Piperidylbenzimidazolinone compounds

• US 4,264,613 A
• Filed: 08/01/1979
• Issued: 04/28/1981
• Est. Priority Date: 08/01/1979
• Status: Expired due to Term

• Current Assignee: Science Union et CIE
• Original Assignee: Science Union et CIE Societe Francaise de Recherche Medicale
• Inventors: Dhainaut, Alain, Boulanger, Michelle, Duhault, Jacques, Regnier, Gilbert
• Primary Examiner(s): Jiles, Henry R.
• Assistant Examiner(s): Fan, Jane T.
• Application Number:
  US06/062,878
• Time in Patent Office: 636 Days
• Field of Search: 546/199, 424/267
• US Class Current: 514/322
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond

Abstract

Piperidylbenzimidazolinone compounds of the formula: ##STR1## in which: R is hydrogen, hydroxy, hydroxymethyl, methoxycarbonyl, formamido, acetamido, mesylamino, oxalamino, ethoxalylamino, carbamoyl ##STR2## ureido ##STR3## or sulfamoylamino ##STR4## in which R'"'"' and R" are hydrogen or lower alkyl, T is hydrogen, halogen, lower alkyl or lower alkoxy, and

Z is hydrogen, lower alkyl or lower alkenyl each in straight or branched chain.

These compounds and physiologically tolerable acid addition salts thereof may be used as medicines especially in the treatment of autoimmune, allergic and inflammatory diseases and in the treatment of respiratory insufficiency of asthma.

Claims

1. A compound selected from the group consisting of:

piperidylbenzimidazolinone compounds of the formula;

##STR18## in which;

R is selected from the group consisting of hydrogen, hydroxy (OH--), hydroxymethyl (HO--CH₂ --), formamido (H--CO--NH--), acetamido (CH₃ --CO--NH--), mesylamino (CH₃ --SO₂ --NH--), oxalamino (HOOC--CO--NH--), ethoxalylamino (C₂ H₅ OOC--CO--NH--), ureido ##STR19## and sulfamoylamino ##STR20## R'"'"' and R", being identical or different, are each selected from the group consisting of hydrogen and alkyl having from 1 to 5 carbon atoms inclusive,

T is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy each having from 1 to 5 carbon atoms inclusive, and

Z is selected from the group consisting of hydrogen, alkyl and alkenyl each having from 1 to 5 carbon atoms inclusive in straight and branched chain; and

physiologically tolerable salts thereof.

2. A compound of claim 1 which is 1-[2-(3,4-dihydroxyphenyl)-2-hydroxy]ethyl-4-(2-oxobenzimidazolin-1-yl)piperidine.

3. A compound of claim 1 which is 1-[2-(4-hydroxyphenyl)-2-hydroxy]ethyl-4-(2-oxobenzimidazolin-1-yl)piperidine.

4. A compound of claim 1 which is 1-[2-(3,5-dihydroxyphenyl)-2-hydroxy]ethyl-4-(2-oxobenzimidazolin-1-yl)piperidine and its hydrochloride.

5. A pharmaceutical composition having broncodilating, β

-adrenergic and anti-allergic activity containing an effective amount of a compound of claim 1 as active ingredient, together with a suitable physiologically acceptable carrier.

6. A method for treating a living animal body afflicted with antoimmune allergic or anti-inflammatory diseases or asthmatic dyspnea, comprising the step of administering an amount of a compound of claim 1 which is effective for the alleviation of the said condition.