Patent US4456594A successfully refreshed from Google Patents.
US4456594A
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N-Carboxyalkylproline-containing tripeptides
Assignee: SmithKline Beecham Corp
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Filing: 1982-10-21
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Granted: 1984-06-26
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Expires: 2002-10-21
Abstract
Abstract Certain N-carboxyalkyl prolyl-containing tripeptides have been prepared and found to improve kidney function. A species of the group of new compounds is N-(2-carboxyethyl)-L-prolyl-L-alanyl-L-proline which has diuretic activity and increases renal blood flow. The compounds are prepared by chemical reactions which couple an amino acid with a dipeptide.
Inventors
- 👤 Francis R. Pfeiffer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 17:59
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/08; C07K5/0821; C07K5/0823
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
130 words
A chemical compound of the structural formula: ##STR5## in which: R is carboxy, sulfo or phosphono; alk is a straight or branched alkylene chain of 1-5 carbons which is not ethylidene; X is O or H,H; Y is H or, when X is H,H, OH; is an optional carbon-carbon bond, when X is H,H and Y is H; n is an integer of from 0-3 inclusive; and A is an amino acid residue derived from D- or L-Ala, D- or L-Phe, D- or L-β-methyl-β-Ala, D- or L-phenyl-Gly, D- or L-β-phenyl-β-Ala, D- or L-β-thienyl-Gly, D- or L-β-Ala, γ-aminobutyric acid; D- or L-2-aminobutyric acid, D- or L-nor-Val, D- or L-Leu, 3-amino-3-methyl butyric acid, 2-methyl-Ala or a N-methyl derivative of said residues; or a pharmaceutically acceptable salt or prodrug derivative of said compound.
Claim 2
Dependent Claim
130 words
A chemical compound of the structural formula: ##STR5## in which: R is carboxy, sulfo or phosphono; alk is a straight or branched alkylene chain of 1-5 carbons which is not ethylidene; X is O or H,H; Y is H or, when X is H,H, OH; is an optional carbon-carbon bond, when X is H,H and Y is H; n is an integer of from 0-3 inclusive; and A is an amino acid residue derived from D- or L-Ala, D- or L-Phe, D- or L-β-methyl-β-Ala, D- or L-phenyl-Gly, D- or L-β-phenyl-β-Ala, D- or L-β-thienyl-Gly, D- or L-β-Ala, γ-aminobutyric acid; D- or L-2-aminobutyric acid, D- or L-nor-Val, D- or L-Leu, 3-amino-3-methyl butyric acid, 2-methyl-Ala or a N-methyl derivative of said residues; or a pharmaceutically acceptable salt or prodrug derivative of said compound.
Claim 3
Dependent Claim
16 words
The compound of claim 1 in which the configuration of the amino acid units is L.
Claim 4
Dependent Claim
20 words
The compound of claim 2 in which R is carboxy, X is H,H, Y is hydrogen and n is O.
Claim 5
Dependent Claim
11 words
The compound of claim 3 in which A is a β-Ala.
Claim 6
Dependent Claim
13 words
The compound of claim 1 being N-(2-carboxymethyl)-L-prolyl-β-alanyl-L-proline of a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
7 words
The compound of claim 1 being N-(2-carboxymethyl)-L-prolyl-β-alanyl-L-proline.
Claim 8
Dependent Claim
13 words
The compound of claim 1 being N-(2-carboxyethyl)-L-prolyl-L-alanyl-L-proline or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
13 words
The compound of claim 1 being N-carboxymethyl-L-prolyl-L-phenylalanyl-L-proline or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
13 words
The compound of claim 1 being N-carboxymethyl-L-prolyl-D,L-β-methyl-β-alanyl-L-proline or a pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim
13 words
The compound of claim 1 being N-carboxymethyl-L-prolyl-D-β-methyl-β-alanyl-L-proline or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
34 words
A pharmaceutical composition effective for improving kidney function comprising a nontoxic, therapeutically effective quantity of a compound of claims 1, 2, 3, 4, 5, 6, 7, 8 or 9 combined with a carrier therefor.
Claim 13
Independent Claim
40 words
The method of improving kidney function in a subject in need thereof comprising administering orally or parenterally to said subject a nontoxic, therapeutically effective quantity of a compound of claims 1, 2, 3, 4, 5, 6, 7, 8 or 9.
References Cited (Backward Citations)
US4299769A
Cited
US4342689A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-06-26 | 1987-12-26 | 1988-06-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-06-26 | 1991-12-26 | 1992-06-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-06-26 | 1995-12-26 | 1996-06-26 | $7700.00 | Window Closed / Lapsed |