US3980658A
Expired / Lapsed
US
⏱️ 0.0 years remaining
(Indolyl-piperidino or -1,2,5,6-tetrahydro-pyridyl)-p-fluoro-butyrophenones and salts thereof
Assignee: Boehringer Ingelheim GmbH
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Filing: 1974-05-06
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Granted: 1976-09-14
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Expires: 1994-05-06
Abstract
Abstract Compounds of the formula WHEREIN R1 is hydrogen, chlorine, methyl, methoxy or trifluoromethyl, R2 is hydrogen or methyl, R3 is methyl or phenyl, and R4 and R5 together form a double bond or, in case R1 is chloro, methyl or trifluoromethyl, are also hydrogen atoms, AND NON-TOXIC, PHARMACOLOGICALLY ACCEPTABLE ACID ADDITION SALTS THEREOF; THE COMPOUNDS AS WELL AS THEIR SALTS ARE USEFUL AS SEDATIVES AND TRANQUILIZERS.
Inventors
- 👤 Genus Possanza
- 👤 Kurt Freter
- 👤 Sven Luttke
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 06:32
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
58 words
A compound of the formula ##SPC15## wherein R 1 is hydrogen, chlorine, methyl or methoxy, R 2 is hydrogen or methyl, R 3 is methyl or phenyl, and R 4 and R 5 together form a double bond or, when R 1 is chlorine or methyl, are also hydrogen, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
58 words
A compound of the formula ##SPC15## wherein R 1 is hydrogen, chlorine, methyl or methoxy, R 2 is hydrogen or methyl, R 3 is methyl or phenyl, and R 4 and R 5 together form a double bond or, when R 1 is chlorine or methyl, are also hydrogen, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
39 words
A compound of claim 1, wherein R 1 is chlorine, R 2 is hydrogen or methyl, R 3 is methyl or phenyl, and R 4 and R 5 are hydrogen, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 4
Dependent Claim
17 words
A compound of claim 1, which is 4-[4'-(5"-chloro-2"-methyl-3"-indolyl)-piperidino]-p-flouro-butyrophenone or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 5
Dependent Claim
17 words
A compound of claim 1, which is 4-[4'-(5"-chloro-2"-methyl-3"-indolyl)-1',2',5',6'-tetrahydro-1'-pyridyl]-p-fluoro-butyrophenone or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
17 words
A compound of claim 1, which is 4-[4'-(5"-methoxy-2"-methyl-3"-indolyl)-1',2',5',6'-tetrahydro-1'-pyridyl]-p-fluoro-butyrophenone or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
17 words
A compound of claim 1, which is 4-[4'-(1",2"-dimethyl-3"-indolyl)-1',2',5',6'-tetrahydro-1'-pyridyl]-p-fluoro-butyrophenone or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 8
Dependent Claim
17 words
A compound of claim 1, which is 4-[4'-(2"-methyl-3"-indolyl)-1',2',5',6'-tetrahydro-1'-pyridyl]-p-fluoro-butyrophenone or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 9
Dependent Claim
17 words
A compound of claim 1, which is 4-[4'-(5"-chloro-1",2"-dimethyl-3"-indolyl)-1',2',5',6'-tetrahydro-1'-pyridyl]-p-fluoro-butyrophenone or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 10
Dependent Claim
17 words
A compound of claim 1, which is 4-[4'-(2",5"-dimethyl-3"-indolyl)-1',2',5',6'-tetrahydro-1'-pyridyl]-p-fluoro-butyrophenone or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 11
Dependent Claim
17 words
A compound of claim 1, which is 4-[4'-(1"-methyl-2"-phenyl-3"-indolyl)-1',2',5',6'-tetrahydro-1'-pyridyl]-p-fluoro-butyrophenone or a non-toxic, pharmacologically acceptable acid addition salt thereof.
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) | 1979-09-14 | 1980-03-15 | 1980-09-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-09-14 | 1984-03-15 | 1984-09-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-09-14 | 1988-03-15 | 1988-09-14 | $7700.00 | Window Closed / Lapsed |