US4278677A
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Tetrahydropyridinyl indoles
Assignee: Sanofi Aventis France
•
Filing: 1979-01-10
•
Granted: 1981-07-14
•
Expires: 1999-01-10
Abstract
Abstract Novel tetrahydropyridinyl indoles of the formula ##STR1## wherein R' is selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 3 carbon atoms, R 1 and R 2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms and X' is selected from the group consisting of alkyl of 1 to 6 carbon atoms, cycloalkyl of 4 to 7 carbon atoms, alkenyl and alkynyl of 2 to 5 carbon atoms and aralkyl of 7 to 12 carbon atoms with the proviso that when X' is methyl, at least one of R', R 1 and R 2 contain more than one carbon atom and when X' is benzyl, at least one of R', R 1 and R 2 must not be hydrogen and their non-toxic, pharmaceutically acceptable acid addition salts having antidepressive and neuroleptic properties as well as antiemetic properties.
Inventors
- 👤 Lucien Nedelec
- 👤 Jacques Guillaume
- 👤 Claude Dumont
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 16:03
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; A; A61; A61P; A61P1/00; A61P1/08; A61P25/00; A61P25/18; A61P25/24; A61P25/26
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
145 words
A compound selected from the group consisting of compounds of the formula ##STR7## wherein R' is selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 3 carbon atoms, R 1 and R 2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms and X' is selected from the group consisting of alkyl of 1 to 6 carbon atoms, cycloalkyl of 4 to 7 carbon atoms, alkenyl and alkynyl of 2 to 5 carbon atoms and aralkyl of 7 to 12 carbon atoms with the proviso that when X' is methyl, at least one of R', R 1 and R 2 contain more than one carbon atom and when X' is benzyl, at least one of R', R 1 and R 2 must not be hydrogen and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 2
Dependent Claim
145 words
A compound selected from the group consisting of compounds of the formula ##STR7## wherein R' is selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 3 carbon atoms, R 1 and R 2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms and X' is selected from the group consisting of alkyl of 1 to 6 carbon atoms, cycloalkyl of 4 to 7 carbon atoms, alkenyl and alkynyl of 2 to 5 carbon atoms and aralkyl of 7 to 12 carbon atoms with the proviso that when X' is methyl, at least one of R', R 1 and R 2 contain more than one carbon atom and when X' is benzyl, at least one of R', R 1 and R 2 must not be hydrogen and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 3
Dependent Claim
57 words
A compound of claim 1 wherein R' is selected from the group consisting of hydrogen and alkoxy of 1 to 3 carbon atoms and X' is alkyl of 1 to 6 carbon atoms with the proviso that when X' is methyl, at least one of R', R 1 and R 2 contain more than one carbon atom.
Claim 4
Dependent Claim
29 words
A compound of claim 1 wherein R' is halogen, R 1 and R 2 are individually hydrogen or methyl and X' is alkyl of 2 to 6 carbon atoms.
Claim 5
Dependent Claim
26 words
A compound of claim 1 wherein R' is 5-chloro, R 1 and R 2 are hydrogen and X' is alkyl of 2 to 6 carbon atoms.
Claim 6
Dependent Claim
31 words
A compound of claim 2 wherein R' is hydrogen or methoxy, R 1 and R 2 are individually hydrogen or methyl and X' is alkyl of 2 to 6 carbon atoms.
Claim 7
Dependent Claim
28 words
A compound of claim 2 wherein R' is hydrogen or 5-methoxy, R 1 and R 2 are hydrogen and X' is alkyl of 2 to 6 carbon atoms.
Claim 8
Dependent Claim
12 words
A compound of claim 2 which is the neutral fumarate of 5-methoxy-3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole.
Claim 9
Dependent Claim
10 words
A compound of claim 2 which is the 3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 10
Dependent Claim
10 words
A compound of claim 2 which is the 3-(1-pentyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 11
Dependent Claim
10 words
A compound of claim 1 which is the 5-chloro-3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 12
Dependent Claim
10 words
A compound of claim 1 which is the 3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 13
Dependent Claim
10 words
A compound of claim 1 which is the 3-(1-isopropyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 14
Dependent Claim
10 words
A compound of claim 1 which is the 6-methoxy-3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 15
Dependent Claim
27 words
An antidepressive, neuroleptic and antiemetic composition comprising an antidepressantly, neuroleptically and antiemetically effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.
