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US5028608A
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N-(6-Amino-(pyrrolo(2,3-d)pyrimidin-3-ylacyl) )-glutamic acid derivatives
Assignee: Princeton University
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Filing: 1990-05-24
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Granted: 1991-07-02
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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-{5-[2-(4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidin-3-yl)ethyl]thien-2-ylcarbonyl}-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
2026-10-24 15:53
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
64 words
A compound of the formula: ##STR16## in which: R 1 is --OH or --NH 2 ; R 3 is thienediyl or furanediyl unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl; cyclohexadiyl; and alkanediyl having 2 to 4 carbon atoms; R 4 is hydrogen, methyl, orhydroxymethyl; and the configuration about the carbon atom designated * is S; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
64 words
A compound of the formula: ##STR16## in which: R 1 is --OH or --NH 2 ; R 3 is thienediyl or furanediyl unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl; cyclohexadiyl; and alkanediyl having 2 to 4 carbon atoms; R 4 is hydrogen, methyl, orhydroxymethyl; and 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 thienediyl, and R 4 is hydrogen.
Claim 4
Dependent Claim
10 words
The compound according to claim 1 which is N-{5-[2-(4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidin-3-yl)-ethyl]thien-2-ylcarbonyl}-L-glutamic acid.
Claim 5
Dependent Claim
10 words
The compound according to claim 1 which is N-{4-[2-(4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidin-3-yl)-ethyl]thien-2-ylcarbonyl}-L-glutamic acid.
Claim 6
Dependent Claim
10 words
The compound according to claim 1 which is N-{5-[2-(4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidin-3-yl)ethyl]thien-3-ylcarbonyl}-L-glutamic acid.
Claim 7
Dependent Claim
10 words
The compound according to claim 1 which is N-[5-(4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidin-3-yl)pentanoyl]-L-glutamic acid.
Claim 8
Dependent Claim
10 words
The compound according to claim 1 which is N-[7-(4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidin-3-yl)heptanoyl]-L-glutamic acid.
Claim 9
Dependent Claim
10 words
The compound according to claim 1 which is N-[6-(4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidin-3-yl)hexanoyl]-L-glutamic acid
Claim 10
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 11
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 12
Dependent Claim
105 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 thienediyl or furanediyl unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl, cyclohexadiyl, or alkanediyl having 2 to 4 carbon atoms; R 4' is hydrogen, methyl, hydroxymethyl, or hydroxymethyl substituted with a hydroxy protecting group; and R 5' is amino or amino substituted with an amino protecting group, at least one of R 2' , R 4' , and R 5 being a carboxy protecting group, a hydroxy protecting group, or an amino protecting group, respectively.
Claim 13
Dependent Claim
105 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 thienediyl or furanediyl unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl, cyclohexadiyl, or alkanediyl having 2 to 4 carbon atoms; R 4' is hydrogen, methyl, hydroxymethyl, or hydroxymethyl substituted with a hydroxy protecting group; and R 5' is amino or amino substituted with an amino protecting group, at least one of R 2' , R 4' , and R 5 being a carboxy protecting group, a hydroxy protecting group, or an amino 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) | 1994-07-01 | 1994-12-31 | 1995-07-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-07-01 | 1998-12-31 | 1999-07-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-07-01 | 2002-12-31 | 2003-07-02 | $7700.00 | Window Closed / Lapsed |