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US4136185A Expired / Lapsed US ⏱️ 0.0 years remaining

N-Aryl-N'-(phenyl-or phenoxy-alkyl)-piperazines and salts thereof

Assignee: Boehringer Ingelheim GmbH
•
Filing: 1978-03-15
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Granted: 1979-01-23
•
Expires: 1998-03-15
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Abstract

Abstract Compounds of the formula ##STR1## wherein R is phenyl; phenyl having one or two substituents attached thereto, said substituents being selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, chlorine and trifluoromethyl; naphthyl; tetrahydronaphthyl; indanyl; pyridyl; isoquinolyl; or thiazolyl; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms; R 4 and R 5 are each hydrogen or alkyl of 1 to 4 carbon atoms; Q is oxygen or two hydrogens; R 2 is hydrogen, alkyl of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms or halogen; A is a single carbon-to-carbon bond or --OCH 2 --; R 6 is hydrogen, hydroxyl, alkoxy of 1 to 4 carbon atoms or alkanolyloxy of 1 to 4 carbon atoms, and M is 0, 1, 2, 3, 4 or 5, but other than O when R 6 is hydroxyl, And non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as CNS-depressants, adrenolytics, antiphlogistics, analgesics, antihistaminics and antihypercholesteremics.

Inventors

  • 👤 Ernst-Otto Renth
  • 👤 Anton Mentrup
  • 👤 Kurt Schromm
  • 👤 Peter Danneberg

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 15:57
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24; C07D207/26; C07D207/263; C07D207/27; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/495

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 172 words
A compound of the formula ##STR29## wherein R is phenyl; phenyl having one or two substituents attached thereto, said substituents being selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, chlorine and trifluoromethyl; naphthyl; 1- or 2-tetrahydronaphthyl; 1- or 2-indanyl; pyridyl; or thiazolyl; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms; R 4 and R 5 are each hydrogen or alkyl of 1 to 4 carbon atoms; Q is oxygen or two hydrogens; R 2 is hydrogen, alkyl of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms or halogen; A is a single carbon-to-carbon bond or --OCH 2 --; R 6 is hydrogen, hydroxyl, alkoxy of 1 to 4 carbon atoms or alkanolyloxy of 1 to 4 carbon atoms, and m is 0, 1, 2, 3, 4 or 5, but other than 0 when R 6 is hydroxyl, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 2
Dependent Claim 172 words
A compound of the formula ##STR29## wherein R is phenyl; phenyl having one or two substituents attached thereto, said substituents being selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, chlorine and trifluoromethyl; naphthyl; 1- or 2-tetrahydronaphthyl; 1- or 2-indanyl; pyridyl; or thiazolyl; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms; R 4 and R 5 are each hydrogen or alkyl of 1 to 4 carbon atoms; Q is oxygen or two hydrogens; R 2 is hydrogen, alkyl of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms or halogen; A is a single carbon-to-carbon bond or --OCH 2 --; R 6 is hydrogen, hydroxyl, alkoxy of 1 to 4 carbon atoms or alkanolyloxy of 1 to 4 carbon atoms, and m is 0, 1, 2, 3, 4 or 5, but other than 0 when R 6 is hydroxyl, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 3
Dependent Claim 17 words
A compound of claim 1, which is N-[p-(1-hexahydropyrimidin-2-one-yl)-phenethyl]-N'-(m-tolyl)-piperazine or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 4
Dependent Claim 17 words
A compound of claim 1, which is N-[p-1-hexahydropyrimidin-2-one-yl)-phenethyl]-N'-(o-tolyl)-piperazine or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 5
Dependent Claim 23 words
A pharmaceutical dosage unit composition consisting essentially of an inert pharmaceutical carrier and an effective CNS-depressing amount of a compound of claim 1.
Claim 6
Dependent Claim 35 words
The method of depressing the central nervous system of a warm-blooded animal in need thereof, which comprises perorally, parenterally or rectally administering to said animal an effective CNS-depressing amount of a compound of claim 1.

References Cited (Backward Citations)

US3530131A Cited
US3562270A Cited
US3787411A Cited
US3770737A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-01-22 1982-07-24 1983-01-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-01-22 1986-07-24 1987-01-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-01-22 1990-07-24 1991-01-23 $7700.00 Window Closed / Lapsed

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