US4033970A
Expired / Lapsed
US
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Various 1,5,10,11-tetrahydrobenzo [4,5]-cyclohepta [1,2-b]pyrazolo[4,3-e]pyridine derivatives
Assignee: ER Squibb and Sons LLC
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Filing: 1976-06-23
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Granted: 1977-07-05
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Expires: 1996-06-23
Abstract
Abstract Compounds of the formulas wherein R 1 is lower alkyl, phenyl, benzyl or phenethyl; R 2 is hydrogen, lower alkyl or phenyl; R is ##STR1## N IS AN INTEGER FROM 3 TO 6; R 3 and R 4 are each lower alkyl or R 3 and R 4 taken together with the N-atom form a heterocyclic ring of the formula ##STR2## wherein R 5 is hydrogen, lower alkyl, or lower alkoxy; and pharmaceutically acceptable acid addition salts thereof are disclosed. These compounds and their salts possess central nervous system activity and are useful as anti-anxiety agents.
Inventors
- 👤 Hans Hoehn
- 👤 Jack Bernstein
- 👤 Berthold Richard Vogt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 17:24
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
128 words
A compound of the formula: ##STR52## wherein R 1 is lower alkyl of 1 to 4 carbons, phenyl, benzyl or phenethyl; R 2 is hydrogen, lower alkyl of 1 to 4 carbons, or phenyl; R is ##STR53## wherein alkyl is straight or branched chain of 1 to 4 carbons and R 3 and R 4 are the same or different and each is lower alkyl of 1 to 4 carbons or R 3 and R 4 taken together with the N-atom form a heterocyclic ring selected from the group consisting of ##STR54## wherein R 5 is hydrogen, lower alkyl of 1 to 4 carbons, or lower alkoxy of 1 to 4 carbons; n is an integer from 3 to 6; and a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
128 words
A compound of the formula: ##STR52## wherein R 1 is lower alkyl of 1 to 4 carbons, phenyl, benzyl or phenethyl; R 2 is hydrogen, lower alkyl of 1 to 4 carbons, or phenyl; R is ##STR53## wherein alkyl is straight or branched chain of 1 to 4 carbons and R 3 and R 4 are the same or different and each is lower alkyl of 1 to 4 carbons or R 3 and R 4 taken together with the N-atom form a heterocyclic ring selected from the group consisting of ##STR54## wherein R 5 is hydrogen, lower alkyl of 1 to 4 carbons, or lower alkoxy of 1 to 4 carbons; n is an integer from 3 to 6; and a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
21 words
The compound of claim 1 wherein R is ##STR55## and alkyl is straight or branched chain of 1 to 4 carbons.
Claim 4
Dependent Claim
21 words
The compound of claim 2 wherein R 1 is lower alkyl of 1 to 4 carbons and R 2 is hydrogen.
Claim 5
Dependent Claim
14 words
The compound of claim 3 wherein R is ##STR56## and R 1 is ethyl.
Claim 6
Dependent Claim
8 words
The compound of claim 4, 1-ethyl-1,5,10,11-tetrahydro-5-(1-methyl-4-piperidinyl)benzo[4,5]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-5-ol, hydrochloride (1:2).
Claim 7
Dependent Claim
39 words
The compound of claim 1 wherein R is ##STR57## and n is an integer from 3 to 6 and R 3 and R 4 are the same or different and each is lower alkyl of 1 to 4 carbons.
Claim 8
Dependent Claim
40 words
The compound of claim 6 wherein R 1 is lower alkyl of 1 to 4 carbons, R 2 is hydrogen, n is 3 or 4, and R 3 and R 4 are the same and each is methyl or ethyl.
Claim 9
Dependent Claim
22 words
The compound of claim 7 wherein R 1 is ethyl, n is 3, and R 3 and R 4 are each methyl.
Claim 10
Dependent Claim
8 words
The compound of claim 8, 5-[3-(dimethylamino)propyl]-1-ethyl-1,5,10,11-tetrahydrobenzo[4,5]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-5-ol, hydrochloride (1:2).
Claim 11
Dependent Claim
38 words
The compound of claim 1 wherein R is ##STR58## and n is an integer from 3 to 6 and R 5 is hydrogen, lower alkyl of 1 to 4 carbons, or lower alkoxy of 1 to 4 carbons.
Claim 12
Dependent Claim
33 words
The compound of claim 10 wherein R 1 is lower alkyl of 1 to 4 carbons, R 2 is hydrogen, n is 3 or 4, and R 5 is hydrogen, methyl, or methoxy.
Claim 13
Dependent Claim
14 words
The compound of claim 11 wherein R 1 is ethyl and n is 3.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-04 | 1981-01-03 | 1981-07-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-04 | 1985-01-03 | 1985-07-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-04 | 1989-01-03 | 1989-07-05 | $7700.00 | Window Closed / Lapsed |