Kali-chemie Pharma Gmbh

Gerd Buschmann

Ulrich G Kuehl

Wolfgang Kehrbach

Bernd Hachmeister

Uwe Schoen

Ulrich G Kuhl

Renke Budden

Heinrich-Wilhelm Ohlendorf

Wilhelm Kaupmann

Stephen J Magda

Joachim Wegener

Uwe Schon

Wolfgang Milkowski

Dieter Ziegler

Samuel David

Peter W Thies

Henning Heinemann

Arman Farjam

Kurt Burow

Gerda Varchmin

Peter Flecker

Deiter Ziegler

A method of treating a mammal in need of diruetic treatment by administering an effective diuretic amount of a diuretically active 3,7,9,9-tetrasubstituted 3,7-diazabicyclo[3,3,1]nonane compound, diuretic pharmaceutical compositions containing an effective diuretic amount of a diuretically active 3,7,9,9-tetrasubstituted 3,7-diazabicyclo[3,3,1]nonane compound; and previously unknown diuretically active 3,7,9,9-tetrasubstituted 3,7-diazabicyclo[3,3,1]nonane compounds containing an optionally substituted phenylalkyl group in the 3-position.

Method of diuretic treatment with 3,7-diazabicyclo[3,3,1]nonane compounds

New 1-phenyl-2-aminocarbonylindole compounds are described which have the general formula I ##STR1## where R.sub.1 is a hydrogen atom, or a lower alkyl, alkenyl, cycloalkyl or cycloalkylalkyl radical, R.sub.2 is a hydrogen atom or a lower alkyl radical, R.sub.3 is a hydrogen or halogen atom, or a lower alkyl, hydroxyl or lower alkoxy radical, R.sub.4 is a hydrogen or halogen atom, or a lower alkyl, hydroxyl or lower alkoxy radical, or, if R.sub.3 is a hydrogen atom, R.sub.4 may be a nitro or trifluoromethyl radical, or R.sub.3 and R.sub.4 together denote a methylenedioxy or ethylenedioxy radical, R.sub.5 has the meanings given for R.sub.3, R.sub.6 has the meanings given for R.sub.4, R.sub.7 is a hydrogen atom or, if R.sub.5 and R.sub.6 are lower alkoxy radicals, R.sub.7 may also be a lower alkoxy radical, R.sub.8 and R.sub.9 are each a hydrogen atom or a lower alkyl radical or, together with the nitrogen atom, form a heterocyclic group, and Z is a alkylene chain which is optionally substituted by hydroxyl. The compounds have pharmacological properties, in particular antiarrhythmic properties. The compounds may be in the form of the free base or acid addition salts. Pharmaceutical compositions containing these compounds are described as is a method of preparing them. Valuable intermediates for the production of these compounds and methods of preparing the intermediates are also described.

1-phenyl-2-aminocarbonylindole compounds, preparation thereof and

3,7-Diazabicyclo[3,3,1]nonane compounds having valuable heart rate-affecting pharmacological properties corresponding to the Formula I: ##STR1## wherein R.sup.1 is alkyl, cycloalkylalkyl or benzyl,

3,7-diazabicyclo(3,3,1)nonane compounds and pharmaceutical compositions

Treatment of heart conditions with spartein compounds

Novel 1-phenyl-2-aminocarbonylindole compounds are disclosed having the general formula I ##STR1## wherein R.sub.1 is an aliphatic or aromatic acyl group or an optionally substituted benzyl group; R.sub.2 is hydrogen or a lower alkyl radical; R.sub.3 is a hydrogen, a halogen, a lower alkyl radical, or a lower alkoxy radical; R.sub.4 is hydrogen, a halogen, a lower alkyl radical, or a lower alkoxy radical; R.sub.5 has the significance given R.sub.3 ; R.sub.6 has the significance given for R.sub.4, or R.sub.6 is nitro or trifluoromethyl; R.sub.7 and R.sub.8 each represent hydrogen or a lower alkyl radical, or together with a nitrogen atom form a heterocyclic group; and Z signifies an alkylene chain optionally substituted by hydroxy or acyloxy. The compounds have pharmacological, in particular antiarrhythmic, properties.

New 1-phenyl-2-aminocarbonylindole compounds are described which have the general formula I ##STR1## where R.sub.1 is a hydrogen atom, or a lower alkyl, alkenyl, cycloalkylalkyl radical, R.sub.2 is a hydrogen atom or a lower alkyl radical, R.sub.3 is a hydrogen or halogen atom, or a lower alkyl, hydroxyl or lower alkoxy radical, R.sub.4 is a hydrogen or halogen atom, or a lower alkyl, hydroxyl or lower alkoxy radical, or, if R.sub.3 is a hydrogen atom, R.sub.4 may be a nitro or trifluoromethyl radical, or R.sub.3 and R.sub.4 together denote a methylenedioxy or ethylenedioxy radical, R.sub.5 has the meanings given for R.sub.3, R.sub.6 has the meanings given for R.sub.4, R.sub.7 is a hydrogen atom or, if R.sub.5 and R.sub.6 are lower alkoxy radicals, R.sub.7 may also be a lower alkoxy radical, R.sub.8 and R.sub.9 are each a hydrogen atom or a lower alkyl radical or, together with the nitrogen atom, form a heterocyclic group, and Z is an alkylene chain which is optionally substituted by hydroxyl. The compounds have pharmaceutical properties, in particular antiarrhythmic properties. The compounds may be in the form of the free bases or acid addition salts. Pharmaceutical compositions containing these compounds are described as is a method of preparing them. Valuable intermediates for the production of these compounds and methods of preparing the intermediates are also described.

