US4684653A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Pyrido(2,3-d)pyrimidine derivatives
Assignee: Princeton University
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Filing: 1986-03-03
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Granted: 1987-08-04
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Expires: 2006-03-03
Abstract
Abstract 2,4-Diamino- and 2-amino-4-hydroxy- derivatives of N-(4-[1-(pyrido[2,3-d]pyrimidin-6-yl)alk-2-yl]-benzoyl)-L-glutamic acids, and the corresponding 5,6,7,8-tetrahydro compounds are antineoplastic agents. The compounds are prepared by hydrolytic or hydrogenolytic removal of carboxylic acid protecting groups from the correspondingly protected glutamic acid derivatives. A typical embodiment is N-(4-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6- yl)ethyl]benzoyl)-L-glutamic acid.
Inventors
- 👤 Edward C. Taylor
- 👤 George P. Beardsley
- 👤 Peter J. Harrington
- 👤 Stephen R. Fletcher
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 20:35
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
55 words
A compound selected from the group consisting of: (i) 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidines of the formula: ##STR18## wherein: R 3 is hydrogen, methyl, or ethyl; and the configuration about the carbon atom designated * is L; (ii) the tautomeric forms thereof; and (iii) the pharmaceutically acceptable alkali metal, alkaline earth, non-toxic metal, ammonium, and substituted ammonium salts thereof.
Claim 2
Dependent Claim
55 words
A compound selected from the group consisting of: (i) 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidines of the formula: ##STR18## wherein: R 3 is hydrogen, methyl, or ethyl; and the configuration about the carbon atom designated * is L; (ii) the tautomeric forms thereof; and (iii) the pharmaceutically acceptable alkali metal, alkaline earth, non-toxic metal, ammonium, and substituted ammonium salts thereof.
Claim 3
Dependent Claim
10 words
The compound according to claim 1 which is N-(4-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl)-L-glutamic acid.
Claim 4
Dependent Claim
10 words
The compound according to claim 1 which is N-(4-[1-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)prop-2-yl]benzoyl)-L-glutamic acid.
Claim 5
Dependent Claim
10 words
The compound according to claim 1 which is N-(4-[1-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)but-2-yl]benzoyl)-L-glutamic acid.
Claim 6
Dependent Claim
32 words
The method of combating neoplastic growth in a mammal which comprises administering to the mammal in a single or multiple dose regimen an effective amount of a compound according to claim 1.
Claim 7
Dependent Claim
32 words
The method of combating neoplastic growth in a mammal which comprises administering to the mammal in a single or multiple dose regimen an effective amount of a compound according to claim 2.
Claim 8
Dependent Claim
47 words
A pharmaceutical composition for combating neoplastic growth in a mammal which comprises an amount of a compound according to claim 1 which upon administration to the mammal in a single or multiple dose regimen is effective to combat said growth, in combination with a pharmaceutically acceptable carrier.
Claim 9
Dependent Claim
47 words
A pharmaceutical composition for combating neoplastic growth in a mammal which comprises an amount of a compound according to claim 2 which upon administration to the mammal in a single or multiple dose regimen is effective to combat said growth, in combination with a pharmaceutically acceptable carrier.
Claim 10
Dependent Claim
55 words
A compound selected from the group consisting of: (i) 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidines of the formula: ##STR19## wherein: R 1 is hydrogen, methyl, or ethyl; and the configuration about the carbon atom designated * is L; (ii) the tautomeric forms thereof; and (iii) the pharmaceutically acceptable alkali metal, alkaline earth, non-toxic metal, ammonium, and substituted ammonium salts thereof.
Claim 11
Dependent Claim
55 words
A compound selected from the group consisting of: (i) 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidines of the formula: ##STR19## wherein: R 1 is hydrogen, methyl, or ethyl; and the configuration about the carbon atom designated * is L; (ii) the tautomeric forms thereof; and (iii) the pharmaceutically acceptable alkali metal, alkaline earth, non-toxic metal, ammonium, and substituted ammonium salts thereof.
Claim 12
Dependent Claim
10 words
The compound according to claim 9 which is N-(4-[2-(2,4-diamino-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl)-1-glutamic acid.
Claim 13
Dependent Claim
10 words
The compound according to claim 9 which is N-(4-[1-(2,4-diamino-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)prop-2-yl]benzoyl)-L-glutamic acid.
Claim 14
Dependent Claim
10 words
The compound according to claim 9 which is N-(4-[1-(2,4-diamino-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)but-2-yl]benzoyl)-L-glutamic acid.
Claim 15
Dependent Claim
68 words
A compound selected from the group consisting of: (i) 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidines of the formula: ##STR20## wherein R 1 is amino or hydroxy; R 3 is hydrogen, methyl, or ethyl; R 5 and R 6 are the same or different carboxylic acid protecting group; R 7 is hydrogen or an amino protecting group; and the configuration about the carbon atom designated * is L; and (ii) the tautomeric forms thereof.
Claim 16
Dependent Claim
68 words
A compound selected from the group consisting of: (i) 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidines of the formula: ##STR20## wherein R 1 is amino or hydroxy; R 3 is hydrogen, methyl, or ethyl; R 5 and R 6 are the same or different carboxylic acid protecting group; R 7 is hydrogen or an amino protecting group; and the configuration about the carbon atom designated * is L; and (ii) the tautomeric forms thereof.
Claim 17
Dependent Claim
10 words
The compound according to claim 13 which is diethyl N-(4-[2-(2-acetamido-4-hydroxy-5,6,7,8-tetrahdyropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl)-L-glutamate.
Claim 18
Dependent Claim
10 words
The compound according to claim 13 which is diethyl N-(4-[1-(2-acetamido-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)prop-2-yl]benzoyl)-L-glutamate.
Claim 19
Dependent Claim
10 words
The compound according to claim 13 which is diethyl N-(4-[2-(2,4-diamino-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl)-L-glutamate.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-08-03 | 1991-02-02 | 1991-08-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-08-03 | 1995-02-02 | 1995-08-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-08-03 | 1999-02-02 | 1999-08-04 | $7700.00 | Window Closed / Lapsed |