Merck Patent Gesellschaft MIT Beschrankter Haftung

Merck Patent Gesellschaft MIT Beschraenkter Haftung

Hans-Heinrich Hausberg

Christoph Seyfried

Klaus-Otto Minck

Henning Bottcher

Rudolf Gottschlich

Jurgen Uhl

Helmut Prucher

Klaus Otto Minck

Rolf Bergmann

Eike Poetsch

Helmut Muller-Calgan

Wighard Strehlow

Dieter Marx

Otto Saiko

Volker Koppe

Henning Bottch

Indole derivatives of the general formula I ##STR1## wherein Ind is an indol-3-yl radical which is substituted by a hydroxymethyl or COW group and can additionally be monosubstituted or disubstituted by alkyl, O-alkyl, OH, F, Cl or Br,

Indole-3-yl-A-tetrahydropyridyl or piperidyl compounds

3-[4-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)butyl]-5-hydroxy-indole

Indole derivatives of the general formula I ##STR1## in which Ind is a 3-indolyl radical which can be substituted once or twice by alkyl, O-alky, S-alkyl, SO-alkyl, SO.sub.2 -alkyl, OH, F, Cl, Br, CF.sub.3 and/or CN or by a methylenedioxy group, A is --(CH.sub.2).sub.4 -- or --CH.sub.2 --L--CH.sub.2 CH.sub.2 --, L is --S--, --SO-- or --SO.sub.2 --, and Th is a 2-- or 3-thienyl radical, and in which the alkyl groups each have 1-4 C atoms, and their physiologically acceptable acid addition salts exhibit effects on the central nervous system.

Indole containing, 2-thienyl-1,2,3,6-tetrahydropyridyls and their

New indole derivatives of the general formula I ##STR1## in which Ind is a 3-indolyl radical which can be substituted by a hydroxymethyl, methylenedioxy, S-alkyl, SO-alkyl, SO.sub.2 -alkyl, CN or COW group and/or can be substituted once or twice by alkyl, O-alkyl, OH, F, Cl or Br,

Substituted indole compounds which have useful effects on the central

Basic ethers of the formula ##STR1## wherein Z is CH.sub.3 --NR.sup.2 --CH.sub.2 CH.sub.2 --CHR.sup.1 --, (1-R.sup.2 -3-piperidyl)-CHR.sup.3 --, (1-R.sup.2 -2-piperidyl)--CH.sub.2 --CHR.sup.3 -- or 1-R.sup.2 -3-R.sup.4 -hexahydroazepinyl; R.sup.1 is cyclopropyl or Ar; R.sup.2 is H, alkyl of 1-4 C atoms, alkenyl of 2-4 C atoms, cycloalkylalkyl of 4-8 C atoms or benzyl; R.sup.3 is H or Ar; R.sup.4 is H or alkyl of 1-4 C atoms, Y is --O--CHQ.sup.1 --CHQ.sup.2 --CH.sub.2 --, --O--CHQ.sup.1 --CHQ.sup.2 --CO--, --O--CQ.sup.1 .dbd.CQ.sup.2 --CO-- or --CH.sub.2 --CHQ.sup.1 --CHQ.sup.2 --CO--; Q.sup.1 and Q.sup.2 are independently each H, alkyl of 1-4 C atoms, cycloalkyl or alkylcycloalkyl each of 3-6 total C atoms or Ar; and Ar is phenyl or phenyl substituted by F, Cl, alkoxy or alkylthio, each of 1-4 C atoms, methylenedioxy or CF.sub.3 ; with the proviso that when Z is (CH.sub.3).sub.2 N--CH.sub.2 CH.sub.2 --CHR.sup.1 in 7-position and Y is --O--C(C.sub.6 H.sub.5).dbd.CH--CO-- or --O--C(C.sub.6 H.sub.5).dbd.C(CH.sub.3)--CO--, R.sup.1 is cyclopropyl, or phenyl substituted by F, Cl, alkoxy or alkylthio, each of 1-4 C atoms, methylenedioxy or CF.sub.3 ;

Aminopropoxy-chromones useful as antidepressants

Indole derivatives

Hydroxyindole derivatives of the Formula I ##STR1## wherein Ind denotes a 4-, 5-, 6- or 7-hydroxyindole-3-yl radical, which can additionally be substituted in the 2-position by alkyl with 1-3 C atoms and/or monosubstituted or disubstituted in the benzene ring by alkyl with 1-3 C atoms, F, Cl, Br and/or CN,