1-Phenyl-2-aminocarbonylindole compounds, preparation thereof and

Spartein compounds, their preparation and use

3,7-diaza bicyclo-(3,3,1)-nonane compounds of the formula ##STR1## in which substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4, Z.sub.1, and Z.sub.2 indicate the substituents as they are given in the description of the invention, can be employed to produce certain pharmaceutically useful compounds.

Intermediates for synthesizing pharmaceutically active

N-(2,10-dioxa-tricyclo-[5,3,1,0.sup.3,8 ]-undecane-5-yl)-tryptamine compounds corresponding to the formula ##STR1## with blood-pressure lowering effects, a method of producing such compounds and pharmaceutical compositions incorporating such compounds, wherein R.sub.1 is hydrogen, a benzyl or lower alkyl group; R.sub.2 is a lower alkyl or lower alkanoyl group; R.sub.3 is hydrogen or a lower alkyl group; R.sub.4 is hydrogen, benzyloxy, hydroxy or a lower alkoxy group; R.sub.5 is hydrogen, benzyloxy, hydroxy or a lower alkoxy group; and A and B either are both hydrogen or together represent a bond between their respective carbons.

N-(2,10-dioxa-tricyclo-[5,3,1,0.sup.3,8 ]-undecane-5-yl)-tryptamine

3-(aminoalkylaminocarbonylmethoxy)-5-phenylpyrazole compounds corresponding to the formula: ##STR1## in which R.sub.1, R.sub.2, R.sub.5, R.sub.6, R.sub.7, and R.sub.8 and R.sub.9 may be hydrogen or lower alkyl groups, or R.sub.5 with R.sub.6 and/or R.sub.8 with R.sub.9 may also form specified cyclic groups, R.sub.3 and R.sub.4 may be hydrogen, halogen, lower alkyl, lower alkoxy, trifluoromethyl, nitro, hydroxy or alkylene dioxy, and Z represents an alkylene chain or the 2-hydroxypropylene chain. The compounds possess pharmacological, in particular antiarrhythmic, properties.

3-aminocarbonylmethoxy-5-phenylpyrazole compounds, antiarrythmic

New quaternary derivatives of 10-bromoajmaline and 10-bromoisoajmaline are disclosed which exhibit antiarrhythmic and adrenolytic properties and which have the formula I ##STR1## wherein R represents a carbon-attached organic group containing 1 to 10 carbon atoms and A.sup.- represents an acid anion as well as pharmaceutical formulations thereof and processes and intermediates for their preparation.

N.sub.b Quaternary derivatives of ajmaline and isoajmaline, methods and

New N.sub.b -quaternary 10-bromosandwicine and 10-bromoisosandwicine derivatives are disclosed which exhibit antiarrhythmic properties and adrenolytic properties and which have the formula I ##STR1## wherein R represents a carbon-attached organic group containing 1 to 10 carbon atoms and A.sup..crclbar. represents an acid anion, as well as pharmaceutical formulations thereof and processes and intermediates for their preparation.

N.sub.b -Quaternary derivatives of sandwicine and isosandwicine methods

Novel 3,7-diaza bicyclo-(3,3,1)-nonane compounds are described which are represented by the formula: ##STR1## wherein Z.sub.1 and Z.sub.2 each denotes hydrogen,

3,7-Diazabicyclo(3,3,1)nonane compounds and their use in treating heart

Acidiferous salts of 17-.beta.-n-pentyl sparteine are crystallized out of a solution of 17-.beta.-n-pentyl sparteine and a dicarboxylic acid selected from the group consisting of tartaric acid, fumaric acid or mixtures thereof. The novel acidiferous pentyl sparteine salts are employed in pharmaceutical compositions for the treatment of cardiac disorders and in venous therapeutical applications, and process improved stability and pharmacological properties.

Acidiferous 17-normal-pentyl sparteine tartaric and fumaric acid salts

Disclosed are a novel dimeric sparteine derivative, the 17S,17'S-bissparteine, and its physiologically compatible acid addition salts. Said compounds are produced by dimerization of 17-hydroxy sparteine or 17-dehydrosparteine salts by means of activated magnesium or an alkali metal. Pharmaceutical compositions containing said novel dimeric sparteine derivatives and their preparation are also described.

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Hanover, Germany

Gerd Buschmann