# US 5,352,701 A · Leukotriene-B.sub.4 antagonist compounds and their use as pharmaceutical agents

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- Number: US 5,352,701 A
- Document ID: US5352701A
- Status: Granted
- Kind: A
- Application number: 08/050,195
- Filed: 1993-05-05
- Granted: 1994-10-04
- Earliest claimed: 1990-09-07
- Assignees: Schering Corporation
- Inventors: Josef Heindl; Werner Skuballa; Bernd Buchmann; Wolfgang Frohlich; Roland Ekerdt; Claudia Giesen
- Web page: https://patentgrep.com/patent/US5352701A

## CPC

- C07D 213/79: Acids; Esters
- A61K 31/19: Carboxylic acids, e.g. valproic acid (salicylic acid A61K31/60)
- A61K 31/215: of carboxylic acids
- A61K 31/44: Non condensed pyridines; Hydrogenated derivatives thereof
- A61K 31/557: Eicosanoids, e.g. leukotrienes {or prostaglandins}
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 17/00: Drugs for dermatological disorders
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- C07C 59/68: the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C 59/90: containing singly bound oxygen-containing groups
- C07C 69/738: Esters of keto-carboxylic acids {or aldehydo-carboxylic acids}
- C07C 69/94: of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

1. Leukotriene-B.sub.4 antagonists of formula I ##STR1## are described, in which X is a CH.sub.2 group or an oxygen atom, Y is C.sub.1 -C.sub.4 -alkoxy or --S(O).sub.p --C.sub.1 -C.sub.4 -alkyl, p is 0, 1 or 2 Z is a hydrogen atom or the radical A-B-COOH with A being a hydroxymethylene group or a carbonyl group and B being an alkylene group with 1-6 atoms in the chain or a radical ##STR2## with the exception that B cannot mean the radical ##STR3## if X is a CH.sub.2 group, R.sub.1 is the radical OH, --O--(C.sub.1 --C.sub.4) -alkyl, --O--(C.sub.3-C.sub.6) -cycloalkyl, --O--(C.sub.7-C.sub.12) -aralkyl or the radical NHR.sub.4 with R.sub.4 being hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.3 -C.sub.6)-cycloalkyl, C.sub.6 -C.sub.10 -aryl or (C.sub.7 -C.sub.12)-aralkyl as well as their salts with physiologically compatible bases and their cyclodextrin clathrates, process for their production and their use as pharmaceutical agents.

## Claims

### Claim 1

A leukotriene-B.sub.4 antagonist of formula I ##STR13## wherein: X is a CH.sub.2 group or an oxygen atom,
Y is C.sub.1 -C.sub.4 -alkoxy or --S(O).sub.p --C.sub.1 -C.sub.4 -alkyl,
p is 0, 1 or 2,
Z is a hydrogen atom or the radical A-B-COOH, with A being a hydroxymethylene group or a carbonyl group and B being an alkylene group with 1-6 atoms in the chain or a radical ##STR14## with the exception that B is not the radical ##STR15## if X is a CH.sub.2 group, R.sub.1 is the radical OH, --O--(C.sub.1 -C.sub.4)-alkyl, --O--(C.sub.3 -C.sub.6)-cycloalkyl, --O--(C.sub.6 -C.sub.10)-aryl, --O--(C.sub.7 -C.sub.12)-aralkyl or the radical NHR.sub.6, where R.sub.4 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.3 -C.sub.6)-cycloalkyl or (C.sub.7 -C.sub.12)-aralkyl or salts with physiologically compatible bases and cyclodextrin clathrates thereof.

### Claim 2 (depends on 1)

A pharmaceutical agent comprising a compound according to claim 1 and a pharmaceutically acceptable excipient.

### Claim 3 (depends on 1)

A compound according to claim 1:
3-[2-[6-(4-methoxyphenyl)-(5E)-hexenyloxy]-phenyl]-propionic acid.

### Claim 4 (depends on 1)

A compound according to claim 1, wherein Y is C.sub.1 -C.sub.4 -alkoxy.

### Claim 5 (depends on 1)

A compound according to claim 1, wherein Y is CH.sub.3 --O--.

### Claim 6 (depends on 1)

A compound according to claim 1, wherein Y is C.sub.1-4 -alkoxy, X is CH.sub.2, and R.sub.1 is OH.