# US 5,344,932 A · N-(pyrrolo(2,3-d)pyrimidin-3-ylacyl)-glutamic acid derivatives

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- Number: US 5,344,932 A
- Document ID: US5344932A
- Status: Granted
- Kind: A
- Application number: 07/674,541
- Filed: 1991-03-22
- Granted: 1994-09-06
- Earliest claimed: 1989-12-11
- Assignees: The Trustees of Princeton University
- Inventors: Edward C. Taylor
- Web page: https://patentgrep.com/patent/US5344932A

## CPC

- C07D 487/04: Ortho-condensed systems
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- Y02P 20/582: Recycling of unreacted starting or intermediate materials
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## 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-hydroxy-6-aminopyrrolo-[2,3-d]pyrimidin-3-yl}ethyl)benzoyl]-L-g lutamic acid.

## Claims

### Claim 1

A compound of the formula: ##STR14## in which: R.sup.1 is --OH or --NH.sub.2 ;
R.sup.2 is hydrogen or a pharmaceutically acceptable cation:
R.sup.3 is 1,4-phenylene unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl;
R.sup.4 is hydrogen, or methyl;
R.sup.5 is amino; and
the configuration about the carbon atom designated * is S.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

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

### Claim 7

A compound of the formula: ##STR15## in which: R.sup.1 is --OH or --NH.sub.2 ;
R.sup.2' is hydrogen, a pharmaceutically acceptable cation, or a carboxy protecting group:
R.sup.3 is 1,4-phenylene unsubstituted or substituted with chloro, fluoro, methyl, methoxy, or trifluoromethyl;
R.sup.4' is hydrogen, or methyl;
R.sup.5' is amino or amino substituted with an amino protecting group; and
the configuration about the carbon atom designated * is S.