US4299821A
Expired / Lapsed
US
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Tripeptides acting on the central nervous system and a process for the preparation thereof
Assignee: Richter Gedeon Vegyeszeti Gyar Nyrt
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Filing: 1980-06-27
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Granted: 1981-11-10
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Expires: 2000-06-27
Abstract
Abstract The invention relates to new peptide derivatives which act on the central nervous system and correspond to the general formula (I), Glp-X-Y-NH-A (I) wherein X is L-norleucyl, L-leucyl, L-norvalyl, D-leucyl, L-prolyl, L-2-aminobutyryl, L-valyl, L-threonyl, L-isoleucyl, L-2-aminodecanoyl, L-cyclohexylalanyl or L-tert.-butyl-seryl group and Y is L-prolyl group, or X is L-histidyl group and Y is L-homoprolyl or D-pipecolyl group, furthermore A is hydrogen, a C1-10 alkyl group or a C1-3 alkyl group having a dimethylamino substituent, with the proviso that if X is L-leucyl group, A is other than hydrogen, and pharmaceutically acceptable complexes thereof. These compounds are prepared by methods commonly applied in the peptide chemistry.
Inventors
- 👤 Lajos Kisfaludy
- 👤 Tamas Szirtes
- 👤 Lajos Balaspiri
- 👤 Eva Palosi
- 👤 Laszlo Szporny
- 👤 Adam Sarkadi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 08:58
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06008; C07K5/06017; C07K5/06034; A; A61; A61P; A61P25/00; C07K5/06043; C07K5/06104; C07K5/08; C07K5/0821; C07K5/0825
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
118 words
A peptide derivative of the general formula Glp-X-Y-NH-A, wherein X is L-norleucyl, L-leucyl, D-leucyl, L-isoleucyl, L-norvalyl, L-valyl, L-prolyl, L-threonyl, L-2-aminobutyryl, L-2-aminodecanoyl, L-cyclohexylalanyl, O-tert.-butyl-L-seryl or L-histidyl group, Y is a L-prolyl, L-homoprolyl or D-pipecolyl group, and A is hydrogen, alkyl of 1 to 10 carbon atoms or alkyl of 1 to 3 carbon atoms substituted with a dimethylamino group, with the proviso that when X is L-histidyl, then Y is not L-prolyl, when X is L-norleucyl, L-leucyl, D-leucyl, L-isoleucyl, L-norvalyl, L-valyl, L-prolyl, L-threonyl, L-2-aminobutyryl, L-2-aminodecanoyl, L-cyclohexylalanyl or O-tert.-butyl-L-seryl, then Y is not L-homoprolyl or D-pipecolyl and when X is L-leucyl, D-leucyl, L-norleucyl, L-isoleucyl, L-norvalyl or L-valyl, then A is not hydrogen, or a pharmaceutically acceptable salt or complex thereof.
Claim 2
Dependent Claim
118 words
A peptide derivative of the general formula Glp-X-Y-NH-A, wherein X is L-norleucyl, L-leucyl, D-leucyl, L-isoleucyl, L-norvalyl, L-valyl, L-prolyl, L-threonyl, L-2-aminobutyryl, L-2-aminodecanoyl, L-cyclohexylalanyl, O-tert.-butyl-L-seryl or L-histidyl group, Y is a L-prolyl, L-homoprolyl or D-pipecolyl group, and A is hydrogen, alkyl of 1 to 10 carbon atoms or alkyl of 1 to 3 carbon atoms substituted with a dimethylamino group, with the proviso that when X is L-histidyl, then Y is not L-prolyl, when X is L-norleucyl, L-leucyl, D-leucyl, L-isoleucyl, L-norvalyl, L-valyl, L-prolyl, L-threonyl, L-2-aminobutyryl, L-2-aminodecanoyl, L-cyclohexylalanyl or O-tert.-butyl-L-seryl, then Y is not L-homoprolyl or D-pipecolyl and when X is L-leucyl, D-leucyl, L-norleucyl, L-isoleucyl, L-norvalyl or L-valyl, then A is not hydrogen, or a pharmaceutically acceptable salt or complex thereof.
