4-amino-1-piperidylbenzoylguanidines
First Claim
1. A 4-amino-1-piperidylbenzoylguanidine of the formula I ##STR6## in which R1 and R2 are in each case independent of each other and are H, A, Ph, Ph--alk, CO--A, CO--Ph, CO--Het or an amino protective group known from peptide chemistry, orR1 and R2 are together alkylene having from four to five C atoms, where one or two CH2 groups can be replaced by --O--, --S--, --CO--, --NH--, --NA-- and/orN--CH2 --Ph, and optionally a phenyl ring can be fused to the ring formed by R1 and R2 such thata dihydroindolyl radical, a tetrahydroquinolinyl radical, a tetrahydroisoquinolinyl radical or a dihydrobenzimidazolyl radical is present,R3 and R4 are in each case independent of each other and are H, A, Hal, --X--R5, CN, NO2, CF3, CH2 --CF3, SOn --R7 or SO2 --NR5 R6,R5 is H, A, CF3, CH2 --CF3, Ph, Ph--alk, C5 -C7 -cycloalkyl or C5 -C7 -cycloalkyl-alk,R6 is H or A, orR5 and R6 are together alkylene having from four to five C atoms, where a CH2 group can be replaced by --O--, --S--, --NH--, --NA--, or --N--CH2 --Ph,R7 is A or Ph,X is O, S or N--R6,A is alkyl having from 1 to 6 C atoms,alk is alkylene having from 1 to 4 C atoms,Hal is F, Cl, Br or I,Ph is phenyl unsubstituted or substituted once, twice or three times by A, OA, Hal, CF3, NH2, NHA or NA2,Het is a saturated or unsaturated five- or six-membered heterocyclic radical having from 1 to 4 N, O and/or S atoms andn is 1 or 2,or a physiologically compatible salt thereof.
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Accused Products
Abstract
4-amino-1-piperidylbenzoylguanidines of the formula I ##STR1## in which R1, R2, R3 and R4 have the given meanings, and also the physiologically compatible salts thereof, exhibit antiarrhythmic properties and act as inhibitors of the cellular Na+ /H+ antiporter.
123 Citations
6 Claims
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1. A 4-amino-1-piperidylbenzoylguanidine of the formula I ##STR6## in which R1 and R2 are in each case independent of each other and are H, A, Ph, Ph--alk, CO--A, CO--Ph, CO--Het or an amino protective group known from peptide chemistry, or
R1 and R2 are together alkylene having from four to five C atoms, where one or two CH2 groups can be replaced by --O--, --S--, --CO--, --NH--, --NA-- and/or N--CH2 --Ph, and optionally a phenyl ring can be fused to the ring formed by R1 and R2 such that a dihydroindolyl radical, a tetrahydroquinolinyl radical, a tetrahydroisoquinolinyl radical or a dihydrobenzimidazolyl radical is present, R3 and R4 are in each case independent of each other and are H, A, Hal, --X--R5, CN, NO2, CF3, CH2 --CF3, SOn --R7 or SO2 --NR5 R6, R5 is H, A, CF3, CH2 --CF3, Ph, Ph--alk, C5 -C7 -cycloalkyl or C5 -C7 -cycloalkyl-alk, R6 is H or A, or R5 and R6 are together alkylene having from four to five C atoms, where a CH2 group can be replaced by --O--, --S--, --NH--, --NA--, or --N--CH2 --Ph, R7 is A or Ph, X is O, S or N--R6, A is alkyl having from 1 to 6 C atoms, alk is alkylene having from 1 to 4 C atoms, Hal is F, Cl, Br or I, Ph is phenyl unsubstituted or substituted once, twice or three times by A, OA, Hal, CF3, NH2, NHA or NA2, Het is a saturated or unsaturated five- or six-membered heterocyclic radical having from 1 to 4 N, O and/or S atoms and n is 1 or 2, or a physiologically compatible salt thereof.
Specification
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- Resources
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Current AssigneeMerck Patent GmbH (Merck & Co., Inc.)
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Original AssigneeMerck Patent GmbH (Merck & Co., Inc.)
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InventorsBeier, Norbert, Gericke, Rolf, Dorsch, Dieter, Baumgarth, Manfred, Lues, Ingeborg, Minck, Klaus-Otto
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Primary Examiner(s)Ivy, C. Warren
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Assistant Examiner(s)NORTHINGTON DAVIS, ZINNA
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Application NumberUS08/385,790Time in Patent Office257 DaysField of Search546/223, 546/224, 514/329US Class Current514/329CPC Class CodesA61P 9/00 Drugs for disorders of the ...A61P 9/06 AntiarrhythmicsA61P 9/10 for treating ischaemic or a...C07D 211/58 attached in position 4C07D 401/04 directly linked by a ring-m...
