Merck Patent Gesellschaft MIT Beschrankter Haftung

Merck Patent Gesellschaft MIT Beschraenkter Haftung

Jurgen Uhl

Christoph Seyfried

Hans-Heinrich Hausberg

Helmut Prucher

Klaus Otto Minck

Klaus Irmscher

Helmut Muller-Calgan

Klaus-Otto Minck

Rochus Jonas

Wighard Strehlow

Dieter Marx

Eike Poetsch

Hans-Adolf Kurmeier

Helmut Wahlig

Ernst Schorscher

Volkmar Rudolph

Giuliano Dolce

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

Adenosine derivatives of formula I ##STR1## wherein X is F, Cl or Br and n is 1 or 2, and their physiologically acceptable acid addition salts, are valuable psychopharmacological agents.

Use of adenosine derivatives as psychopharmacological agents

Adenosine derivatives of formula I ##STR1## wherein R is H, F, Cl, Br or CF.sub.3, and their physiologically acceptable acid addition salts, are valuable anticonvulsants.

Use of adenosine derivatives as anticonvulsants

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

Basic thioethers

3-Fluoro-2,3-dihydro-1H-1,4-benzodiazepin-2-ones of the formula ##STR1## wherein R.sup.1 is H, alkyl or fluorinated alkyl of 1-4 carbon atoms and up to 9 fluorine atoms or cycloalkylalkyl of 4-8 carbon atoms; R.sup.2 is phenyl; monohalophenyl or pyridyl; R.sup.3 is F, Cl, Br or NO.sub.2, and physiologically acceptable acid addition salts thereof, are central nervous system depressants.

3-Fluorobenzodiazepines

Phenoxy heterocyclic amines and use thereof

Tetralone and indanone compounds of the formula ##STR1## wherein R.sup.1 is H, OH, alkoxy of 1-4 carbon atoms, cycloalkoxy of 3-6 carbon atoms, F, Cl, Br, NO.sub.2, monoalkylamino or dialkylamino, wherein each alkyl is of 1-4 carbon atoms, alkanoyloxy of 1-6 carbon atoms or alkanoylamino of 1-4 carbon atoms; R.sup.2 is OH or alkoxy of 1-4 carbon atoms or R.sup.1 and R.sup.2 collectively are methylenedioxy; R.sup.3 is H or CH.sub.3 ; Ar is phenyl or phenyl substituted by up to 5 of alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, F, Cl, Br or CF.sub.3 ; n is 1 or 2, and physiologically acceptable acid addition salts thereof, are central nervous system depressants.

Growing community of inventors

Seeheim, Germany

Jurgen Uhl