Dihydro-oxazolobenzodiazepinone compounds, a process for there preparation and pharmaceutical compositions containing them
View Patent ↗Compounds of formula (I): wherein: R 1 represents a hydrogen atom or an alkyl group; R 2 represents an alkyl group; R 3 represents an aryl or heteroaryl group. Medicinal products containing the same which are useful in the treatment or prevention of psychiatric and neurological disorders characterized by cognitive deficits.
1. A compound selected from those of formula (I):
wherein:
R 1 represents a hydrogen atom or a linear or branched (C 1 -C 4 )alkyl group;
R 2 represents a linear or branched (C 1 -C 4 )alkyl group;
R 3 represents an aryl or heteroaryl group;
and positional isomers, enantiomers, diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid, and complexes and adducts thereof.
2. The compound of claim 1 , wherein R 1 represents a hydrogen atom.
3. The compound of claim 1 , wherein R 2 represents a methyl group.
4. The compound of claim 1 , wherein R 3 represents a heteroaryl group.
5. The compound of claim 1 , wherein R 3 represents a bicyclic aromatic group having from 1 to 3 identical or different hetero atoms selected from nitrogen, oxygen and sulphur, optionally substituted by one or more identical or different groups selected from a halogen atom; a linear or branched (C 1 -C 6 )alkyl group which is unsubstituted or substituted by one or more halogen atoms; a linear or branched (C 1 -C 6 )alkoxy group; a linear or branched (C 1 -C 6 )alkylcarbonyl group; a carboxy group; a linear or branched (C 1 -C 6 )alkoxycarbonyl group; a hydroxy group; a cyano group; a nitro group; an aminocarbonyl group which is unsubstituted or substituted by one or more linear or branched (C 1 -C 6 )alkyl groups; and an amino group which is unsubstituted or substituted by one or two linear or branched (C 1 -C 6 )alkyl groups.
6. The compound of claim 1 , wherein R 3 represents a benzothienyl or quinolyl group, optionally substituted by one or more identical or different groups selected from a halogen atom and a linear or branched (C 1 -C 4 )alkyl group which is unsubstituted or substituted by one or more halogen atoms.
7. The compound of claim 1 , wherein R 3 represents a 1-benzothienyl group, optionally substituted by one or more identical or different groups selected from a halogen atom and a linear or branched (C 1 -C 4 )alkyl group which is unsubstituted or substituted by one or more halogen atoms.
8. The compound of claim 1 , wherein R 3 represents a 1-benzothien-2-yl group, optionally substituted by one or more identical or different groups selected from a halogen atom and a linear or branched (C 1 -C 4 )alkyl group which is unsubstituted or substituted by one or more halogen atoms.
9. The compound of claim 1 , wherein R 3 represents a 1-benzothien-2-yl group, optionally substituted by one or more identical or different groups selected from a fluorine atom, a chlorine atom, a trifluoromethyl group and a methyl group.
10. The compound of claim 1 , which is selected from:
5-(4-fluoro-1-benzothien-2-yl)-8-methyl-1,9-dihydro-2H-[1,3]oxazolo[4,5-h][2,3]-benzodiazepin-2-one;
8-methyl-5-(6-quinolyl-1,9-dihydro-2H-[1,3]oxazolo[4,5-h][2,3]benzodiazepin-2-one;
5-(1-benzothien-2-yl)-8-methyl-1,9-dihydro-2H-[1,3]oxazolo[4,5-h][2,3]benzodiazepin-2-one;
5-(5-chloro-1-benzothien-2-yl)-8-methyl-1,9-dihydro-2H-[1,3]oxazolo[4,5-h][2,3]-benzodiazepin-2-one;
5-[3-chloro-4-(trifluoromethyl)-1-benzothien-2-yl]-8-methyl-1,9-dihydro-2H-[1,3]oxazolo[4,5-h][2,3]benzodiazepin-2-one;
8-methyl-5-[4-(trifluoromethyl)-1-benzothien-2-yl]-1,9-dihydro-2H-[1,3]oxazolo[4,5-h][2,3]benzodiazepin-2-one;
5-(6-fluoro-1-benzothien-2-yl)-8-methyl-1,9-dihydro-2H-[1,3]oxazolo[4,5-h][2,3]-benzodiazepin-2-one;
5-(7-fluoro-1-benzothien-2-yl)-8-methyl-1,9-dihydro-2H-[1,3]oxazolo[4,5-h][2,3]-benzodiazepin-2-one.
11. A pharmaceutical composition comprising as active ingredient a compound of claim 1 in combination with one or more inert, non-toxic, pharmaceutically acceptable carriers.
12. A method for treating a condition selected from schizophrenia, unipolar depression, Alzheimer's disease, vascular dementia, autism spectrum disorders, Down's syndrome, fragile X syndrome, Parkinson's disease, Huntington's disease, generalised anxiety, panic disorder with or without agoraphobia, obsessive-compulsive disorders, post-traumatic stress disorders, bipolar disorders, sequalae of a cerebral vascular accident and sequalae of brain, spine or medullary trauma in a subject in need thereof, comprising administration of an effective amount of a compound of claim 1 .