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Last Updated: March 19, 2024

Details for Patent: 5,028,608


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Title: N-(6-Amino-(pyrrolo(2,3-d)pyrimidin-3-ylacyl) )-glutamic acid derivatives
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-ylcar bonyl}-L-glutamic acid.
Inventor(s): Taylor; Edward C. (Princeton, NJ), Kuhnt; Dietmar G. (Leverkusen, DE), Shih; Chuan (Indianapolis, IN), Grindey; Gerald B. (Indianapolis, IN)
Assignee: The Trustees of Princeton University (Princeton, NJ)
Filing Date:May 24, 1990
Application Number:07/528,155
Claims:1. A compound of the formula: ##STR16## in which: R.sup.1 is --OH or --NH.sub.2 ;

R.sup.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.sup.4 is hydrogen, methyl, orhydroxymethyl; and the configuration about the carbon atom designated * is S; and

the pharmaceutically acceptable salts thereof.

2. A compound according to claim 1 wherein R.sup.1 is --OH; R.sup.3 is thienediyl, and R.sup.4 is hydrogen.

3. The compound according to claim 1 which is N-{5-[2-(4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidin-3-yl)-ethyl]thien-2-ylca rbonyl}-L-glutamic acid.

4. The compound according to claim 1 which is N-{4-[2-(4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidin-3-yl)-ethyl]thien-2-ylca rbonyl}-L-glutamic acid.

5. The compound according to claim 1 which is N-{5-[2-(4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidin-3-yl)ethyl]thien-3-ylcar bonyl}-L-glutamic acid.

6. The compound according to claim 1 which is N-[5-(4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidin-3-yl)pentanoyl]-L-glutamic acid.

7. The compound according to claim 1 which is N-[7-(4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidin-3-yl)heptanoyl]-L-glutamic acid.

8. The compound according to claim 1 which is N-[6-(4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidin-3-yl)hexanoyl]-L-glutamic acid

9. 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.

10. 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.

11. A compound of the formula: ##STR17## in which: R.sup.1 is --OH or --NH.sub.2 ;

R.sup.2' is hydrogen, or a carboxy protecting group;

R.sup.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.sup.4' is hydrogen, methyl, hydroxymethyl, or hydroxymethyl substituted with a hydroxy protecting group; and

R.sup.5' is amino or amino substituted with an amino protecting group,

at least one of R.sup.2', R.sup.4', and R.sup.5 being a carboxy protecting group, a hydroxy protecting group, or an amino protecting group, respectively.

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