Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-08-26
2004-08-03
Chang, Celia (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S212010, C514S235500, C514S316000, C514S330000, C540S597000, C544S130000, C546S189000, C546S210000, C546S211000, C546S225000
Reexamination Certificate
active
06770659
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates, in general, to racemic or enantiomerically enriched benzoyl piperidine compounds and pharmaceutically useful salts thereof, a pharmaceutical composition comprising an effective amount of racemic or enantiomerically enriched benzoyl piperidine compounds to treat central nervous system diseases and a method of treating central nervous system diseases in a mammal. More particularly, the present invention relates to racemic or enantiomerically enriched O-carbamoyl, alkoxy, azole or carbonate benzoyl piperidine compounds and pharmaceutically useful salts thereof, useful to treat the diseases of the central nervous system such as psychosis and cognition disorder. Also, the present invention is concerned with a process for preparing the same.
BACKGROUND OF THE INVENTION
Many reports have disclosed that benzoyl piperidine compounds are effectively used for controlling various central nervous system (CNS) disorders, especially as antipsychotic and analgesics.
1-[n-(2-alkylthio-10H-phenothiazin-10-yl)alkyl]-4-benzoylpiperidines were disclosed in U.S. Pat. No. 4,812,456 and 6,7-dihydro-3-phenyl-1,2-benzisoxazol-4(5H)-ones and -ols were disclosed in U.S. Pat. No. 5,114,936. These compounds are found to be very effective as therapeutical medicines for managing CNS disease, such as antipsychotic and analgesics.
Active research and development efforts have been continued to be directed to the application of benzoyl piperidine compounds for the treatment of CNS disorders.
SUMMARY OF THE INVENTION
A principal object of the present invention is to provide racemic or enantiomerically enriched benzoyl piperidine compounds, represented by the following structural formula (I) and pharmaceutically acceptable salts thereof:
wherein
n is 0; and
A is selected from the group consisting of phenyl which may be substituted with one or more identical or different substituents selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms, straight or branched chain alkoxy of from 1 to 3 carbon atoms, nitro, cyano, trifluoromethyl, trifluoromethoxy, methanesulfonyl and phenyl; thienyl; naphthyl; pyridyl; and quinolyl; or
n is an integer from 1 to 2; and
A is selected from the group consisting of phenyl or phenoxy which may be substituted with one or more identical or different substituents selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms, straight or branched chain alkoxy of from 1 to 3 carbon atoms, nitro, cyano, trifluoromethyl, trifluoromethoxy, methanesulfonyl and phenyl; thienyl; naphthyl; pyridyl; and quinolyl;
X is selected from the group consisting of O-carbamoyl, straight or branched chain alkoxy of from 1 to 4 carbon atoms, imidazole, triazole, tetrazole and carbonate; and
Y is selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms and straight or branched chain alkoxy of from 1 to 3 carbon atoms.
More specifically, the present benzoyl piperidine compounds represented by the above formula (I) comprises racemic or enantiomerically enriched compounds represented by the following structural formula (V), (VIII), (XIV), and (XVI):
wherein
n is 0 ; and
A is selected from the group consisting of phenyl which may be substituted with one or more identical or different substituents selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms, straight or branched chain alkoxy of from 1 to 3 carbon atoms, nitro and trifluoromethyl; and naphthyl; or
n is an integer from 1 to 2; and
A is selected from the group consisting of phenyl or phenoxy which may be substituted with one or more identical or different substituents selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms, straight or branched chain alkoxy of from 1 to 3 carbon atoms, nitro and trifluoromethyl; and naphthyl;
Y is selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms and straight or branched chain alkoxy of from 1 to 3 carbon atoms; and
R1 and R2 may be the same with or different from each other and are independently selected from the group consisting of hydrogen, methoxy, benzyl and 5 to 7-membered aliphatic cyclic compounds:
wherein
n is 0; and
A is selected from the group consisting of phenyl which may be substituted with one or more identical or different substituents selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms, straight or branched chain alkoxy of from 1 to 3 carbon atoms, nitro, cyano, trifluoromethyl, trifluoromethoxy, methanesulfonyl, phenyl; thienyl; naphthyl; pyridyl; and quinolyl; or
n is an integer from 1 to 2; and
A is selected from the group consisting of phenyl or phenoxy which may be substituted with one or more identical or different substituents selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms, straight or branched chain alkoxy of from 1 to 3 carbon atoms, nitro, cyano, trifluoromethyl, trifluoromethoxy, methanesulfonyl, phenyl; thienyl; naphthyl; pyridyl; and quinolyl;
Y is selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms, and straight or branched chain alkoxy of from 1 to 3 carbon atoms; and
R3 is selected from the group consisting of straight or branched chain alkyl of from 1 to 4 carbon atoms, aliphatic cyclic compound of from 5 to 7 carbon atoms, and benzyl:
wherein
n is an integer from 0 to 2;
A is selected from the group consisting of phenyl which may be substituted with one or more identical or different substituents selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms, straight or branched chain alkoxy of from 1 to 3 carbon atoms, nitro and trifluoromethyl; and naphthyl;
Y is selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms, and straight or branched chain alkoxy of from 1 to 3 carbon atoms; and
X is imidazole, triazole, or tetrazole moiety having the following formula (XII):
wherein
n is 0 ; and
A is selected from the group consisting of phenyl which may be substituted with one or more identical or different substituents selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms, straight or branched chain alkoxy of from 1 to 3 carbon atoms, nitro, cyano and trifluoromethyl; or
n is an integer from 1 to 2; and
A is selected from the group consisting of phenyl or phenoxy which may be substituted with one or more identical or different substituents selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms, straight or branched chain alkoxy of from 1 to 3 carbon atoms, nitro, cyano and trifluoromethyl;
Y is selected from the group consisting of hydrogen, halogen, straight or branched chain alkyl of from 1 to 4 carbon atoms, and straight or branched chain alkoxy of from 1 to 3 carbon atoms; and
R4 is selected from the group consisting of straight or branched chain alkyl of from 1 to 3 carbon atoms, phenyl and benzyl.
It is another object of the present invention to provide a pharmaceutical composition comprising an effective amount of racemic or enantiomerically enriched benzoyl piperidine compounds represented by the above structural formula (I), in particular, the compounds represented by the above structural formula (V), (VIII), (XIV) and (XVI), for treating disorders of central nervous system such as psychosis and cognition disorder.
It is still another object of the present invention to provide a method of treating disorders of central nervous system such as psychosis and cognition disorder in a mammal by admin
Choi Yong-Moon
Chung Coo-Min
Heo Joon
Kim Yong-Kil
Paek Eun-Ah
Chang Celia
Gibbons, Del Deo, Dolan Griffinger and Vecchione
SK Corporation
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