US4254284A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for preparing 4-aminohex-5-ynoic acid
Assignee: Merrell Toraude et Cie
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Filing: 1980-01-14
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Granted: 1981-03-03
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Expires: 2000-01-14
Abstract
Abstract Novel compounds of the following general formula are useful in the preparation of 4-aminohex-5-enoic acid and 4-aminohex-5-ynoic acid which are useful pharmacological agents: ##STR1## wherein R 1 is hydroxy, amino, or tert-butoxy.
Inventors
- 👤 Maurice W. Gittos
- 👤 Gerard J. Letertre
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 22:36
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24; C07D207/26; C07D207/273; C07D207/277; C07D319/00; C07D319/04; C07D319/08
Claims Analysis
Total Claims: 2
Claim 1
Independent Claim
154 words
A process for the preparation of 4-aminohex-5-ynoic acid or salt thereof which comprises treating a pyrrolidone compound of the formula ##STR11## wherein R 1 is hydroxy, amino, or tertiary-butoxy with a strong base in a lower alcohol solvent at a temperature of about 20° C. to the reflux temperature of the solvent for about 6 to 24 hours when R 1 is amino, decarboxylating the 3-carboxy derivative or its tertiary butyl ester to give 5-vinyl-2-pyrrolidone which is treated in a chlorinated hydrocarbon solvent or acetic acid with an equivalent amount of bromine at about 0° to 35° C. with stirring for about 4 to 24 hours, treating the thus formed dibromo intermediate in an ether solvent or liquid ammonia with a strong base for about 1 to 40 hours at about -80° to 125° C. and quenching with water followed by acid hydrolysis, and when the free base is desired subsequent treatment with base.
Claim 2
Dependent Claim
154 words
A process for the preparation of 4-aminohex-5-ynoic acid or salt thereof which comprises treating a pyrrolidone compound of the formula ##STR11## wherein R 1 is hydroxy, amino, or tertiary-butoxy with a strong base in a lower alcohol solvent at a temperature of about 20° C. to the reflux temperature of the solvent for about 6 to 24 hours when R 1 is amino, decarboxylating the 3-carboxy derivative or its tertiary butyl ester to give 5-vinyl-2-pyrrolidone which is treated in a chlorinated hydrocarbon solvent or acetic acid with an equivalent amount of bromine at about 0° to 35° C. with stirring for about 4 to 24 hours, treating the thus formed dibromo intermediate in an ether solvent or liquid ammonia with a strong base for about 1 to 40 hours at about -80° to 125° C. and quenching with water followed by acid hydrolysis, and when the free base is desired subsequent treatment with base.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-03-02 | 1984-09-01 | 1985-03-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-03-02 | 1988-09-01 | 1989-03-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-03-02 | 1992-09-01 | 1993-03-03 | $7700.00 | Window Closed / Lapsed |