US4021564A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Neuroleptic piperidine compounds
Assignee: Pharmacia Animal Health Inc
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Filing: 1976-05-03
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Granted: 1977-05-03
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Expires: 1996-05-03
Abstract
Abstract Novel 1-substituted-4-aroyl-4-hydroxy and -4-acyloxypiperidines and acid addition salts thereof, useful as central nervous system depressants and neuroleptics with pronounced antipsychotic effects, are disclosed. Methods of making same, pharmaceutical compositions thereof, a method of treating therewith, and important and novel intermediates for the production thereof, are also disclosed.
Inventors
- 👤 Sven Erik Harry Hernestam
- 👤 Anders Karl Konrad Bjork
- 👤 Aina Lisbeth Abramo
- 👤 Bengt Erik Sigvard Kjellberg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 15:20
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/48; C07D211/50; A; A61; A61P; A61P25/00; A61P25/20
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
77 words
A compound selected from the group consisting of (a) 1-(3-benzoylpropyl)-4-benzoyl-4-hydroxy or -4-acyloxypiperidines having the formula ##STR22## wherein R 1 and R 2 independently represent hydrogen, a lower-alkyl group of one to five carbon atoms inclusive, fluorine, chlorine, bromine, lower-alkoxy of one to five carbon atoms inclusive, or trifluoromethyl, R 4 represents hydrogen or an acyl group of two to nineteen carbon atoms inclusive, and R represents fluorine, chlorine, bromine, or trifluoromethyl, and (b) acid addition salts thereof.
Claim 2
Dependent Claim
77 words
A compound selected from the group consisting of (a) 1-(3-benzoylpropyl)-4-benzoyl-4-hydroxy or -4-acyloxypiperidines having the formula ##STR22## wherein R 1 and R 2 independently represent hydrogen, a lower-alkyl group of one to five carbon atoms inclusive, fluorine, chlorine, bromine, lower-alkoxy of one to five carbon atoms inclusive, or trifluoromethyl, R 4 represents hydrogen or an acyl group of two to nineteen carbon atoms inclusive, and R represents fluorine, chlorine, bromine, or trifluoromethyl, and (b) acid addition salts thereof.
Claim 3
Dependent Claim
13 words
Pharmacologically acceptable acid addition salt of a basic piperidine ketone of claim 1.
Claim 4
Dependent Claim
14 words
Compound of claim 1 wherein R 1 is methyl and R 2 is hydrogen.
Claim 5
Dependent Claim
14 words
Compound of claim 1 wherein R 1 is methoxy and R 2 is hydrogen.
Claim 6
Dependent Claim
14 words
Compound of claim 1 wherein R 1 is fluoro and R 2 is hydrogen.
Claim 7
Dependent Claim
14 words
Compound of claim 1 wherein R 1 is bromo and R 2 is hydrogen.
Claim 8
Dependent Claim
14 words
Compound of claim 1 wherein R 1 is trifluoromethyl and R 2 is hydrogen.
Claim 9
Dependent Claim
14 words
Compound of claim 1 wherein R 1 is hydrogen and R 2 is hydrogen.
Claim 10
Dependent Claim
14 words
Compound of claim 1 wherein R 1 is chloro and R 2 is hydrogen.
Claim 11
Dependent Claim
14 words
Compound of claim 1 wherein R 1 is chloro and R 2 is trifluoromethyl.
Claim 12
Dependent Claim
14 words
Compound of claim 1 wherein R 1 is methyl and R 2 is methyl.
Claim 13
Dependent Claim
14 words
Compound of claim 1 wherein R 1 is chloro and R 2 is chloro.
Claim 14
Dependent Claim
8 words
Compound of claim 1 wherein R is fluoro.
Claim 15
Dependent Claim
9 words
Compound of claim 1 wherein R 4 is hydrogen.
Claim 16
Dependent Claim
10 words
Compound of claim 1 which is 1-[3-(p-fluorobenzoyl)propyl]-4-(p-fluorobenzoyl)-4-hydroxypiperidine acid addition salt.
