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US4831037A
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4 (3H)-oxo-5,6,7,8-tetrahydropyrido-(2,3-d)pyrimidine derivatives
Assignee: Princeton University
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Filing: 1987-04-20
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Granted: 1989-05-16
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Expires: 2007-04-20
Abstract
Abstract N-[4-(N'-[2-amino-4(3H)-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-ylmethyl]-N'-acylamino)benzoyl]-L-glutamic acid derivatives are antineoplastic agents. The compounds are prepared through acylation of the corresponding N'-amino compound or hydrolysis of a protected N'-acylamino compound. A typical embodiment is N-[4-(N'-[2-amino-4(3H)-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-ylmethyl]-N'-formylamino)benzoyl]-L-glutamic acid.
Inventors
- 👤 Edward C. Taylor
- 👤 George P. Beardsley
- 👤 James M. Hamby
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:53
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
143 words
A compound selected from the group consisting of: (i) 4(3H)-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidines of the formula: ##STR8## wherein R 2' and R 3' are hydrogen or the same or different carboxylic acid protecting group selected from the group consisting of straight or branched chain alkyl of 1 to 6 carbon atoms, unsubstituted or substituted with one or more phenyl, halo, or alkoxy groups, and silyl; R 4' is hydrogen or an amino protecting group selected from the group consisting of alkanoyl and alkoxycarbonyl of 2 to 6 carbon atoms, each of which is unsubstituted or substituted with halo, alkoxy or phenyl; R 5 is hydrogen or alkyl of 1 to 6 carbon atoms; and the configuration about the carbon atom designated * is L; and (ii) the tautomeric forms thereof at least one of R 2' , R 3' and R 4' being other than hydrogen.
Claim 2
Dependent Claim
143 words
A compound selected from the group consisting of: (i) 4(3H)-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidines of the formula: ##STR8## wherein R 2' and R 3' are hydrogen or the same or different carboxylic acid protecting group selected from the group consisting of straight or branched chain alkyl of 1 to 6 carbon atoms, unsubstituted or substituted with one or more phenyl, halo, or alkoxy groups, and silyl; R 4' is hydrogen or an amino protecting group selected from the group consisting of alkanoyl and alkoxycarbonyl of 2 to 6 carbon atoms, each of which is unsubstituted or substituted with halo, alkoxy or phenyl; R 5 is hydrogen or alkyl of 1 to 6 carbon atoms; and the configuration about the carbon atom designated * is L; and (ii) the tautomeric forms thereof at least one of R 2' , R 3' and R 4' being other than hydrogen.
Claim 3
Dependent Claim
37 words
A compound according to claim 1 wherein R 5 is hydrogen, each of R 2' and R 3' is alkyl of 1 to 6 carbon atoms and R 4' is alkanoyl of 2 to 6 carbon atoms.
Claim 4
Dependent Claim
22 words
The compound according to claim 2 in which each of R 2' and R 3' is ethyl, and R 4' is acetyl.
Claim 5
Dependent Claim
22 words
The compound according to claim 2 in which each of R 2' and R 3' is ethyl, and R 4' is pivaloyl.
Claim 6
Dependent Claim
37 words
A compound according to claim 1 wherein R 5 is methyl, each of R 2' and R 3' is alkyl of 1 to 6 carbon atoms and R 4' is alkanoyl of 2 to 6 carbon atoms.
Claim 7
Dependent Claim
22 words
The compound according to claim 5 in which each of R 2' and R 3' is ethyl, and R 4' is acetyl.
Claim 8
Dependent Claim
22 words
The compound according to claim 5 in which each of R 2' and R 3' is ehtyl, and R 4' is pivaloyl.
Claim 9
Dependent Claim
49 words
A compound of the formula: ##STR9## wherein: R 5 is hydrogen or alkyl of 1 to 6 carbon atoms; the configuration about the carbon atom designated * is L, and the tautomeric forms thereof and the pharmaceutically acceptable alkali metal, alkaline earth metal, ammonium, and substituted amonium salts thereof.
Claim 10
Dependent Claim
49 words
A compound of the formula: ##STR9## wherein: R 5 is hydrogen or alkyl of 1 to 6 carbon atoms; the configuration about the carbon atom designated * is L, and the tautomeric forms thereof and the pharmaceutically acceptable alkali metal, alkaline earth metal, ammonium, and substituted amonium salts thereof.
Claim 11
Dependent Claim
35 words
A compound according to claim 8 selected from the group consisting (i) of N-[4-(N'-[2amino-4(3H)-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl-methyl]-N'-formylamino)benzoyl]-L-glutamic acid, (ii) N-[4-(N'-[2-amino-4(3H)-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-ylmethyl]-N'-acetylamino)benzoyl]-L-glutamic acid, 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-(N'-[2-amino-4(3H)-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-ylmethyl]-N'-formylamino)benzoyl]-L-glutamic acid.
Claim 13
Dependent Claim
10 words
The compound according to claim 9 which is N-[4-(N'-[2-amino-4(3H)-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-ylmethyl]-N'-acetylamino)benzoyl]-L-glutamic acid.
Claim 14
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 10.
Claim 15
Dependent Claim
47 words
A pharmaceutical composition for combating neoplastic growth in a mammal which comprises an amount of a compound according to claim 10 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 16
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 11.
Claim 17
Dependent Claim
47 words
A pharmaceutical composition for combating neoplastic growth in a mammal which comprises an amount of a compound according to claim 11 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.
References Cited (Backward Citations)
US4684653A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-05-15 | 1992-11-14 | 1993-05-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-05-15 | 1996-11-14 | 1997-05-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-05-15 | 2000-11-14 | 2001-05-16 | $7700.00 | Window Closed / Lapsed |