US4246269A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Antidepressant piperidinones
Assignee: Novartis Corp
•
Filing: 1979-04-05
•
Granted: 1981-01-20
•
Expires: 1999-04-05
Abstract
Abstract The present invention provides new derivatives of perhydro-aza-heterocycles of the formula <IMAGE> (I) in which X is the oxo radical or hydrogen and the radical OR1, in which R1 is hydrogen or a substituted or unsubstituted aliphatic hydrocarbon radical, a substituted or unsubstituted araliphatic hydrocarbon radical or a substituted or unsubstituted aromatic hydrocarbon radical or an acyl radical, R2 is hydrogen or a substituted or unsubstituted aliphatic hydrocarbon radical, Y is oxygen or sulphur, n1 and n2 each are values of 1 to 3, n1+n2 being at most four, and Ar is a substituted or unsubstituted aromatic hydrocarbon radical, and the acid addition salts, in particular the pharmaceutically acceptable acid addition salts thereof. These new substances possess valuable pharmacological properties, in particular antidepressant activity, and can be used for the treatment of mental depressions. Specific embodiments are trans- and cis-3-hydroxy-4-(3,4-dimethyl-phenoxy)-piperidine, trans- and cis-3-hydroxy-4-(2,3-dimethyl-phenoxy)-piperidine, their 1-methyl derivatives and the pharmaceutically acceptable salts of these substances.
Inventors
- 👤 Romeo Paioni
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 09:01
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/02; C07D491/04; A; A61; A61P; A61P25/00; A61P25/18; A61P25/24; A61P25/26; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/12; C07D207/18; C07D207/22; C07D207/24; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/42; C07D211/44; C07D211/46; C07D211/54; C07D211/68; C07D211/72; C07D211/74; C07D223/00; C07D223/02; C07D223/06; C07D223/08
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
94 words
A compound of the formula ##STR9## wherein X is the oxo radical, R 2 is hydrogen, lower alkyl, lower alkenyl or lower alkynyl, Ar is phenyl, naphthyl or 5,6,7,8-tetrahydronaphthyl, which are unsubstituted or mono- or disubstituted in an aromatic ring, at most two substituents being selected from lower alkyl, lower alkoxy and halogen, and at most one substituent being selected from trifluoromethyl, carbamoyl, nitro and cyano, Y is oxygen, n 1 is one and n 2 is two and n 1 is two and n 2 is 1 or an acid addition salt thereof.
Claim 2
Dependent Claim
94 words
A compound of the formula ##STR9## wherein X is the oxo radical, R 2 is hydrogen, lower alkyl, lower alkenyl or lower alkynyl, Ar is phenyl, naphthyl or 5,6,7,8-tetrahydronaphthyl, which are unsubstituted or mono- or disubstituted in an aromatic ring, at most two substituents being selected from lower alkyl, lower alkoxy and halogen, and at most one substituent being selected from trifluoromethyl, carbamoyl, nitro and cyano, Y is oxygen, n 1 is one and n 2 is two and n 1 is two and n 2 is 1 or an acid addition salt thereof.
Claim 3
Dependent Claim
83 words
A compound according to claim 1 in which X is the oxo radical, R 2 is hydrogen, lower alkyl or propargyl, Ar is phenyl, naphthyl or 5,6,7,8-tetrahydronaphthyl, and phenyl is unsubstituted or mono- or disubstituted by lower alkyl, lower alkoxy or halogen, or substituted by trifluoromethyl, said substituents being identical or different from one another, Y is oxygen, n 1 is one and n 2 is two or n 1 is two and n 2 is one, or an acid addition salt thereof.
Claim 4
Dependent Claim
73 words
A compound according to claim 1 in which X is the oxo radical, R 2 is hydrogen, lower alkyl or propargyl, Ar is phenyl, naphthyl or 5,6,7,8-tetrahydronaphthyl, and phenyl is unsubstituted or mono- or disubstituted by lower alkyl, lower alkoxy or halogen, or substituted by trifluoromethyl, said substituents being identical or different from one another, Y is oxygen, n 1 is one and n 2 is two or an acid addition salt thereof.
