# US 4,394,385 A · Treatment of gray matter edema

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 4,394,385 A
- Document ID: US4394385A
- Status: Granted
- Kind: A
- Application number: 06/344,148
- Filed: 1982-01-29
- Granted: 1983-07-19
- Earliest claimed: 1978-02-22
- Assignees: Merck & Co., Inc.
- Inventors: Edward J. Cragoe, Jr.
- Web page: https://patentgrep.com/patent/US4394385A

## CPC

- A61K 31/34: having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

The invention relates to the treatment of gray matter edema in the brain or spinal chord by the administration of benzofuranyloxyacetic acids, indeno[5,4-b]furancarboxylic acids, their analogs and salts thereof.

## Claims

### Claim 1

A method of treating persons with gray matter edema which comprises administering to such a person an effective amount of a compound of the formulae: ##STR2## wherein R.sup.1 is H, CH.sub.3 or Cl
R.sup.2 is CH.sub.3 or Cl
R.sup.3 is alkyl or alkenyl of one through six carbons; cycloalkyl or cycloalkylalkyl of four through seven carbons; phenyl, unsubstituted or substituted with chloro or methyl; benzyl; or thienyl
R.sup.4 is H, alkyl of one through five carbons, or R.sup.4 and R.sup.3 taken together with the carbon to which they are attached may be joined to form a cycloalkyl radical of five or six carbons, and
R.sup.5 is (1) furyl, (2) thienyl, (3) phenyl, unsubstituted or substituted with methyl, methoxy or halo, or (4) benzyl, unsubstituted or substituted with methyl or halo
or the pharmaceutically acceptable salt, ester, or amide derivative thereof.

### Claim 2 (depends on 1)

The method of claim 1 where R.sup.3 is alkyl of one through five carbons, cycloalkyl or cycloalkylalkyl of four through six carbons, benzyl, phenyl or together with R.sup.4 is tetramethylene; R.sup.4 is H or alkyl of one through five carbons; and R.sup.5 is furyl, thienyl, benzyl, or phenyl substituted with chloro or methyl.

### Claim 3 (depends on 2)

The method of claim 2 where R.sup.1 and R.sup.2 are both chloro or both methyl; R.sup.3 is alkyl of one through three carbons, phenyl cyclobutyl, cyclopentyl, cyclohexyl, or benzyl; R.sup.4 is H, methyl, or ethyl; R.sup.3 together with R.sup.4 are tetramethylene; and R.sup.5 is furyl, thienyl, benzyl, p-chlorophenyl, or p-methoxyphenyl.

### Claim 4 (depends on 3)

The method of claim 3 where the compound is of formula I.

### Claim 5 (depends on 4)

The method of claim 4 where R.sup.1 and R.sup.2 are chloro, and R.sup.3 is phenyl, alkyl of one through three carbons, or cycloalkyl of four through six carbons.

### Claim 6 (depends on 5)

The method of claim 5 where the compound is in .alpha.-diastereomer, R.sup.3 is cyclopentyl and R.sup.4 is methyl.

### Claim 7 (depends on 5)

The method of claim 5 where the compound is in .alpha.-diastereomer, R.sup.3 is phenyl and R.sup.4 is methyl.

### Claim 8 (depends on 5)

The method of claim 5 where the compound is the .beta.-diastereomer, R.sup.3 is phenyl and R.sup.4 is methyl.

### Claim 9 (depends on 4)

The method of claim 4 where R.sup.1 and R.sup.2 are methyl, R.sup.3 is propyl, and R.sup.4 is H.

### Claim 10 (depends on 3)

The method of claim 3 where the compound is of formula II.

### Claim 11 (depends on 10)

The method of claim 10 where R.sup.5 is 2-furyl.

### Claim 12 (depends on 1)

The method of claim 1 where the compound is in the + configuration.

### Claim 13 (depends on 1)

The method of claim 1 where the compound is in the - configuration.

### Claim 14 (depends on 1)

The method of claim 1 for treating persons with spinal chord injury.

### Claim 15 (depends on 1)

The method of claim 1 for treating persons with hydrocephalus.

### Claim 16 (depends on 1)

The method of claim 1 for treating persons with ischemic stroke.

### Claim 17 (depends on 1)

The method of claim 1 for treating persons with head injury.