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US3941789A Expired / Lapsed US ⏱️ 0.0 years remaining

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

Assignee: Boehringer Ingelheim GmbH
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Filing: 1973-12-21
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Granted: 1976-03-02
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Expires: 1993-12-21
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Abstract

Abstract Compounds of the formula A-CH-CmH2m-NN-R ¦ R6 wherein R is phenyl; phenyl having one or more 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, halogen and trifluoromethyl; a bicyclic aromatic or cycloaliphatic-aromatic ring, especially naphthyl, tetrahydronaphthyl or indanyl; or a mono- or bicyclic heterocyclic ring, especially pyridyl, pyrimidyl, isoquinolyl or thiazolyl; R1is (CH2)pR4 ANGLE ANGLE -N(CH2)n or Q=CR5 ANGLE ¦¦ B -NN-R3 ANGLE C PARALLEL O where B is O OO PARALLEL ANGLE -C- or -S-, n is 2, 3 or 4, R3 is hydrogen, alkyl of 1 to 4 carbon atoms or alkanoyl of 1 to 4 carbon atoms, R4 and R5, which may be identical to or different from each other, are each hydrogen or alkyl of 1 to 4 carbon atoms, P IS 0 OR 1, AND Q is oxygen or two hydrogens, R2 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 -OCH2-, R6 is hydrogen, hydroxyl, alkoxy of 1 to 4 carbon atoms or alkanoyloxy of 1 to 4 carbon atoms, and M IS 0, 1, 2, 3, 4 OR 5, BUT OTHER THAN 0 WHEN R6 is hydroxyl, AND NON-TOXIC, PHARMACOLOGICALLY ACCEPTABLE ACID ADDITION SALTS THEREOF; THE COMPOUNDS AS WELL AS THEIR SALTS ARE USEFUL AS CNS-depressants, adrenolytics, antiphologistics, analgesics, antihistamines and anticholesterols.

Inventors

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

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 20:35
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; A61P; A61P11/00; A61P11/08; A61P25/00; A61P25/02; A61P25/04; A61P25/20; A61P29/00; A61P3/00; A61P3/06; A61P43/00; A61P9/00; A61P9/02; A61P9/12; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088; C07D295/12; C07D295/135

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 187 words
A racemic or optically active compound of the formula ##EQU21## 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; thiazolyl; or isoquinolyl; R 1 is ##EQU22## where B is ##EQU23## n is 2 or 3 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, and 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 alkanoyloxy 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 187 words
A racemic or optically active compound of the formula ##EQU21## 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; thiazolyl; or isoquinolyl; R 1 is ##EQU22## where B is ##EQU23## n is 2 or 3 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, and 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 alkanoyloxy 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-pyrrolidin-2-one-yl)-phenethyl]-N'-(2',3'-xylyl)-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-piperidin-2-one-yl)-phenethyl]-N'-(o-tolyl)-piperazine or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 5
Dependent Claim 17 words
A compound of claim 1, which is N-[p-(1-isothiazolidin-1,1-dioxide-yl)-phenethyl]-N'-(2',3'-xylyl)-piperazine or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 6
Dependent Claim 17 words
A compound of claim 1, which is N-[p-(1-imidazolidin-2,5-dione-yl)-phenethyl]-N'-(β-indanyl)-piperazine or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 7
Dependent Claim 17 words
A compound of claim 1, which is N-[p-(1-imidazolidin-2,5-dione-yl)-phenethyl]-N'-phenyl-piperazine or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 8
Dependent Claim 17 words
A compound of claim 1, which is N-[p-(1-imidazolidin-2,5-dione-yl)-phenethyl]-piperazine or a non-toxic, pharmacologically acceptable acid addition salt thereof.

References Cited (Backward Citations)

US3530131A Cited
US3562277A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-03-02 1979-09-01 1980-03-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-03-02 1983-09-01 1984-03-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-03-02 1987-09-01 1988-03-02 $7700.00 Window Closed / Lapsed

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