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Pharmaceutical piperidine derivatives

Assignee: Novartis Corp
•
Filing: 1976-01-28
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Granted: 1978-02-21
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Expires: 1996-01-28
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Abstract

Abstract Piperidines of the formula <IMAGE> in which R1 stands for optionally substituted aryl, R2 for hydrogen, lower alkyl, lower alkenyl, acyl or alpha -aryl-lower alkyl, R3 for a free or substituted hydroxyl group, alk for lower alkylene which separates the two nitrogen atoms by 2 or 3 carbon atoms, R4 represents hydrogen or lower alkyl and n represents an integer from 1 to 4, and their salts as well as processes for their manufacture and pharmaceutical compositions comprising such compounds, and a process for lowering the blood pressure wherein such compositions are administered to a warm-blooded host.

Inventors

  • 👤 Max Wilhelm
  • 👤 Kurt Eichenberger
  • 👤 Herbert Schroter
  • 👤 Franz Ostermayer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 06:45
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/75; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/435; A61K31/44; A61K31/445; A61K31/495; A61K31/63; A61K31/635

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 163 words
A pharmaceutical composition useful in treating hypertension and tachycardia which comprises an anti-hypertensively and anti-tachycardially effective amount of a piperidine compound having the formula ##STR14## wherein R 1 is phenyl, naphthyl, 5,6,7,8-tetrahydro-1-naphthyl or 5,6,7,8-tetrahydro-2-naphthyl radical which is unsubstituted, monosubstituted or disubstituted by lower alkyl, lower alkoxy, lower alkenyl, lower alkenyloxy, halogen, halogeno-lower alkyl, carbamoyl, lower alkyl-substituted carbamoyl, lower alkoxycarbonylamino-lower alkyl, lower alkoxy-lower alkoxy, lower alkanoylaminoethenyl, lower alkylthio-lower alkoxy, hydroxyl, lower alkanoyl, lower alkoxy-lower alkyl, lower alkynyl, lower alkylthio-lower alkyl, hydroxy-lower alkyl, lower alkanoyloxy, lower alkylthio, lower alkanoyl amino, cyano, amino, nitro, ureido, lower alkylated ureido, phenyl-lower alkoxy, or lower alkynyloxy, R 2 is hydrogen, lower alkyl, lower alkenyl, α-phenyl-lower alkyl or lower alkanoyl, R 3 is a free hydroxyl group, a lower alkanoyloxy group or a lower alkoxy group, R 4 is hydrogen or lower alkyl, n is an integer from 0 to 4, and alk is an optionally mono-lower alkylated ethylene radical or a salt thereof, together with a therapeutically useful carrier.
Claim 2
Dependent Claim 163 words
A pharmaceutical composition useful in treating hypertension and tachycardia which comprises an anti-hypertensively and anti-tachycardially effective amount of a piperidine compound having the formula ##STR14## wherein R 1 is phenyl, naphthyl, 5,6,7,8-tetrahydro-1-naphthyl or 5,6,7,8-tetrahydro-2-naphthyl radical which is unsubstituted, monosubstituted or disubstituted by lower alkyl, lower alkoxy, lower alkenyl, lower alkenyloxy, halogen, halogeno-lower alkyl, carbamoyl, lower alkyl-substituted carbamoyl, lower alkoxycarbonylamino-lower alkyl, lower alkoxy-lower alkoxy, lower alkanoylaminoethenyl, lower alkylthio-lower alkoxy, hydroxyl, lower alkanoyl, lower alkoxy-lower alkyl, lower alkynyl, lower alkylthio-lower alkyl, hydroxy-lower alkyl, lower alkanoyloxy, lower alkylthio, lower alkanoyl amino, cyano, amino, nitro, ureido, lower alkylated ureido, phenyl-lower alkoxy, or lower alkynyloxy, R 2 is hydrogen, lower alkyl, lower alkenyl, α-phenyl-lower alkyl or lower alkanoyl, R 3 is a free hydroxyl group, a lower alkanoyloxy group or a lower alkoxy group, R 4 is hydrogen or lower alkyl, n is an integer from 0 to 4, and alk is an optionally mono-lower alkylated ethylene radical or a salt thereof, together with a therapeutically useful carrier.
Claim 3
Dependent Claim 74 words
The pharmaceutical composition of claim 1, wherein the active compound has the formula defined in claim 1, wherein R 1 is a phenyl radical mono- or di-substituted by lower alkyl, lower alkoxy, lower alkenyl, lower alkenyloxy, lower alkanoyl, lower alkanoylamino, hydroxyl, benzyloxy, N-lower alkylcarbamoyl or halogen, R 2 is hydrogen or lower alkyl, R 3 is hydroxyl, R 4 is hydrogen or methyl, n is 1 and alk is an optionally monomethylated ethylene radical.
Claim 4
Dependent Claim 50 words
The pharmaceutical composition of claim 1, wherein the active compound has the formula defined in claim 1, wherein R 1 is phenyl monosubstituted by methyl, methoxy, allyl, allyloxy, hydroxyl, acetylamino, propionyl, N-methyl-carbamoyl or chlorine, R 2 is hydrogen, R 3 is hydroxyl, R 4 is hydrogen and alk is ethylene.