Claim 16
Dependent Claim
57 words
A composition of claim 14 wherein R' is selected from the group consisting of hydrogen and alkoxy of 1 to 3 carbon atoms and X' is alkyl of 1 to 6 carbon atoms with the proviso that when X' is methyl, at least one of R', R 1 and R 2 contain more than one carbon atom.
Claim 17
Dependent Claim
29 words
A composition of claim 14 wherein R' is halogen, R 1 and R 2 are individually hydrogen or methyl and X' is alkyl of 2 to 6 carbon atoms.
Claim 18
Dependent Claim
26 words
A composition of claim 14 wherein R' is 5-chloro, R 1 and R 2 are hydrogen and X' is alkyl of 2 to 6 carbon atoms.
Claim 19
Dependent Claim
31 words
A composition of claim 14 wherein R' is hydrogen or methoxy, R 1 and R 2 are individually hydrogen or methyl and X' is alkyl of 2 to 6 carbon atoms.
Claim 20
Dependent Claim
28 words
A composition of claim 14 wherein R' is hydrogen or 5-methoxy, R 1 and R 2 are hydrogen and X' is alkyl of 2 to 6 carbon atoms.
Claim 21
Dependent Claim
14 words
A composition of claim 14 wherein the compound is the neutral fumarate of 5-methoxy-3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole.
Claim 22
Dependent Claim
11 words
A composition of claim 14 wherein the compound is 3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 23
Dependent Claim
11 words
A composition of claim 14 wherein the compound is 3-(1-pentyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 24
Dependent Claim
11 words
A composition of claim 14 wherein the compound is 5-chloro-3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 25
Dependent Claim
11 words
A composition of claim 14 wherein the compound is 3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 26
Dependent Claim
11 words
A composition of claim 14 wherein the compound is 3-(1-isopropyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 27
Dependent Claim
11 words
A composition of claim 14 wherein the compound is 6-methoxy-3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 28
Dependent Claim
29 words
A method of treating psychic disorders in warm-blooded animals comprising administering to warm-blooded animals an amount of at least one compound of claim 1 sufficient to relieve psychic disorders.
Claim 29
Dependent Claim
57 words
A method of claim 27 wherein R' is selected from the group consisting of hydrogen and alkoxy of 1 to 3 carbon atoms and X' is alkyl of 1 to 6 carbon atoms with the proviso that when X' is methyl, at least one of R', R 1 and R 2 contain more than one carbon atom.
Claim 30
Dependent Claim
29 words
A method of claim 27 wherein R' is halogen, R 1 and R 2 are individually hydrogen or methyl and X' is alkyl of 2 to 6 carbon atoms.
Claim 31
Dependent Claim
26 words
A method of claim 27 wherein R' is 5-chloro, R 1 and R 2 are hydrogen and X' is alkyl of 2 to 6 carbon atoms.
Claim 32
Dependent Claim
31 words
A method of claim 27 wherein R' is hydrogen or methoxy, R 1 and R 2 are individually hydrogen or methyl and X' is alkyl of 2 to 6 carbon atoms.
Claim 33
Dependent Claim
28 words
A method of claim 27 wherein R' is hydrogen or 5-methoxy, R 1 and R 2 are hydrogen and X' is alkyl of 2 to 6 carbon atoms.
Claim 34
Dependent Claim
14 words
A method of claim 27 wherein the compound is the neutral fumarate of 5-methoxy-3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole.
Claim 35
Dependent Claim
11 words
A method of claim 27 wherein the compound is 3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 36
Dependent Claim
11 words
A method of claim 27 wherein the compound is 3-(1-pentyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 37
Dependent Claim
11 words
A method of claim 27 wherein the compound is 5-chloro-3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 38
Dependent Claim
11 words
A method of claim 27 wherein the compound is 3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 39
Dependent Claim
11 words
A method of claim 27 wherein the compound is 3-(1-isopropyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
Claim 40
Dependent Claim
11 words
A method of claim 27 wherein the compound is 6-methoxy-3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride.
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) | 1984-07-13 | 1985-01-12 | 1985-07-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-07-13 | 1989-01-12 | 1989-07-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-07-13 | 1993-01-12 | 1993-07-14 | $7700.00 | Window Closed / Lapsed |