US4703036A
Expired / Lapsed
US
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Peptide-aldehydes, process for the preparation thereof and pharmaceutical compositions containing the same
Assignee: Teva Hungary Pharmaceutical Marketing PLC
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Filing: 1985-12-20
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Granted: 1987-10-27
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Expires: 2005-12-20
Abstract
Abstract The invention relates to new peptide-aldehydes and a process for the preparation thereof, furthermore to pharmaceutical compositions containing the same. According to a feature of the present invention there are provided new peptide-aldehyde derivatives corresponding to the general formula (I) <IMAGE> (I) wherein R1 represents hydrogen or C1-6 alkyl group, R2 stands for C1-6 alkyl group, furthermore R1 and R2 are linked to the amino group of the Xxx alpha-amino acid, Xxx represents a D-phenylalanine residue or a D-alpha-amino acid group having in the side chain a C1-4 alkyl group, Pro stands for L-proline residue, Yyy stands for L-, D- or DL-arginine residue and A represents an acid residue. The new peptide-aldehyde derivatives of the invention possess valuable anticoagulant activity.
Inventors
- 👤 Sandor Bajusz
- 👤 Erzsbet Szell nee Hasenohrl
- 👤 Daniel Bagdy
- 👤 Eva Barabas
- 👤 Mariann Dioszegi
- 👤 Zsuzsa Fittler
- 👤 Ferencz Jozsa
- 👤 Gyula Horvath
- 👤 Eva Tomori nee Jozst
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 11:25
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06008; C07K5/06078; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
72 words
A peptide-aldehyde derivative having the formula (I) ##STR3## wherein R 1 represents hydrogen or C 1-6 alkyl group, R 2 stands for C 1-6 alkyl group, furthermore R 1 and R 2 are linked to the amino group of the Xxx alpha amino acid, Xxx represents a D-phenylalanine residue or a D-alloisoleucine residue, Pro stands for L-proline residue, Yyy stands for L-, D- or DL-arginine residue, and A represents an acid residue.
Claim 2
Dependent Claim
72 words
A peptide-aldehyde derivative having the formula (I) ##STR3## wherein R 1 represents hydrogen or C 1-6 alkyl group, R 2 stands for C 1-6 alkyl group, furthermore R 1 and R 2 are linked to the amino group of the Xxx alpha amino acid, Xxx represents a D-phenylalanine residue or a D-alloisoleucine residue, Pro stands for L-proline residue, Yyy stands for L-, D- or DL-arginine residue, and A represents an acid residue.
Claim 3
Dependent Claim
18 words
A compound according to claim 1, wherein R 1 is hydrogen and R 2 is a methyl group.
Claim 4
Dependent Claim
15 words
A compound according to claim 1, wherein R 1 and R 2 are methyl groups.
Claim 5
Dependent Claim
15 words
A compound of the formula (I) of claim 1, wherein Xxx is a D-phenylalanine residue.
Claim 6
Dependent Claim
15 words
A compound of the formula (I) of claim 1, wherein Yyy is an L-arginine residue.
Claim 7
Dependent Claim
29 words
A compound of formula (I) as defined in claim 1 selected from the group consisting of N-methyl-D-phenylalanyl-L-prolyl-L-arginine-aldehyde sulfate, N,N-dimethyl-D-phenylalanyl-L-prolyl-L-arginine-aldehyde sulfate, N-ethyl-D-phenylalanyl-L-prolyl-L-arginine-aldehyde sulfate, N-isobutyl-D-phenylalanyl-L-prolyl-L-arginine-aldehyde sulfate, N-methyl-D-alloisoleucyl-L-prolyl-L-arginine-aldehyde sulfate and N-n-hexyl-D-phenylalanyl-L-prolyl-L-arginine-aldehyde sulfate.
Claim 8
Dependent Claim
31 words
A pharmaceutical composition having anticoagulant activity, which comprises as active ingredient at least one compound of formula (I) as defined in claim 1 in admixture with one or more pharmaceutical carriers.
Claim 9
Dependent Claim
37 words
A method of inhibiting blood coagulation in a mammalian subject which comprises the step of administering to said mammalian subject a therapeutically effective amount of the aldehyde salt of the Formula (I) as defined in claim 1.
Claim 10
Dependent Claim
25 words
The method of inhibiting blood coagulation defined in claim 8 wherein the aldehyde salt of the Formula (I) is orally administered to the mammalian subject.
Claim 11
Dependent Claim
25 words
The method of inhibiting blood coagulation defined in claim 8 wherein the aldehyde salt of the Formula (I) is intravenously administered to the mammalian subject.
References Cited (Backward Citations)
US4399065A
Cited
US4478745A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-10-26 | 1991-04-27 | 1991-10-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-10-26 | 1995-04-27 | 1995-10-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-10-26 | 1999-04-27 | 1999-10-27 | $7700.00 | Window Closed / Lapsed |