US4996206A
Expired / Lapsed
US
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N-(pyrrolo[2,3-d]pyrimidin-3-ylacyl)-glutamic acid derivatives
Assignee: Princeton University
•
Filing: 1990-05-24
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Granted: 1991-02-26
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Expires: 2010-05-24
Abstract
Abstract N-(Acyl)glutamic acid derivatives in which the acyl group is substituted with 4-hydroxypyrrolo[2,3-d]pyrimidin-3-yl group are antineoplastic agents. A typical embodiment is N-[4-(2-{4-hydroxypyrrolo[2,3-d]pyrimidin-3-yl}ethyl)benzoyl]-L-glutamic acid.
Inventors
- 👤 Edward C. Taylor
- 👤 Dietmar G. Kuhnt
- 👤 Chuan Shih
- 👤 Gerald B. Grindey
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 17:34
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
90 words
A compound of the formula: ##STR16## in which: R 1 is -OH or -NH 2 ; R 3 is 1,4-phenylene or 1,3-phenylene unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl; thienediyl or furanediyl unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl; cyclohexadiyl; and alkanediyl of two to four carbon atoms; R 4 is hydrogen, methyl, or hydroxymethyl; and R 5 is hydrogen or alkyl of 1 to 6 carbon atoms; the configuration about the carbon atom designated * is S; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
90 words
A compound of the formula: ##STR16## in which: R 1 is -OH or -NH 2 ; R 3 is 1,4-phenylene or 1,3-phenylene unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl; thienediyl or furanediyl unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl; cyclohexadiyl; and alkanediyl of two to four carbon atoms; R 4 is hydrogen, methyl, or hydroxymethyl; and R 5 is hydrogen or alkyl of 1 to 6 carbon atoms; the configuration about the carbon atom designated * is S; and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
20 words
A compound according to claim 1 wherein R 1 is -OH; R 3 is 1,4-phenylene; and R 4 is hydrogen.
Claim 4
Dependent Claim
11 words
A compound according to claim 2 wherein R 5 is hydrogen.
Claim 5
Dependent Claim
11 words
A compound according to claim 2 wherein R 5 is methyl.
Claim 6
Dependent Claim
20 words
A compound according to claim 1 wherein R 1 is -OH; R 3 is 1,4-phenylene, and R 4 is hydroxymethyl.
Claim 7
Dependent Claim
11 words
A compound according to claim 5 wherein R 5 is hydrogen.
Claim 8
Dependent Claim
11 words
A compound according to claim 5 wherein R 5 is methyl.
Claim 9
Dependent Claim
20 words
A compound according to claim 1 wherein R 1 is -OH; R 3 is thienediyl, and R 4 is hydrogen.
Claim 10
Dependent Claim
11 words
A compound according to claim 8 wherein R 5 is hydrogen.
Claim 11
Dependent Claim
11 words
A compound according to claim 8 wherein R 5 is methyl.
Claim 12
Dependent Claim
10 words
The compound according to claim 1 which is N-{4-[2-(4-hydroxypyrrolo[2,3-d]pyrimidin-3-yl)ethyl]benzoyl}-L-glutamic acid.
Claim 13
Dependent Claim
10 words
The compound according to claim 1 which is N-{4-[2-(4-hydroxy-6-methylpyrrolo[2,3-d]pyrimidin-3-yl)ethyl]benzoyl}-L-glutamic acid.
Claim 14
Dependent Claim
32 words
The method of combatting 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 15
Dependent Claim
47 words
A pharmaceutical composition for combatting 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 16
Dependent Claim
115 words
A compound of the formula: ##STR17## in which: R 1 is -OH or -NH 2 ; R 2 ' is hydrogen, or a carboxy protecting group; R 3 is 1,4-phenylene or 1,3-phenylene unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl, thienediyl or furanediyl unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl, cyclohexadiyl, or alkanediyl of two to four carbon atoms; R 4 ' is hydrogen, methyl, hydroxymethyl, or hydroxymethyl substituted with a hydroxy protecting group; and R 5 40 is hydrogen or alkyl of 1 to 6 carbon atoms, at least one of R 2 ' and R 4 ', being a carboxy protecting group or a hydroxy protecting group, respectively.
Claim 17
Dependent Claim
115 words
A compound of the formula: ##STR17## in which: R 1 is -OH or -NH 2 ; R 2 ' is hydrogen, or a carboxy protecting group; R 3 is 1,4-phenylene or 1,3-phenylene unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl, thienediyl or furanediyl unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl, cyclohexadiyl, or alkanediyl of two to four carbon atoms; R 4 ' is hydrogen, methyl, hydroxymethyl, or hydroxymethyl substituted with a hydroxy protecting group; and R 5 40 is hydrogen or alkyl of 1 to 6 carbon atoms, at least one of R 2 ' and R 4 ', being a carboxy protecting group or a hydroxy protecting group, respectively.
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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) | 1994-02-25 | 1994-08-27 | 1995-02-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-02-25 | 1998-08-27 | 1999-02-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-02-25 | 2002-08-27 | 2003-02-26 | $7700.00 | Window Closed / Lapsed |