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US4232031A
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Process for preparation of piperidyl-indoles
Assignee: Sanofi Aventis France
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Filing: 1979-12-06
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Granted: 1980-11-04
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Expires: 1999-12-06
Abstract
Abstract A novel process for the preparation of piperidylindoles of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms and X is selected from the group consisting of hydrogen, nitro, fluorine, bromine, chlorine and alkoxy of 1 to 3 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts thereof by reacting an indole of the formula ##STR2## with 4-piperidone hydrochloride in an alkaline medium to obtain the compound of formula I which is optionally salified and the novel product, 5-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole and its non-toxic, pharmaceutically acceptable acid addition salts.
Inventors
- 👤 Claude Dumont
- 👤 Jacques Guillaume
- 👤 Lucien Nedelec
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 15:04
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; A; A61; A61P; A61P1/00; A61P1/08; A61P25/00; A61P25/18; A61P25/20
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
84 words
A process for the preparation of piperidyl-indoles of the formula ##STR6## wherein X is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, alkoxy of 1 to 3 carbon atoms and nitro and R is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms comprising reacting an indole of the formula ##STR7## with 4-piperidone hydrochloride in an alkaline medium to form the compound of formula I and optionally salifying the latter to obtain its acid addition salt.
Claim 2
Dependent Claim
84 words
A process for the preparation of piperidyl-indoles of the formula ##STR6## wherein X is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, alkoxy of 1 to 3 carbon atoms and nitro and R is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms comprising reacting an indole of the formula ##STR7## with 4-piperidone hydrochloride in an alkaline medium to form the compound of formula I and optionally salifying the latter to obtain its acid addition salt.
Claim 3
Dependent Claim
16 words
The process of claim 1 wherein the basic media is 2 N methanolic potassium hydroxide solution.
Claim 4
Dependent Claim
12 words
The process of claim 1 wherein the reaction is effected at reflux.
Claim 5
Dependent Claim
17 words
A compound selected from the group consisting of 5-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 6
Dependent Claim
17 words
A compound selected from the group consisting of 5-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 7
Dependent Claim
27 words
A composition having antidepressive, antiemetic and antiparkinsonian activity comprising an effective amount of 5-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole and its non-toxic, pharmaceutically acceptable acid addition salts and an inert pharmaceutical carrier.
Claim 8
Dependent Claim
27 words
A composition having antidepressive, antiemetic and antiparkinsonian activity comprising an effective amount of 5-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole and its non-toxic, pharmaceutically acceptable acid addition salts and an inert pharmaceutical carrier.
Claim 9
Independent Claim
31 words
A method of treating psychic disorders in warm-blooded animals comprising administering to warm-blooded animals an amount of 5-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole and its non-toxic, pharmaceutically acceptable acid addition salts sufficient to relieve psychic disorders.
Claim 10
Independent Claim
31 words
A method of treating psychic disorders in warm-blooded animals comprising administering to warm-blooded animals an amount of 5-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole and its non-toxic, pharmaceutically acceptable acid addition salts sufficient to relieve psychic disorders.
References Cited (Backward Citations)
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-11-04 | 1984-05-05 | 1984-11-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-04 | 1988-05-05 | 1988-11-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-04 | 1992-05-05 | 1992-11-04 | $7700.00 | Window Closed / Lapsed |