US 5,204,374 AGranted

Cycloalkano(b)dihydroindoles and -indolesulphonamides substituted by heterocycles

AssigneeBayer Aktiengesellschaft

InventorsUlrich E. Muller, Ulrich Rosentreter, Ulrich Niewohner, Elisabeth Perzborn, Erwin Bischoff, Hans-Georg Dellweg, Peter Norman, Nigel J. Cuthbert, Hilary P. Francis

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Abstract

New cycloalkano[b]dihydroindoles and -indolesulphonamides, substituted by heterocycles, of the formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and represent hydrogen, nitro, cyano, halogen, trifluoromethyl, carboxyl, hydroxyl or trifluoromethoxy, or represent a group of the formula --S(O).sub.w R.sup.5, in which R.sup.5 denotes alkyl or optionally substituted aryl, w denotes the number 0, 1 or 2, or represents alkoxy or alkoxycarbonyl, or benzyloxy, or represents a group of the formula --NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 are identical or different and denote hydrogen, alkyl or acyl or denote aryl, or denote a group of the formula --S(O).sub.w R.sup.5, in which R.sup.5 and w have the abovementioned meaning, represent cycloalkyl or represent optionally substituted alkyl or alkenyl, m represents the number 1, 2, 3 or 4, n represents the number 0, 1 or 2, z represents the number 1, 2, 3 or 4, A represents a bond or the --NH group, X represents an optionally substituted heterocycle, Y represents hydroxyl, alkoxy, phenoxy or a group of the formula --NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 have the abovementioned meaning, an isomeric form thereof or salts thereof are useful to treat thromboembolisms, ischaemias, asthma and allergies. Processes of making and chemical intermediates are also disclosed.

Claims14

Dependent claims

A heterocyclyl substituted cycloalkano[b]dihydroindole or -indolesulphonamide of the formula ##STR28## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and

represent hydrogen, nitro, cyano, halogen, trifluoromethyl, carboxyl, hydroxyl or trifluoromethoxy, or
represent a group of the formula --S(O).sub.w R.sup.5, in which
R.sup.5 denotes straight-chain or branched alkyl having up to 8 carbon atoms or aryl having 6 to 10 carbon atoms, which is optionally substituted by halogen, nitro, cyano or trifluoromethyl,
w denotes the number 0, 1 or 2, or
represents straight-chain or branched alkoxy or alkoxycarbonyl in each case having up to 10 carbon atoms, or benzyloxy, or
represents a group of the formula --NR.sup.6 R.sup.7, in which
R.sup.6 and R.sup.7 are identical or different and
denote hydrogen, straight-chain or branched alkyl or acyl in each case having up to 8 carbon atoms or
denote aryl having 6 to 10 carbon atoms, or
denote a group of the formula --S(O).sub.w R.sup.5, in which R.sup.5 and w have the abovementioned meaning,
represent cycloalkyl having 3 to 8 carbon atoms or
represent aryl having 6 to 10 carbon atoms, or
represent straight-chain or branched alkyl or alkenyl in each case having up to 10 carbon atoms, which are optionally substituted by halogen, hydroxyl, carboxyl, cyano, aryl having 6 to 10 carbon atoms, straight-chain or branched alkyl, alkoxy or alkoxycarbonyl in each case having up to 8 carbon atoms or by a group of the formula ##STR29## in which w, R.sup.5, R.sup.6 and R.sup.7 have the abovementioned meaning, m represents the number 1, 2, 3 or 4,
n represents the number 0, 1 or 2,
z represents the number 1, 2, 3 or 4,
A represents a bond or the --NH group,
X represents pyridyl, pyrimidyl, pyridazyl, quinolyl, morpholinyl, piperidinyl, thienyl, pyrryl, oxazolyl, isoxazolyl, imidazolyl, thiazolyl or isothiazolyl, which are optionally monosubstituted or disubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, trifluoromethyl, trifluoromethoxy, hydroxyl or straight-chain or branched alkyl having up to 6 carbon atoms,
Y represents hydroxyl, alkoxy having up to 8 carbon atoms, phenoxy or a group of the formula --NR.sup.6 R.sup.7, in which
R.sup.6 and R.sup.7 have the abovementioned meaning, an isomeric form thereof, or a salt thereof.

16 more elements

A compound of the formula ##STR36## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and

represent hydrogen, nitro, cyano, halogen, trifluoromethyl, carboxyl, hydroxyl or trifluoromethoxy, or
represent a group of the formula --S(O).sub.w R.sup.5, in which
R.sup.5 denotes straight-chain or branched alkyl having up to 8 carbon atoms or aryl having 6 to 10 carbon atoms, which is optionally substituted by halogen, nitro, cyano or trifluoromethyl,
w denotes the number 0, 1 or 2, or
represents straight-chain or branched alkoxy or alkoxycarbonyl in each case having up to 10 carbon atoms, or benzyloxy, or
represents a group of the formula --NR.sup.6 R.sup.7, in which
R.sup.6 and R.sup.7 are identical or different and
denote hydrogen, straight-chain or branched alkyl or acyl in each case having up to 8 carbon atoms or
denote aryl having 6 to 10 carbon atoms, or
denote a group of the formula --S(O).sub.w R.sup.5, in which R.sup.5 and w have the abovementioned meaning,
represent cycloalkyl having 3 to 8 carbon atoms or
represent aryl having 6 to 10 carbon atoms, or
represent straight-chain or branched alkyl or alkenyl in each case having up to 10 carbon atoms, which are optionally substituted by halogen, hydroxyl, carboxyl, cyano, aryl having 6 to 10 carbon atoms, straight-chain or branched alkyl, alkoxy or alkoxycarbonyl in each case having up to 8 carbon atoms or by a group of the formula ##STR37## in which w, R.sup.5, R.sup.6 and R.sup.7 have the abovementioned meaning,
n represents the number 0, 1 or 2,
z represents the number 1, 2 ,3 or 4,
A represents a bond or the --NH group,
x represents pyridyl, pyrimidyl, pyridazyl, quinolyl, morpholinyl, piperidinyl, thienyl, pyrryl, oxazolyl, isoxazolyl, imidazolyl, thiazolyl or isothiazolyl, which are optionally monosubstituted or disubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, trifluoromethyl, trifluoromethoxy, hydroxyl or straight-chain or branched alkyl having up to 6 carbon atoms,
Y represents hydroxyl, alkoxy having up to 8 carbon atoms, phenoxy or a group of the formula --NR.sup.6 R.sup.7, in which
R.sup.6 and R.sup.7 have the abovementioned meaning.

16 more elements

Dependencies are inferred from the claim text.