Claim 5
Dependent Claim 46 words
The pharmaceutical composition of claim 1, wherein the active compound has the formula ##STR15## in which R' stands for halogen, lower alkyl or lower alkoxy, R" for lower alkyl or hydrogen, R''' for methyl or hydrogen and alk' for ethylene or an acid addition salt thereof.
Claim 6
Dependent Claim 34 words
The pharmaceutical composition of claim 1, wherein the active compound has the formula ##STR16## in which R' stands for lower alkyl or lower alkoxy and alk' for ethylene or an acid addition salt thereof.
Claim 7
Dependent Claim 18 words
The pharmaceutical composition of claim 1, wherein the active compound is 1-[3-(o-chlorophenoxy)-2-hydroxypropyl]-4-(2-oxo-1-imidazolidinyl)-piperidine or an acid addition salt thereof.
Claim 8
Dependent Claim 18 words
The pharmaceutical composition of claim 1, wherein the active compound is 1-[3-(o-methylphenoxy)-2-hydroxypropyl]-4-(2-oxo-1-imidazolidinyl)-piperidine or an acid addition salt thereof.
Claim 9
Dependent Claim 18 words
The pharmaceutical composition of claim 1, wherein the active compound is 1-[3-(o-methoxyphenoxy)-2-hydroxypropyl]-4-(2-oxo-1-imidazolidinyl)-piperidine or an acid addition salt thereof.
Claim 10
Dependent Claim 47 words
A pharmaceutical composition useful in treating hypertension and tachycardia which comprises a therapeutically effective amount of a piperidine compound defined in claim 1 and a therapeutically effective amount of an anti-hypertensive agent selected from the group consisting of α-amino-α-methyl-β-(3,4-dihydroxyphenyl)-propionic acid, β-amino-α-(3,4-dimethoxy-phenyl)-propionic acid, 1,4-dihydrazinophthalazine, 1-hydrazinophthalazine, 2-[(N-p-tolyl)-N-(m-hydroxyphenyl)-aminomethyl]-imidazoline or β-(1-azacyclooctyl)-ethylguanidine.
Claim 11
Dependent Claim 17 words
The pharmaceutical composition as claimed in claim 9, containing 1-{1-[3-(o-methoxy-phenoxy)-2-hydroxy-1-propyl]-piperidyl-(4)}-imidazolidinone-(2) together with 1-α-amino-α-methyl-β-(3,4-dihydroxyphenyl)-propionic acid or β-(1-azacyclooctyl)-ethylguanidine sulphate.
Claim 12
Dependent Claim 53 words
A pharmaceutical composition useful in treating hypertension and tachycardia which comprises a therapeutically effective amount of a piperidine compound defined in claim 1 and a therapeutically effective amount of a diuretic selected from the group consisting of 6-chloro-7-sulphamyl-1,2,4-benzothiadiazine-1,1-dioxide, 6-trifluoromethyl-7-sulphamyl-1,2,4-benzothiadiazine-1,1-dioxide, 2-benzylthiomethyl-6-chloro-7-sulphamyl-1,2,4-benzothiadiazine-1,1-dioxide, 3-ethyl-6-chloro-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide, 3-trichloromethyl-6-chloro-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide, 3-benzyl-6-trifluoromethyl-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide, 2-methyl-3-(2,2,2-trifluoroethylthiomethyl)-6-chloro-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide, 3-(2,2,2-trifluoroethylthiomethyl)-6-chloro-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide, 3-(5-norbornen-2-yl)-6-chloro-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide, 2-methyl-3-chloromethyl-6-chloro-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide, 6-chloro-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide, 3-dichloromethyl-6-chloro-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide, 3-cyclopentylmethyl-6-chloro-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide, 6-trifluoromethyl-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide and 3-isobutyl-6-chloro-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide.
Claim 13
Dependent Claim 17 words
Pharmaceutical composition as claimed in claim 11, containing 1-{1-[3-(o-methoxy-phenoxy)-2-hydroxy-1-propyl]-piperidyl-(4)}-imidazolidinone-(2) together with 1-oxo-3-(3-sulphamyl-4-chloro-phenyl)-3-hydroxyisoindoline, 6-chloro-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide, 3-cyclopentylmethyl-6-chloro-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide or 5-(2-methylenebutyryl)-6-methyl-benzofurane2-carboxylic acid.
Claim 14
Dependent Claim 24 words
A method for the treatment of hypertension of tachycardia which comprises administering to a mammal afflicted therewith a pharmaceutical composition according to claim 1.

References Cited (Backward Citations)

US3318900A Cited
US3459757A Cited
US3969518A Cited
US3956335A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-02-20 1981-08-22 1982-02-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-02-20 1985-08-22 1986-02-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-02-20 1989-08-22 1990-02-21 $7700.00 Window Closed / Lapsed

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