US3932431A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Certain 2-[α(2-pyridyl)-benzyl] imidazolines and derivatives thereof
Assignee: Merck Sharp & Dohme LLC
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Filing: 1973-11-05
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Granted: 1976-01-13
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Expires: 1993-11-05
Abstract
Abstract The present 2-substituted imidazolines and 2-substituted-3,4,5,6-tetrahydropyrimidines possess valuable anti-depressant and anti-inflammatory properties. The compounds are prepared by the condensation of an appropriately substituted nitrile with a diamine. For example, condensation of 2-pyridylbenzyl cyanide with 1,2-ethylene diamine or with 1,3-propylene diamine produces a 2-(2-pyridylbenzyl) imidazoline or a 2-(2-pyridylbenzyl)-3,4,5,6-tetrahydropyrimidine.
Inventors
- 👤 Lewis A. Walter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 18:05
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/14; C07D401/02; C07D401/06; C07D403/00; C07D403/02; C07D403/06; C07D409/00; C07D409/02; C07D409/06
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
196 words
A compound selected from the group consisting of cyclic amidines of the structural formula: ##SPC2## and the pharmaceutically acceptable acid addition salts thereof, wherein n is an integer of the group consisting of zero and one; A is a member of the group consisting of --C=C, --C=N, and --S--; wherein A together with the ring atoms to which it is attached represents a heterocycle of the group consisting of pyridyl, pyrimidinyl, and thiazoyl each of Z 1 , Z 2 and Z 3 is a member of the group consisting of hydrogen, lower alkyl, and trifluoromethyl, lower alkoxy and halogen and Z 4 is a member of the group consisting of hydrogen, lower alkyl, trifluoromethyl, lower alkoxy, halogen and diloweralkylamino; ##EQU7## represents a member of the group consisting of phenyl, thienyl and pyridyl; Y represents a member of the group consisting of hydroxy, lower alkoxy and lower alkanoyloxy containing 2 to 6 carbon atoms; R 1 represents a member of the group consisting of hydrogen, lower alkyl, aminoloweralkyl, hydroxyloweralkyl, benzyl and phenethyl; each of R 2 , R 3 , R 4 and R 5 are members of the group consisting of hydrogen and lower alkyl.
Claim 2
Dependent Claim
196 words
A compound selected from the group consisting of cyclic amidines of the structural formula: ##SPC2## and the pharmaceutically acceptable acid addition salts thereof, wherein n is an integer of the group consisting of zero and one; A is a member of the group consisting of --C=C, --C=N, and --S--; wherein A together with the ring atoms to which it is attached represents a heterocycle of the group consisting of pyridyl, pyrimidinyl, and thiazoyl each of Z 1 , Z 2 and Z 3 is a member of the group consisting of hydrogen, lower alkyl, and trifluoromethyl, lower alkoxy and halogen and Z 4 is a member of the group consisting of hydrogen, lower alkyl, trifluoromethyl, lower alkoxy, halogen and diloweralkylamino; ##EQU7## represents a member of the group consisting of phenyl, thienyl and pyridyl; Y represents a member of the group consisting of hydroxy, lower alkoxy and lower alkanoyloxy containing 2 to 6 carbon atoms; R 1 represents a member of the group consisting of hydrogen, lower alkyl, aminoloweralkyl, hydroxyloweralkyl, benzyl and phenethyl; each of R 2 , R 3 , R 4 and R 5 are members of the group consisting of hydrogen and lower alkyl.
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein Y is hydroxy.
Claim 4
Dependent Claim
9 words
A compound of claim 1 wherein n is zero.
Claim 5
Dependent Claim
9 words
A compound of claim 1 wherein Y is phenyl.
Claim 6
Dependent Claim
9 words
A compound of claim 2 wherein A is pyridyl.
Claim 7
Dependent Claim
9 words
A compound of claim 3 wherein A is pyridyl.
Claim 8
Dependent Claim
9 words
A compound of claim 4 wherein A is pyridyl.
Claim 9
Dependent Claim
9 words
A compound of claim 5 wherein n is zero.
Claim 10
Dependent Claim
9 words
A compound of claim 8 wherein ##EQU8## is phenyl.
Claim 11
Dependent Claim
9 words
A compound of claim 8 wherein ##EQU9## is pyridyl.
Claim 12
Dependent Claim
33 words
A compound of claim 9 wherein all of R 2 , R 3 , R 4 , R 5 , Z 1 , Z 2 , Z 3 and Z 4 are hydrogen.
Claim 13
Dependent Claim
10 words
A compound of claim 11 wherein R 1 is hydrogen.
Claim 14
Dependent Claim
11 words
A compound of claim 11 wherein R 1 is lower alkyl.
Claim 15
Dependent Claim
10 words
A compound of claim 13 wherein R 1 is methyl.
Claim 16
Dependent Claim
10 words
A compound of claim 2, said compound being 2-](2-pyridyl)-hydroxybenzyl] imidazoline.
References Cited (Backward Citations)
US2656358A
Cited
US3770737A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-12 | 1979-07-14 | 1980-01-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-12 | 1983-07-14 | 1984-01-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-12 | 1987-07-14 | 1988-01-13 | $7700.00 | Window Closed / Lapsed |