Claim 3
Dependent Claim
1 words
L-Pyroglutamyl-L-prolyl-L-prolinamide.
Claim 4
Dependent Claim
1 words
L-Pyroglutamyl-L-prolyl-L-prolinamide.
Claim 5
Dependent Claim
2 words
L-Pyroglutamyl-L-leucyl-L-proline ethylamide.
Claim 6
Dependent Claim
2 words
L-Pyroglutamyl-L-leucyl-L-proline ethylamide.
Claim 7
Dependent Claim
1 words
L-Pyroglutamyl-L-α-aminobutyryl-L-prolinamide.
Claim 8
Dependent Claim
1 words
L-Pyroglutamyl-L-α-aminobutyryl-L-prolinamide.
Claim 9
Dependent Claim
159 words
A pharmaceutical composition for use in (a) decreasing the duration of sleeping caused by barbituates and alcohol and/or (b) suppressing hypothermy provoked by various drugs and/or (c) increasing locomotive activity and/or (d) inhibiting catalepsy provoked by Haloperidol comprising an effective amount of an active ingredient comprising at least one compound of the formula Glp-X-Y-NH-A, wherein X is L-norleucyl, L-leucyl, D-leucyl, L-isoleucyl, L-norvalyl, L-valyl, L-prolyl, L-threonyl, 2-aminobutyryl, L-2-aminodecanoyl, L-cyclohexylalanyl, O-tert.-butyl-L-seryl or L-histidyl, Y is L-prolyl, L-homoprolyl or D-pipecolyl, and A is hydrogen, alkyl of 1 to 10 carbon atoms or alkyl of 1 to 3 carbon atoms having a dimethylamino substituent, with the proviso that when X is L-histidyl, then Y is not L-prolyl, when X is L-leucyl, then A is not hydrogen and when X is L-norleucyl, L-leucyl, D-leucyl, L-norvalyl, L-valyl, L-prolyl, L-threonyl, L-isoleucyl, L-2-aminobutyryl, L-2-aminodecanoyl, L-cyclohexylalanyl, or L-tert.-butyl-seryl, Y is not L-homoprolyl or D-pipecolyl, or a pharmaceutically acceptable salt or complex thereof and a pharmaceutical carrier or diluent.
Claim 10
Dependent Claim
159 words
A pharmaceutical composition for use in (a) decreasing the duration of sleeping caused by barbituates and alcohol and/or (b) suppressing hypothermy provoked by various drugs and/or (c) increasing locomotive activity and/or (d) inhibiting catalepsy provoked by Haloperidol comprising an effective amount of an active ingredient comprising at least one compound of the formula Glp-X-Y-NH-A, wherein X is L-norleucyl, L-leucyl, D-leucyl, L-isoleucyl, L-norvalyl, L-valyl, L-prolyl, L-threonyl, 2-aminobutyryl, L-2-aminodecanoyl, L-cyclohexylalanyl, O-tert.-butyl-L-seryl or L-histidyl, Y is L-prolyl, L-homoprolyl or D-pipecolyl, and A is hydrogen, alkyl of 1 to 10 carbon atoms or alkyl of 1 to 3 carbon atoms having a dimethylamino substituent, with the proviso that when X is L-histidyl, then Y is not L-prolyl, when X is L-leucyl, then A is not hydrogen and when X is L-norleucyl, L-leucyl, D-leucyl, L-norvalyl, L-valyl, L-prolyl, L-threonyl, L-isoleucyl, L-2-aminobutyryl, L-2-aminodecanoyl, L-cyclohexylalanyl, or L-tert.-butyl-seryl, Y is not L-homoprolyl or D-pipecolyl, or a pharmaceutically acceptable salt or complex thereof and a pharmaceutical carrier or diluent.
References Cited (Backward Citations)
US3959248A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-11-09 | 1985-05-11 | 1985-11-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-11-09 | 1989-05-11 | 1989-11-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-11-09 | 1993-05-11 | 1993-11-10 | $7700.00 | Window Closed / Lapsed |