Claim 17
Dependent Claim
8 words
Compound of claim 1 which is 1-[3-(p-fluorobenzoyl)-propyl]-4-(p-fluorobenzoyl)-4-hydroxypiperidine hydrochloride.
Claim 18
Dependent Claim
10 words
Compound of claim 1 which is 4-lower-alkanoyloxy-4-(p-fluorobenzoyl)-1-[3-(p-fluorobenzoyl)-propyl]-piperidine acid addition salt.
Claim 19
Dependent Claim
10 words
Compound of claim 1 which is 4-propionyloxy-4-(p-fluorobenzoyl)-1-[3-(p-fluorobenzoyl)-propyl]-piperidine acid addition salt.
Claim 20
Dependent Claim
10 words
Compound of claim 1 which is 1-[3-(p-fluorobenzoyl)-propyl]-4-(p-methylbenzoyl)-4-hydroxypiperidine acid addition salt.
Claim 21
Dependent Claim
10 words
Compound of claim 1 which is 1-[3-(p-fluorobenzoyl)-propyl]-4-(p-methoxybenzoyl)-4-hydroxypiperidine acid addition salt.
Claim 22
Dependent Claim
10 words
Compound of claim 1 which is 1-[3-(p-fluorobenzoyl)-propyl]-4-(p-bromobenzoyl)-4-hydroxypiperidine acid addition salt.
Claim 23
Dependent Claim
10 words
Compound of claim 1 which is 1-[3-(p-fluorobenzoyl)-propyl]-4-(m-trifluoromethylbenzoyl)-4-hydroxypiperidine acid addition salt.
Claim 24
Dependent Claim
8 words
Compound of claim 1 which is 1-[3-(p-fluorobenzoyl)-propyl]-4(3-trifluoromethyl-4-chlorobenzoyl)-4-hydroxypiperidine hydrochloride.
Claim 25
Dependent Claim
10 words
Compound of claim 1 which is 1-[3-(p-fluorobenzoyl)-propyl]-4-benzoyl-4-hydroxypiperidine acid addition salt.
Claim 26
Dependent Claim
10 words
Compound of claim 1 which is 1-[3-(p-fluorobenzoyl)-propyl]-4-(p-chlorobenzoyl)-4-hydroxypiperidine acid addition salt.
Claim 27
Dependent Claim
10 words
Compound of claim 1 which is 4-butyryloxy-4-(p-fluorobenzoyl)-1-[3-(p-fluorobenzoyl)-propyl]-piperidine acid addition salt.
Claim 28
Dependent Claim
10 words
Compound of claim 1 which is 4-octanoyloxy-4-(p-fluorobenzoyl)-1-[3-(p-fluorobenzoyl)-propyl]-piperidine acid addition salt.
Claim 29
Dependent Claim
8 words
Compound of claim 1 which is 4-propionyloxy-4-(p-methoxybenzoyl)-1-[3-(p-fluorobenzoyl)-propyl]-piperidine hydrochloride.
Claim 30
Dependent Claim
10 words
Compound of claim 1 which is 1-[3-(p-fluorobenzoyl)-propyl]-4-(3,4-dichlorobenzoyl)-4-hyroxypiperidine acid addition salt.
Claim 31
Dependent Claim
10 words
Compound of claim 1 which is 1-[3-(p-fluorobenzoyl)-propyl]-4-(3,4-dimethylbenzoyl)-4-hydroxypiperidine acid addition salt.
Claim 32
Dependent Claim
31 words
A pharmaceutical composition suitable for use in the alleviation of psychotic conditions comprising a compound of claim 1, in an amount effective for said purpose, in association with a pharmaceutical carrier.
Claim 33
Dependent Claim
35 words
Method for the treatment of a patient suffering from a psychotic, manic, or neurotic state, comprising administering to the patient a compound of claim 1 in an amount effective for the alleviation of said condition.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-05-02 | 1980-11-01 | 1981-05-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-02 | 1984-11-01 | 1985-05-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-02 | 1988-11-01 | 1989-05-03 | $7700.00 | Window Closed / Lapsed |