US4088668A
Expired / Lapsed
US
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Acetylene derivatives
Assignee: Merrell Toraude et Cie
•
Filing: 1977-07-01
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Granted: 1978-05-09
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Expires: 1997-07-01
Abstract
Abstract Novel compounds of the following general formula are useful pharmacologic agents and are useful as intermediates for the preparation of pharmacologically useful compounds. ##STR1## wherein R 1 is a straight or branched lower alkyl group having from 1 to 4 carbon atoms, R 2 is trialkylmethyl, phenyl, 1-adamantanyl or 2-furyl; R 3 is methoxy or ethoxy; and acid addition salts thereof.
Inventors
- 👤 Brian W. Metcalf
- 👤 Michel Jung
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 19:44
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/0812; A; A61; A61P; A61P25/00; A61P25/24; A61P25/26; A61P9/00; A61P9/12
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
54 words
A compound of the formula ##STR10## wherein R 1 is a straight or branched lower alkyl group having from 1 to 4 carbon atoms; R 2 is trialkylmethyl wherein the alkyl moiety has 1 or 2 carbon atoms, phenyl, 1-adamantanyl or 2-furyl; and R 3 is methoxy or ethoxy and acid addition salts thereof.
Claim 2
Dependent Claim
54 words
A compound of the formula ##STR10## wherein R 1 is a straight or branched lower alkyl group having from 1 to 4 carbon atoms; R 2 is trialkylmethyl wherein the alkyl moiety has 1 or 2 carbon atoms, phenyl, 1-adamantanyl or 2-furyl; and R 3 is methoxy or ethoxy and acid addition salts thereof.
Claim 3
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is methyl.
Claim 4
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is phenyl.
Claim 5
Dependent Claim
8 words
A compound of claim 1 which is: ##STR11##
Claim 6
Dependent Claim
125 words
A process for preparing a compound of claim 1 which comprises the steps of reacting propargylamine, wherein the acetylene function is protected by a trialkylsilyl group, with benzoyl chloride, pivalic acid chloride, 2,2-diethylbutyric acid chloride, 2-furoic acid chloride or 1-adamantanecarboxylic acid chloride at about 0° C in an appropriate solvent in the presence of an organic base after which the reaction mixture is allowed to warm to about 25° C for 1 hour, combining the resulting amide derivative with an appropriate alkylating reagent at about 25° C in an appropriate solvent after which the reaction mixture is refluxed for from 12 to 20 hours, cooling the reaction mixture to about 25° C after which an organic base is added and extracting the mixture with brine.
References Cited (Backward Citations)
US3946060A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-08 | 1981-11-07 | 1982-05-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-08 | 1985-11-07 | 1986-05-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-08 | 1989-11-07 | 1990-05-09 | $7700.00 | Window Closed / Lapsed |