US 4,731,365 AGranted

5-aminoalkyl-beta-carboline derivatives, psycho tropic compositions and use

AssigneeSchering Corporation

InventorsHelmut Biere, Andreas Huth, Dieter Rahtz, Ralph Schmiechen, Dieter Seidelmann, David N. Stephens

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Abstract

Compounds of formula I ##STR1## wherein n is 0 or 1, R.sup.1 is hydrogen or lower alkyl, R.sup.2 and R.sup.3 each independently is hydrogen, optionally substituted lower alkyl, acyl or aryl, or together with the nitrogen atom form a 5-6-member heterocycle, R.sup.4 is hydrogen, lower alkyl or lower alkoxyalkyl and X is COOR.sup.6, CO--NR.sup.7 R.sup.8, or an oxadiazolyl radical of the formula ##STR2## wherein R.sup.5 is H, lower alkyl or cycloalkyl, R.sup.6 is H or lower alkyl, R.sup.7 and R.sup.8 each independently is hydrogen, optionally substituted lower alkyl, acyl or aryl, or R.sup.7 and R.sup.8 together with the nitrogen atom can form a 5-6-member heterocycle, are valuable drugs, e.g., have psychotropic activity.

Claims12

Dependent claims

A 5-Aminoalkyl-beta-carboline of the formula ##STR11## wherein n is 0 or 1,

R.sup.1 is hydrogen or lower alkyl,
R.sup.2 and R.sup.3 each independently is hydrogen;
alkyl;
alkyl substituted by OH, lower alkoxy, mercapto, lower alkylthio, phenyl, amino, amino substituted by lower alkyl or a 5-6-member aliphatic N-containing heterocycle which can contain an additional O, N or S atom and can be substituted by 1 or 2 lower alkyl groups;
alkanoyl;
phenyl;
or a 5-6-member aromatic heterocycle containing 1 or 2 O, N or S atoms;
or together with the adjoining N-atom R.sup.2 and R.sup.3 form a 5-6-member aliphatic N-containing heterocycle which can contain an additional O, N or S atom and can be substituted by 1 or 2 lower alkyl groups,
R.sup.4 is hydrogen, lower alkyl or lower alkoxy-lower-alkyl and
X is COOR.sup.6, or CO--NR.sup.7 R.sup.8
wherein
R.sup.6 is H or lower alkyl,
R.sup.7 and R.sup.8 each independently is hydrogen;
alkyl;
alkyl substituted by OH, lower alkoxy, mercapto, lower alkylthio, phenyl, amino, amino substituted by lower alkyl or a 5-6-member aliphatic N-containing heterocycle which can contain an additional O, N or S atom and can be substituted by 1 or 2 lower alkyl groups;
alkanoyl;
phenyl;
or a 5-6-member aromatic heterocycle containing 1 or 2 O, N or S atoms;
or together with the adjoining N-atom R.sup.2 and R.sup.3 form a 5-6-member aliphatic N-containing heterocycle which can contain an additional O, N, or S atom and can be substituted by 1 or 2 lower alkyl groups,
and "lower" refers to 1-6 carbon atoms.

17 more elements

5-Phenylaminomethyl-beta-carboline-3-carboxylic acid ethyl ester

5-(1-imidazolylmethyl)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester
4-methoxymethyl-5-(4-morpholinyl)-beta-carboline-3-carboxylic acid ethyl ester
4-methoxymethyl-5-(4-methyl-1-piperazinylmethyl)-beta-carboline-3-carboxyli c acid ethyl ester
4-methoxymethyl-5-(1-piperidinylmethyl)-beta-carboline-3-carboxylic acid ethyl ester
4-methoxymethyl-5-(2,6-dimethyl-4-morpholinylmethyl)-beta-carboline-3-carbo xylic acid ethyl ester
4-methoxymethyl-5-diethylaminomethyl)-beta-carboline-3-carboxylic acid ethyl ester
4-methoxymethyl-5-(2-(4-morpholinyl)-ethyl)-aminomethyl-beta-carboline-3-ca rboxylic acid ethyl ester
5-[N-(2-ethoxyethyl)-aminomethyl]-4-methoxymethyl-beta-carboline-3-carboxyl ic acid ethyl ester
4-methoxymethyl-5-dimethylaminomethyl-beta-carboline-3-carboxylic acid ethyl ester
5-[N,N-bis(2-methoxyethyl)-aminomethyl]-4-methoxymethyl-beta-carboline-3-ca rboxylic acid ethyl ester
4-methoxymethyl-5-(4-morpholinylmethyl)-beta-carboline-3-carboxylic acid
4-methoxymethyl-5-(2,6-dimethyl-4-morpholinyl-methyl)-beta-carboline-3-carb oxylic acid
4-methoxymethyl-5-(4-morpholinylmethyl)-beta-carboline-3-carboxylic acid tert-butyl ester
4-methoxymethyl-5-(2,6-dimethyl-4-morpholinyl-methyl)-beta-carboline-3-carb oxylic acid tert-butyl ester
4-methoxymethyl-5-(4-morpholinylmethyl)-beta-carboline-3-carboxylic acid isopropyl ester
4-methoxymethyl-5-(1-pyrrolidinylmethyl)-beta-carboline-3-carboxylic acid isopropyl ester
4-methoxymethyl-5-(4-thiomorpholinylmethyl)-beta-carboline-3-carboxylic acid isopropyl ester
4-methoxymethyl-5-(2,6-dimethyl-4-morpholinylmethyl)-beta-carboline-3-carbo xylic acid isopropyl ester
5-morpholino-methyl-beta-carboline-3-carboxylic acid ethyl ester
5-(4-methylpiperazinylmethyl)-beta-carboline-3-carboxylic acid ethyl ester
5-[N-(1-phenylethyl)-aminomethyl]-beta-carboline-3-carboxylic acid ethyl ester
5-(1-imidazolylmethyl)-beta-carboline-3-carboxylic acid ethyl ester
5-(1-imidazolylmethyl)-beta-carboline-3-carboxylic acid ethyl ester
5-(2-aminoethyl)-4-methyl-beta-carboline-3-carboxylic acid ethyl ester or
5-(2-aminopropyl)-4-methyl-beta-carboline-3-carboxylic acid ethyl ester.

22 more elements

Dependencies are inferred from the claim text.