Piperidine compounds
AssigneeAdir et Compagnie
InventorsJean Louis Peglion, Aimee Dessinges, Christophe Poitevin, Mark Millan, Anne Dekeyne
Life of this patent
Estimating the term…
Abstract
A compound selected from those of formula (I): 1 wherein: W represents optionally substituted naphthyl, or group of formula Y 2 as defined in the description, n represents an integer from 1 to 6 inclusive, Z represents single bond, oxygen, or optionally substituted nitrogen, A and Q each represent CH or nitrogen, M, together with carbon of phenyl to which it is bonded, represents thienyl, furyl, pyrrolyl or oxopyrrolyl, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof, and medicinal products containing the same are useful in the treatment of some CNS disorders.
Claims19
1- A compound selected from those of formula (I)
- 13
- wherein:
- W represents
- either naphthyl optionally substituted by one or more identical or different groups selected from halogen, linear or branched (C1-C6)alkyl, hydroxy, linear or branched (C1-C6)alkoxy, cyano, nitro, linear or branched trihalo(C1-C6)alkyl, methylenedioxy, and ethylenedioxy,
- or a group of formula y where:
- 14
- wherein E, together with carbon of phenyl to which it is bonded, represents unsaturated, partially saturated, or aromatic, monocyclic ring having from 5 to 7 ring members and containing at least one hetero atom selected from oxygen, nitrogen and sulphur, it being possible for said group Y to be bonded to (CH2)n group of the compounds of formula (I), either by phenyl, or by monocyclic ring E, and for each of said Y groups to be optionally substituted by one or more identical or different groups selected from halogen, hydroxy, cyano, nitro, linear or branched (C1-C6)alkyl, linear or branched (C1-C6)alkoxy, linear or branched trihalo(C1-C6)alkyl, heterocycloalkylalkylene in which alkylene contains from 1 to 6 carbon and may be linear or branched (and in which heterocyclic is unsaturated, or aromatic monocyclic ring having 5 or 6 ring members, and containing from 1 to 4 hetero atoms selected from nitrogen, sulphur and oxygen) and oxo,
- provided that in that last case Y can be substituted only by a single oxo group, and that E, together with carbon of phenyl to which it is bonded, represents then a monocyclic ring having 5 ring members, and containing two identical or different hetero atoms selected from oxygen, and nitrogen,
- n represents an integer from 1 to 6 inclusive,
- Z represents single bond, oxygen, or nitrogen substituted by a group selected from hydrogen, linear or branched (C1-C6)alkyl (itself optionally substituted by one or more hydroxy) and aryl-(C1-C6)alkyl in which alkyl may be linear or branched,
- A represents CH, or nitrogen,
- Q represents CH, or nitrogen, it being understood that at least one of the groups A and Q represents nitrogen, and that A represents nitrogen when Z represents single bond, and
- M, together with carbon of phenyl to which it is bonded, represents thieno, furo, pyrrolo or oxopyrrolo,
- its isomers, and pharmaceutically-acceptable acid or base addition salts thereof, it being understood that “aryl” is to be understood as phenyl, naphthyl, dihydronaphthyl, or tetrahydronaphthyl.
2- A compound of claim 1, characterised in that W represents a group selected from naphthyl, 2,3-dihydro-1,4-benzodioxinyl, chromanyl, 2H-chromenyl, isochromanyl, 2,3-dihydrobenzofuranyl, benzofuranyl, indolyl, 1,3-dihydro-2H-benzimidazol-2-one and 1,3-benzoxazol-2-one, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
3- A compound of claim 1, characterised in that when W is substituted by heterocycloalkylalkylene in which alkylene moiety contains from 1 to 6 carbon and may be linear or branched, the said heterocycloalkylalkylene is heterocycloalkylmethylene group in which heterocyclic ring is unsaturated, or aromatic monocyclic ring, having 5 ring members and containing from 1 to 4 nitrogen, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
4- A compound of claim 3, characterised in that W is substituted by heterocycloalkylmethylene selected from 1,2,4-triazol-1-ylmethyl, imidazol-1-ylmethyl, and 1H-imidazol-5-ylmethyl, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
5- A compound of claim 1, characterised in that W represents group selected from 1-naphthyl, isochroman-1-yl, and 2,3-dihydrobenzofuran-5-yl, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
6- A compound of claim 1, characterised in that W represents a group selected from 5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl, 5-(imidazol-1-ylmethyl)-1H-indol-3-yl, and 5-(1H-imidazol-5-ylmethyl)-1H-indol-3-yl, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
7- A compound of claim 1, characterised in that W represents group selected from 1,3-benzoxazol-2-on-1-yl, and 1,3-dihydro-2H-benzimidazol-2-on-1-yl, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
8- A compound of claim 1, characterised in that Z represents single bond, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
9- A compound of claim 1, characterised in that, when A represents CH, Q represents nitrogen, n is 1, and W represents 2-naphthyl, Z represents nitrogen substituted by a group selected from hydrogen, methyl, and hydroxyethylene, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
10- A compound of claim 1, characterised in that n represents 2 or 3, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
11- A compound of claim 1, characterised in that M, together with carbon of phenyl to which it is bonded, represents thienyl or furyl, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
12- A compound of claim 1 that is 4-{1-[2-naphthyl)ethyl]-4-piperidinyl}thieno[3,2-c]pyridine, its isomers, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
13- A compound of claim 1 that is 4-{1-[2-(1-naphthyl)ethyl]-4-piperidinyl}furo[3,2-c]pyridine, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
14- A compound of claim 1 that is 4-{4-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-1-piperazinyl}furo[3,2-c]pyridine, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
15- A compound of claim 1 that is 4-{4-[2-(isochroman-1-yl)ethyl]-1-piperazinyl}thieno[3,2-c]pyridine, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
16- A compound of claim 1 that is selected from 4-(4-{2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl}-1-piperazinyl)furo[3,2-c]pyridine, and 4-(4-{2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl}-1-piperazinyl)-1H-pyrrolo[3,2-c]pyridine, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
17- A compound of claim 1 that is selected from 1-[2-(4-furo[3,2-c]pyridin-4-yl-1-piperazinyl)ethyl]-1,3-dihydro-2H-benzimidazol-2-one, and 1-[2-(4-thieno[3,2-c]pyridin-4-yl-1-piperazinyl)ethyl]-1,3-dihydro-2H-benzimidazol-2-one, its isomers, and pharmaceutically-acceptable acid or base addition salts thereof.
18- A method for treating a living body afflicted with a disease like depression, anxiety, panic attacks, obsessive-compulsive disorders, phobias, impulsive disorders, and cognitive disorders, comprising the step of administering to the living body an amount of a compound of claim 1 which is effective for alleviations of said conditions.
19- A pharmaceutical composition useful in the claim 18 method comprising as active principle an effective amount of a compound as claimed in claim 1, together with one or more pharmaceutically-acceptable excipients or vehicles.