Piperidylbenzimidazolinone derivatives

• US 4,338,323 A
• Filed: 11/10/1980
• Issued: 07/06/1982
• Est. Priority Date: 11/15/1979
• Status: Expired due to Term

• Current Assignee: Science Union et CIE
• Original Assignee: Science Union et CIE
• Inventors: Regnier, Gilbert, Dhainaut, Alain, Boulanger, Michelle, Duhault, Jacques
• Primary Examiner(s): Jiles, Henry R.
• Assistant Examiner(s): DENTZ, BERNARD I
• Application Number:
  US06/205,725
• Time in Patent Office: 603 Days
• Field of Search: 546/194, 546/199, 424/266, 424/267
• US Class Current: 514/318
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 401/14 containing three or more hetero rings

Abstract

Piperidylbenzimidazolinone derivatives of the formula: ##STR1## in which: R₁ is lower alkyl, phenyl, halophenyl, lower alkylphenyl, lower alkoxyphenyl, methylenedioxyphenyl, ethylenedioxyphenyl, thienyl, furyl or pyridyl.

R₂ is R'"'"'₁ COO-- or R'"'"'₁ --COO--CH₂ -- in which R'"'"'₁ has the same meanings as R₁, R₁ and R'"'"'₁ being the same or different, or R₃ NH-- in which R₃ is formyl, acetyl mesyl, carbamoyl, sulfamoyl or ethoxalyl.

Z is hydrogen, lower-alkyl or lower alkenyl, and

T is hydrogen, lower alkyl or lower alkoxy.

These compounds and physiologically tolerable acid addition salts thereof may be used as medicines especially in the treatment of autoimmune, allergic and antiinflammatory diseases and in the treatment of dyspnea especially asthmatic and bronchial dyspnea.

Claims

1. A compound selected from the group consisting of:

piperidylbenzimidazolinone derivatives of the formula;

##STR11## in which;

R₁ is selected from the group consisting of;

alkyl having from 1 to 6 carbon atoms inclusive in straight and branched chain,

unsubstituted phenyl and phenyl mono- and poly-substituted by a substituent selected from the group consisting of halogen, alkyl and alkoxy each having from 1 to 5 carbon atoms inclusive, methylenedioxy, and ethylenedioxy, and

thienyl, furyl, and pyridyl;

R₂ is selected from the group consisting of;

R'"'"'₁ --COO-- and R'"'"'₁ --COO--CH₂ -- in which R'"'"'₁ is a substituent selected from the meanings here-above given for R₁, R₁ and R'"'"'₁ being the same or different, and

R₃ --NH-- in which R₃ is selected from the group consisting of formyl, acetyl, mesyl, carbamoyl, sulfamoyl, and ethoxalyl;

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

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

physiologically tolerable acid addition salts thereof.

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

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

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

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

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

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

8. A pharmaceutical composition active as a bronchodilator containing as active ingredient between 20 and 80 milligrams per unit dose of a compound of claim 1 together with a suitable pharmaceutical carrier.

9. A method for treating a living animal body afflicted with autoimmune, allergic or antiinflammatory diseases, asthmatic dyspnea or chronic bronchitis, comprising the step of administering an amount of a compound of claim 1 which is effective for the alleviation of the said condition.