# US 5,705,654 A · Imidazolidines substituted with a heterocycle

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- Number: US 5,705,654 A
- Document ID: US5705654A
- Status: Granted
- Kind: A
- Application number: 08/695,690
- Filed: 1996-08-12
- Granted: 1998-01-06
- Earliest claimed: 1994-09-29
- Assignees: Roussel Uclaf
- Inventors: Andre Claussner; Francois Goubet; Jean-Georges Teutsch
- Web page: https://patentgrep.com/patent/US5705654A

## CPC

- C07D 471/10: Spiro-condensed systems
- A61P 5/28: Antiandrogens
- A61P 13/08: of the prostate
- A61P 17/00: Drugs for dermatological disorders
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 491/10: Spiro-condensed systems
- C07D 495/10: Spiro-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Described herein are novel imidazoles of the formula ##STR1## wherein the substituents are as defined in the disclosure and their non-toxic, pharmaceutically acceptable addition salts with acids and bases having antiandrogenic activity.

## Claims

### Claim 1

A compound of the formula ##STR36## wherein H is ##STR37## Z.sub.1 is selected from the group consisting of oxygen, and optionally oxidized sulfur
Ar is phenyl optionally substituted with at least one member of the group consisting of halogen, cyano, nitro, trifluoromethyl, trifluoromethyoxy, hydroxyl, free, salified, esterified or amidified carboxy, alkyl, alkoxy and alkylthio of up to 6 carbon atoms, arylthio, amino, mono or dialkylamino, aminoalkyl, mono or dialkyl-aminoalkyl, aminoalkoxy, and mono or dialkylaminoalkoxy,
X is oxygen or sulfur,
Y is oxygen or sulfur or NH,
R.sub.3 is selected from the group consisting of hydrogen, aryl and alkyl, alkenyl and alkynyl optionally interrupted by at least one oxygen, nitrogen or optionally oxidized sulfur, all the groups being optionally substituted by at least one member of the group consisting of halogen, optionally salified, esterified or etherified hydroxy, alkoxy, aryloxy, alkyl, trifluoromethyl, trifluoromethoxy, free, salified, esterified or amidified carboxy, cyano, nitro, amino, mono or dialkylamino, phenyl, benzyl and phenethyl, the phenyls optionally substituted by at least one member of the group consisting of halogen, hydroxyl, alkyl, alkoxy, cyano, nitro and trifluoromethyl, the said products of formula I being in all the possible racemic, enantiomeric and diastereoisomeric isomer forms, or their non-toxic, pharmaceutically acceptable addition salts with acids or bases.

### Claim 2 (depends on 1)

A compound of claim 1 selected from the group consisting of 4-(2,4-dioxo-1-(4-hydroxybutyl)-8-oxa-1,3-diazaspiro(4.5)decan-3-yl)-2-(tr ifluoromethyl)-benzonitrile, 4-(2,4-dioxo-1-(2-fluoroethyl)-8-oxa-1,3-diazaspiro(4.5)decan-3-yl)-2-(tri fluoromethyl)-benzonitrile, 3-(4-cyano-3-(trifluoromethyl)-phenyl)-2,4-dioxo-8-oxa-1,3-diazaspiro(4.5) decane-1-acetonitrile and 4-(2,4-dioxo-1-(4-hydroxybutyl)-8-thia-1,3-diazaspiro(4.5)decan-3-yl)-2-(t rifluoromethyl)-benzonitrile.