US4000274A
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Pharmaceutical compositions containing an n-aryl-n'-(phenyl-or-phenoxy-alkyl)-piperazine and method of use
Assignee: Boehringer Ingelheim GmbH
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Filing: 1975-12-01
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Granted: 1976-12-28
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Expires: 1995-12-01
Abstract
Abstract Pharmaceutical compositions containing as an active ingredient a racemic or optically active compound 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, alkyl-thio of 1 to four carbon atoms, chlorine and trifluoromethyl; naphthyl; tetrahydronaphthyl; indanyl; pyridyl; thiazolyl; or isoquinolyl; R.sub. 1 is ##STR2## where B is ##STR3## 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; and a method of using the same as CNS-depressants, adrenolytics, antiphlogistics, analgesics, antihistaminics and anticholesteremics.
Inventors
- 👤 Ernst-Otto Renth
- 👤 Anton Mentrup
- 👤 Kurt Schromm
- 👤 Peter Danneberg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 09:29
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/495
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
202 words
A CNS-depressing pharmaceutical dosage unit composition consisting essentially of an inert pharmaceutical carrier and an effective CNS-depressing amount of a compound of the formula ##STR48## 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, alkyl-thio of 1 to 4 carbon atoms, chlorine and trifluoromethyl; naphthyl; tetrahydronaphthyl; indanyl; pyridyl; thiazolyl; or isoquinolyl; R 1 is ##STR49## where B is ##STR50## 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
202 words
A CNS-depressing pharmaceutical dosage unit composition consisting essentially of an inert pharmaceutical carrier and an effective CNS-depressing amount of a compound of the formula ##STR48## 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, alkyl-thio of 1 to 4 carbon atoms, chlorine and trifluoromethyl; naphthyl; tetrahydronaphthyl; indanyl; pyridyl; thiazolyl; or isoquinolyl; R 1 is ##STR49## where B is ##STR50## 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
19 words
A composition of claim 1, wherein said compound 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
19 words
A composition of claim 1, wherein said compound 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 5
Dependent Claim
19 words
A composition of claim 1, wherein said compound 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 6
Dependent Claim
19 words
A composition of claim 1, wherein said compound is N-[p-(1-imidazolidin-2,5-dione-yl)-phenethyl]-N'-phenylpiperazine or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
19 words
A composition of claim 1, wherein said compound is N-[p-(1-imidazolidin-2,5-dione-yl)-phenethyl]-piperazine or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 8
Independent Claim
215 words
The method of depressing the central nervous system of a warm-blooded animal in need of such treatment, which comprises perorally, parenterally or rectally administering to said animal an effective CNS-depressing amount of a compound of the formula ##STR51## 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 trifluoromethy; naphthyl; tetrahydronaphthyl; indanyl; pyridyl; thiazolyl; or isoquinolyl; R 1 is ##STR52## where B is ##STR53## 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 9
Independent Claim
215 words
The method of depressing the central nervous system of a warm-blooded animal in need of such treatment, which comprises perorally, parenterally or rectally administering to said animal an effective CNS-depressing amount of a compound of the formula ##STR51## 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 trifluoromethy; naphthyl; tetrahydronaphthyl; indanyl; pyridyl; thiazolyl; or isoquinolyl; R 1 is ##STR52## where B is ##STR53## 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 10
Dependent Claim
19 words
The method of claim 7, where said compound 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 11
Dependent Claim
19 words
The method of claim 7, where said compound is N-[p-(1-piperidin-2-one-yl)-phenethyl]-N'-(o-tolyl)-piperazine or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 12
Dependent Claim
19 words
The method of claim 7, where said compound 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 13
Dependent Claim
19 words
The method of claim 7, where said compound 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 14
Dependent Claim
19 words
The method of claim 7, where said compound is N-[p-(1-imidazolidin-2,5-dione-yl)-phenethyl]-N'-phenylpiperazine or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 15
Dependent Claim
19 words
The method of claim 7, where said compound 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)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-12-28 | 1980-06-28 | 1980-12-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-12-28 | 1984-06-28 | 1984-12-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-12-28 | 1988-06-28 | 1988-12-28 | $7700.00 | Window Closed / Lapsed |