Use of hydroxyindole derivatives in lowering blood pressure

Tetrahydrocarbazole derivatives of the general formula I ##STR1## in which Thc is a 1,2,3,4-tetrahydro-3-carbazolyl radical which can be substituted once or twice by alkyl, O-alkyl, S-alkyl, SO-alkyl, SO.sub.2 -alkyl, OH, F, Cl, Br, CF.sub.3 and/or CN or by a methylenedioxy group, the two radicals Y are each H or together are a C-C bond, one radical Z is Ar and the other radical Z is H, A is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 -- and Ar is a phenyl group which is unsubstituted or substituted once or twice by alkyl, O-alkyl, S-alkyl, SO-alkyl, SO.sub.2 -alkyl, OH, F, Cl, Br, CF.sub.3 and/or CN or by a methylenedioxy group, or is a 2- or 3-thienyl radical, and in which the alkyl groups each have 1-4 C atoms, and their physiologically acceptable acid addition salts have effects on the central nervous system.

Tetrahydrocarbazole derivatives and pharmaceutical compositions

Tetrahydrocarbazole derivatives of the general formula I ##STR1## in which Thc is a 1,2,3,4-tetrahydro-3-carbazolyl radical which can be substituted once or twice by alkyl, O-alkyl, S-alkyl, SO-alkyl, SO.sub.2 -alkyl, OH, F, Cl, Br, CF.sub.3 and/or CN or by a methylenedioxy group, the two radicals Y are each H or together are a C--C bond, one radical Z is Ar and the other radical Z is H, A is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 -- and Ar is a phenyl group which is unsubstituted or substituted once or twice by alkyl, O-alkyl, S-alkyl, SO.sub.2 -alkyl, OH, F, Cl, Br, CF.sub.3 and/or CN or by a methylenedioxy group, or is a 2- or 3-thienyl radical, and in which the alkyl groups each have 1-4 C atoms, and their physiologically acceptable acid addition salts have effects on the central nervous system.

Method of treating psychosis using tetrahydrocarbazole derivatives

Sulfur-containing indole derivatives of the general formula I ##STR1## wherein Ind is a 3-indolyl radical which can be substituted once or twice by alkyl, O-alkyl, S-alkyl, SO-alkyl, SO.sub.2 -alkyl, OH, F, Cl, Br, CF.sub.3 and/or CN by a methylenedioxy group, A is --(CH.sub.2).sub.n --E--C.sub.m H.sub.2m -- or --(CH.sub.2).sub.n --E--C.sub.m-1 H.sub.2m-2 CO--, n is 0 or 1, m is 2, 3 or 4, E is S, SO or SO.sub.2 and Ar is a phenyl group which is unsubstituted or substituted once or twice by alkyl, O-alkyl, S-alkyl, SO-alkyl, SO.sub.2 -alkyl, OH, F, Cl, Br, CF.sub.3 and/or CN or by a methylenedioxy group and wherein the alkyl groups each have 1-4 C atoms, and their physiologically acceptable acid addition salts exhibit effects on the central nervous system.

Sulfur-containing indole derivatives

Tetrahydrocarbazole derivatives of the general formula I ##STR1## in which Thc is a 1,2,3,4-tetrahydro-3-carbazolyl radical which can be substituted once or twice by alkyl, O-alkyl, S-alkyl, SO-alkyl, SO.sub.2 -alkyl, OH, F, Cl, Br, CF.sub.3 and/or CN or by a methylenedioxy group, the two radicals Y are each H or together are a C--C bond, one radical Z is Ar and the other radical Z is H, A is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 -- and Ar is a phenyl group which is unsubstituted or substituted once or twice by alkyl, O-alkyl, S-alkyl, SO-alkyl, SO.sub.2 -alkyl, OH, F, Cl, Br, CF.sub.3 and/or CN or by a methylenedioxy group, or is a 2- or 3-thienyl radical, and in which the alkyl groups each have 1-4 C atoms, and their physiologically acceptable acid addition salts have effects on the central nervous system.

