# US 4,393,062 A · Pharmaceutical compositions and method for the production of an anti-inflammatory effect

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- Number: US 4,393,062 A
- Document ID: US4393062A
- Status: Granted
- Kind: A
- Application number: 06/194,211
- Filed: 1980-10-06
- Granted: 1983-07-12
- Earliest claimed: 1977-12-29
- Assignees: Imperial Chemical Industries PLC
- Inventors: David R. Brittain; Robin Wood
- Web page: https://patentgrep.com/patent/US4393062A

## CPC

- C07D 491/04: Ortho-condensed systems
- A61P 3/08: for glucose homeostasis (pancreatic hormones A61P5/48)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 237/30: Phthalazines
- C07D 237/32: with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
- C07D 307/88: with one oxygen atom directly attached in position 1 or 3
- C07D 493/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

This invention relates to enzyme inhibitory, novel phthalazin-4-ylacetic acid derivatives of the general formula I: ##STR1## and pharmaceutically acceptable salts as appropriate, to pharmaceutical compositions thereof, and to analogy processes for their manufacture. The compounds of formula I are inhibitors of the enzyme aldose reductase in vivo and as such may be useful in the reduction or prevention of the development of the peripheral effects such as macular oedema, cataract, retinopathy or impaired neural conduction. A preferred compound is 2-(2-fluoro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid.

## Claims

### Claim 1

A pharmaceutical composition suitable for use in producing an anti-inflammatory effect in a warm-blooded animal which comprises a compound of the formula: ##STR20## wherein R.sup.1 is hydroxy, R.sup.2 is fluoro, R.sup.3 and R.sup.5 are hydrogen and R.sup.4 is chloro, bromo or iodo; or R.sup.2 and R.sup.5 are hydrogen, and R.sup.3 and R.sup.4 are each independently chloro, bromo or iodo; and in either case R.sup.6, R.sup.7 and R.sup.8 are hydrogen and X is oxygen; or a pharmaceutically acceptable base-addition salt thereof; together with a pharmaceutically acceptable diluent or carrier.

### Claim 2 (depends on 1)

The pharmaceutical composition of claim 1 wherein the compound of formula I is selected from the group consisting of 2-(2-fluoro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid, 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid, and the pharmaceutically acceptable base-addition salts thereof.

### Claim 3 (depends on 1)

The pharmaceutical composition of claim 1 which is in a form suitable for oral administration, said form being one of a tablet, capsule, suspension or solution.

### Claim 4 (depends on 1)

A method for the production of an anti-inflammatory effect in a warm-blooded animal requiring such treatment which comprises administering to said animal a therapeutically effective amount of a compound of formula I, or a pharmaceutically acceptable base-addition salt thereof, as defined in claim 1.

### Claim 5 (depends on 4)

The method of claim 4 wherein said compound is selected from the group consisting of 2-(2-fluoro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid, 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazine-4-ylacetic acid, and the pharmaceutically acceptable base-addition salts thereof.