optionally substituted by one or more groups selected from the group consisting of a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, aryl, NH 2 and —NH—((C 1 -C 6 )alkyl).
15. The method according to claim 1 , wherein R 1 represents a phenyl group optionally substituted by one or more groups selected from the group consisting of a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy and aryl.
16. The method according to claim 1 , wherein the compound of formula (I) is selected from the group consisting of the following compounds:
17. A method for the treatment of Parkinson's disease comprising the administration to a patient in need thereof of an effective quantity of a compound of formula (I) below:
or a pharmaceutically acceptable salt thereof, a stereoisomer thereof or a mixture of stereoisomers thereof in any proportions,
wherein:
X represents a hydrogen atom, a halogen atom, an NO 2 group or an NH 2 group,
R 0 represents H or —CH 2 —C≡H, and
R 1 and R 2 each represent, independently of one another, a hydrogen atom; a (C 1 -C 6 )alkyl group; or an aryl group optionally substituted by one or more groups selected from the group consisting of a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, aryl, N 3 , NO 2 , NH 2 and —NH—((C 1 -C 6 )alkyl).
18. The method according to claim 17 , wherein R 1 and R 2 each represent, independently of one another, a hydrogen atom; a (C 1 -C 6 )alkyl group; or an aryl group optionally substituted by one or more groups selected from the group consisting of a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, aryl, NH 2 and —NH—((C 1 -C 6 )alkyl).
19. The method according to claim 17 , wherein R 1 and R 2 each represent, independently of one another, a hydrogen atom; a (C 1 -C 6 )alkyl group; or an aryl group optionally substituted by one or more groups selected from the group consisting of a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy and aryl.
20. A method for the treatment of Parkinson's disease comprising the administration to a patient in need thereof of an effective quantity of a compound of formula (I) below:
or a pharmaceutically acceptable salt thereof, a stereoisomer thereof or a mixture of stereoisomers thereof in any proportions,
wherein:
X represents a hydrogen atom, a halogen atom, an NO 2 group or an NH 2 group,
R 0 represents H or —CH 2 —C≡H, and
R 1 and R 2 each represent, independently of one another, a hydrogen atom; a (C 1 -C 6 )alkyl group; or a phenyl group optionally substituted by one or more groups selected from the group consisting of a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, aryl, N 3 , NO 2 , NH 2 and —NH—((C 1 -C 6 )alkyl).
21. The method according to claim 20 , wherein R 1 and R 2 each represent, independently of one another, a hydrogen atom; a (C 1 -C 6 )alkyl group; or a phenyl optionally substituted by one or more groups selected from the group consisting of a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, aryl, NH 2 and —NH—((C 1 -C 6 )alkyl).
22. The method according to claim 20 , wherein R 1 and R 2 each represent, independently of one another, a hydrogen atom; a (C 1 -C 6 )alkyl group; or a phenyl group optionally substituted by one or more groups selected from the group consisting of a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy and aryl.