Claim 5
Dependent Claim
17 words
A compound according to claim 1 which is 4-(3,4-dimethyl-phenoxy)-3-piperidone or a pharmaceutically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
17 words
A compound according to claim 1 which is 4-(2,3-dimethyl-phenoxy)-3-piperidone or a pharmaceutically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
125 words
A pharmaceutical composition for the treatment of mental depression comprising a therapeutically effective amount of a compound of the formula ##STR10## wherein X is the oxo radical, R 2 is hydrogen, lower alkyl, lower alkenyl or lower alkynyl, Ar is phenyl, naphthyl or 5,6,7,8-tetrahydronaphthyl which are unsubstituted or mono- or disubstituted in an aromatic ring, at most two substituents being selected from lower alkyl, lower alkoxy, and halogen, and at most one substituent being selected from trifluoromethyl, carbamoyl, nitro and cyano, said substituents being identical or different from one another, Y is oxygen, n 1 is one and n 2 is two or n 1 is two and n 2 is one, or a pharmaceutical acceptable acid addition salt thereof together with a pharmaceutical excipient.
Claim 8
Dependent Claim
125 words
A pharmaceutical composition for the treatment of mental depression comprising a therapeutically effective amount of a compound of the formula ##STR10## wherein X is the oxo radical, R 2 is hydrogen, lower alkyl, lower alkenyl or lower alkynyl, Ar is phenyl, naphthyl or 5,6,7,8-tetrahydronaphthyl which are unsubstituted or mono- or disubstituted in an aromatic ring, at most two substituents being selected from lower alkyl, lower alkoxy, and halogen, and at most one substituent being selected from trifluoromethyl, carbamoyl, nitro and cyano, said substituents being identical or different from one another, Y is oxygen, n 1 is one and n 2 is two or n 1 is two and n 2 is one, or a pharmaceutical acceptable acid addition salt thereof together with a pharmaceutical excipient.
Claim 9
Dependent Claim
108 words
A pharmaceutical composition according to claim 6 wherein a therapeutically effective amount of a compound of formula I given in claim 24, in which X is the oxo radical, R 2 is hydrogen, lower alkyl or propargyl, Ar is phenyl, naphthyl or 5,6,7,8-tetrahydronaphthyl, and phenyl is unsubstituted or mono- or disubstituted by lower alkyl, lower alkoxy or halogen, or substituted by trifluoromethyl, said substituents being identical or different from one another, Y is oxygen, n 1 is one and n 2 is two or n 1 is two and n 2 is one, or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutical excipient, is present.
Claim 10
Dependent Claim
98 words
A pharmaceutical composition according to claim 6, wherein a therapeutically effective amount of a compound of formula I given in claim 24, in which X is the oxo radical, R 2 is hydrogen, lower alkyl or propargyl, Ar is phenyl, naphthyl or 5,6,7,8-tetrahydronaphthyl, and phenyl is unsubstituted or mono- or disubstituted by lower alkyl, lower alkoxy or halogen, or substituted by trifluoromethyl, said substituents being identical or different from one another, Y is oxygen, n 1 is one and n 2 is two or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutical excipient, is present.
Claim 11
Dependent Claim
30 words
A pharmaceutical composition according to claim 6 wherein a therapeutically effective amount of 4-(3,4-dimethyl-phenoxy)-3-piperidone or of a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutical excipient, is present.
Claim 12
Dependent Claim
30 words
A pharmaceutical composition according to claim 6 wherein a therapeutically effective amount of 4-(2,3-dimethyl-phenoxy)-3-piperidone or of a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutical excipient, is present.
Claim 13
Dependent Claim
49 words
A method for the treatment of mental depression in a warm-blooded animal comprising enteral or parenteral administration to said animal of a therapeutically effective amount of a compound according to claim 1 having the formula 1 defined in claim 1, or of a pharmaceutically acceptable acid addition salt thereof.
References Cited (Backward Citations)
US2865930A
Cited
US3117975A
Cited
US3260723A
Cited
US3542794A
Cited
US3686169A
Cited
US3743645A
Cited
US4065290A
Cited
US4160837A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-01-20 | 1984-07-21 | 1985-01-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-01-20 | 1988-07-21 | 1989-01-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-01-20 | 1992-07-21 | 1993-01-20 | $7700.00 | Window Closed / Lapsed |