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US4065471A
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N-(4-Amino-2-butynyl)imides
Assignee: STWB Inc
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Filing: 1970-09-14
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Granted: 1977-12-27
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Expires: 1990-09-14
Abstract
Abstract N-(4-Amino-2-butynyl)imides are prepared from N-propargylimides, paraformaldehyde and the appropriate secondary amine. The compounds are useful as stimulants or depressants of the central nervous system.
Inventors
- 👤 William B. Dickinson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 14:05
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24; C07D207/26; C07D207/263; C07D207/27; C07D211/00; C07D211/04; C07D211/68; C07D211/72; C07D211/74; C07D211/76; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/81; C07D213/82; C07D263/00; C07D263/02; C07D263/08; C07D263/16; C07D263/18; C07D263/20; C07D263/22; C07D295/00; C07D295/04; C07D295/12; C07D295/125
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
53 words
A compound of the formula ##STR10## wherein A' is a member of the group consisting of divalent alkylene of from two to four carbon atoms and unsubstituted orthophenylene, and N═B is a basic tertiary amino radical selected from the group consisting of di(lower-alkyl)amino, N-lower-alkyl-N-lower-alkenylamino, di(lower-alkenyl)amino, N-lower-alkyl-N-cycloalkylamino, di(cycloalkyl)amino, N-(phenyl-lower-alkyl)-N-lower-alkylamino, pyrrolidino, piperidino, morpholino, and thiamorpholino.
Claim 2
Dependent Claim
53 words
A compound of the formula ##STR10## wherein A' is a member of the group consisting of divalent alkylene of from two to four carbon atoms and unsubstituted orthophenylene, and N═B is a basic tertiary amino radical selected from the group consisting of di(lower-alkyl)amino, N-lower-alkyl-N-lower-alkenylamino, di(lower-alkenyl)amino, N-lower-alkyl-N-cycloalkylamino, di(cycloalkyl)amino, N-(phenyl-lower-alkyl)-N-lower-alkylamino, pyrrolidino, piperidino, morpholino, and thiamorpholino.
Claim 3
Dependent Claim
14 words
N-(4-Pyrrolidino-2-butynyl)phthalimide, according to claim 1 wherein A' is unsubstituted ortho-phenylene and N═B is pyrrolidino.
Claim 4
Dependent Claim
13 words
N-(4-Pyrrolidino-2-butynyl)succinimide, according to claim 1 wherein A' is ethylene and N═B is pyrrolidino.
Claim 5
Dependent Claim
13 words
N-(5-Diisopropylamino-3-butynyl)succinimide, according to claim 1 wherein A' is ethylene and N═B is diisopropylamino.
Claim 6
Dependent Claim
128 words
A compound selected from the group consisting of ##STR11## and non-toxic addition salts thereof, wherein X is (CHR 5 ) p , p being an integer from 2 to 3, each R 5 being selected from the class consisting of hydrogen and alkyl, R 1 , R 2 , R 3 and R 4 are each hydrogen, m and n are the integer 1, Z is the divalent radical --C.tbd.C--, and Am is an amino group joined to the linking chain at the N atom, the amino group being selected from the class consisting of di-alkyl amino, di-alkenyl amino, (alkyl, alkenyl)amino, pyrrolidino, piperidino, methyl substituted pyrrolidino having 1 to 2 methyl groups, and morpholino, said alkyl and alkenyl groups when present having from 1 to 5 carbon atoms.
Claim 7
Dependent Claim
128 words
A compound selected from the group consisting of ##STR11## and non-toxic addition salts thereof, wherein X is (CHR 5 ) p , p being an integer from 2 to 3, each R 5 being selected from the class consisting of hydrogen and alkyl, R 1 , R 2 , R 3 and R 4 are each hydrogen, m and n are the integer 1, Z is the divalent radical --C.tbd.C--, and Am is an amino group joined to the linking chain at the N atom, the amino group being selected from the class consisting of di-alkyl amino, di-alkenyl amino, (alkyl, alkenyl)amino, pyrrolidino, piperidino, methyl substituted pyrrolidino having 1 to 2 methyl groups, and morpholino, said alkyl and alkenyl groups when present having from 1 to 5 carbon atoms.
Claim 8
Dependent Claim
23 words
A compound according to claim 5 wherein X is selected from the group consisting of --CH.sub.2 --CH.sub.2 -- and --CH.sub.2 --CH.sub.2 --CH.sub.2 --.
Claim 9
Dependent Claim
19 words
A compound according to claim 6 selected from the class consisting of N-(4-pyrrolidino-2-butynyl)-succinimide and pharmaceutically acceptable additional salts thereof.
Claim 10
Dependent Claim
146 words
A process for the preparation of the formula ##STR12## and non-toxic addition salts thereof wherein X is (CHR 5 ) p , p being an integer from 2 to 3, each R 5 being selected from the group consisting of hydrogen and alkyl, R 1 and R 2 are each hydrogen, m is the integer 1 and Am is an amino group joined to the linking chain at the nitrogen atom, the amino group being selected from the class consisting of di-alkyl amino, d-alkenyl amino, (alkyl, alkenyl) amino, pyrrolidino, piperidino, methyl substituted pyrrolidino having 1 to 2 methyl groups, and morpholino, and alkyl and alkenyl groups when present having from 1 to 5 carbon atoms, the system of reaction of propargyl imide of the formula ##STR13## with formaldehyde and an amine of the formula HAm, R 1 , R 2 and Am being as defined above.
Claim 11
Dependent Claim
146 words
A process for the preparation of the formula ##STR12## and non-toxic addition salts thereof wherein X is (CHR 5 ) p , p being an integer from 2 to 3, each R 5 being selected from the group consisting of hydrogen and alkyl, R 1 and R 2 are each hydrogen, m is the integer 1 and Am is an amino group joined to the linking chain at the nitrogen atom, the amino group being selected from the class consisting of di-alkyl amino, d-alkenyl amino, (alkyl, alkenyl) amino, pyrrolidino, piperidino, methyl substituted pyrrolidino having 1 to 2 methyl groups, and morpholino, and alkyl and alkenyl groups when present having from 1 to 5 carbon atoms, the system of reaction of propargyl imide of the formula ##STR13## with formaldehyde and an amine of the formula HAm, R 1 , R 2 and Am being as defined above.
References Cited (Backward Citations)
US3444171A
Cited
US3354178A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-12-26 | 1981-06-27 | 1981-12-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-26 | 1985-06-27 | 1985-12-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-26 | 1989-06-27 | 1989-12-27 | $7700.00 | Window Closed / Lapsed |