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US 2007/0191358 A1Published application
Novel piperidine derivative for the treatment of depression
AssigneeAstraZeneca AB
InventorsJames Folmer, Simon Hunt, Peter Hamley, Steven Wesolowski
Life of this patent
Estimating the term…
Abstract
Compounds of formula: (chemical formula to be inserted here—please see paper copy) wherein Arl is as defined in the specification, as well as salts, enantiomers thereof and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the treatment of depression.
Claims9
A compound of formula I, a pharmaceutically acceptable salt thereof, diastereomers, enantiomers, or mixtures thereof:
- wherein
- Ar1 is selected from C6-10aryl and C2-9heteroaryl, wherein said C6-10aryl and C2-9heteroaryl are optionally substituted with one or more groups selected from —R, —NO2, —OR, —Cl, —Br, —I, —F, —CF3, —OCF3, —C(═O)R, —C(═O)OH, —NH2, —SH, —NHR, —NR2, —SR, —SO3H, —SO2R, —SO2NR, —S(═O)R, —CN, —OH, —C(═O)OR, —C(═O)NR2, —NRC(═O)R, and —NRC(═O)—OR, wherein R is, independently, a hydrogen, C3-6cycloalkyl, C3-6heterocyclyl, phenyl, benzyl, C1-6alkyl or C2-6alkenyl and wherein said R is further optionally substituted with one or more groups selected from methyl, hydroxy and halogen, or Ar1 is represented by
- wherein Ar is selected from phenyl, pyridyl, naphthyl, benzo[1,3]dioxolyl, quinolyl, indolyl, benzotriazolyl, benzoimidazolyl, 2,3-dihydro-benzofuranyl, benzo[1,2,3]thiadiazolyl, benzothiazolyl, and 4H-benzo[1,4]oxazin-3-on-yl;
- R1, R2 and R3 are independently selected from —R, —NO2, —OR, —Cl, —Br, —I, —F, —CF3, —C(═O)R, —C(═O)OH, —NH2, —SH, —NHR, —NR2, —SR, —SO3H, —SO2R, —SO2NR, —S(═O)R, —CN, —OH, —C(═O)OR, —C(═O)NR2, —NRC(═O)R, and —NRC(═O)—OR, wherein R is, independently, a hydrogen, C5-6cycloalkyl, C3-5heterocyclyl, phenyl, benzyl, C1-4alkyl or C2-4alkenyl, and wherein said R is further optionally substituted with one or more groups selected from methyl, hydroxy and halogen.
1 more element
A compound selected from:
- and pharmaceutically acceptable salts thereof.
5-6. (canceled)
A process for preparing a compound of formula I, comprising:
- reacting Ar1-COX or (Ar1—CO)2O with 3-(1-piperidino)propylamine,
- wherein Ar1 is selected from C6-10aryl and C2-9heteroaryl, wherein said C6-10aryl and C2-9heteroaryl are optionally substituted with one or more groups selected from —R, —NO2, —OR, —Cl, —Br, —I, —F, —CF3, —OCF3, —C(═O)R, —C(═O)OH, —NH2, —SH, —NHR, —NR2, —SR, —SO3H, —SO2R, —SO2NR, —S(═O)R, —CN, —OH, —C(═O)OR, —C(═O)NR2, —NRC(═O)R, and —NRC(═O)—OR, wherein R is, independently, a hydrogen, —C3-6cycloalkyl, C3-6heterocyclyl, phenyl, benzyl, C1-6alkyl or C2-6alkenyl and wherein said R is further optionally substituted with one or more groups selected from methyl, hydroxy and halogen, and
- X is selected from —OH and halogen.
A process for preparing a compound of formula I, comprising:
- combining Ar1-COX or (Ar1-CO)2O with 3-(1-piperidino)propylamine,
- wherein Ar1 is represented by
- wherein Ar is selected from phenyl, pyridyl, naphthyl, benzo[1,3]dioxolyl, quinolyl, indolyl, benzotriazolyl, benzoimidazolyl, 2,3-dihydro-benzofuranyl, benzo[1,2,3]thiadiazolyl, benzothiazolyl, and 4H-benzo[1,4]oxazin-3-on-yl;
- R1, R2 and R3 are independently selected from —R, —NO2, —OR, —Cl, —Br, —I, —F, —CF3, —C(═O)R, —C(═O)OH, —NH2, —SH, —NHR, —NR2, —SR, —SO3H, —SO2R, —SO2NR, —S(═O)R, —CN, —OH, —C(═O)OR, —C(═O)NR2, —NRC(═O)R, and —NRC(═O)—OR, wherein R is, independently, a hydrogen, C5-6cycloalkyl, C3-5heterocyclyl, phenyl, benzyl, C1-4alkyl or C2-4alkenyl, and wherein said R is further optionally substituted with one or more groups selected from methyl, hydroxy and halogen;
- and
- X is selected from —OH and halogen.
3 more elements
Dependencies are inferred from the claim text.