US4316889A
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Novel peptidyl-arginine aldehyde derivatives and process for the preparation thereof
Assignee: Teva Hungary Pharmaceutical Marketing PLC
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Filing: 1979-12-28
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Granted: 1982-02-23
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Expires: 1999-12-28
Abstract
Abstract Novel peptidyl-arginine aldehyde derivatives and their salts of formula I, <IMAGE> wherein X represents a hydrogen atom, benzoyl or tert-butyloxycarbonyl group, and Y is a D-phenylalanine, beta -phenyl-D-lactic acid or D-allo-isoleucine moiety, are prepared from peptidyl-arginine aldehydes protected by an urethane type protecting group on their N- or O-terminal and/or a guanidino group, by removing the protecting group in a mixture of lower alkanols and water by means of hydrogenolysis, and eventually converting the product formed into a salt. The compounds of formula I possess valuable antithrombin activity.
Inventors
- 👤 Sandor Bajusz
- 👤 Erzsebet Szell nee Hasenohrl
- 👤 Eva Barabas
- 👤 Daniel Bagdy
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 19:15
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/08; C07K5/0802; C07K5/0812; A; A61; A61P; A61P3/00; A61P43/00; A61P7/00; A61P7/02; C07K5/06; C07K5/06008; C07K5/06078; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
33 words
A peptidyl-arginine aldehyde derivative of the formula I or Ia ##STR3## wherein X is hydrogen, benzoyl or tert-butyloxycarbonyl, and Y is D-phenylalanine, β-phenyl-D-lactic acid or D-allo-isoleucine residue or a pharmaceutically effective salt thereof.
Claim 2
Dependent Claim
33 words
A peptidyl-arginine aldehyde derivative of the formula I or Ia ##STR3## wherein X is hydrogen, benzoyl or tert-butyloxycarbonyl, and Y is D-phenylalanine, β-phenyl-D-lactic acid or D-allo-isoleucine residue or a pharmaceutically effective salt thereof.
Claim 3
Dependent Claim
34 words
The compound defined in claim 1, selected from the group consisting of D-phenylalanyl-L-prolyl-N G -carboxyl-L-arginine aldehyde, D-phenylalanyl-L-prolyl-N G -carboxy-L-arginine aldehyde hemihydrochloride, tert-butyloxycarbonyl-D-phenylalanyl-L-prolyl-N G -carboxyl-L-arginine aldehyde, benzoyl-D-allo-isoleucyl-L-prolyl-N G -carboxy-L-arginine aldehyde, and β-phenyl-D-lactyl-L-prolyl-N G -carboxy-L-arginine aldehyde.
Claim 4
Dependent Claim
34 words
A pharmaceutical composition for inhibiting the thrombin-fibrinogen reaction containing an effective amount of a compound as defined in claim 1 as the active agent in association with a pharmaceutically acceptable solid or liquid carrier.
Claim 5
Independent Claim
54 words
A method of inhibiting the thrombin-fibrinogen reaction in a system susceptible thereto which comprises administering to the system an effective amount of a compound of the formula I or Ia ##STR4## wherein X is hydrogen, benzoyl or tert-butyloxycarbonyl, and Y is a D-phenylalanine, β-phenyl-D-lactic acid or D-allo-isoleucine residue or a pharmaceutically effective salt thereof.
Claim 6
Independent Claim
54 words
A method of inhibiting the thrombin-fibrinogen reaction in a system susceptible thereto which comprises administering to the system an effective amount of a compound of the formula I or Ia ##STR4## wherein X is hydrogen, benzoyl or tert-butyloxycarbonyl, and Y is a D-phenylalanine, β-phenyl-D-lactic acid or D-allo-isoleucine residue or a pharmaceutically effective salt thereof.
References Cited (Backward Citations)
JPS4941418A
Cited
HU169870B
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-02-22 | 1985-08-24 | 1986-02-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-02-22 | 1989-08-24 | 1990-02-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-02-22 | 1993-08-24 | 1994-02-23 | $7700.00 | Window Closed / Lapsed |