Tetrahydrocarbazole derivatives

Basic ethers of the formula ##STR1## wherein Z is CH.sub.3 -NR.sup.2 -CH.sub.2 CH.sub.2 -CHR.sup.1 --, (1-R.sup.2 -3-piperidyl)-CHR.sup.3 --, (1-R.sup.2 -2-piperidyl)-CH.sub.2 -CHR.sup.3 -- or 1-R.sup.2 -3-R.sup.4 -- hexahydroazepinyl; R.sup.1 is cyclopropyl or Ar; R.sup.2 is H, alkyl of 1-4 C atoms, alkenyl of 2-4 C atoms, cycloalkylalkyl of 4-8 C atoms or benzyl; R.sup.3 is H or Ar; R.sup.4 is H or alkyl of 1-4 C atoms, Y is --O-CHQ.sup.1 -CHQ.sup.2 -CH.sub.2 --, --O-CHQ.sup.1 -CHQ.sup.2 -CO--, --O-CQ.sup.1 .dbd.CQ.sup.2 -CO-- or --CH.sub.2 -CHQ.sup.1 -CHQ.sup.2 -CO--; Q.sup.1 and Q.sup.2 are independently each H, alkyl of 1-4 C atoms, cycloalkyl or alkylcycloalkyl each of 3-6 total C atoms or Ar; and Ar is phenyl or phenyl substituted by F, Cl, alkoxy or alkylthio, each of 1-4 C atoms, methylenedioxy or CF.sub.3 ; with the proviso that when Z is (CH.sub.3).sub.2 N-CH.sub.2 CH.sub.2 -CHR.sup.1 in 7-position and Y is --O-C(C.sub.6 H.sub.5).dbd.CH-CO-- or --O-C(C.sub.6 H.sub.5).dbd.C(CH.sub.3)-CO--, R.sup.1 is cyclopropyl, or phenyl substituted by F, Cl, alkoxy or alkylthio, each of 1-4 C atoms, methylenedioxy or CF.sub.3 ; or a physiologically acceptable acid addition salt thereof, have valuable pharmacological properties, e.g., are antidepressants.

Basic ethers useful as antidepressant agents

Cyclopropane derivatives of the formula ##STR1## wherein Ar is phenyl or phenyl monosubstituted or polysubstituted by F, Cl, Br, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.2-4 alkenyloxy, C.sub.1-4 alkylthio, OH, SH, CN, methylenedioxy or CF.sub.3 ; and R is H, C.sub.1-4 alkyl or benzyl, or a physiologically acceptable acid addition salt thereof, have valuable pharmacological properties, e.g., as antidepressants.

Pharmacologically active cyclopropane derivatives

Basic ethers of the formula ##STR1## wherein Z is CH.sub.3 --NR.sup.2 --CH.sub.2 CH.sub.2 --CHR.sup.1 --, (1-R.sup.2 -3-piperidyl)-CHR.sup.3 --, (1-R.sup.2 -2-piperidyl)-CH.sub.2 --CHR.sup.3 - or 1-R.sup.2 -3-R.sup.4 -hexahydroazepinyl; R.sup.1 is cyclopropyl or Ar; R.sup.2 is H, alkyl of 1-4 C atoms, alkenyl of 2-4 C atoms, cycloalkylalkyl of 4-8 C atoms or benzyl; R.sup.3 is H or Ar; R.sup.4 is H or alkyl of 1-4 C atoms, Y is --O--CHQ.sup.1 --CHQ.sup.2 --CH.sub.2 --, --O--CHQ.sup.1 --CHQ.sup.2 --CO--, --O--CQ.sup.1 .dbd.CQ.sup.2 --CO-- or --CH.sub.2 --CHQ.sup.1 --CHQ.sup.2 --CO--; Q.sup.1 and Q.sup.2 are independently each H, alkyl of 1-4 C atoms, cycloalkyl or alkylcycloalkyl each of 3-6 total C atoms or Ar; and Ar is phenyl or phenyl substituted by F, Cl, alkoxy or alkylthio, each of 1-4 C atoms, methylenedioxy or CF.sub.3 ; with the proviso that when Z is (CH.sub.3 ).sub.2 N--CH.sub.2 CH.sub.2 --CHR.sup.1 in 7-position and Y is --O--C(C.sub.6 H.sub.5).dbd.CH--CO-- or --O--C(C.sub.6 H.sub.5).dbd.C(CH.sub.3)--CO--, R.sup.1 is cyclopropyl, or phenyl substituted by F, Cl, alkoxy or alkylthio, each of 1-4 C atoms, methylenedioxy or CF.sub.3 ; or a physiologically acceptable acid addition salt thereof, have valuable pharmacological properties, e.g., are antidepressants.

Hexahydroazepinyloxy-chromones useful as antidepressants

Indolealkylamines of the formula ##STR1## wherein Ind is 1-R.sup.4 -2-R.sup.5 -indol-3-yl or the corresponding group in which the benzene ring is monosubstituted to trisubstituted by alkyl, O-alkyl, S-alkyl, OH, F, Cl, Br, CF.sub.3 or CN; A is --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.3 --CO-- or --CO--(CH.sub.2).sub.2 --CO--; R.sup.1 is H or methyl; R.sup.2 is H or together with R.sup.3 is a C--C bond; R.sup.3 is H or together with R.sup.2 is a C--C bond; R.sup.4 and R.sup.5 are each H, alkyl, or phenyl; and Ar is phenyl or phenyl monosubstituted or disubstituted by alkyl, F, Cl, Br, I or CF.sub.3 ; wherein alkyl in each case is of 1-4 carbon atoms;

Growing community of inventors

Ober-Ramstadt, Germany

Hans-Heinrich Hausberg